premierpropfl.com Search Results

There is a side of island life reserved for those who demand the truly extraordinary—where the powdery white sands of the Gulf of Mexico serve as your literal backyard. Welcome to one of the most iconic and recognized beachfront estates on Anna Maria Island. Masterfully designed by the renowned architect Emily Anne Smith, this classic Coastal West Indies–inspired residence stands as a testament to timeless beauty, architectural elegance, and flawless coastal craftsmanship. Built by Whitehead Construction—one of the region’s premier custom luxury builders—every square inch of this estate reflects uncompromising quality and structural excellence. Spanning four spacious bedrooms and four bathrooms (including three luxurious ensuites), the home is perfectly positioned to capture breathtaking, unobstructed turquoise water views from nearly every vantage point. The moment you step through the door, the home’s grand sense of scale and elegant features become immediately apparent. Soaring vaulted ceilings and expansive windows invite an abundance of natural light, beautifully complementing the rich hardwood flooring and meticulous custom millwork found throughout. At the heart of the home is a chef’s dream kitchen, fully equipped for effortless entertaining. It boasts expansive quartz countertops, a large custom pantry cabinet wall, and a suite of premium professional appliances. Culinary enthusiasts will appreciate the Wolf double oven with a six-burner gas cooktop, a three appliance package by Signature Kitchen Suite including a high-capacity refrigerator, a wine cooler, and dishwasher. Additionally a bonus, premium Fisher & Paykel double-drawer dishwasher is perfect for effortless clean-up. The entire second floor is dedicated to the ultimate primary retreat. Here, you can wake up every morning to direct, panoramic views of the Gulf, completely immersed in tranquility. The outdoor living spaces are equally spectacular, designed to maximize Florida’s indoor-outdoor lifestyle. Relax on the sprawling first-level patio, or ascend to the massive rooftop viewing deck—the ultimate front-row seat for Anna Maria Island’s legendary, world-class sunsets. Anchoring the outdoor oasis is a private saltwater pool, which has been completely redesigned from the resurfacing and custom tiles to all-new, state-of-the-art pool equipment. This is a rare, once-in-a-lifetime opportunity to acquire a legendary piece of Anna Maria Island paradise. To experience this coastal masterpiece firsthand, contact listing agent Gregg Bayer to arrange your private, confidential showing. Sent from my iPhone

4 Beds ⋅ 4 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code

There is a side of island life reserved for those who demand the truly extraordinary—where the powdery white sands of the Gulf of Mexico serve as your literal backyard. Welcome to one of the most iconic and recognized beachfront estates on Anna Maria Island. Masterfully designed by the renowned architect Emily Anne Smith, this classic Coastal West Indies–inspired residence stands as a testament to timeless beauty, architectural elegance, and flawless coastal craftsmanship. Built by Whitehead Construction—one of the region’s premier custom luxury builders—every square inch of this estate reflects uncompromising quality and structural excellence. Spanning four spacious bedrooms and four bathrooms (including three luxurious ensuites), the home is perfectly positioned to capture breathtaking, unobstructed turquoise water views from nearly every vantage point. The moment you step through the door, the home’s grand sense of scale and elegant features become immediately apparent. Soaring vaulted ceilings and expansive windows invite an abundance of natural light, beautifully complementing the rich hardwood flooring and meticulous custom millwork found throughout. At the heart of the home is a chef’s dream kitchen, fully equipped for effortless entertaining. It boasts expansive quartz countertops, a large custom pantry cabinet wall, and a suite of premium professional appliances. Culinary enthusiasts will appreciate the Wolf double oven with a six-burner gas cooktop, a three appliance package by Signature Kitchen Suite including a high-capacity refrigerator, a wine cooler, and dishwasher. Additionally a bonus, premium Fisher & Paykel double-drawer dishwasher is perfect for effortless clean-up. The entire second floor is dedicated to the ultimate primary retreat. Here, you can wake up every morning to direct, panoramic views of the Gulf, completely immersed in tranquility. The outdoor living spaces are equally spectacular, designed to maximize Florida’s indoor-outdoor lifestyle. Relax on the sprawling first-level patio, or ascend to the massive rooftop viewing deck—the ultimate front-row seat for Anna Maria Island’s legendary, world-class sunsets. Anchoring the outdoor oasis is a private saltwater pool, which has been completely redesigned from the resurfacing and custom tiles to all-new, state-of-the-art pool equipment. This is a rare, once-in-a-lifetime opportunity to acquire a legendary piece of Anna Maria Island paradise. To experience this coastal masterpiece firsthand, contact listing agent Gregg Bayer to arrange your private, confidential showing. Sent from my iPhone

2728 Avenue E, Holmes Beach

$2,095,000

Experience exceptional waterfront living in the prestigious Key Royale community of Holmes Beach! Beautifully renovated and perfectly positioned along a deep-water canal, this stunning coastal retreat boasts an impressive 100 feet of waterfront frontage, a private dock, 10,000-pound boat lift, and sparkling swimming pool, offering the ultimate Anna Maria Island lifestyle. Inside, sophisticated coastal elegance meets modern comfort with extensive renovations, all-new hurricane-impact windows, heavy-duty sliding glass doors, and beautiful plantation shutters in every room. Significant improvements include a metal roof and air-conditioning system, both approximately two years old. Lush tropical landscaping, a dedicated irrigation system, and elegant landscape lighting surrounding the home create an inviting atmosphere day and night. Designed for effortless indoor-outdoor living, the private pool and expansive waterfront setting provide the perfect backdrop for entertaining, relaxing, or enjoying breathtaking Florida evenings. Boating enthusiasts will appreciate the convenience of their own private dock and 10,000-pound lift, making days on the water an everyday luxury. Located just moments from the Key Royale Club, a private golf and social club offering membership opportunities, and minutes from Anna Maria Island's world-famous sugar-white beaches, waterfront dining, and boutique shopping. An extraordinary combination of luxury, location, and waterfront lifestyle. Welcome to your own piece of paradise at 616 Emerald Lane!

3 Beds ⋅ 3 Baths ⋅ Key Royale SubDv. ⋅ 34217 Zip Code

Experience exceptional waterfront living in the prestigious Key Royale community of Holmes Beach! Beautifully renovated and perfectly positioned along a deep-water canal, this stunning coastal retreat boasts an impressive 100 feet of waterfront frontage, a private dock, 10,000-pound boat lift, and sparkling swimming pool, offering the ultimate Anna Maria Island lifestyle. Inside, sophisticated coastal elegance meets modern comfort with extensive renovations, all-new hurricane-impact windows, heavy-duty sliding glass doors, and beautiful plantation shutters in every room. Significant improvements include a metal roof and air-conditioning system, both approximately two years old. Lush tropical landscaping, a dedicated irrigation system, and elegant landscape lighting surrounding the home create an inviting atmosphere day and night. Designed for effortless indoor-outdoor living, the private pool and expansive waterfront setting provide the perfect backdrop for entertaining, relaxing, or enjoying breathtaking Florida evenings. Boating enthusiasts will appreciate the convenience of their own private dock and 10,000-pound lift, making days on the water an everyday luxury. Located just moments from the Key Royale Club, a private golf and social club offering membership opportunities, and minutes from Anna Maria Island's world-famous sugar-white beaches, waterfront dining, and boutique shopping. An extraordinary combination of luxury, location, and waterfront lifestyle. Welcome to your own piece of paradise at 616 Emerald Lane!

616 Emerald Lane, Holmes Beach

749 Manatee Avenue Unit 749, Holmes Beach

$650,000

Virtually Staged. Only a few pieces of furniture is virtually staged. JAW-DROPPING, UNOBSTRUCTED BAY VIEWS! Set on one of the highest elevations on the island, this remodeled waterfront condo came through the recent hurricanes without damage. Enjoy sunrises over Sarasota Bay from every room, dolphins and manatees from the lanai, yachts waiting on the Manatee Ave bridge, and birds flying to and from Robinson Preserve. The big-ticket items are DONE: newer HVAC, ductwork, roof, hurricane-rated windows and sliders, and water heater, plus renewed electric and plumbing, high-end lighting, solid wood doors and trim, and a full-size stackable LG washer/dryer. Popcorn ceilings gone! Walk to the beach, dining, nightlife, groceries and more, and skip the seasonal island traffic with a quick trip to the mainland. Dog-friendly community with a heated bayview pool, kayak launch, pickleball and tennis. You won’t find a better view at this price. Come see it!

2 Beds ⋅ 2 Baths ⋅ Westbay Cove South SubDv. ⋅ 34217 Zip Code

Virtually Staged. Only a few pieces of furniture is virtually staged. JAW-DROPPING, UNOBSTRUCTED BAY VIEWS! Set on one of the highest elevations on the island, this remodeled waterfront condo came through the recent hurricanes without damage. Enjoy sunrises over Sarasota Bay from every room, dolphins and manatees from the lanai, yachts waiting on the Manatee Ave bridge, and birds flying to and from Robinson Preserve. The big-ticket items are DONE: newer HVAC, ductwork, roof, hurricane-rated windows and sliders, and water heater, plus renewed electric and plumbing, high-end lighting, solid wood doors and trim, and a full-size stackable LG washer/dryer. Popcorn ceilings gone! Walk to the beach, dining, nightlife, groceries and more, and skip the seasonal island traffic with a quick trip to the mainland. Dog-friendly community with a heated bayview pool, kayak launch, pickleball and tennis. You won’t find a better view at this price. Come see it!

749 Manatee Avenue Unit 749, Holmes Beach

6200 Flotilla Drive Unit 284, Holmes Beach

$645,000

This two bedroom, two bathroom, second floor unit has gorgeous open water views all the way to the Sunshine Bridge. Spacious landscaping, a rare feature with condo developments, compliments the water views. This tranquil oasis is just steps from City Hall, the public park and boat ramp. The property’s shoreline provides fishing opportunities, and the boat slips have direct access to the Gulf. Join the avid pickleball group or take your kayak through the sheltered channels to Bimini Bay and beyond. The Westbay III condominium association has some unheralded features. Built on dredgings from the surrounding canals, it enjoys the highest elevation on the island. Even ground floor units were well above the highest storm surge ever experienced. New roofs were installed on all buildings in 2025. The extensive shoreline is protected by mangroves, avoiding the major expense of maintaining a seawall. Although the majority of owners are seasonal residents there is a tight community spirit with owners ensuring the association remains fiscally sound with condo fees among the lowest for this property..

2 Beds ⋅ 2 Baths ⋅ Westbay Point SubDv. ⋅ 34217 Zip Code

This two bedroom, two bathroom, second floor unit has gorgeous open water views all the way to the Sunshine Bridge. Spacious landscaping, a rare feature with condo developments, compliments the water views. This tranquil oasis is just steps from City Hall, the public park and boat ramp. The property’s shoreline provides fishing opportunities, and the boat slips have direct access to the Gulf. Join the avid pickleball group or take your kayak through the sheltered channels to Bimini Bay and beyond. The Westbay III condominium association has some unheralded features. Built on dredgings from the surrounding canals, it enjoys the highest elevation on the island. Even ground floor units were well above the highest storm surge ever experienced. New roofs were installed on all buildings in 2025. The extensive shoreline is protected by mangroves, avoiding the major expense of maintaining a seawall. Although the majority of owners are seasonal residents there is a tight community spirit with owners ensuring the association remains fiscally sound with condo fees among the lowest for this property..

6200 Flotilla Drive Unit 284, Holmes Beach

$925,000

Imagine having the beautiful Gulf beaches of Anna Maria Island just a short stroll from your front door. Morning walks along the shoreline, afternoons spent in the sand, and spectacular Gulf sunsets can become part of your everyday routine. Welcome to Turquoise Beach Bungalow, a beautifully renovated coastal retreat where the beach is close, the living is easy, and your own private island sanctuary awaits. Thoughtfully reimagined inside and out in 2024–2025, this charming three-bedroom home brings together the character of old Florida with the comfort and convenience of modern living. Original terrazzo floors provide a timeless connection to the island's past, while an expanded floor plan, beautifully updated kitchen, and approximately 350-square-foot primary suite create a home that lives comfortably and effortlessly. The spacious primary suite is a retreat of its own, complete with a beautifully finished ensuite bath and both indoor and outdoor showers, perfect for rinsing off after a day at the beach. The kitchen features quartz countertops, stainless steel appliances, and generous storage, opening into welcoming living spaces designed for relaxed coastal living. A flexible third bedroom, currently enjoyed as an additional living room, offers room for visiting family and friends. Outside, the experience has become even more inviting. New fencing and thoughtfully added landscaping create a greater sense of privacy and tranquility in the generous backyard, giving this island bungalow a peaceful setting for quiet mornings, outdoor dining, and evenings under the stars. A covered patio extends the living space outdoors, while the expansive yard offers exciting possibilities for a future pool and additional outdoor entertaining areas. Beauty is only part of the story. The extensive renovation also included a new seamless metal roof, fresh stucco exterior, three new AC units, updated systems, new appliances, and a tankless water heater. These thoughtful improvements make this home as practical as it is beautiful, particularly for those seeking an easy, lock-and-leave second home. Set in a peaceful Holmes Beach neighborhood, just a short stroll from the Gulf beaches and the Intracoastal Waterway, the location offers the best of Anna Maria Island living. Centrally positioned between the island's two bridges, you are close to local restaurants, boutiques, and island favorites. Nearby city boat slips on Avenue B may also provide leasing opportunities, subject to availability. Offered turnkey furnished and ready to enjoy, Turquoise Beach Bungalow is an invitation to make island life your own. Whether you are looking for a weekend escape, a seasonal retreat, or a place to spend more time enjoying the Florida sunshine, this is a beach house designed to make every visit feel like a vacation. Come discover how wonderful it feels to have your own place at the beach. Schedule your private showing today.

3 Beds ⋅ 2 Baths ⋅ Sunrise Park SubDv. ⋅ 34217 Zip Code

Imagine having the beautiful Gulf beaches of Anna Maria Island just a short stroll from your front door. Morning walks along the shoreline, afternoons spent in the sand, and spectacular Gulf sunsets can become part of your everyday routine. Welcome to Turquoise Beach Bungalow, a beautifully renovated coastal retreat where the beach is close, the living is easy, and your own private island sanctuary awaits. Thoughtfully reimagined inside and out in 2024–2025, this charming three-bedroom home brings together the character of old Florida with the comfort and convenience of modern living. Original terrazzo floors provide a timeless connection to the island's past, while an expanded floor plan, beautifully updated kitchen, and approximately 350-square-foot primary suite create a home that lives comfortably and effortlessly. The spacious primary suite is a retreat of its own, complete with a beautifully finished ensuite bath and both indoor and outdoor showers, perfect for rinsing off after a day at the beach. The kitchen features quartz countertops, stainless steel appliances, and generous storage, opening into welcoming living spaces designed for relaxed coastal living. A flexible third bedroom, currently enjoyed as an additional living room, offers room for visiting family and friends. Outside, the experience has become even more inviting. New fencing and thoughtfully added landscaping create a greater sense of privacy and tranquility in the generous backyard, giving this island bungalow a peaceful setting for quiet mornings, outdoor dining, and evenings under the stars. A covered patio extends the living space outdoors, while the expansive yard offers exciting possibilities for a future pool and additional outdoor entertaining areas. Beauty is only part of the story. The extensive renovation also included a new seamless metal roof, fresh stucco exterior, three new AC units, updated systems, new appliances, and a tankless water heater. These thoughtful improvements make this home as practical as it is beautiful, particularly for those seeking an easy, lock-and-leave second home. Set in a peaceful Holmes Beach neighborhood, just a short stroll from the Gulf beaches and the Intracoastal Waterway, the location offers the best of Anna Maria Island living. Centrally positioned between the island's two bridges, you are close to local restaurants, boutiques, and island favorites. Nearby city boat slips on Avenue B may also provide leasing opportunities, subject to availability. Offered turnkey furnished and ready to enjoy, Turquoise Beach Bungalow is an invitation to make island life your own. Whether you are looking for a weekend escape, a seasonal retreat, or a place to spend more time enjoying the Florida sunshine, this is a beach house designed to make every visit feel like a vacation. Come discover how wonderful it feels to have your own place at the beach. Schedule your private showing today.

2713 Avenue C, Holmes Beach

$529,000

Walk 1 1/2 Blocks to shopping and beach. New furnace, air conditioning, breaker panel, water heater and all new impact windows and doors. Furnished and ready for your renters which can be done weekly. There is NO HOA and no monthly fees. Sellers have a flood insurance policy, fully transferable with 18 months remaining. FULL MASONRY CONSTRUCTION.

2 Beds ⋅ 2 Baths ⋅ Casanas Sub SubDv. ⋅ 34217 Zip Code

Walk 1 1/2 Blocks to shopping and beach. New furnace, air conditioning, breaker panel, water heater and all new impact windows and doors. Furnished and ready for your renters which can be done weekly. There is NO HOA and no monthly fees. Sellers have a flood insurance policy, fully transferable with 18 months remaining. FULL MASONRY CONSTRUCTION.

4004 6th Avenue Unit 2, Holmes Beach

$649,000

Your Anna Maria Island getaway awaits! Just steps from the sugar-white sands and turquoise waters of the Gulf, this beautifully appointed 2-bedroom, 2-bath condo offers the perfect combination of coastal charm, convenience, and island living. Located in The Palms on 34th Street, an intimate four-unit condominium community, this property provides a refreshing alternative to larger condo complexes. Offered furnished, the residence features an inviting, open living space, a well-equipped kitchen with granite countertops and stainless steel appliances, and comfortable accommodations designed for relaxing after a day at the beach. Each unit enjoys the convenience of private laundry and additional storage for all your beach essentials. Spend your mornings strolling along the shoreline, afternoons lounging by the community's heated pool, and evenings enjoying spectacular Gulf Coast sunsets. With the beach just a short walk away, every day feels like a vacation. Whether you're searching for a personal island retreat, a seasonal escape, or an investment opportunity, this property offers outstanding flexibility in one of Florida's most sought-after coastal destinations. With a minimum one-week rental period, the opportunity to enjoy the property personally while exploring rental income potential adds to its appeal. A prime island location, a boutique coastal setting, and the laid-back lifestyle that makes Anna Maria Island so special. Your slice of paradise is waiting!

2 Beds ⋅ 2 Baths ⋅ Casanas Sub SubDv. ⋅ 34217 Zip Code

Your Anna Maria Island getaway awaits! Just steps from the sugar-white sands and turquoise waters of the Gulf, this beautifully appointed 2-bedroom, 2-bath condo offers the perfect combination of coastal charm, convenience, and island living. Located in The Palms on 34th Street, an intimate four-unit condominium community, this property provides a refreshing alternative to larger condo complexes. Offered furnished, the residence features an inviting, open living space, a well-equipped kitchen with granite countertops and stainless steel appliances, and comfortable accommodations designed for relaxing after a day at the beach. Each unit enjoys the convenience of private laundry and additional storage for all your beach essentials. Spend your mornings strolling along the shoreline, afternoons lounging by the community's heated pool, and evenings enjoying spectacular Gulf Coast sunsets. With the beach just a short walk away, every day feels like a vacation. Whether you're searching for a personal island retreat, a seasonal escape, or an investment opportunity, this property offers outstanding flexibility in one of Florida's most sought-after coastal destinations. With a minimum one-week rental period, the opportunity to enjoy the property personally while exploring rental income potential adds to its appeal. A prime island location, a boutique coastal setting, and the laid-back lifestyle that makes Anna Maria Island so special. Your slice of paradise is waiting!

3302 6th Avenue Unit 1, Holmes Beach

$1,795,000

YOUR GULF FRONT ESCAPE AWAITS YOU! Discover the ultimate blend of coastal luxury, island charm, and investment potential in this exceptional Top Floor 3 bedroom, 2.5-bathroom condominium being sold Turnkey- overlooking the sparkling Gulf of Mexico. Nestled within the charming, village-inspired community of La Casa Costiera, this distinctive residence offers the rare opportunity to embrace the beauty of beachfront living while owning a highly desirable vacation retreat on Anna Maria Island. Inside, thoughtful design and upscale finishes create an inviting atmosphere of timeless elegance. The gourmet kitchen features granite countertops, rich wood cabinetry, and stainless steel appliances, while the spacious primary bathroom offers dual showers and a luxurious hydro-massage tub. A cozy fireplace, wet bar, and elegant crown molding add character and refinement throughout, creating the perfect setting for relaxing after a sun-filled day along the coast. Enjoy the convenience of a shared private elevator that opens directly to your front door, a two-car garage, and additional storage for all your beach and recreational essentials. Community amenities elevate the experience even further, including a heated swimming pool, spa, grilling area, and outdoor shower. Beyond the luxury, the location is what truly sets this property apart. With the Gulf of Mexico as your backdrop and the island's beautiful sugar-sand beaches just steps away, this condominium offers the kind of coastal lifestyle that continues to attract vacationers seeking an unforgettable Florida getaway. For investors, the minimum weekly rental opportunity and rarely available 3-Bedroom creates the potential to capitalize on Anna Maria Island's appeal as a sought-after vacation destination. Whether you envision a personal island escape, an income-producing rental property, or the perfect combination of both, La Casa Costiera presents an exciting opportunity to own a piece of the Gulf Coast lifestyle. Experience the beauty of Gulf-front living, the charm of Anna Maria Island, and the possibilities of owning a property that you can enjoy for years to come.

3 Beds ⋅ 3 Baths ⋅ La Costa Condominium SubDv. ⋅ 34217 Zip Code

YOUR GULF FRONT ESCAPE AWAITS YOU! Discover the ultimate blend of coastal luxury, island charm, and investment potential in this exceptional Top Floor 3 bedroom, 2.5-bathroom condominium being sold Turnkey- overlooking the sparkling Gulf of Mexico. Nestled within the charming, village-inspired community of La Casa Costiera, this distinctive residence offers the rare opportunity to embrace the beauty of beachfront living while owning a highly desirable vacation retreat on Anna Maria Island. Inside, thoughtful design and upscale finishes create an inviting atmosphere of timeless elegance. The gourmet kitchen features granite countertops, rich wood cabinetry, and stainless steel appliances, while the spacious primary bathroom offers dual showers and a luxurious hydro-massage tub. A cozy fireplace, wet bar, and elegant crown molding add character and refinement throughout, creating the perfect setting for relaxing after a sun-filled day along the coast. Enjoy the convenience of a shared private elevator that opens directly to your front door, a two-car garage, and additional storage for all your beach and recreational essentials. Community amenities elevate the experience even further, including a heated swimming pool, spa, grilling area, and outdoor shower. Beyond the luxury, the location is what truly sets this property apart. With the Gulf of Mexico as your backdrop and the island's beautiful sugar-sand beaches just steps away, this condominium offers the kind of coastal lifestyle that continues to attract vacationers seeking an unforgettable Florida getaway. For investors, the minimum weekly rental opportunity and rarely available 3-Bedroom creates the potential to capitalize on Anna Maria Island's appeal as a sought-after vacation destination. Whether you envision a personal island escape, an income-producing rental property, or the perfect combination of both, La Casa Costiera presents an exciting opportunity to own a piece of the Gulf Coast lifestyle. Experience the beauty of Gulf-front living, the charm of Anna Maria Island, and the possibilities of owning a property that you can enjoy for years to come.

7320 Gulf Drive Unit 10, Holmes Beach

$2,950,000

The Epitome of Relaxed Elegance on Anna Maria Island. Lovingly cared for and beautifully renovated in 2024, this tropical waterfront retreat blends sophisticated design with the timeless charm of coastal living in a quiet neighborhood setting. Thoughtfully appointed with upscale furnishings and refined finishes, the home exudes understated luxury and effortless island elegance. This spacious three-bedroom residence is among the largest of its kind in Holmes Beach, offering 2,647 sq ft under roof and a large 11,115 sq ft lot. The generous open floor plan features two distinct living areas, and offers flexibility for entertaining, gathering with family and friends, or simply relaxing in your own private retreat. Beautiful interiors easily flow into tropical outdoor living spaces with lush landscaping and a beautiful heated pool / waterfall, creating a tranquil, secluded island oasis. Other key features include all hurricane windows and doors, a complete plumbing repipe, gas fireplace, tropical outdoor shower, kayak storage, all new appliances, and Garrison flood gates. For boating enthusiasts, the waterfront setting is a true highlight. Enjoy deep-water canal access to the Intracoastal Waterway, 68 foot dock with electric and water, a boat lift, and a convenient fish-cleaning station. Whether heading out for a day on the water, exploring the surrounding waterways, watching manatees and dophins, kayaking, paddleboarding, or enjoying an evening sunset cruise, the island lifestyle is right at your doorstep. Feel like enjoying the island? Travel a few short blocks to Anna Maria's sandy white beaches, gourmet restaurants, stunning sunsets, and coastal shopping. Elegant yet inviting, sophisticated yet relaxed, this beautifully maintained home offers a wonderful opportunity to experience the very best of Anna Maria Island living, where coastal charm, exceptional boating, and everyday comfort come together. Click on the link for a revealing virtual tour then call for your private showing today!

3 Beds ⋅ 3 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code

The Epitome of Relaxed Elegance on Anna Maria Island. Lovingly cared for and beautifully renovated in 2024, this tropical waterfront retreat blends sophisticated design with the timeless charm of coastal living in a quiet neighborhood setting. Thoughtfully appointed with upscale furnishings and refined finishes, the home exudes understated luxury and effortless island elegance. This spacious three-bedroom residence is among the largest of its kind in Holmes Beach, offering 2,647 sq ft under roof and a large 11,115 sq ft lot. The generous open floor plan features two distinct living areas, and offers flexibility for entertaining, gathering with family and friends, or simply relaxing in your own private retreat. Beautiful interiors easily flow into tropical outdoor living spaces with lush landscaping and a beautiful heated pool / waterfall, creating a tranquil, secluded island oasis. Other key features include all hurricane windows and doors, a complete plumbing repipe, gas fireplace, tropical outdoor shower, kayak storage, all new appliances, and Garrison flood gates. For boating enthusiasts, the waterfront setting is a true highlight. Enjoy deep-water canal access to the Intracoastal Waterway, 68 foot dock with electric and water, a boat lift, and a convenient fish-cleaning station. Whether heading out for a day on the water, exploring the surrounding waterways, watching manatees and dophins, kayaking, paddleboarding, or enjoying an evening sunset cruise, the island lifestyle is right at your doorstep. Feel like enjoying the island? Travel a few short blocks to Anna Maria's sandy white beaches, gourmet restaurants, stunning sunsets, and coastal shopping. Elegant yet inviting, sophisticated yet relaxed, this beautifully maintained home offers a wonderful opportunity to experience the very best of Anna Maria Island living, where coastal charm, exceptional boating, and everyday comfort come together. Click on the link for a revealing virtual tour then call for your private showing today!

520 72nd Street, Holmes Beach

$535,000

Welcome to Cayman Cay, where your island getaway awaits just steps from the sugar sands and turquoise waters of the Gulf! Ideally located directly across from Manatee Public Beach, this charming coastal community offers the perfect combination of beachside living, convenience, and investment potential. With a newly updated rental policy allowing weekly rentals as of March 2026, this is an exciting opportunity to own an affordable investment property on Anna Maria Island! An attached rental projection estimates over $53,000 in annual gross rental income, making this an attractive option for buyers looking to enjoy their own slice of paradise while generating rental income when they are away. This turnkey furnished 2-bedroom, 2-bath condo is ready for you and your guests to start enjoying island life immediately! The beautifully updated kitchen opens to a comfortable living and dining area, with sliding doors leading to a screened lanai where you can unwind and take in the colorful evening skies. The spacious primary suite features an ensuite bath and an additional storage closet that can be locked to securely store personal belongings between rental stays. The guest bedroom is thoughtfully furnished with two twin-over-full bunk beds, offering plenty of sleeping space for family and friends, while the guest bathroom features a convenient tub/shower combination. An in-unit washer and dryer adds to the comfort and convenience of this coastal retreat. Cayman Cay offers a relaxed, resort-style atmosphere with a heated community pool, inviting gathering spaces, BBQ grilling area, and shuffleboard courts. Step across the street to spend your days on the beautiful Gulf beaches, enjoy breathtaking sunsets, or explore the nearby restaurants and shopping. The free island trolley stops curbside, making it easy to discover all of Anna Maria Island without ever getting in your car! Whether you are searching for a personal beach retreat, an income-producing vacation rental, or the best of both worlds, this beautifully furnished condo offers an exceptional opportunity to embrace the island lifestyle. Pack your bags, bring your flip-flops, and start living your Anna Maria Island dream!

2 Beds ⋅ 2 Baths ⋅ Cayman Cay Villas Condominium SubDv. ⋅ 34217 Zip Code

Welcome to Cayman Cay, where your island getaway awaits just steps from the sugar sands and turquoise waters of the Gulf! Ideally located directly across from Manatee Public Beach, this charming coastal community offers the perfect combination of beachside living, convenience, and investment potential. With a newly updated rental policy allowing weekly rentals as of March 2026, this is an exciting opportunity to own an affordable investment property on Anna Maria Island! An attached rental projection estimates over $53,000 in annual gross rental income, making this an attractive option for buyers looking to enjoy their own slice of paradise while generating rental income when they are away. This turnkey furnished 2-bedroom, 2-bath condo is ready for you and your guests to start enjoying island life immediately! The beautifully updated kitchen opens to a comfortable living and dining area, with sliding doors leading to a screened lanai where you can unwind and take in the colorful evening skies. The spacious primary suite features an ensuite bath and an additional storage closet that can be locked to securely store personal belongings between rental stays. The guest bedroom is thoughtfully furnished with two twin-over-full bunk beds, offering plenty of sleeping space for family and friends, while the guest bathroom features a convenient tub/shower combination. An in-unit washer and dryer adds to the comfort and convenience of this coastal retreat. Cayman Cay offers a relaxed, resort-style atmosphere with a heated community pool, inviting gathering spaces, BBQ grilling area, and shuffleboard courts. Step across the street to spend your days on the beautiful Gulf beaches, enjoy breathtaking sunsets, or explore the nearby restaurants and shopping. The free island trolley stops curbside, making it easy to discover all of Anna Maria Island without ever getting in your car! Whether you are searching for a personal beach retreat, an income-producing vacation rental, or the best of both worlds, this beautifully furnished condo offers an exceptional opportunity to embrace the island lifestyle. Pack your bags, bring your flip-flops, and start living your Anna Maria Island dream!

4307 Gulf Drive Unit 206, Holmes Beach

$2,095,000

**PRIME ISLAND LOCATION - STEPS TO THE BEACH - HIGHLY DESIRABLE WEEKLY RENTAL ZONING** Experience the best of Anna Maria Island living in this beautifully designed 4-bedroom, 3.5-bath coastal retreat, ideally situated just a short stroll from the pristine Gulf beaches, with dedicated beach access at the end of the street. Surrounded by the island’s celebrated restaurants, charming boutiques, and local attractions, this exceptional location offers the perfect balance of coastal luxury, convenience, and investment appeal. Whether enjoyed as a private island getaway, full-time residence, or income-producing vacation rental, the home offers an enviable combination of lifestyle and versatility. Thoughtfully designed for elevated coastal living, the floor plan seamlessly blends spacious gathering areas with comfortable private retreats. Light-filled interiors, an open-concept layout, and an effortless connection between the living, dining, and entertaining spaces create an inviting atmosphere for family and guests alike. The well-appointed kitchen anchors the main living area, while generously proportioned bedrooms offer comfort and privacy. Further enhancing the home's thoughtful design, provisions were incorporated into the original floor plan to accommodate a future elevator, offering added convenience and long-term flexibility. Outdoors, a private tropical oasis awaits, where lush landscaping surrounds a heated swimming pool, inviting lounge areas, and covered spaces ideal for alfresco dining and entertaining. From leisurely afternoons poolside to relaxed evenings beneath the palms, every element is designed to embrace the laid-back sophistication of island living. Adding to its appeal, the property's highly sought-after weekly vacation rental zoning presents an attractive opportunity for income generation while preserving the flexibility of personal enjoyment. With the Gulf's turquoise waters and powder-soft beaches just moments away, along with exceptional dining, shopping, and convenient island trolley access, this residence places the very best of Anna Maria Island within easy reach.

4 Beds ⋅ 4 Baths ⋅ Coastal Cottages Ii SubDv. ⋅ 34217 Zip Code

**PRIME ISLAND LOCATION - STEPS TO THE BEACH - HIGHLY DESIRABLE WEEKLY RENTAL ZONING** Experience the best of Anna Maria Island living in this beautifully designed 4-bedroom, 3.5-bath coastal retreat, ideally situated just a short stroll from the pristine Gulf beaches, with dedicated beach access at the end of the street. Surrounded by the island’s celebrated restaurants, charming boutiques, and local attractions, this exceptional location offers the perfect balance of coastal luxury, convenience, and investment appeal. Whether enjoyed as a private island getaway, full-time residence, or income-producing vacation rental, the home offers an enviable combination of lifestyle and versatility. Thoughtfully designed for elevated coastal living, the floor plan seamlessly blends spacious gathering areas with comfortable private retreats. Light-filled interiors, an open-concept layout, and an effortless connection between the living, dining, and entertaining spaces create an inviting atmosphere for family and guests alike. The well-appointed kitchen anchors the main living area, while generously proportioned bedrooms offer comfort and privacy. Further enhancing the home's thoughtful design, provisions were incorporated into the original floor plan to accommodate a future elevator, offering added convenience and long-term flexibility. Outdoors, a private tropical oasis awaits, where lush landscaping surrounds a heated swimming pool, inviting lounge areas, and covered spaces ideal for alfresco dining and entertaining. From leisurely afternoons poolside to relaxed evenings beneath the palms, every element is designed to embrace the laid-back sophistication of island living. Adding to its appeal, the property's highly sought-after weekly vacation rental zoning presents an attractive opportunity for income generation while preserving the flexibility of personal enjoyment. With the Gulf's turquoise waters and powder-soft beaches just moments away, along with exceptional dining, shopping, and convenient island trolley access, this residence places the very best of Anna Maria Island within easy reach.

145 50th St, Holmes Beach

$3,500,000

EXCEPTIONAL WATERFRONT INVESTMENT OPPORTUNITY ON ANNA MARIA ISLAND! Discover this stunning custom-built waterfront estate in the desirable North Point Harbor community of Holmes Beach. Currently leased and tenant-occupied, this exceptional property offers an attractive investment opportunity with the potential to become your own luxurious island vacation home or private coastal retreat. Situated along the beautiful waters of Key Royale, this impressive two-story residence offers approximately 3,640 square feet of living space, featuring 5 bedrooms, a dedicated office, 4 full bathrooms, 2 half bathrooms, and an attached two-car garage. The spacious open-concept main level features abundant natural light, inviting living and dining areas, and a beautifully appointed kitchen with white cabinetry, stainless steel appliances, a large center island, and picturesque water views. Upstairs, the expansive primary suite, additional bedrooms, dedicated office, and generous family room provide plenty of space for relaxing and entertaining. Two oversized balconies showcase breathtaking panoramic water views and refreshing coastal breezes. A BOATER'S PARADISE! Enjoy a private dock and boat lift with direct deep-water access to Tampa Bay and the Gulf of Mexico, with no bridges to open water. The screened-in swimming pool and waterfront outdoor living areas create the perfect setting for enjoying the Florida lifestyle. Additional highlights include a metal roof, coastal-inspired finishes, and spacious indoor and outdoor gathering areas. Nestled on the highly sought-after northern end of Anna Maria Island, this property offers convenient access to pristine beaches, waterfront dining, boutique shopping, community tennis courts, and the Key Royale Golf Club. Whether you're looking to expand your investment portfolio or secure a future vacation getaway, this extraordinary waterfront property offers the best of island living!

5 Beds ⋅ 6 Baths ⋅ North Point Harbour SubDv. ⋅ 34217 Zip Code

EXCEPTIONAL WATERFRONT INVESTMENT OPPORTUNITY ON ANNA MARIA ISLAND! Discover this stunning custom-built waterfront estate in the desirable North Point Harbor community of Holmes Beach. Currently leased and tenant-occupied, this exceptional property offers an attractive investment opportunity with the potential to become your own luxurious island vacation home or private coastal retreat. Situated along the beautiful waters of Key Royale, this impressive two-story residence offers approximately 3,640 square feet of living space, featuring 5 bedrooms, a dedicated office, 4 full bathrooms, 2 half bathrooms, and an attached two-car garage. The spacious open-concept main level features abundant natural light, inviting living and dining areas, and a beautifully appointed kitchen with white cabinetry, stainless steel appliances, a large center island, and picturesque water views. Upstairs, the expansive primary suite, additional bedrooms, dedicated office, and generous family room provide plenty of space for relaxing and entertaining. Two oversized balconies showcase breathtaking panoramic water views and refreshing coastal breezes. A BOATER'S PARADISE! Enjoy a private dock and boat lift with direct deep-water access to Tampa Bay and the Gulf of Mexico, with no bridges to open water. The screened-in swimming pool and waterfront outdoor living areas create the perfect setting for enjoying the Florida lifestyle. Additional highlights include a metal roof, coastal-inspired finishes, and spacious indoor and outdoor gathering areas. Nestled on the highly sought-after northern end of Anna Maria Island, this property offers convenient access to pristine beaches, waterfront dining, boutique shopping, community tennis courts, and the Key Royale Golf Club. Whether you're looking to expand your investment portfolio or secure a future vacation getaway, this extraordinary waterfront property offers the best of island living!

727 Key Royale Drive, Holmes Beach

$675,000

Fall asleep to the sound of crashing waves in this Gulf-front unit at Martinique South. Sweeping beach views stretch from the living area, kitchen, and primary bedroom, and the sand is just steps away. You’re in the heart of Holmes Beach, a block from top restaurants, shops, and the island trolley. Offered in original condition, this unit is a blank canvas for your own coastal vision. Design it exactly the way you want, from the finishes to the floor plan details. Enjoy a private covered carport, separate beach storage, a heated pool, and a tennis court. The all-inclusive HOA covers cable, internet, water, trash, and insurance, making ownership simple. Community has a 30 day rental minimum, with a max of 3 rentals per year.

2 Beds ⋅ 2 Baths ⋅ Martinique Condo SubDv. ⋅ 34217 Zip Code

Fall asleep to the sound of crashing waves in this Gulf-front unit at Martinique South. Sweeping beach views stretch from the living area, kitchen, and primary bedroom, and the sand is just steps away. You’re in the heart of Holmes Beach, a block from top restaurants, shops, and the island trolley. Offered in original condition, this unit is a blank canvas for your own coastal vision. Design it exactly the way you want, from the finishes to the floor plan details. Enjoy a private covered carport, separate beach storage, a heated pool, and a tennis court. The all-inclusive HOA covers cable, internet, water, trash, and insurance, making ownership simple. Community has a 30 day rental minimum, with a max of 3 rentals per year.

5200 Gulf Drive Unit 406, Holmes Beach

$650,000

Rarely available 3-bedroom, 3-bathroom turn-key condo in the coveted Sunbow Bay community of Holmes Beach. This spacious, light-filled island retreat features an open-concept floor plan designed for seamless living and entertaining. The expansive living area opens directly to a private porch surrounded by lush tropical landscaping and your own private dock. With three full bedrooms and three dedicated bathrooms, this unique layout offers exceptional privacy for families and guests, making it a perfect primary residence, winter getaway, or rental investment. Sunbow Bay offers premier waterfront amenities, including - Two heated community pools, tennis courts and a fishing pier. Located just minutes from the Gulf beaches, local dining, and the free island trolley, Sunbow Bay combines maintenance-free living with the ultimate Anna Maria Island lifestyle. ALL WINDOWS REPLACED 2014, NEW A/C 2020, NEW DOCK 2022.

3 Beds ⋅ 3 Baths ⋅ Sunbow Bay SubDv. ⋅ 34217 Zip Code

Rarely available 3-bedroom, 3-bathroom turn-key condo in the coveted Sunbow Bay community of Holmes Beach. This spacious, light-filled island retreat features an open-concept floor plan designed for seamless living and entertaining. The expansive living area opens directly to a private porch surrounded by lush tropical landscaping and your own private dock. With three full bedrooms and three dedicated bathrooms, this unique layout offers exceptional privacy for families and guests, making it a perfect primary residence, winter getaway, or rental investment. Sunbow Bay offers premier waterfront amenities, including - Two heated community pools, tennis courts and a fishing pier. Located just minutes from the Gulf beaches, local dining, and the free island trolley, Sunbow Bay combines maintenance-free living with the ultimate Anna Maria Island lifestyle. ALL WINDOWS REPLACED 2014, NEW A/C 2020, NEW DOCK 2022.

3803 E Bay Drive Unit 9, Holmes Beach

$1,395,000

Island living, made easy. This ground-level Anna Maria Island home is fully renovated and comes turnkey furnished, just a few short blocks from the sugar-sand beaches and the island’s sunsets. Beautifully renovated in 2025 with a fresh modern design, the nearly 2,000 square foot home includes three bedrooms, two baths and new tile flooring throughout, with an ensuite bath in the primary bedroom. The new kitchen has custom cabinetry and all new appliances (2025), and both bathrooms have been redone with custom vanities, tile and contemporary finishes. The big-ticket items are already handled, including a new A/C (2025), a tankless water heater (2023) and hurricane impact windows (2023), and the laundry room has a washer, dryer, utility sink and plenty of extra storage. Outside, you’ll find a heated saltwater pool with a new pool heater (2025), landscaping, landscape lighting, irrigation, plenty of sunny yard space and a tiki-covered pergola, plus a 10x12 storage shed. Furniture and décor are included. Call to schedule your private showing.

3 Beds ⋅ 2 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code

Island living, made easy. This ground-level Anna Maria Island home is fully renovated and comes turnkey furnished, just a few short blocks from the sugar-sand beaches and the island’s sunsets. Beautifully renovated in 2025 with a fresh modern design, the nearly 2,000 square foot home includes three bedrooms, two baths and new tile flooring throughout, with an ensuite bath in the primary bedroom. The new kitchen has custom cabinetry and all new appliances (2025), and both bathrooms have been redone with custom vanities, tile and contemporary finishes. The big-ticket items are already handled, including a new A/C (2025), a tankless water heater (2023) and hurricane impact windows (2023), and the laundry room has a washer, dryer, utility sink and plenty of extra storage. Outside, you’ll find a heated saltwater pool with a new pool heater (2025), landscaping, landscape lighting, irrigation, plenty of sunny yard space and a tiki-covered pergola, plus a 10x12 storage shed. Furniture and décor are included. Call to schedule your private showing.

504 69th Street, Holmes Beach

$975,000

Anna Maria Island, Holmes Beach duplex - awesome location in the first block from the beach. Public beach access just steps away! Each unit is a true one bedroom one bath unit with open floor plan living area. Tastefully updated and furnished and ready for you or guests to move right in! Also for sale is the sister duplex just next door at 212 66th Street which would give four units and total 12498 sq ft of dirt. Show and bring your best!

2 Beds ⋅ 2 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

Anna Maria Island, Holmes Beach duplex - awesome location in the first block from the beach. Public beach access just steps away! Each unit is a true one bedroom one bath unit with open floor plan living area. Tastefully updated and furnished and ready for you or guests to move right in! Also for sale is the sister duplex just next door at 212 66th Street which would give four units and total 12498 sq ft of dirt. Show and bring your best!

210 66th Street, Holmes Beach

$2,650,000

This is the kind of Florida home that changes the rhythm of everyday life—mornings overlooking the canal, afternoons cruising the Gulf, and evenings entertaining beside the pool beneath swaying palms. Set within the highly desirable waterfront community of Key Royale, this completely renovated 4-bedroom, 4-bath canal-front residence blends relaxed coastal living with striking modern design and exceptional boating access. Inside, soaring ceilings, clerestory windows, expansive glass, and wide-plank wood-look flooring create a light, open atmosphere that feels effortlessly sophisticated. The redesigned kitchen makes a sleek architectural statement with glossy contemporary cabinetry, quartz surfaces, a generous island, stainless steel appliances, an induction cooktop, designer lighting, and a dramatic slab backsplash. Open living and entertaining spaces flow naturally together, complemented by a custom wet bar and seamless access to the home’s outdoor retreats. The primary suite captures peaceful canal and tropical views through oversized windows and sliding glass doors. Its spa-inspired bathroom is a true showpiece, featuring a skylight, freestanding soaking tub, oversized glass-enclosed shower, sculptural floating vanity, warm wood accents, and elegant brass fixtures. Three additional bedrooms and beautifully updated bathrooms provide stylish accommodations for family and guests. Above the garage, the private fourth bedroom features its own entrance and balconies, creating an ideal guest suite, multigenerational retreat, home office, studio, or flexible bonus space. Outdoors, the home feels like a private island resort. Lush tropical landscaping surrounds an inviting pool and expansive brick-paver deck, while the covered screened lanai offers a shaded setting for dining, lounging, and entertaining. Beyond the pool, a manicured canal-side lawn leads to the seawall and private boat lift, placing boating, fishing, paddleboarding, and Gulf adventures directly outside your door. Thoughtful improvements include a new roof, four new air-conditioning systems, updated landscaping, a new garage door, and refreshed garage flooring. A distinctive benefit exclusive to this street, the property’s irrigation is supplied by a private well rather than metered city water, offering the potential for significant ongoing water savings. A brand-new well pump and irrigation system have also been installed, providing added efficiency and peace of mind. The vibrant coastal exterior, brick-paver driveway, mature palms, and layered tropical gardens create memorable curb appeal from the moment you arrive. Ideally positioned near Anna Maria Island’s renowned beaches, waterfront restaurants, local boutiques, and laid-back island attractions, this move-in-ready Key Royale waterfront home offers far more than a beautiful place to live—it offers the freedom to embrace the Florida boating lifestyle every day.

4 Beds ⋅ 4 Baths ⋅ Key Royale SubDv. ⋅ 34217 Zip Code

This is the kind of Florida home that changes the rhythm of everyday life—mornings overlooking the canal, afternoons cruising the Gulf, and evenings entertaining beside the pool beneath swaying palms. Set within the highly desirable waterfront community of Key Royale, this completely renovated 4-bedroom, 4-bath canal-front residence blends relaxed coastal living with striking modern design and exceptional boating access. Inside, soaring ceilings, clerestory windows, expansive glass, and wide-plank wood-look flooring create a light, open atmosphere that feels effortlessly sophisticated. The redesigned kitchen makes a sleek architectural statement with glossy contemporary cabinetry, quartz surfaces, a generous island, stainless steel appliances, an induction cooktop, designer lighting, and a dramatic slab backsplash. Open living and entertaining spaces flow naturally together, complemented by a custom wet bar and seamless access to the home’s outdoor retreats. The primary suite captures peaceful canal and tropical views through oversized windows and sliding glass doors. Its spa-inspired bathroom is a true showpiece, featuring a skylight, freestanding soaking tub, oversized glass-enclosed shower, sculptural floating vanity, warm wood accents, and elegant brass fixtures. Three additional bedrooms and beautifully updated bathrooms provide stylish accommodations for family and guests. Above the garage, the private fourth bedroom features its own entrance and balconies, creating an ideal guest suite, multigenerational retreat, home office, studio, or flexible bonus space. Outdoors, the home feels like a private island resort. Lush tropical landscaping surrounds an inviting pool and expansive brick-paver deck, while the covered screened lanai offers a shaded setting for dining, lounging, and entertaining. Beyond the pool, a manicured canal-side lawn leads to the seawall and private boat lift, placing boating, fishing, paddleboarding, and Gulf adventures directly outside your door. Thoughtful improvements include a new roof, four new air-conditioning systems, updated landscaping, a new garage door, and refreshed garage flooring. A distinctive benefit exclusive to this street, the property’s irrigation is supplied by a private well rather than metered city water, offering the potential for significant ongoing water savings. A brand-new well pump and irrigation system have also been installed, providing added efficiency and peace of mind. The vibrant coastal exterior, brick-paver driveway, mature palms, and layered tropical gardens create memorable curb appeal from the moment you arrive. Ideally positioned near Anna Maria Island’s renowned beaches, waterfront restaurants, local boutiques, and laid-back island attractions, this move-in-ready Key Royale waterfront home offers far more than a beautiful place to live—it offers the freedom to embrace the Florida boating lifestyle every day.

528 Key Royale Drive, Holmes Beach

$2,100,000

Increasingly Rare Ground-Level Island Living with Pool, Spa & R-2 Rental Potential in the weekly rental zone. One-story, ground-level single-family homes on Anna Maria Island are increasingly difficult to find. This charming and spacious 4-bedroom, 3½-bath home offers approximately 2,479 sq. ft. of living area, a large lot, exceptional outdoor living, and the flexibility of R-2 zoning for weekly vacation/seasonal rental use. This home has been a full time residence for the current owners. Ideally located within easy walking distance of the beautiful, white sand beaches and directly on the free island trolley route and popular holiday parade routes. This home is very quiet inside due to hurricane rated windows and roof insulation. Originally custom built in 1958 and thoughtfully expanded, the home retains its classic beach-cottage character with polished terrazzo floors, original French doors, tongue-and-groove ceilings, charming vintage details, and abundant storage. The spacious kitchen features custom cabinetry and mostly new stainless-steel appliances. A bright Florida room with four sliding glass doors opens to the private pool, spa and lanai. The L-shaped screened lanai is designed for true island living and entertaining, with an outdoor TV, speakers, ceiling fans, multiple seating and dining areas, and a stainless-steel vent hood for the propane grill. The free-form pebble finish pool and spa feature a waterfall, lighting, benches, umbrella table, and recently replaced pump, motor and filter. Solar pool heating/cooling adds to year-round enjoyment. The pool area includes an outdoor half bath and shower, non-slip surfaces, and a hurricane-resistant SuperScreen enclosure. The single-level floor plan and thoughtfully designed primary bath with an oversized walk-in shower, built-in bench and detachable showerhead provide excellent accessibility for those with limited mobility, walkers or wheelchairs. Additional features include a large front porch with swing, circular driveway, oversized garage with workshop, separate golf cart garage, fenced side yard, lush tropical landscaping, raised garden, irrigation system, central vacuum, security system and generous attic storage. Storm conscious improvements include a secured Galvalume roof, impact-resistant triple-pane windows and doors, hurricane-resistant pool screening, foam roof insulation, on-demand hot water, solar pool heating, and generator capability supported by an underground propane tank. Enjoy as a full-time residence, island retreat, or vacation rental or build new. Investor opportunity to own a spacious, ground-level home with a pool, spa, large lot, accessibility, and rental flexibility in the heart of Anna Maria Island.

4 Beds ⋅ 4 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code

Increasingly Rare Ground-Level Island Living with Pool, Spa & R-2 Rental Potential in the weekly rental zone. One-story, ground-level single-family homes on Anna Maria Island are increasingly difficult to find. This charming and spacious 4-bedroom, 3½-bath home offers approximately 2,479 sq. ft. of living area, a large lot, exceptional outdoor living, and the flexibility of R-2 zoning for weekly vacation/seasonal rental use. This home has been a full time residence for the current owners. Ideally located within easy walking distance of the beautiful, white sand beaches and directly on the free island trolley route and popular holiday parade routes. This home is very quiet inside due to hurricane rated windows and roof insulation. Originally custom built in 1958 and thoughtfully expanded, the home retains its classic beach-cottage character with polished terrazzo floors, original French doors, tongue-and-groove ceilings, charming vintage details, and abundant storage. The spacious kitchen features custom cabinetry and mostly new stainless-steel appliances. A bright Florida room with four sliding glass doors opens to the private pool, spa and lanai. The L-shaped screened lanai is designed for true island living and entertaining, with an outdoor TV, speakers, ceiling fans, multiple seating and dining areas, and a stainless-steel vent hood for the propane grill. The free-form pebble finish pool and spa feature a waterfall, lighting, benches, umbrella table, and recently replaced pump, motor and filter. Solar pool heating/cooling adds to year-round enjoyment. The pool area includes an outdoor half bath and shower, non-slip surfaces, and a hurricane-resistant SuperScreen enclosure. The single-level floor plan and thoughtfully designed primary bath with an oversized walk-in shower, built-in bench and detachable showerhead provide excellent accessibility for those with limited mobility, walkers or wheelchairs. Additional features include a large front porch with swing, circular driveway, oversized garage with workshop, separate golf cart garage, fenced side yard, lush tropical landscaping, raised garden, irrigation system, central vacuum, security system and generous attic storage. Storm conscious improvements include a secured Galvalume roof, impact-resistant triple-pane windows and doors, hurricane-resistant pool screening, foam roof insulation, on-demand hot water, solar pool heating, and generator capability supported by an underground propane tank. Enjoy as a full-time residence, island retreat, or vacation rental or build new. Investor opportunity to own a spacious, ground-level home with a pool, spa, large lot, accessibility, and rental flexibility in the heart of Anna Maria Island.

7106 Palm Drive, Holmes Beach

$1,025,000

Anna Maria Island, Holmes Beach duplex - awesome location in the first block from the beach. Public beach access just steps away! Each unit is a true one bedroom one bath unit with open floor plan living area. Tastefully updated and furnished beach cute and ready for you or guests to move right in! Also for sale is the sister duplex just next door at 210 66th Street which would give four units and total 12498 sq ft of dirt. Show and bring an offer!

2 Beds ⋅ 2 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

Anna Maria Island, Holmes Beach duplex - awesome location in the first block from the beach. Public beach access just steps away! Each unit is a true one bedroom one bath unit with open floor plan living area. Tastefully updated and furnished beach cute and ready for you or guests to move right in! Also for sale is the sister duplex just next door at 210 66th Street which would give four units and total 12498 sq ft of dirt. Show and bring an offer!

212 66th Street, Holmes Beach

7406 Marina Drive Unit A and B, Holmes Beach

$1,750,000

Turnkey Coastal Duplex | Holmes Beach, Anna Maria Island A Rare Island Opportunity | Weekly Rental Potential Discover the charm of island living with this fully furnished duplex in the heart of Holmes Beach on beautiful Anna Maria Island. Just a short stroll from the beach, this versatile property offers an exceptional opportunity to enjoy the coastal lifestyle while exploring its rental potential. Featuring two separate residences with private entrances, the property offers a flexible layout ideal for an investment property, a vacation retreat, or a combination of personal use and rental income. Apartment A features 2B/2B, an open-concept living area overlooking canal, kitchen and dining space, Florida room, screened-in lanai, laundry, and a two-car garage. Previously owner-occupied, this unit is new to the short-term rental market. Apartment B offers 2B/1B, a kitchen, living and dining area, porch overlooking canal, laundry, and a private upstairs entrance located along the side of the garage. This unit has been operating as a short-term rental for a few years. Zoned R2 for weekly rentals, as stated in the property information, this furnished duplex presents an appealing opportunity for buyers seeking flexibility, rental potential, or the chance to create their own island getaway. The property also offers canal water views of Bimini Bay, with community boat slips available for lease through the City of Holmes Beach in the nearby T-end canals off Marina Drive between 72nd and 77th Streets. Boat slips are listed as available for $600 a year and can accommodate boats up to 23 feet. Enjoy the convenience of the free island trolley just steps away, making it easy to explore the island’s beaches, dining, shopping, and laid-back coastal atmosphere. Situated on a 8,792-square-foot lot, this property also offers the opportunity to renovate the existing duplex to suit your vision or explore the possibility of building your dream island home. Whether you envision a coastal investment, a personal vacation escape, or a property that combines both, this Holmes Beach duplex offers a rare opportunity to embrace the Anna Maria Island lifestyle.

4 Beds ⋅ 3 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code

Turnkey Coastal Duplex | Holmes Beach, Anna Maria Island A Rare Island Opportunity | Weekly Rental Potential Discover the charm of island living with this fully furnished duplex in the heart of Holmes Beach on beautiful Anna Maria Island. Just a short stroll from the beach, this versatile property offers an exceptional opportunity to enjoy the coastal lifestyle while exploring its rental potential. Featuring two separate residences with private entrances, the property offers a flexible layout ideal for an investment property, a vacation retreat, or a combination of personal use and rental income. Apartment A features 2B/2B, an open-concept living area overlooking canal, kitchen and dining space, Florida room, screened-in lanai, laundry, and a two-car garage. Previously owner-occupied, this unit is new to the short-term rental market. Apartment B offers 2B/1B, a kitchen, living and dining area, porch overlooking canal, laundry, and a private upstairs entrance located along the side of the garage. This unit has been operating as a short-term rental for a few years. Zoned R2 for weekly rentals, as stated in the property information, this furnished duplex presents an appealing opportunity for buyers seeking flexibility, rental potential, or the chance to create their own island getaway. The property also offers canal water views of Bimini Bay, with community boat slips available for lease through the City of Holmes Beach in the nearby T-end canals off Marina Drive between 72nd and 77th Streets. Boat slips are listed as available for $600 a year and can accommodate boats up to 23 feet. Enjoy the convenience of the free island trolley just steps away, making it easy to explore the island’s beaches, dining, shopping, and laid-back coastal atmosphere. Situated on a 8,792-square-foot lot, this property also offers the opportunity to renovate the existing duplex to suit your vision or explore the possibility of building your dream island home. Whether you envision a coastal investment, a personal vacation escape, or a property that combines both, this Holmes Beach duplex offers a rare opportunity to embrace the Anna Maria Island lifestyle.

7406 Marina Drive Unit A and B, Holmes Beach

$125,000

Live the ultimate island lifestyle with this rare opportunity to own a separately deeded boat slip in the heart of beautiful Holmes Beach on Anna Maria Island! This is the perfect, low-maintenance solution for local residents, off-water homeowners, or frequent visitors who want all the perks of the Florida boating lifestyle without the premium price tag or upkeep of a waterfront property. Skip the long lines at public ramps and the hassle of trailering; your gateway to the gulf is secure, permanent, and entirely yours. Nestled in Holmes Beach, you are minutes away from exploring the vibrant waters of Tampa Bay, navigating the Intracoastal Waterway, or cruising out into the wide-open Gulf. Holmes Beach is a coastal playground known for its sugary white sands, laid-back charm, and community-centered lifestyle. Owning your own slip unlocks everything that makes this town world-famous. Spend your mornings flats fishing for redfish, your afternoons sandbar-hopping at Passage Key, and your evenings treating family and friends to a true "dock-and-dine" experience at local waterfront restaurants.

Boat Slips SubDv. ⋅ 34217 Zip Code

Live the ultimate island lifestyle with this rare opportunity to own a separately deeded boat slip in the heart of beautiful Holmes Beach on Anna Maria Island! This is the perfect, low-maintenance solution for local residents, off-water homeowners, or frequent visitors who want all the perks of the Florida boating lifestyle without the premium price tag or upkeep of a waterfront property. Skip the long lines at public ramps and the hassle of trailering; your gateway to the gulf is secure, permanent, and entirely yours. Nestled in Holmes Beach, you are minutes away from exploring the vibrant waters of Tampa Bay, navigating the Intracoastal Waterway, or cruising out into the wide-open Gulf. Holmes Beach is a coastal playground known for its sugary white sands, laid-back charm, and community-centered lifestyle. Owning your own slip unlocks everything that makes this town world-famous. Spend your mornings flats fishing for redfish, your afternoons sandbar-hopping at Passage Key, and your evenings treating family and friends to a true "dock-and-dine" experience at local waterfront restaurants.

238 85th Street Unit 20, Holmes Beach

$899,000

Virtually Staged. Three-bedroom Anna Maria Island beach home, 300 steps to the island's world class beaches! This Holmes Beach retreat, located on Anna Maria Island, is ready and waiting for you! Discover this fully updated, bright and airy split plan, three-bedroom home spanning over 1,100 square feet under air as well as additional footage with carport and large screened in lanai. Thoughtfully designed with open living space combining the kitchen and living room areas. While still close to the beach, this home is located on a quiet cul-de-sac, yet far enough away from noisy Gulf Drive to be peaceful and sits right in the Island’s sweet spot between the Cortez and Manatee Bridges, providing easy access on and off the island. You’re just a short walk or golf cart ride away from white sandy beaches, restaurants, shops, and a convenient free trolley stop. You will see all properties were not created equal as you step into your own tropical, completely private backyard oasis with no neighbors to worry about peering into your life. Complete with screened in lanai, wet bar and highly sought after southern exposure. Bask in the sun, don't sit in the cold shadows with subpar exposure. Enjoy a beautiful, heated saltwater pool equipped with sprayers, fountains, and a sun platform for ultimate relaxation. A multilevel waterfall pond adds to the tranquil atmosphere, featuring a charming bridge that leads you over the pond directly to the gorgeous pool area. This expansive 9,000-square-foot lot is enhanced by landscaping stones, providing ease of maintenance. The home features a metal roof and impact windows for peace of mind. It boasts 2025 appliances, including a washer and dryer, along with all-new cabinetry and quartz countertops in both the kitchen and master bath. Fresh paint and 5-inch base molding through-out complete the modern look and feel. This property is offered turnkey furnished and is rental ready for monthly stays. RV and boat parking allowed! There is nothing to do here but relax and enjoy your surroundings: take a dip in the pool, stroll to the beach, indulge in the varied dining options from tiki bars to fine dining. Enjoy the manatees and dolphins playing in the canal across the street and parrots flying overhead! Immerse yourself in all the serenity and joys this beautiful island has to offer. Whether you’re seeking relaxation or adventure, this home provides the perfect base for enjoying Anna Maria Island’s unique charm and vibrant lifestyle. All NEW in 2025, Washer, Dryer, Refrigerator, Range, Dishwasher, Microwave, High Velocity Range Hood, Pool Heater, Pool Pump, Water Heater, Kitchen Cabinets and Quartz Countertops, Master Bath Cabinets and Quartz Countertop, Guest Bathroom with New Vanity and Top, All Furniture and Bedding. Impact Windows installed 2021 and 2022, Metal Roof installed 2018. Owner financing possible.

3 Beds ⋅ 2 Baths ⋅ Sunrise Park SubDv. ⋅ 34217 Zip Code

Virtually Staged. Three-bedroom Anna Maria Island beach home, 300 steps to the island's world class beaches! This Holmes Beach retreat, located on Anna Maria Island, is ready and waiting for you! Discover this fully updated, bright and airy split plan, three-bedroom home spanning over 1,100 square feet under air as well as additional footage with carport and large screened in lanai. Thoughtfully designed with open living space combining the kitchen and living room areas. While still close to the beach, this home is located on a quiet cul-de-sac, yet far enough away from noisy Gulf Drive to be peaceful and sits right in the Island’s sweet spot between the Cortez and Manatee Bridges, providing easy access on and off the island. You’re just a short walk or golf cart ride away from white sandy beaches, restaurants, shops, and a convenient free trolley stop. You will see all properties were not created equal as you step into your own tropical, completely private backyard oasis with no neighbors to worry about peering into your life. Complete with screened in lanai, wet bar and highly sought after southern exposure. Bask in the sun, don't sit in the cold shadows with subpar exposure. Enjoy a beautiful, heated saltwater pool equipped with sprayers, fountains, and a sun platform for ultimate relaxation. A multilevel waterfall pond adds to the tranquil atmosphere, featuring a charming bridge that leads you over the pond directly to the gorgeous pool area. This expansive 9,000-square-foot lot is enhanced by landscaping stones, providing ease of maintenance. The home features a metal roof and impact windows for peace of mind. It boasts 2025 appliances, including a washer and dryer, along with all-new cabinetry and quartz countertops in both the kitchen and master bath. Fresh paint and 5-inch base molding through-out complete the modern look and feel. This property is offered turnkey furnished and is rental ready for monthly stays. RV and boat parking allowed! There is nothing to do here but relax and enjoy your surroundings: take a dip in the pool, stroll to the beach, indulge in the varied dining options from tiki bars to fine dining. Enjoy the manatees and dolphins playing in the canal across the street and parrots flying overhead! Immerse yourself in all the serenity and joys this beautiful island has to offer. Whether you’re seeking relaxation or adventure, this home provides the perfect base for enjoying Anna Maria Island’s unique charm and vibrant lifestyle. All NEW in 2025, Washer, Dryer, Refrigerator, Range, Dishwasher, Microwave, High Velocity Range Hood, Pool Heater, Pool Pump, Water Heater, Kitchen Cabinets and Quartz Countertops, Master Bath Cabinets and Quartz Countertop, Guest Bathroom with New Vanity and Top, All Furniture and Bedding. Impact Windows installed 2021 and 2022, Metal Roof installed 2018. Owner financing possible.

503 Bayview Drive, Holmes Beach

$1,200,000

Pool. Porch. Solar. Island. Welcome to 264 S Harbor Dr, where the Anna Maria Island lifestyle comes standard. Step out back and it’s all there: a sparkling private pool framed by a paver deck, a fully fenced yard, and a covered upper-level porch made for coffee at sunrise and sunsets with a view of the sky. This is the Florida outdoor space folks dream about, and it’s already built, finished and ready to enjoy. This elevated 3-bedroom, 2-bath home is bright, airy and move-in ready. Recently updated flooring flows throughout, the bathrooms have been refreshed, and the kitchen features stone countertops and a large center island with plenty of room to gather. The covered porch extends your living space outdoors, giving you a spot to relax in nearly any weather. Rooftop solar panels help keep energy costs in check, a smart upgrade you’ll appreciate month after month. Two-car garage / ground-level storage gives you room for bikes, paddleboards, beach chairs and everything else that comes with island life. And then there’s the location. You’re in the heart of Holmes Beach, a short bike ride from gorgeous sand, with island restaurants, coffee shops and sunset spots close by. S Harbor Dr neighbors have access to a nearby boat ramp, so Gulf and bay adventures are never far away. Whether you’re picturing a full-time island home or a seasonal retreat, this one puts the pool, the porch, the solar and the location all in one package. The photos show the details. The feeling of walking in is something you have to experience. Come see what everyone’s been missing. Schedule your private showing today.

3 Beds ⋅ 2 Baths ⋅ Sportsmans Harbor SubDv. ⋅ 34217 Zip Code

Pool. Porch. Solar. Island. Welcome to 264 S Harbor Dr, where the Anna Maria Island lifestyle comes standard. Step out back and it’s all there: a sparkling private pool framed by a paver deck, a fully fenced yard, and a covered upper-level porch made for coffee at sunrise and sunsets with a view of the sky. This is the Florida outdoor space folks dream about, and it’s already built, finished and ready to enjoy. This elevated 3-bedroom, 2-bath home is bright, airy and move-in ready. Recently updated flooring flows throughout, the bathrooms have been refreshed, and the kitchen features stone countertops and a large center island with plenty of room to gather. The covered porch extends your living space outdoors, giving you a spot to relax in nearly any weather. Rooftop solar panels help keep energy costs in check, a smart upgrade you’ll appreciate month after month. Two-car garage / ground-level storage gives you room for bikes, paddleboards, beach chairs and everything else that comes with island life. And then there’s the location. You’re in the heart of Holmes Beach, a short bike ride from gorgeous sand, with island restaurants, coffee shops and sunset spots close by. S Harbor Dr neighbors have access to a nearby boat ramp, so Gulf and bay adventures are never far away. Whether you’re picturing a full-time island home or a seasonal retreat, this one puts the pool, the porch, the solar and the location all in one package. The photos show the details. The feeling of walking in is something you have to experience. Come see what everyone’s been missing. Schedule your private showing today.

264 S Harbor Drive, Holmes Beach

$189,000

Priced to sell. 2 adjacent vacant lots with combined area of 0.42 acres in Holmes Beach on Anna Maria Island. This land is located next to serene Grassy Point Preserve, steps from the beach, in sought-after neighborhoods on the island. It offers easy access to local shops and dinning. Perfect opportunity for developer or investor.

Ilexhurst SubDv. ⋅ 34217 Zip Code

Priced to sell. 2 adjacent vacant lots with combined area of 0.42 acres in Holmes Beach on Anna Maria Island. This land is located next to serene Grassy Point Preserve, steps from the beach, in sought-after neighborhoods on the island. It offers easy access to local shops and dinning. Perfect opportunity for developer or investor.

3015 Avenue B, Holmes Beach

$1,650,000

Exceptional Investment Opportunity Just Two Blocks from the Beach! Welcome to 400 75th Street in Holmes Beach, a turnkey full duplex offering the perfect combination of income potential and laid-back Anna Maria Island living. This property features two spacious 2-bedroom, 2-bathroom units, each with its own private heated saltwater pool, creating an ideal setup for vacation rentals, multi-generational living, or an owner-occupant looking to generate income from the second unit. Designed with vacationers in mind, each residence features its own indoor laundry room, private outdoor shower, and inviting outdoor living and pool area—everything guests need after a day at the beach. Best of all, you're located just two blocks from public beach access, putting the turquoise waters and white-sand beaches of Anna Maria Island within an easy stroll. Located in a weekly short-term rental zone, this property is already a proven income producer, generating more than $135,000 in rental revenue. It is being offered turnkey furnished, allowing the next owner to step into an established island rental property with minimal setup. Adding even more value to this unique opportunity, the property may also have access to rent a boat slip through the City of Holmes Beach, subject to City availability and requirements—an incredible perk for boaters looking to enjoy the surrounding waterways and Gulf Coast lifestyle. Whether you're searching for a high-performing vacation rental, a beach retreat with income potential, or the flexibility to use one side while renting the other, 400 75th Street offers a rare opportunity to own two private pool residences just steps from the beach in the heart of Holmes Beach.

4 Beds ⋅ 4 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code

Exceptional Investment Opportunity Just Two Blocks from the Beach! Welcome to 400 75th Street in Holmes Beach, a turnkey full duplex offering the perfect combination of income potential and laid-back Anna Maria Island living. This property features two spacious 2-bedroom, 2-bathroom units, each with its own private heated saltwater pool, creating an ideal setup for vacation rentals, multi-generational living, or an owner-occupant looking to generate income from the second unit. Designed with vacationers in mind, each residence features its own indoor laundry room, private outdoor shower, and inviting outdoor living and pool area—everything guests need after a day at the beach. Best of all, you're located just two blocks from public beach access, putting the turquoise waters and white-sand beaches of Anna Maria Island within an easy stroll. Located in a weekly short-term rental zone, this property is already a proven income producer, generating more than $135,000 in rental revenue. It is being offered turnkey furnished, allowing the next owner to step into an established island rental property with minimal setup. Adding even more value to this unique opportunity, the property may also have access to rent a boat slip through the City of Holmes Beach, subject to City availability and requirements—an incredible perk for boaters looking to enjoy the surrounding waterways and Gulf Coast lifestyle. Whether you're searching for a high-performing vacation rental, a beach retreat with income potential, or the flexibility to use one side while renting the other, 400 75th Street offers a rare opportunity to own two private pool residences just steps from the beach in the heart of Holmes Beach.

400 75th Street, Holmes Beach

$4,925,000

One of a kind, 8,574 sq ft three floor building with parking for more than 30 vehicles. The 15,000 sq ft lot is zoned C3 which is the most intensive commercial district in Holmes Beach City, FL. It is a perfect central location on Anna Maria Island and just a few blocks from Manatee Ave. Each floor has a lobby area equipped with male and female restrooms in addition to two (2) interior egress stairwells. The all-concrete block building is equipped with a hydraulic oversized 3,500 lb capacity elevator which fits a standard pallet for ease of storage transportation above the ground level. The building has 3 Phase electrical power as well as oversized county water and sewer lines, natural gas and dumpster enclosure. Unique lot configuration allows for parking on three sides of the building with a pass-through alley on the South side of the property for ease of vendor, maintenance or large vehicle support. Ground level supports professional laundry operation with water pit and elevated washer pad with extra high open ceilings. One garage bay on the West side with an additional garage door on the East side to facilitate large item transport. Ground level floor includes concrete work to accept a 4’ X 4’ laundry scale flush with the polished concrete floor. Second floor contains several offices as well as electrical, plumbing and mechanical for residential washers, dryers and laundry sink. Extra high open ceilings all throughout the second floor as well. Third level equipped with cubicles, large break room and kitchen, conference room, server room, key storage lockable area as well as a stand-alone office. This is a perfect industrial building to support all facets of a service business to the barrier islands of Anna Maria Island, Longboat Key and beyond. The design of the property facilitates one occupant or several occupants if multiple tenancy is a goal. Every detail has been considered at time of build and built by local Anna Maria Island contractor. Washers, Dryers, laundry carts, scale not included. This property is NOT to be considered a turnkey office. Note, listing agent as well as broker have ownership interest in property.

Ilexhurst SubDv. ⋅ 34217 Zip Code

One of a kind, 8,574 sq ft three floor building with parking for more than 30 vehicles. The 15,000 sq ft lot is zoned C3 which is the most intensive commercial district in Holmes Beach City, FL. It is a perfect central location on Anna Maria Island and just a few blocks from Manatee Ave. Each floor has a lobby area equipped with male and female restrooms in addition to two (2) interior egress stairwells. The all-concrete block building is equipped with a hydraulic oversized 3,500 lb capacity elevator which fits a standard pallet for ease of storage transportation above the ground level. The building has 3 Phase electrical power as well as oversized county water and sewer lines, natural gas and dumpster enclosure. Unique lot configuration allows for parking on three sides of the building with a pass-through alley on the South side of the property for ease of vendor, maintenance or large vehicle support. Ground level supports professional laundry operation with water pit and elevated washer pad with extra high open ceilings. One garage bay on the West side with an additional garage door on the East side to facilitate large item transport. Ground level floor includes concrete work to accept a 4’ X 4’ laundry scale flush with the polished concrete floor. Second floor contains several offices as well as electrical, plumbing and mechanical for residential washers, dryers and laundry sink. Extra high open ceilings all throughout the second floor as well. Third level equipped with cubicles, large break room and kitchen, conference room, server room, key storage lockable area as well as a stand-alone office. This is a perfect industrial building to support all facets of a service business to the barrier islands of Anna Maria Island, Longboat Key and beyond. The design of the property facilitates one occupant or several occupants if multiple tenancy is a goal. Every detail has been considered at time of build and built by local Anna Maria Island contractor. Washers, Dryers, laundry carts, scale not included. This property is NOT to be considered a turnkey office. Note, listing agent as well as broker have ownership interest in property.

3004 Avenue C, Holmes Beach

$895,000

Resort-style, maintenance-free living awaits just steps from the beach on Anna Maria Island, where this beautifully renovated residence offers the perfect blend of luxury, privacy, and effortless coastal living. Set within an intimate community of only six residences, this exceptional 2-bedroom, 2-bath ground-floor retreat showcases charming Key West-inspired architecture by Emily Anne Smith and stands out with its own private tropical courtyard. Inside, the home feels bright, open, and beautifully finished, with vaulted ceilings, crown molding, designer light fixtures, stylish furnishings, and an easy-flowing floor plan designed for both everyday living and entertaining. The beautifully updated kitchen features crisp white cabinetry, quartz countertops, stainless steel appliances, and a generous breakfast bar that opens to the main living space, creating a natural gathering place for family and guests. Both bathrooms have also been thoughtfully renovated with quartz countertops and fresh, upscale finishes that continue the home’s polished coastal aesthetic. Offered turnkey furnished, every detail has been considered so you can begin enjoying the island lifestyle from the moment you arrive. The private outdoor spaces are equally special, with lush tropical landscaping, a peaceful courtyard, private lanai, and outdoor shower creating your own secluded island oasis. Just outside your door, enjoy resort-style amenities including a lagoon-style pool with a waterfall and a tiki hut, all shared by only six residences for a quiet and relaxed atmosphere. Ownership is designed to be easy, so you can spend more time enjoying the island and less time worrying about upkeep. Weekly rentals are permitted, and the property has a successful history as a vacation rental, offering excellent flexibility for personal use, investment, or both. The community is also pet friendly. The location is everything. Anna Maria Island is loved for its sugar-sand beaches, turquoise Gulf waters, unforgettable sunsets, charming shops, locally owned restaurants, and laid-back Old Florida character. With the beach just steps away, morning walks, sunset swims, paddleboarding, beach days, and evenings by the Gulf can become part of everyday life. Whether you are searching for a full-time island residence, seasonal escape, or proven vacation rental, this property offers an exceptional combination of location, privacy, convenience, style, and lifestyle. Ground-floor living, beautifully renovated interiors, private tropical outdoor space, resort-style amenities, turnkey furnishings, weekly rental flexibility, and incredible proximity to the beach make this one of the most desirable opportunities in this charming boutique community.

2 Beds ⋅ 2 Baths ⋅ The Blue Lagoon SubDv. ⋅ 34217 Zip Code

Resort-style, maintenance-free living awaits just steps from the beach on Anna Maria Island, where this beautifully renovated residence offers the perfect blend of luxury, privacy, and effortless coastal living. Set within an intimate community of only six residences, this exceptional 2-bedroom, 2-bath ground-floor retreat showcases charming Key West-inspired architecture by Emily Anne Smith and stands out with its own private tropical courtyard. Inside, the home feels bright, open, and beautifully finished, with vaulted ceilings, crown molding, designer light fixtures, stylish furnishings, and an easy-flowing floor plan designed for both everyday living and entertaining. The beautifully updated kitchen features crisp white cabinetry, quartz countertops, stainless steel appliances, and a generous breakfast bar that opens to the main living space, creating a natural gathering place for family and guests. Both bathrooms have also been thoughtfully renovated with quartz countertops and fresh, upscale finishes that continue the home’s polished coastal aesthetic. Offered turnkey furnished, every detail has been considered so you can begin enjoying the island lifestyle from the moment you arrive. The private outdoor spaces are equally special, with lush tropical landscaping, a peaceful courtyard, private lanai, and outdoor shower creating your own secluded island oasis. Just outside your door, enjoy resort-style amenities including a lagoon-style pool with a waterfall and a tiki hut, all shared by only six residences for a quiet and relaxed atmosphere. Ownership is designed to be easy, so you can spend more time enjoying the island and less time worrying about upkeep. Weekly rentals are permitted, and the property has a successful history as a vacation rental, offering excellent flexibility for personal use, investment, or both. The community is also pet friendly. The location is everything. Anna Maria Island is loved for its sugar-sand beaches, turquoise Gulf waters, unforgettable sunsets, charming shops, locally owned restaurants, and laid-back Old Florida character. With the beach just steps away, morning walks, sunset swims, paddleboarding, beach days, and evenings by the Gulf can become part of everyday life. Whether you are searching for a full-time island residence, seasonal escape, or proven vacation rental, this property offers an exceptional combination of location, privacy, convenience, style, and lifestyle. Ground-floor living, beautifully renovated interiors, private tropical outdoor space, resort-style amenities, turnkey furnishings, weekly rental flexibility, and incredible proximity to the beach make this one of the most desirable opportunities in this charming boutique community.

215 67th Street Unit 6, Holmes Beach

5325 Marina Drive Unit 423, Holmes Beach

$350,000

“Exceptional Buying Opportunity,” at the Waterline Villas & Marina Residences. The Autograph Collection Residences are a sophisticated and stylish boutique hotel with 37 fully TURN-KEY furnished condos with a premier waterfront location on Anna Maria Island. 45’, BOAT SLIPS ARE free to use for owners while in residence!!! Built in 2017 all units feature 2 bedrooms, 2 full baths, a gourmet kitchen, separate living area and its own washer & dryer. Unit #423 is located in the southernmost "ISLAND" building detached from the main hotel that allows for more privacy. Owners have access to a boat slip while they are in residence. Nightly rentals can be easily handled by the on-site property management company Mainsail Lodging & Development, an award winning hospitality organization headquartered in Tampa. Enjoy the laid-back, Old Florida feel of Anna Maria Island. Park your car on-site and take the free trolley to explore everything the island has to offer. Waterline amenities include a graceful lobby with front desk, on-site management to assist with guest needs, heated resort-style pool with sun deck overlooking 50-slip marina that accommodates boats up to 45’, boat slips available (free for owners while in residence), on site fabulous "Chateau Anna Maria" restaurant and bar, charter boats for fishing and Eco tours, bicycles, paddle board, and kayaks free for owners, 24 hour fitness center, elegant ballroom for weddings, corporate gatherings, gift shop, complimentary Wi-Fi, Housekeeping and Concierge services. Zoning allows owners to stay in their units up to 120 days per calendar year and the dates do not have to be consecutive. Experience the dream of owning property on Anna Maria Island without the worry associated with management and maintenance!

2 Beds ⋅ 2 Baths ⋅ Waterline Villas & Marina SubDv. ⋅ 34217 Zip Code

“Exceptional Buying Opportunity,” at the Waterline Villas & Marina Residences. The Autograph Collection Residences are a sophisticated and stylish boutique hotel with 37 fully TURN-KEY furnished condos with a premier waterfront location on Anna Maria Island. 45’, BOAT SLIPS ARE free to use for owners while in residence!!! Built in 2017 all units feature 2 bedrooms, 2 full baths, a gourmet kitchen, separate living area and its own washer & dryer. Unit #423 is located in the southernmost "ISLAND" building detached from the main hotel that allows for more privacy. Owners have access to a boat slip while they are in residence. Nightly rentals can be easily handled by the on-site property management company Mainsail Lodging & Development, an award winning hospitality organization headquartered in Tampa. Enjoy the laid-back, Old Florida feel of Anna Maria Island. Park your car on-site and take the free trolley to explore everything the island has to offer. Waterline amenities include a graceful lobby with front desk, on-site management to assist with guest needs, heated resort-style pool with sun deck overlooking 50-slip marina that accommodates boats up to 45’, boat slips available (free for owners while in residence), on site fabulous "Chateau Anna Maria" restaurant and bar, charter boats for fishing and Eco tours, bicycles, paddle board, and kayaks free for owners, 24 hour fitness center, elegant ballroom for weddings, corporate gatherings, gift shop, complimentary Wi-Fi, Housekeeping and Concierge services. Zoning allows owners to stay in their units up to 120 days per calendar year and the dates do not have to be consecutive. Experience the dream of owning property on Anna Maria Island without the worry associated with management and maintenance!

5325 Marina Drive Unit 423, Holmes Beach

$2,300,000

A Gulf-front condo on Anna Maria Island where the investment and the lifestyle work together. This 3-bedroom, 2-bath fully furnished condo in Holmes Beach sits directly on the sugar-sand beach, with panoramic Gulf views, dolphins passing by, and sunsets from your private covered balcony that guests and owners remember long after they leave. Short-term rentals are allowed, so you can welcome vacationers while you're away and keep the Gulf for yourself and your loved ones when you're here. Expansive sliders showcase beautiful Gulf views, while the boutique beachfront community offers a heated Gulf-front pool, sun deck, tennis court, and lush tropical courtyard. The free Anna Maria Island Trolley connects you to Bean Point, Pine Avenue, the City Pier, and Bridge Street, with island cafés, waterfront dining, shops, and bike paths minutes away. Gulf-front properties with this location and these amenities rarely come available, whether you're looking for a vacation rental investment, a seasonal retreat, or a full-time home where every day feels like a getaway.

3 Beds ⋅ 2 Baths ⋅ Gulfplace SubDv. ⋅ 34217 Zip Code

A Gulf-front condo on Anna Maria Island where the investment and the lifestyle work together. This 3-bedroom, 2-bath fully furnished condo in Holmes Beach sits directly on the sugar-sand beach, with panoramic Gulf views, dolphins passing by, and sunsets from your private covered balcony that guests and owners remember long after they leave. Short-term rentals are allowed, so you can welcome vacationers while you're away and keep the Gulf for yourself and your loved ones when you're here. Expansive sliders showcase beautiful Gulf views, while the boutique beachfront community offers a heated Gulf-front pool, sun deck, tennis court, and lush tropical courtyard. The free Anna Maria Island Trolley connects you to Bean Point, Pine Avenue, the City Pier, and Bridge Street, with island cafés, waterfront dining, shops, and bike paths minutes away. Gulf-front properties with this location and these amenities rarely come available, whether you're looking for a vacation rental investment, a seasonal retreat, or a full-time home where every day feels like a getaway.

6700 Gulf Drive Unit B8, Holmes Beach

$709,000

Salt air, swaying palms and the Gulf at your doorstep. This 2-bedroom, 2-bath condo at Martinique South in the heart of Holmes Beach captures the easy rhythm of island life. Start your morning on the enclosed porch with coffee in hand and glimpses of turquoise water through the palms. It's an easy place to unwind any time of day. Inside, the open layout flows from the kitchen to the dining and living areas, made for relaxed everyday living and easy entertaining. The kitchen has granite countertops, generous cabinetry and plenty of room to prep. An in-unit washer and dryer and a new A/C installed in 2026 add comfort and peace of mind. Then there's the storage, a rare find on the island. A private garage gives you your own secure space to park, plus room for kayaks, paddleboards, bikes and fishing gear. Three more storage units hold the beach chairs, umbrellas and seasonal extras, so your condo stays clean, clutter-free and ready to enjoy. Step outside to the community's Gulf-front pool, clubhouse and tennis court, or follow the direct beach access to the sugar-sand shoreline just steps away. Make it your full-time island home or a laid-back weekend escape. This is coastal living with room for it all, on Anna Maria Island.

2 Beds ⋅ 2 Baths ⋅ Martinique Condo SubDv. ⋅ 34217 Zip Code

Salt air, swaying palms and the Gulf at your doorstep. This 2-bedroom, 2-bath condo at Martinique South in the heart of Holmes Beach captures the easy rhythm of island life. Start your morning on the enclosed porch with coffee in hand and glimpses of turquoise water through the palms. It's an easy place to unwind any time of day. Inside, the open layout flows from the kitchen to the dining and living areas, made for relaxed everyday living and easy entertaining. The kitchen has granite countertops, generous cabinetry and plenty of room to prep. An in-unit washer and dryer and a new A/C installed in 2026 add comfort and peace of mind. Then there's the storage, a rare find on the island. A private garage gives you your own secure space to park, plus room for kayaks, paddleboards, bikes and fishing gear. Three more storage units hold the beach chairs, umbrellas and seasonal extras, so your condo stays clean, clutter-free and ready to enjoy. Step outside to the community's Gulf-front pool, clubhouse and tennis court, or follow the direct beach access to the sugar-sand shoreline just steps away. Make it your full-time island home or a laid-back weekend escape. This is coastal living with room for it all, on Anna Maria Island.

5200 Gulf Drive Unit 107, Holmes Beach

How much is your home worth?

How much is your home worth?