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705 Key Royale Drive, Holmes Beach
$3,900,000
4 Beds ⋅ 5 Baths ⋅ Key Royale SubDv. ⋅ 34217 Zip Code
Under contract-accepting backup offers. A distinctive bayfront residence with extraordinary possibilities on Key Royale, one of Anna Maria Island's most desirable waterfront neighborhoods. Situated on one-third of an acre with 100 feet of direct, deep-water Tampa Bay frontage, this exceptional property offers sweeping views toward the Sunshine Skyway Bridge, spectacular evening colors reflected across the bay and beautiful western sunsets enjoyed from the new private dock. Across the street, the lush greens of Key Royale Golf Club complete a setting that beautifully combines waterfront and golf course living. Offering 4200 square feet, the existing residence features four bedrooms, four full and two half baths, soaring cathedral ceilings, spacious living and dining areas and a flexible floor plan with generous opportunities for renovation and personalization. Expansive windows and multiple outdoor living areas take advantage of the waterfront surroundings, while the home's generous proportions provide a wonderful foundation for creating a distinctive island retreat. Outdoor features include a 20-by-45-foot swimming pool, a new seawall (2025) and a private dock (2025) with direct access to Tampa Bay. The setting invites boating, entertaining and enjoying the constantly changing waterfront scenery, which includes tarpon, dolphins and manatees. The property experienced water intrusion during the 2024 hurricane and was remediated. Some repairs have been made, offering an opportunity for thoughtful renovation and updates, subject to applicable FEMA and City of Holmes Beach requirements, permits and approvals. Alternatively, the exceptional homesite presents an opportunity to create an entirely new custom waterfront estate tailored to its remarkable views and island setting. Located in the established Key Royale community, just minutes from Anna Maria Island's beautiful Gulf beaches, restaurants and boutiques, this property offers a rare combination of substantial existing living space, exceptional waterfront frontage, golf-course surroundings and future possibilities. Whether beautifully reimagined or newly created, this is an opportunity to enjoy the very best of Anna Maria Island waterfront living.

705 Key Royale Drive, Holmes Beach
705 Key Royale Drive, Holmes Beach
$3,900,000
Key Royale SubDv. ⋅ 34217 Zip Code
Under contract-accepting backup offers. An exceptional opportunity to create your dream waterfront estate on Key Royale, one of Anna Maria Island's most desirable residential neighborhoods. Set on approximately one-third of an acre with 100 feet of direct Tampa Bay, deep water frontage, this remarkable property offers sweeping water views, the distant silhouette of the Sunshine Skyway Bridge and spectacular, colorful sunsets that transform the bay into a breathtaking backdrop. Across the street, the lush greens of Key Royale Golf Club provide an equally appealing setting, creating a rare combination of waterfront beauty and golf course living. Imagine designing a custom coastal residence that takes full advantage of the expansive bayfront setting, with generous outdoor living areas, a resort-style pool and thoughtfully positioned spaces to capture the remarkable views. The existing property features a new seawall (2025) and private dock (2025), providing convenient access to the surrounding waterways and the boating lifestyle for which Anna Maria Island is known. Located in the established Key Royale community, this exceptional homesite is just minutes from Anna Maria Island's beautiful Gulf beaches, waterfront restaurants, charming boutiques and relaxed island attractions. An existing residence occupies the property and offers the alternative of renovation, although the setting presents an extraordinary opportunity for new construction. With its generous waterfront frontage, golf-course surroundings and captivating sunsets over Tampa Bay, this is a rare opportunity to create a lasting island retreat in a truly special location.

705 Key Royale Drive, Holmes Beach
6300 Flotilla Drive Unit 96, Holmes Beach
$399,000
2 Beds ⋅ 2 Baths ⋅ Shell Point SubDv. ⋅ 34217 Zip Code
Under contract-accepting backup offers. Welcome to Shell Point, a peaceful and highly desirable waterfront community nestled along Watson’s Bayou and Anna Maria Sound on Anna Maria Island! This beautifully renovated 2-bedroom, 2-bath condo offers a bright, inviting interior with an open-concept layout designed for comfortable coastal living. The updated kitchen is light and airy, featuring charming peek-a-boo views of the bay from the kitchen window. The spacious living and dining area flows seamlessly into the enclosed lanai, where the sliding doors have been removed to create additional living space and greater flexibility for relaxing, entertaining, or creating your own cozy retreat. The generously sized primary suite features a private en-suite bathroom, while the spacious second bedroom is conveniently located near the hallway guest bath. Offered partially furnished, this condo provides a wonderful head start on creating your own island getaway. Select listing photos have been virtually staged to showcase the condo's full potential and help buyers envision how beautifully these spaces can be transformed with light, bright coastal furnishings and décor. Shell Point offers a true resort-style lifestyle with a refreshing community pool, tennis and pickleball courts, shuffleboard, a putting green, kayak storage, and beautifully maintained grounds. One of the community’s most cherished traditions is gathering with neighbors along the waterfront to enjoy Anna Maria Island’s spectacular sunsets. Known for its welcoming atmosphere and tranquil waterfront setting, Shell Point is tucked away in a quieter section of Holmes Beach, yet just a short stroll from the island’s beautiful beaches, local shops, restaurants, and entertainment. Monthly rentals are permitted, offering flexibility for those who may not use their island retreat year-round, and pets are welcome for owners! Whether you're searching for a full-time residence, seasonal escape, or investment opportunity, this beautifully updated condo offers an exceptional opportunity to enjoy the Anna Maria Island lifestyle at an attractive price point. Your affordable piece of paradise awaits!

6300 Flotilla Drive Unit 96, Holmes Beach
3100 Gulf Drive Unit 2, Holmes Beach
$549,000
2 Beds ⋅ 2 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code
Under contract-accepting backup offers. Welcome to Your Income-Producing Slice of Paradise in Holmes Beach! Discover the perfect blend of beachside living and investment potential with this elevated, multi-level 2-bedroom, 2-bathroom condo in one of Florida’s most desirable beach destinations. Ideally suited for vacation rental use, this property offers an appealing opportunity for investors seeking a property in the sought-after Anna Maria Island market. Designed with both owners and guests in mind, the main living level features an open-concept layout that creates a welcoming space for relaxing and entertaining after a day at the beach. A full bathroom on the main level adds convenience, while the upper level offers two bedrooms and a second full bathroom, providing a comfortable separation between living and sleeping spaces—an attractive feature for vacationing couples and families alike. Just moments from the beautiful Gulf beaches, guests can enjoy the island’s sandy shores, sparkling waters, and unforgettable sunsets. Shopping, dining, and local attractions are also conveniently nearby, making it easy to experience everything Anna Maria Island has available. Enjoy peace of mind with numerous recent updates and improvements, offering a refreshed, move-in-ready experience for the next owner. RECENT IMPROVEMENTS INCLUDE: New Roof: 2024 LVP Flooring: 2022 Interior Paint: 2025 Refrigerator & Range: 2025 Dishwasher: 2026 New Pool Equipment: 2024 Pool Refinishing: 2026 Updated Kitchen & Bathroom Countertops: 2026 Full-Size Washer & Dryer: 2026 Water Heater: 2025 Elevated construction offers added peace of mind against interior flooding. The condo unit has sustained no hurricane damage. Whether you’re looking to expand your investment portfolio, establish a vacation getaway, or enjoy a combination of personal use and rental income, this Holmes Beach condo offers an appealing opportunity to own a piece of island paradise.

3100 Gulf Drive Unit 2, Holmes Beach
4006 5th Avenue, Holmes Beach
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 4th Avenue Condominium SubDv. ⋅ 34217 Zip Code
Check out "La Isla Bonita"on Holmes Beach! A successful vacation rental property just 5 minutes (400 steps) to the gorgeous Anna Maria Island beaches! This concrete block construction has a total of 3515 total sq.ft. This contemporary QUALITY BUILT home in 2006 with an ELEVATOR has 4 bedrooms/4 baths ENSUITE. Brand new METAL AND FLAT ROOF 2026. TURN-KEY FURNISHED. WEEKLY RENTALS. Private gated heated swimming pool with a game room attached to the garage. Partial Gulf views from the balcony! 2 NEW AC Units in 2020, New pool heater in 2023. New pool pump in 2025. This LOCATION cannot be beat just less than 400 steps to the white sandy beach or to the free trolley service that will take you from one end of the island to the other. Across the street is walking distance to the Publix grocery AND liquor store, CVS drug store and pharmacy, beach shops and cool island restaurants. Anna Maria Island Beach Café and SKINNY'S Burgers is just across the street with a tiki bar, ice cream, snow cones, restaurant and bands every night till sunset. Take the stairs or the elevator to the terrace that has views of the surrounding island and glimpses of the gulf! Enjoy an evening cocktail while catching one of the amazing sunsets that Anna Maria is famous for!

4006 5th Avenue, Holmes Beach
120 52nd Street, Holmes Beach
$699,000
2 Beds ⋅ 2 Baths ⋅ 34217 Zip Code
Under contract-accepting backup offers. Short Sale. Live a life you don't need a vacation from in this beautifully updated, turnkey-furnished beach villa just STEPS from the sugar-sand beaches of the Gulf. Located on the desirable west side of Holmes Beach, this charming 2-bedroom, 1.5-bath townhouse offers approximately 1,050 sq ft of coastal living with no major roads to cross on your way to the beach. Recently renovated, this home features a stunning new kitchen completed in 2025 with custom cabinetry, granite countertops, and state-of-the-art stainless-steel appliances. Fresh interior paint, new tile flooring throughout, and hardwood stairs create a clean, modern feel with no carpeting to maintain. Additional updates include a NEW ROOF IN 2024 & an A/C SYSTEM INSTALLED IN 2020. Enjoy your morning coffee in the inviting front seating area or unwind in the private fenced courtyard, perfect for grilling, entertaining, or relaxing after a day at the beach. With no condo fees, excellent rental potential, and a prime location just moments from shopping, dining, and everything that makes Holmes Beach exceptional, this property presents an exceptional opportunity as a vacation getaway, investment property, or year-round residence. *** SELLER offering $10,000 credit towards closing costs on an agreed upon contract.

120 52nd Street, Holmes Beach
2811 Avenue C, Holmes Beach
$1,099,000
2 Beds ⋅ 2 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code
Your PERFECT BEACH HOUSE awaits on Anna Maria Island! Just 2 blocks to the gorgeous Gulf and 1 block to the beautiful Bay, this beautifully updated & elevated 2-bedroom, 2-bath ++ coastal retreat delivers the ultimate in relaxed island living. Thoughtfully renovated, this cozy gem features wood flooring throughout, an open-concept layout, and a super spacious chef's kitchen complete with stainless appliances and sleek quartz countertops. The primary suite is complete with a large walk-in closet and private ensuite bathroom. The 2nd bedroom has an extended walk-in closet for additional storage. Step outside to a newer expansive front deck and experience the rare opportunity to take in both sunrise and AMI's famous sunset skies. Your outdoor private tropical oasis features a sparkling, travertine-lined heated pool, a generous entertaining space, and cozy screened lanai perfect for afternoon relaxation. Enjoy peaceful surroundings as the property is ideally positioned adjacent to a nature preserve. A big ++ is the bonus non-conforming flex space on the first level. It features private entrances from the screened patio and includes two large rooms, one with a wet bar, and a full bath. Ideal for guests, extended stays, or a separate creative retreat. This truly lovely beach home comes furnished so just pack your bags, it is completely move-in ready! Use as a full-time residence, second home and/or take advantage of the rental income opportunity, located in a 30-day rental zone. Additional highlights include a spacious 2-car garage with ample storage, and a gated entry for added privacy. The newer metal roof, elevated air conditioner & mini splits along with impact windows and doors give additional peace of mind. Perfectly located mid-island with easy access to shops, dining, and the best of Anna Maria Island, this is your chance to own a true SLICE OF PARADISE. Island living doesn’t get better than this!

2811 Avenue C, Holmes Beach
518 58th Street, Holmes Beach
$3,250,000
4 Beds ⋅ 6 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
Under contract-accepting backup offers. Virtually Staged. Imagine arriving at a private estate tucked along the shimmering waters of Tampa Bay on Anna Maria Island, where 235 feet of pristine waterfront create a rare sense of space, privacy and uninterrupted views. This four-bedroom, six-bath coastal residence in Holmes Beach is designed to capture the beauty of the bay from nearly every angle. Expansive walls of glass and sliding doors frame panoramic water vistas, filling the home with natural light and bringing the outdoors in, a hallmark of luxury waterfront homes in this area. Inside, the home blends refined elegance with relaxed island living. A grand open-concept layout connects the living room, dining area and a chef’s kitchen outfitted with high-end appliances, custom cabinetry and generous entertaining space. Multiple living areas, often found in premier Anna Maria Island homes, offer flexibility for hosting guests or enjoying quiet retreats. Each of the four bedrooms is generously sized, while the six total baths provide a resort-style convenience ideal for family and guests. The primary suite is typically a sanctuary of its own, featuring water views, private balcony access and a spa-inspired bath. Outside, the property becomes exceptional. A resort-style pool and spa overlook the bay, surrounded by lush tropical landscaping and expansive outdoor living areas designed for entertaining or unwinding in the coastal breeze. Waterfront homes here often emphasize seamless indoor-outdoor flow, creating an island lifestyle experience. With 235 feet of frontage, the property offers a private dock and boat lift, ideal for direct access to the open waters of Tampa Bay and the Gulf beyond. Whether you’re setting out for a sunset cruise, fishing at dawn or simply watching dolphins and manatees pass by, the water becomes an extension of daily life. Set on one of the desirable stretches of Anna Maria Island, this home combines rare waterfront scale, luxury amenities and effortless boating access, a showcase of elevated coastal living.

518 58th Street, Holmes Beach
605 N Point Drive, Holmes Beach
$2,950,000
4 Beds ⋅ 4 Baths ⋅ North Point Harbour SubDv. ⋅ 34217 Zip Code
Under contract-accepting backup offers. Nestled at one of the highest elevations on Anna Maria Island, this exceptional coastal retreat is located in the highly sought-after North Point Harbour community of Holmes Beach. Built in 2012 with hurricane-rated windows and doors, the home offers both refined elegance and peace of mind, perfectly blending luxury with the relaxed sophistication of island living. A cheerful front porch welcomes you inside, setting the tone for the warmth and charm found throughout. Soaring ceilings and gleaming marble floors create a light, airy ambiance, while coastal architectural details — including multiple porches and charming balconettes — add character and dimension to the design. The beautifully appointed living room is flooded with natural sunlight through two sets of French doors that frame tranquil canal views stretching toward Bimini Bay. These doors open to capture sunny mornings and breathtaking evening sunsets, seamlessly blending indoor and outdoor living. The open floor plan flows effortlessly into the dining and kitchen areas, creating an ideal setting for intimate family meals or hosting guests with ease. The spacious first-floor primary suite serves as a peaceful sanctuary, complete with a lovely ensuite bath and a private deck — perfect for quiet evenings under the coastal sky. Two additional bedrooms are also located on the first floor, including a second ensuite bedroom and a third bedroom with its own bath, offering comfort and privacy for family and visitors alike. Even everyday tasks feel elevated in the expansive and beautifully designed laundry and utility room, conveniently located off the kitchen and garage — a space so thoughtfully appointed it hardly feels like a utility area. The entire second floor is dedicated to a spectacular private suite. This luxurious retreat features two charming balconettes, a large walk-in closet, a spa-like ensuite bath with dual sinks, and a separate office or sitting room — an ideal haven for guests or multi-generational living. Outdoors, boating enthusiasts will appreciate the impressive 20,000-pound boat lift and expansive wraparound dock situated on a short, deep-water canal. With direct access through Bimini Bay to Tampa Bay, the Gulf of Mexico, and the Intracoastal Waterway, this property offers effortless navigation to some of Florida’s most beautiful waters. Life in North Point Harbour is as enriching as it is relaxing. Spend mornings at the nearby Key Royale Golf Club for an early tee time, afternoons joining friends at the community pool or enjoying a friendly match on the tennis courts or padel, and evenings cruising from your private dock into Bimini Bay as the sun melts into the horizon. Here, everyday flows seamlessly from recreation to relaxation, creating a true island lifestyle defined by beauty, convenience, and connection to the water. This extraordinary North Point Harbour residence embodies the very best of elevated coastal living — where thoughtful design, superior craftsmanship, and an unparalleled waterfront location come together to create a truly remarkable island home.

605 N Point Drive, Holmes Beach

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