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$3,600,000
3 Beds ⋅ 4 Baths ⋅ Regent Place SubDv. ⋅ 34228 Zip Code
Spectacular Gulf front location! Rarely available A floorpan Three bedroom, three bath direct beach corner residence with southern exposure with vistas to the beach, azure Gulf waters and sunsets plus views of the Longboat key Club golf course, Sarasota Bay and downtown Sarasota lights. Sunrise, sunsets are all enjoyed from this third floor spacious, open floor plan. A private, secured elevator opens to the interior of the residence while a separate elevator brings guests to the front door. Special features of this luxurious residence include 10' foot ceilings, floor to ceiling sliding glass doors, 8' solid mahogany doors plus porches on east and west side of this 3400 sq.ft. home. The kitchen has a wonderful center island plus a breakfast room. The master suite has expansive walls of windows enhancing the gulf views. The master bath is appointed with marble floors and walls, dual vanities and spa tub. Regent Place offers 24 hour security, a 25 -meter heated pool and spa overlooking the Gulf, summer kitchen by the pool, club house with social room and fitness center.

675 Longboat Club Road Unit 23A, Longboat Key
$1,675,000
5 Beds ⋅ 4 Baths ⋅ Queens Harbour (F/K/A Manchester Bay) SubDv. ⋅ 34228 Zip Code
One or more photo(s) has been virtually staged. Located behind the gates of Bay Isles in the established enclave of Queen’s Harbour, 3519 Fair Oaks Lane on Longboat Key offers 3,957± square feet of custom-designed living space with golf course and serene lake views. This residence was thoughtfully created in collaboration with the original developer as a fully customized floor plan to accommodate a large family—resulting in a layout that is both expansive and highly functional. This two-story home features 4-bedrooms plus a spacious upstairs multipurpose room that can easily serve as a fifth bedroom, along with 4.5 baths. The first floor is designed for gathering and everyday comfort, beginning with a private office at the entry, a formal dining room with 14-foot ceilings, an expansive family room, a generous kitchen with breakfast area, and a 1st-floor primary bed/bath suite. The kitchen offers solid wood cabinetry, stone surfaces, stainless appliances, a 5-burner natural gas cook-top, abundant counter space, and a breakfast bar—opening seamlessly to the main living areas and outdoor setting. The primary suite enjoys tranquil views of the pool, golf course, and lake, and includes walk-in closets, a soaking tub, and separate walk-in shower. Upstairs, three additional bedrooms are complemented by a large multipurpose bonus room that provides flexibility for a fifth bedroom, media room, playroom, or secondary office. Two bedrooms are connected by a Jack-and-Jill bath, while the remaining bedroom and bonus room share an additional full bath—ideal for larger households or hosting guests. Outdoor living reflects the relaxed elegance of Longboat Key, with a resurfaced saltwater pool, expansive paver deck, and mature tropical landscaping overlooking the fairway and water beyond. The setting is private, peaceful, and designed for enjoying Florida’s indoor-outdoor lifestyle. Major system updates add meaningful value, including a roof replacement in 2020 and air-conditioning systems replaced in 2022. An oversized two-car garage, two attic storage areas, and maintenance-free living within Queen’s Harbour further enhance convenience. Ownership includes deeded access to the private Bay Isles Beach Club on the Gulf of Mexico. Golf, tennis, boating, St. Armands Circle, and downtown Sarasota are just minutes away. A rare opportunity to personalize a truly custom-designed residence built for space, function, and multigenerational living—set within one of Longboat Key’s premier gated communities.

3519 Fair Oaks Lane, Longboat Key
$585,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Welcome to your dream retreat! This exquisite two-bedroom, two-bathroom condominium offers an unparalleled living experience, nestled within an amenity-rich community that defines coastal luxury. Picture yourself waking up to breathtaking marina views, with every window framing a picturesque panorama that will leave you in awe. As you step inside, you will notice the seamless blend of modern updates and timeless comfort. The open-concept living space is accentuated by floor-to-ceiling viewing windows, bathing the interior in natural light while providing unobstructed views of the tranquil waters. The updated kitchen is equipped with new cabinets, stone counters while the spacious primary suite includes a generous walk-in closet and dressing area. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Beyond the walls of your stunning condo, this professionally managed, pet friendly community encompasses 26 acres of beautifully landscaped grounds, providing a serene environment for leisure and recreation. Enjoy life to the fullest with an impressive array of amenities at your fingertips. Take advantage of the deeded beach access just steps away, where sun-soaked days and salty breezes await you. The community clubhouse serves as a hub for social gatherings, while two inviting pools provide refreshing escapes on warm afternoons. For the active lifestyle enthusiast, there are boat slips and kayak launches ready for your aquatic adventures, along with tennis and pickleball courts to keep you engaged and fit. Miles of walking trails weave through the property, perfect for leisurely strolls or invigorating jogs amidst nature’s beauty. This condominium isn't just a home; it's a lifestyle. With its prime location, stunning views, and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living. Don’t miss your chance to make this beautiful bayfront condo your own. Schedule a private showing today and experience the allure for yourself!

4960 Gulf Of Mexico Drive Unit 204, Longboat Key
$701,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
$50,000 PRICE IMPROVEMENT – Exceptional Luxury Bayfront Value on Longboat Key! Now offered at an incredible new price, this beautifully updated large END-UNIT condo presents a rare opportunity to own premier bayfront living in Windward Bay. Experience elevated Longboat Key bayfront living in this BEAUTIFULLY UPDATED and impeccably maintained 2-bedroom, 2-bathroom corner END-UNIT condo in the sought-after Windward Bay community. This ELEGANT RESIDENCE offers unobstructed full Sarasota Bay VIEWS from nearly every room through dramatic floor-to-ceiling windows. Exceptionally PRIVATE and boasting the LARGEST FLOOR PLAN in the community, this condo is located on the second floor with convenient elevator access - perfectly blending comfort, sophistication and coastal serenity. The open-concept kitchen features Italian quartz countertops, stainless steel appliances, a large breakfast island and 42"cabinetry with elegant, iridescent Mother-of-Pearl backsplash that flows seamlessly into the great room with tranquil water views. PORCELAIN tile flooring THROUGHOUT enhances the modern coastal aesthetic. The bayfront primary suite is a peaceful retreat and offers direct lanai access, a generous walk-in closet, and a luxurious ensuite bath with custom walk-in shower and dual-sink vanity. The second bedroom also enjoys bay views and lanai access, making it ideal for guests or a home office, and sits adjacent to updated guest bathroom. Additional conveniences include brand new in-unit laundry, private storage, and under-building parking. Recent upgrades include PGT hurricane-impact windows, including a premium, single pane panoramic window in the great room, a 2021 HVAC system, and a 2020 water heater. The monthly HOA fee of $1,325 includes hazard, hurricane and flood insurance, recreational amenities and FULLY FUNDED RESERVES - major value for bayfront condo ownership. There is a modest assessment $293 per month at a low interest rate. Windward Bay spans 26 acres of waterfront and offers resort-style amenities including BOAT SLIPS, kayak storage, three private beach access points, two heated pools, a fitness center, saunas, tennis and pickleball courts, walking paths, BBQ grills, fire pits, and a clubhouse. The community is PET FRIENDLY, allowing two pets up to 75 lbs each, and approved renter pets, making this an excellent primary residence, vacation home, or investment property. Located mid-island, you are minutes from championship golf, full-service marinas, St. Armands Circle, downtown Sarasota, and Anna Maria Island. Whether you are seeking a luxury Longboat Key waterfront condo, a serene island retreat or a strong rental opportunity, this exceptional bayfront residence delivers the ultimate coastal lifestyle!

4600 Gulf Of Mexico Drive Unit 206, Longboat Key
$900,000
2 Beds ⋅ 2 Baths ⋅ Privateer North SubDv. ⋅ 34228 Zip Code
Huge price reduction now under $1mm for direct 180 degree gulf front! Imagine waking up every morning to the sound of gentle waves and stepping onto your balcony to enjoy uninterrupted, straight-on Gulf views—this rarely available 01-stack residence delivers beachfront living exactly the way it should be. Perfectly positioned behind the private gates of the Longboat Key Club and nestled between the iconic Resort at Longboat Key Club and the spectacular new St. Regis Resort, Unit 301 at Privateer North is an ISLAND BEAUTY designed to delight the most discerning buyers. Picture yourself relaxing in the living room or primary suite, both opening to separate private balconies where you can sip your morning coffee, feel the warm Gulf breeze, and watch dolphins glide by almost daily. Then finish the day with some of the best sunsets in the state! With a layout tailored for coastal comfort, this home invites you to settle into a lifestyle where every day feels like a vacation. Residents enjoy a refined, resort-style environment with a secure lobby, on-site manager, tennis and pickleball courts, a heated pool and spa, well-equipped fitness center, and beautifully refurbished amenities. Everything has been updated: lobby, hallways, elevators, social room, and enhanced beachfront landscaping—creating an unmistakably fresh and upscale atmosphere. For golf, tennis, and pickleball enthusiasts, optional Longboat Key Club membership unlocks two championship golf courses (27 holes at Harbourside and 18 holes at Links on Longboat), 25 Har-Tru tennis courts, 8 new pickleball courts, professional instruction, and a top-tier pro shop. And when you venture beyond the gates, you’re moments from 10 miles of pristine beaches, boating, fishing, fine and casual dining, boutique shopping at the famous St Armands Circle, and Sarasota’s world-class cultural offerings just over the Ringling Bridge. Imagine living where every day ends with a beachfront sunset and every moment feels effortless—this is Longboat Key luxury at its finest, and it can be yours. Call for your private tour!

1050 Longboat Club Road Unit 301, Longboat Key
$1,100,000
3 Beds ⋅ 2 Baths ⋅ Country Club Shores SubDv. ⋅ 34228 Zip Code
Looking for a vacation getaway or an investment property? This cute coastal home on south Longboat Key is perfect! Just reduced in price to under $1.3 million! It is beautifully renovated and sold turnkey furnished with some exemptions, has a sparkling saltwater pool and spa, fenced in yard, new roof, peek-a-boo view of Sarasota Bay, has low HOA fees, generous rental policies and is close to the deeded beach access across the street! Thoughtfully updated throughout, this 3-bedroom, 2-bath residence with a 1-car garage is a great alternative to a condo and is pet friendly with a back patio and place to grille. Located in Country Club Shores, you’ll enjoy effortless access to everything: a private beach access, the boutiques and dining of St. Armands Circle less than 3 miles away, and Publix and CVS just minutes from your door. Set on an oversized lot you will enjoy stunning sunset views reflected off Ca da Zan across the Bay and the home’s outdoor living is just as impressive as its interiors. A screened-in saltwater pool and spa invite year-round enjoyment, while the covered dining and lounge areas make outdoor entertaining a breeze—yet there’s still plenty of lush green space to enjoy. Inside, luxury vinyl plank flooring flows throughout, complementing the light, coastal design. The fully remodeled kitchen features crisp white cabinetry, a spacious island with seating, and newer stainless steel appliances. Both bathrooms have been stylishly updated with wood vanities and vessel sinks. Additional peace of mind comes with on-demand tankless hot water and the reassuring fact that the home sustained no flooding or storm damage during the 2024 hurricanes. Move-in ready, low-maintenance, and steps from the beach—this Longboat Key gem makes coastal living refreshingly simple.

1050 Bogey Lane, Longboat Key
$1,425,000
3 Beds ⋅ 3 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code
Timeless sophistication meets resort-style elegance in this fully renovated 3-bedroom residence at the coveted Players Club on Longboat Key. Ideally situated on the sought-after south end of the island, this home places you moments from the prestigious St. Regis Hotel, the Longboat Key Club, Publix, and the upscale dining, boutique shopping, and cultural attractions of St. Armands Circle and downtown Sarasota. From the moment you enter, Gulf views and refined design elements set the tone. A complete interior transformation includes all-new flooring and doors throughout, freshly painted trim and doors, and upgraded Baldwin hardware and hinges. The expansive living area now showcases oversized marble tile, enhancing the natural light and coastal ambiance. The kitchen has been reimagined with quartz countertops, new backsplash, sink, faucet, and cooktop, plus a more open layout created by a partial wall removal. A redesigned dry bar with new cabinetry and dual beverage coolers makes entertaining effortless. Both guest and master suites have been thoughtfully upgraded. The guest bath features a new vanity faucet, mirror, sconces, shower glass, wallpaper removal, and polished nickel trim, while the guest bedroom’s bath is brightened with new lighting and fixtures. The primary suite serves as a private retreat with new floor tile, freshly painted walls, updated plumbing fixtures at the sinks, shower, and tub, custom California closets, and direct terrace access. Additional updates include all new electrical, a new washer, a new HVAC system, and fresh quartz countertops throughout the kitchen and baths — giving buyers peace of mind and a truly move-in-ready experience. Designed for effortless indoor-outdoor living, the living room, kitchen, and master bedroom all open onto a sprawling terrace, where sweeping views of lushly landscaped grounds and the sparkling Gulf of Mexico provide an inspiring backdrop. Life at the Players Club is defined by luxury and leisure, with an impressive array of amenities including a newly renovated clubhouse with a state-of-the-art fitness center, library, catering kitchen, and both indoor and outdoor gathering spaces. Residents also enjoy four Har-Tru tennis courts with pickleball capabilities, a 70-foot heated saltwater pool and spa, beautifully maintained tropical grounds, deeded beach access, and the peace of mind of 24/7 gated security and on-site management. This residence is being offered furnished (with exclusions - list will be provided) and includes under-building assigned parking, convenient bike racks, and a private storage closet just outside the front door. With its comprehensive renovations, prime location, and access to premier resort-style amenities, this Players Club residence presents a rare opportunity to experience the very best of Longboat Key’s coastal lifestyle.

1445 Gulf Of Mexico Drive Unit 304, Longboat Key
$1,062,000
3 Beds ⋅ 2 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code
Gulf-Front Elegance at The Players Club. Welcome to the epitome of coastal luxury living at The Players Club, where the pristine shores of Longboat Key meet world-class resort-style amenities. This beautifully renovated 3-bedroom, 2-bath split-plan residence is being offered turn-key furnished - ready for you to move in and immediately embrace the Gulf-front lifestyle. From the moment you step inside, you’ll notice the attention to detail: custom ceramic tile floors, exquisite cabinetry, and a thoughtfully designed open kitchen that seamlessly flows into the dining area/great room - perfect for entertaining. The gourmet kitchen is equipped with updated appliances, abundant storage, and elegant finishes, ensuring both functionality and style. Hurricane-impact sliding doors and windows provide peace of mind, while inviting breathtaking views of the pool, beach, and mesmerizing sunsets. Step onto your expansive terrace, the ideal setting for morning coffee or evening cocktails as you listen to the waves. The primary suite features generous walk-in closets, while the additional guest bedrooms, especially guest suite 3 with walls of closets, offers ample space for friends, family, and all your beach toys. The HVAC system has been updated and well-maintained, ensuring comfort year-round. Enjoy the privacy of a semi-private elevator, shared with only one neighbor, leading directly to your covered parking space just steps from your door. At The Players Club, every day feels like a vacation. Amenities include a renovated clubhouse with catering kitchen and library/meeting room, resort-style pool & cabanas just steps from the beach, Har-Tru tennis courts, pickleball, and putting green, and 24-hour fitness center, fire pits, and outdoor BBQs. You’ll also appreciate the fully funded reserves, successful milestone inspections, and recent elevator update/certifications, ensuring security and long-term peace of mind. Perfectly situated near the new St. Regis Resort and offering optional membership at The Longboat Key Club & Resort, you’ll have access to world-class golf, dining, tennis, and the only deep-water marina on the island. A short drive brings you to St. Armands Circle for upscale shopping, art galleries, and fine dining. Experience the best of Longboat Key living - call today to arrange your private showing and start living your Gulf-front dream.

1445 Gulf Of Mexico Drive Unit 404, Longboat Key
$337,500
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Some photo's have been virtually staged. Now is the time to buy this beautiful home in Spanish Main Yacht Club at an exceptionally low price for Longboat Key. This spacious, open concept, 2-bedroom, 2-bathroom villa has been renovated to FEMA regulations and rebuild specifications after Hurricane Helene. It is now ready for occupancy." Once you move in, you will enjoy Spanish Main's low-maintenance Longboat Key lifestyle with many restaurants within a short distance, deeded beach across Gulf of Mexico Drive, clubhouse, pool, private marina with a kayak launch and low-cost boat slips as available. Relax on your back patio with its tranquil view of flowering shrubs and trees. Your like-new home or investment property has been renovated to code with impact doors and windows, cupboards, quartz counter-tops, tiled tub and shower enclosures, brand-new kitchen appliances and hot water tank. The mini-split systems were installed in 2021, and the A/C and roof in 2015. Don't miss this opportunity to live the Longboat Key lifestyle at such a low price. Bring your cash offer with short closing date, and be rewarded with ownership of a valuable slice of paradise!

730 Spanish Drive S Unit 99, Longboat Key
$830,000
Bayview Estates SubDv. ⋅ 34228 Zip Code
Discover an extraordinary opportunity to build your dream waterfront retreat in the coveted Bayview Estates on world-famous Longboat Key. This exceptional saltwater canal lot offers direct access to the Intracoastal Waterway, Sarasota Bay, and the Gulf of Mexico—an absolute haven for boating enthusiasts. With a deep-water canal, dock, seawall, and lift already in place, the groundwork is set for effortless waterfront living and limitless design potential. The property features charming peekaboo bay views, with the opportunity to capture even more breathtaking vistas of Bishops Bayou and beyond through thoughtful elevation and architectural design. Imagine mornings greeted by peaceful sunrises, leisurely walks to the nearby beach just steps away, and unforgettable sunset views each evening. One of Longboat Key’s best surf breaks and public beach access are only moments from your door. All utilities are in place, making this an ideal canvas for new construction. Enjoy the quintessential island lifestyle with close proximity to fine dining, boutique shopping, tennis clubs, fitness centers, and beautiful community parks. This is a rare chance to own a prime piece of land in one of Longboat Key’s most desirable neighborhoods and bring your vision of luxury waterfront living to life. Schedule your private tour today and experience the possibilities firsthand.

579 Bayview Drive, Longboat Key
$1,300,000
2 Beds ⋅ 2 Baths ⋅ Aquarius Club SubDv. ⋅ 34228 Zip Code
AQUARIUS CLUB – This renovated fourth-floor condo presents a rare opportunity to own the ultimate beachfront retreat on the coveted south end of Longboat Key, where ownership includes a complimentary social membership to the adjacent brand-new St. Regis Resort. Nestled within an intimate boutique community of just 58 residences, the Aquarius Club recently underwent extensive renovations led by the renowned JKL Design Group, meticulously modernizing the hallways, club room, fitness center, and conference space; these updates are backed by a financially strong and well-managed association, securing both an elevated aesthetic and lasting investment value. Modern design blends seamlessly with coastal elegance in this two-bedroom, two-bathroom residence, with 1,551 Sq. ft of open living space, in an open-concept split bedroom floor plan. A generous balcony offers views of the Gulf with floor-to-ceiling windows and sliding glass doors, making the space both expansive and welcoming throughout, with new wood floors in the main living areas. The updated kitchen is open to the living area, with thoughtful details such as quartz countertops, an island with waterfall edge, recessed lighting, open shelving and modern cabinetry blending sleek white finishes with natural wood. The state-of-the-art Café appliances include a French door refrigerator and electric range (with glass cooktop and double convection ovens), plus an undermount single basin stainless steel kitchen sink by Moen. The epitome of luxury and comfort, the spacious primary bedroom has plantation shutters and a private ensuite bath that features an open, integrated dressing area and tub. The additional bedroom is stylish and functional, with new carpet, and floor-to-ceiling windows with plantation shutters. Enjoy an amenity-rich lifestyle beachside with onsite management, a heated Gulf-front pool, Har-Tru tennis and pickleball courts, a fitness center, library and game room, barbecue grill, and covered parking. The included social membership to the St. Regis provides access to its luxury pool, spa services, state-of-the-art fitness center, discerning dining opportunities, and exclusive hotel discounts. Conveniently located near Bay Isles shopping, St. Armands Circle, and Downtown Sarasota’s cultural attractions, this property is ideal for those seeking a beachfront escape or a smart investment opportunity. Embrace the unparalleled sophistication and charm of the Longboat Key lifestyle.

1701 Gulf Of Mexico Drive Unit 404, Longboat Key
$850,000
2 Beds ⋅ 2 Baths ⋅ Longboat Terrace SubDv. ⋅ 34228 Zip Code
Gorgeous full beach and gulf views from this TURNKEY furnished Tommy Bahama style unit. Spacious rooms with a kitchen that opens to the dining and living area, all facing the Gulf. The primary bedroom and living room both open to a generously sized screened porch to sip your morning coffee or just listen to the surf. ELECTRONIC HURRICANE SHUTTERS offer ease and peace of mind. A versatile bonus room off the kitchen includes a sofa bed, plantation shutters and sliding pocket doors offering a flexible space for guests or hobbies. Crown molding, granite, and large neutral tile on the diagonal in main living areas are just some of the upgrades. Unit has inside stackable washer and dryer. Amenities include a gulf side heated pool, social events at the clubhouse and a fitness area. Longboat Terrace is a pet friendly beachfront community of just 36 residences. Conveniently located across the street from several favorite local dining spots! Visit the nearby Durante park for nature trails when you?re looking for a change from relaxing beach and pool days. Longboat Terrace is the perfect place to call home or to use as a seasonal getaway!

5393 Gulf Of Mexico Drive Unit 211, Longboat Key
$629,950
2 Beds ⋅ 2 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code
LOWEST PRICED 2 BEDROOM CONDO IN BAY ISLES. This desirable corner residence at Grand Bay showcases an expansive wraparound terrace overlooking Sarasota Bay—perfect for enjoying stunning sunrises over the Bay and sunsets over the gardens and golf course. Uniquely positioned for privacy, this home has been tastefully updated with a neutral color palette and comes fully furnished, and is the lowest-priced 2 Bedroom condo in prestigious Bay Isles. The kitchen shines with quartz countertops, full-height backsplash, double oven, new sink and plumbing fixtures, under-cabinet lighting, and stainless appliances. A convenient pass-through connects seamlessly to the living area for easy entertaining. The primary suite offers floor-to-ceiling sliders opening to the oversized terrace, a luxurious ensuite bath with double vanity, glass-enclosed shower, jetted soaking tub, and custom walk-in closet. The private guest suite features its own bath, large walk-in closet, terrace access, and pocket doors for added privacy. Both Bedrooms have wide plank hardwood floors. Additional highlights include two side-by-side under-building parking spaces near the elevator, and a private storage locker. Grand Bay is a pet-friendly, guard-gated community offering resort-style living with semi-private elevators, a state-of-the-art fitness center, Har-Tru tennis courts, outdoor grills, and two sparkling pools. Residents also enjoy membership in the private Bay Isles Beach Club with deeded beach access, pavilion, restrooms, and gated parking.

3070 Grand Bay Boulevard Unit 612, Longboat Key