Location: Longboat Key , 34228
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6489 GULFSIDE RD, LONGBOAT KEY, FL 34228
$13,995,00095 Days on yellowkey MLS ID: A4677413
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 6616 Built: 2026 Tax: $42,641 (2025)Community: Sleepy LagoonSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$42,641
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Nicholle Mckiernan (941-928-2922)
4561 GULF OF MEXICO DR #202, LONGBOAT KEY, FL 34228
$2,750,000130 Days on yellowkey MLS ID: A4674911
REDUCED by $200,000 (6.8%) on 04/20/2026
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3260 Built: 1999 Tax: $29,736 (2024)Community: The Grande At Longboat KeySpa: YesCondo
Taxes:$29,736
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Spectacular North west corner three bedroom condo with direct beachfront views at The Grande, a oasis with only 8 residences. This is Florida living at its very best! This second floor corner location has breathtaking views of the Gulf of Mexico and miles of beautiful sandy beach plus some views of Sarasota Bay and amazing sunsets. A fantastic wrapping terrace on the Gulfside offers outdoor enjoyment from the main living area and master suite. Two other terraces off the additional bedrooms with privacy and wonderful views. This true three bedroom, all with private baths, is 3260 square feet. A Gulf front gourmet kitchen with high end appliances has an adjacent family gathering area. The open plan flows from the living room area to the dining room and the floor to ceiling windows that dramatically overlook the Gulf of Mexico and beach, enhance the brightness and open feeling of this home. This home has 10 foot ceilings, and comes with a private enclosed two car garage with direct access.This Longboat location is near many outstanding restaurants and Anna Maria Island. Watch dolphins and manatees and so many Florida birds glide past your backyard. The azure waters of the Gulf of Mexico and the beach are just steps away.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228
$4,395,000161 Days on yellowkey MLS ID: A4671696
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5080 Built: 1996Monthly Fee: $208 Tax: $42,201 (2024)Community: Bay IslesSpa: YesSingle Family
Taxes:$42,201
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: An extraordinary Contemporary Architectural estate — now offered with a $500,000 price reduction, presenting one of the most compelling waterfront opportunities on Longboat Key. Defined by its rare three-pod circular design, this sculptural residence is a dramatic composition of flowing living spaces connected by custom corridors — delivering exceptional privacy, abundant natural light, and seamless indoor–outdoor living. The Great Room pod features soaring wood-paneled ceilings and walls of glass framing tranquil water views. The circular primary suite offers a spa-level bath with dual showers, private office, lounge area, and direct pool access. The striking circular kitchen showcases a curved island beneath a two-story ceiling and skylight, with a radial appliance layout that is both artful and highly functional. Two en-suite guest bedrooms open to private patios, while a fully self-contained Secondary Primary Suite above the 32' x 23' three-car garage includes independent HVAC, a luxury bath with Steam Shower and Sauna, a flexible living space ideal for extended guests. Outdoors, enjoy protected deep sailboat water, a private dock with 12,000-lb lift, and a resort-style pool and spa. Situated behind the 24-hour gates of Bay Isles, with exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: John August (941-320-9795)
600 PUTTER LN, LONGBOAT KEY, FL 34228
$10,500,000473 Days on yellowkey MLS ID: A4633484
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 5982 Built: 2017Monthly Fee: $17 Tax: $69,287 (2025)Community: Country Club Shores, Unit 5, Sec 3Spa: YesSingle Family
Taxes:$69,287
Remarks: Welcome to Paradise on Longboat Key. This coastal modern home is located on the direct bayfront with a total of 270 feet of waterfront on an oversized lot consisting of 18,290 square feet. As you enter the home, your first view is a serene and expansive view of Sarasota Bay all the way from the Ringling Museum to Downtown Sarasota and the Ringling Bridge. Enjoy different types of boating as the dock includes 2 jet ski lifts and a 13,000 pound boat lift. With plenty of interior space, there are 5 bedrooms and 5 baths plus a dedicated office/den, family room and game room. Every bedroom is filled with bay views. As an added advantage, guests have their own space upstairs that includes a kitchenette. Outfitted with an elevator that stops at every floor, including the three car garage, convenience is just a step away. To enjoy the views outside, there is an outdoor surround lanai with disappearing screens, fireplace and summer kitchen. Large covered terraces on both levels provide views of beautiful sunrises over Sarasota Bay and Downtown Sarasota.
Listing is courtesy of: FLORIDA CAPITAL REALTY (786-953-5870)
Listing Agent: Kathleen Callender (941-321-3115)
501 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$1,068,375273 Days on yellowkey MLS ID: TB8398888
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1708 Built: 1972 Tax: $13,238 (2024)Community: Sleepy Lagoon ParkSpa: NoSingle Family
Taxes:$13,238
Remarks: Some homes whisper. Others make a statement. 501 De Narvaez Drive commands attention—with bold architecture, elegant updates, and a prime waterfront location that elevates the Florida lifestyle into something exceptional. Nestled on a quiet corner lot in the coveted Sleepy Lagoon Park neighborhood, this home is your gateway to prestige, privacy, and the purest form of coastal living. Spanning 1,708 square feet of refined single-story living, this 3-bedroom, 2.5-bath residence is a masterclass in modern comfort and timeless materials. Designed with block construction and finished in stucco with a durable metal roof, the home is as solid as it is stylish. Inside, terrazzo flooring sweeps across the entire home, providing a sleek and enduring foundation underfoot. Enter into a light-drenched open floor plan, where the layout has been carefully crafted for entertaining, lounging, and effortless day-to-day living. The living room flows into a dining space and gourmet kitchen—outfitted with stone counters, solid surface tops, a spacious island, and stainless steel appliances including a convection oven and cooktop. Whether you’re entertaining guests or enjoying a peaceful morning coffee, every room connects you to the water and the outdoors. The primary suite is an owner’s haven, complete with a walk-in closet and full bath featuring a tub/shower combination. Two additional bedrooms—each with walk-in closets—offer comfort, functionality, and flexibility. A second full bath, half bath, and spacious laundry area provide all the elements of ease and convenience. But what truly defines this home is what lies beyond the doors. A private, heated pool, enclosed within a screened lanai, becomes your year-round sanctuary. The oversized covered deck is perfect for afternoon shade or sunset cocktails. And then there’s the water: with direct canal access to the Intracoastal Waterway, this home is a dream for boaters. The 2022 composite dock and concrete seawall are in pristine condition and ready for your vessel. No HOA means you can live your way, and with 1-month minimum leases allowed (rental license required), this property also offers incredible short- or long-term rental potential. Add in a two-car garage, central air, electric heat, public water/sewer, and fiber optic internet, and you have every modern amenity at your fingertips. This is more than just a home—it’s a statement of lifestyle. A bold, beautiful, and rare opportunity to own in one of Longboat Key’s most established and beloved communities, just moments from world-class beaches, golf, fine dining, and everything the Sarasota area has to offer. For the visionary buyer who seeks distinction, privacy, and water access—501 De Narvaez is where your story begins.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
545 SANCTUARY DR #B204, LONGBOAT KEY, FL 34228
$2,799,000180 Days on yellowkey MLS ID: A4667288
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3115 Built: 1991 Tax: $19,659 (2025)Community: Sanctuary IiiSpa: YesCondo
Taxes:$19,659
Remarks: Prepare to be wowed by the direct turquoise Gulf views from the oversized wraparound terrace, main living areas and primary bedroom. The chef’s kitchen is open to the main living area and offers state-of-the-art JennAir stainless steel appliances complete with built-in convection and steam ovens, oversized center island, wine refrigeration with storage and breakfast area. The massive primary suite showcases floor to ceiling windows with the same big Gulf views, access to the terrace, garden tub with separate shower and two walk-in closets. The main guest bedroom is ensuite with its own private terrace access and another walk-in closet. The 3rd bedroom is being used as a den with French doors opening to the living room, its own ensuite full bath with shower and dazzling Gulf views. Other bonus rooms include a laundry room located conveniently off the kitchen with sink, and an office nook with built-ins adjacent to the foyer. This residence comes with TWO under building parking spaces and a separate storage locker. Located behind the prestigious gates of The Longboat Key Club on the desirable South end of Longboat Key, owners will enjoy being minutes from the fine dining and shopping on St. Armands Circle in addition to the close proximity to Southwest Florida’s cultural hub of downtown Sarasota. At the Sanctuary, you will be part of 18 incredible beachfront acres with trails, an Olympic sized heated pool and spa, lighted tennis courts, a fitness center, onsite management, 24-hour manned security gate and a club house with planned activities. Become a member of the Longboat Key Club and partake in the superior golf courses, 6 private restaurants, spa and wellness center and other AAA four-diamond beach resort offerings. Roof replaced in 2023, Elevators modernized in 2022, and pool decking replaced in 2024. Building passed the Milestone Structural Integrity Inspection.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
2110 HARBOURSIDE DR #536, LONGBOAT KEY, FL 34228
$799,000Listed 04/20/2026 9:35AM MLS ID: A4685244
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988 Tax: $12,286 (2025)Community: Fairway Bay 3Spa: YesCondo
Taxes:$12,286
Remarks: Completely reimagined with an uncompromising eye for detail, this furnished, southeast-facing 3-bedroom residence in The Atrium of Fairway Bay offers refined living with sweeping views across the lagoon, mangroves, open bay, and Sarasota skyline beyond. Thoughtfully remodeled with no expense spared, the flexible layout feels both elegant and exceptionally functional. Rich wood floors run throughout the main living areas, grounding the residence in warmth and sophistication while complementing the shimmering water and city views beyond the glass. A curated mix of tile, wood, stone, and carefully selected colors creates a distinctive ambiance throughout. In the living room, a full wall of sliders opens to a covered terrace that invites the outdoors in and captures the tranquil beauty of the surrounding vistas. Recessed lighting, 8-inch crown molding, plantation shutters, custom-built cabinetry, and a dry bar with wine fridge elevate the space with both style and purpose. The kitchen is beautifully tailored for daily living and entertaining alike, featuring a large custom island with cooktop, granite counters, tile backsplash, tray ceiling, Bosch stainless steel appliances, a built-in desk, and an oversized custom pantry that adds rare storage and convenience. The primary suite is a spacious retreat, highlighted by a dramatic corner wall of floor-to-ceiling glass and slider access to the terrace. Its bath is generously sized and beautifully finished with dual vanities, warm wood accents, and a glass walk-in shower with built-in bench. Two additional bedrooms provide flexibility for guests, a home office, or den, complemented by a beautifully updated full bath. Additional features include an in-residence laundry room and a top-tier AC system equipped with ultraviolet germicidal UV light and an Ecobee smart programmable thermostat. Located behind the gates of Bay Isles, The Atrium of Fairway Bay offers a relaxed, amenity-rich lifestyle with two community pools, tennis courts, fitness facilities, beautifully landscaped bayfront walking paths, kayak access, and deeded Gulf beach access through the Bay Isles Beach Club. Residents also enjoy 24-hour gated security, with optional access to Longboat Key Golf & Tennis Country Club memberships and deepwater slips.
Listing Agent: Bruce Myer (941-376-5311)
5320 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$1,150,000199 Days on yellowkey MLS ID: A4666843
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1323 Built: 1981Monthly Fee: $1,483 Tax: $11,774 (2024)Community: Longboat LandingCondo
Taxes:$11,774
Remarks: Rarely Available at Longboat Landing! This 3-bedroom, 2-bath second-floor condo offers the ultimate in coastal living with only 9 total units/owners in the entire community—providing privacy, exclusivity, and a boutique feel. Enjoy full Sarasota Bay views from your living room, with the added peace of mind of being on the second floor (no flood concerns). Inside, you’ll find engineered hardwood floors, a granite countertop kitchen, and hurricane impact windows that fill the space with light and frame the water beyond. The spacious primary suite offers a private retreat, while two additional bedrooms provide room for guests, a home office, or flex space. Outside, embrace the Longboat Key lifestyle with a boat dock slip, fishing pier, and community amenities designed for waterfront enjoyment. Perfectly located on Gulf of Mexico Drive, just minutes from island dining, boutique shopping, and the world-renowned beaches of Longboat Key. Rarely available. Bayfront views. Exclusive 9-owner community. This one is not to be missed!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Schuyler Burke (907-223-8161)
360 GULF OF MEXICO DR #333, LONGBOAT KEY, FL 34228
$1,795,00099 Days on yellowkey MLS ID: A4675387
REDUCED by $5,000 (0.3%) on 04/20/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2581 Built: 1992Monthly Fee: $50 Tax: $10,264 (2025)Community: Tangerine Bay ClubCondo
Taxes:$10,264
Remarks: Welcome to this rarely available corner penthouse with its stunning bayfront views artfully framed by the freshly landscaped tropical oasis surrounding the resort-style pool. Boasting nearly 2600 square feet of interior space on two levels, this serene sanctuary offers three terraces plus 3 bedrooms and 3.5 baths (3045 square feet in total). A private courtyard sets the stage for a gracious residence with a warm European feel that lives like a single family home. Relaxed open spaces beckon with soaring ceilings, extra windows in the kitchen and great room (available only in end units), and a gas fireplace. The kitchen features a morning room with built-in desk and an aquarium window over the sink. Sliding glass doors seamlessly connect indoor and outdoor spaces. Mahogany double doors open into the primary suite with its patio access overlooking the bay and lush landscaping, volume ceilings, acacia wood flooring, walk-in and built-in closets and recently renovated luxurious bath. An additional guest bedroom (currently used as a den) with ensuite bath, laundry room and powder room complete the first level. On the second level a spacious third bedroom, office with built-in desk, shelving and storage, and full bath provide additional accommodations for family and friends. The home offers impact windows, plus storm shutters on larger windows for added protection. Enjoy the resort style amenities of Tangerine Bay Club, including a lagoon pool with waterfalls, lap lane and spa, day dock, fishing, kayak launch, tennis and pickleball courts, fitness center, clubhouse, walking paths and tropical landscaping. An oversized garage provides ample space for sports equipment and storage. Owners may join the newly remodeled Bay Isles Beach Club providing access to the Gulf of Mexico for a modest annual fee. Located on Longboat's south end, this gated community is just minutes from the new St. Regis resort and St. Armand's Circle with its shops and fine dining. A short drive over the Ringling Bridge brings the vibrant culture and renowned arts of downtown Sarasota. Optional membership in the Longboat Key Club across the street from TBC offers 45 holes of award winning golf, fine dining and a marina. Come see why Tangerine Bay Club is one of Longboat's most sought after communities and why Forbes named Longboat Key one of the top 25 destinations in 2025.
Listing Agent: Sherry Dominick (203-605-9582)
4440 EXETER DR #301, LONGBOAT KEY, FL 34228
$585,00047 Days on yellowkey MLS ID: A4684917
REDUCED by $10,000 (1.7%) on 04/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1970 Tax: $8,101 (2024)Community: Longboat HarbourCondo
Taxes:$8,101
Remarks: Welcome to this beautifully updated top floor corner furnished residence with Gulf and Bay views that is move in ready. Coming furnished with an open kitchen floor plan and an enclosed lanai overlooking the pool and Sarasota Bay. Large plank ceramic tiles throughout and ceiling fans in every room, hurricane impact glass windows in the kitchen and living area and a washer/dryer has been added. All tv's within the residence stay. The Longboat Harbour community is located mid-Longboat Key with amenities to enjoy including a large clubhouse where many activities occur, with a catering kitchen and dance floor, art studio, billiard and card rooms, and a fully equipped fitness center. In addition, the community has four heated swimming pools, putting green, tennis and pickleball courts, kayak storage, boat slips available for a minimal annual fee for up to a 34’ boat, mini golf, a scenic waterfront promenade along the harbor and canal, and access to a private gated Beach Club on the Gulf side with bathrooms, showers and beach items. The building has just completed a new roof installed. There is additional storage withing the building for each residence as well as a storage closet on the enclosed lanai.
Listing Agent: Michael Moulton (941-928-3559)
2301 GULF OF MEXICO DR #101N, LONGBOAT KEY, FL 34228
$1,395,000158 Days on yellowkey MLS ID: A4671549
0 Days Off yellowkey (back on 4/20/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $11,705 (2024)Community: Islander Club Of LongboatSpa: NoCondo
Taxes:$11,705
Remarks: Under contract-accepting backup offers. FULLY RENOVATED - Set high on the 10th floor with direct Gulf and beachfront vistas, this 2BR, 2BA residence in the Islander Club offers a front-row seat to a breathtaking panorama on Longboat Key. From the moment you step through the foyer, the horizon opens wide, unveiling sweeping blues and azures that stretch up the shoreline and out to the Gulf. Diagonal tile floors and neutral tones create a soft, calming backdrop that allows the views to take center stage, while floor-to-ceiling sliders in every room invite natural light and warm Gulf breezes inside. The beautifully renovated kitchen feels timeless and ahead of its era, featuring white shaker cabinetry with glass panel accents, stone countertops, stainless-steel appliances, white tile backsplash, recessed lighting and a generous breakfast bar that connects seamlessly to the living area. A wall of sliders opens to the terrace, where the Gulf becomes an extension of your living space. Both bedrooms offer terrace access and stunning floor-to-ceiling windows, making each space feel bright, airy and connected to the beauty outside. Each suite includes its own full bath, creating comfort and privacy for owners and guests alike. A continuous terrace spans the full length of the residence, allowing you to step out from any room and enjoy the Gulf’s shifting colors, uninterrupted breezes and nightly sunsets. Set in a prime mid-key location, Islander Club elevates the beachfront lifestyle with outstanding amenities, including a beachfront pool, tennis courts, updated clubhouse, new fitness center, library, billiards room and secure gated entry. All of it sits just steps from the sand and a short drive from the shopping, dining and cultural attractions of St. Armands Circle and downtown Sarasota.
1485 GULF OF MEXICO DR #110, LONGBOAT KEY, FL 34228
$1,495,00077 Days on yellowkey MLS ID: A4681044
Bed: 2 Bath: 3.0 Liv Area Sq Ft: 1971 Built: 1981 Tax: $10,505 (2025)Community: Players Club ISpa: YesCondo
Taxes:$10,505
Remarks: Under contract-accepting backup offers. With the Gulf just beyond the terrace, this first-floor two-bedroom, three-bath residence at The Players Club offers direct beachfront living, where uninterrupted water views and the steady rhythm of the shoreline shape daily life. Updated in 2021–2022 and move-in ready, the residence spans approximately 1,971 square feet and has been redesigned to emphasize its coastal setting. High-impact glass, recessed lighting, and a neutral interior palette create a bright, understated backdrop throughout. The open kitchen connects to the main living areas and features white quartz countertops, coordinating cabinetry, stainless steel appliances, and a tile backsplash. A solarium just off the kitchen provides flexible space for an office or den and is finished with plantation shutters. Adjacent to the solarium is the third full bathroom and closet. The living room opens to the terrace through a wall of sliding glass doors, extending the living space outdoors. The private terrace spans approximately 30 feet and overlooks the beach and Gulf, offering a comfortable setting for dining, relaxing, or entertaining. The split-bedroom floor plan provides privacy, with a guest suite that includes an updated en-suite bath. The primary suite opens directly to the terrace and features a walk-in closet and an updated bath with dual vanities and a glass-enclosed shower with built-in bench. Additional features include in-residence laundry, extra storage, and under-building parking. Located on the southern end of Longboat Key, The Players Club offers 560 feet of private beach frontage, a 24-hour guarded gate, on-site management, Har-Tru tennis courts, pickleball courts, a heated saltwater pool and spa, and a recently refreshed clubhouse.
210 SANDS POINT RD #2405, LONGBOAT KEY, FL 34228
$1,100,000228 Days on yellowkey MLS ID: A4664039
REDUCED by $50,000 (4.3%) on 04/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 650 Built: 1982 Tax: $9,827 (2024)Community: Inn On The Beach Ph ICondo
Taxes:$9,827
Remarks: Located behind the gates of the highly desirable Longboat Key Club, this 1BR/1BA Club Suite at Inn on the Beach offers a unique opportunity to own within the prestigious Longboat Key Club Resort. Spanning 650 sq. ft., this residence provides both convenience and privacy, with an expansive covered terrace offering peaceful Gulf views while keeping you close to every amenity. Completely renovated and meticulously styled, the interior pairs warm wood accents with neutral tones, complemented by faux wood tile floors flowing throughout. Dual sliders frame shimmering Gulf waters and invite natural light into the living space. The kitchen is a standout, with stone countertops, harmonizing cabinetry with glass panel accents and a colorful tile backsplash that adds just the right touch of vibrancy. Off the bedroom space, a beautifully updated bath features all-white cabinetry, a separate water closet and a glass walk-in shower with striking tilework. For added ease, in-unit laundry utilities are included. This unit participates in the Resort Rental Program and has a healthy rental history, with nightly rentals allowed, making it both an enjoyable retreat and a strong investment. As an owner, you’ll have access to the exclusive amenities of the 410-acre Longboat Key Club, including 45 holes of championship golf, 20 Har-Tru tennis courts at the award-winning Tennis Gardens, a full-service marina, private Gulf-front beach with umbrellas and attendant service, a world-class fitness and wellness center, spa and five private dining options. Recently renovated guest services, dining areas, and resort amenities have elevated the experience even further, earning accolades such as the AAA Four-Diamond Award and recognition from Condé Nast Traveler as a Top Florida Resort.
1912 HARBOURSIDE DR #602, LONGBOAT KEY, FL 34228
$549,900186 Days on yellowkey MLS ID: A4668394
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1590 Built: 1982 Tax: $6,146 (2024)Community: Fairway Bay 1Spa: YesCondo
Taxes:$6,146
Middle School: Pine View School
Remarks: NEWLY painted bright and fresh INTERIOR. Discover the ideal blend of comfort, convenience, and coastal charm in this beautifully furnished townhouse in Fairway Bay, a sought-after, gated community within Bay Isles on Longboat Key. Enjoy easy access to the gorgeous Gulf beach of Longboat Key via a private beach club, and an abundance of activities, including biking, recreation, pickleball and tennis, ideal for those who embrace an active lifestyle. The main level of this townhome offers an open, eat-in kitchen with a breakfast bar that flows effortlessly into the inviting living room, complete with a wood-burning fireplace and large sliding doors leading to a screened lanai with stairs to the outdoors. A convenient half bath completes this level, making it ideal for entertaining. Upstairs, the primary suite features a spacious walk-in closet and a private en-suite bath with double sinks. A second bedroom, also with its full en-suite bath, provides comfort and privacy for guests. The laundry is conveniently on this upper level. On the garage level, you’ll find a large storage room and a bonus space, offering endless possibilities such as a home gym, hobby area or even a space for guests. Fairway Bay homeowners have access to the on-site clubhouse, where there are social activities, a community gym and Har-Tru tennis courts for residents only. Fairway Bay is in Bay Isles, where you have 24/7 gated security and deeded access to the beautiful and private Bay Isles Beach Club. Here you can enjoy gated parking, restrooms, beach chair and umbrella storage, an ice machine, refrigerator and microwave, the ideal place for barbecues, picnics, and sunset gatherings with family and friends. Furniture is included, making this an effortless move-in opportunity to start enjoying the Longboat Key lifestyle from day one. This home is in proximity to Longboat Key Club where you have 45 holes of golf, a world-class tennis center, pickleball courts and five private restaurants accessible to you with additional membership. It’s rare to find a home in Bay Isles offering this level of lifestyle, amenities and value. Don’t miss this opportunity to live your best life on Longboat Key and start making memories of a lifetime today.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Judy Mitchell (941-275-6838)
3806 GULF OF MEXICO DR #C312, LONGBOAT KEY, FL 34228
$320,0001 Day on yellowkey MLS ID: A4690206
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1062 Built: 1970 Tax: $3,659 (2025)Community: Beach Harbor ClubCondo
Taxes:$3,659
Remarks: LONGBOAT KEY 2-bedroom, 2-bathroom end-unit condo offering a coastal lifestyle with convenient access to both the Gulf of Mexico and Sarasota Bay. This third-floor corner unit is filled with natural light, turnkey furnished and offers added privacy with no unit above. Interior features include a welcoming foyer entry and a flexible second bedroom with a retractable partition and Murphy bed, ideal for guests or a multipurpose space. Tile flooring runs throughout for easy maintenance. The HVAC system was replaced in 2024. The building provides secure entry and an assigned covered carport. Beach Harbor Club is a waterfront community spanning approximately 5.3 acres on Longboat Key, consisting of 133 units and uniquely positioned between the Gulf of Mexico and Sarasota Bay. Residents enjoy deeded beach access with showers, umbrellas, and beach chairs, along with bayfront amenities including a seawall, fishing areas, and newly constructed boat slips. Community features include an oversized heated swimming pool, clubhouse, fitness center, shuffleboard courts, outdoor cooking and grilling areas, kayak launch and storage, guest parking, additional storage, and on-site management. This community supports an active coastal lifestyle with opportunities for boating, kayaking, fishing, and beachgoing. The property is located near Bayfront Park with tennis facilities and is convenient to nearby shopping and everyday essentials.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Greg Hudson (941-302-1485)
1211 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228
$1,590,000175 Days on yellowkey MLS ID: A4669896
REDUCED by $85,000 (5.1%) on 04/19/2026
Bed: 2 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2100 Built: 1985 Tax: $14,792 (2025)Community: PromenadeSpa: YesCondo
Taxes:$14,792
Remarks: Rarely available north-side corner residence at The Promenade showcases panoramic views of the Gulf of Mexico, Sarasota Bay, white sandy beaches, and the sparkling city skyline. This beautifully designed 2,100 sq. ft. “E” floor plan features two bedrooms plus a den/3rd bedroom (with an en-suite full bath) and three bathrooms, with a spacious split layout that captures natural light and breathtaking vistas from every room. The expansive living and dining areas flow seamlessly to two private terraces—set your morning coffee down as you watch the sunrise over the bay, and end the day with a glass of wine while taking in the sunset over the Gulf. A stylish wet bar adds the perfect touch for entertaining. The kitchen is a showpiece, featuring 2022 installed Sub Zero refrigerator/freezer, GE Monogram stainless-steel induction cooktop and oven, ASCO dishwasher and GE Monogram microwave / convection oven combo, a white subway tile backsplash, quartz countertops, sleek contemporary white cabinetry, and an eat-in area overlooking the bay. Engineered white oak hardwood floors extend throughout, adding warmth and sophistication. The primary suite offers stunning Gulf views, built-in cabinetry, and two walk-in closets, while the guest suite enjoys downtown views and a private bath. The third bedroom/den opens to a terrace overlooking the Gulf. Includes one deeded parking space and access to resort-style amenities—concierge, 24-hour security, fitness center, an Olympic-size heated pool, four Har-Tru tennis courts, and more.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
5655 GULF OF MEXICO DR #D107, LONGBOAT KEY, FL 34228
$799,00046 Days on yellowkey MLS ID: TB8483958
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1274 Built: 1975Monthly Fee: $1,164 Tax: $3,439 (2025)Community: Cedars West Of Longboat IncCondo
Taxes:$3,439
Remarks: Experience breathtaking beach and Gulf views from this spacious, turnkey-furnished two-bedroom, two-bath residence in Cedars West. Beautifully updated with no detail overlooked, this exceptional property features elegant stone countertops, quality appliances, and a relaxed coastal ambiance that makes it highly sought after. Offering over 1,270 square feet of air-conditioned living space, the residence includes a large walkout screened lanai where you can enjoy gentle Gulf breezes and spectacular sunsets over the tranquil waters of the Gulf of Mexico. The thoughtfully designed layout provides abundant storage throughout, including generous closets in both bedrooms as well as a dedicated owner’s closet. Just steps from the unit, the pristine beach is a renowned nesting ground for sea turtles, offering the unique opportunity to watch dolphins and manatees pass by while relaxing on one of Florida’s most beautiful beaches. Cedars West residents enjoy a wide range of resort-style amenities, including a large heated and cooled swimming pool, two tennis courts, BBQ grilling areas, and convenient kayak and bike racks. Owners also have the option to generate rental income by taking advantage of Cedars West’s rare two-week minimum rental policy on Longboat Key. Don’t miss this incredible opportunity to experience the ultimate beachfront lifestyle.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: John Milkovich (727-518-5058)
550 YARDARM LN, LONGBOAT KEY, FL 34228
$3,795,000152 Days on yellowkey MLS ID: A4672604
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4281 Built: 2006Monthly Fee: $23 Tax: $16,615 (2024)Community: Country Club Shores Sec 02Spa: YesSingle Family
Taxes:$16,615
Remarks: Price improvement ….ELEVATED Waterfront Luxury on Longboat Key! Welcome to 550 Yardarm Lane, where the elegance of Longboat Key meets the ease of Florida’s coastal lifestyle in the coveted Country Club Shores. This waterfront masterpiece isn’t just a home, it’s your front-row seat to paradise, where boating, beach walks, and year-round sunshine are part of everyday life. Step inside and be instantly captivated by sparkling water views, soaring spaces, and the perfect blend of casual comfort and refined luxury. Designed for both relaxation and unforgettable entertaining, this 5-bedroom, 5.5-bath retreat is tailor-made for hosting family and friends in style. PRIME WATERFRONT LIVING - Private dock on a deep-water canal with no-bridge access to the bay, perfect for your weekend cruiser. LIGHT & BRIGHT OPEN LAYOUT - Walls of glass bring the outdoors in, filling the home with sunshine and stunning water views. ELEVATOR - Effortless access to main living levels from the three car garage. CHEF’S DREAM KITCHEN - High-end appliances, custom cabinetry, and an oversized island ready for gourmet meals and lively gatherings. LUXURIOUS SUITES - Owner’s retreat with a private balcony, spa-inspired bath, and dual walk-in closets. MOVIE ROOM - Your own private theater for cozy nights in. OUTDOOR OASIS - infinity pool, spacious patio, and lush landscaping for poolside lounging or sunset soirees. All this just steps to your DEEDED BEACH ACCESS and minutes from the world-class dining, shopping, and cultural treasures of St. Armands Circle and Downtown Sarasota. Whether you’re dreaming of a full-time Florida home or a seasonal escape, 550 Yardarm Lane delivers the ultimate Longboat Key lifestyle.
Listing is courtesy of: QUEST PROPERTIES INC (941-504-1111)
Listing Agent: Melanie Russell (941-879-5882)
524 HALYARD LN, LONGBOAT KEY, FL 34228
$5,495,000235 Days on yellowkey MLS ID: A4663499
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3737 Built: 2025Monthly Fee: $21 Tax: $17,932 (2024)Community: Country Club Shores IvSpa: YesSingle Family
Taxes:$17,932
Middle School: Brookside Middle
Remarks: One or more photo(s) has been virtually staged. Only ONE BUYER will be the FIRST OWNER! Crafted by an award winning design team, this brand-new coastal contemporary waterfront residence awaits you in the exclusive Country Club Shores community on South Longboat Key. Designed for high performance and easy maintenance, this rock-solid, all block two-story residence with a private elevator provides peace of mind while capturing the essence of easy island living. A fluid open-concept layout is ideal for seamless indoor-outdoor waterfront entertaining. Soaring ceilings with impressive transom glass over casement windows and 10-foot tall sliding glass doors illuminate the interiors with natural light. At the heart of the home, a thoughtfully created gourmet kitchen and wet bar are a showpiece, featuring tailor made modern shaker doors and full panel rift-cut white oak cabinetry. Striking elements include the waterfall island and a dramatic ceiling-height hood, both wrapped in exotic natural Quartzite. A full suite of Wolf & Sub-Zero appliances includes twin 30" refrigerator & freezer towers, an 18" wine tower, under counter beverage centers, wall ovens and a contemporary gas cooktop. The first-floor primary suite is a serene retreat featuring a warm wood-slatted ceiling, expansive glass and a gorgeous bathroom with a freestanding soaking tub, dual vanities and textured porcelain tile accents. An inviting staircase leads to an elevated private home office with a half bathroom. The second floor features a game room with a wet bar and three en-suite guest bedrooms, offering comfort and flexibility complemented by a 30 foot covered balcony overlooking the tranquil water views. Energy-efficient features include variable speed 17 SEER HVAC systems, spray foam insulation and hurricane impact-resistant ES windows and doors. Control4 Smart Home technology provides many conveniences. A host of pre-wired systems—including sound, security, shades and EV charging—can be customized to the buyer's selections. Outside, a brand-new, 100-foot-long, extra-wide seawall protects a resort-style paradise! A four piece French patterned Crema Nova marble decking surrounds the 40-foot linear pool with in-water bench seating, a large sun shelf and a 12 foot wide spa. An elevated lanai with detailed ceilings features an outdoor kitchen, complete with Naturkast marine grade cabinetry, under counter refrigerator and a 42 inch built-in grill offering the perfect retreat for alfresco dining and poolside lounging. All this is just minutes from the extraordinary shopping and dining of St. Armands Circle, the cultural richness of downtown Sarasota, and the world-renowned Gulf beaches of Longboat Key. Seller is offering generous allowances towards custom closets and boat dock design providing an opportunity for the buyer to personalize these features to meet their sytle and preferences!
Listing is courtesy of: HUNT BROTHERS REALTY, INC. (941-388-7017)
Listing Agent: Rob Hunt, Jr (941-232-2431)
828 BAYPORT WAY #828, LONGBOAT KEY, FL 34228
$900,00011 Days on yellowkey MLS ID: A4689635
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1983 Tax: $5,880 (2025)Community: Bayport Bch & Ten Ph FCondo
Taxes:$5,880
Remarks: Bayport Beach & Tennis Club is a true Longboat Key Gulf-to-Bay community, set across 27 acres of beautifully maintained gardens with 1,200 feet of pristine private Gulf beach. Designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture. Bayport is celebrated for its award-winning, timeless design. Residences like this rarely come to market. This first-floor, fully renovated unit showcases elevated designer finishes throughout. A picture-window screened patio opens to an expansive lanai, surrounded by lush, tropical landscaping; creating a seamless indoor-outdoor living experience. The modern kitchen features Caesarstone “concrete” quartz countertops, an induction cooktop, built-in oven, and custom cabinetry designed for both style and functionality. Each bathroom evokes a five-star resort experience, with thoughtfully curated custom details and designer lighting in both the baths and dining area. All windows and the patio slider have been upgraded to hurricane-impact glass for added peace of mind. The home also features air purification paint for enhanced interior air quality. One under-building parking space is included, along with a private, locked storage closet which is perfect for bikes and beach gear. Beyond the beach, residents enjoy meticulously maintained nature trails, lushly landscaped grounds, and abundant wildlife. Just steps from the residence, the well-appointed clubhouse features a Junior Olympic-sized heated pool, four Har-Tru tennis courts, a fitness center, and more. Bayport is also known for its vibrant social and recreational lifestyle. Water enthusiasts will appreciate the secluded fishing pier extending into Sarasota Bay. An ideal setting to fish, take in the sunrise, watch manatees glide by, or egrets wading through the mangroves. Paddleboard and kayak launch and storage areas are conveniently located on-site. Residents enjoy easy access to local dining, a nearby supermarket, pharmacy, and charming boutique shops. Just moments away, Bayfront Park offers a popular pickleball program, dog park, and a variety of bayside activities. The Longboat Key Club is also nearby, offering private access to championship waterfront golf, boating, and an array of leisure amenities. Within minutes, you’ll find the renowned St. Armands Circle, known for its exceptional shopping and dining. From there, cross the iconic Ringling Bridge into downtown Sarasota, celebrated for its world-class theater, culture, and culinary scene. Offered by private appointment. Inquire to experience Bayport’s timeless coastal living firsthand.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Alexis Smith-Frady (352-225-1724)
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