Location: Longboat Key
Do Not Show Listings
1065 GULF OF MEXICO DR #302, LONGBOAT KEY, FL 34228
$619,000577 Days on yellowkey MLS ID: A4624142
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1392 Built: 1981 Tax: $4,571 (2023)Community: Beachplace IiiCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,571
Elementary School: None
High School: None
Tax Year: 2023
Middle School: None
Remarks: One of a kind, never rented, ready for a new owner to put their touches on this opportunity! Unit has endless views. Come look, Being able to rent this unit, by the month, twelve times a year, that offers our beautiful GULF BEACH within seconds of the front door is incredible! Our third floor views are breathtaking, yet fully protected from the elements. Our Building is quiet, but close to BEACHPLACE amenities! Owners are motivated to sell and we can give you a complete tour when you visit. Also new HURRICANE Windows recently added. BONUS TWO PARKING SPACES, ONE IN GARAGE,ONE OUTSIDE! BEST VALUE IN BEACHPLACE BY FAR> GO COMPARE!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: James Weingart (440-623-9068)
3070 GRAND BAY BLVD #644, LONGBOAT KEY, FL 34228
$799,000Listed 04/20/2026 10:55AM MLS ID: A4690677
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1329 Built: 1995 Tax: $6,324 (2025)Community: Grand Bay 6Condo
Taxes:$6,324
Tax Year: 2025
Remarks: Penthouse-Level Condo at Grand Bay – Longboat Key Experience luxury living in this beautifully appointed penthouse-level residence at Grand Bay, located behind the gates of Bay Isles on Longboat Key. This spacious 2-bedroom, 2-bath condo offers an open and airy floor plan with stunning east-to-west exposure, capturing both sunrise and sunset from dual balconies with sweeping views of Sarasota Bay, the city skyline, and the golf course. As a penthouse-level home, it also features an added ceiling height of one foot, enhancing the sense of space and light throughout. Both bedrooms are en-suite, with the primary suite featuring dual closets (including one walk-in) and luxurious marble vanities in the bath. The home showcases elegant bamboo flooring in the main living area, marble tile in the bathrooms, and plush carpet in the bedrooms. Floor-to-ceiling sliding glass doors at both ends of the unit flood the space with natural light. The chef’s kitchen is equipped with a Sub-Zero refrigerator, Blue Pearl granite countertops, a breakfast bar, and an in-kitchen laundry room. Recent upgrades include a new AC system in 2021 and a water heater in 2020. The residence also comes with two deeded parking spaces and a private garage-level storage locker, and it is offered furnished for immediate enjoyment. Grand Bay’s exceptional amenities include 24-hour guard-gated Bay Isles entry, an additional Grand Bay gated entrance, secure coded lobby access, on-site property management, and a pet-friendly environment. Residents enjoy two resort-style pools, a state-of-the-art fitness center, tennis courts, and membership to the Bay Isles Beach Club. There are no current or pending assessments. Enjoy the perfect blend of luxury, privacy, and convenience in one of Longboat Key’s premier waterfront communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Nicole Hammons-Dovgopolyi (941-966-8000)
2110 HARBOURSIDE DR #523, LONGBOAT KEY, FL 34228
$699,00054 Days on yellowkey MLS ID: A4682869
REDUCED by $26,000 (3.6%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988 Tax: $5,680 (2025)Community: Fairway BaySpa: NoCondo
Taxes:$5,680
Remarks: Experience elevated coastal living in Bay Isles at The Atrium, where this stunning 3-bedroom, 2-bath residence showcases breathtaking views of Sarasota Bay that truly steal the show. From the moment you step inside, you are welcomed by sweeping water views that stretch for miles, sparkling blue during the day and glowing with unforgettable sunset colors in the evening. The expansive private terrace serves as an extension of your living space, offering the perfect setting for morning coffee as boats drift by, sunset dinners, or simply relaxing while taking in the panoramic Bayfront scenery. The spacious primary suite is a serene retreat with direct terrace access, allowing you to wake up each morning to breathtaking water views, while the spa-like primary bath provides a peaceful escape designed for ultimate relaxation. Ideally located just minutes from St. Armands Circle and vibrant downtown Sarasota, you'll enjoy world-class dining, boutique shopping, and cultural attractions right at your fingertips. Residents of Bay Isles enjoy exclusive access to the private Bay Isles Beach Club, featuring a pristine Gulf-front beach, barbecue grills, volleyball, and covered picnic tables. The Atrium offers exceptional amenities including tennis and pickleball courts, a clubhouse, heated pool, fitness center, and on-site management. This is your opportunity to live in paradise on Longboat Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Caroline Mitchell (913-787-3131)
4900 GULF OF MEXICO DR #203, LONGBOAT KEY, FL 34228
$689,000166 Days on yellowkey MLS ID: A4670932
REDUCED by $10,000 (1.4%) on 04/08/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1325 Built: 1975 Tax: $8,395 (2025)Community: Windward Bay AmdSpa: NoCondo
Taxes:$8,395
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: IN THE COVETED "B" BUILDING, A STRATEGIC PRICE REFINEMENT NOW POSITIONS THIS EXCEPTIONAL RESIDENCE AS THE MOST COMPELLING OFFERING AT WINDWARD BAY! A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend. Wake up to spectacular sunrises over the sparkling bay and unwind with mesmerizing sunsets on the Gulf, directly across the street. Watch playful dolphins, jumping fish, gentle manatees, and vibrant Florida birdlife from your Florida Room or while preparing meals in your updated kitchen overlooking the shimmering waters. Your primary suite is a serene waterfront retreat, perfect for moonlit nights and sunrise mornings. Every detail of this condo has been thoughtfully designed to create a lifestyle of tranquility and relaxation, including remote controlled blinds in the Florida Room. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. The Windward Bay Association has been busy with a multitude of improvements and updates in the last few years including: Brand new roofs, resealing the buildings bayfront exteriors and painting of all the midrises in 2023/2024. Private roads were repaved and a new 1/2 mile long salt-tolerant privacy hedge was planted in October 2025. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced and 2026 Condo Fees only increased by $13 a month. This is more than a home—it’s a lifestyle. Experience the beauty, serenity, convenience, and the maintenance free life you’ve always dreamed of. GREAT NEWS, PAST CAPITAL IMPROVEMENT ASSESSMENTS WERE PAID IN FULL BY SELLER, NOT ADDED TO MONTHLY DUES! Schedule your private showing today and make paradise yours!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Debby Mccaig (941-544-1713)
2016 HARBOURSIDE DR #317, LONGBOAT KEY, FL 34228
$895,00053 Days on yellowkey MLS ID: A4683894
0 Days Off yellowkey (back on 3/11/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 1984 Tax: $5,815 (2025)Community: Fairway Bay 2 Ph 1Spa: YesCondo
Taxes:$5,815
Remarks: Under contract-accepting backup offers. Set in one of Fairway Bay’s most desirable corner locations, this first living level 2BR/2BA walk-down residence offers bay views and easy island living. Fully renovated, it provides the move-in-ready condition many buyers want. From the entry, the quality of the renovation is clear. Solid wood floors run throughout the residence and complement the Sarasota Bay views. The kitchen features quartz countertops, white cabinetry with a glass-panel accent built-in, stainless steel appliances, generous storage, an eat-in nook, and a breakfast bar open to the living area. The living room includes custom built-ins, a coffered ceiling with recessed lighting, and a wall of sliders with views of the lagoon, mangroves, sailboats, walking paths, and the downtown Sarasota skyline. The sliders open to a spacious open and covered patio with walk-down access to the community amenities. The guest bedroom is privately positioned and generously sized, with an en-suite bath for visitors. The primary suite includes a slider to the patio, a spacious closet, and a large bath with a makeup vanity, walk-in shower, and separate water closet. Located within Bay Isles, Fairway Bay residents benefit from Bay Isles’ two 24-hour guard-gated entrances and deeded Gulf-side beach access through the Bay Isles Beach Club, a private beach area for Bay Isles residents only with beachside pavilions/tiki huts, picnic areas, barbecue grills, and restroom facilities. Fairway Bay amenities include a community pool, tennis courts, and fitness facilities, offering convenient options for recreation, exercise, and everyday enjoyment within the neighborhood. Longboat Key Club memberships are available separately, offering access to golf, tennis, dining, and social offerings. Deepwater slips are also available separately at the Longboat Key Club marina, providing a convenient option for boating access. Fairway Bay is pet friendly.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
4960 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228
$649,90088 Days on yellowkey MLS ID: A4679160
REDUCED by $10,000 (1.5%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1523 Built: 1975 Tax: $7,738 (2025)Community: Windward Bay AmdCondo
Taxes:$7,738
Remarks: SELLER SAYS “SELL!” Unbeatable opportunity at $649,900 for a full Bayfront Waterview, corner end-unit on Longboat Key. Exceptionally priced below market value—this residence represents the lowest-priced Bayfront end unit in the highly desirable community of Windward Bay, in over 5 years. A compelling price point, providing rare access for those seeking to own a premium waterfront residence at an extraordinary price. Encompassing 1,523 square feet, this stylishly furnished, two-bedroom, two-bath residence is thoughtfully designed to showcase uninterrupted panoramic Bay views from every room. Natural light fills the open living and dining areas, where expansive windows frame ever-changing Bay views from sunrise through the evening’s sunset. The remodeled 2024 kitchen opens seamlessly to the main living area and features recently completed upper cabinetry and a sophisticated yet functional layout ideal for both relaxed daily living and entertaining. Recently acquired “chic” French doors in both bedrooms open to the Florida Room, a signature feature for Longboat Key residences, offering additional living space to enjoy morning light and serene Bay vistas. The spacious primary suite includes a private en-suite bath and a generous walk-in closet, providing comfort, supporting everyday living, and abundant storage. “Pet Friendly” Windward Bay is a well-established waterfront community known for its mature landscaping, waterfront setting, resort-style amenities, a strong proactive association with solid reserves, and an enduring reputation as one of Longboat Key’s most welcoming communities. (Attributes that continue to attract owners who value lifestyle as much as long-term stability.) The Milestone Inspection and Capital Reserve Study are complete. Windward Bay’s Monthly Condo Fees for 2025 were actually reduced and for 2026 only increased slightly by $13 a month, demonstrating a financially healthy Condo Association. Offered furnished and move-in ready, this corner end-unit provides flexibility as a full-time residence, seasonal retreat, or investment opportunity. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. An uncommon offering distinguished by exceptional value, location, and the timeless appeal of gulf to bay living. Private showings are available for those seeking a rare chance to own a premium waterfront residence at an extraordinary price.
549 SUTTON PL #t 19, LONGBOAT KEY, FL 34228
$329,00095 Days on yellowkey MLS ID: P4937545
3 Days Off yellowkey (back on 4/20/2026)
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1248 Built: 1972Monthly Fee: $1,708 Tax: $5,711 (2024)Community: Sutton PlaceCondo
Taxes:$5,711
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Across from the beach walk to sunsets at your private beach pavilion! This spacious, private two-story townhome with an enclosed garage is ideally positioned in a prime, quiet location within the community set away from incoming traffic. Updated, fully furnished, and truly turnkey. Enjoy a screened in back porch surrounded by lush landscaping, offering a peaceful private retreat. The home features both front and rear entrances, a kitchen with island seating, and tile flooring throughout the entire first floor. Large TVs with speaker systems are located both downstairs and upstairs. The enclosed garage includes an additional walk-in shower perfect after beach days along with a washer and dryer. Ample parking is available for residents and guests. Located at Sutton Place on Longboat Key, this mid-island community offers the best of coastal living with deeded beach access just steps away, plus a private boat marina and expansive Sarasota Bay views. Residents enjoy two heated community pools (one overlooking the marina), a clubhouse, kayaking access, BBQ areas, and beautifully maintained grounds. Bike to Bayfront Park for pickleball or tennis, visit nearby dog parks, or simply relax and enjoy both the Gulf of Mexico and Sarasota Bay right outside your door. Highlights: • Deeded beach access across the street • Enclosed garage + outdoor shower • Fully furnished & turnkey • Two heated community pools • Private marina & bay views • Quiet, private location within the community
Listing is courtesy of: SOUTHERN CHARM REALTY & INVESTMENTS LLC (502-680-1491)
Listing Agent: Chelsey Bast (502-680-1491)
4440 EXETER DR #106, LONGBOAT KEY, FL 34228
$649,00052 Days on yellowkey MLS ID: D6146366
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1970 Tax: $9,714 (2024)Community: Longboat HarbourCondo
Taxes:$9,714
Remarks: Welcome to Longboat Harbour, a gated waterfront community offering resort-style living on beautiful Longboat Key. This first-floor corner unit, N-106, features two bedrooms, two baths, and an assigned covered carport — all set against unparalleled views of Sarasota Bay and the Intracoastal Waterway. Step inside to find ceramis plank flooring throughout and a light-filled, open layout designed to maximize both comfort and scenery. The bright kitchen offers a convenient pass-through to the dining area and living room, allowing you to stay connected with guests while preparing meals. The spacious living room is lined with windows facing the water, delivering breathtaking sunrise views each morning. Sliding glass doors from both bedrooms open to a tiled three-season lanai, complete with additional sliders that lead directly to the outdoors — perfect for embracing Florida’s coastal lifestyle. Both bathrooms feature elegant granite countertops for durability and easy maintenance. ?? Exceptional Community Amenities Include: Private Beach Club with Parking, Four heated pools, Tennis and pickel balls courts, Fitness center, Clubhouse, On-ste manager and boat docks. (Available on a first come basis for sail or power boats) Whether you’re seeking a full-time residence, seasonal retreat, or investment opportunity, this waterfront gem offers the perfect blend of luxury, comfort, and active coastal living.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Roger Richmond (941-456-6281)
4561 GULF OF MEXICO DR #202, LONGBOAT KEY, FL 34228
$2,750,000129 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
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)
603 LONGBOAT CLUB RD #402N, LONGBOAT KEY, FL 34228
$1,250,000167 Days on yellowkey MLS ID: A4670556
1 Days Off yellowkey (back on 4/1/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1458 Built: 1970 Tax: $13,618 (2025)Community: Longboat Key TowersSpa: YesCondo
Taxes:$13,618
Remarks: Under contract-accepting backup offers. Nestled behind the exclusive gates of the Longboat Key Club, Longboat Key Towers stands as one of the island’s most distinguished Gulf-front communities. Within the north tower, this elegant fourth-floor residence captures breathtaking views from sunrise to sunset — with two expansive balconies overlooking the shimmering Gulf of Mexico to the west and the rolling greens and bay waters to the east. The living and dining areas frame the Gulf like a work of art, with floor-to-ceiling picture windows that make you feel as though you’re floating above the shoreline. A thoughtfully designed kitchen offers generous cabinetry, pantry storage, a full suite of appliances, and a convenient service entrance. A gracious double-door entry opens to a welcoming foyer that leads to the guest quarters and bath. The spacious primary suite features a walk-in closet, a separate vanity area, and a private bath, with both bedrooms sharing access to the eastern balcony for tranquil morning views across the golf course. In this secure, modernized building, residents enjoy covered and guest parking, private storage, and a breezeway that connects both towers — enhancing the sense of community. Amenities abound: a Gulf-front heated pool and spa surrounded by a paver-brick sundeck, a well-equipped fitness center, and attentive on-site management and staff. A $12 million renovation in 2008 brought new impact-rated windows, roofing, exterior resurfacing, spa and pool enhancements, paver decks, and refreshed lobbies and fitness facilities. The 2015 plumbing project further modernized the infrastructure with new domestic water piping and lining. Every detail has been considered, offering peace of mind and timeless appeal. This is truly an owner’s retreat. Just beyond your door lies The Links on Longboat, a spectacular seaside golf course reimagined for today’s player — a par-71 layout spanning 6,748 yards of beautifully maintained greens. Membership options at the Longboat Key Club provide access to a second Harbourside course, world-class tennis, fine and casual dining venues, a full-service spa and fitness center, club gatherings, concierge services, and The Longboat Key Club Moorings — a deep-water marina offering exclusive affiliation opportunities. Living on Longboat Key is more than a lifestyle — it’s a privilege. With fine dining, boutique shopping, and cultural attractions just minutes away at St. Armands Circle and downtown Sarasota, this location perfectly blends resort-style living with everyday convenience.
Listing Agent: Judy Kepecz-Hays (941-587-1700)
7105 GULF OF MEXICO DR #21, LONGBOAT KEY, FL 34228
$895,000217 Days on yellowkey MLS ID: A4665082
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1170 Built: 1974 Tax: $10,071 (2024)Community: LongbeachSpa: NoCondo
Taxes:$10,071
Remarks: Gulfside Condo on north Longboat Key with direct beach access: This 2-bedroom, with bonus room, second floor condo offers the island lifestyle you've been searching for—a waterfront community, stunning sunset views from the lanai, and steps to the beach. Located in Longbeach Condo community on Longboat Key, this turnkey furnished, coastal Florida condo features 2 bedrooms, 2 bathrooms,and a bonus room currently used as a den. The comfortable floorplan features a bonus room for bunks, an office, or a reading room, a wide galley kitchen with Corian counters and tossed marble tile backsplash, in-unit washer/dryer, tile floors throughout, and a private balcony with views of the Gulf. At 19.5 foot base flood elevation, this unit was well above the storm surge of previous hurricanes. Longboat Key Living means beach access, world-class golf courses, world class tennis and waterfront dining just minutes away. The Longbeach Condo community offers 9.2 acres of gulf front, beach property, amenities like heated pool, club house, open parking, private beach access, kayak storage and private tennis. You're 15 minutes to St. Armands Circle shopping, 20 minutes to downtown Sarasota, and close to world-class fishing charters from Cortez Fishing Village. This barrier island property is perfect for full-time Florida living, a vacation home, a snowbird retreat or investment rental property. Rental history/projections available. The location puts you near Coquina Beach, Marina Jack, and easy access to Sarasota-Bradenton International Airport. Nationally ranked medical facilities located within minutes and all LBK first responders are EMTs!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Diana Kryszak (941-993-4078)
545 SANCTUARY DR #B204, LONGBOAT KEY, FL 34228
$2,799,000179 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 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.
5320 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$1,150,000198 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
$1,795,00098 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
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
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
$585,00046 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
$1,395,000157 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
$1,495,00076 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
$1,100,000227 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
$549,900185 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)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.