Location: Longboat Key
Do Not Show Listings
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,395
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
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)
600 SUTTON PL #B302, LONGBOAT KEY, FL 34228
$500,0003 Days on yellowkey MLS ID: A4690036
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1132 Built: 1973Monthly Fee: $1,642 Tax: $7,415 (2025)Community: Sutton PlaceSpa: NoCondo
Taxes:$7,415
Middle School: W.D. Sugg Middle
Remarks: Enjoy the best of the Longboat Key lifestyle in this beautifully updated 2-bedroom, 2-bath waterfront condo at Sutton Place, offering a rare Gulf-to-Bay experience with Sarasota Bay views and PRIVATE DEEDED BEACH ACCESS to a Gulf-front beach just across the street. This light and bright residence features a spacious, open floor plan with quality finishes throughout, including porcelain tile and engineered hardwood flooring for a clean, modern, low-maintenance feel. The updated kitchen is both stylish and functional, showcasing quartz countertops, a mother-of-pearl mosaic backsplash, tray ceiling, and stainless steel appliances. The primary suite includes a fully remodeled bathroom with quartz counters, custom glass shower, and marble tile, while the guest bathroom features granite countertops and a vessel sink. A glass-enclosed and screened lanai extends the living space, bringing in natural light and allowing you to enjoy peaceful bay breezes year-round. Recent upgrades include newly installed IMPACT RESISTANT WINDOWS & DOORS, providing added safety, energy efficiency, and peace of mind. Updated lighting was also added in the living area This residence is being sold TURNKEY FURNISHED, making it truly move-in ready or ideal as a second home or investment property. As an added bonus, the sale includes four brand new KAYAKS—perfect for enjoying the community’s direct bay access and embracing the waterfront lifestyle. Sutton Place is a highly desirable waterfront community offering exceptional amenities, including deeded Gulf beach access with pavilion, gated parking, showers, and picnic areas, TWO heated bayside POOLS, BBQ grills, BOAT SLIPS (first-come, $300/year), kayak storage and launch, fishing dock, clubhouse, and covered parking with ample guest spaces. The community is pet-friendly (2 pets up to 25 lbs each), not age restricted, and allows two rentals per year with a one-month minimum after the first year of ownership, making it ideal for both personal use and investment. Recent community improvements include new roofs, exterior repainting, and resealing (2023), along with a completed milestone inspection. Ideally located mid-key, close to Bayfront Park, dining, shopping, and just a short drive to Anna Maria Island, St. Armands Circle, and downtown Sarasota. Don’t miss this opportunity to own a piece of paradise on Longboat Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Debbie Mchardy (941-960-6099)
5655 GULF OF MEXICO DR #A107, LONGBOAT KEY, FL 34228
$799,00010 Days on yellowkey MLS ID: A4687549
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1274 Built: 1975Monthly Fee: $1,164 Tax: $3,185 (2025)Community: Cedars West Of Longboat IncCondo
Taxes:$3,185
Elementary School: None
High School: None
Middle School: None
Remarks: Experience the best of Gulf-front living and gorgeous views in this move-in-ready, two-bedroom, two-bath waterfront condominium, perfectly positioned in an elevated community just steps from the beach. This home is in impeccable condition and is designed for relaxation, with a seamless blend of comfort, style and convenience. It's being sold turnkey with lovely furnishings. The kitchen features new Samsung stainless steel appliances, plenty of counter space, and a comfortable sitting area. An open floor plan with a large living room, remote-controlled sunshades and three-panel impact sliding glass doors opens to an inviting screened lanai with a tropical ceiling fan, blurring the lines between indoor and outdoor living. There are ceiling fans in every room. The primary suite offers a large bath with a separate water closet and a huge walk-in closet. There are also impact sliders leading out to the lanai with a view of the Gulf. The guest suite is spacious with lots of closet space. The laundry is neatly tucked away and features Bosch machines. If you love the beach and enjoy stunning sunsets, Cedars West is really the perfect place to live. This location is walking distance to our local restaurants (Lo-Key, Harry's and Hugos), convenience shopping and all the amenities you’ll need to enjoy life here on Longboat Key. This community has tennis, a heated pool, BBQ area, bike racks, and kayak storage. Cedars East, just across the street, offers tennis membership with a world-class facility. This financially sound community offers peace of mind with a new roof and no assessments planned. With a liberal rental policy allowing up to 26 rentals/year, this property presents an exceptional investment opportunity while still offering the flexibility to enjoy your own beach getaway. There is a locking owner's closet in the unit. You have to see this home to really appreciate how special it is.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Judy Mitchell (941-275-6838)
4500 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$739,00025 Days on yellowkey MLS ID: A4685838
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1975 Tax: $2,843 (2025)Community: Windward Bay AmdCondo
Taxes:$2,843
Remarks: GORGEOUS BAYFRONT PENTHOUSE VIEWS Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living. Schedule your private showing today.
Listing Agent: Marcela Terrell (941-929-3010)
3240 GULF OF MEXICO DR #B402, LONGBOAT KEY, FL 34228
$895,00038 Days on yellowkey MLS ID: A4686024
REDUCED by $10,000 (1.1%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1505 Built: 1975 Tax: $8,208 (2025)Community: PortobelloSpa: NoCondo
Taxes:$8,208
Elementary School: Southside Elementary
Remarks: TURNKEY Furnished Portobello condo with Deeded Beach Access! TWO Balconies with Sunsets AND Sunrises included! Enjoy Beach and Bayou water access! Rarely available end unit with two balconies and lots of privacy and natural lighting. The front open balcony has unobstructed Gulf views whilst the rear balcony is glassed in with sliders/screens and faces the Bayou. This 4th Floor condo has elevator access, 1 owners storage locker, ample in unit storage and 1 assigned parking space. Condo fee includes Water, Sewer, Trash, Cable/Internet, Pest Control, on site Maintenance and Exterior Insurance. Well established social community with Community Pool, Clubhouse, Tennis Courts, Kayak storage/launch, Fishing Pier, BBQ area and ELEVATED mature landscaping. This spacious floorplan is one of the larger floorpans in the community providing you with list and bright spaces, tons of closet space and even a bonus study/den area to use as you please! Stacked Washer/Dryer located near the hallway 2nd Bathroom which has been renovated. Beautifully upgraded Kitchen with high quality cabinetry and 4 storage closets for all your pantry, cleaning and large cooking items. The Primary Bedroom has the most wonderful private bayou water views! Attached en suite full bathroom with lots of counter space. Secondary bedroom has its own separate balcony entrance. This community is located a short drive away from Publix, CVS, banks, Post office, nail salons and Golfing! New development nearby is bringing more shopping and dining! Don't miss this opportunity to own in the sough after Portobello community!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Monica Desomma (202-427-4328)
6750 GULF OF MEXICO DR #163, LONGBOAT KEY, FL 34228
$500,00049 Days on yellowkey MLS ID: A4683547
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1970 Tax: $4,337 (2024)Community: Whitney BeachCondo
Taxes:$4,337
Tax Year: 2024
Remarks: In the sought-after Whitney Beach community on Longboat Key’s peaceful north end, this beautifully renovated two-bedroom, two-bath end unit residence offers 1,449 square feet of coastal contemporary living with tranquil water views over protected Bishop’s Bayou. Enjoy serenity of a coastal inlet sheltered from constant boat traffic of the Intracoastal Waterway, where dolphins and manatees glide past your rear Florida room, a front-row seat to nature. The versatile floor plan includes spacious bedrooms with en-suite baths (showers only), a bright 9-by-14-foot flex space with abundant windows where the washer and dryer connection is located, plus an additional 8-by-3-foot storage area. The kitchen features quartz countertops, stainless steel GE appliances and a water view that enhances everyday living. Tasteful coastal selections, a light palette and additional end unit windows create an airy, open feel throughout, complemented by storm-resistant windows for added peace of mind. Whitney Beach offers resort-style amenities including two pools, tennis court, barbecue stations, kayak storage and launch, lush recreational paths and deeded private beach access directly across the street to the turquoise Gulf waters. Boat slips are available when offered, with annual dock fees of $600 for slips up to 33 feet and $480 for slips up to 24 feet. Sublets are available. Two pets are welcome with no weight restrictions. Rentals are permitted with a one-month minimum. An exceptional opportunity to enjoy bay-to-beach living in one of Longboat Key’s charming waterfront communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Karen Whitaker (941-724-6969)
1445 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$1,195,00052 Days on yellowkey MLS ID: A4684021
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2092 Built: 1982 Tax: $11,749 (2025)Community: Players Club IiiSpa: YesCondo
Taxes:$11,749
High School: Booker High
Middle School: Booker Middle
Remarks: Step into this highly desirable corner residence featuring three bedrooms, three full baths, and an expansive 36’ x 11’ sunroom at The Players Club. You’ll immediately be drawn to the impressive 31-foot balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. Inside, the sun-filled kitchen is thoughtfully designed with custom cabinetry and a built-in breakfast table that expands both workspace and storage. It flows seamlessly into the main living and dining areas, creating a warm and open environment for entertaining or daily living. Just off the kitchen, elegant French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The owner’s suite provides a private sanctuary with a spa-inspired bathroom featuring a soaking tub, separate glass-enclosed shower, dual vanities, and a spacious walk-in closet. The second bedroom functions as a true secondary master, complete with dual sinks, a full vanity, and a fitted walk-in closet, offering comfort and privacy for family or visitors. A third bedroom adds flexibility for guests, workspace, or hobbies. A unique feature of this residence is the private garage, offering rare security and convenience for residents, plus an additional covered parking space underneath the building for extra guest or secondary vehicle use. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves. Just minutes from St. Armands Circle, downtown Longboat Key, and Longboat Key Club, with championship golf, premier tennis, and a deep-water marina, this corner residence blends privacy, convenience, and resort-style coastal living. Units with this versatile layout and resort-ready features are highly sought after. Offered partially furnished. Seller is willing to discuss a subsidy on the quarterly condominium fee for reserve increase over the next two years!
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
4310 FALMOUTH DR #102, LONGBOAT KEY, FL 34228
$660,00087 Days on yellowkey MLS ID: A4679011
REDUCED by $5,000 (0.8%) on 04/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969Monthly Fee: $1,410 Tax: $6,739 (2024)Community: Longboat HarbourCondo
Taxes:$6,739
Remarks: Exceptional value for a Longboat Key condo with private beach access. Enjoy deeded Gulf access with a residents-only community beach house featuring bathrooms, indoor/outdoor showers, seating, cabana space, and parking—your personal gateway to Gulf Coast living. Experience exceptional bayfront living at 4310 Falmouth Drive, Unit 102, located in the sought-after Longboat Harbour community on Longboat Key—a premier coastal city and barrier island along Florida’s Gulf Coast, renowned for attracting year-round residents, second-home owners, seasonal residents, and visitors seeking a refined, upscale seaside lifestyle. This A-Building, direct bayfront residence captures full Sarasota Bay views from the kitchen, dining area, living room, enclosed lanai, and primary bedroom—offering a front-row seat to sunrise skies, passing boats, dolphins, manatees, eagles and all kinds of exciting wildlife just 40 feet from the tranquil water vistas. Thoughtfully updated, the home features luxury vinyl flooring, upscale LG quartz Viatera Rococo countertops in the kitchen and both bathrooms, and soft-close drawers and custom cabinetry throughout. The spacious primary suite includes double vanities and a beautifully updated walk-in shower, while the guest bath also offers a walk-in shower with quartz finishes. Significant capital improvements provide peace of mind, including new hurricane-rated windows and sliders (2024, Cat5), HVAC (2021) with approximately 8 years remaining on a 12-year warranty, and a water heater (2023). The enclosed lanai expands usable living space while maintaining sweeping Sarasota Bay views. Offered fully furnished for a seamless, move-in-ready bayfront lifestyle. Longboat Harbour is a gated, resort-style community offering an impressive array of amenities, including four heated pools, tennis and pickleball courts with active player groups, fitness center, sauna, meeting rooms, billiards, putting green, woodworking shop, kayak storage, shuffleboard, locker rooms, fishing piers, two community grills, on-site management, and a protected harbor. Boat slips are available to members of the Longboat Harbour Yacht Club (subject to availability). Enjoy the best of island living with private deeded beach access just a short walk or drive across the street—complete with seating, chair storage, cabana, restrooms, indoor and outdoor showers, parking, and a convenient car-wash area. Additional features in the condo include washer and dryer connections in a hall closet and assigned covered carport parking with abundant guest spaces nearby. In the living room, open the sliders to seamlessly expand your indoor–outdoor living space, or keep them closed and enjoy the patio as an enclosed lanai—then open the glass sliders to let in refreshing coastal breezes and salt air. Located just 7.5 miles north of St. Armands Circle, and a short drive to downtown Sarasota’s Arts District, world-class dining and shopping, with Sarasota-Bradenton International Airport nearby. Direct Sarasota Bay views and private deeded Gulf beach access make this exceptional residence the ultimate Longboat Key lifestyle opportunity.
Listing is courtesy of: MARCUS & COMPANY REALTY (941-932-8550)
Listing Agent: Kerre Allman (941-909-3095)
600 SUTTON PL #104B, LONGBOAT KEY, FL 34228
$545,000399 Days on yellowkey MLS ID: A4644920
REDUCED by $25,000 (4.4%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1973 Tax: $6,737 (2024)Community: Sutton PlaceCondo
Taxes:$6,737
Remarks: Incredible FULL BAY VIEW! This tranquil and beautifully renovated island retreat located in the beach to bay community of Sutton Place offers that and so much more. This 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous, remodeled kitchen is open to the living/dining area across an expanse of granite that includes a custom made dining table with lots of storage underneath and seating all around! Porcelain tile flooring makes the journey from one room to another a seamless and beautiful transition. These smart owners have converted the lanai into finished square footage and it is the perfect spot to enjoy a morning coffee or an evening beverage while watching the fish jump or the birds fly by. They also upgraded to IMPACT RESISTANT SLIDING DOORS AND WINDOWS throughout. The Primary bedroom has this same gorgeous view and a renovated ensuite bath. The once walk-in closet was converted to a small office space, (which could easily be changed back) but it’s current use is rather genius. When guests are not in town, the 2nd bedroom is another tranquil space to enjoy. Did I mention this is a 2 pets friendly community?! Sutton Place also offers its own PRIVATE BEACH CLUB and includes an abundance of amenities including 2 pools, a clubhouse, and an onsite marina with slips for a nominal fee of only $300 per year. The community recently completed a number of updates including repainting, reroofing and passing the milestone inspection and securing a 10 year certification. This owner has paid for all of those upgrades in full. The unit is being offered furnished with exceptions. Here you will find a remarkable quality of laid-back island life but if you're ready for more, enjoy the multitude of restaurants, shopping and the cultural mecca of downtown Sarasota, all within a short drive away.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
5055 GULF OF MEXICO DR #331, LONGBOAT KEY, FL 34228
$895,000164 Days on yellowkey MLS ID: A4670624
REDUCED by $90,000 (9.1%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $5,337 (2024)Community: Club LongboatSpa: YesCondo
Taxes:$5,337
Remarks: One or more photo(s) has been virtually staged. Welcome to your coastal retreat in paradise — a stunning third-floor waterfront residence in Club Longboat Beach and Tennis, offering expansive Gulf views and one of the largest floor plans in the community. This exceptional 2-bedroom plus 3rd bedroom/study layout perfectly blends elegance, comfort, and functionality, ideal for full-time living or as a refined vacation escape. With 750 feet of pristine Gulf frontage, this home immerses you in the beauty and serenity of coastal living. Beautiful engineered white oak wood floors flow throughout the open, sun-filled living space, which seamlessly extends to your private balcony’s, the perfect spot to enjoy the tranquil sound of the waves and stunning sunsets. The updated kitchen features stone countertops, white cabinetry, and has been opened up to create a larger, more connected floor plan ideal for entertaining. The primary suite is a private sanctuary, boasting a remodeled marble bath with high-end fixtures and a spa-like ambiance. The guest suite provides equal comfort and privacy, featuring a beautifully appointed travertine-floored bathroom. A custom wall of California closets offers exceptional storage and style. The Club Longboat Beach and Tennis community offers amazing amenities, including private beach access with lounge chairs and beach umbrellas, eight professional har-tru tennis courts, pickleball, fitness center, shuffleboard, barbeque area, clubhouse with regular social events, sauna, spa and two heated swimming pools. Club Longboat is a pet-friendly community allowing up to two pets with fees that include exterior maintenance and insurance, cable, water, sewer and trash. Perfect as a full-time residence or an income-producing rental, with one-month minimum leases permitted up to 12 times per year. Only a short drive to many fine restaurants, boutiques, Anna Maria Island, St. Armands Circle and the City of Sarasota. Sarasota is a well-known center for arts and culture including the Asolo Theater, Van Wezel Performing Arts Center and Ringling Museum. Schedule your showing today and make resort style living a reality.
Listing Agent: Ryan Heers (941-726-1703)
2039 GULF OF MEXICO DR #G3-203, LONGBOAT KEY, FL 34228
$499,99917 Days on yellowkey MLS ID: A4688685
REDUCED by $39,001 (7.2%) on 04/15/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1214 Built: 1974Monthly Fee: $1,170 Tax: $5,576 (2025)Community: Seaplace ISpa: YesCondo
Taxes:$5,576
Remarks: Experience the Best of Coastal Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2.5-bath residence offering a perfect blend of comfort, style, and relaxed island living. This spacious two-level layout features an inviting open-concept living and dining area with neutral coastal tones, tile flooring throughout the main level, and seamless access to a private lanai—ideal for enjoying tranquil views and Gulf breezes. The updated kitchen is designed for both functionality and style, showcasing granite countertops, white cabinetry, stainless steel appliances, and a convenient breakfast bar, perfect for casual dining or entertaining. Upstairs, you’ll find two generously sized bedrooms, each offering privacy and comfort. The primary suite serves as a relaxing retreat, while the guest bedroom is ideal for family or visitors. The additional half bath on the main level adds convenience for guests. This residence is offered in move-in ready condition and reflects pride of ownership throughout. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an exceptional array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center, and a clubhouse with kitchen, library, and sauna. Additional features include playground areas, grilling stations, on-site management, and a 24-hour staffed gatehouse for security. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this home offers the ultimate Longboat Key lifestyle in one of the island’s most sought-after communities. Schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2425 GULF OF MEXICO DR #14B, LONGBOAT KEY, FL 34228
$1,690,000322 Days on yellowkey MLS ID: A4654664
REDUCED by $60,000 (3.4%) on 04/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $18,495 (2024)Community: Sea Gate ClubSpa: YesCondo
Taxes:$18,495
Remarks: BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work. Recent upgrades include Hurricane Impact Windows (2021), new flooring in both bedrooms (2021), updated bathrooms, fresh paint (2021), and an A/C system replaced in 2015. The convenience of an in-unit washer and dryer, a dedicated parking space, and ample guest parking add to the comfort of this coastal retreat. The beach and heated pool are just steps from your building, creating a true resort-style experience. Enjoy premium amenities such as a tennis court, air-conditioned bike room, kayak/paddleboard storage, clubhouse with kitchen, library/meeting space, and a fully equipped fitness center. Located within walking distance to Publix, CVS, places of worship, banks, the public library, and Town Hall. Just minutes to St. Armands Circle, where you'll find world-class dining and shopping. Immerse yourself in Sarasota’s rich cultural scene with easy access to the Sarasota Opera, Ballet, Ringling Museum, Selby Gardens, and numerous art galleries and theaters. This is your chance to live the Gulf Coast lifestyle—don’t miss it!
Listing is courtesy of: ANMARK REALTY LLC (941-363-1043)
Listing Agent: Andrey Markov (941-363-1043)
4485 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228
$760,000123 Days on yellowkey MLS ID: A4675789
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1022 Built: 1973Monthly Fee: $1,050 Tax: $4,183 (2024)Community: Arbomar AptsCondo
Taxes:$4,183
Remarks: Experience exceptional beachfront living in this beautiful Gulf-front residence at Arbomar on Longboat Key. Unit 402 is a 2-bedroom, 2-bath condominium offering direct, unobstructed Gulf of Mexico views and immediate beach access, making it the most affordable 2-bedroom, 2-bath opportunity on Longboat Key with true Gulf frontage. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways, updated carports, and new doors and impact-rated windows throughout the community. Inside, the home is move-in ready with a newer AC system and newer appliances, ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. Arbomar offers elevator access, a heated beachfront pool, fitness center, and a welcoming, well-maintained community. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions, and world-class golf—while delivering the rare luxury of direct Gulf views and private beach access at an exceptional value.
Listing Agent: Richard Tyson (941-999-1179)
4350 CHATHAM DR #Unit E-208, LONGBOAT KEY, FL 34228
$675,000143 Days on yellowkey MLS ID: A4672221
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 1969 Tax: $6,535 (2025)Community: Longboat HarbourCondo
Taxes:$6,535
Remarks: One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! REDUCED $20,000! NEWLY REMODELED • COASTAL LUXURY RESIDENCE Longboat Harbour • Building E #208 | Corner End Unit • Bay & Harbour Views. CLOSEST BUILDING TO A SHORT WALK ACCROSS THE STREET WITH A PRIVATE DEEDED GULF BEACH ACCESS WITH PAVILION, RESTROOMS AND SHOWERS TOTALLY REMODELED FROM FLOOR TO CEILING second-floor corner residence in the highly sought-after Longboat Harbour Community. This light-filled home captures sweeping views of Sarasota Bay and Longboat Harbour. This spacious two-bedroom, two-bath retreat has been transformed with exceptional attention to detail. Elevated finishes, a soothing coastal palette, and an airy open layout blend modern luxury with effortless livability. Corner units of this caliber are rarely available. From the two bedrooms, you step out to the exceptionally Large Lanai with floor to ceiling sliding glass doors. A SHOWCASE KITCHEN WITH TWO SUNLIT WINDOWS AND WATER VIEWS Elegant, functional, and beautifully appointed: • Frigidaire Professional stainless steel appliances • Gleaming quartz countertops • 9-inch deep sink • Pull-out cabinet shelving • Pantry closet • Designer tile backsplash • Large Eat-In Kitchen with water views & sunsets • Instant hot-water. LUXURIOUS PRIMARY SUITE An elevated retreat professionally designed for comfort and relaxation • Private ensuite bath • Custom California Closet walk-in wardrobe • Built-in desk feature • Remote-controlled luxury solar shades. RESORT-INSPIRED AMENITIES Longboat Harbour offers a lifestyle unmatched on the Gulf Coast: • Designated covered parking spot conveniently located • Personal storage space on the third floor • Private deeded Gulf beach access with pavilion, restrooms & shower • Four sparkling pools • Fitness center & sauna • Tennis & pickleball courts • Billiards room, library & meeting rooms • Picnic areas with grills • Putting green • Fishing pier • Affordable resident-only boat dockage • KAYAK LAUNCH and KAYAK WHICH SELLER WILL BE GIFTING TO THE BUYER. Enjoy effortless waterfront living and endless ways to explore the natural beauty of Longboat Key. PROPERTY ENHANCEMENTS & UPDATES: Thoughtfully improved for comfort, reliability, and peace of mind: • NO HURRICANE DAMAGE OR FLOODING • Bosch Washer & Dryer • Newer AC: 12/5/221 • Newer Hot Water Heater: 3/3/17 • New roofs throughout the community • Electrical and plumbing systems updated. A BEAUTIFULLY RENOVATED INTERIOR THAT CREATES THE ULTIMATE COASTAL LIFESTYLE/ THE MONTHLY HOA FEE INCLUDES HAZARD, HURRICANE AND FLOOD INSURANCE/ RESERVES HAVE BEEN FULLY FUNDED
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Billie Chipain (941-587-8556)
4420 EXETER DR #303, LONGBOAT KEY, FL 34228
$625,00084 Days on yellowkey MLS ID: TB8455704
REDUCED by $24,900 (3.8%) on 04/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970Monthly Fee: $1,412 Tax: $3,678 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$3,678
Remarks: Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (727-342-3800)
Listing Agent: Jerry Gemmecke (317-445-2434)
415 L AMBIANCE DR #B202, LONGBOAT KEY, FL 34228
$2,150,000165 Days on yellowkey MLS ID: A4670048
0 Days Off yellowkey (back on 4/17/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2385 Built: 1992 Tax: $23,948 (2025)Community: L Ambiance 1Spa: YesCondo
Taxes:$23,948
Remarks: Gulf-front enclave offers a rare blend of luxury, location, and lifestyle that transforms every day into a retreat. From the moment you step inside, you’re greeted by an atmosphere of refined elegance and architectural clarity—crafted for those who appreciate design as a way of life. This residence exudes sophistication with interiors envisioned by an internationally acclaimed designer, delivering clean lines, thoughtful textures, and a timeless palette that compliments the natural beauty outside your doors. Here the edges between indoor living meet the outdoors. An open light-filled living area opens to a wraparound terrace, Gulf views, and tranquil gardens, where the turquoise Gulf and the green of the fairways meet the Florida sunshine. The culinary chef’s kitchen features premium appliances, contemporary cabinetry, and a layout that invites effortless entertaining—whether you’re hosting a sunset cocktail hour or a quiet dinner with close friends. This is a three-bedroom, three-bath home designed for comfort and privacy. Each bedroom is an en-suite retreat, offering serene views. Positioned along the Gulf shoreline, you’ll enjoy the sunrises, moonrises, golf course vistas, and the aroma of fresh-cut greens as a constant backdrop. Yet you’re just moments from the heart of the action: steps to the beach, golf course (Longboat Key Club). Minutes to St. Armands Circle, with access to dining, shopping, and cultural scenes that define Longboat Key living. Key Features at a Glance: - Location: South end of Longboat Key, beachfront setting with golf course and garden views - Residence: 3 bedrooms, 3 en-suite baths - View: Beach, and golf course views; tranquil garden vistas - Proximity: Steps to the beach and Longboat Key Club; Very close to the West Coast’s second-largest marina - Lifestyle: Luxury coastal living with resort-style amenities and ample entertaining spaces. Residents enjoy a 24-hour manned gated community, concierge service, security, an on-site manager, a resort-style heated Olympic-size pool and spa, a state-of-the-art fitness center, outdoor BBQ areas, three social rooms, and three overflow guest suites available on a first-come basis. This pet-friendly community is dedicated to making every detail perfect, delivering a lifestyle that is as effortless as it is extraordinary. Furniture is available to purchase separately from the real estate. WHERE LONGBOAT KEY COASTAL LIVING MEETS THE GULF!
Listing Agent: Judy Kepecz-Hays (941-587-1700)
1915 HARBOUR LINKS CIR #6, LONGBOAT KEY, FL 34228
$1,950,00018 Days on yellowkey MLS ID: A4688148
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2476 Built: 2002 Tax: $19,319 (2025)Community: Bay IslesSpa: YesCondo
Taxes:$19,319
High School: Sarasota High
Remarks: Private Beach access + Gated Bay Isles living-Maintenance free Villa on Longboat Key! Welcome to Emerald Pointe South! This well-maintained residence offers a light and open floor plan with spacious living and dining areas, ideal for everyday living and entertaining. Sliding glass doors provide abundant natural light and lead to a private screened lanai overlooking lush tropical landscaping. The kitchen features ample cabinetry, solid surface countertops, a breakfast nook, and recent updates including a new microwave, dishwasher, and stove. The primary suite offers dual walk-in closets and an en-suite bath with dual vanities, soaking tub, and separate shower. Two additional bedrooms, each with en-suite baths, are located on the second floor, providing privacy for guests or family. Ideally located just minutes from St. Armands Circle and downtown Sarasota, this home offers convenient access to dining, shopping, and beaches. Wake up to the coveted lifestyle of Longboat Key, whether as your full-time residence or a seasonal escape. This property captures the essence of coastal living with comfort, tranquility, and effortless access to everything that makes Longboat Key so desirable.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Cathy Palmer (678-524-1104)
225 SANDS POINT RD #7101, LONGBOAT KEY, FL 34228
$699,00091 Days on yellowkey MLS ID: A4678918
3 Days Off yellowkey (back on 3/30/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1983 Tax: $7,270 (2025)Community: Inn On The Beach Ph IiiCondo
Taxes:$7,270
Remarks: Under contract-accepting backup offers. Enjoy peaceful lagoon views from this completely remodeled Junior Suite. Sold turnkey furnished and currently in the hotel program, the Junior Suites in this building have 10’ ceilings unlike the other buildings. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace. As an owner in the hotel program you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship Golf, the award-winning Tennis Gardens, spa, fitness center, white sand beach with umbrellas & waitstaff, and a full service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying your Longboat Life today!
Listing Agent: Ian Addy, Pa (941-961-8850)
3240 GULF OF MEXICO DR #B104, LONGBOAT KEY, FL 34228
$495,00010 Days on yellowkey MLS ID: A4688243
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1975 Tax: $4,538 (2025)Community: PortobelloCondo
Taxes:$4,538
Remarks: Experience tranquil island living in this beautifully maintained first-floor residence at Portobello, offering private, serene views of expansive grounds, lush mangroves, and the bay. With your beach, shimmering Gulf waters, and breathtaking sunsets just across the street, this is the perfect coastal retreat. Designed with a desirable split floor plan, the home is filled with natural light from sliding glass doors that span the width of the residence. The large screened-in lanai is accessible from the living area and both bedrooms—seamlessly blending indoor and outdoor living while overlooking a generous grassy yard space and peaceful bayou, perfect for canoeing and kayaking right from your backyard. The kitchen features granite countertops and stainless steel appliances. Offered turn-key and fully furnished, this residence is move-in ready and ideal for seasonal or full-time living. Portobello is a sought-after Beach-to-Bay community ideally located mid-Key, offering an exceptional array of amenities including 600 feet of private beach frontage and 260 feet along the bay. Residents enjoy a heated community pool, tennis courts, clubhouse, BBQ and picnic areas, fishing pier, and kayak launch. Just minutes from the world-class shopping and dining of St. Armands Circle and everything Sarasota has to offer, this exceptional residence invites you to experience the pinnacle of Longboat Key living—where every day feels like a vacation.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Laura Rode (941-724-9957)
6700 GULF OF MEXICO DR #117, LONGBOAT KEY, FL 34228
$550,0006 Days on yellowkey MLS ID: A4687787
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1969 Tax: $2,348 (2025)Community: Whitney BeachSpa: NoCondo
Taxes:$2,348
Remarks: Welcome to 6700 Gulf of Mexico Drive #117, a beautifully reimagined end-unit 2-bedroom, 2 full bath residence in the sought-after Whitney Beach community on Longboat Key. Taken down to the studs and completely renovated, this waterfront condominium offers coastal living with sweeping views of Bishop’s Bayou, abundant natural light, and exceptional privacy. A private front courtyard welcomes you inside, where new high-end luxury vinyl plank flooring flows throughout, and a bright, open layout immediately draws your eye to the water. As an end unit, additional windows enhance the airy feel, while hurricane-impact windows and sliding doors frame tranquil bayou views. From the main living space—and even from the primary bedroom upon waking—you’ll enjoy peaceful scenes of dolphins, manatees, and glowing sunsets reflecting across the water. The fully redesigned kitchen is both stylish and functional, featuring granite countertops, soft-close cabinetry, custom glass-front accents, classic subway tile backsplash, designer pendant lighting, peninsula seating for four, and a full suite of GE stainless steel appliances—all positioned to capture the water views. Both bathrooms have been completely renovated with glass walk-in showers, elegant tilework, and quartz-topped vanities, offering a clean, modern aesthetic. A new Whirlpool stackable washer and dryer adds everyday convenience. Whitney Beach is a unique beach-to-bay community with deeded private access to the Gulf just across the street. Residents enjoy resort-style amenities including pools, tennis courts, shuffleboard, barbecue areas, kayak storage and launch, walking paths, and a tranquil bayfront pavilion. Boat slips are available when offered, and the community pier provides a charming setting for fishing or relaxing by the water. Ideally located on the north end of Longboat Key, this residence offers easy access to Anna Maria Island, as well as the dining, shopping, and cultural attractions of Sarasota. Whether as a full-time home, seasonal retreat, or investment, this is an exceptional opportunity to enjoy the best of bay-to-beach living. Professional photos coming soon.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kelly Sallee (941-914-0400)
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