Location: Longboat Key
Do Not Show Listings
7105 GULF OF MEXICO DR #21, LONGBOAT KEY, FL 34228
$895,000220 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,071
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
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)
842 BAYPORT WAY #842, LONGBOAT KEY, FL 34228
$675,00023 Days on yellowkey MLS ID: A4687058
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983 Tax: $5,662 (2025)Community: Bayport Bch & Ten Ph FSpa: NoCondo
Taxes:$5,662
Elementary School: Southside Elementary
High School: None
Tax Year: 2025
Middle School: Booker Middle
Remarks: Poised within the Gulf to Bay community of Bayport Beach and Tennis Club, 842 Bayport Way offers 1570 square feet of effortless indoor-outdoor living. This first floor corner residence brings added natural light and extra privacy, giving the feeling of a private home with the ease of low maintenance living. The open layout includes a spacious kitchen, a primary bedroom with office space, walk-in closet and ensuite bath with dual vanities, as well as convenient in-unit laundry, covered parking and private storage closet. A combined dining and living area opens to a screened lanai and extended brick patio. This is a favorite spot for morning coffee, afternoon siestas and al fresco dining watching sunset skies. A garden gate leads to a direct side path to deeded beach access across the road. For pet owners, Bayport is small-pet friendly, and this walk-out location makes dog-walking especially easy. Spanning 27 acres of exquisitely landscaped tropical grounds, Bayport is celebrated for its timeless Tim Seibert architecture, exceptional amenities, and easy resort lifestyle. Residents enjoy a heated Jr. Olympic pool, clubhouse, fitness center, tennis, bocce ball, and shelled walking paths. Along the bay shoreline, a fishing pier, kayak launch and storage is perfect for morning paddles or simply enjoying nature . On the Gulf side, 1,200 feet of deeded beach access, complete with loungers and umbrellas, makes enjoying Longboat Key’s famously uncrowded beaches effortless. The condo’s split floor plan works well for year round living or a seaside escape. A favorable rental policy offers excellent income opportunity. Located mid-key, Bayport keeps you close to shopping, daily conveniences, great island dining, and the vibrance of Sarasota, all while feeling tucked away and serene. Settle in and enjoy a slice of true paradise on Longboat Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Rosemarie Mckee (941-504-9396)
2016 HARBOURSIDE DR #317, LONGBOAT KEY, FL 34228
$895,00056 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
Elementary School: None
Middle School: None
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
$649,90091 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.
Listing Agent: Debby Mccaig (941-544-1713)
549 SUTTON PL #t 19, LONGBOAT KEY, FL 34228
$329,00098 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
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
$649,00055 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)
2301 GULF OF MEXICO DR #101N, LONGBOAT KEY, FL 34228
$1,395,000160 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
$1,495,00079 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.
3806 GULF OF MEXICO DR #C312, LONGBOAT KEY, FL 34228
$320,0004 Days 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 Agent: Greg Hudson (941-302-1485)
5655 GULF OF MEXICO DR #D107, LONGBOAT KEY, FL 34228
$799,00048 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)
828 BAYPORT WAY #828, LONGBOAT KEY, FL 34228
$900,00013 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
High School: Booker High
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)
706 BAYPORT WAY #706, LONGBOAT KEY, FL 34228
$739,00015 Days on yellowkey MLS ID: A4688503
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1601 Built: 1980Monthly Fee: $1,978 Tax: $6,727 (2025)Community: Bayport Bch & Ten Ph CCondo
Taxes:$6,727
Remarks: This stylish turnkey furnished beach retreat at Bayport Beach & Tennis Club is the perfect blend of classy with a modern flair. Before entering the home take note of the huge 16’ x 13’ outdoor deck where you can enjoy a partial view of the Gulf. It's a great place to start your day with a cup of morning coffee, or enjoy a nice meal in the evening, and catch the spectacular colors of the sky as the sun sets! Step inside to this inviting, beautifully appointed 2-bedroom 2-bath condominium with luxury vinyl flooring and crown molding throughout. The entire living/ dining areas, lanai, both bedrooms and second bathroom have all been recently updated. Giving the condo a fresh polished appearance accentuated by recessed glass display shelving and an abundance of recessed lights. The depth of workmanship in the updates carries onto the stylized door moldings into the primary bedroom. All popcorn has been removed! The kitchen offers a coffee bar, stainless steel appliances, a pantry, a nice arrangement of cabinets, and granite countertops open to the dining room and living room, perfect for entertaining. Take in the view of the lush tropical landscape and gorgeous pond right below the lanai that is open to the living room. Perfect for a Murphy bed, extra living space, a reading nook or your second favorite spot for your morning coffee as the sun rises. The primary bedroom offers an additional 6’ by 6’ area that is perfect for an office desk looking out over nature. The primary also offers a walk-in closet and a generously sized ensuite bath with dual vanities. Bayport Beach & Tennis Club is a gem with 27 tropical landscaped acres and 1200 feet of private Gulf waterfront deeded access. Where you can grab a chair and umbrella and soak up the sun, or take in the breathtaking sunsets. Enjoy Sarasota Bay just outside your door and stroll to the private dock where you can fish, kayak, paddleboard, and watch for the manatees and dolphins as they cruise by. This community also offers a clubhouse, fitness center, 4 Har-Ter tennis courts, golf practice net, and a Junior-Olympic heated pool. Bayport Beach & Tennis Club consists of 17 buildings built between 1979 and 1983. Designed by architect Tim Seibert of the Sarasota School of Architecture. Located mid-key with a wealth of attractions moments away, including Bayfront Park, steps away, offering Pickle Ball, Basketball, Shuffleboard courts, playground, bike paths, kayak launch and Publix 2 miles away.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Kelly Erb (941-720-9586)
5655 GULF OF MEXICO DR #A107, LONGBOAT KEY, FL 34228
$799,00013 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
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)
6750 GULF OF MEXICO DR #163, LONGBOAT KEY, FL 34228
$500,00052 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
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)
2039 GULF OF MEXICO DR #G3-203, LONGBOAT KEY, FL 34228
$499,99920 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
$1,690,000325 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
$760,000126 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 is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Richard Tyson (941-999-1179)
4420 EXETER DR #303, LONGBOAT KEY, FL 34228
$625,00087 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
$2,150,000168 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
$1,950,00021 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)
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