Location: Longboat Key
Do Not Show Listings
4127 GULF OF MEXICO DR #N102, LONGBOAT KEY, FL 34228
$4,700,000147 Days on yellowkey MLS ID: A4680618
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3521 Built: 2007 Tax: $30,723 (2025)Community: La FirenzaSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$30,723
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Spectacular Gulf of Mexico views define this exceptional three-bedroom, three-and-a-half-bath residence that lives like a single-family home. A large wraparound terrace with a built-in grill offers seamless indoor-outdoor living, and private steps leading directly to the sandy beach – perfect for sunset entertaining or morning walks along the shore. Enter the home through a private elevator into a formal foyer with double door entry into the residence. The gracious living room is framed by expansive windows showcasing endless water views and exceptional sunsets flowing effortlessly to a built-in wet bar complete with wine refrigerator, ice maker, and a dedicated desk area—ideal for entertaining or casual work-from-home moments. A formal dining room with elegant ceiling detail makes hosting a dinner party a treat. Plantation shutters throughout the residence add a coastal and private touch. The gourmet kitchen is designed for both function and style, offering a large island for gathering, side-by-side Sub-Zero refrigerator and freezer, Wolf gas cooktop, Wolf oven with warming drawer, generous pantry, and a cozy desk area for browsing favorite recipes. A large center island and charming breakfast nook are the perfect spots for morning coffee or casual meals. Adjacent to the kitchen, the inviting keeping room opens to a private east-facing terrace with beautiful sunrise and views of Sarasota Bay. The expansive owner’s suite is a true retreat, featuring its own breakfast bar with sink and refrigerator for enjoying morning coffee while overlooking the Gulf. Two oversized, custom-built walk-in closets provide exceptional storage. The spa-inspired bath includes double vanities, a glass-enclosed shower, a private water closet with bidet, and refined finishes throughout. Two en-suite guest bedrooms with large custom-built closets open onto a private terrace with views of Sarasota Bay, ensuring comfort and privacy for family and guests alike. This rare beachfront residence combines luxury, privacy, and the ease of coastal living, all with breathtaking views and thoughtfully designed spaces for everyday enjoyment and elegant entertainment. Residents of La Firenza enjoy a boutique, gated setting with private beach access, a heated beachfront pool and spa, fitness facilities and secure garage parking.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
1065 GULF OF MEXICO DR #302, LONGBOAT KEY, FL 34228
$749,000644 Days on yellowkey MLS ID: A4624142
INCREASED by $130,000 (21.0%) on 06/01/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1392 Built: 1981 Tax: $4,571 (2023)Community: Beachplace IiiCondo
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)
2301 GULF OF MEXICO DR #12N and 11N, LONGBOAT KEY, FL 34228
$2,377,000188 Days on yellowkey MLS ID: A4675054
REDUCED by $111,000 (4.5%) on 04/21/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2415 Built: 1970 Tax: $13,538 (2025)Community: Islander Club Of LongboatSpa: NoCondo
Taxes:$13,538
Remarks: Rare Beachfront Opportunity - Two Adjacent Residences at The Islander Club, South Longboat Key Seize a truly rare and unique opportunity to own two adjacent Gulf-front residences in the North Tower of The Islander Club on South Longboat Key. Featuring highly sought-after southwest and northwest exposures, these first-floor walk-out condos live like a maintenance-free beachfront home, with no stairs or elevators and direct access from two private terraces to the Olympic-size beachfront pool and the private white sandy shores of the Gulf of Mexico’s crystal clear aqua waters. Combined, the residences offer 2,500+ square feet of Gulf-front living space, including four beachfront bedrooms and four full bathrooms, two balconies with over 500 square feet of total outdoor frontage, and expansive walls of glass showcasing panoramic Gulf views, brilliant sunshine, gorgeous sunsets, and refreshing cross-breezes. The layout functions as an expansive and seamless beachfront residence with flexible configuration options—combine both units into one refined Gulf-front luxury home, or live in one and rent the other, or tailor and customize the space for personal use or investment potential. Located directly on the beach in South Longboat Key, this one-of-a-kind legacy property is just three miles from St. Armands Circle and minutes from downtown Sarasota’s dining, shopping, and cultural attractions. Two covered parking spaces are included, along with additional guest parking available. The Islander Club features 400 feet of private beachfront, a new fitness and community center, beachfront pool, two Har-Tru tennis courts (soon to be remodeled for pickleball use as well), library, conference room, on-site management, gated access, and a highly advantageous and rare owner-to-owner rental program. Convenient to Publix, CVS, acclaimed restaurants, boutique shopping, and Sarasota’s renowned arts scene. Enjoy breathtaking Gulf sunsets and an unmatched Longboat Key beachfront lifestyle at one of Longboat Key’s most sought-after beachfront addresses.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Leah George (941-780-0597)
1105 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228
$995,000315 Days on yellowkey MLS ID: A4661696
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981 Tax: $9,142 (2024)Community: Beachplace IiCondo
Taxes:$9,142
High School: Booker High
Tax Year: 2024
Middle School: Pine View School
Remarks: Beachplace at Longboat Key: Major price reduction for this Gulf-front luxury and rental-friendly, turnkey furnished investment opportunity! An iconic condominium in the mid-century modern style, Beachplace was constructed under the direction of Tim Siebert, one of the leaders of the Sarasota School of Architecture, and spans 31 acres with a quarter mile of Gulf beachfront. This price reduction makes this an ideal residence or investment opportunity. With a direct Gulf view, and a gentle walk to the beach, this two-bedroom, two-bathroom residence offers serene living; a spacious primary suite with ensuite bath, plus a guest suite, private balcony with stunning sunset views, full kitchen and dining and living spaces, new impact glass windows, all complemented by nearby amenities, including private beach access, a Junior Olympic-sized pool, spa, and a kid's pool. A clubhouse, two fitness facilities, a sauna, tennis, and pickleball courts, and two grilling stations complete the resort lifestyle. Electric Vehicle charging is on-site. The Resort at Longboat Key Club is immediately adjacent and offers championship golf and tennis facilities, a full-service marina nearby, and fine dining for its members and guests. St. Armands Circle shopping, dining, and entertainment is a short drive south, and Sarasota, with its thriving arts and cultural communities, eclectic shopping and dining, and extraordinary architecture, is a brief ride across the bay. Thirty-day minimum rentals are permitted twelve times annually. The buyer or their agent should review the possibility of any special assessments with the condominium manager. All of the information provided is considered reliable, but should also be verified by the buyer or buyer's agent.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Tom Aposporos (941-704-4250)
4310 FALMOUTH DR #102, LONGBOAT KEY, FL 34228
$649,900154 Days on yellowkey MLS ID: A4679011
REDUCED by $10,100 (1.5%) on 04/30/2026
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
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Recently reduced—don’t miss this opportunity. No special assessments after the 2024 storms, no history of flooding, well-funded reserves, and structural soundness supported by SIRS report! 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)
435 L AMBIANCE DR #L707, LONGBOAT KEY, FL 34228
$2,890,000294 Days on yellowkey MLS ID: A4663998
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2525 Built: 1994 Tax: $32,005 (2025)Community: L Ambiance At Longboat Key Club Ph 02Condo
Taxes:$32,005
Remarks: There are views… and then there is this view! From this desirable seventh-floor corner residence at L’Ambiance, the horizon unfolds in a breathtaking panorama—Gulf of Mexico sunsets ablaze to the west, Sarasota Bay shimmering to the east, the downtown skyline sparkling in the distance, and the manicured fairways of the Longboat Key Club Island side golf course below. Morning light and evening color become part of daily life, ever-changing and endlessly captivating. The arrival to this luxurious community, sets an immediate tone of distinction. A fountain-lined drive and 24-hour manned gate lead to a secured building where a full-time concierge delivers an unrivaled level of service. From welcoming guests to coordinating deliveries and attending to daily conveniences, the care and professionalism here is unrivaled. An elevator opens directly to your private foyer with double doors, revealing architectural details that add warmth and refinement—pecky cypress ceiling accents, a gracious dry bar, custom built-ins, soft cove lighting, and walls of glass that frame the surrounding water views. Expansive wraparound terraces extend the living spaces outward, creating an extraordinary setting for sunset dining, morning coffee, or effortless entertaining against a backdrop of sea and sky. The kitchen is thoughtfully appointed. The center prep island includes its own auxiliary refrigerator and freezer drawers—ideal for entertaining—while the breakfast nook overlooks the water and opens directly to the terrace. The spacious open living and dining areas are bathed in natural light, designed to showcase both the views and today’s modern lifestyle. This well-designed two-bedroom, two-and-a-half-bath residence lives beautifully—and is complemented by a significant advantage: reservable guest suites located just downstairs. Your visitors enjoy private, comfortable accommodations within the building, allowing you to preserve the serenity and elegance of your own home while hosting with ease. The split-bedroom floor plan enhances privacy, with the primary suite positioned to capture sweeping Gulf views. Recently enhanced with an oversized custom-fitted closet, it offers both luxury and thoughtful functionality. A full-sized laundry room, a rear service entrance, motorized blinds and draperies throughout, private parking, a storage unit, and a wine locker complete this exceptional offering. Residents of L’Ambiance enjoy resort-caliber amenities including a beachfront pool with cascading waterfalls, two Har-Tru tennis courts, a state-of-the-art fitness center, elegant social rooms, guest parking, and direct beach access. Just a couple of minutes away, world-famous St. Armand's Circle and over the Ringling bridge to everything downtown Sarasota has to offer.... fine dining, boutique shopping, and cultural attractions. Optional membership at the exclusive Longboat Key Club provides access to championship golf, premier tennis, several restaurants, boating facilities, and an active social calendar. This is more than a condominium—it is a private coastal sanctuary supported by impeccable service, refined amenities, and one of the most commanding vantage points on Longboat Key.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Pam Charron (941-993-3388)
4960 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228
$649,900155 Days on yellowkey MLS ID: A4679160
0 Days Off yellowkey (back on 5/30/2026)
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: Under contract-accepting backup offers. Public showings are now available for the first time. After months of restricted access due to a tenant, this residence is finally available for public showings. Restricted access resulted in only a handful of private showings, giving today’s buyers a rare chance to discover a home that’s been under the radar. 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)
4390 EXETER DR #206, LONGBOAT KEY, FL 34228
$529,000239 Days on yellowkey MLS ID: A4670032
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $7,775 (2024)Community: Longboat HarbourCondo
Taxes:$7,775
Remarks: Under contract-accepting backup offers. ~~~~~ * * * * SELLER SAYS SELL * * * * ~~~~~~~ * * * * NICEST FULL REMODEL IN LONGBOAT HARBOUR * * * * ~~~~~ PRICED BELOW MARKET VALUE ~~~~~ Enjoy island living nestled in the VIBRANT community of Longboat Harbour on beautiful Longboat Key. This UPDATED and FULLY RENOVATED condo offers a luxurious living experience with abundant amenities and stunning canal views where the Manatee play and sun bathe! Recent tastefully completed renovations include ALL NEW TILE FLOORING, NEW A/C UNIT, a fully updated gourmet kitchen with quartz counters, new cabinets, new appliances, a WASHER/DRYER IN UNIT, fully remodeled bathrooms, new doors and fresh paint throughout, a new primary WALK-IN closet, and PLANTATION SHUTTERS, that provide an interior that is both stylish and inviting. The owners opened the lanai to add more interior space to the living area with a seamless transition. No need to replace the sliders as they did that for you (NEW HURRICANE IMPACT SLIDERS) Need additional storage space? This condo also features a separate storage locker and bike/Kayak storage as well. Located in a prime location within a gated community on Longboat Key, this property is a water-lover's paradise. Boating enthusiasts will appreciate the deep-water canal access to Sarasota Bay, with boat slips available on a first come basis and additional kayak launches. Longboat Harbour is renowned for its welcoming atmosphere and an array of amenities designed to cater to every interest and lifestyle. This resort like community with an on-site manager offers a range of recreational activities including mini-golf, shuffleboard, tennis, and pickleball. Fitness enthusiasts will appreciate the large and well-equipped fitness center, complete with private locker rooms and saunas. Additionally, the beautifully renovated recreation room overlooking the bay, serves as the heart of social gatherings in Longboat Harbour, hosting a variety of clubs and activities complemented by a kitchen and dance floor. The four heated swimming pools provide relaxation and enjoyment year-round. For beach lovers, a community beach pavilion across Gulf of Mexico Drive offers residents private, PRIVATE DEEDED BEACH ACCESS with a cabana, parking, restrooms, and dressing areas. Witness breathtaking sunrises, spot manatees, and savor stunning sunsets from this serene beachfront location. This exceptional opportunity offers an unparalleled lifestyle in one of Longboat Key's most active, social, and vibrant communities! Seize the opportunity to experience waterfront living at its finest. Schedule your private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Sheryl Vanduren (720-384-4884)
4440 EXETER DR #106, LONGBOAT KEY, FL 34228
$649,000119 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)
4325 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228
$1,100,00042 Days on yellowkey MLS ID: A4693621
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1336 Built: 1975 Tax: $4,084 (2025)Community: Tiffany PlazaSpa: NoCondo
Taxes:$4,084
Remarks: Experience coastal living in this two-bedroom, two-bath direct Gulf-front residence ideally on the main floor of a desirable mid-rise community on Longboat Key. Freshly painted and thoughtfully enhanced with quartz countertops in both the kitchen and laundry room, along with recently updated washer and dryer appliances, the residence also features crown molding, updated trim and plantation shutters throughout, as well as Gulf-side hurricane shutters. The covered Gulf-side lanai provides the perfect setting to relax and enjoy the coastal surroundings year-round. The primary bedroom offers a very large walk-in closet. This residence includes a designated covered parking space along with private exterior storage. Residents enjoy an impressive array of amenities, including a clubhouse with a sauna, a heated Gulf-front pool, an interlocking stone patio and barbecue, a covered area and direct beach access. Ideally in a sought-after mid-key location, the property is close to St. Armands Circle, with its renowned boutiques, dining and shopping, while downtown Sarasota is just over the bridge, offering arts, culture, dining and entertainment. Heading north, enjoy convenient access to Anna Maria Island, while heading south, you will find the many amenities of Longboat Key, including Publix, CVS, places of worship, banks, parks, town hall, Bayfront Park, public tennis courts, boat launches and more.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Dennis Girard (941-809-0041)
6701 GULF OF MEXICO DR #332, LONGBOAT KEY, FL 34228
$700,00079 Days on yellowkey MLS ID: A4689175
REDUCED by $95,000 (11.9%) on 05/29/2026
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 990 Built: 1971 Tax: $3,403 (2025)Community: Whitney Beach IiiCondo
Taxes:$3,403
Remarks: Finally, you have the opportunity to own your own "Walk-Out", Gulf Front, Beach Condo. Tucked just behind a beach grass sand dune and situated on a grassy knoll, this unit is perfectly positioned to benefit from refreshing sea breezes while offering spectacular sunset views. This rare one-bedroom condo has been completely remodeled and now features a unique two-bathroom floorplan. Remodeled Interior and Modern Upgrades: The spacious living area boasts premium appliances and upgraded stone countertops on new cabinetry within a newly designed open kitchen. Updates abound throughout the unit: new hurricane impact resistant sliding doors and a front window, along with modern bathrooms. The property is being sold turn-key—everything stays, making it a seamless move-in experience. Step inside and discover a bright, inviting interior with an open, light-filled layout designed to maximize both space and natural beauty. Large glass sliders connect the interior to the outdoors, bathing the kitchen and living area in sunlight and blending innovative functionality with coastal charm. The thoughtfully designed bedroom and bathrooms provide serene retreats, perfectly balancing comfort and style. Private Outdoor Oasis: The unique ground floor “Whitney Beach Gulfside” floorplan offers both a front privacy-fenced enclosed patio—ideal for alfresco dining or beachfront gardening—and a rear open patio for relaxation. Whether enjoying a quiet morning coffee or an evening cocktail, the gentle sea breeze creates the perfect setting for unwinding. Resort-Style Community Amenities: Enhance your lifestyle with a range of well-maintained community amenities, including a sparkling pool, tennis courts, shuffleboard, beach chairs, boat slips available for lease, and a tranquil pavilion by the bayou for water enthusiasts. Unmatched Location and Lifestyle: Experience the best of coastal living on Longboat Key. Whitney Beach is located on the quiet, northern end of Longboat Key, close to fantastic restaurants, shops, and shopping—just steps away, an easy bike ride, or a short drive to visit St Armands Circle. This condo combines a highly desirable location with the privacy and comfort of a casual beachfront lifestyle—perfect for year-round living, a seasonal retreat, or a smart investment. With one-month minimum rentals allowed up to 12 times per year, the property offers excellent investment potential. BONUS: the community features two-story buildings and is exempt from Florida’s Milestone inspection and reporting requirements, ensuring a NO SURPRISE experience. Discover Longboat Key: Enjoy the finest Longboat Key has to offer, where luxury meets laid-back coastal charm. Schedule your private tour today!
Listing Agent: Faye Doyle (941-504-7496)
3804 GULF OF MEXICO DR #B207, LONGBOAT KEY, FL 34228
$389,00092 Days on yellowkey MLS ID: TB8490120
1 Days Off yellowkey (back on 5/29/2026)
REDUCED by $8,000 (2.0%) on 05/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1133 Built: 1970 Tax: $3,764 (2025)Community: Beach Harbor ClubCondo
Taxes:$3,764
Remarks: Welcome to your new slice of paradise at the Beach Harbor Club! This gem is located in 'B' building, closest to the Gulf of Mexico, and less than one-minute walk to pristine white sand beach ! "This bright two-bedroom, two-bathroom condo has been thoughtfully updated. Standing out as a unique residence that is 12.5% larger than front-facing units, this south-facing home is drenched in tons of natural light and features a modern open-concept kitchen and living room design. The chef’s kitchen is a true centerpiece, boasting a 14-foot-long center granite counter and custom cabinetry with soft-close drawers and doors. Throughout the entire home, you will find cool-to-the-touch 18-inch travertine tiles on all floors and Bahama shutters on every window, while the primary suite offers a spacious walk-in closet and beautiful views of the Gulf—vistas that can also be enjoyed right from the foyer. Designed for convenience with two separate entrance doors, this condo makes it easy to walk to the beach via your deeded access on the pristine sands of Longboat Key or launch a kayak into the bay right from the community docks. Between the GULF VIEWS, fitness center, and sunset views over the water, it feels like a year-round vacation. You’re perfectly placed mid-key, so you can easily bike over to Bayfront Park for a game of pickleball or a walk along the bay trails. With a covered carport, everything is set for you to just arrive and start enjoying the coastal lifestyle—Longboat living truly doesn't get better than this! Schedule your tour today! Come and visit this Beauty, this will not last long!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Sarah Wampler (941-209-0676)
545 SANCTUARY DR #B506, LONGBOAT KEY, FL 34228
$1,828,000189 Days on yellowkey MLS ID: A4675800
0 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2375 Built: 1991 Tax: $19,482 (2025)Community: Sanctuary IiiCondo
Taxes:$19,482
High School: Riverview High
Remarks: Under contract-accepting backup offers. Bright, spacious and beautifully maintained, this 3BR/2.5BA fifth-floor residence at The Sanctuary offers refined coastal living in one of Longboat Key’s most sought-after gated communities, ideally positioned on the island’s desirable southern end. Upon entry, walls of floor-to-ceiling glass sliders immediately draw your eye to sweeping panoramic views of the Sarasota city skyline, shimmering Sarasota Bay and the emerald fairways of the Links golf course. By night, downtown’s twinkling lights create a dramatic and ever-changing backdrop. The popular Brittany floor plan features recessed lighting, crown molding, 18-inch tile flooring throughout the main living areas and a tiled open terrace perfectly suited for sunrise coffee or evening cocktails. The kitchen has been opened to enhance flow and functionality, offering solid-surface countertops, a center island, tile backsplash and an eat-in area framed by a wall of glass. Double doors lead to the oversized primary suite, filled with natural light and offering terrace access, a walk-in closet and a spa-inspired bath with soaking tub, walk-in shower and dual vanities. Wraparound terraces further enhance the indoor-outdoor lifestyle, making this residence ideal for both everyday living and entertaining. The Sanctuary delivers an unparalleled resort-style experience with 1,200 feet of pristine white-sand beachfront, private boardwalk beach access, a heated Gulf-side pool with 25-meter lap lane, outdoor whirlpool spa and beachfront gazebo. Additional amenities include two lighted Har-Tru tennis courts, a state-of-the-art fitness center, saunas, an entertainment room, on-site management, 24-hour guard-gated security and coveted under-building parking. Pet-friendly with restrictions. Nestled behind the gates of the exclusive Longboat Key Club, this exceptional residence offers the perfect blend of luxury, privacy and breathtaking views—truly one of Longboat Key’s premier addresses.
Listing Agent: Judy Kepecz-Hays (941-587-1700)
1055 GULF OF MEXICO DR #504, LONGBOAT KEY, FL 34228
$1,299,000290 Days on yellowkey MLS ID: A4663883
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1503 Built: 1981 Tax: $14,051 (2024)Community: Beachplace IiiSpa: YesCondo
Taxes:$14,051
Remarks: This direct Gulf-front residence at Beachplace offers an extraordinary opportunity to enjoy the very best of Longboat Key’s beachfront lifestyle. Perfectly positioned to capture unobstructed views of the Gulf of Mexico, this furnished two-bedroom home combines a serene coastal retreat with strong rental potential—producing an average of $70,000 annually in gross rentals. Whether you envision it as your move-in-ready getaway, a property to personalize, or an income-producing property, the possibilities here are unmatched. From the moment you step inside, natural light fills the open floor plan. The welcoming foyer flows into a spacious living and dining area, framed by newer impact-rated walls of glass that extend to the private terrace. This expansive beachfront balcony is a highlight of the home, offering front-row seats to breathtaking sunsets, the sound of gentle waves, and refreshing Gulf breezes. The split-bedroom layout is designed for comfort and privacy. The primary suite enjoys direct terrace access, a large closet, and an en-suite bath with dual vanities. The guest bedroom is equally inviting and privately situated, ideal for hosting family or visitors. Additional features include tile flooring throughout, a well-appointed granite kitchen, and deeded parking—adding everyday ease for seasonal or year-round living. Life at Beachplace feels like a private resort. This sought-after community offers residents 24-hour staffed security, on-site management, a clubhouse perfect for a lively escape, along with Har-Tru tennis courts, a modern fitness center, and heated swimming pool with spa. Pristine beachfront access and lushly landscaped grounds create the ultimate Florida lifestyle. Located on the southern end of Longboat Key, Beachplace provides unmatched convenience. You’re just minutes from the Longboat Key Club’s golf and tennis facilities, the boutique shops and dining of St. Armands Circle, and the vibrant cultural venues of downtown Sarasota—including theaters, galleries, and waterfront parks. From beachside relaxation to world-class dining and entertainment, everything that defines Sarasota living is within easy reach.
Listing Agent: Roger Pettingell (941-387-1840)
5655 GULF OF MEXICO DR #A107, LONGBOAT KEY, FL 34228
$799,00077 Days on yellowkey MLS ID: A4687549
1 Days Off yellowkey (back on 5/28/2026)
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: Under contract-accepting backup offers. 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)
1241 GULF OF MEXICO DR #109, LONGBOAT KEY, FL 34228
$1,099,000260 Days on yellowkey MLS ID: A4667851
REDUCED by $40,000 (3.5%) on 05/27/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2000 Built: 1996 Tax: $14,616 (2025)Community: Water Club At Longboat KeySpa: YesCondo
Taxes:$14,616
Remarks: Live the lavish lifestyle only found at the Water Club on Longboat Key, an idyllic waterfront location with direct access to the white sand beaches only found along the aquamarine waters of the Gulf Coast. This exceptional, beautifully Thomas Moser furnished, 2-bedroom, 2.5-bathroom split plan features spacious en-suite bedrooms with privacy, 10-foot ceilings, floor-to-ceiling hotel-quality hurricane impact windows & sliders, Brazilian Cherry Wood floors, a lovely and convenient powder bath and an incredible master suite with generous walk-in closet and direct access to the private balcony. The masterfully remodeled kitchen showcases custom cabinetry, glass mosaic backsplash, a reverse osmosis faucet, stainless-steel appliances including a Viking stove, Sub-Zero refrigerator and separate dry bar with Sub-Zero wine and beverage refrigerators. Step out onto the extra-large terrace and enjoy the beautiful privacy of the surrounding tropical foliage. Located on the plaza level, you will have quick and easy access to world-class community amenities like 24-hour guard-gated security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. Experience the Water Club...timeless elegance, modern design, and a lifestyle beyond compare. Located a short distance from St. Armands Circle and Downtown Sarasota’s culture, shopping and fine dining.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1211 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$1,648,00031 Days on yellowkey MLS ID: A4694733
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1598 Built: 1985 Tax: $9,234 (2025)Community: PromenadeCondo
Taxes:$9,234
Remarks: Exceptional opportunity to own this beautifully reimagined first-floor residence at The Promenade on Longboat Key, where luxury coastal living meets sophisticated modern design. Completely gutted and renovated from top to bottom, this stunning condominium offers nearly 400 feet of private beach frontage and partial Gulf of Mexico views from almost every room. This spacious two-bedroom, two-bath split floor plan showcases a bright, open-concept design ideal for both entertaining and relaxed everyday living. The designer kitchen flows seamlessly into the expansive living and dining areas and features custom cabinetry, premium countertops with full-height backsplash, and top-tier appliances. A custom dry bar with built-in wine cooler and under-shelf lighting adds an elegant touch for effortless entertaining. Enjoy breathtaking northwest sunset views from the great room or unwind on the private balcony overlooking the Gulf. The luxurious primary suite offers direct balcony access, a large custom walk-in closet, and a spa-inspired en-suite bath complete with a soaking tub, rain shower system, and large-format designer tile creating a true retreat-like atmosphere. The generously sized guest bedroom provides comfort and flexibility for visitors. Every inch of this residence has been thoughtfully curated with exceptional craftsmanship and attention to detail, balancing modern sophistication with everyday comfort. The Promenade offers a true resort-style lifestyle with a 24-hour staffed gatehouse, concierge services, secure under-building assigned parking, heated Gulf-front pool and spa, expansive sundeck with gazebo and grilling area, four Har-Tru tennis courts, fitness center, craft room, and inviting social spaces. Private beach access lined with charming tiki huts completes this extraordinary Longboat Key experience. Rarely does a completely renovated residence of this caliber become available in one of Longboat Key’s most desirable Gulf-front communities. Experience the ultimate in beachfront living, where every day feels like a vacation.
4835 GULF OF MEXICO DR #302B, LONGBOAT KEY, FL 34228
$849,900480 Days on yellowkey MLS ID: A4642701
4 Days Off yellowkey (back on 5/26/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970Monthly Fee: $1,736 Tax: $11,313 (2024)Community: Westchester AptsSpa: NoCondo
Taxes:$11,313
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Experience the ultimate beachfront lifestyle in this stunning 1,393 sq. ft. 2-bedroom, 2-bathroom retreat on Longboat Key. Perfectly positioned on the third floor, this home offers amazing views of the beautiful beaches and the endless Gulf horizon—visible from nearly every room! Wake up to the sound of waves in the master suite, where sliding doors open to a private balcony with breathtaking ocean views. Both bedrooms feature spacious walk-in closets, ceiling fans, while both bathrooms have been fully remodeled with modern, high-end finishes and Toto washlet toilets. The newly updated kitchen boasts a sleek induction stove with a vented range hood, perfect for cooking with a view. New AC, LED lighting, and brand-new impact sliding doors enhance comfort and efficiency. Beyond your private oasis, take advantage of resort-style amenities, including two Gulf-front heated pools unique to the Westchester, Elevators, tennis courts, and direct beach access. Plus, you’re conveniently located just minutes from Publix, top-rated restaurants, and boutique shopping. Enjoy short rides to the vibrant St. Armands Circle and downtown Sarasota, where world-class dining, entertainment, and cultural attractions await. This is coastal luxury at its finest—don’t miss your chance to own a piece of paradise!
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Donna Wrobel (941-518-7950)
2425 GULF OF MEXICO DR #1A, LONGBOAT KEY, FL 34228
$1,595,00081 Days on yellowkey MLS ID: A4688987
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1513 Built: 1973 Tax: $9,602 (2025)Community: Sea Gate ClubSpa: NoCondo
Taxes:$9,602
Remarks: This is the gorgeous ground floor, walk-out unit next to the beach you've been looking for. Do you prefer to live like a single family home, no elevator, and walk straight out to the beach? Then this is the One! Welcome to Sea Gate Club on beautiful Longboat Key, perfectly positioned near mid-island, and close to shopping at Publix or CVS. As you enter this very private End Unit #1A, you're greeted by Direct and Unobstructed Gulf and beach views as far as the eye can see. Unit #1A has been extensively updated over the last few years, featuring an open kitchen with a huge island, updated cabinets and countertops, and gorgeous porcelain tile flooring. 350' of direct and private beach frontage! This unit is offered Turnkey-Fully Furnished with very tasteful furniture that you'll actually want to keep. Sea Gate Club condos are comprised of 89 units, spread across 15 floors. The building has been extensively updated over the past few years. Recent updates include a new pool and hot tub, new roof, newer hurricane rated windows, newer exterior stucco and paint, new elevator doors, climate-controlled bike storage, and paddleboard/kayak storage. Now is the perfect time to buy in this beautiful building, as there are NO current or pending assessments! Hurry before it's gone, this one is beautiful.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228
$2,750,000281 Days on yellowkey MLS ID: A4665247
Bed: 1 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1556 Built: 2025 Tax: $25,560 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Taxes:$25,560
Remarks: Incredible value at St. Regis Longboat Key. The last two one bedroom residences sold for $2,970,000 and $2,975,000. Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulf side living.
Listing Agent: Lynn Morris, Pllc (941-400-4526)
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