Location: Longboat Key
Do Not Show Listings
7147 LA LENAIRE DR, LONGBOAT KEY, FL 34228
$5,000,000220 Days on yellowkey MLS ID: TB8448347
REDUCED by $235,000 (4.5%) on 05/07/2026
Bed: 5 Bath: 5.5 Liv Area Sq Ft: 3503 Built: 1990Monthly Fee: $283 Tax: $33,963 (2023)Community: Jewfish KeySpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$33,963
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2023
Middle School: W.D. Sugg Middle
Remarks: A rare offering on Florida’s coveted west coast, this private island sanctuary feels worlds away yet remains moments from the region’s most beloved coastal destinations. Set on the exclusive 38-acre island of Jewfish Key (accessible only by boat), this remarkable 1.35-acre estate commands its own secluded shoreline and uninterrupted views of crystal clear waters. Inspired by Polynesian architecture and designed to dissolve the boundaries between indoors and out, this estate home unfolds through airy pavilions connected by elevated walkways. Towering palms and lush tropical landscaping envelop the home, while its 18-foot elevation ensures both peace of mind and panoramic, horizon-level vistas. Inside, the freshly reimagined kitchen serves as the gathering heart of the home, with sleek quartz countertops, modern cabinetry, and a spacious oversized island that effortlessly bridges culinary function and relaxed entertaining. Expansive sliding glass doors draw natural light into the living space and frame sweeping views of the sandbar and bay, perfect for sunset watching. The main residence includes four bedrooms and four-and-a-half baths, plus a separate guest suite offering an additional bedroom, kitchen, and full bath, ideal for hosting with comfort and privacy. The primary suite is where the pace of the island truly settles in. Wake up to wide-open bay views, linger with coffee in the sitting area, or enjoy a glass of wine as the sun sinks toward the horizon. The ensuite feels fresh and spa-like, with a soaking tub, walk-in shower, and water views. A series of screened porches and wraparound decks encourage slow living, morning yoga on the deck, afternoon reading in the shade, sunset grilling and cocktails overlooking the Gulf. Outdoors, a newly installed pool and spa with a sun shelf and expansive sundeck overlook the storied Jewfish Key Sandbar. A private dock with jet ski lift offers instant access to calm waters perfect for fishing, snorkeling, paddle boarding, or exploring neighboring Longboat Key and Anna Maria Island, both just minutes away by boat and beloved for dining, boutique shopping, and laid-back coastal culture. Equal parts island hideaway and refined coastal home, this one-of-a-kind property offers the rare combination of true privacy, effortless access, and natural beauty, set against a backdrop of turquoise water, powder soft sand, and endless sky. Here, relaxation, adventure, and natural beauty converge in a setting that feels almost like an escape, yet unmistakably home.
Listing is courtesy of: SIGHT REAL ESTATE, LLC (877-361-0878)
Listing Agent: Chase Moore (727-325-7272)
578 - 580 COMPANION WAY, LONGBOAT KEY, FL 34228
$900,000135 Days on yellowkey MLS ID: A4682264
REDUCED by $99,000 (9.9%) on 05/07/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoApartment
Taxes:$11,672
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value.. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Linh Pham (941-900-6789)
578 COMPANION WAY, LONGBOAT KEY, FL 34228
$900,000135 Days on yellowkey MLS ID: A4682186
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoSingle Family
Remarks: Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.
1241 GULF OF MEXICO DR #506, LONGBOAT KEY, FL 34228
$3,850,00051 Days on yellowkey MLS ID: A4689658
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2650 Built: 1996 Tax: $27,928 (2025)Community: Water Club 01 At Longboat KeyCondo
Taxes:$27,928
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to coastal luxury redefined at the Water Club on Longboat Key. This fully reimagined residence at 1241 Gulf of Mexico Dr, Unit 506 has undergone a complete, top-to-bottom renovation completed in 2025, offering a like-new living experience in one of Florida’s most sought-after beachfront communities. No detail was overlooked—featuring a brand-new designer kitchen with premium finishes, fully renovated bathrooms, new flooring throughout, updated trim, modern lighting, and fresh interior paint. The home is further elevated by a whole-home Lutron system, delivering effortless, customizable lighting control and a true smart-luxury experience. Positioned in the highly desirable south building and an even-numbered unit (ideal for sunset views over the Gulf), this residence captures some of the most breathtaking winter sunset views—where the sun sets between the buildings, creating a rare and unforgettable coastal backdrop. Residents enjoy an unparalleled resort lifestyle at The Water Club, featuring an exceptional collection of amenities including Har-Tru tennis courts, a resort-style beachfront pool and spa, state-of-the-art fitness center, saunas, locker rooms, elegant clubhouse, library, and private event spaces. With 24-hour security, concierge-level services, and meticulously maintained grounds, The Water Club offers the ultimate in privacy, comfort, and luxury coastal living. Whether as a full-time residence or seasonal retreat, this is Gulf-front living at its absolute finest.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Tyler Sajan (877-366-2213)
744 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$1,125,000166 Days on yellowkey MLS ID: TB8463320
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1688 Built: 1963 Tax: $7,142 (2024)Community: Longboat KeySpa: NoSingle Family
Taxes:$7,142
Tax Year: 2024
Remarks: Laid-back Living on Longboat Key -- A Boater's Paradise! Welcome to 744 Jungle Queen Way, a fully renovated, FURNISHED 3-bedroom, 2-bathroom coastal retreat on the stunning Longboat Key! Whether you're a boating enthusiast, a beachcomber, or someone who just loves the island life, this home delivers the ultimate Florida lifestyle. ***Prime Location & Waterfront Living Nestled just seven homes away from Sarasota Bay, this property is a boater's dream with two boat lifts, offering quick access to the Gulf of Mexico's crystal-clear waters. Spend your days fishing, cruising, or island-hopping--all from your backyard! ***Deeded Beach Access - Just 777 Steps to Paradise... take a short stroll across Gulf of Mexico Drive and find yourself on the powdery sands of Longboat Key's legendary beaches. Enjoy sun-soaked days, breathtaking sunsets, and gentle Gulf breezes right outside your door. ***Close to Local Favorites & Hidden Gems. In just a short walk, you'll find island hotspots like the Lo'Key Island Grille, Guppy's Restaurant, and the award-winning Euphemia Haye. A short boat ride, you can enjoy The Shore, Cortez Kitchen, Swordfish Grille, Tide Tables, Anna Maria Oyster Bar, Bridgetenders and Dockside restaurants. ***Modern Updates with Coastal Charm. Step inside to an open-concept layout featuring a spacious, upgraded kitchen with solid wood cabinetry and stone countertops -- perfect for entertaining. The home's split-bedroom design ensures privacy, while the extra-wide lot provides a natural buffer between properties for peace and tranquility. ***Take a short scenic 1-mile stroll from your front door to enjoy the beauty of Florida's coastal landscape at Joan M. Durante Park and the Sarasota Bay overlook dock for a peaceful escape. This 32-acre bay front nature preserve features winding boardwalks, shaded trails, and scenic waterfront views, perfect for birdwatching, peaceful walks, or catching a sunrise over the mangroves. ***Your Slice of Island Paradise Awaits! Whether you're looking for a full-time residence, a vacation getaway, or an investment property, this home captures the essence of laid-back luxury. Don't miss your chance to live the dream on Longboat Key! ***Schedule your private showing today!
Listing is courtesy of: YOUR HOMETOWN REALTY, INC. (813-645-7007)
Listing Agent: Teddi Aberle (813-645-7007)
4380 EXETER DR #101, LONGBOAT KEY, FL 34228
$389,500105 Days on yellowkey MLS ID: A4686109
REDUCED by $500 (0.1%) on 05/06/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1970 Tax: $3,148 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$3,148
Remarks: Investor alert. Great investment opportunity! Condominium is in great condition. Best price for two-bedroom, two-bath condominium in sought after community of Longboat Harbour. Motivated sellers, ready to have a new buyer enjoy this lovely waterfront first-floor end-unit condominium. New roof, all assessments paid, granite countertops, kitchen open to living area. All glass lanai, tile throughout main living, carpet in bedrooms were in the bedrooms but carpet removed for new flooring to be installed. A huge plus: end unit, close to the beach, washer and dryer are in the unit. Hurricane shutters on rear of unit. Additionally, the beautifully renovated recreation room overlooking the bay serves as 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 along the Gulf beach. This exceptional opportunity offers an unparalleled lifestyle in one of Longboat Key's active, social and vibrant communities! Seize the opportunity to experience waterfront living at its finest. This condominium community was not impacted by hurricane flood waters, according to the owner. Make this beautiful community your next home!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Freiwald (941-256-6775)
5311 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228
$799,00063 Days on yellowkey MLS ID: A4691314
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1110 Built: 1973 Tax: $3,363 (2025)Community: Mccalls Beach CastleSpa: YesCondo
Taxes:$3,363
Remarks: Turnkey furnished and positioned just steps from the Gulf’s sandy shoreline, this first-floor residence at Beach Castle on Longboat Key offers a compelling combination of coastal living and proven rental potential. With flexible daily or weekly rental allowances, this two-bedroom retreat presents an exceptional opportunity for personal use, income generation, or both. The light-filled interior features an open layout designed for ease and comfort, where the kitchen, dining, and living areas flow together naturally. Oversized tile flooring, updated impact glass, and sliding doors enhance both durability and livability, while the kitchen is well-appointed with granite countertops, solid wood cabinetry, stainless steel appliances, and built-in shelving—creating a functional space for everyday living or hosting. Floor-to-ceiling sliders lead to a private patio and screened lanai, offering a seamless transition to the outdoors and placing you just moments from the beach. The split-bedroom plan provides added privacy, with the primary suite enjoying direct access to the outdoor space, while the guest bedroom is comfortably sized with its own en-suite bath. Set within the boutique Beach Castle community, residents enjoy a unique beach-to-bay lifestyle with deeded Gulf access, a heated swimming pool and spa, grilling areas, and a fishing pier with day dock on Sarasota Bay. Lush landscaping and well-maintained grounds create a relaxed, resort-style setting that enhances both owner enjoyment and guest appeal. Located on the desirable north end of Longboat Key, this property is just minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic biking and walking paths. A short drive south brings you to the Longboat Key Club, St. Armands Circle’s dining and boutiques, and downtown Sarasota’s renowned cultural venues, waterfront parks, and year-round events. With strong rental history, immediate beach access, and a turnkey presentation, this Beach Castle residence offers a rare opportunity to enjoy the best of Longboat Key—whether as an investment, a private getaway, or a combination of both.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
4621 GULF OF MEXICO DR #10D, LONGBOAT KEY, FL 34228
$649,900205 Days on yellowkey MLS ID: TB8453208
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 756 Built: 1973 Tax: $8,174 (2024)Community: Longboat Key Casa Del MarCondo
Taxes:$8,174
Remarks: Huge Price Adjustment! PRICED TO SELL!!! Check out these consistently strong revenue numbers: 2023: $55,764, 2024: $54,307.46, 2025: $62,007.40!!! Whether you choose resort style living or just want to enjoy vacationing at the beach while earning income when you are not using your condo, this is the place for you! The resort is right on the beach and amenities include a large heated pool, several grills, tennis, basketball and pickleball. Repeat guests have commented choosing this unit because of its location and that they love having a screened in patio to enjoy morning coffee or simply the warm gulf air. Casa Del Mar is one of the few resorts in Longboat permitted to offer short term rentals and also offers some of the lowest property management fees as well. Come check out this turnkey 2 bedroom 2 bath condo and make beach living your reality! (approximately 900 sqft with screened in lanai)
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Michelle Furiato (941-224-5246)
847 EVERGREEN WAY, LONGBOAT KEY, FL 34228
$599,000282 Days on yellowkey MLS ID: A4665172
REDUCED by $10,000 (1.6%) on 05/04/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1440 Built: 1991 Tax: $8,510 (2024)Community: Cedars East Sec 3Townhouse
Taxes:$8,510
Remarks: Refined Coastal Living with Proven Income Potential – Experience the best of Longboat Key in this impeccably appointed, turnkey furnished residence within the coveted Cedars East Tennis Resort. This elegant 2BR/2.5BA townhome spans 1,440 square feet of thoughtfully curated living space, where tasteful coastal design meets modern comfort. The gourmet kitchen is adorned with granite surfaces and flows seamlessly into a bright, open living area designed for effortless entertaining. A tranquil, private lanai invites you to unwind amid lush tropical surroundings. The primary suite serves as a serene retreat, complete with dual vanities and a spa-inspired ambiance, while upstairs laundry enhances everyday ease. With a strong history of rental performance, this property offers a rare opportunity to blend lifestyle with investment. Residents and guests enjoy an array of resort-caliber amenities, including championship Har-Tru tennis courts, a heated Olympic-style pool, fitness center, and exclusive bayfront features such as a kayak launch, fishing pier, and scenic mangrove boardwalks. An on-site dining option adds to the effortless luxury. Ideally located just moments from the beautiful beaches of Longboat Key, the boutiques and dining of St. Armands Circle, downtown Sarasota, and Anna Maria Island. A distinctive offering for the discerning buyer seeking both coastal elegance and exceptional return on investment. No flood damage | New A/C (2025)
Listing Agent: Kiki Bowers (941-718-3435)
2295 GULF OF MEXICO DR #23S, LONGBOAT KEY, FL 34228
$1,295,000247 Days on yellowkey MLS ID: A4669226
REDUCED by $100,000 (7.2%) on 04/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $9,812 (2024)Community: Islander Club Of LongboatSpa: NoCondo
Taxes:$9,812
Remarks: Set directly on the shores of the Gulf of Mexico, this beautifully renovated residence in the Islander Club captures the essence of Longboat Key beachfront living. Located in the desirable South Tower, this 2BR/2BA home showcases a fresh coastal design with wide-plank flooring, crown molding, recessed lighting, and an open layout oriented to the water. The kitchen exudes coastal charm with stone countertops, shaker cabinetry, stainless-steel appliances, and a sea-glass tile backsplash. Both baths have been redone with refined finishes, glass-enclosed showers, and clean modern tilework. Floor-to-ceiling sliders open to an expansive covered terrace—perfect for outdoor dining, lounging, and taking in sweeping Gulf views. The primary suite also enjoys terrace access and an endless horizon of turquoise water. Residents of the Islander Club enjoy 400 feet of private beach, a Gulf-front pool, fitness center, tennis courts, pickleball, library, social lounge, and on-site management within two secure towers and gated entry. The recently updated common areas - including the elegant lobby and clubroom - offer a stylish, contemporary ambiance overlooking the Gulf. Ideally positioned near St. Armands Circle and Sarasota’s world-class dining, shopping, and cultural attractions, this residence offers an effortless blend of comfort, sophistication, and beachfront tranquility.
Listing Agent: Bruce Myer (941-376-5311)
535 SANCTUARY DR #C807, LONGBOAT KEY, FL 34228
$3,750,000144 Days on yellowkey MLS ID: A4680240
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2580 Built: 1990 Tax: $25,298 (2025)Community: Sanctuary IvSpa: YesCondo
Taxes:$25,298
Elementary School: Southside Elementary
High School: Booker High
Middle School: Pine View School
Remarks: Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Sarasota. *Now Unfurnished*. Total renovations completed in 2023 with nothing overlooked, including but not limited to EFCO turtle-approved glass, high-impact double pane hurricane sliders and windows, crystal custom kitchen cabinets by SRQ Custom Cabinetry, Thermador appliances including induction cooktop, wall-mounted microwave and convection oven, side-by-side Thermador refrigerator, Wi-Fi enabled dryer and hood fan, laundry room with added pantry features and a newly created breakfast bar. Complete water filtration system and quartz countertops throughout, with 5.5-inch baseboards with custom-milled crown molding and trim, solid wood doors, rectified 12-by-60-inch porcelain tile flooring, and custom built-ins in living room and primary bedroom. Hunter Douglas remote-controlled blinds, 10-foot-high ceilings complete with skylights, tankless hot water system, and two zoned air conditioning units installed in 2019 and 2023. Amenities include cable, water and internet. New roof in 2024. Storage locker with under-building parking. Nearly 18 acres with 1,200 feet of Gulf of Mexico beachfront, an Olympic-sized heated pool and spa with extensive pool decks, a fire pit and gazebos to provide shade. A 24/7 guard gate, Har-Tru tennis courts, on-site management, and a two-story clubhouse come complete with a fitness center, showers, saunas and a large entertaining room with catering facilities. Membership to the Longboat Key Club is available which would include six restaurants, 45 holes of golf, 20 tennis courts plus other amenities. You are close to shopping, Publix, CVS, places of worship, a library, town hall and banks, St. Armands Circle along with Sarasota and all it offers.
Listing Agent: Dennis Girard (941-809-0041)
2425 GULF OF MEXICO DR #10F, LONGBOAT KEY, FL 34228
$1,495,000354 Days on yellowkey MLS ID: A4656887
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1513 Built: 1973 Tax: $14,482 (2024)Community: Sea Gate ClubSpa: NoCondo
Taxes:$14,482
Remarks: Price Reduced $100k—Welcome to Sea Gate Club #10F, a rare 10th-floor corner unit with sweeping, unobstructed Gulf views on Longboat Key. This 2-bed, 2-bath residence is filled with natural light and offers stunning sunsets from nearly every room—an ideal coastal retreat for relaxing or entertaining. Located in an intimate 89-unit beachfront community, Sea Gate Club offers a quiet, refined lifestyle with extensive recent upgrades, including impact windows, new roof, exterior renovation, pool, elevators, and more—no pending special assessments. Enjoy resort-style amenities: Gulf-front pool and spa, fitness center, tennis court, library, and social spaces, plus beachside extras like tiki huts and storage for bikes and water gear. Just minutes from St. Armands Circle, you’ll have easy access to dining, shopping, and island charm. Private, peaceful, and rarely available—this is Gulf-front living at its best.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-748-6300)
Listing Agent: Erica Thomas, Llc (941-799-9365)
4380 EXETER DR #H202, LONGBOAT KEY, FL 34228
$499,000228 Days on yellowkey MLS ID: A4671530
REDUCED by $21,000 (4.0%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $6,314 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$6,314
Remarks: Experience the ultimate Bay-to-Beach lifestyle in this turnkey 2-bedroom, 2-bath condo at Longboat Harbour, where nearly every room offers sparkling water views and a sense of calm that only waterfront living can bring. Perfect for investors or seasonal residents, this home combines desirable updates with a lifestyle that’s hard to beat. Fully updated in 2025, this home blends modern luxury with coastal charm. LVP flooring, textured ceilings, and fresh paint flow throughout, while the brand-new kitchen boasts with all-white cabinetry, coffee bar, coastal glass backsplash, and quartz countertops. The master suite features custom closet doors, a new porcelain shower with frameless glass, porcelain flooring, and a quartz-top vanity with Bosch washer/dryer in the bath. The hall bath includes a new porcelain shower/tub combo, stylish vanity with quartz countertops, and contemporary Euroflush toilets. Every detail is designed to make the interior as inviting as the stunning views outside. Every update you could hope for in a ready-to-enjoy condo! Step outside and enjoy the resort-style amenities of a vibrant waterfront community. Longboat Harbour offers four heated pools, tennis and pickleball courts, a recreation hall, billiards, game rooms, docks with sailboat access (no bridges to the bay), and a fitness center. Social committee events, on-site grills, and beautiful landscaping surround you at every turn. For beach lovers, the private deeded beach access at 4415 Gulf of Mexico includes a beach house with restrooms, showers, and reserved parking. A short drive from Longboat Key, St. Armands Circle, and downtown Sarasota, you’ll find boutique shops, delightful dining, arts, festivals, and the wonder of Selby Botanical Gardens. Watch Gulf sunsets paint the sky while manatees, ospreys, and egrets play in the waters below… this condo is all about a life of fun, relaxation, and unforgettable moments.
Listing Agent: Ryan Skrzypkowski (941-328-8307)
550 YARDARM LN, LONGBOAT KEY, FL 34228
$3,775,000218 Days on yellowkey MLS ID: A4672604
0 Days Off yellowkey (back on 5/1/2026)
REDUCED by $20,000 (0.5%) on 04/28/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4281 Built: 2006Monthly Fee: $23 Tax: $16,615 (2024)Community: Country Club Shores Sec 02Spa: YesSingle Family
Taxes:$16,615
Remarks: Under contract-accepting backup offers. Motivated seller ….ELEVATED Waterfront Luxury on Longboat Key! Welcome to 550 Yardarm Lane, where the elegance of Longboat Key meets the ease of Florida’s coastal lifestyle in the coveted Country Club Shores. This waterfront masterpiece isn’t just a home, it’s your front-row seat to paradise, where boating, beach walks, and year-round sunshine are part of everyday life. Step inside and be instantly captivated by sparkling water views, soaring spaces, and the perfect blend of casual comfort and refined luxury. Designed for both relaxation and unforgettable entertaining, this 5-bedroom, 5.5-bath retreat is tailor-made for hosting family and friends in style. PRIME WATERFRONT LIVING - Private dock on a deep-water canal with no-bridge access to the bay, perfect for your weekend cruiser. LIGHT & BRIGHT OPEN LAYOUT - Walls of glass bring the outdoors in, filling the home with sunshine and stunning water views. ELEVATOR - Effortless access to main living levels from the three car garage. CHEF’S DREAM KITCHEN - High-end appliances, custom cabinetry, and an oversized island ready for gourmet meals and lively gatherings. LUXURIOUS SUITES - Owner’s retreat with a private balcony, spa-inspired bath, and dual walk-in closets. MOVIE ROOM - Your own private theater for cozy nights in. OUTDOOR OASIS - infinity pool, spacious patio, and lush landscaping for poolside lounging or sunset soirees. All this just steps to your DEEDED BEACH ACCESS and minutes from the world-class dining, shopping, and cultural treasures of St. Armands Circle and Downtown Sarasota. Whether you’re dreaming of a full-time Florida home or a seasonal escape, 550 Yardarm Lane delivers the ultimate Longboat Key lifestyle.
Listing is courtesy of: QUEST PROPERTIES INC (941-504-1111)
Listing Agent: Melanie Russell (941-879-5882)
948 SPANISH DR S, LONGBOAT KEY, FL 34228
$1,199,000107 Days on yellowkey MLS ID: A4685572
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1399 Built: 1968 Tax: $4,945 (2025)Community: Spanish Main Yacht Club CondoVilla
Taxes:$4,945
Remarks: Stunning full bay views as you enter this jaw-dropping magnificent, completely custom renovated stand-alone villa on Sarasota Bay. Professionally designed starting with an 18-by-11-foot gourmet kitchen. With 10-12-foot wood beam ceilings, a beautiful 12-foot quartz island that seats 10-plus people, solid wood cabinetry, Café’ brand double oven, refrigerator with two additional drawers, stainless steel appliance, huge undermount sink, glass backsplash, separate wet bar and more. The 2-by4-foot white porcelain rectangular tile flows seamlessly from room to room with water views that entertain you every moment of every day. With the Intracoastal Waterway just beyond the brick paver back patio, the wildlife is abundant, more than you can imagine, with morning sunrises that softly greet you as you awaken to a true slice of paradise. The entire glass-enclosed 23-by-12-foot lanai brings so much light, brightness and cheerfulness that it makes your heart smile. The end unit offers privacy and protection with lush green mangroves creating a protected area plus easy access for entering the water, going for a swim, fishing or kayaking. Back to the renovations, the main bedroom en suite offers privacy with upscale bath appointments, a double sink, and large designer shower. The enclosed laundry area right off the bedroom was carefully crafted with a walk-in closet, extra storage room and a rare whole-house water purification system. Not to mention all hurricane windows and doors throughout with additional footings, foam support and steel beams under the sliding doors to ensure structural integrity and peace of mind. All appliances are 2025, LG Thin Q washer and dryer, Café kitchen appliances, tankless hot water tank, custom fan and lights, all new plumbing and electrical as the home was taken down to the studs. PVC sewer lines completely replaced all cast iron pipes. New tile roof in 2025. There is nothing to do except move in and relax. You will not be disappointed. All FEMA regulations have been completed, including inspections. Vibrant waterfront 55-plus community with 40-slip marina and deeded beach access to gorgeous beaches of Longboat Key. Close to restaurants, shops, renowned St. Armands Circle, plus 30 minutes to Sarasota International Airport. Take a look.
2039 GULF OF MEXICO DR #G3-207, LONGBOAT KEY, FL 34228
$550,000358 Days on yellowkey MLS ID: A4657767
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1974 Tax: $5,281 (2024)Community: SeaplaceSpa: NoCondo
Taxes:$5,281
Remarks: THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor (elevator access on the north end) of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, crown molding, no popcorn ceilings, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care and the coastal vibe! This building is located directly adjacent to the Har-Tru tennis courts, perfect for the avid player! Seaplace is a Gulf front community situated on lushly maintained grounds and offers not only tennis courts, a secure guarded gated entry, clubhouse, two heated pools/spas, fitness, Gulfside BBQ, organized social functions, onsite management and the icing on the cake is direct beach access! Residence comes completely furnished, assigned parking space #115, (north side of the building) Perfect for your second home and income protection, with a 2-month minimum rental period. Seaplace is located on beautiful Longboat Key convenient to grocery shopping, banking, and the best shopping on St. Armand's Circle! Or make a reservation at any number of first-class restaurants on the Key, and dine waterside, or find a nice cozy quiet booth inside and take in one of nature's most beautiful gifts of a sunset, and if you are lucky, you just may see the dolphins diving and playing! Come off the beach at the south end and you are immediately in downtown Sarasota, where you can catch any number of plays, or a live band for evening entertainment. The weekend offers a sidewalk Farmer's Market, with an assortment of vendors! Whatever time you have planned to be here, may just not be enough!!!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Diane Fogo Harter (941-445-2431)
2120 HARBOURSIDE DR #623, LONGBOAT KEY, FL 34228
$1,095,00095 Days on yellowkey MLS ID: A4686721
REDUCED by $130,000 (10.6%) on 04/28/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988Monthly Fee: $137 Tax: $11,079 (2025)Community: Fairway Bay AtriumSpa: YesCondo
Taxes:$11,079
Middle School: Booker Middle
Remarks: Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy environment perfect for both entertaining and everyday comfort. The gourmet kitchen is outfitted with GE Profile appliances, custom soft-close cabinetry, and ample storage, offering both style and functionality. The primary suite is a serene retreat featuring a spacious walk-in closet, additional storage, and a beautifully updated en-suite bath with a large walk-in shower. From both the living room and the primary suite, step onto the expansive north-facing balcony to take in the tranquil Sarasota Bay views, where you can enjoy the morning sunrise and the soft glow of the evening sky. The second bedroom is generously proportioned and easily accommodates a king-size bed, creating a luxurious space for guests. The third bedroom is also spacious, complete with a custom built-in, ideal for a guest room, home office, or flexible living area. A thoughtfully designed guest bath ensures privacy and convenience for family or visitors. This unit also includes the ease and security of one covered parking space beneath the building. Fairway Bay residents enjoy an exceptional suite of amenities including two heated pools, a spa, a clubhouse, a fitness center, tennis and pickleball courts, and private beach access on Longboat Key. With the shops, dining, and vibrant lifestyle of St. Armands Circle just minutes away, this residence combines the best of convenience and refined waterfront living.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1065 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$629,000245 Days on yellowkey MLS ID: A4669086
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1172 Built: 1981 Tax: $7,875 (2024)Community: Beachplace IiiCondo
Taxes:$7,875
Remarks: One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true coastal feel. The residence features brand-new, impact-rated floor-to-ceiling sliding glass doors that brighten the living and dining areas and enhance indoor-outdoor living. The open-concept layout connects the kitchen, dining, and living spaces, making it well suited for everyday living or entertaining. A split-bedroom floor plan provides privacy, with the primary suite offering direct access to the terrace. One assigned parking space is included, and the unit is ready for personalization or updating. BeachPlace is a gated, Gulf-front condominium community offering 24-hour security and resort-style amenities, including a clubhouse, heated beachfront pool and spa, tennis courts, fitness center, and a private boardwalk with direct beach access. Seasonal beach service with lounge chairs and umbrellas is provided. Conveniently located near golf, marinas, dining, and shopping, and just a short drive to downtown Sarasota, this property offers flexibility as a full-time residence, seasonal getaway, or investment opportunity.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: John Esser (515-306-8505)
350 GULF OF MEXICO DR #211, LONGBOAT KEY, FL 34228
$938,500267 Days on yellowkey MLS ID: A4667037
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2394 Built: 1992 Tax: $9,083 (2023)Community: Tangerine Bay ClubCondo
Taxes:$9,083
Remarks: Experience resort-style living at Tangerine Bay Club, a gated sanctuary on the desirable south end of Longboat Key. This impeccably maintained end-unit residence offers 2,400 square feet of refined living space with lush Sarasota Bay views and unmatched proximity to the area’s top attractions. Minutes to St. Armands Circle, downtown Sarasota, and steps to Dry Dock Marina and Restaurant. No current assessments and meticulously maintained grounds. Thoughtful floor plan with multiple terrace access points to enjoy morning and afternoon sun. This three-bedroom, two-and-a-half-bath, plus den, includes an oversized private two-car garage. There is also a natural gas barbecue on the front terrace. Resort-style amenities at Tangerine Bay Club include a heated pool, lap lane, heated spa, tennis, and regulation pickleball courts, a clubhouse with a fitness center, and a vibrant social room and calendar (happy hours, pickleball, cultural excursions). Freshly renovated boat dock, two kayak launches, a fishing pier, and prime fishing directly on Sarasota Bay. Enjoy just “sittin’ on the dock of the bay” watching the dolphins roll in. Take a scenic nature walk between Sarasota Bay and Quick Point Nature Preserve. Ownership includes (optional) membership to the Bay Isles Beach Club facilities for just $600.00 per year (application required).Longboat Key is renowned for golf, tennis, fine dining, boating, and world-class fishing. Be sure to explore the newly opened St. Regis resort, just a short stroll to the north on the beach side. Ongoing management ensures a carefree ownership experience with no special assessments anticipated. Recent capital projects (painting, waterproofing, elevator rebuilds, 2024 roof replacements, exterior tile walkway updates) have been completed and funded, with milestone inspections cleared. Pet-friendly, gated entry, and a day dock for fishing. This residence offers the perfect blend of luxury, convenience, and peace of mind—an ideal retreat for those seeking sophistication and coastal living at its finest. DON’T JUST THINK ABOUT IT, COME EXPERIENCE IT FOR YOURSELF AND MAKE IT YOUR REALITY.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
592 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
$4,000,00059 Days on yellowkey MLS ID: A4691388
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 3600 Built: 2027 Tax: $6,949 (2025)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$6,949
Remarks: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, a premier luxury builder known for crafting high-end coastal residences with exceptional attention to detail and durability, this stunning new construction home at 592 Juan Anasco Dr offers an unparalleled blend of sophistication, comfort, and waterfront living. Perfectly positioned on a canal-front lot in Longboat Key, this 5-bedroom, 5.5-bath residence is thoughtfully designed to capture the essence of refined coastal living. Expansive windows, soaring ceilings, and a light-filled interior create an inviting atmosphere, while the home’s modern coastal aesthetic is complemented by carefully curated finishes and timeless design elements that elevate every space. The spacious and well-appointed floor plan offers a seamless balance of functionality and privacy, making it ideal for both everyday living and elevated entertaining. Generous living areas provide a welcoming environment for gathering, while the primary suite serves as a true retreat—offering a peaceful escape with a spa-like feel. Each additional bedroom is designed with comfort in mind, providing flexibility for guests, family, or extended stays. Step outside to your private waterfront oasis, where a resort-style setting invites relaxation and effortless entertaining. Whether hosting friends, enjoying quiet evenings by the water, or taking advantage of Florida’s year-round sunshine, this outdoor space is designed to be experienced. With direct canal access, boating enthusiasts will appreciate the ability to enjoy the Intracoastal lifestyle right from their backyard. Built to meet current FEMA guidelines and elevation requirements, this home offers enhanced protection, improved insurance efficiency, and long-term peace of mind—an essential advantage for waterfront properties. The elevated construction is thoughtfully designed to perform in coastal conditions while maintaining both functionality and architectural appeal. Living on Longboat Key means embracing a lifestyle that is both refined and relaxed. Known for its pristine Gulf beaches, world-class golf, and exclusive residential feel, the island offers a quieter, more private alternative to neighboring destinations. Residents enjoy convenient access to the renowned shops and restaurants of St. Armands Circle, the cultural attractions of downtown Sarasota, and nearby marinas, beach clubs, and nature preserves. From morning walks along the shoreline to sunset cruises and evenings of coastal dining, every day feels like a getaway. This is more than a home—it’s a lifestyle defined by waterfront elegance, modern construction standards, and one of Florida’s most sought-after coastal communities. Pricing, availability, and final details subject to adjustment prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
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