Location: Longboat Key
Keyword(s): Bayshore High
Keyword(s) High School: Bayshore High
Do Not Show Listings
765 SAINT JUDES DR N, LONGBOAT KEY, FL 34228
$1,499,90089 Days on yellowkey MLS ID: A4683420
REDUCED by $80,100 (5.1%) on 04/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1900 Built: 1963 Tax: $14,125 (2025)Community: Longboat KeySpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,125
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Best Waterfront Value on Longboat Key – CANAL-FRONT Home with Deeded Private Beach Access. Exceptional opportunity to own a fully renovated CANAL-FRONT residence on highly sought-after Longboat Key. Notably, the property was appraised prior to renovation completion for more than the original asking price, creating a rare built-in equity opportunity. This 4-bedroom, 2-bathroom coastal retreat offers the perfect blend of luxury, location, and lifestyle, complete with DEEDED PRIVATE BEACH ACCESS to the Gulf of America. Positioned along 132 linear feet of canal frontage, the property features a seawall and kayak launch (2020) and provides direct boating access to Sarasota Bay and beyond. The home has undergone a comprehensive interior and exterior renovation, with virtually everything NEW apart from the home’s foundation, delivering exceptional move-in-ready peace of mind. 2025 Improvements Include: • New roof (2025) • New flooring (2025) • New interior walls (2025) • Full home renovation – interior & exterior (2025) • New AC systems (2025) • New decking (2025) • New cabinets (2025) • New landscaping (2025) • New electrical systems (2025) Major System & Feature Upgrades: • Electrical panel (2022) • New plumbing (2022) • Commercial-grade whole-home surge protector (2022) • Tankless gas water heater (2022) • New sliding glass doors (2022) • New impact windows (2022–2023) • Impact-rated garage doors (2022) • New pavers (2022) • New ductwork (2020) • Seawall & kayak launch (2020) PGT high-impact sliding glass doors, new impact windows, and impact-rated French doors enhance storm protection, energy efficiency, and natural light. Interior highlights include vaulted ceilings, expansive water views, two electric fireplaces, and elegant wood-look ceramic tile flooring throughout. The bright, open layout is designed for effortless coastal living. The beautifully updated kitchen features solid wood cabinetry, soft-close hardware, marble-look quartz countertops, a gas stove, premium stainless-steel appliances, a copper hood, and a copper farmhouse sink. Updated bathrooms showcase sophisticated Italian marble-look ceramic tile, including an alcove soaking tub in the primary suite and a walk-in rain shower. Outdoor living is elevated by a spacious screened porch overlooking the canal and backyard. The yard is enclosed with sleek black aluminum fencing and offers ample room for a future pool. Additional Highlights: • Higher elevation than many ground-level Longboat Key homes • 132 ft of canal frontage • Direct boating access • Deeded PRIVATE beach access Ideally located near Cedars East Tennis Resort & Club, offering nine tennis courts, three pickleball courts, and a large community lap pool, as well as Joan Durante Park (34 acres). Dining, shopping, and island amenities are all within close proximity. Offered fully furnished / TURNKEY, this home is ready for immediate enjoyment as a primary residence, vacation retreat, or investment opportunity. Boating + Beach + Extensive 2025 Renovation = Rare Longboat Key Opportunity. Schedule your private tour today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Kalison Nix (941-900-9189)
690 FOX ST, LONGBOAT KEY, FL 34228
$725,00098 Days on yellowkey MLS ID: A4682225
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1967 Tax: $10,397 (2025)Community: Longbeach On Longboat KeySingle Family
Taxes:$10,397
Remarks: Buy the beach house, now is your opportunity! New unbelievable price on this fully renovated and turn-key furnished Village of Longboat Key Home. Take Advantage Today. Brand new Roof, New Hurricane glass throughout, Full interior renovation with new furnishings, Block home on a Beautiful private lot with outdoor living space and room for a Pool, steps away from white sand and turquoise water, rent-ability with the seller averages $55,000 a year in gross rental income while still enjoying personal use. Buy this property at an unbelievable price, rent it when you're not using it, and enjoy it for decades to come. Coastal Elegance Meets Island Ease in Longboat Key's Coveted Village. Discover a sanctuary of sophistication at the exclusive North Tip of Longboat Key. Located in the heart of historic Long Beach Village, this is more than a home; it's the ultimate island lifestyle, delivered. Just a short, serene stroll separates you from the pristine beach and the island's best waterside dining. This property has been meticulously and fully remodeled, representing a rare "move-in ready" opportunity where every detail has been elevated. From top to bottom, inside and out, virtually nothing has been untouched. A Home Designed for Seamless Living: Open Concept: Step into an airy, open-plan great room, anchored by a brand-new kitchen - perfect for hosting intimate gatherings or unwinding after a day on the water. Chef's Delight: The remodeled kitchen is a masterpiece featuring stunning marble countertops, custom cabinetry, all-new luxury appliances (including a mini wine refrigerator), and a chic island/bar. High-End Finishes: Enjoy the cohesive flow of new luxury vinyl plank flooring throughout every room, complemented by fresh, designer-selected interior paint. Peace of Mind: Recently installed, all new windows and sliding glass doors are Miami-Dade impact resistant, offering superior protection and efficiency. Also a brand new architectural three-tab shingle roof was just installed. Your Private Island Retreat: Spa-Inspired Baths: Both the master and second bathrooms have been fully renovated with premium stone shower flooring, elegant new tiles, and updated fixtures. Outdoor Oasis: Off the master suite, a new impact-resistant glass door opens to a spacious, private backyard. The highlight is the expansive, screened-in porch that wraps around the back of the house, overlooking a charming outdoor fire pit and grilling area. Beach Ready: An exterior shower and dedicated storage for your gear make rinsing off after a day at the beach effortless. The Village Lifestyle: To know The Village is to fall in love with its relaxed, yet refined rhythm. This community places everything you desire at your fingertips: secluded walking trails, Bay access, community docks, and the island's best beach access. The Village is one of the few places on Longboat Key where the golf cart isn't just legal, it's the preferred, fun, and convenient way to live. Come and see it today.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228
$999,999104 Days on yellowkey MLS ID: A4680786
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1846 Built: 1960 Tax: $17,419 (2024)Community: Sleepy Lagoon ParkSingle Family
Taxes:$17,419
Tax Year: 2024
Remarks: Imagine living the coastal lifestyle only dreams are made of! Wake each morning to the sunrise over your local beach—just a short stroll down the street—where you can sink your toes into sugary white sand, take an early walk, or collect seashells along the shore. Return home to enjoy coffee outdoors by your heated pool, relaxing on the deck as tranquil water views set the tone for the day. Take a refreshing dip, then unwind as nature’s canvas unfolds before you, with shifting light and brilliant shades of blue and azure. In the evening, hop on your boat from your backyard and cruise effortlessly to waterfront restaurants and sunset destinations. With a 20,000-lb boat lift, personal watercraft lift, and a 40-foot dock on a deep-water canal, you’ll enjoy immediate access to Sarasota Bay, the Intracoastal Waterway, and the Gulf—with no fixed bridges along the way. End your days with breathtaking sunsets as the sky ignites in color, dolphins play, and manatees glide by. Inside, the home offers an optimal floor plan ready for your personal touches. The spacious eat-in kitchen features an expansive island perfect for casual entertaining, complemented by new stainless-steel appliances. A wall of sliding glass doors seamlessly blends indoor and outdoor living, filling the home with natural light and water views. All main living areas open to the pool and outdoor spaces. Recent updates include a new AC system and a recently refinished pool. The home offers three bedrooms and four baths, with the flexibility to modify the layout or easily add a fourth bedroom. A wood-burning fireplace adds warmth and charm to the living room. Located on the barrier island of Longboat Key, this exceptional property is perfectly suited for the most discerning buyers. Enjoy nearby golf, pickleball, boutique shopping, and dining, with St. Armands Circle and downtown Sarasota just minutes away. Convenient access to SRQ Airport makes this an ideal full-time residence or luxury vacation retreat. Call today to schedule your private showing and experience coastal living at its finest.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kathy Cahill (941-807-3565)
718 SPANISH DR N, LONGBOAT KEY, FL 34228
$435,00054 Days on yellowkey MLS ID: A4687749
REDUCED by $14,500 (3.2%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1327 Built: 1969 Tax: $2,539 (2025)Community: Spanish MainVilla
Taxes:$2,539
Remarks: Discover Longboat Key waterfront living at its very best at 718 Spanish Dr N, a beautifully updated freestanding villa in the sought-after Spanish Main Yacht Club. This home has been completely renovated to today’s highest standards following Hurricane Ian, delivering a fresh, high-end coastal finish throughout with meticulous craftsmanship and premium materials. Just steps from your door, enjoy private deeded beach access to the powder sands and turquoise color of the Gulf of Mexico — perfect for sunrise walks, beachcombing, or sunset gatherings. Boaters will appreciate the community’s deep-water marina with boat slips priced around $1,200 annually that have direct access to the Intracoastal Waterway, and quick passage to the open Gulf, along with kayak racks and fishing right at hand. Inside, the bright open-concept 2-bedroom, 2-bath villa showcases an elevated, contemporary coastal design. The gourmet kitchen is a true entertainer’s dream, featuring sleek modern cabinetry, elegant stone countertops, a spacious island, and high-end stainless steel appliances. Sunlight pours through the generous windows and sliders, highlighting the beautiful new flooring that flows seamlessly into the living and dining areas. A sun-drenched Florida room/lanai offers flexible space, ideal for a home office, artist studio, or casual living — all overlooking lush tropical landscaping and a peaceful community setting. Both bedrooms are generously sized with ample closet space, while the updated baths feature contemporary fixtures and finishes for a spa-like feel. Additional highlights include a private outdoor shower, a spacious carport for your island toys, and thoughtful storage throughout. This vibrant, friendly 55+ community (can be under 55 to purchase) offers a heated pool, a clubhouse with marina views, shuffleboard courts, and a welcoming social atmosphere. Maintenance-free living, beautifully landscaped grounds, and covered parking complete the carefree Longboat Key lifestyle. Whether you seek a full-time waterfront residence, seasonal escape, or outstanding investment, 718 Spanish Dr N offers turnkey luxury with effortless deeded beach access and marina convenience in one of Longboat Key’s most desirable waterfront enclaves. Minutes to St. Armand's Circle, downtown Sarasota, and Anna Maria Island, yet tucked away in paradise. Don’t miss this rare opportunity to own a freshly renovated gem in Spanish Main Yacht Club — where high-end coastal living meets the best of island boating and beach life!
Listing is courtesy of: SARASOTA REAL ESTATE GROUP (941-922-8400)
Listing Agent: John Woodward (941-922-8400)
900 SPANISH DR N, LONGBOAT KEY, FL 34228
$750,00028 Days on yellowkey MLS ID: A4690879
0 Days Off yellowkey (back on 5/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1423 Built: 1971 Tax: $4,203 (2025)Community: Spanish Main Yacht Club CondoSpa: NoVilla
Taxes:$4,203
Remarks: Under contract-accepting backup offers. This must-see hidden gem on the north end of Longboat Key offers a quintessential Florida lifestyle. Waterview’s galore as you walk into your newly completed, renovated Florida paradise home, on a deepwater marina and canal, which epitomizes beauty and style. Boat lovers will want the location of this totally turnkey furnished 1,423-square-foot standalone two-bedroom, two-bath home, with your upgraded composite boat dock just 15 feet behind your villa. Completely remodeled, this home provides contemporary classic design features that create an open airy gorgeous living space. All new stainless appliances in 2026, air-conditioner 2025, roof 2019 and more. The open kitchen design with a large island, new quartz countertops, plenty of beautiful new cabinets with roll-out drawers and a contrasting white and gray classic color scheme. Great counter space makes the kitchen ideal for entertaining and enjoying the coastal casual lifestyle. Beautiful porcelain tile flows throughout the home, providing continuity from room to room. An oversized skylight in the great room with retractable shade provides lots of extra natural brightness. The large primary bedroom is complete with a fully refashioned en-suite bath with gorgeous granite countertops and custom-tiled shower. A spacious walk-in closet provides plenty of room for your coastal style wardrobe. The second bath mimics the maintained class and elegance of this home with granite counters and tiled shower. The lanai has been transformed into extra living space with a cozy study and separate office nook. The study is an ideal spot to curl up with a book or just sit privately and watch the beautiful white pelicans float by with dolphins and manatees alongside. This flexplace can also house extra sleepover guests. The double lanai facing the water allows a panoramic view and full access to your large, elevated brick paver patio and dock from floor-to-ceiling, impact-grade patio doors. Go outside to a private oasis that overlooks the wide-open canal, marina and bay views. Sit, dine, entertain or sunbathe while you enjoy the abundant wildlife from the comfort of your patio paradise, or hop in your boat secured to your 5-by-25-foot dock and head out to one of the many Longboat Key restaurants. Some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico. Impact windows and new hurricane-rated doors throughout. The Spanish Main maintenance-free community has a wonderful neighborhood feel with heated pool, deeded beach access, a 40-foot slip marina with social events galore, making every day feel like a vacation as you lounge in the sun poolside and enjoy the sea The deeded beach access is ideal for those numerous beach days and magnificent sunsets. Pet-friendly, maintenance-free, and an active 55-plus community are added benefits for your enjoyment. Only a short drive to fantastic shops and restaurants, including Anna Maria Island, plus cultural events Sarasota and St. Armands Circle have to offer. This villa has been fully renovated in compliance with FEMA standards due to hurricane flooding in 2024.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Freiwald (941-256-6775)
703 SPANISH DR S, LONGBOAT KEY, FL 34228
$435,0007 Days on yellowkey MLS ID: A4693381
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1322 Built: 1971 Tax: $2,539 (2025)Community: Spanish Main Yacht Club CondoSpa: NoVilla
Middle School: W.D. Sugg Middle
Remarks: Go through this beautiful villa and experience all the details that have gone into the total remodel of this home, completed in 2026. The open kitchen with solid 42-inchwood cabinets, classic quartz countertops, all new stainless appliances, new lighting and an oversized island with plenty of sitting room, which leads you into the dining/living space. This design lends itself to cooking and conversation; great for entertaining! The elegant primary en suite, redesigned for total privacy, has a large study, flex room and is ideal for the days you need to work, read or have a workout area. The primary bath is enhanced with a large shower and beautiful tile work. Another closet that houses the in-unit laundry was created for ease and convenience not to mention an additional walk-in closet for additional storage. Porcelain tile flows throughout the villa. The guest bath and bedroom are separate from the primary master en-suite allowing for privacy and a sense of your space. An all-glass lanai leads onto the brick paver patio. The sliding door with motorized blinds allows plenty of light to come in but privacy when needed. A new PVC gate protects the common space shared by the adjoining villa. This area allows for private grilling and direct access into a storage room. Hurricane windows and doors complete this amazing villa! This home is attached to its sister villa 711 Spanish Dr South also for sale. Equally as beautiful. If purchased together, new owners could have two homes available for friends and family gatherings, with multigenerational potential. Imagine two full fabulous kitchens, four bedrooms, four baths and lots more space for sleeping. Many opportunities with this rare find. This vibrant 55-plus boating community of Spanish Main Yacht Club neighborhood is full of wonderful neighbors, heated swimming pool with fabulous water views, private deeded beach access to the gorgeous Longboat Key beaches and the warm Gulf waters. The desired deepwater marina that has holds up to 40-foot vessels with 40 slips available for lease also has electric and water for convenience. Slips available! Fishing, boating, kayaking, paddleboarding and more. Bonus of being a pet-friendly community. Close to St Armands Circle and downtown Sarasota makes this location ideal for shopping, dining, theater, botanical gardens, airport and more. All 212 units in the Spanish Main Yacht Club are under FEMA regulations, guidelines and stringent adherence to rebuild specifications. Call for details. All FEMA regulations completed, including inspections. Ready to enjoy your paradise. You can be under 55 to purchase.
711 SPANISH DR S, LONGBOAT KEY, FL 34228
$435,0007 Days on yellowkey MLS ID: A4693392
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1327 Built: 1970 Tax: $2,539 (2025)Community: Spanish Main Yacht Club CondoSpa: NoVilla
Remarks: Calling all boaters. If you have ever considered living on Longboat Key in sunny beautiful Florida, now is your chance! This amazing villa is available and ready for you to move to paradise! 711 Spanish Dr. S. is a 2 bedroom/2bath home that has been newly renovated in 2025/2026 and it is beautiful! Entering the home your eyes are immediately drawn upwards to the gorgeous open beam 10’-12’ ceiling over the kitchen and dining area. The kitchen is complete with all new wood cabinets, new stainless top of the line appliances, undermount sink, Quartz counter tops, and an oversized island with a dark blue base which brings in a beautiful pop of color. The open floor plan flows easily with luxury vinyl connecting all the rooms. The dining living combination is airy and bright. The primary bedroom is divided from the Florida room with textured glass pane sliding doors that allow the light in but keep the space quiet and private. Beautifully renovated primary bath is tastefully appointed. The guest bedroom and bath have been updated with the same quality and fine design as the entire villa. The large Florida room houses the stacked washer and dryer in their own space. A stylish glass back door leads to the brick patio perfect for your potted plants and just sitting and enjoying the perfect Florida weather. A newly installed PVC gate secures the common area shared by the adjoining villa. Perfect area for grilling, storage of bikes, beach chairs, paddle boards and more. There is also easy access to the unit's storage room. The adjoining sister villa 703 Spanish Drive South is also for sale. If purchased together, new owners could have two homes available for friends and family gatherings, with multigenerational potential. Imagine 2 fabulous full kitchens, 4 bedrooms, 4 baths and lots more space for sleeping. This is a must see! Make it your new home with all hurricane rated windows and doors, and so much more. This vibrant 55+ community of Spanish Main Yacht Club neighborhood is full of wonderful neighbors, and lots of amenities, shuffleboards, swimming pool, private deeded beach access to the gorgeous Longboat Key beaches and the warm Gulf waters. Fishing, boating and so much more. The expansive 40 slip Marina in the envy of all boaters as the lease is extremely inexpensive to lease, you won’t believe it. Call for details. Close to St Armands Circle and downtown Sarasota makes this location perfect for shopping, dining, theater, botanical gardens, airport and more. All 212 units in Spanish Main Yacht Club are under FEMA regulations, guidelines and stringent adherence to rebuild specifications. All FEMA regulations completed including inspections. Come and enjoy your soft place to land in this world.
4420 EXETER DR #303, LONGBOAT KEY, FL 34228
$599,000114 Days on yellowkey MLS ID: TB8455704
REDUCED by $26,000 (4.2%) on 05/13/2026
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)
4234 GULF OF MEXICO DR #G2, LONGBOAT KEY, FL 34228
$849,000367 Days on yellowkey MLS ID: A4653045
REDUCED by $46,000 (5.1%) on 04/21/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1636 Built: 1973 Tax: $13,273 (2024)Community: Pelican Harbour & Beach ClubCondo
Taxes:$13,273
Remarks: Motivated Seller—Priced to Sell! Enjoy sweeping Sarasota Bay views from this refreshed 3-bedroom, 2-bath end-unit condo in the highly sought-after Pelican Harbour & Beach Club on Longboat Key. This light-filled second-floor residence offers over 1,600 sq ft of coastal living with panoramic water views from the living room, primary suite, and private screened balcony. The spacious floor plan includes a bright living area, tranquil dining space, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent improvements include new carpet, recessed lighting, interior paint, mounted TVs, and a new AC (2025), water heater (2024) and roof (2023). Additional conveniences include in-unit laundry and covered parking and private Beach Access directly across the street. Pelican Harbour provides resort-style amenities: 200 ft of private deeded beach with new lounge chairs, heated pool and clubhouse, marina with boat slips (up to 28 ft) and kayak launch, plus tennis and pickleball courts. Pet-friendly community allowing up to two pets (dog/cat combinations permitted). Professionally managed with new roofs and hurricane-rated carports. Ideally located mid-key, just minutes to St. Armands Circle, Bayfront Park, and the new St. Regis Resort. Perfect as a full-time residence, seasonal retreat, or investment property—this bayside condo offers an unbeatable combination of location, amenities, and motivated-seller value.
Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)
Listing Agent: Shauna Ruby (941-544-2070)
4900 GULF OF MEXICO DR #203, LONGBOAT KEY, FL 34228
$689,000196 Days on yellowkey MLS ID: A4670932
REDUCED by $10,000 (1.4%) on 04/08/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1325 Built: 1975 Tax: $8,395 (2025)Community: Windward Bay AmdSpa: NoCondo
Taxes:$8,395
Remarks: IN THE COVETED "B" BUILDING, A STRATEGIC PRICE REFINEMENT NOW POSITIONS THIS EXCEPTIONAL RESIDENCE AS THE MOST COMPELLING OFFERING AT WINDWARD BAY! A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend. Wake up to spectacular sunrises over the sparkling bay and unwind with mesmerizing sunsets on the Gulf, directly across the street. Watch playful dolphins, jumping fish, gentle manatees, and vibrant Florida birdlife from your Florida Room or while preparing meals in your updated kitchen overlooking the shimmering waters. Your primary suite is a serene waterfront retreat, perfect for moonlit nights and sunrise mornings. Every detail of this condo has been thoughtfully designed to create a lifestyle of tranquility and relaxation, including remote controlled blinds in the Florida Room. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. The Windward Bay Association has been busy with a multitude of improvements and updates in the last few years including: Brand new roofs, resealing the buildings bayfront exteriors and painting of all the midrises in 2023/2024. Private roads were repaved and a new 1/2 mile long salt-tolerant privacy hedge was planted in October 2025. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced and 2026 Condo Fees only increased by $13 a month. This is more than a home—it’s a lifestyle. Experience the beauty, serenity, convenience, and the maintenance free life you’ve always dreamed of. GREAT NEWS, PAST CAPITAL IMPROVEMENT ASSESSMENTS WERE PAID IN FULL BY SELLER, NOT ADDED TO MONTHLY DUES! Schedule your private showing today and make paradise yours!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Debby Mccaig (941-544-1713)
836 EVERGREEN WAY, LONGBOAT KEY, FL 34228
$995,000159 Days on yellowkey MLS ID: A4674750
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2813 Built: 1991Monthly Fee: $1,644 Tax: $4,852 (2025)Community: Cedars East Sec 3Condo
Taxes:$4,852
Remarks: Introducing a Cedars East condominium unit offering the space and privacy of a single-family home with the ease of condo living. Elevated among the treetops on the Bay side of the island, the home enjoys partial Sarasota Bay views and exceptional access to Sarasota Bay waters perfect for launching a kayak, fishing, enjoying the tide pools. This premier tennis community home features 2 oversized garage spaces, wood floors throughout the first elevated floor, a bright, open great room with a large open kitchen for entertaining, with water views of Sarasota Bay, and inviting fireplace, screened decks for bay breezes, and an office/den. Upstairs is the primary bedroom with multiple walk-in closets, ensuite bathroom and screened porch where you can unwind and catch a glimpse of the sunset glow over the treetops. Two guest bedrooms share a full bathroom. Offered furnished. Cedars East is filled with amenities. From the clubhouse with a restaurant and Tiki Bar, pool, to walking trails through the mangroves, a kayak launch and a bayside community pier for gathering, fishing and enjoying the sunrise. A tennis club membership allows access to tennis and pickleball courts, tournaments, lessons and more. What are you waiting for? Make this your home or income opportunity today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Eileen Saunders (662-404-0816)
741 OLD COMPASS RD, LONGBOAT KEY, FL 34228
$1,895,00075 Days on yellowkey MLS ID: A4684578
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2173 Built: 1969Monthly Fee: $63 Tax: $11,776 (2024)Community: Emerald HarborSpa: YesSingle Family
Taxes:$11,776
Remarks: Exceptional opportunity to own a Longboat Key waterfront home in the highly desired community of Emerald Harbor. This 3BR/2BA, 1,926-sf canal front home with pool sits on an oversized 100x155-ft lot along one of Longboat’s widest canals (~110 ft) offering deep-water boating access just a half mile to the Intracoastal Waterway. Private beach access with parking is less than half a mile away. The property experienced storm-related water damage in 2024 and is ready for renovation or a brand-new custom home build. Enjoy island living close to The St. Regis Longboat Key Resort, The Resort at Longboat Key Club, St. Armands Circle, and North Longboat Village favorites—Shore, Mar Vista, Whitney’s, and Lazy Lobster. Emerald Harbor Longboat Key home for sale combines boating, beach access, and the ultimate Florida lifestyle—an unbeatable fixer-upper Longboat Key canal-front opportunity in one of the island’s premier neighborhoods.
Listing Agent: Steve Walter (941-809-0907)
5055 GULF OF MEXICO DR #331, LONGBOAT KEY, FL 34228
$895,000194 Days on yellowkey MLS ID: A4670624
1 Days Off yellowkey (back on 5/12/2026)
REDUCED by $90,000 (9.1%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $5,337 (2024)Community: Club LongboatSpa: YesCondo
Taxes:$5,337
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to your coastal retreat in paradise — a stunning third-floor waterfront residence in Club Longboat Beach and Tennis, offering expansive Gulf views and one of the largest floor plans in the community. This exceptional 2-bedroom plus 3rd bedroom/study layout perfectly blends elegance, comfort, and functionality, ideal for full-time living or as a refined vacation escape. With 750 feet of pristine Gulf frontage, this home immerses you in the beauty and serenity of coastal living. Beautiful engineered white oak wood floors flow throughout the open, sun-filled living space, which seamlessly extends to your private balcony’s, the perfect spot to enjoy the tranquil sound of the waves and stunning sunsets. The updated kitchen features stone countertops, white cabinetry, and has been opened up to create a larger, more connected floor plan ideal for entertaining. The primary suite is a private sanctuary, boasting a remodeled marble bath with high-end fixtures and a spa-like ambiance. The guest suite provides equal comfort and privacy, featuring a beautifully appointed travertine-floored bathroom. A custom wall of California closets offers exceptional storage and style. The Club Longboat Beach and Tennis community offers amazing amenities, including private beach access with lounge chairs and beach umbrellas, eight professional har-tru tennis courts, pickleball, fitness center, shuffleboard, barbeque area, clubhouse with regular social events, sauna, spa and two heated swimming pools. Club Longboat is a pet-friendly community allowing up to two pets with fees that include exterior maintenance and insurance, cable, water, sewer and trash. Perfect as a full-time residence or an income-producing rental, with one-month minimum leases permitted up to 12 times per year. Only a short drive to many fine restaurants, boutiques, Anna Maria Island, St. Armands Circle and the City of Sarasota. Sarasota is a well-known center for arts and culture including the Asolo Theater, Van Wezel Performing Arts Center and Ringling Museum. Schedule your showing today and make resort style living a reality.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Heers (941-726-1703)
604 SPANISH DR N, LONGBOAT KEY, FL 34228
$465,00058 Days on yellowkey MLS ID: A4687282
0 Days Off yellowkey (back on 5/11/2026)
REDUCED by $30,000 (6.1%) on 04/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1357 Built: 1967 Tax: $2,486 (2025)Community: Spanish Main Yacht Club CondoSpa: NoCondo
Taxes:$2,486
Remarks: Longboat Key waterfront lifestyle at its finest is now yours to discover. We are proud to present this stunning, fully renovated waterfront two-bedroom, two-bathroom freestanding villa-arguably a premier location within the Spanish Main Yacht Club. Situated in the middle of the north shore of serene Lake Spanish Main, it provides breathtaking views in every direction. The effortless waterfront views are the star of the show, especially enjoyed from your oversized paver patio-ideally designed for perfect island lounging-but also from nearly every room in the home. The waterfront backyard of this residence is framed by mature Black Olive trees that provide dappled shade while perfectly preserving the bright southern light and glistening water. This "center-of-everything" location is truly unbeatable, offering effortless access to your private deeded beach, the deep-water marina, the community pool, and boat slips. Modern Luxury Meets Coastal Comfort- Inside, a comprehensive renovation features custom tile flooring throughout, immediately setting an elevated, modern tone. The gourmet kitchen is an entertainer's dream, boasting custom cabinetry, designer stone countertops, and new stainless steel appliances centered around a first-class island with updated statement lighting. The open-concept floor plan flows seamlessly from the kitchen into an elegant dining area and a spacious family room, where natural light pours in alongside expansive lake views. Beyond, a sun-drenched Florida room?perfectly suited for an artist's studio and private office?offers southern-facing windows where you can watch the sunlight glisten off the water. Private Retreats-The primary suite is a sanctuary of its own, featuring a walk-in closet, generous proportions, Lake Views and a fully renovated ensuite bath. The guest wing is equally impressive, offering an ample bedroom and a stunningly renovated bathroom with a contemporary walk-in shower. Rounding out this exceptional property are the interior workshop, laundry room, additional storage, outdoor shower and a spacious carport perfectly sized for all your island toys. New Windows installed 2019, 2022 brought a new Roof and AC.
6810 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$2,250,000204 Days on yellowkey MLS ID: A4669890
1 Days Off yellowkey (back on 5/11/2026)
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2848 Built: 2024Monthly Fee: $83 Tax: $7,410 (2024)Community: LongbeachSpa: YesSingle Family
Taxes:$7,410
Remarks: Significant Price Reduction on this NEW in 2024, dream retreat that is uniquely positioned in the highly sought after “Village” of Longboat Key, a neighborhood known for its quaint charm and vibrant community atmosphere. Featuring 4 bedrooms and 4 and a half baths in open and light filled rooms, a backyard oasis with a pool and outdoor kitchen, high impact windows and doors throughout, 1230 sq ft of porches and balconies and an amazing rooftop top deck with spectacular water views: this is truly the epitome of luxury island living! The stunning chefs kitchen features high end appliances, including a 6 burner gas range, double ovens and a large center island. A perfect open flow into the inviting dining and living area, allows for exceptional entertaining with picturesque views out to the backyard oasis, seamlessly connecting indoor and outdoor spaces. This rare offering of NEW construction in this wonderful neighborhood is hard to come by. It affords its owner peace of mind, whether this is your forever home, your part time vacation retreat or a fabulous investment rental property. The community features multiple restaurants, a couple of Bayfront docks and even a community boat ramp. The gorgeous Gulf of Mexico is within a short walk, bike or golf cart ride away and is one of the nicest beaches on the island. It stretches for miles and is the perfect spot to spend the day before returning to watch the sunset from your rooftop deck. Come savoir the laid back island lifestyle that Longboat Key is known for and make this tranquil coastal retreat your own.
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
4310 FALMOUTH DR #304, LONGBOAT KEY, FL 34228
$360,000124 Days on yellowkey MLS ID: A4678473
REDUCED by $39,000 (9.8%) on 05/06/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969Monthly Fee: $1,196 Tax: $4,937 (2025)Community: Longboat HarbourCondo
Taxes:$4,937
Remarks: Unlock the Door to Your Dream Beach and Boating Lifestyle! Step into a world of unparalleled charm with this move-in ready, fully furnished gem on Longboat Key. This isn’t just a home; it’s a transformative lifestyle choice for those craving adventure, relaxation, and vibrant social connections. Picture yourself waking up to breathtaking bay views every morning from your stylish condo, featuring elegant granite countertops, state-of-the-art appliances, and a spa-like shower that redefines luxury. Your perfect beach days await with exclusive private beach access, complete with a dedicated beach house that offers showers and restrooms for your convenience. For boating enthusiasts, the Longboat Key Yacht Club provides convenient boat slips and kayaks, giving you immediate access to the pristine waters of the bay. Stay energized and engaged with an array of top-tier amenities, including tennis courts, shuffleboard, a rejuvenating sauna, and a fully equipped gym. Join a dynamic social scene filled with workshops, a cozy library, an inspiring art studio, and clay classes, plus the warm camaraderie of the Book Buddies club that fosters connections. With four inviting swimming pools, a grand banquet hall for gatherings, a fun game room for entertainment, and convenient private beach parking, every day feels like a luxurious getaway. This is more than just a condo; it’s a lifestyle experience you truly deserve. Don’t let this extraordinary Longboat Key oasis pass you by! Schedule your showing today and discover if it’s your perfect match!
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Rademacher (612-965-6188)
4500 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$739,00055 Days on yellowkey MLS ID: A4685838
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1975 Tax: $2,843 (2025)Community: Windward Bay AmdCondo
Taxes:$2,843
Remarks: GORGEOUS BAYFRONT PENTHOUSE VIEWS Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living. Schedule your private showing today.
Listing Agent: Marcela Terrell (941-929-3010)
6680 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$13,499,00097 Days on yellowkey MLS ID: A4682193
Bed: 6 Bath: 6.5 Gar: 6 Liv Area Sq Ft: 6408 Built: 2020 Tax: $22,777 (2025)Community: RauchSpa: YesSingle Family
Taxes:$22,777
Remarks: Welcome to a once-in-a-generation private waterfront family compound on the coveted north end of Longboat Key—an extraordinary 2.4 acre, fully gated coastal estate that blends architectural mastery, resort-level amenities, and rare development potential. Encompassing four buildable parcels (500, 510, 520 Nomas Way and 6680 Gulf of Mexico Drive), this legacy property offers unparalleled privacy, flexibility, and long-term value. From the moment you arrive, illuminated by classic Bevelo gas lanterns, the estate unfolds with intention and elegance. The custom-designed main residence is complemented by a separate 3-bedroom, 2-bath, 1,850-sq-ft guest home with a detached garage—perfect for extended family, guests, or staff accommodations. Every detail reflects thoughtful craftsmanship, from the 900-bottle red cedar wine cellar to the oversized custom wood-burning fireplace with gas option. Designed for both grand entertaining and everyday indulgence, the chef’s kitchen features natural gas cooking with Wolf and Sub-Zero appliances, while state-of-the-art home automation and whole-home sound elevate daily living. Step outside to a true private resort: a 15,000-gallon free-form pool with a 1,000-gallon spa, heating and chilling via reverse heat pump and natural gas, and an expansive custom tiki pavilion built for unforgettable gatherings. For boating enthusiasts, this estate is unmatched—165 feet of frontage on Bishops Bayou, two docks, three boat lifts, and deep-water, direct Intracoastal access. Across Gulf of Mexico Drive, deeded private beach access makes turquoise waters and nightly sunsets a daily ritual. Car collectors and hobbyists will appreciate six garages, including an automotive lift, plus a 50’ x 24’ covered pole barn for additional storage. Peace of mind is absolute with a 24-camera security system, safe room, elevator, and a 60kW natural gas generator powering the entire estate during any weather event. Fully fenced and gated, this property offers complete privacy without compromise. This is more than a home—it is a coastal masterpiece, a designer’s dream that exudes sophistication, balance, and harmony. An irreplaceable opportunity to own one of Longboat Key’s most remarkable waterfront estates, where luxury, security, and lifestyle converge in perfect alignment.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Lee Brewer (941-724-3448)
5920 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$1,749,500371 Days on yellowkey MLS ID: A4652254
Bed: 2 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2823 Built: 1973 Tax: $8,478 (2024)Community: Longboat KeySpa: YesSingle Family
Taxes:$8,478
Remarks: DEEDED BEACH ACCESS AND DEEP WATER CANAL at this beautifully renovated mid-key beach house on the barrier island of Longboat Key. You can enjoy a 3-minute walk to the beach using your private beach access or step outside and enjoy the canal on your trex dock. The uncrowded beach with natural surroundings, fine sand beaches, warm breezes, and clear turquoise waters is truly a special place. Entering the home, you are greeted by terrazzo floors, stunning 2 story foyer and a water view of the canal. All new wood kitchen cabinets including island and coffee bar with quartz countertops making this a great area to entertain guests. All 3 bathrooms have been completely renovated and include custom tile showers. Large master bedroom with en-suite bathroom. An enclosed lanai overlooking the canal is a perfect spot for an office or tropical retreat. Large living room with wood burning fireplace and new tile flooring provides a relaxing space. New kitchen and bath fixtures throughout. Ceiling fans in each room. Being in the middle of LBK provides easy access to Anna Maria Island and Bradenton to the north, St. Armands and Sarasota to the south. SRQ airport is less than 45 minutes. Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway, deeded beach and canal access with 5924 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together (or use one as a rental for an ongoing revenue stream}. The property is being sold as-is. Please use AS IS Residential Contract for Sale and Purchase_FloridaRealtors-FloridaBar-ASIS-7.xdp
Listing is courtesy of: JOHN DONATO REAL ESTATE INC (941-504-4987)
Listing Agent: John Donato (941-504-4987)
5924 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$849,500371 Days on yellowkey MLS ID: A4651805
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1359 Built: 1955 Tax: $11,764 (2024)Community: Fractional SubSingle Family
Taxes:$11,764
Remarks: Sought after mid-key cottage home with DEEDED BEACH ACCESS on the barrier island of Longboat Key. Entering the home, you are greeted by terrazzo floors, wood beam ceilings and a tile accented gas fireplace in the large living room. An additional room overlooking screened in pool can be used as an office, exercise room or extra space for guests. Newly renovated kitchen with wood cabinets, quartz countertops, new sink and fixtures. Bathrooms have been completely renovated with beautiful walk-in tiled showers. A built-in bookcase in the living room adds charm with plantation shutters, accent lighting and ceiling fans throughout. Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway and deeded beach access with 5920 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together. Another possibility is to use one as as a rental for an ongoing revenue stream. The property is being sold As-Is (use FAR-BAR-ASIS-7.
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