Location: Longboat Key
Keyword(s): Martha B. King Middle
Keyword(s) Middle School: Martha B. King Middle
Do Not Show Listings
624 SAINT JUDES DR, LONGBOAT KEY, FL 34228
$749,900202 Days on yellowkey MLS ID: A4672840
REDUCED by $15,000 (2.0%) on 04/20/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1387 Built: 1957 Tax: $8,692 (2025)Community: Longboat KeySingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,692
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Wow, Excellent New Price! Your opportunity to own a piece of Longboat Key paradise just got even better. The stunning Cali-Modern residence has a new, more attractive price! Presenting an amazing opportunity for this stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. Presenting a stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. This sophisticated, move-in ready home offers an abundance of good vibes and professional quality, available now on the highly sought-after North End of exclusive Longboat Key. Sleek, chic, and absolutely move-in ready, this property is an instant atmosphere setter. From the moment you step inside, you'll feel the coastal modern bliss. Enjoy the clean, modern lines, vaulted ceilings, and stunning stone tile floors, all bathed in gorgeous southern sun light. The upgraded kitchen and bathrooms sparkle with new features, complemented by new appliances. This home has been lovingly and extensively renovated, offering quality and style that goes well beyond the expected. You will find thoughtful design and premium features in every corner. Step outside to your own private backyard oasis, the perfect spot to sip a sunset cocktail. Fully fenced and private this oasis sets up perfectly for the future pool. And talk about location! You are literally steps from both Gulf and Bay access. This home boasts unbeatable walkability to island favorites like Harry's Deli and The Continental Kitchen, Euphymya Haye and the Hayloft, Lo-Key Island Grille, Cedars East Tennis and Fitness Resort and many others. The best-kept secret? A private back gate leads you directly into the 32 acres of Joan Durante Park, offering pure, natural Florida coastal hammock. This park is a true gem filled with nature walking trails, fishing piers, playground for the kids and multiple Bay access points (perfect for the kayak launch) No fuss, no stress. With a standing seam metal roof, Hardi board siding, newer double-pane windows, New interior, new appliances and offered fully furnished, this charmer is ready for your island life to begin immediately. Don't wait, come feel the charm for yourself!
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
4960 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228
$649,900139 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 is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Debby Mccaig (941-544-1713)
4325 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228
$1,100,00026 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)
4234 GULF OF MEXICO DR #G2, LONGBOAT KEY, FL 34228
$849,000388 Days on yellowkey MLS ID: A4653045
0 Days Off yellowkey (back on 5/24/2026)
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
Tax Year: 2024
Remarks: Under contract-accepting backup offers. 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)
6700 GULF OF MEXICO DR #117, LONGBOAT KEY, FL 34228
$550,00057 Days on yellowkey MLS ID: A4687787
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1969 Tax: $2,348 (2025)Community: Whitney BeachSpa: NoCondo
Taxes:$2,348
Remarks: Welcome to 6700 Gulf of Mexico Drive #117, a beautifully reimagined end-unit 2-bedroom, 2 full bath residence in the sought-after Whitney Beach community on Longboat Key. Taken down to the studs and completely renovated, this waterfront condominium offers coastal living with sweeping views of Bishop’s Bayou, abundant natural light, and exceptional privacy. A private front courtyard welcomes you inside, where new high-end luxury vinyl plank flooring flows throughout, and a bright, open layout immediately draws your eye to the water. As an end unit, additional windows enhance the airy feel, while hurricane-impact windows and sliding doors frame tranquil bayou views. From the main living space—and even from the primary bedroom upon waking—you’ll enjoy peaceful scenes of dolphins, manatees, and glowing sunsets reflecting across the water. The fully redesigned kitchen is both stylish and functional, featuring granite countertops, soft-close cabinetry, custom glass-front accents, classic subway tile backsplash, designer pendant lighting, peninsula seating for four, and a full suite of GE stainless steel appliances—all positioned to capture the water views. Both bathrooms have been completely renovated with glass walk-in showers, elegant tilework, and quartz-topped vanities, offering a clean, modern aesthetic. A new Whirlpool stackable washer and dryer adds everyday convenience. Whitney Beach is a unique beach-to-bay community with deeded private access to the Gulf just across the street. Residents enjoy resort-style amenities including pools, tennis courts, shuffleboard, barbecue areas, kayak storage and launch, walking paths, and a tranquil bayfront pavilion. Boat slips are available when offered, and the community pier provides a charming setting for fishing or relaxing by the water. Ideally located on the north end of Longboat Key, this residence offers easy access to Anna Maria Island, as well as the dining, shopping, and cultural attractions of Sarasota. Whether as a full-time home, seasonal retreat, or investment, this is an exceptional opportunity to enjoy the best of bay-to-beach living. Professional photos coming soon.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kelly Sallee (941-914-0400)
4900 GULF OF MEXICO DR #203, LONGBOAT KEY, FL 34228
$689,000217 Days on yellowkey MLS ID: A4670932
0 Days Off yellowkey (back on 5/23/2026)
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: Under contract-accepting backup offers. 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!
5231 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$545,000159 Days on yellowkey MLS ID: A4676730
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 720 Built: 1973 Tax: $6,784 (2024)Community: Covert IiCondo
Taxes:$6,784
Remarks: Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
4825 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$799,000252 Days on yellowkey MLS ID: A4667044
REDUCED by $40,900 (4.9%) on 05/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $11,897 (2024)Community: Westchester AptsSpa: NoCondo
Taxes:$11,897
Remarks: Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full.
6001 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$9,995,000245 Days on yellowkey MLS ID: A4667111
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 6959 Built: 2013 Tax: $105,194 (2024)Community: Longboat KeySpa: YesSingle Family
Taxes:$105,194
Remarks: A Gulf-Front Masterpiece on Longboat Key! This stunning Gulf-front estate is perfectly placed on nearly an acre of pristine Gulf-front property along the shoreline on Longboat Key. With direct Gulf frontage, this architectural masterpiece offers more than 6,900 square feet of refined interiors and panoramic views that stretch endlessly across the Gulf of Mexico. Designed for both privacy and grand-scale entertaining, the residence balances timeless craftsmanship with recent enhancements including a 2025 primary bath remodel, newer French doors, and resort-style pool and spa with natural gas heating and fire pit. From the moment you arrive through the circular drive, the home’s elegant façade, manicured landscaping, and elevated design make a commanding first impression. Inside, expansive living areas are defined by travertine and hardwood flooring, soaring coffered ceilings, crown molding, and walls of glass framing breathtaking views. The open floor plan flows effortlessly from the formal living and dining rooms to the family room and gourmet kitchen, designed for effortless entertaining. The chef’s kitchen showcases custom wood cabinetry, granite counters, a large island, high-end appliances, double ovens, and a breakfast nook overlooking the Gulf. The main-floor primary suite offers a serene retreat with direct beach views, its own private terrace, dual walk-in closets, and a spa-like new bath featuring dual vanities, stone counters, and a freestanding soaking tub. A private elevator connects all levels, including a versatile second-story loft, media room, and four additional bedrooms (some en-suite) providing ample comfort for family and guests. The outdoor living space defines Florida luxury—complete with an expansive travertine deck, heated pool and spa, summer kitchen, and multiple covered terraces designed for dining and relaxation. Enjoy vibrant sunsets over the Gulf from nearly every vantage point. The property also features new hurricane-rated French doors, a whole-house generator with raised platform, and a three-car side-entry garage with guest parking. Located on the prestigious north end of Longboat Key, this gated estate offers the perfect balance of seclusion and accessibility. Stroll along miles of private beach or take a short drive to the Longboat Key Club, offering championship golf, tennis, and fine dining. Just minutes away, St. Armands Circle and downtown Sarasota offer a vibrant mix of boutique shopping, art galleries, and acclaimed restaurants. With world-class marinas, cultural landmarks, and pristine beaches within reach, this exceptional residence captures the very best of Sarasota’s luxury coastal lifestyle. Offering an unparalleled combination of design, craftsmanship, and Gulf-front serenity, 6001 Gulf of Mexico Drive stands as a statement of timeless coastal elegance—where every sunset feels like home.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
900 SPANISH DR N, LONGBOAT KEY, FL 34228
$750,00049 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 Agent: Kimberly Freiwald (941-256-6775)
615 DREAM ISLAND PL #210, LONGBOAT KEY, FL 34228
$949,90040 Days on yellowkey MLS ID: TB8503989
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1509 Built: 1985 Tax: $11,560 (2024)Community: Harbour Villa Club At The BuccaneerSpa: YesCondo
Taxes:$11,560
Remarks: Paradise at Harbour Villa Club – Waterfront Luxury with a boat slip on Longboat Key! Enjoy this condo year round, or rent it weekly when you cannot be there- you choose! Discover this fully renovated 2BR/2BA condo with panoramic views of the gorgeous Sarasota Bay. Bright and spacious, the open floor plan features soaring 9 ft ceilings, custom finishes, a gourmet kitchen with top-of-the-line appliances and a sleek wet bar. The primary suite offers stunning water views, dual closets, and a spa-inspired bath. The second bedroom is spacious and set apart from the primary. Step into the enclosed lanai for breathtaking 180° water views and added living space— perfect for relaxing or entertaining. This unit comes with a deeded 40' boat slip #3 which features upgraded power and plumbing, new wraps, caps, marine grade bumpers and a deck box- a rare bonus that can accommodate a 55' vessel! Harbour Villa Club is nestled in a quiet corner and you can walk or bike to the beach, area restaurants, and beloved Harry's Corner Store. This is a pet friendly community with covered parking, storage, elevators, kayak and bike storage, private dock, heated pool, tennis/pickleball courts, grills and beautiful landscaping. Weekly rentals allowed. Call today!
Listing is courtesy of: CENTURY 21 BILL NYE REALTY (813-782-5506)
Listing Agent: Lori Lahart (813-297-9610)
6680 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$13,499,000118 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)
836 EVERGREEN WAY, LONGBOAT KEY, FL 34228
$995,000180 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: Bay Views! Investor Dream Home! A double condo unit which feels like a single-family home, because it is not attached to anything but sunshine, the bay and dreams! Elevated among the treetops on the bay side of Longboat Key, it features 2 oversized garage spaces, wood floors throughout the first elevated living level, an open great room with a large open kitchen for entertaining, an inviting wood-burning fireplace, screened lanai for bay breezes and a office/den/flex room. Upstairs you will find 2 guest bedrooms which share a full bath and a primary bedroom with a view of Sarasota Bay through a wall of windows and a screened lanai where you can catch the sunset glow over the treetops. The ensuite primary bath features dual sinks and 2 large walk-in closets. Amenities in the premier tennis community include exceptional access to Bay waters, perfect for launching a kayak, fishing and enjoying the tide pools. Enjoy a boardwalk stroll through mangroves and watch the sunrise from a private bayside dock (no boat access). Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate. Update, redesign and make it your home or income opportunity today!
Listing Agent: Eileen Saunders (662-404-0816)
771 MARBURY LN, LONGBOAT KEY, FL 34228
$2,500,00085 Days on yellowkey MLS ID: A4686401
Bed: 5 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 3016 Built: 1985 Tax: $24,092 (2025)Community: Sleepy Lagoon Park 2Single Family
Taxes:$24,092
Remarks: One or more photo(s) has been virtually staged. Boaters will love this spacious elevated home in a premier waterfront location on Longboat Key with dock, lift and by boat it is just four homes from the intercoastal, open bay waters and a short boat ride to the Gulf. Built for large gatherings, this home is beautifully designed with loads of gathering and entertaining spaces. The open plan home was thoughtfully designed with five bedrooms, four with en-suite baths. The kitchen features custom wood cabinets and granite countertops. Entertaining will be a breeze with two large gathering spaces, including a great room with dining area and adjacent bonus room that would be a wonderful media or game room. Ground level highlights include two bonus areas and a huge four-car garage. The composite dock has a 10,000-pound boat lift, water and electric. Recent updates include hurricane windows and doors (2025), metal roof (2025), pool equipment and pool heater (2025) and interior freshly painted. This location on Longboat Key can't be beat with community beach access just across the street, and a heated pool and boating in your own backyard. This is the ideal home to create wonderful island memories.
Listing Agent: Holly Switow (941-735-3186)
667 EL CENTRO, LONGBOAT KEY, FL 34228
$380,000274 Days on yellowkey MLS ID: A4664572
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1327 Built: 1969Monthly Fee: $1,340 Tax: $6,206 (2024)Community: Spanish Main Yacht Club CondoVilla
Taxes:$6,206
Remarks: New photos coming on this beautifully updated free-standing villa in Spanish Main Yacht Club on Longboat Key, a warm and vital boating community with private beach access, pool, clubhouse and boat slips. The community is undergoing a renaissance of sorts as many units (including this one) did have water intrusion in the summer storms of 2024. This owner contracted with the community contractor. has paid related assessment and work is nearly completed! This unit has a bright open floor plan and hurricane windows. Main living area has tile flooring and both bedrooms will have new carpet. There are two bonus areas, one is adjacent to the primary bedroom and could be a private reading area or office and the other adjoins the great room. Once completed, this unit will have two new baths, new appliances, kitchen updated, new doors and new paint throughout. This villa is on the corner and has a much-desired additional parking pad, giving as many as four parking spaces depending on car size. The laundry room, typical of Florida, is in a separate room under the carport. Longboat Key is paradise. A barrier island off Sarasota, where you can find wonderful restaurants, community tennis facilities, parks, bike lanes and a short drive to Sarasota and Anna Maria Island.
765 SAINT JUDES DR N, LONGBOAT KEY, FL 34228
$1,499,900110 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
Taxes:$14,125
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
$725,000119 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.
718 SPANISH DR N, LONGBOAT KEY, FL 34228
$435,00075 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)
5055 GULF OF MEXICO DR #331, LONGBOAT KEY, FL 34228
$895,000215 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 Agent: Ryan Heers (941-726-1703)
604 SPANISH DR N, LONGBOAT KEY, FL 34228
$465,00079 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.
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