Location: Longboat Key , 34228
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669 SPANISH DR N #21, LONGBOAT KEY, FL 34228
$339,000321 Days on yellowkey MLS ID: A4653816
0 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1087 Built: 1969 Tax: $5,733 (2024)Community: Spanish Main Yacht Club CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,733
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Priced to sell - Fully renovated villa ready for immediate occupancy! Welcome to Spanish Main Yacht Club, a sought-after 55+ waterfront community on Longboat Key, where coastal living meets exceptional value. This 2-bedroom, 2-bath villa-style condo offers 1700 SqFt of interior living space, 1087 of it under air, with endless potential to make it your dream home. This stand-alone condo has undergone FEMA-approved storm mitigation and a full rebuild. Bring your vision and decorate to suit your personal style—below market value! Step inside to find a spacious open-concept living and dining area, perfect for entertaining. The adjoining Florida room offers additional flexible space, bathed in natural light—ideal for morning coffee or quiet evenings. The primary suite features an en-suite bathroom, closet and indoor laundry room. Enjoy private beach access just steps away, or take advantage of the community marina with first-come, first-served boat slips, kayak racks, and direct access to Sarasota Bay. Amenities include a heated outdoor pool, shuffleboard courts, a clubhouse with game room, library, and frequent community events. This pet-friendly community offers covered carport parking, guest spaces, and maintenance-free living, all set within beautifully maintained, palm-lined grounds. Just minutes from St. Armand’s Circle and Anna Maria Island, this location offers world-class shopping, dining, and entertainment, plus access to some of Florida’s finest white sand beaches. Whether you're looking for an investment, full-time residence or a vacation getaway, this villa offers endless potential in one of Longboat Key’s most desirable communities. Seller says bring offers—don’t miss your chance to own a piece of paradise!
Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)
Listing Agent: Geoff Scalera (941-321-4158)
1065 GULF OF MEXICO DR #302, LONGBOAT KEY, FL 34228
$619,000571 Days on yellowkey MLS ID: A4624142
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981 Tax: $4,571 (2023)Community: Beachplace IiiCondo
Taxes:$4,571
Tax Year: 2023
Remarks: One of a kind, never rented, ready for a new owner to put their touches on this opportunity! Unit has endless views. Come look, Being able to rent this unit, by the month, twelve times a year, that offers our beautiful GULF BEACH within seconds of the front door is incredible! Our third floor views are breathtaking, yet fully protected from the elements. Our Building is quiet, but close to BEACHPLACE amenities! Owners are motivated to sell and we can give you a complete tour when you visit. Also new HURRICANE Windows recently added. BONUS TWO PARKING SPACES, ONE IN GARAGE,ONE OUTSIDE! BEST VALUE IN BEACHPLACE BY FAR> GO COMPARE!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: James Weingart (440-623-9068)
1105 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228
$999,99968 Days on yellowkey MLS ID: A4680369
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1172 Built: 1981Monthly Fee: $1,600 Tax: $8,733 (2025)Community: Beachplace IiCondo
Taxes:$8,733
Tax Year: 2025
Remarks: Direct Ocean view from this Bright Airy corner unit in desirable building five. Catch the view of the Gulf of Mexico and Sunsets from your balcony. To see this property is to fall in love with easy living! You need to visit this unit to get a sense of the remarkable views , especially the amount of light that permeates the entire interior. Beachplace is a perfect get away on the south end of Longboat Key, and comprise many amenities. Pickle Ball, Tennis, two exercise facilities, Olympic pool, with designated lap lanes, over size hot tub , covered baby pool . Electric car chargers, gas grill
225 SANDS POINT RD #7101, LONGBOAT KEY, FL 34228
$699,00085 Days on yellowkey MLS ID: A4678918
3 Days Off yellowkey (back on 3/30/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1983 Tax: $7,270 (2025)Community: Inn On The Beach Ph IiiCondo
Taxes:$7,270
Remarks: Under contract-accepting backup offers. Enjoy peaceful lagoon views from this completely remodeled Junior Suite. Sold turnkey furnished and currently in the hotel program, the Junior Suites in this building have 10’ ceilings unlike the other buildings. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace. As an owner in the hotel program you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship Golf, the award-winning Tennis Gardens, spa, fitness center, white sand beach with umbrellas & waitstaff, and a full service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying your Longboat Life today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
4825 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$839,900195 Days on yellowkey MLS ID: A4667044
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $11,897 (2024)Community: Westchester AptsCondo
Taxes:$11,897
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
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.
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
225 SANDS POINT RD #6103, LONGBOAT KEY, FL 34228
$569,000278 Days on yellowkey MLS ID: A4658152
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1983 Tax: $6,997 (2025)Community: Inn On The Beach Ph IiiCondo
Taxes:$6,997
Remarks: Ideal for area residents needing space for overflow guests, or for out-of-state owners who want unlimited use with the ability to still earn income! The most perfectly peaceful lagoon views are enjoyed from this first floor Junior Suite in Building 6. Unlike the other buildings, this building boasts 10' ceilings making it feel especially spacious while optimizing natural light and view. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace overlooking the turquoise lagoon water. Building 6 offers extra privacy as it is located across the street from the main entrance, but still close enough to enjoy the pool and beach without having to pack the car and drive anywhere. Updates to the residence include new washer/dryer, new dishwasher, new microwave, new glass shower doors, new commode, new closet shelving, and new fire alarm. This unit is not part of the hotel program; however, it can be rented out by the owner or a 3rd party vendor on a nightly basis. Owners can also become members of the Longboat Key Club to partake in the numerous Resort amenities (Golf, Tennis, Restaurants, Fitness Center, Marina) if they still want to enjoy the benefits of owning in a Resort community without being part of the hotel program.
701 SAINT JUDES DR S #3, LONGBOAT KEY, FL 34228
$259,000104 Days on yellowkey MLS ID: O6370226
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1966 Tax: $3,873 (2024)Community: Saint Judes AptsCondo
Taxes:$3,873
Remarks: DIRECT WATERFRONT OPPORTUNITY IN LONGBOAT KEY! Here's your rare chance to own a waterfront property with direct access to the Intercoastal Waterway! Perfectly located for vacation rentals, this canal-front 1-bedroom, 1-bathroom end unit offers incredible potential for income, especially with high demand bookings from January to April. This property boasts 21 feet of water frontage and a newly installed seawall (June 2021). Enjoy the Florida lifestyle with easy access to boating, kayaking, and fishing. Additional outdoor amenities include a paver patio. Just steps away from a private beach access, kayak launch, and deeded beach entry. The property also has direct access to the scenic Joan M. Durante Park, with 32 acres of walking trails, gardens, recreational areas, and breathtaking Sarasota Bay views. Take a short walk to top-rated restaurants, shops, a deli, bike and kayak rentals, and more. Plus, you're just a short drive to St. Armands Circle and Anna Maria Island! This is the most economical waterfront property you'll find in all of Longboat Key!
Listing is courtesy of: NIZZ REALTY INC (954-526-5105)
Listing Agent: Filitsa Sterner Mistretta (941-928-3666)
2450 HARBOURSIDE DR #234, LONGBOAT KEY, FL 34228
$2,000,00060 Days on yellowkey MLS ID: A4682324
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3383 Built: 1990Monthly Fee: $153 Tax: $11,852 (2025)Community: Marina BayCondo
Taxes:$11,852
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Welcome to Marina Bay, one of the most coveted condominium residences within the guard-gated Bay Isles community on Longboat Key. This expansive three-bedroom, three-bath residence offers 3,383 square feet of light-filled living space and exceptional privacy, sharing the floor with only one other residence. Enjoy sweeping panoramic views of Sarasota Bay and downtown Sarasota from the oversized screened balcony—an ideal setting for morning coffee, evening relaxation, and watching the abundant birdlife and marine activity. A second west-facing balcony captures spectacular Gulf sunsets, offering the best of both sunrise and sunset living. Marina Bay delivers a true resort-style lifestyle, featuring a large heated pool, tennis courts, pickleball courts, and a fitness center. Take leisurely strolls along the neighboring marina or around the picturesque Longboat Key Club Harbourside Golf Course. Ideally located, this residence is just a half-mile walk to Publix, CVS, and local shops, and only one mile from the new St. Regis Longboat Key Resort. Membership to the Longboat Key Club is available separately, providing access to world-class golf, dining, tennis, pickleball, and beach amenities. Whether as a full-time residence or an exceptional vacation retreat, this is a rare opportunity to enjoy luxury, convenience, and resort living on Longboat Key—truly, the best of island life.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Beverly St Hilaire (818-416-2505)
5270 GULF OF MEXICO DR #508, LONGBOAT KEY, FL 34228
$774,900134 Days on yellowkey MLS ID: A4673695
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1460 Built: 1974 Tax: $4,861 (2025)Community: The Banyan Bay ClubCondo
Taxes:$4,861
Remarks: Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Beth Ann Boyer (941-780-6606)
771 MARBURY LN, LONGBOAT KEY, FL 34228
$2,500,00028 Days on yellowkey MLS ID: A4686401
Bed: 5 Bath: 4.0 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 is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Holly Switow (941-735-3186)
3530 MISTLETOE LN, LONGBOAT KEY, FL 34228
$2,695,00071 Days on yellowkey MLS ID: A4680887
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3102 Built: 1991Monthly Fee: $1,083 Tax: $20,603 (2025)Community: Coreys LandingSingle Family
Taxes:$20,603
Remarks: Located behind the gates of Corey’s Landing in the sought-after Bay Isles community, this direct bayfront residence offers an exceptional Longboat Key lifestyle defined by boating, waterfront views, and deeded access to a private Gulf beach. With its private dock and 14,000-lb boat lift, the property provides immediate access to Sarasota Bay for boating, paddleboarding, and sunset cruising, while the Bay Isles Beach Club offers owners exclusive Gulf frontage, beach pavilions, and convenient access to Longboat Key’s pristine shoreline. Spanning 3,102 square feet across two levels, the four-bedroom residence is thoughtfully designed to capture natural light and water views while creating seamless indoor-outdoor living. The main living level is anchored by a dramatic bayfront living room with soaring cathedral ceilings, a gas fireplace, and walls of impact-rated glass sliders that open to a screened waterfront patio overlooking the bay. Adjacent to the living space, the formal dining room enjoys its own water views and flows easily into the fully renovated kitchen completed in 2022. Designed for both everyday living and entertaining, the kitchen features Bosch stainless appliances, quartzite countertops, custom cabinetry, pantry storage, and a breakfast bar for casual dining. The primary suite is conveniently located on the first floor, offering a spacious walk-in closet plus two additional closets and a private en-suite bath. Two additional guest bedrooms on this level—one currently used as a study—share a beautifully updated full bathroom. Upstairs, guests enjoy a private retreat with a loft-style bonus area featuring a built-in entertainment center and an oversized en-suite bedroom finished with elegant tilework. Extensive upgrades enhance comfort and long-term value, including a new tile roof (2023), two A/C systems (2022), updated dock with 14,000-lb boat lift, remodeled kitchen and baths, recessed lighting, storm windows on the bayside, a new electrical panel, exterior lighting, updated landscaping, sprinkler system, and a new screen enclosure. Corey’s Landing offers a maintenance-free waterfront lifestyle with 24-hour guard-gated security, community tennis courts, and a heated pool and spa. Ownership also includes deeded access to the private Bay Isles Beach Club, where residents enjoy Gulf-front relaxation with pavilion seating, beachside gatherings, and direct access to the white sands of Longboat Key. Ideally positioned behind the gates of Bay Isles, this residence is moments from the Longboat Key Club’s championship golf and tennis facilities, nearby marinas, and island dining. St. Armands Circle, Lido Beach, and downtown Sarasota’s renowned cultural venues, galleries, waterfront parks, and restaurants are all within easy reach—bringing together boating, beach access, and the best of Sarasota’s coastal lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
2110 HARBOURSIDE DR #526, LONGBOAT KEY, FL 34228
$700,000173 Days on yellowkey MLS ID: A4669215
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2031 Built: 1988 Tax: $9,842 (2024)Community: Fairway Bay 3Condo
Taxes:$9,842
Remarks: Carefree living awaits you with beautiful panoramic views of Sarasota Bay in this beautiful condominium at The Atrium on Longboat Key inside Bay Isles. Enjoy all that Florida living has to offer! The large kitchen is open to the dining/living rooms that overlook the gorgeous Bay. You can enjoy beautiful sunrises or evening gatherings from inside your unit or on your spacious private balcony. There are 2 bedrooms plus a den that's being used as a bedroom (closet can easily be added). Set "behind the gates" of Bay Isles, the Atrium offers residents a laidback, amenity-rich way of life featuring 24 hour gated security, under building-parking, a spacious storage room, walking pathways, kayak launch, heated community pool, fitness center/exercise room, tennis/pickleball courts, recently updated clubhouse, community BBQs, even added new 2EV charging stations. An extra bonus with this condo is you will receive a highly sought after beach access membership to the Bay Isles Beach Club which is across the street. To get to the beach there is even an underground tunnel for easy access so no waiting to cross the road. Newer AC (2018). This beach club provides a stress-free beach life with easy parking, storage lockers for beach chairs, ice machine, refrigerator as well as recently updated spa-like bathrooms making it convenient for residents to sit back, relax and enjoy beach life. Longboat Key Golf & Tennis Country Club memberships and deep water slips are available. Only a short distance to Publix with easy quick access that's walkable from the back road of Bay Isles. The Atrium with only 40 units has a charming quaint peaceful feel throughout. Furniture in unit does stay.
Listing is courtesy of: RE/MAX PALM (941-929-9090)
Listing Agent: Jessica Bow (941-356-2585)
4234 GULF OF MEXICO DR #G2, LONGBOAT KEY, FL 34228
$895,000331 Days on yellowkey MLS ID: A4653045
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: Price Improvement! Priced to sell! Waterfront 3BR Coastal Condo with Panoramic Bay Views! Experience the pinnacle of island living in this recently refreshed 3-bedroom, 2-bath condo in the highly desirable Pelican Harbour & Beach Club on Longboat Key. Located on the second floor, this light-filled end unit offers sweeping Sarasota Bay views from the living room, primary suite, and your private screened-in balcony—ideal for morning coffee or sunset cocktails. With over 1,600 sq ft of coastal-inspired living space, this residence features a spacious living room, tranquil dining area, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent updates include new carpet, furniture, recessed lighting, professionally painted interiors, mounted TVs, and a new AC and water heater (2024). Additional conveniences include in-unit laundry and covered parking. Pelican Harbour offers resort-style amenities: 200 feet of private deeded beach with new lounge chairs, Heated pool & clubhouse, Marina with boat slips (up to 28 ft) & kayak launch, Tennis & pickleball courts! Pet Friendly policy-An owner may have one dog or two house cats, or one dog and one house cat, but not more than two pets. Pets are defined as birds, fish, cats, dogs that may be kept in an owner’s unit: Dogs must be on a leash at all times when outside the confines of their owner’s apartment. Professionally managed, the community features new roofs, hurricane-rated carports. Ideally located mid-key, you're just minutes from St. Armands Circle, Bayfront Park, and the new St. Regis Resort. Whether you're seeking a full-time residence, seasonal escape, or investment opportunity, this bayside retreat offers the perfect blend of luxury, comfort, and convenience.
Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)
Listing Agent: Shauna Ruby (941-544-2070)
6810 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$2,250,000168 Days on yellowkey MLS ID: A4669890
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 2848 Built: 2024Monthly Fee: $83 Tax: $7,410 (2024)Community: LongbeachSingle 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.
7147 LA LENAIRE DR, LONGBOAT KEY, FL 34228
$5,235,000147 Days on yellowkey MLS ID: TB8448347
Bed: 5 Bath: 5.5 Liv Area Sq Ft: 3503 Built: 1990Monthly Fee: $283 Tax: $33,963 (2023)Community: Jewfish KeySingle Family
Taxes:$33,963
Middle School: W.D. Sugg Middle
Remarks: A rare offering on Florida’s coveted west coast, this private island sanctuary feels worlds away yet remains moments from the region’s most beloved coastal destinations. Set on the exclusive 38-acre island of Jewfish Key (accessible only by boat), this remarkable 1.35-acre estate commands its own secluded shoreline and uninterrupted views of crystal clear waters. Inspired by Polynesian architecture and designed to dissolve the boundaries between indoors and out, this estate home unfolds through airy pavilions connected by elevated walkways. Towering palms and lush tropical landscaping envelop the home, while its 18-foot elevation ensures both peace of mind and panoramic, horizon-level vistas. Inside, the freshly reimagined kitchen serves as the gathering heart of the home, with sleek quartz countertops, modern cabinetry, and a spacious oversized island that effortlessly bridges culinary function and relaxed entertaining. Expansive sliding glass doors draw natural light into the living space and frame sweeping views of the sandbar and bay, perfect for sunset watching. The main residence includes four bedrooms and four-and-a-half baths, plus a separate guest suite offering an additional bedroom, kitchen, and full bath, ideal for hosting with comfort and privacy. The primary suite is where the pace of the island truly settles in. Wake up to wide-open bay views, linger with coffee in the sitting area, or enjoy a glass of wine as the sun sinks toward the horizon. The ensuite feels fresh and spa-like, with a soaking tub, walk-in shower, and water views. A series of screened porches and wraparound decks encourage slow living, morning yoga on the deck, afternoon reading in the shade, sunset grilling and cocktails overlooking the Gulf. Outdoors, a newly installed pool and spa with a sun shelf and expansive sundeck overlook the storied Jewfish Key Sandbar. A private dock with jet ski lift offers instant access to calm waters perfect for fishing, snorkeling, paddle boarding, or exploring neighboring Longboat Key and Anna Maria Island, both just minutes away by boat and beloved for dining, boutique shopping, and laid-back coastal culture. Equal parts island hideaway and refined coastal home, this one-of-a-kind property offers the rare combination of true privacy, effortless access, and natural beauty, set against a backdrop of turquoise water, powder soft sand, and endless sky. Here, relaxation, adventure, and natural beauty converge in a setting that feels almost like an escape, yet unmistakably home.
Listing is courtesy of: SIGHT REAL ESTATE, LLC (877-361-0878)
Listing Agent: Chase Moore (727-325-7272)
5055 GULF OF MEXICO DR #435, LONGBOAT KEY, FL 34228
$600,000144 Days on yellowkey MLS ID: A4671314
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $7,986 (2024)Community: Club Longboat Beach & TennisCondo
Taxes:$7,986
Remarks: Peek-a-boo Gulf views from back deck in this open concept 2-Bedroom, 2-Bathroom Condo at Club Longboat Beach & Tennis Resort. This Longboat Key Retreat offers an expansive 1,484 SqFt of thoughtfully designed living space and combines comfort, convenience. There are 2 balconies one off the living room and the second off the master bedroom. Watch a game of tennis and enjoy the salt air as you unwind with your favorite drink. This is a well maintained residence and some upgrades include: (new HVAC 2025, hot water heater, stainless fridge), this home offers a welcoming, move-in ready atmosphere and provides a sanctuary where you can enjoy both peaceful living and the energy of Longboat Key's vibrant community. Longboat Key is renowned for its pristine beaches, relaxed atmosphere, and upscale lifestyle. With easy access to fine dining, shopping, cultural attractions, and outdoor recreation, it’s the ideal location for those seeking a laid-back coastal lifestyle, while still being close to the excitement of Sarasota. Whether you’re taking a morning stroll on the beach or enjoying the world-class amenities nearby, Longboat Key offers a unique blend of tranquility and activity. Club Longboat Beach & Tennis is more than just a place to live – it’s a destination where every day feels like a vacation. The resort has an expansive calendar full of activities outdoors and the clubhouse has gatherings and various events. Enjoy direct access to the beautiful white sands of Longboat Key Beach, perfect for sunbathing, swimming, and watersports. The community offers resort-style amenities, including meticulously maintained tennis courts, a fitness center, a heated pool (one of which is private for adults only), and 24-hour security. Whether you’re looking to relax poolside or stay active with tennis or fitness, there’s something for everyone. Don’t miss out on the opportunity to own your slice of paradise.
Listing is courtesy of: COASTAL KEY REALTY LLC (941-993-9380)
Listing Agent: Amy Jones (941-993-9380)
624 SAINT JUDES DR, LONGBOAT KEY, FL 34228
$764,900145 Days on yellowkey MLS ID: A4672840
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1387 Built: 1957 Tax: $8,692 (2025)Community: Longboat KeySingle Family
Taxes:$8,692
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)
6800 GULF OF MEXICO DRIVE #184, LONGBOAT KEY, FL 34228
$475,00019 Days on yellowkey MLS ID: A4687722
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1287 Built: 1970 Tax: $6,630 (2025)Community: Whitney BeachCondo
Taxes:$6,630
Remarks: Beautifully renovated in 2023, with dazzling views of the Gulf of Mexico and the private beach across the way, this 2nd floor island retreat is located in a charming Gulf-to-Bay community, nestled between the azure blue water of the Gulf of Mexico and serene Bishops Bayou, where Manatees & Dolphins play. This lovely 2nd level end-unit features an open floor plan, enhanced by a gorgeous designer kitchen with quartz countertop & backsplash and bronze hardware, which overlooks the dining-living room combo, all offering Gulf views. The Florida room overlooks one of the two sparkling swimming pools, which are at your disposal. Hurricane resistant sliding doors and windows offer peace of mind, and the roof has recently been replaced. Luxury vinyl flooring extends all the way through the living space, including the primary suite, which is tucked away for optimal privacy. The screened front patio is the perfect spot to relax and enjoy the turquoise water views, and there is a 9' x 5' storage room for all your toys. Just bring your flip flops & beach wear and start enjoying the laid-back island lifestyle. Two heated pool, tennis & pickleball courts, 23 boat slips, a vintage boathouse/clubhouse, grilling stations, kayak launch, shuffleboard, private deeded beach directly across the road with gazebos and beach lounges plus those amazing sunsets. Two large pets are welcome and the condo can be rented 6 times per year with one month minimum. After a fun-filled day kayaking, beach strolling, fishing or boating, first-class restaurants and casual eateries are located within a short walk, bike or boat ride. Coffee, smoothie & donut shops, liquor store, 24-hour gym, Pilates studio & beauty salon, boutiques and more are just a block away. Don't miss this wonderful opportunity to make your dreams of living on Longboat Key come true!
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Tina Rudek Stark, Pa (941-920-0303)
1211 GULF OF MEXICO DR #610, LONGBOAT KEY, FL 34228
$1,395,00056 Days on yellowkey MLS ID: A4682918
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1827 Built: 1985 Tax: $14,561 (2025)Community: PromenadeCondo
Taxes:$14,561
Remarks: Positioned on the south side and sixth floor of The Promenade on Longboat Key, Residence #610 delivers a true move-in-ready coastal retreat with sweeping Gulf-to-bay views that unfold the moment you enter. From sunrises over Sarasota Bay to sparkling views across the Gulf of Mexico, nearly every room captures water vistas that define the island lifestyle. Offered fully furnished, this updated residence showcases a refined blend of travertine and rich wood flooring, crisp architectural lines, and an abundance of natural light pouring through expansive glass sliders. The open living and dining areas are framed by walls of glass that lead to the private terrace—an ideal vantage point for morning coffee overlooking the Gulf or evening relaxation with the shimmer of bay and downtown skyline vistas in the distance. The contemporary kitchen is thoughtfully designed with sleek surfaces, ample cabinetry, and generous counter space, flowing seamlessly into the main living areas for effortless entertaining. The bright ambiance continues into the bedrooms, where large windows highlight panoramic water and skyline views while maintaining a sense of privacy and comfort. The split-bedroom floor plan ensures privacy, with a spacious primary suite offering dual walk-in closets, terrace access, and an en-suite bath with dual sinks, soaking tub, separate shower, and private water closet. The guest suite includes a walk-in closet and its own en-suite bath, ideal for visitors or seasonal stays. Every detail reflects a residence that has been meticulously maintained and is ready for immediate enjoyment—whether as a full-time home or seasonal escape. The Promenade is a gated, Gulf-front community known for its exceptional amenities and attentive service. Residents enjoy a 24-hour manned guard gate, concierge services, on-site management, secure lobby, health club facilities for men and women, social rooms, four Har-Tru tennis courts, a Gulfside sundeck, and an oversized heated swimming pool and spa. A private boardwalk leads directly to the beach that elevate everyday coastal living. Situated on the south end of Longboat Key, The Promenade offers convenient access to the Longboat Key Club’s golf and marina facilities (access is available with separate memberships), waterfront dining, and nearby shopping. St. Armands Circle and downtown Sarasota are just minutes away, where boutiques, theaters, art galleries, and renowned restaurants define the Cultural Coast lifestyle. Promenade #610 presents a rare opportunity to enjoy turnkey beachfront living with panoramic water views, resort-style amenities, and proximity to everything that makes Longboat Key and Sarasota so desirable.
1241 GULF OF MEXICO DR #803, LONGBOAT KEY, FL 34228
$3,350,000187 Days on yellowkey MLS ID: A4667938
Bed: 3 Bath: 4.0 Liv Area Sq Ft: 3045 Built: 1996 Tax: $31,926 (2025)Community: Water Club 01 At Longboat KeyCondo
Taxes:$31,926
Remarks: The epitome of beachfront luxury awaits in this meticulously renovated 8th-floor residence at the prestigious Water Club on Longboat Key. This stunning 3-bedroom plus oversized study, 4-bath home is a rare offering in one of the Gulf Coast’s premier direct beachfront communities. From the moment you step off the private elevator into the foyer, you’re greeted by serene neutral tones, 10-foot ceilings, and wide-plank engineered hardwood floors that set the tone for elegant coastal living. Walls of glass frame spectacular, unobstructed views of the Gulf of Mexico, filling the expansive living spaces with natural light and breathtaking scenery. The open-concept floor plan seamlessly blends comfort and sophistication, enhanced by recessed lighting and a calming contemporary palette. The spacious living room flows onto a generous beachfront terrace—perfect for soaking in mesmerizing views and the soothing sounds of the surf. The designer kitchen is a showcase of modern design, featuring white glass subway tile backsplash, solid wood cabinetry, an induction cooktop with pot filler, Sub-Zero refrigerator, and premium stainless-steel appliances. A large center island and adjacent breakfast area provide the perfect setting for casual meals with sweeping water views. Each guest suite is a luxurious haven, including one with double queen beds and an en suite bath with soaking tub and separate shower. The third bedroom is currently configured as an office, yet spacious enough to accommodate a queen-size bed, and offers beautiful views of downtown Sarasota. The primary suite is a private retreat, featuring its own beachfront terrace, a separate sitting area, custom-fitted dual closets, and a spacious study with built-in office space. The spa-inspired primary bath is the essence of indulgence with white marble floors and walls, a freestanding soaking tub, and a glass-enclosed walk-in shower. Additional highlights include two under-building covered garage parking spaces, a private storage closet, and access to all the amenities of the Water Club—24-hour security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. This is beachfront living redefined! Located just a short distance to St. Armands and downtown Sarasota's shopping, dining & cultural events.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
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