Location: Longboat Key
Do Not Show Listings
597 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$3,890,000423 Days on yellowkey MLS ID: A4640902
Bed: 5 Bath: 6.0 Gar: 5 Liv Area Sq Ft: 4176 Built: 2025 Tax: $7,998 (2024)Community: Buttonwood HarborSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,998
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: New Construction.... GULF AND BAY VIEWS! THREE OUTDOOR PATIOS! Discover an extraordinary coastal contemporary masterpiece by Floridian Crafted Homes, perfectly positioned on Longboat Key with breathtaking Gulf and Bay views. This 13 FEET ELEVATED, hurricane-fortified residence offers 5 bedrooms, 5 full bathrooms, and 2 partial bathrooms across 4,176 square feet of luxurious living space. Home has elevator shaft blocked in and ready to receive elevator mechanics. Designed for both elegance and functionality, this home features three expansive outdoor living spaces, including two private balconies and a stunning rooftop deck, perfect for capturing the serene Gulf sunsets. The open-concept great room flows effortlessly into the gourmet kitchen, creating an entertainer’s dream, while the second-floor club room offers a private retreat for relaxation. Outdoors, a private pool and spa provide a tranquil escape, while the 5+ car garage ensures ample storage for vehicles and beach essentials. Located just steps from the beach and steps to the upcoming retail and dining destination (Est. Fall 2025), this home also offers access to a community marina with available boat slips, making it ideal for boating enthusiasts. Experience the pinnacle of modern coastal luxury in this exceptional Longboat Key residence—where timeless design, breathtaking views, and an unparalleled location create the ultimate island retreat.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Joshua Freed (941-577-5121)
530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$4,795,000177 Days on yellowkey MLS ID: A4669195
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2025 Tax: $12,064 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$12,064
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—competitively priced and move-in ready. Nestled along a private canal, this 4-bedroom plus den, 4,106 sq ft residence blends contemporary sophistication with coastal appeal. Designed for effortless indoor-outdoor living, the home boasts two spacious lanais, a private pool and spa, and an elevated foundation at 9.5 feet for added peace of mind. Boaters will enjoy concrete canal bulkhead with quick access to the Gulf of Mexico, perfect for endless days on the water. Inside, the home features engineered hardwood flooring, sleek quartz countertops throughout, a large walk-in pantry, and the convenience of dual laundry rooms. Set in a tranquil, private location just minutes from Longboat Key’s renowned beaches, golf courses, and upscale dining, this home is a rare gem. Don’t miss your opportunity to own a waterfront retreat in one of Florida’s most sought-after coastal communities.
726 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$1,090,00042 Days on yellowkey MLS ID: A4684733
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1384 Built: 1963 Tax: $15,835 (2024)Community: Longboat KeySpa: NoSingle Family
Taxes:$15,835
Middle School: W.D. Sugg Middle
Remarks: Coastal Living Perfected on Longboat Key Discover the ultimate island retreat at 726 Jungle Queen Way, a beautifully reimagined 2-bedroom, 2-bath waterfront home where modern comfort meets timeless Florida charm. Tucked away on a peaceful canal just steps from the Gulf of Mexico, this residence offers the rare privilege of deeded beach access, 125ft canal frontage, and a resort-style saltwater pool - everything you need to live each day like a vacation. Wake up to soft morning light glistening off the water and ease into your day with coffee poolside, surrounded by lush tropical landscaping and the hush of palm fronds swaying in the breeze. Launch your boat from the private dock pilings on the deep-water canal and explore Sarasota Bay or head out toward Egmont Key. After a day on the water, rinse off in the outdoor shower, slip into the saltwater pool, or unwind on the travertine deck beneath wide island skies that glow at sunset. Evenings invite laid-back luxury - cocktails by the firepit, good company, and a canopy of stars overhead. Inside, this home blends classic coastal character with thoughtful, high-end updates throughout. The light-filled living spaces feel open yet intimate, with plantation shutters, fresh neutral tones, new baseboards and trim that anchors the living room with style. The redesigned kitchen shines with quartz countertops, stainless-steel appliances, and sleek cabinetry, while both bathrooms echo a spa-inspired sensibility with crisp, elegant finishes. The family room’s canal views beyond the French doors provide a quiet reminder that you’re always connected to the water. Recent updates lend peace of mind with new HVAC (2019), refreshed interior paint, new interior doors, and professional flood mitigation - including new drywall and rewired electrical. The exterior is equally turnkey, with manicured landscaping, a paver driveway, and a shaded carport for convenience. Living on Longboat Key means embracing an effortless, elegant coastal lifestyle. From here, you’re minutes to St. Armands Circle, Anna Maria Island, and downtown Sarasota, with boutique shopping, fine dining, dog-friendly parks, and beach paths all within easy reach. Boat in the morning. Beach at sunset. Poolside under the stars. This is more than a home - it’s the Longboat Key lifestyle realized.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
6801 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$1,175,00046 Days on yellowkey MLS ID: A4684153
1 Days Off yellowkey (back on 3/5/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1328 Built: 1959 Tax: $14,053 (2024)Community: Longbeach On Longboat KeySingle Family
Taxes:$14,053
Remarks: Under contract-accepting backup offers. Discover one of the most coveted parcels in Longboat Key, located in the desirable Longbeach on Longboat Key community! This exceptionally spacious (.43 acre) and private corner lot sits where a calm canal flows into the scenic bayou, offering a truly unique waterfront setting with an extraordinary 243 feet of water frontage - a rare offering in the area. Imagine a custom estate with panoramic water views, multiple private dock possibilities, and direct effortless boat access to the bay within minutes. The lot’s corner position maximizes privacy, natural light and breezes, and provides wide sightlines down the waterway for spectacular sunrises and peaceful evenings over the bayou.
Listing is courtesy of: WAGNER REALTY (941-778-2246)
Listing Agent: Lisa Gaines (941-889-9017)
6810 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$2,250,000170 Days on yellowkey MLS ID: A4669890
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)
761 TARAWITT DR, LONGBOAT KEY, FL 34228
$1,499,000153 Days on yellowkey MLS ID: A4672164
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2377 Built: 1981 Tax: $10,693 (2024)Community: Longboat KeySpa: NoSingle Family
Taxes:$10,693
Remarks: This fabulous waterfront Longboat Key pool home has it all! It is situated on an oversized 11,250sf lot on the canal with 125 feet of seawall, so you can truly enjoy hopping on your boat or kayak or paddle board right outside your back door! It was built strong with steel and precast slab and all of the windows and doors are storm rated or have shutters. Two large garages allow for plenty of storage space, and one of them flows through to the backyard which allows for all your water toys to be easily at the ready. The first floor has 1 of the 3 bedrooms and baths and a large open area for gathering and enjoying the gorgeous backyard. The 2nd floor features the other 2 bedrooms and 2 baths, an open kitchen and living area plus a lovely, light filled dining space overlooking the canal. A large deck area over top one of the garages looks over the sparkling salt water pool with picturesque views and steps down for your refreshing swim. The home has been meticulously kept and is set up for a perfect balance of indoor/outdoor living. All of this plus deeded beach access down the street mean you have covered all the bases to be living the true island lifestyle that Longboat Key is known for.
519 ROUNTREE DR, LONGBOAT KEY, FL 34228
$6,488,000Listed 04/15/2026 9:24PM MLS ID: A4690210
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3554 Built: 2025Monthly Fee: $250 Tax: $9,330 (2024)Community: Longboat Key EstatesSpa: YesSingle Family
Taxes:$9,330
Remarks: BUILT TO LAST. 519 Rountree is new construction built entirely of concrete block (CBS) across every level—unlike many barrier island homes that transition to wood-frame construction above the flood elevation. The residence has already experienced recent hurricanes without damage. NEW CONSTRUCTION. 519 ROUNTREE is a privately positioned coastal residence offering over 6,400 square feet of indoor and outdoor living, including approximately 5,200 square feet under roof and a 1,100 square foot elevator-accessible rooftop terrace, located within Longboat Key Estates. GULF LIVING EXPERIENCE. At 519 Rountree, days begin with morning air carrying the salt-kissed character of the Gulf and conclude with glowing sunsets that define the Florida coastline. This is not simply proximity to the beach — it is immersion in it. Positioned just moments from the sand, the home offers balcony and rooftop experiences designed for sunset entertaining, open-air dining, and the effortless rhythm of Gulf living from morning through evening. WATERFRONT LIVING. A waterside deck is currently in process, transforming the canal setting into a true extension of the home’s outdoor living experience, subject to permitting. Flexibility remains for a variety of dock and lift configurations, tailored to buyer preference. DESIGN AND EXECUTION. The newly constructed residence has withstood three recent hurricanes without damage, a testament to its quality, elevation, and thoughtful execution. Each level is purposeful in both design and function, delivering a vertical lifestyle that feels intuitive, private, and refined. FURNISHINGS. For buyers seeking the residence exactly as photographed, the complete furnishings and curated design package may be acquired separately. FINAL NOTE. 519 Rountree delivers the atmosphere buyers seek when they say they want Gulf living — quietly, privately, and without excess.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Colby Lengel (941-779-6227)
3533 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,995,00093 Days on yellowkey MLS ID: A4678167
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3909 Built: 1999Monthly Fee: $833 Tax: $24,710 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$24,710
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Experience refined coastal living in this spectacular four-bedroom residence located in the prestigious Queens Harbor community of Bay Isles on Longboat Key. Behind the secure gates of Bay Isles, this beautifully updated home blends modern design with timeless elegance on the Harbourside golf course of the Longboat Key Club (Blue #4). Step inside to discover quality craftsmanship and thoughtful updates throughout, including engineered engineered hardwood flooring on the main level and a bright, open layout ideal for entertaining. The fabulous chef’s kitchen impresses with new shaker-style cabinetry, updated granite countertops, Dacor appliances, extended upper and lower cabinetry, a new beverage refrigerator, and an added ice maker—perfectly combining beauty and functionality. The spacious primary suite offers a serene retreat, while an additional second-level suite with en suite bath and generous bonus room adds flexibility for guests or family. A separate cabana suite also provides ideal privacy for visitors. The dedicated office features new, custom furniture, and the upper mezzanine area is newly furnished, offering a stylish secondary living space. Outdoors, enjoy resort-style living with a resurfaced and retiled pool, new pool pavers, upgraded pool equipment access, and lush landscaping enhancements between the pool, fence, and back patio. Relax or entertain by the new Paradise Grill and fire pit, or unwind under the roll out awnings in the beautifully furnished patio lounge area. Additional upgrades include new exterior and interior paint, lighting, ceiling fans, coach lights, feature wall with built-in television and electric fireplace, wine display wall, and epoxy coated garage flooring. Three HVAC systems (2018) and a 2021 water heater ensure year round comfort. Queens Harbor residents enjoy exclusive access to the Bay Isles Beach Club, offering private beach access and world-class amenities. Optional membership is available at the Longboat Key Club for golf, tennis, and marina privileges. This exceptional property represents the best of Longboat Key living—sophisticated, comfortable, and move in ready. Schedule your private showing today.
7030 POINSETTIA AVE, LONGBOAT KEY, FL 34228
$1,099,00027 Days on yellowkey MLS ID: A4686787
REDUCED by $100,000 (8.3%) on 04/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1402 Built: 1934 Tax: $6,672 (2025)Community: Longbeach On Longboat KeySpa: YesSingle Family
Taxes:$6,672
Remarks: MOTIVATED SELLERS! Enjoy as an investment opportunity or your own private retreat in the highly desirable Village neighborhood on the north end of Longboat Key, with no HOA fees and convenient Gulf Beach and Sarasota Bay access. Set on an oversized lot, the property includes a main residence and a separate guest cottage connected by an inviting breezeway, creating excellent flexibility for seasonal use or extended stays. Each space offers privacy and comfort, enhancing overall livability and guest experience. This turnkey furnished property has been thoughtfully restored to preserve its historic charm. Key updates include a metal roof, impact windows, new cabinetry, and updated appliances, providing both character and peace of mind. The main home welcomes you with an enclosed front porch and a warm, inviting living area complete with a wood-burning fireplace, pine wood flooring, and shiplap accents. The updated kitchen features striking countertops and extended workspace perfect for entertaining, with direct access to a private courtyard deck shaded by a majestic tree. The primary bedroom offers vaulted ceilings and a large walk-in closet. The primary bathroom is also tastefully updated. The guest cottage includes its own entrance, ensuite bathroom, private patio, and full kitchenette, making it well suited for guest accommodations or extended stays. Outdoor amenities further enhance the property’s appeal. A covered entertaining area overlooks the pool and spa within a screened lanai, complemented by a well-appointed covered outdoor kitchen. The spacious paver patio and lush tropical landscaping create a private resort-style setting that appeals to long-term or seasonal residents and guests alike. The oversized lot provides ample parking, including space for a boat or golf cart, an added benefit in this beach to bay community. With convenient access to a boat ramp, nearby beaches, waterfront dining and local shops, this charming neighborhood enjoys strong demand. Turnkey and ready to enjoy or generate annual or seasonal rental income, the seller is open to offers.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
510 PUTTER LN, LONGBOAT KEY, FL 34228
$2,999,000101 Days on yellowkey MLS ID: A4676878
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2253 Built: 1968 Tax: $17,343 (2024)Community: Country Club ShoresSpa: NoSingle Family
Taxes:$17,343
Remarks: Welcome to 510 Putter Lane, a stunning canal-front retreat nestled in the coveted Country Club Shores community on the south end of Longboat Key. Completely renovated with meticulous attention to detail, this turnkey furnished 3-bedroom, 2-bathroom residence offers coastal luxury and modern convenience just moments from Sarasota Bay and the Gulf of Mexico and walking distance to the beach. From the moment you arrive, the home's crisp curb appeal hints at the exceptional updates within. A brand-new 24-gauge standing seam metal roof (2025) crowns the home, complemented by all-new impact-rated windows, sliding glass doors (2024), and an elegant new front door (2024), ensuring peace of mind and energy efficiency. Step inside to find an open-concept layout bathed in natural light, where engineered hardwood flooring flows seamlessly throughout. The expansive great room features an electric fireplace set in a stacked stone lighted niche, creating a cozy yet elegant focal point. Plantation shutters, new lighting fixtures, ceiling fans, and recessed lighting add both style and comfort. The gourmet kitchen is a chef’s dream, anchored by a six-burner gas range with a pot filler, custom range hood, quartz countertops, and a suite of brand-new appliances including a refrigerator/freezer, dishwasher, microwave, and ice maker. Soft-close cabinetry offers generous storage, while the floor-to-ceiling built-in wine rack provides a striking and functional design element perfect for entertaining. Both bathrooms have been completely transformed with new tile, cabinetry, lighted mirrors, and high-end fixtures, delivering a spa-like experience. Every inch of this home has been curated for relaxed coastal living with no detail overlooked. Step outside to your private backyard oasis where a newly resurfaced pool and shell stone deck (2024) invite hours of sun-soaked enjoyment. The lush new landscaping and custom landscape lighting enhance the ambiance, while new rain gutters and a new Seawall Cao (2024) will help protect your investment year-round. Boaters will appreciate the direct, no-bridge access to Sarasota Bay. There is also the convenience of a Deed Beach Access! Whether you're spending the day on the water or relaxing poolside at home, this property delivers the quintessential Florida lifestyle. Additional updates include a recently replaced A/C system (2023), ensuring year-round comfort. Offered fully furnished and turnkey, 510 Putter Lane is move-in ready and designed for immediate enjoyment. Country Club Shores is one of Longboat Key’s most sought-after neighborhoods, known for its deepwater canals, beach access, and proximity to the Longboat Key Club, St. Armands Circle, and downtown Sarasota. Rest easy knowing this coastal dream home had no hurricane damage from 2024's storms! Whether you're seeking a primary residence, vacation getaway, or investment property, this exceptional home checks every box. Don’t miss this rare opportunity to own a completely renovated waterfront gem in one of Longboat Key’s most desired communities. 510 Putter Lane offers everything you need—style, substance, and the ultimate coastal lifestyle.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
677 LANDS END DR, LONGBOAT KEY, FL 34228
$2,850,00059 Days on yellowkey MLS ID: A4682565
Bed: 3 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 4000 Built: 1989Monthly Fee: $967 Tax: $33,361 (2025)Community: Lands EndSpa: NoSingle Family
Taxes:$33,361
Remarks: In a rich tropical waterfront setting on Longboat Key, this unique retreat lives like a modern treehouse while evoking a sense of peace, family and comfortable, easy island living. Tucked within the island’s native landscape along a natural bayou off Sarasota Bay, the property offers a rare opportunity to experience serene waterfront living surrounded by nature, with the Gulf’s azure waters and pristine beach access just moments away. Enjoy your private backyard dock and kayak launch or secure your boat on one of the deepwater slips on the open bay. Excellent fishing and bird watching await right outside your door in this remarkable natural habitat. The spacious home is anchored by a stunning great room with vaulted cedar ceilings and exposed beams. The home features a 40-by-9-foot sunroom with bar area and handcrafted art shelves, a dedicated library, an inviting family room and a separate private office with extensive built-in cabinetry, providing warmth and functionality. Extensive decking spans the front entry and wraps around an inner atrium courtyard for alfresco dining. An elevated cabana-style shaded area invites relaxation in sun and shade. The kitchen with center island is positioned for hosting memorable gatherings. The primary suite offers a full wall of windows overlooking the tranquil bayou, two walk-in closets and an additional wall of custom storage. The split floor plan provides a separate wing for guests, featuring two additional bedrooms and baths for convenient hosting. Each guest room offers private access to the outdoor decks and views of the tropical center atrium. Two garages accommodate up to four vehicles, boats, golf carts or paddleboards. Many of the furnishings are included. In Land’s End, an intimate gated community of just 12 residences, owners enjoy maintenance-free landscaping, a heated pool, tennis and pickleball courts, and convenient deepwater boat slips, all artfully tucked among the trees for privacy. From here, it is a short visit or golf cart ride to the captivating sandy Gulf beach or local favorites, including Shore Longboat Key, Mar Vista Dockside Restaurant and Whitney’s. The adjacent plaza also offers multiple popular waterfront cafes, boutique shops, Ventura’s restaurant, and 24/7 gym or Pilates studio. Enjoy mesmerizing sunsets on the Gulf or sunrises on the bay from this waterside community. This is a rare offering in today’s marketplace, capturing the allure of Old Florida living in one of the island’s treasured enclaves.
531 WEDGE LN, LONGBOAT KEY, FL 34228
$2,599,99914 Days on yellowkey MLS ID: A4687694
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2751 Built: 1966Monthly Fee: $21 Tax: $10,602 (2025)Community: Country Club Shores Sec 02Spa: NoSingle Family
Taxes:$10,602
Remarks: A seamless blend of refined design and waterfront living defines this beautifully updated canal-front residence in Country Club Shores. Expanded from its original ranch design, the home offers approximately 2,700+ square feet of thoughtfully curated space, featuring four bedrooms, including dual primary suites on both the first and second levels—an ideal layout for guests or multi-generational living. Each bathroom is finished with timeless, elegant details that elevate the home’s overall sense of sophistication. A comprehensive 2018 renovation introduced elevated style and modern functionality, anchored by a stunning chef’s kitchen appointed with Thermador appliances, built-in refrigeration, and a generous island. Just beyond, an expansive butler’s pantry and secondary prep kitchen enhance both convenience and flow, creating an effortless environment for everyday living and entertaining. Natural light fills the interiors, drawing attention to tranquil canal views and soft glimpses of the bay from the den. The upstairs primary suite serves as a private retreat, complete with its own balcony overlooking the water—an inviting setting for quiet mornings and sunset evenings. Outdoors, a private, low-maintenance setting unfolds with a sparkling pool and beautifully updated waterfront features, including a newer dock, seawall, and 24,000 lb boat lift. Additional highlights include hurricane-impact windows and doors, classic plantation shutters, and 2022 air conditioning systems—completing this exceptional offering in one of Longboat Key’s most desirable waterfront communities. Ideally located just moments from St. Armands Circle, with its renowned dining and boutique shopping, this residence offers a lifestyle of effortless coastal sophistication.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Kerry Mccarthy (720-233-7147)
569 BAYVIEW DR, LONGBOAT KEY, FL 34228
$4,850,000252 Days on yellowkey MLS ID: A4661312
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2025 Tax: $12,064 (2024)Community: Bayview EstatesSpa: YesSingle Family
Remarks: New Construction. Experience the pinnacle of waterfront luxury with this brand-new construction home in the heart of Longboat Key competitively priced and ready for its next owner. Situated on a private canal, this 4-bedroom plus den, 4,106 sqft residence offers the perfect blend of modern elegance and coastal charm. Designed for seamless indoor-outdoor living, the home features two lanais, a private pool with a spa, and an elevated foundation at 9.5 feet. Boating enthusiasts will appreciate the 10,000-lb boat dock and quick access to the Gulf of Mexico for endless days on the water. Inside, enjoy engineered hardwood flooring throughout, quartz countertops in every space, and a large walk-in pantry. The thoughtfully designed layout includes two laundry rooms for added convenience. Nestled in a quiet, private setting, yet just minutes from Longboat Key’s pristine beaches, golf courses, and fine dining, this home is a rare find. Don’t miss the chance to own a waterfront masterpiece in one of Florida’s most desirable locations.
524 HALYARD LN, LONGBOAT KEY, FL 34228
$5,495,000230 Days on yellowkey MLS ID: A4663499
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3737 Built: 2025Monthly Fee: $21 Tax: $17,932 (2024)Community: Country Club Shores IvSpa: YesSingle Family
Taxes:$17,932
Middle School: Brookside Middle
Remarks: One or more photo(s) has been virtually staged. Only ONE BUYER will be the FIRST OWNER! Crafted by an award winning design team, this brand-new coastal contemporary waterfront residence awaits you in the exclusive Country Club Shores community on South Longboat Key. Designed for high performance and easy maintenance, this rock-solid, all block two-story residence with a private elevator provides peace of mind while capturing the essence of easy island living. A fluid open-concept layout is ideal for seamless indoor-outdoor waterfront entertaining. Soaring ceilings with impressive transom glass over casement windows and 10-foot tall sliding glass doors illuminate the interiors with natural light. At the heart of the home, a thoughtfully created gourmet kitchen and wet bar are a showpiece, featuring tailor made modern shaker doors and full panel rift-cut white oak cabinetry. Striking elements include the waterfall island and a dramatic ceiling-height hood, both wrapped in exotic natural Quartzite. A full suite of Wolf & Sub-Zero appliances includes twin 30" refrigerator & freezer towers, an 18" wine tower, under counter beverage centers, wall ovens and a contemporary gas cooktop. The first-floor primary suite is a serene retreat featuring a warm wood-slatted ceiling, expansive glass and a gorgeous bathroom with a freestanding soaking tub, dual vanities and textured porcelain tile accents. An inviting staircase leads to an elevated private home office with a half bathroom. The second floor features a game room with a wet bar and three en-suite guest bedrooms, offering comfort and flexibility complemented by a 30 foot covered balcony overlooking the tranquil water views. Energy-efficient features include variable speed 17 SEER HVAC systems, spray foam insulation and hurricane impact-resistant ES windows and doors. Control4 Smart Home technology provides many conveniences. A host of pre-wired systems—including sound, security, shades and EV charging—can be customized to the buyer's selections. Outside, a brand-new, 100-foot-long, extra-wide seawall protects a resort-style paradise! A four piece French patterned Crema Nova marble decking surrounds the 40-foot linear pool with in-water bench seating, a large sun shelf and a 12 foot wide spa. An elevated lanai with detailed ceilings features an outdoor kitchen, complete with Naturkast marine grade cabinetry, under counter refrigerator and a 42 inch built-in grill offering the perfect retreat for alfresco dining and poolside lounging. All this is just minutes from the extraordinary shopping and dining of St. Armands Circle, the cultural richness of downtown Sarasota, and the world-renowned Gulf beaches of Longboat Key. Seller is offering generous allowances towards custom closets and boat dock design providing an opportunity for the buyer to personalize these features to meet their sytle and preferences!
Listing is courtesy of: HUNT BROTHERS REALTY, INC. (941-388-7017)
Listing Agent: Rob Hunt, Jr (941-232-2431)
524 KETCH LN, LONGBOAT KEY, FL 34228
$1,650,000198 Days on yellowkey MLS ID: A4666645
REDUCED by $149,000 (8.3%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2028 Built: 1968Monthly Fee: $8 Tax: $11,988 (2024)Community: Country Club ShoresSpa: NoSingle Family
Taxes:$11,988
Remarks: Discover the quintessential Longboat Key lifestyle in this classic masonry beach home located just “3” properties in from Sarasota Bay. Boasting 110 feet of canal frontage, your own private dock, a 7,500 lb. boatlift to complement this classic waterfront treasure it offers direct access for boating, fishing, and kayaking, with frequent visits from playful manatees and dolphins right in your backyard canal. The thoughtfully designed 2,000+ square foot split floor plan provides exceptional privacy with 3 bedrooms and 2 baths, ensuring guest suites are comfortably separated from the primary living spaces. The “secret” closet delivers a private office space for when you need to work or plan your next boat trip down the ICW. At the heart of the home, an expansive great room and dining area showcases a wine captain, wet bar, and large refreshment cooler—perfect for hosting unforgettable gatherings while enjoying views of the shimmering enclosed pool and water views of your canal beyond. The chef's kitchen is a culinary masterpiece featuring high-end stainless-steel appliances, built-in ovens, microwave, trash compactor, custom cherrywood cabinetry, separate pantry, and elegant stone countertops with a "chef's prep" island. The layout seamlessly flows into the family room, where glass sliders invite refreshing bay breezes and open to an entertainer's dream: an enclosed lanai, expansive paver patio, and sparkling pool surrounded by multiple seating areas and serene tropical vegetation. Move-in ready with a new HVAC system and generator, this home has been meticulously maintained with numerous upgrades. Please see the attached “Sellers’ Improvement” feature sheet too many to mention…Offered turnkey furnished, it's perfect as either a primary residence or investment property with substantial seasonal rental income potential. The versatile, expansive lot provides endless possibilities to create your ideal waterfront retreat. Situated in the exclusive & sought after neighborhood of Country Club Shores, this property offers an enviable lifestyle just steps from world-class amenities. Directly across the street, you'll find championship golf and tennis at the prestigious Resort at Longboat Key Club, along with sugar-sand beaches and fine dining venues that define the resort experience. The location provides the perfect balance of tranquility and convenience—just minutes to St. Armands Circle, where upscale shopping, eclectic art galleries, and acclaimed restaurants await. Beyond these attractions, Longboat Key offers an array of recreational and cultural experiences, all easily accessible from your doorstep. As a Country Club Shores resident, you'll enjoy exclusive private beach access for only $100 in annual HOA dues—an exceptional value that enhances the already remarkable lifestyle this address provides. Whether you're seeking a year-round sanctuary or a seasonal escape with strong investment potential, this is a rare opportunity to embrace the coveted Longboat Key lifestyle. Schedule your private showing today and discover why this barrier island paradise is one of Florida's most treasured destinations. Come live the dream today & just move right in, it’s all here waiting for you !
Listing Agent: Kathy Callahan (941-900-8088)
5965 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$38,450,00041 Days on yellowkey MLS ID: A4681869
Bed: 11 Bath: 15.0 Gar: 7 Liv Area Sq Ft: 17199 Built: 2026 Tax: $82,342 (2025)Community: Longboat KeySpa: YesSingle Family
Taxes:$82,342
Remarks: Under Construction. Set on nearly two private Gulf-front acres, this visionary estate is emerging as one of the most architecturally significant residences ever conceived on Longboat Key. Designed by the internationally acclaimed firm Sweet Sparkman Architecture & Interiors, the home represents a rare convergence of sculptural design, coastal sensitivity, and modern livability. Bold in concept yet timeless in execution, the main residence unfolds with intention. A dramatic foyer introduces expansive living spaces designed to capture light, scale, and uninterrupted Gulf views. The primary suite is conceived as a private sanctuary, complete with dual spa-inspired baths and bespoke dressing rooms. A stately office, refined lounge, formal dining room, and temperature-controlled wine cellar complement the open-concept great room, which transitions seamlessly to a sweeping Gulf-front terrace. Dual kitchens, a showpiece entertaining kitchen and a separate chef’s kitchen, elevate both daily living and grand-scale hosting. The estate continues upward to a rooftop deck with panoramic coastal vistas, while other levels offer a private cinema, multiple guest suites, and a dedicated guest-level kitchenette. A thoughtfully designed guest house and separate pool house provide additional privacy and flexibility for extended stays or staff accommodations. Outdoors, the setting transforms into a private coastal resort. Lush, layered landscaping surrounds a dramatic resort-style pool and spa, expansive entertaining terraces, tranquil water features, and potential for a private tennis and pickleball court — all oriented toward the Gulf’s endless horizon. Positioned along one of the most coveted stretches of Longboat Key, the property offers both seclusion and proximity to the best of the region, including The Resort at Longboat Key Club, The St. Regis Longboat Key Resort, St. Armand's Circle, and the cultural vibrancy of downtown Sarasota. With construction advancing and pricing evolving accordingly, this is a rare opportunity to secure a generational Gulf-front legacy estate at a pivotal stage. Longboat Key’s global recognition, including its inclusion among Forbes Travel Guide’s Top 12 Destinations, further underscores the enduring value of this extraordinary offering.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
690 FOX ST, LONGBOAT KEY, FL 34228
$725,00064 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: WOW, A SECOND Early Price Drop. Motivated seller, Priced for immediate sale on this fully renovated and furnished Village of Longboat Key Home. Take Advantage Today. 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. This is your unique chance to maximize a truly effortless, luxury island lifestyle. Come and see it today. * Seller has been averaging $55k Gross on seasonal rental.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
569 ROUNTREE DR, LONGBOAT KEY, FL 34228
$2,890,000161 Days on yellowkey MLS ID: A4670192
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3428 Built: 2024Monthly Fee: $167 Tax: $15,281 (2024)Community: Longboat Key EstatesSpa: NoSingle Family
Taxes:$15,281
Elementary School: Pine View School
Remarks: STUNNING New Construction WATERFRONT Home in LONGBOAT KEY ESTATES!!! Experience the pinnacle of coastal luxury in this new modern waterfront residence, perfectly positioned in one of Longboat Key’s most prestigious neighborhoods. Completed at the end of 2024, this architectural masterpiece offers direct Sarasota Bay access and a DEEDED BEACH ACCESS just steps away—the rare opportunity to enjoy both boating and beachside living in one extraordinary setting. Built to today’s highest standards, this all-block concrete home is designed for peace of mind with hurricane impact windows and doors, and engineered to withstand the toughest conditions while exuding timeless sophistication. Clean architectural lines, expansive glass, and a balanced façade define its striking contemporary profile, with an impressive entry that introduces the home’s elegant yet minimalist aesthetic. Inside, a spacious open concept living area seamlessly blends modern design with coastal comfort. The great room centers around a sleek gas fireplace framed by custom built-ins, while floor-to-ceiling sliding doors flood the space with natural light and open to the waterfront terrace. The gourmet kitchen is a showpiece in itself, featuring a massive quartz island with seating for five, custom dark cabinetry, glass subway tile backsplash, and top-tier Italian stainless-steel appliances, including double wall ovens and a gas cooktop. Designer lighting adds a bold splash of color, balancing style and warmth for effortless entertaining. Step outside to a covered deck that extends the main living area, complete with a full summer kitchen, wood-paneled ceiling, and multiple fans for year-round comfort. The third floor rooftop terrace delivers panoramic 360 degree views of the bay and beach—perfect for enjoying unforgettable Florida sunsets. The home offers three luxurious ensuite bedrooms, each with spa like bathrooms and designer finishes. The primary suite is a private sanctuary overlooking the water, featuring a large walk-in closet and a lavish bath with soaking tub, dual vanities, and an oversized walk-in shower. A private mother-in-law suite includes its own bedroom, bath, and full kitchen, providing ideal accommodations for guests or extended family. The backyard oasis is anchored by a sparkling lap pool surrounded by modern pavers and lush tropical landscaping. A brand-new seawall and dock provide deep water access to Sarasota Bay with no fixed bridges to the Gulf, making it a boater’s dream. The four car garage and in-home elevator add both convenience and functionality to this exceptional property. Located in the heart of Longboat Key, just steps from Bayfront Park and minutes from Saint Armands Circle and downtown Sarasota, this home delivers an unparalleled lifestyle. Enjoy world class dining, boutique shopping, championship golf, and some of the most beautiful beaches on Florida’s Gulf Coast—all at your doorstep. DO NOT WAIT ON THIS AMAZING OPPORTUNITY!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Jay Travis, Pa (941-812-7277)
548 GUNWALE LN, LONGBOAT KEY, FL 34228
$2,200,00073 Days on yellowkey MLS ID: A4680965
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1853 Built: 1967Monthly Fee: $17 Tax: $9,801 (2025)Community: Country Club Shores Sec 1Spa: YesSingle Family
Taxes:$9,801
Remarks: Country Club Shores - Completely renovated 3-bedroom, 2-bath canal-front home just three houses from the Bay. Updates include a new flat tile roof (2025), Carrier A/C and A.O. Smith water heater (2024), Pebble Tec pool and paver deck (2024), and newer seawall, dock, and 16,000 lb. boat lift (2.5 years). Enjoy Bay views from the 18 foot x 16 foot Trex dock with lighting and water, plus a 3 foot x 36 foot Trex dock with power and water. Interior features NuCORE waterproof flooring, plantation shutters, Silestone quartz countertops, and new Bosch and GE stainless appliances. The primary suite includes a walk-in closet with built-ins, dual sinks, whirlpool tub, and large shower. Split floor plan with guest bedrooms featuring walk-in closets; one includes a built-in office area. Move-in ready and ideally located for boaters seeking the best of Longboat Key waterfront living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: John August (941-320-9795)
510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228
$4,395,000156 Days on yellowkey MLS ID: A4671696
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5080 Built: 1996Monthly Fee: $208 Tax: $42,201 (2024)Community: Bay IslesSpa: YesSingle Family
Taxes:$42,201
Remarks: An extraordinary Contemporary Architectural estate — now offered with a $500,000 price reduction, presenting one of the most compelling waterfront opportunities on Longboat Key. Defined by its rare three-pod circular design, this sculptural residence is a dramatic composition of flowing living spaces connected by custom corridors — delivering exceptional privacy, abundant natural light, and seamless indoor–outdoor living. The Great Room pod features soaring wood-paneled ceilings and walls of glass framing tranquil water views. The circular primary suite offers a spa-level bath with dual showers, private office, lounge area, and direct pool access. The striking circular kitchen showcases a curved island beneath a two-story ceiling and skylight, with a radial appliance layout that is both artful and highly functional. Two en-suite guest bedrooms open to private patios, while a fully self-contained Secondary Primary Suite above the 32' x 23' three-car garage includes independent HVAC, a luxury bath with Steam Shower and Sauna, a flexible living space ideal for extended guests. Outdoors, enjoy protected deep sailboat water, a private dock with 12,000-lb lift, and a resort-style pool and spa. Situated behind the 24-hour gates of Bay Isles, with exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.
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