Location: Longboat Key
Do Not Show Listings
651 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$835,000171 Days on yellowkey MLS ID: A4680514
REDUCED by $10,000 (1.2%) on 07/06/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2242 Built: 1974 Tax: $18,621 (2024)Community: Longboat KeySingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$18,621
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: PRICE IMPROVEMENT!! Canal-front 3-bedroom, 2-bath home with an attached 1-bedroom, 1-bath apartment above the garage with private entrance, offering 2,242 square feet of total living space. The property has completed remediation and is ready to be rebuilt to suit your needs. Features include high ceilings, a 2-car garage, and a generous ¼-acre lot. Canal offers direct access to Sarasota Bay with no bridges. Conveniently located minutes from marinas, dining, and shopping, with easy access to St. Armands Circle, downtown Sarasota, and Anna Maria Island. Bring your personal touch to recreate this gem or start new and build the home you've always wanted on this 124 ft wide lot. A property with exceptional location and potential.
Listing is courtesy of: ALLEGIANT REAL ESTATE GROUP (941-685-3958)
Listing Agent: Lori Campbell (941-685-3958)
757 HIDEAWAY BAY DR, LONGBOAT KEY, FL 34228
$7,488,000286 Days on yellowkey MLS ID: A4667459
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4507 Built: 2007Monthly Fee: $58 Tax: $29,603 (2024)Community: Hideaway Bay SubSpa: YesSingle Family
Taxes:$29,603
Remarks: Introducing Maison d’Azur, a custom waterfront estate in the prestigious Hideaway Bay enclave on the north end of Longboat Key. WHERE COASTAL LUXURY LIVING MEETS THE BAY! This exquisite four-bedroom, five-bath Key West-inspired residence, crafted by acclaimed builder John Cannon, seamlessly blends indoor and outdoor living to create an atmosphere of refined luxury reminiscent of a boutique hotel. Situated on over a quarter of an acre, this bayfront property commands breathtaking, unobstructed views. Enjoy the vibrant hues of sunrise and sunset over tranquil waters, with palm fronds swaying in the coastal breeze. With a newly renovated private forty-foot-deep water dock and boat lift, Maison d’Azur is a haven for boat enthusiasts and nature lovers. Spend afternoons in the saltwater pool and evenings on the loggia as the Belt of Venus rises over Sarasota Bay. Enjoy dining from your custom outdoor kitchen, surrounded by lush tropical landscaping. Step inside to experience luxury and meticulous craftsmanship, with a grand foyer featuring soaring ceilings and custom pillars. The open floor plan connects a chef’s kitchen, equipped with Sub Zero, Miele, Fisher and Paykel, and Wolf appliances, to a spacious family room with built in cabinetry, creating an inviting atmosphere for entertaining. Archways lead to elegantly decorated formal dining and living rooms. Ascend the private elevator to the second floor, where a great room with a custom entertainment center awaits, along with a study perfect for savoring a cognac on the captain’s porch. The expansive second floor offers a loggia and bedrooms with stunning panoramic views of the pool and Sarasota Bay. Maison d’Azur embodies exquisite taste and timeless beauty. With imported materials and innovative technology throughout, every detail has been curated for an elegant experience. This residence is sold fully furnished, with pieces selected to enhance each room’s design and ambiance. Hideaway Bay is located on Longboat Key, an eleven-mile island off the coast of Sarasota. This enclave of only seventeen estates is steps away from the deeded beach and boasts two private tennis courts. Residents enjoy easy access to premier country clubs, golf courses, waterfront activities, dining options, and upscale shopping. Experience coastal living where every day feels like a vacation amidst the beauty and tranquility of the Gulf Coast. This property sustained no damage from the storms/hurricanes of last year. It boasts an elevation of 10.5’, ensuring you stay high and dry.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Andrea Cohen (786-773-0370)
3527 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,550,00058 Days on yellowkey MLS ID: A4694532
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4154 Built: 1994Monthly Fee: $833 Tax: $22,710 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$22,710
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gated Bay Isles on Longboat Key. This extraordinary two-story residence offers 4 bedrooms, 4.5 bathrooms, and an elegant open floor plan thoughtfully curated with exquisite finishes and designer details throughout. Extensive recent enhancements include a newer roof (2021), new panoramic pool cage with picture-frame screening (2025), new hurricane Armor Screen shutters protecting every opening (2025), and a custom two-person Pneumatic Vacuum elevator, along with numerous additional upgrades and improvements. Dramatic two-story windows fill the expansive great room and chef’s kitchen with natural light while showcasing breathtaking views of the sparkling pool, serene lake, lush landscaping, majestic oak trees, and the manicured fairway. Designed for both everyday living and entertaining, the gourmet kitchen is a culinary masterpiece, complete with a large gas range, dual ovens, solid wood cabinetry, abundant counter space, and a charming breakfast nook framed by bay windows overlooking the pool and golf course. The luxurious first-floor owner’s retreat offers Brazilian cherry wood flooring, vaulted ceilings, French doors opening to the lanai, dual walk-in closets, and a spa-inspired bathroom. Two additional guest bedrooms on the main level are connected by a beautifully appointed Jack-and-Jill bathroom. Outdoor living is equally exceptional, with an oversized pool and spa set within a spacious private lanai designed for relaxation and entertaining while enjoying tranquil sunsets over the lake and golf course. Residents of Queens Harbour enjoy maintenance-free living, a private community pool, and exclusive access to the Bay Isles Beach Club with deeded Gulf beach access. Ideally located near the Longboat Key Club Harbourside golf course, tennis facilities, and the Moorings Yacht Club, this residence embodies the finest in Longboat Key luxury living.
Listing Agent: Miriam Pearson (941-726-4687)
392 FIREHOUSE LN, LONGBOAT KEY, FL 34228
$1,449,00021 Days on yellowkey MLS ID: A4698365
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1761 Built: 2004Monthly Fee: $467 Tax: $17,566 (2025)Community: Conrad BeachSingle Family
Taxes:$17,566
Remarks: Located on the coveted west side of Gulf of Mexico Drive, just steps from the beach, 392 Firehouse offers the relaxed coastal lifestyle Longboat Key is known for. Nestled on a quiet cul-de-sac surrounded exclusively by charming Key West-style homes, this beautifully updated residence blends timeless island architecture with thoughtful modern enhancements. Residents also enjoy the community pool located directly across the street, along with the convenience of walking to three of Longbeach Village's beloved restaurants, making it easy to embrace the island lifestyle. Designed for effortless indoor-outdoor living, the home features an enlarged rear deck, fully equipped outdoor kitchen, outdoor shower, and a gas fire pit—creating the perfect setting for entertaining or unwinding after a day at the beach. Hurricane-impact sliding glass doors provide a seamless connection to the outdoor living spaces while filling the home with natural light. The home's curb appeal has been thoughtfully elevated with an updated exterior stucco finish, classic Bahama shutters, an artistic shell stone paver driveway, new professional landscaping, and landscape lighting that enhances the property after sunset. Inside, refinished hardwood floors bring warmth and character throughout, while sleek glass railings in the loft add a contemporary architectural element. The primary suite is enhanced with custom California Closet built-ins, providing exceptional organization and storage. Additional improvements include a new air conditioning system (2023), Tesla electric vehicle charging station, and an irrigation system. Offering an exceptional location just steps from the Gulf beaches, within one of Longboat Key's most charming coastal enclaves, this meticulously updated home embodies the very best of island living.
Listing is courtesy of: BRISTA REALTY LLC (941-373-0500)
Listing Agent: Gina Ursini (941-812-4894)
677 LANDS END DR, LONGBOAT KEY, FL 34228
$2,695,000153 Days on yellowkey MLS ID: A4682565
REDUCED by $95,000 (3.4%) on 06/12/2026
Bed: 3 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 4182 Built: 1989Monthly Fee: $967 Tax: $33,361 (2025)Community: Lands EndSpa: NoSingle Family
Taxes:$33,361
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: W.D. Sugg Middle
Remarks: Experience the timeless appeal of a quintessential Florida island home, immersed in a lush tropical waterfront setting on Longboat Key. Elevated above a serene natural bayou off Sarasota Bay, this distinctive residence embodies the relaxed elegance of island living, with soaring ceilings, expansive wraparound decks, and pristine Gulf beaches just moments away. Launch a kayak from your private dock, enjoy exceptional fishing and bird-watching from your backyard, or keep your boat in one of the community's deepwater slips on the open bay. The association offers slips up to 43 feet in length, and either your private dock on the bayou or a bayfront slip may accommodate an optional boat lift. The spacious elevated residence is anchored by a dramatic great room featuring vaulted cedar ceilings and exposed beams. An expansive sunroom with a bar area and handcrafted display shelving, a dedicated library, an inviting family room, and a private office with extensive built-in cabinetry contribute to the home's distinctive character. The entire main living area is thoughtfully arranged on a single level. Extensive decking welcomes you at the front entry and wraps around a lush central atrium courtyard, creating exceptional spaces for outdoor dining, entertaining, and relaxation. A shaded cabana-inspired retreat offers comfort throughout the day, while the setting is equally suited for the addition of an elevated outdoor spa. The kitchen, centered around a generous island, is perfectly positioned for gathering with family and friends. The primary suite features a wall of windows overlooking the tranquil bayou, dual walk-in closets, and an additional wall of custom closet storage. A desirable split floor plan creates a private guest wing with two additional bedrooms and baths. Each guest room enjoys direct access to the surrounding decks and views of the tropical atrium. Two garages accommodate up to four vehicles and provide ample space for boats, golf carts, paddleboards, and additional storage. Most furnishings are included. Within Land's End, an intimate gated enclave of just 12 residences, owners enjoy maintenance-free landscaping, a heated swimming pool, tennis and pickleball courts, and beautifully landscaped grounds nestled among mature trees for exceptional privacy and convenient bay access. From here, a short walk or golf cart ride leads to the Gulf beach and popular island dining destinations, including Shore Longboat Key, Mar Vista Dockside Restaurant, and Whitney's. Nearby waterfront cafés, boutique shopping, fitness facilities, and a Pilates studio further enhance the island lifestyle. Enjoy breathtaking Gulf sunsets and tranquil bay sunrises from this exceptional waterfront community. Rarely does a property so perfectly capture the spirit of Old Florida, where tropical beauty, boating, nature, and beachside living come together in one of Longboat Key's most treasured island enclaves.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
595 BOWSPRIT LN, LONGBOAT KEY, FL 34228
$3,099,000275 Days on yellowkey MLS ID: A4668868
REDUCED by $41,000 (1.3%) on 07/05/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2550 Built: 1966Monthly Fee: $21 Tax: $26,814 (2025)Community: Country Club ShoresSingle Family
Taxes:$26,814
Remarks: Longboat Key Waterfront Luxury. Experience the ultimate in waterfront living in this 4-bedroom, 2.5-bath Country Club Shores residence, tucked just off Sarasota Bay on a nice canal with quick access to the Gulf, sandbars, and every boating adventure Sarasota has to offer. A private dock, two boat lifts (20,000 lb and 7,000 lb), new seawall, and a custom fish cleaning station create a true boater’s paradise, while canal and bay views enhance the coastal setting. After a day of boating, sandbar hopping, fishing, or cruising the bay, come home to your heated pool, travertine-decked outdoor retreat. Retractable glass sliders, and pool bar blur the line between indoors and out, making this the perfect place to gather, unwind, and relive the day’s best moments on the water. Thoughtfully remodeled twice in recent years, the home blends refined coastal style with exceptional updates including a 2016 effective build year, roof, plumbing, electrical, PGT hurricane-impact windows and sliders, and two new A/C systems in 2024. The chef’s kitchen is a standout, featuring custom Devittori cabinetry, leathered granite, a dramatic 11’x5’ island, and premium Sub-Zero and Wolf appliances. Deeded private beach access, nearby Longboat Key Club amenities, and close proximity to St. Armands Circle and Downtown Sarasota complete this exceptional island offering.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Melissa Gissinger (941-404-2722)
552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228
$975,000164 Days on yellowkey MLS ID: A4680786
0 Days Off yellowkey (back on 7/3/2026)
REDUCED by $24,999 (2.5%) on 06/03/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1846 Built: 1960 Tax: $17,419 (2024)Community: Sleepy Lagoon ParkSingle Family
Taxes:$17,419
Middle School: Martha B. King Middle
Remarks: Under contract-accepting backup offers. Imagine living the coastal lifestyle only dreams are made of! Wake each morning to the sunrise over your local beach—just a short stroll down the street—where you can sink your toes into sugary white sand, take an early walk, or collect seashells along the shore. Return home to enjoy coffee outdoors by your heated pool, relaxing on the deck as tranquil water views set the tone for the day. Take a refreshing dip, then unwind as nature’s canvas unfolds before you, with shifting light and brilliant shades of blue and azure. In the evening, hop on your boat from your backyard and cruise effortlessly to waterfront restaurants and sunset destinations. With a 20,000-lb boat lift, personal watercraft lift, and a 40-foot dock on a deep-water canal, you’ll enjoy immediate access to Sarasota Bay, the Intracoastal Waterway, and the Gulf—with no fixed bridges along the way. End your days with breathtaking sunsets as the sky ignites in color, dolphins play, and manatees glide by. Inside, the home offers an optimal floor plan ready for your personal touches. The spacious eat-in kitchen features an expansive island perfect for casual entertaining, complemented by new stainless-steel appliances. A wall of sliding glass doors seamlessly blends indoor and outdoor living, filling the home with natural light and water views. All main living areas open to the pool and outdoor spaces. Recent updates include a new AC system and a recently refinished pool. The home offers three bedrooms and four baths, with the flexibility to modify the layout or easily add a fourth bedroom. A wood-burning fireplace adds warmth and charm to the living room. Located on the barrier island of Longboat Key, this exceptional property is perfectly suited for the most discerning buyers. Enjoy nearby golf, pickleball, boutique shopping, and dining, with St. Armands Circle and downtown Sarasota just minutes away. Convenient access to SRQ Airport makes this an ideal full-time residence or luxury vacation retreat. Call today to schedule your private showing and experience coastal living at its finest.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kathy Cahill (941-807-3565)
791 BROADWAY ST, LONGBOAT KEY, FL 34228
$1,625,00060 Days on yellowkey MLS ID: A4694059
Bed: 2 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 2236 Built: 1995 Tax: $9,600 (2025)Community: Longbeach VillageSingle Family
Taxes:$9,600
Remarks: Welcome home to 791 Broadway, nestled in the heart of historic Longbeach Village on the North end of prestigious Longboat Key. This elevated island-style residence offers the perfect blend of coastal charm, comfort, and relaxed island living. Thoughtfully designed across multiple levels including a large 11x30 third floor FLEX SPACE that could easily be converted into a 3RD BEDROOM. This home captures beautiful morning sunrises, colorful sunsets, and stunning views of Sarasota Bay and the intracoastal waterway. From the moment you step inside, you are greeted by an abundance of natural light, soaring ceilings, plantation shutters, and inviting open spaces that are ideal for both everyday living and entertaining. The property offers wonderful flexibility, including an oversized garage with plenty of room for golf carts, kayaks, bicycles, beach gear, and more. The outdoor living areas are equally inviting, with several unique spaces to relax and enjoy the surroundings — from the covered front porch to the rear deck overlooking the water, along with the peaceful sound of multiple water features throughout the property. Recent updates add comfort and peace of mind, including new impact-resistant and energy-efficient windows, two AC units, updated flooring, and many additional improvements that make this home feel warm, welcoming, and move-in ready. Enjoy the charm and convenience of the Village, just a short stroll from community fishing piers, a boat launch, exceptional dining, and the white sandy beaches and turquoise waters of the Gulf of Mexico. This is a wonderful opportunity to experience the laid-back Longboat Key lifestyle in one of the island’s most beloved neighborhoods.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Matthew Voss (941-402-8799)
721 BINNACLE POINT DR, LONGBOAT KEY, FL 34228
$1,499,000536 Days on yellowkey MLS ID: NS1083611
1 Days Off yellowkey (back on 7/2/2026)
REDUCED by $96,000 (6.0%) on 06/16/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3229 Built: 1973Monthly Fee: $50 Tax: $6,896 (2024)Community: Emerald HarborSpa: NoSingle Family
Taxes:$6,896
High School: Manatee High
Middle School: Electa Arcotte Lee Magnet
Remarks: Under contract-accepting backup offers. PREMIER LOCATION in Emerald Harbor -- HOUSE TO BE DEMOLISHED -- LOT IS GRADED AND READY TO BUILD -- Located on the apex of the WIDEST CANAL on Longboat Key, 721 Binnacle Point Drive is ready for a new owner with a new vision! The property has 96' of canal frontage with BRAND NEW Sea Wall (2024), 120' of street frontage, with just over 18,800 SF upon which to build your dream home. Build new and enjoy long views east and west down the canal and the beautiful light exposure. Emerald Harbor is one of Longboat Key's best neighborhoods - don't miss this opportunity to create your vision! There is a working, permitted sprinkler well on property. Private, deeded beach access for Emerald Harbor residents is just over 1100 feet away! *The 3/3 home on the property that was damaged by Hurricane has been removed.
Listing is courtesy of: KINCAID REALTY (386-428-7800)
Listing Agent: James Frost (386-299-9245)
500 HALYARD LN, LONGBOAT KEY, FL 34228
$1,995,000131 Days on yellowkey MLS ID: A4683571
0 Days Off yellowkey (back on 6/13/2026)
REDUCED by $154,000 (7.2%) on 05/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2311 Built: 1967Monthly Fee: $21 Tax: $23,973 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$23,973
Remarks: Huge Price Reduction. Flexible Terms. Best-Priced Waterfront in Country Club Shores. Gorgeous Views and Updated. New Roof, New Seawall, New Impact Windows & Doors - 1/2 Acre Elevated Waterfront Lot - Enjoy the Longboat Key Island Lifestyle. In a prime South Longboat Key location, this beautifully updated waterfront home offers a blend of privacy, comfort and exceptional boating access. Set on a large, elevated, tropically landscaped lot, the property captures wide water canal views stretching toward Sarasota Bay, with stunning water vistas visible from nearly every room. Designed with an inviting open floor plan, the residence features three bedrooms and two baths, thoughtfully arranged for everyday living and effortless entertaining. The private primary suite is a retreat, complete with stunning water views, generous walk-in closet, an en-suite bath and a unique outdoor shower for enjoying the coastal lifestyle. A separate guest suite provides privacy for visitors, while the cozy third bedroom offers flexibility for additional guests, an office or hobby space. In addition, the open floor plan seamlessly blends dining and living areas to capture stunning water views throughout. Recent upgrades bring beauty and peace of mind, including a new metal roof, new hurricane-impact windows and doors, a new hurricane-rated screened pool cage, new air conditioner, and new seawall and composite dock. The outdoor living spaces are equally impressive, highlighted by a screened-in pool area with spa and an additional screened room off the pool, ideal for relaxing or entertaining while enjoying tranquil water views. Boating enthusiasts will appreciate the new seawall and private composite dock, with easy access to Sarasota Bay and the Gulf of Mexico and no fixed bridges along the way. The large paver driveway adds curb appeal, while the dedicated laundry room includes front-load washer and dryer for convenience. Completing the coastal lifestyle, the property includes deeded beach access, allowing you to enjoy sunrise views over the bay and sunset walks along the Gulf. Seller willing to work with a qualified buyer on terms. This exceptional home offers the best of Longboat Key living, privacy, upgrades, water views, deeded beach and outstanding boating access. Schedule Your Private Showing.
Listing Agent: Michael Seamon (941-586-1802)
744 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$975,000189 Days on yellowkey MLS ID: TB8463320
1 Days Off yellowkey (back on 7/1/2026)
REDUCED by $150,000 (13.3%) on 06/29/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1688 Built: 1963 Tax: $7,142 (2024)Community: Longboat KeySpa: NoSingle Family
Taxes:$7,142
Remarks: Under contract-accepting backup offers. Laid-back Living on Longboat Key -- A Boater's Paradise! Welcome to 744 Jungle Queen Way, a fully renovated, FURNISHED 3-bedroom, 2-bathroom coastal retreat on the stunning Longboat Key! Whether you're a boating enthusiast, a beachcomber, or someone who just loves the island life, this home delivers the ultimate Florida lifestyle. ***Prime Location & Waterfront Living Nestled just seven homes away from Sarasota Bay, this property is a boater's dream with two boat lifts, offering quick access to the Gulf of Mexico's crystal-clear waters. Spend your days fishing, cruising, or island-hopping--all from your backyard! ***Deeded Beach Access - Just 777 Steps to Paradise... take a short stroll across Gulf of Mexico Drive and find yourself on the powdery sands of Longboat Key's legendary beaches. Enjoy sun-soaked days, breathtaking sunsets, and gentle Gulf breezes right outside your door. ***Close to Local Favorites & Hidden Gems. In just a short walk, you'll find island hotspots like the Lo'Key Island Grille, Guppy's Restaurant, and the award-winning Euphemia Haye. A short boat ride, you can enjoy The Shore, Cortez Kitchen, Swordfish Grille, Tide Tables, Anna Maria Oyster Bar, Bridgetenders and Dockside restaurants. ***Modern Updates with Coastal Charm. Step inside to an open-concept layout featuring a spacious, upgraded kitchen with solid wood cabinetry and stone countertops -- perfect for entertaining. The home's split-bedroom design ensures privacy, while the extra-wide lot provides a natural buffer between properties for peace and tranquility. ***Take a short scenic 1-mile stroll from your front door to enjoy the beauty of Florida's coastal landscape at Joan M. Durante Park and the Sarasota Bay overlook dock for a peaceful escape. This 32-acre bay front nature preserve features winding boardwalks, shaded trails, and scenic waterfront views, perfect for birdwatching, peaceful walks, or catching a sunrise over the mangroves. ***Your Slice of Island Paradise Awaits! Whether you're looking for a full-time residence, a vacation getaway, or an investment property, this home captures the essence of laid-back luxury. Don't miss your chance to live the dream on Longboat Key! ***Schedule your private showing today!
Listing is courtesy of: YOUR HOMETOWN REALTY, INC. (813-645-7007)
Listing Agent: Teddi Aberle (813-645-7007)
549 HALYARD LN, LONGBOAT KEY, FL 34228
$2,195,00027 Days on yellowkey MLS ID: A4696535
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1594 Built: 1965Monthly Fee: $23 Tax: $20,602 (2025)Community: Country Club ShoresSingle Family
Taxes:$20,602
Remarks: This is the one * PERFECTLY POSITIONED ON A QUIET CUL DE SAC STREET AT THE PREFERRED SOUTH END OF LONGBOAT KEY * Located on the QUIET END OF THE CANAL with OPEN WATER JUST BEYOND YOUR DOCK and the PRIVATE BEACH ACCESS ONLY MINUTES AWAY * A quick 3 minute cruise to Sarasota Bay & the ICW & The GULF * This coveted Country Club Shores IV home has been LOVINGLY RENOVATED with a NEW Kitchen & modern amenities while retaining its classic charm * NEW KITCHEN CABINETS * NATURAL GAS STOVE * GE CAFE APPLIANCES * NEW Solid Core Doors * FULL HURRICANE PROTECTION * NEW TILE Flooring throughout * 2 Car Garage has a NEW Mini Split A/C * Primary Suite with a Spa-style Bath featuring a LARGE Walk-in Shower * BEAUTIFUL VIEWS OF YOUR POOL & PRIVATE CANAL * This THOUGHTFULLY CURATED HOME is an open floor plan * The additional Bedrooms are well-appointed and located in a way that allows for guest privacy * Impact Sliding Glass Doors surround the Outdoor Area * ROOF IS 9 YEARS YOUNG * WATER HEATER IS 3 YEARS YOUNG * All of this wraps your Caged Pool with Paver Decking and a Paver Walkway to your 2021 NEW SEAWALL & COMPOSITE DOCK with a 10,000lb Boat Lift & 2 Additional NEW Jetski Lifts PLUS a 2-step down Kayak Dock Launch with Power & Water * THIS IS A BOATER'S DREAM * The PERFECT HOME & OUTDOOR OASIS to entertain family & friends or just simply relaxing in your slice of paradise * PRIDE OF OWNERSHIP SHOWS IN THIS IMMACULATE HOME * Furniture is available * Just bring your suitcase * Country Club Shores is a well established waterfront neighborhood offering DEEDED BEACH ACCESS with a convenient south end location close to ST ARMAND'S CIRCLE, The new ST REGIS, and even downtown Sarasota * Join the Longboat Key Club offering 45 holes of championship golf & world class tennis * Your family will love this home * One look & you'll fall in love! *
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Ryan Brown (941-330-7774)
612 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
$22,500,000501 Days on yellowkey MLS ID: A4643123
0 Days Off yellowkey (back on 6/30/2026)
Bed: 6 Bath: 8.0 Gar: 9 Liv Area Sq Ft: 9243 Built: 2024 Tax: $32,107 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$32,107
Remarks: Under contract-accepting backup offers. Welcome to your private, gated estate on Longboat Key, where coastal luxury meets effortless sophistication. Boasting over 730 feet of water frontage, this stunning property offers panoramic views of Whitney Bayou and Harris Canal and provides the ultimate waterfront lifestyle. With 9,243 square feet of air-conditioned living space and a total of 21,562 square feet on over an acre of pristine land, this estate is a masterpiece of design and craftsmanship. Designed in the timeless British West Indies style, this home showcases vaulted ceilings, extensive trim detailing, white oak floors throughout, and two fireplaces, creating an ambiance of elegance and warmth. The expansive covered patios and porches invite you to embrace the serenity of waterfront living, while the heated pool and an impressive 13' x 13' hot tub serve as the ultimate retreats. A custom outdoor fire pit, two outdoor kitchens, and indoor and outdoor pool tables elevate the entertainment experience. For boating enthusiasts, this estate is unrivaled, featuring four low-profile boat lifts—the largest accommodating vessels up to 30,000 pounds, the second suitable for a vessel up to 20,000 pounds, and the third and fourth lifts each with a 5,000-pound capacity, ideal for jet skis, kayaks, and paddle boards. Located just 10 minutes from the Gulf of Mexico by boat and 5 minutes to Shore and Mar Vista restaurants, this is the perfect haven for life on the water. Inside, the Wolf Sub-Zero appliances provide top-tier performance in a gourmet kitchen built for culinary excellence. A Control4 smart home system offers seamless automation throughout, while HVAC-equipped garages ensure comfort year-round. The multiple garages can accommodate up to 9 cars, and the massive driveway can host 20+ vehicles. The residence boasts six spacious bedrooms, each with an en-suite bathroom, plus an additional full bath and two half baths. Designed for both productivity and leisure, the home features his and hers offices, a media/theater room, a fully equipped gym, sauna, golf simulator, tackle garage, and a workshop. A private guest suite with a separate entrance includes a kitchenette, dining room, living room, bedroom, and bathroom, offering a luxurious retreat for visitors. With two state-of-the-art elevators, expansive landscaping, and a maintenance-free turf yard, this estate blends modern convenience with natural beauty. Ideally located near pristine beaches, world-class shopping, and gourmet dining, this estate is the epitome of waterfront elegance and exclusivity. Experience the pinnacle of coastal living—this is truly paradise found.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Charles Buky (941-228-6086)
2945 PYRULA DR, LONGBOAT KEY, FL 34228
$3,125,00065 Days on yellowkey MLS ID: O6408404
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4340 Built: 2024 Tax: $36,325 (2025)Community: Coquina BeachSpa: YesSingle Family
Taxes:$36,325
Remarks: A contemporary masterpiece awaits Your going to love this house !, constructed in 2024 and completed in December of 2025 this newly built residence blends contemporary architecture with uncompromising craftsmanship. The craftsmanship, and finishing touches puts this property in a class by itself when making your buying comparisons. Worth repeating….Your going to love this house! Step into more than 4300 square feet of modern design perfection ideally located in one of Longboat Keys most coveted neighborhoods. Just minutes on foot brings you to pristine beach access or a tee time at the prestigious Longboat Keys club. Seamless indoor- Outdoor living, a stunning floor to ceiling glass wall sets the tone from the moment you walk in revealing a private courtyard that feels like your own luxury resort, complete with an elegant pool, a relaxing spa, and a fully equipped outdoor kitchen and dining area. This harmonious flow creates an exceptional living experience where the outdoors becomes an extension of the home . Refined interiors inside , warm oak wood flooring runs throughout the home beautifully paired with stone accents , sleek cabinetry , and high end finishes. The chef designed kitchen is crafted for culinary excellence and features quartzite countertops prized for their durability, beauty, and unmistakably high end character. The primary suite is a serene retreat with glass walls overlooking the courtyard , a soaking tub , a separate shower, and generous storage. Spaces designed for comfort the home offers five bedrooms including An in law suite with a kitchenette, private laundry, spacious bedroom, and walk in shower. An additional bedroom on the main level with its own private balcony . Upstairs two guest suites connected by a bright relaxation area with courtyard views through the floor to ceiling glass. Striking modern architecture, the exterior showcases clean contemporary lines enhanced by rare hand selected stone and rich custom woodwork. Come visit this spectacular offering. ..
Listing is courtesy of: PROPERTIO (888-817-3383)
Listing Agent: Alin Zdroba (888-817-3383)
6489 GULFSIDE RD, LONGBOAT KEY, FL 34228
$13,995,000184 Days on yellowkey MLS ID: A4677413
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 6616 Built: 2026 Tax: $42,641 (2025)Community: Sleepy LagoonSpa: YesSingle Family
Taxes:$42,641
Remarks: This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.
Listing Agent: Nicholle Mckiernan (941-928-2922)
530 CHIPPING LN, LONGBOAT KEY, FL 34228
$5,749,000134 Days on yellowkey MLS ID: A4685275
REDUCED by $50,000 (0.9%) on 06/26/2026
Bed: 5 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4216 Built: 2026Monthly Fee: $21 Tax: $16,910 (2025)Community: Country Club Shores Sec 02Spa: YesSingle Family
Taxes:$16,910
Remarks: Introducing the newest custom residence by Brista Homes, where exceptional craftsmanship and thoughtful design come together in a limited and highly refined offering. Nestled along a quiet canal in the sought-after waterfront community of Country Club Shores, this 4216 square-foot residence captures the essence of the Longboat Key boating lifestyle. With desirable south-facing rear exposure, tranquil canal views create a peaceful backdrop to daily living, while upper balconies frame beautiful views of Sarasota Bay. The home’s architecture, floor plan, and interior selections were curated by Brista’s in-house design team, drawing on years of experience building on Longboat Key and a deep understanding of what today’s waterfront buyers value most—timeless architecture, premium materials, and seamless indoor-outdoor living. A handcrafted iron pivot entry door framed by natural stone detailing creates a striking first impression. Inside, pocketing glass doors open the main living spaces to a resort-style outdoor setting where a custom salt water pool and elevated heated spa are surrounded by porcelain pavers and lush coastal landscaping. A fully equipped outdoor kitchen creates the ideal setting for entertaining along the water. At the heart of the home, the kitchen blends refined design with exceptional functionality. Custom Italian cabinetry is complemented by a dramatic Quartzite waterfall island and matching hood feature. A premium appliance suite by Miele — including a built-in refrigerator, integrated dishwashers, speed oven, and built in coffee maker — is complemented with a striking 48-inch dual-fuel range. A hidden butler’s pantry and custom wine display add both style and practicality for effortless entertaining. The great room centers around a sleek linear fireplace, creating a sophisticated gathering space. Upstairs, a spacious club room with a media wall and wet bar offers a relaxed setting for evenings with family and guests. Architectural details throughout the home include white oak plank flooring, a dramatic floating staircase, recessed baseboards, and clean modern lines that reflect a refined coastal aesthetic. Modern conveniences include whole-home audio, a whole house generator, multi-zone climate control, and integrated security. Located within one of Longboat Key’s most desirable boating communities, where deepwater canals provide quick access to Sarasota Bay and the Gulf of Mexico, this newly completed custom residence represents a rare opportunity to experience waterfront living defined by thoughtful design, exceptional craftsmanship, and enduring quality.
1600 HARBOR SOUND DR, LONGBOAT KEY, FL 34228
$11,900,00080 Days on yellowkey MLS ID: A4692027
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5689 Built: 2026Monthly Fee: $792 Tax: $24,527 (2025)Community: Bay IslesSpa: YesSingle Family
Taxes:$24,527
Remarks: Pre-Construction. To be built. Positioned directly across from the iconic St. Regis Longboat Key Resort, this exceptional waterfront residence offers immediate access to world-class amenities, pristine Gulf beaches, fine dining, and championship golf. Located within the exclusive double-gated Harbor Section of Bay Isles on Longboat Key, 1600 Harbor Sound Drive represents a rare convergence of scale, location, and boating capability, crafted for those seeking a refined Gulf Coast lifestyle at the highest level. Set on an expansive 18,043-square-foot corner homesite, the property features an impressive 135 feet of deep-water canal frontage, with the ability to accommodate multiple lifts (up to three) and a substantial vessel. This level of frontage and flexibility is increasingly rare, even among premier waterfront estates. Spanning 5,689 square feet under air, the residence is thoughtfully designed to balance grand-scale entertaining with comfortable everyday living. The home includes 5 bedrooms, a bonus room or office, 5.5 bathrooms, and a 4-car garage. Soaring ceilings and expansive glass openings create a bright, open environment with seamless indoor-outdoor transitions, complemented by refined, designer-level finishes and a private elevator servicing all levels. The chef’s kitchen is executed with top-tier appliances, clean architectural lines, and a level of detail rarely seen in spec construction. A full-scale butler’s pantry, complete with its own stove, provides exceptional functionality and allows for seamless entertaining while keeping the main kitchen pristine. The primary suite is designed as a true retreat, featuring separate his-and-her bathrooms and a fully integrated wellness experience, including a sauna and steam room, bringing a spa-level environment into daily living. Every element has been carefully curated to deliver comfort, functionality, and a sense of understated luxury throughout. Outdoor living is equally compelling, with a resort-style pool and spa, along with a fully equipped outdoor kitchen, covered dining, and lounge areas. These spaces are perfectly positioned to capture the tranquility of the waterfront setting while embracing Florida’s year-round coastal climate. Opportunities of this caliber, combining substantial frontage, strong boating capability, a wellness-driven design, and a premier Harbor Section address are increasingly limited. 1600 Harbor Sound Drive presents a compelling offering for the discerning buyer seeking a newly built waterfront estate in one of Sarasota’s most prestigious enclaves.
Listing Agent: Rinat Sikdar (941-993-9292)
500 HARBOR COVE CIR, LONGBOAT KEY, FL 34228
$12,250,00027 Days on yellowkey MLS ID: A4697649
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5120 Built: 2026 Tax: $20,619 (2025)Community: Bay IslesSpa: YesSingle Family
Taxes:$20,619
High School: Riverview High
Remarks: Under Construction. Now nearing completion and expected to be delivered in approximately 60 days. Positioned within the exclusive Harbor Section of Bay Isles on Longboat Key, 500 Harbor Cove Circle is a newly constructed waterfront estate offering a rare combination of exceptional boating access, modern architecture, resort-inspired living, and one of the Gulf Coast’s most coveted addresses. Located behind the double gates of Bay Isles and directly across from The St. Regis Longboat Key Resort, residents enjoy immediate proximity to world-class hospitality, fine dining, marina services, championship golf, and tennis, while ownership includes access to the Bay Isles Beach Club. Encompassing 5,120 square feet under air and 8,564 square feet total, the residence features 5 bedrooms, 5 full baths, 1 half bath, a private office, elevator access to all levels, and a 4-car garage. A fully integrated smart home automation system provides seamless control of lighting, climate, security, audio, window treatments, pool and spa functions, and key home systems throughout the property. The arrival experience unfolds through a lagoon-inspired reflecting pool, floating stairway, and lush tropical landscaping, creating a dramatic resort-style arrival. Architectural lighting, natural stone, warm wood accents, and expansive walls of glass establish a sophisticated coastal aesthetic throughout the residence. Inside, expansive living spaces are enhanced by Venetian plaster, custom millwork, large-format stone surfaces, and carefully curated architectural details. One of the home’s defining architectural statements is a dramatic 20+ foot monolithic travertine feature wall wrapping an entire corner of the residence, creating a striking design element rarely found in residential construction. The chef’s kitchen is anchored by an oversized Calacatta marble waterfall island, premium custom cabinetry, integrated appliances, and generous entertaining space. Designed for seamless indoor-outdoor living, the residence opens to expansive covered terraces, a resort-style pool and spa, and a fully equipped outdoor kitchen featuring a grill, pizza oven, refrigeration, and multiple gathering spaces. Wellness-focused amenities include a private fitness area, sauna, cold plunge, and dedicated spaces for relaxation and recovery, creating a private wellness retreat. For boating enthusiasts, the property offers approximately 100 feet of protected waterfront frontage with direct access to Sarasota Bay and the Gulf of Mexico in less than two minutes. The dock is designed to accommodate a substantial yacht while still providing room for multiple additional lifts for a tender, fishing boat, personal watercraft, and other recreational vessels—an increasingly rare offering among Florida’s premier waterfront estates. One of the Gulf Coast’s rare opportunities to enjoy new construction, large-yacht capability, and resort-inspired living within the exclusive Harbor Section of Bay Isles.
3040 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$1,899,00075 Days on yellowkey MLS ID: A4692587
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3009 Built: 1995 Tax: $8,653 (2025)Community: Triton CoveSpa: YesSingle Family
Taxes:$8,653
Remarks: Welcome to island living on Longboat Key, one of Sarasota's premier barrier island destinations. In Triton Cove, this coastal residence offers direct Gulf Beach access across the street and a lifestyle designed for boating, seasonal use or year-round living along Florida's Gulf Coast. Enjoy nightly sunsets along Gulf of Mexico Drive or experience world-class dining and shopping on nearby St. Armands Circle. An elevated entry leads to the main living level, where expansive glass defines the open-concept design, connecting the living room, kitchen and dining areas. Positioned within a five-residence enclave, this property offers convenient access to Sarasota dining, shopping and waterfront recreation while supporting a low-maintenance ownership experience. This tri-level single-family home features four bedrooms and 2.5 baths, complemented by a two-car garage with dual 8-foot doors and extensive storage. The ground level includes multiple flexible-use rooms ideal for fitness, storage or organization of beach equipment, kayaks, bicycles and boating gear. A dumbwaiter provides direct access from the garage to the kitchen. Interior features include engineered wood flooring in main living areas and new carpet in bedrooms. The kitchen is designed with wood cabinetry, granite countertops, deep storage drawers, an appliance garage, a rollout pantry wall and stainless steel appliances, including a GE wall oven/microwave combo, an induction cooktop and an LG refrigerator. Additional features include a wet bar with cabinetry and a mirrored wall, an electric fireplace and plantation shutters. The primary suite offers a private setting with dual vanities, a soaking tub, a separate shower, two walk-in closets and a Juliette balcony with partial gulf views. The third level includes a bonus room suitable for media, an office or a private retreat. Outdoor living includes a natural gas-heated pool and spa, an outdoor shower and a private fenced setting. Pool systems including a new motor, filters and heater, and the interior of the pool has been refinished. Recent improvements include a 2024 shingle roof with warranty, zoned HVAC systems installed in 2018 and 2020, and a 2025 water heater. The home includes a monitored alarm system. Triton Cove offers a maintained environment with low monthly HOA fees of $500, including landscape maintenance of common areas, pest control, pool service and exterior lighting. Leasing is permitted up to four times annually with a one-month minimum. Located near Longboat Key Bayfront Park and Longboat Dog Park, residents may enjoy pickleball, tennis, playgrounds and picnic areas. Nearby conveniences include grocery, pharmacy, boat rentals and storage options along Longboat Key, as well as being within reach of Sarasota amenities. Optional membership to the Longboat Key Club provides access to golf, tennis, beach and social amenities, enhancing the gulf-front lifestyle experience on Florida's west coast. Don’t miss out on your private tour of this special coastal home featuring four bedrooms, 3000-plus square feet of air-conditioned living space, a two-car garage, a 30-foot pool and a hot tub on Longboat Key with beach access with low taxes for under $2 million; this is an extraordinary value!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Frank Lambert (941-920-1500)
1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228
$4,550,000293 Days on yellowkey MLS ID: A4666688
REDUCED by $200,000 (4.2%) on 04/29/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4209 Built: 1987 Tax: $16,980 (2024)Community: Bay IslesSingle Family
Taxes:$16,980
Remarks: Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Julie Klick (941-780-6001)
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