Location: Longboat Key , 34228
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4750 GULF OF MEXICO DR #Villa 8, LONGBOAT KEY, FL 34228
$799,00077 Days on yellowkey MLS ID: A4679944
REDUCED by $51,000 (6.0%) on 04/15/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1504 Built: 1974 Tax: $2,954 (2025)Community: Windward Bay AmdVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,954
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: AMAZING $51,000 PRICE IMPROVEMENT! YOUR SUNRISE SANCTUARY! YOUR SUNSET ESCAPE! An End Unit Villa—Steps From Both Shores! There’s a moment just before sunrise—when soft light touches the bay and the world feels brand new. From this beautifully updated 1504 sq foot, 3-bedroom, 2-bath end-unit villa, you wake to that glow each morning. And while the bay lies just a short stroll from your door—where dolphins and manatees grace the shoreline—the sense of tranquility begins the moment you step inside your villa. Welcome to your story at Windward Bay, Loved for 33 Years, Transformed for the Next Chapter! Brand-new luxury vinyl plank flooring stretches throughout the living spaces. Custom White wooden plantation shutters open like pages of a book, revealing light-filled rooms, a bright inviting great room and a refreshed kitchen where new soft-closing cabinetry meets the timeless richness of granite countertops. Being a corner end unit means privacy, extra windows, and the kind of natural light you feel more than you see. The great room spills out to your private outdoor patio—perfect for morning coffee, late lunches, or evening breezes. And as evening arrives, simply walk across the street. The Gulf paints the sky in gold and coral, offering unforgettable sunsets that become a treasured part of your daily rhythm. This home offers peace of mind along with beauty. It’s a place where you can truly exhale. This is effortless, maintenance-free living, where parking sits mere steps from your door and bringing in groceries is a breeze. No elevators. No stairs. No inconvenience. Just the freedom of ground-level coastal life. Here, maintenance-free living means all the big things are already done: the entire exterior was upgraded in 2020 with hurricane-impact windows, hurricane-impact sliding doors, and a new roof. "Pet Friendly" Windward Bay is one of Longboat Key's most beloved waterfront communities—known for its mature landscaping, resort-style amenities, and genuine sense of warmth. People don't just move here; they stay here. In fact, the current owner of this villa has lived here for 33 years, a testament to the comfort, community, and connection the neighborhood provides. Windward Bay isn't just a place to live. It's a place to belong. Spanning 26 lush acres, the community offers three beach access points, a 1/2-mile nature trail, two heated pools, fitness center, sauna, clubhouse, tennis and pickleball courts, kayak launches, boat docks (waitlist), covered parking, and storage. Wildlife is abundant throughout the property, adding magic to everyday life. Financially strong, Windward Bay has completed its Milestone Inspection and Capital Reserve Study. Monthly fees were reduced in 2025 and increased only $13 for 2026. With Downtown Sarasota, St. Armands Circle, Bridge Street, renowned restaurants, championship golf, boutique shopping, and cultural attractions just minutes away, you're perfectly positioned between quiet island tranquility and vibrant coastal life. A Home That Feels Like a Vacation—Every Single Day! A place ready for its next chapter—your chapter. Your Windward Bay story starts here—reserve your private viewing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Debby Mccaig (941-544-1713)
2326 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$915,00051 Days on yellowkey MLS ID: A4683180
REDUCED by $35,000 (3.7%) on 04/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2282 Built: 1986Monthly Fee: $143 Tax: $10,215 (2025)Community: Harbour Oaks 2Villa
Taxes:$10,215
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: A rarely available END UNIT villa is located on Longboat Key within the gated Bay Isles community, offering the opportunity to embrace true island living with expansive private terrace space and tranquil pond views fed by the saltwater bay. Encompassing nearly 2,400 square feet of thoughtfully designed interiors, this residence delivers privacy, security, and effortless elegance in one of Sarasota’s most coveted coastal enclaves and just moments from Gulf beaches. Inside, soaring vaulted ceilings and inviting natural light pour in, creating an airy and refined atmosphere. The well-appointed floorplan balances sophistication with comfort, featuring multiple gathering spaces including a formal living room anchored by a charming wood-burning fireplace. Expansive sliding doors seamlessly connect the interior to an impressive 740-square-foot private terrace overlooking the serene pond waters, creating a seamless indoor-outdoor lifestyle ideal for sunset entertaining, morning coffee, or elegant evenings under the island sky. Rich wood flooring, plantation shutters, granite countertops, and updated cabinetry reflect timeless coastal luxury. A skylight enhances the kitchen with beautiful natural light, while recent improvements including a NEW AIR conditioning system (2025) and NEW ROOF (2025). Two private atriums introduce lush greenery and architectural interest, adding intimate moments within the home. A thoughtfully designed office with a built-in Murphy bed offers flexibility and can easily function as a fourth bedroom, accommodating guests with ease. The primary suite serves as a spacious sanctuary, while guest bedrooms offer privacy and comfort for family and visitors alike. The private two-car garage features organized storage for beach and recreational essentials, supporting a seamless island lifestyle. Residents of Harbour Circle enjoy a heated community pool and spa surrounded by manicured tropical landscaping, along with exclusive membership to the gated Bay Isles Beach Club — providing private Gulf-front access with convenient dedicated parking. Living on Longboat Key means enjoying easy access to world-renowned beaches, boating, fine dining, and the amenities of the Longboat Key Club, including golf, tennis, pickleball, marina access, and multiple private dining venues (membership available separately). Everyday conveniences including Publix, banks, the post office, and Longboat Key’s Town Center are just moments away. Quiet, private, and impeccably maintained, this fully furnished end-unit villa offers the feel of a single-family residence while delivering the sophistication and prestige of island living on Longboat Key. Don’t miss your opportunity—schedule your private showing today and experience elevated coastal living firsthand.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
4760 GULF OF MEXICO DR. VILLA 7, LONGBOAT KEY, FL 34228
$549,999153 Days on yellowkey MLS ID: A4671823
REDUCED by $24,501 (4.3%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 931 Built: 1974Monthly Fee: $21 Tax: $1,629 (2025)Community: Windward Bay AmdVilla
Taxes:$1,629
Remarks: UNBEATABLE VALUE! AMAZING PRICE FOR A BRAND NEW BEACH & BAY VILLA! Renovated with precision, the final finishing touches were completed in 2025 (12 weeks in living time since renovation) for this quality engineered, down to the studs, two-bedroom and two-bath beach getaway villa. From the moment you step inside, you'll be greeted by a thoughtfully designed sunny open floor plan boasting recessed lighting and an array of sleek finishes throughout the home. Distinguishing features include the true craftmanship of custom solid core doors, chic beach themed door and cabinet knobs, custom designed laundry closet housing a Full-sized front load Samsung washer & dryer, self-close solid kitchen cabinets with a bonus spice rack cabinet, pull out shelves in the pantry and below the sink, ceramic floor tiling through-out including a curb less shower entry located in the primary suite’s “ensuite bathroom. The pièce de résistance is the Cambria Quartz (lifetime warranty) kitchen countertop chosen for the beach inspired aqua accents that showcase both a breakfast bar and a dual temperature wine/beer refrigerator for added pleasure. The second bedroom is cleverly designed to serve as both an office and a guest space, complete with a comfortable “guest chest” Murphy bed cabinet. For peace of mind while away, the villa is equipped with the latest Wi-Fi enabled keyless smart lock entry system, as well as a smart remote thermostat to monitor and manage remotely. Worry free living with a New A/C (2022), Water Heater (2024) and recent Hurricane Impact Windows/Sliding Doors, Roof, & Carport (2020). Located directly across the street, with 3 beach access points (one private deeded access) is the tranquil Gulf with its crystal-clear turquoise blue waters and uncrowded sandy beaches that attract visitors from all over the world. A low-density residence and a nature lover’s delight: from captivating bird watching to the frolicking dolphins and manatees of Longboat Key. Windward Bay's unparalleled amenities include 2 tennis/pickleball courts, 2 marinas with 28 boat & jet ski slips for a low monthly fee (first come first served), barbecue grills throughout, fishing piers, 2 fish cleaning stations, kayak racks, 2 heated pools, shuffleboard, bike racks, a clubhouse with kitchen, library, fitness room, meeting room, 2 saunas, and community fire pits throughout the property. Conveniently accessible to Downtown Sarasota, St. Armands Circle, Anna Maria Island, Historic Cortez Fishing Village, Championship Golf Courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Welcome home to “Pet Friendly” Windward Bay, where TWO pets are allowed. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced. This wonderful condominium exemplifies “Florida Gulf to Bay Living” at its finest. Windward Bay: "A Special Place and A Gem of a Community." Whether you're looking for a vacation home or a permanent residence, book your private showing today. Longboat Key and Villa 7 in Windward Bay offer everything you could desire to live the life you have always dreamed of!
4900 GULF OF MEXICO DR #203, LONGBOAT KEY, FL 34228
$689,000162 Days on yellowkey MLS ID: A4670932
REDUCED by $10,000 (1.4%) on 04/08/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1325 Built: 1975 Tax: $8,395 (2025)Community: Windward Bay AmdSpa: NoCondo
Taxes:$8,395
Remarks: IN THE COVETED "B" BUILDING, A STRATEGIC PRICE REFINEMENT NOW POSITIONS THIS EXCEPTIONAL RESIDENCE AS THE MOST COMPELLING OFFERING AT WINDWARD BAY! A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend. Wake up to spectacular sunrises over the sparkling bay and unwind with mesmerizing sunsets on the Gulf, directly across the street. Watch playful dolphins, jumping fish, gentle manatees, and vibrant Florida birdlife from your Florida Room or while preparing meals in your updated kitchen overlooking the shimmering waters. Your primary suite is a serene waterfront retreat, perfect for moonlit nights and sunrise mornings. Every detail of this condo has been thoughtfully designed to create a lifestyle of tranquility and relaxation, including remote controlled blinds in the Florida Room. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. The Windward Bay Association has been busy with a multitude of improvements and updates in the last few years including: Brand new roofs, resealing the buildings bayfront exteriors and painting of all the midrises in 2023/2024. Private roads were repaved and a new 1/2 mile long salt-tolerant privacy hedge was planted in October 2025. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced and 2026 Condo Fees only increased by $13 a month. This is more than a home—it’s a lifestyle. Experience the beauty, serenity, convenience, and the maintenance free life you’ve always dreamed of. GREAT NEWS, PAST CAPITAL IMPROVEMENT ASSESSMENTS WERE PAID IN FULL BY SELLER, NOT ADDED TO MONTHLY DUES! Schedule your private showing today and make paradise yours!
2341 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$1,399,9909 Days on yellowkey MLS ID: A4688219
0 Days Off yellowkey (back on 4/15/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2282 Built: 1986Monthly Fee: $1,617 Tax: $11,814 (2025)Community: Harbour Oaks 2Spa: NoVilla
Taxes:$11,814
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to your elevated and relaxed Longboat Key lifestyle—where everything has already been beautifully updated - all that’s left to do is move in and enjoy. Tucked behind the gates of Bay Isles in the charming Harbour Oaks enclave, this bright and open end-unit villa offers gorgeous golf course views, peaceful water features and those unforgettable sunset skies that make every evening feel like a getaway. Inside, the home has a Serena & Lilly feel - its fresh, comfortable and thoughtfully designed. With 2,282 square feet, three en-suite bedrooms and a light-filled open layout - it’s ideal for both relaxed everyday living and hosting friends and family. New luxury vinyl plank flooring runs throughout, while vaulted ceilings, skylights and a garden atrium brings in beautiful natural light. The kitchen has been fully updated with quartz countertops, a marble backsplash, stainless appliances and a casual breakfast bar—perfect for morning coffee before heading to the beach. There’s also a separate dining space for more intimate dinners. Outdoor living is where this home really shines. Sliding doors open to a spacious, two-level screened lanai with a newly pavered deck, electric awning for shade and a newly resurfaced and retiled PebbleTec saltwater pool. It’s your own private retreat—perfect for lounging, entertaining or simply soaking in the peaceful golf course views. The bathrooms have been beautifully reimagined with marble showers, Kohler fixtures and clean, modern finishes. Additional updates include a new roof (2025), newer AC and water heater (2021) and a two-car garage for convenience. Upgrades are plentiful - including Hunter Douglas window treatments and plantation shutters - which add a polished but easygoing feel. Living in Bay Isles means enjoying a true resort lifestyle, with access to a private beach club, marina and scenic walking paths—all in a gated, maintenance-free community. You’re just minutes from the Longboat Key Club and Tennis Center, Publix, everyday conveniences - and a short drive to the shops and restaurants of St. Armands Circle and downtown Sarasota.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Monica Verinder (941-704-4040)
408 GULF OF MEXICO DR #1214, LONGBOAT KEY, FL 34228
$99,0003 Days on yellowkey MLS ID: A4689763
Bed: Bath: 0.0 Built: 2006 Tax: $563 (2025)Community: Boathouse On LongboatDock-Rackominium
Taxes:$563
Remarks: Welcome to Slip #1214 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities PLUS the price includes a 2018 Robalo R18 with a Yamaha 150 motor, recently detailed tuned up for one-stop shopping! This premium slip accommodates boats up to 31.5 feet in length, with a maximum height of 8' 4" and an 8' 6" beam (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and even the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Daniel Treiman (917-657-7495)
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
Tax Year: 2024
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
Middle School: W.D. Sugg Middle
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)
4320 FALMOUTH DR #103, LONGBOAT KEY, FL 34228
$525,00069 Days on yellowkey MLS ID: A4681530
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $6,901 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$6,901
Remarks: Luxury Waterfront Living | Proven Income Potential Experience refined coastal living in this pristine, pleasantly updated 2-bedroom, 2-bath residence, offered fully furnished and move-in ready. Enjoy spectacular harbor and Intracoastal water views from both the living room and bedroom, extending to the enclosed lanai—an ideal setting for relaxing mornings and elegant evenings. This residence features an excellent rental history, making it a rare opportunity for investors seeking immediate income, while also serving as a perfect full-time or seasonal retreat. Located in an amenity-rich waterfront community, residents enjoy exclusive access to a private beach club pavilion at 4415 Gulf of Mexico Drive, featuring men’s and women’s restrooms, indoor showers, and optional beach and chair storage. Additional private storage is included on the second floor. Resort-style amenities include four heated swimming pools, a fully equipped fitness center, banquet hall with catering kitchen and dance floor, art studio, billiard and card rooms, and professional on-site management. Boat docks available on a first-come basis with water and electric, accommodating sail or power boats up to 34 feet. Additional highlights include mini golf and a scenic waterfront promenade along the harbor and canal. An exceptional opportunity to enjoy luxurious waterfront living or secure a high-performing investment at an incredibly affordable price point. Schedule your private showing today—this opportunity won’t last.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Malihe Karimi (941-376-5099)
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
Taxes:$12,064
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.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Joshua Freed (941-577-5121)
1085 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228
$999,00068 Days on yellowkey MLS ID: A4681713
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1819 Built: 1981 Tax: $8,830 (2025)Community: Beachplace IiiSpa: YesCondo
Taxes:$8,830
Remarks: Spacious 3-Bedroom End-Unit Residence in Sought-After Beachplace Welcome to this beautifully maintained three-bedroom, two-bath end-unit condominium offering exceptional natural light, generous living spaces, and serene views in one of South Longboat Key’s most desirable beachfront communities. The open living and dining areas are thoughtfully designed for comfort and entertaining, featuring expansive sliders and windows that flood the space with sunlight and create seamless indoor-outdoor flow. A spacious living room opens to a south-facing screened lanai—perfect for enjoying morning light, golf course views, and gentle coastal breezes. The kitchen is bright and functional, offering ample cabinetry, full appliance package, and convenient in-unit laundry tucked neatly into a dedicated closet. Adjacent dining space provides flexibility for everyday living or hosting guests. The primary suite is generously sized and enjoys tranquil views, abundant natural light, and direct access to the lanai. Two additional bedrooms are versatility for guests, family, or a home office, all thoughtfully laid out to maximize privacy and comfort. Being an end unit, this residence benefits from additional windows and enhanced light throughout, creating an airy, welcoming atmosphere. Neutral finishes and tasteful furnishings allow for immediate enjoyment while offering an excellent canvas for personalization. Residents of Beachplace enjoy resort-style amenities, including a heated pool with lap lanes, spa, tennis courts, a fully equipped clubhouse with gathering spaces, on-site management, and private deeded beach access complete with lounge chairs and umbrellas. The community’s prime location places you moments from St. Armands Circle, Longboat Key Club, and downtown Sarasota’s dining, shopping, and cultural attractions. This well-cared-for residence presents an outstanding opportunity—whether as a primary home, vacation retreat, or income-producing investment in a premier Gulf-front community.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228
$899,00048 Days on yellowkey MLS ID: A4683112
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $7,576 (2025)Community: Islander Club Of LongboatCondo
Taxes:$7,576
High School: Riverview High
Remarks: Welcome to The Islander Club — your turnkey getaway awaits! Step into coastal living with this beautifully updated residence offering effortless style and year-round relaxation. The open, sun-filled layout features tasteful luxury finishes and seamless access to a 38-foot terrace, perfect for unwinding after a day at the beach. Unit 54S has been thoughtfully upgraded throughout, showcasing wood flooring, an updated kitchen with stainless steel appliances, refreshed bathrooms, and unique architectural details that add character and charm. The sunlit primary bedroom includes an ensuite bathroom, a large walk-in closet, and a cozy seating area ideal for reading or enjoying your morning coffee. The spacious second bedroom welcomes guests with terrace access and a generous closet for added storage. The Islander Club’s resort-style amenities include a private 400' beachfront, heated pool, brand-new fitness center, two new sauna rooms, a Har-Tru™ tennis court, two pickleball courts and on-site management for true lock-and-leave convenience. The Islander Club has recently completed an extensive series of capital improvements that elevate both the structural integrity and the everyday experience of the community. Enhancements include exterior stucco repairs and balcony waterproofing, new roofs on the carports, clubhouse, and both residential towers, and modernized pool facilities with new resurfacing, tile, and equipment. Additional upgrades such as refreshed landscaping and lighting, hurricane-rated windows and doors, and a fully renovated fitness center further enhance the appeal and long-term value of the property. Whether you’re seeking a seasonal retreat or a full-time coastal home, this move-in-ready gem delivers the best of island living and peace of mind.
Listing Agent: Julie Lojacono Mackie (773-704-1438)
4500 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$739,00021 Days on yellowkey MLS ID: A4685838
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1975 Tax: $2,843 (2025)Community: Windward Bay AmdCondo
Taxes:$2,843
Remarks: GORGEOUS BAYFRONT PENTHOUSE VIEWS Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living. Schedule your private showing today.
Listing Agent: Marcela Terrell (941-929-3010)
4440 EXETER DR #301, LONGBOAT KEY, FL 34228
$585,00042 Days on yellowkey MLS ID: A4684917
REDUCED by $10,000 (1.7%) on 04/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1970 Tax: $8,101 (2024)Community: Longboat HarbourCondo
Taxes:$8,101
Remarks: Welcome to this beautifully updated top floor corner furnished residence with Gulf and Bay views that is move in ready. Coming furnished with an open kitchen floor plan and an enclosed lanai overlooking the pool and Sarasota Bay. Large plank ceramic tiles throughout and ceiling fans in every room, hurricane impact glass windows in the kitchen and living area and a washer/dryer has been added. All tv's within the residence stay. The Longboat Harbour community is located mid-Longboat Key with amenities to enjoy including a large clubhouse where many activities occur, with a catering kitchen and dance floor, art studio, billiard and card rooms, and a fully equipped fitness center. In addition, the community has four heated swimming pools, putting green, tennis and pickleball courts, kayak storage, boat slips available for a minimal annual fee for up to a 34’ boat, mini golf, a scenic waterfront promenade along the harbor and canal, and access to a private gated Beach Club on the Gulf side with bathrooms, showers and beach items. The building has just completed a new roof installed. There is additional storage withing the building for each residence as well as a storage closet on the enclosed lanai.
Listing Agent: Michael Moulton (941-928-3559)
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)
2295 GULF OF MEXICO DR #115S, LONGBOAT KEY, FL 34228
$895,000169 Days on yellowkey MLS ID: A4670081
2 Days Off yellowkey (back on 4/15/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $10,253 (2024)Community: Islander Club Of LongboatCondo
Taxes:$10,253
Remarks: Under contract-accepting backup offers. Wonderful "Manhattan Style" beachfront Condo with sweeping views of Sarasota Bay and views of the Gulf now available at the popular Islander Club on LBK. This gorgeous beachfront renovation was completed 4 years ago and truly shows all the craftmanship that went into the process under the owner's direction. Open kitchen beings the morning light into the room for enjoying your coffee or tea as you gaze across the sparking blue waters of the bay. Large 38ft balcony also has views of bay and a bit of the Gulf of Mexico. The Primary suite is a comfortable 13X20 which accesses the balcony and has a large walk-in closet. It is light and bright and a restful haven away from the main living area. The Islander club has recently renovated their clubhouse. The gym overlooks the gulf and the pool. There is a conference room, library, and an Olympic size heated pool, not to mention their Har-Tru tennis courts. The Location is very convenient. The shops of Bay Isles with the Publix and CVS are just a couple of minutes away. It's only 10 minutes to World renown St Armand Circle. Make this your permanent home or your week-end getaway. Secured Building . At The Islander Club "Everyday is a Holiday and Life is an endless vacation.
Listing Agent: Michael Nink, Pa (941-914-2805)
1445 GULF OF MEXICO DR #501, LONGBOAT KEY, FL 34228
$1,499,00017 Days on yellowkey MLS ID: A4687339
0 Days Off yellowkey (back on 4/10/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2642 Built: 1982 Tax: $19,801 (2025)Community: Players Club IiiCondo
Taxes:$19,801
Remarks: This stunning corner penthouse spans over 2,800 sq. ft. and boasts breathtaking views of the Gulf, Bay, and city skyline. Key features include elegant stone floors, storm-resistant windows, custom cabinetry, skylights, raised ceilings, and indirect lighting. The kitchen offers a breakfast bar and an adjacent Solarium, perfect for enjoying your morning coffee while taking in both Gulf and city vistas. The spacious sitting room/office adjacent to the primary bedroom features built-in desk and shelving, with expansive glass walls overlooking the pool and Gulf. For entertaining, the impressive 800 sq. ft. private courtyard includes a large fountain and a summer kitchen. This residence also includes a private garage and an additional assigned under building parking space. Residents of The Players Club enjoy a guarded entrance, on-site management, a resort-style saltwater pool and cabanas, spa, Har-Tru tennis courts, pickleball, putting green, a fitness center, renovated clubhouse with catering kitchen, outdoor entertainment area with fire pits, barbecue grills, and direct access to a white sand beach. All of this is just minutes away from the vibrant shops, restaurants, theaters, and art galleries of St. Armands Circle and Downtown Sarasota.
Listing Agent: Ian Addy, Pa (941-961-8850)
6951 GULF OF MEXICO DR #14, LONGBOAT KEY, FL 34228
$899,000367 Days on yellowkey MLS ID: A4648003
4 Days Off yellowkey (back on 4/15/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1170 Built: 1973 Tax: $11,138 (2024)Community: Sea PinesSpa: NoCondo
Taxes:$11,138
Remarks: WOW! The minute you open the front door of this first floor Coastal Retreat Seaside condo, you will be captivated by the shimmering, turquoise Gulf of Mexico Water View and the Panoramic Sandy White Beach in front of you. You'll be eager to get a closer look from the glassed in Florida Room, so you may overlook the beauty of this updated, attractively furnished & decorated first floor residence at Sea Pines, a small 28 unit beach front condo complex on the north end of Longboat Key, Florida. Since purchasing five years ago, these owners have lovingly transformed this almost 1400 square foot, corner unit with extra windows, open concept, two bedroom with En Suite baths & walk in closets to today's coastal contemporary style tastes. Improvements include light oak color Luxury Vinyl wide plank flooring throughout, Samsung stainless steel appliances including washer & dryer, new HVAC installed, updated the primary bedroom with a quartz counter vanity, tiled & glass door shower, and fitted out closet. The condo's interior was painted as well & new, high quality neutral colored living room, dining & bedroom furniture, rugs, lighting & drapery, artwork and a large entertainment center installed. A new tiled roof was installed on this building in 2024. Additional features include impact resistant windows in both bedrooms & the office adjacent to the kitchen. Plantation shutters cover all these windows. This office area is fitted out with oak cabinetry, desk & drawers, perfect for working at home. The spacious 26-foot-long lanai (Florida Room) can be entered from either the primary bedroom or the living room via sliders. This may be your favorite room with mesmerizing Gulf & beach views over the sea grass pathways to the water. And of course, the magnificent Longboat Key Gulf of Mexico sunsets will thrill you whether watching from your lanai or enjoying on the beach while toasting your good fortune! This turnkey handsomely appointed & attractively furnished seaside retreat offers great rental income if you so wish. Currently these owners are using RVA Rentals, but a new owner can choose how or if to lease out this unit. Rental friendly Sea Pines can be leased out six times a year with a one month minimum time period. Two additional benefits to this first floor Unit 14 are that these owners have paid $5357 assessment for new landscaping for the complex plus new interior glass sliders will be installed in the living room & primary bedroom and sellers have paid for that as well. Sea Pines has an electronic gated entry for security & privacy. Amenities include a large, heated pool, is large pet friendly & offers excellent rental income possibilities. Charming Longboat Village is nearby with fabulous restaurants like The Shore, Mar Vista, Whitney's, Ventura's & the thriving Whitney Shopping Center. Anna Maria Island is just across the Longboat north end bridge for additional night life entertainment.
Listing Agent: Maruta Miluns (941-374-9702)
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