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MANCHESTER BAY - A4694394 - 3606 FAIR OAKS PL, LONGBOAT KEY, FL 34228 Just Added on 05/26/2026 5:02PM
$4,999,000 | Single Family Home | 5 beds | 3.0 baths | 2 gar
Nestled behind the gates of the highly celebrated Bay Isles community, this exceptional five-bedroom waterfront residence at 3606 Fair Oaks Lane offers the perfect blend of luxury, comfort, and peace of mind with an impressive list of recent upgrades and improvements. Designed for effortless coastal living, this beautifully updated home showcases refined interiors, expansive outdoor living spaces, and direct boating access, all within one of Longboat Key’s most sought-after neighborhoods. From the moment you arrive, the home’s meticulous maintenance and thoughtful renovations are immediately apparent. A roof just two years old, hurricane shutters on all windows and doors, and multiple updated mechanical systems provide exceptional value and confidence for years to come. Inside, the residence has been extensively renovated in 2026 with stunning new engineered wood flooring flowing throughout the home, creating a warm and welcoming coastal aesthetic. The spacious floor plan offers five generously sized bedrooms, ideal for accommodating family and guests while maintaining privacy and flexibility for today’s lifestyle needs. The heart of the home is the beautifully refreshed kitchen, complete with brand-new KitchenAid appliances installed in 2026, blending modern functionality with timeless design. Adjacent living and dining areas are filled with natural light and seamlessly connect to the outdoor entertaining spaces, creating an inviting atmosphere perfect for both everyday living and hosting gatherings. Every bathroom in the home was completely renovated in 2026 with stylish finishes and contemporary details that elevate the home’s overall elegance. Extensive system upgrades include three HVAC systems replaced in 2022, 2023, and 2026, along with a new hot water heater installed in 2026, ensuring maximum efficiency and comfort throughout the property. Outdoor living is equally impressive and designed to embrace the Florida waterfront lifestyle. The pool area underwent a significant transformation in 2025 with new pool decking, a resurfaced pool finish, updated waterline tile, and a new gas pool heater, creating a true private resort setting. In 2026, the addition of a fully equipped outdoor kitchen elevated the entertaining experience even further, offering the perfect backdrop for waterfront dining and sunset gatherings. Boating enthusiasts will appreciate the new 10,000-pound boat lift installed in 2025 along with a beautifully updated dock and deck, providing quick and convenient access to Sarasota Bay and the Gulf waters beyond. Combining luxury updates, exceptional outdoor amenities, and a premier location within the coveted Bay Isles community, with private beach club access, this extraordinary Longboat Key residence presents a rare opportunity to enjoy refined waterfront living with every major improvement already completed.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY
SLEEPY LAGOON PARK - A4694601 - 523 JUAN ANASCO DR, LONGBOAT KEY, FL 34228 4 Days on yellowkey
$1,895,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
This beautifully reimagined John Cannon home, in the tranquil north end of Longboat Key, blends luxury with island living. The custom, Spanish-style design offers four bedrooms and a complete top-to-bottom renovation. New hurricane-rated windows and doors ensure safety, and two brand-new air conditioning units—still under warranty—keep you cool. A tankless water heater, just three years old, provides endless hot water. In the garage, there’s a Mitsubishi AC dehumidifier, and the roof was replaced in 2026, giving you peace of mind. The kitchen is fully outfitted with Wolf and Sub-Zero appliances, and every bathroom has been completely remodeled. You’ll find extra storage in the garage, and deeded beach access means the sand is just moments away. Beyond the home, the location is unbeatable. You’re right across from the island’s pristine white sand beaches and close to golf, tennis, and the Longboat Key Club. You’re also a short drive from Anna Maria’s restaurants and bars. And if you love the outdoors, you can paddleboard, boat, kayak, and enjoy the island’s abundant wildlife—all right at your doorstep. This home offers both elegance and adventure, all in one stunning package.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC
QUEENS HARBOUR - A4694532 - 3527 FAIR OAKS LN, LONGBOAT KEY, FL 34228 5 Days on yellowkey
$2,550,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar
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 is courtesy of: COLDWELL BANKER REALTY
ROBERT LENNOX - A4694502 - 6664 & 6660 & 6670 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228 6 Days on yellowkey
$18,500,000 | Single Family Home | 2 beds | 2.0 baths | 2 gar
This house is a part of a 5.5 Property and will be sold together as one parcel. The house can be used as a guest house, caretaker home or removed for development.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY
LONGBEACH VILLAGE - A4694059 - 791 BROADWAY ST, LONGBOAT KEY, FL 34228 7 Days on yellowkey
$1,625,000 | Single Family Home | 2 beds | 2.0 baths | 3 gar
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, the 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
COQUINA BEACH - O6408404 - 2945 PYRULA DR, LONGBOAT KEY, FL 34228 12 Days on yellowkey
$3,125,000 | Single Family Home | 5 beds | 5.0 baths | 3 gar
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 3,800 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
QUEENS HARBOUR - A4693553 - 3620 FAIR OAKS PL, LONGBOAT KEY, FL 34228 14 Days on yellowkey
$3,150,000 | Single Family Home | 3 beds | 5.5 baths | 2 gar
Come for a visit and you will want to stay and make it yours! Strategically set back from the road, and appropriately positioned on this oversized lot, to allow for an abundance of private waterfront splendor. The expansive paver patio, with oversized pool, spa, outdoor kitchen, and fully equipped pool bath make this the prime setting for endless entertainment and fun with family and friends. Bay views expand over the mangroves to the rookeries and night lights of the Key as you take in the setting sun over Buttonwood Harbor. Get your fishing pole and binoculars ready because enjoyment is an every day event from your dock watching the beautiful Florida feather-life soar thru the skies or dropping a line to hook a surprise catch! Love the boating life? Great- your private dock awaits mooring of its next floating occupant! Upon entry you will be greeted with a customized deco- entry door offset with etched glass above. Inside this spacious home you will find three en-suite bedrooms with a highly possible 4th en-suite in the loft space. The interior space offers marble floors thru-out the entire residence, including the striking marble staircase, and ceilings that reach to great heights allowing for transom windows and a wall of glass to incorporate natural lighting and this amazing view. Like cocktails and eating? A home hi-lite is the wet bar which can serve multiple purposes- bar, buffet, or even a desk, centrally positioned between kitchen, living, dining and family room areas so that no one is too far from that beloved bartender or the delectable fare! Love art? These walls were meant for displaying the finest of your collection. This is a fabulous floorplan with a very separated bedroom layout providing plenty of space for all to spread out and make themselves comfortable. Located in Bay Isles, this home offers guarded, gated access and also deeded access to the Bay Isles Beach Club.
SABAL COVE - A4693445 - 3344 SABAL COVE LN, LONGBOAT KEY, FL 34228 14 Days on yellowkey
$1,699,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar
Behind the gates of Bay Isles in the private enclave of Sabal Cove, this spacious waterfront residence offers an exceptional opportunity to enjoy the desired Longboat Key lifestyle. Ideally positioned within proximity to the renowned amenities of the Longboat Key Club, with membership, residents can enjoy world-class tennis facilities, 45 holes of golf, a clubhouse, private dining venues and access to a marina. From the moment you enter the home, you are greeted by spectacular layered views of the water and golf course. Expansive glass doors draw your eye across the pool and spa, over the tranquil inland lagoon and beyond to the lush fairways of the golf course. Soaring ceilings and generously scaled rooms create an airy sense of openness throughout, while the flexible floor plan offers endless possibilities for customization and modern living. The eat-in kitchen is ideally situated to capture the stunning views and opens seamlessly to the living area, creating an inviting space for entertaining and everyday living. A formal dining space is also adjacent to the living room for special occasions. The first-floor primary suite is a peaceful retreat featuring dual walk-in closets, custom built-ins and large sliding glass doors framing serene water vistas. There is a dedicated office with a built-in desk and bookshelves. Also on the main level is an additional en-suite guest bedroom with a bath that conveniently serves as a pool bath. Upstairs, two additional en-suite bedrooms have privacy for family and guests, including one bedroom with a private lanai overlooking the water. There is new wood flooring on the first floor (living room, dining, entryway) and new wall-to-wall carpet upstairs. Additional features include a circular driveway and a two-car garage. This home offers outstanding space, views, and location with excellent bones and tremendous potential for updating and renovation to create a spectacular coastal estate that expresses your personal style. Residents of Sabal Cove enjoy deeded access to the gated Bay Isles Beach Club, featuring dedicated parking, beach chair storage, restrooms, picnic tables, outdoor grills, kitchen facilities and more than five acres of pristine Gulf-front beach on Longboat Key. Living here, you'll make memories that last a lifetime.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY
LONGBOAT KEY ESTATES - A4692822 - 617 ROUNTREE DR, LONGBOAT KEY, FL 34228 15 Days on yellowkey
$2,495,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Premier waterfront opportunity in Longboat Key Estates, offering direct canal frontage in one of the island’s most desirable residential enclaves. Positioned along a quiet interior street, this property offers the opportunity to own or build a custom coastal residence in an area undergoing continued redevelopment and investment potential. Surrounding properties reflect the neighborhood's transformation, with new-construction homes setting a high standard for modern, exclusive waterfront living. The canal setting provides protected waters for boating with access to Sarasota Bay, while deeded, private beach access offers the rare combination of boating and beachside lifestyle. This property offers views of Sarasota Bay and the Intracoastal Waterway directly from your Lanai and dock, featuring a 100 feet of seawall frontage (2022) and a 16,000-pound boat lift (2022). Generous lot dimensions and a tranquil waterfront setting create an exceptional opportunity for boating enthusiasts and the ideal canvas for a thoughtfully designed custom residence. As a resident of Longboat Key Estates, a deed-restricted single-family waterfront community, you have deeded access to the Gulf and a private resident-only Tiki within a five-minute walk. Enjoy close proximity to Bayfront Park offering pickleball and tennis, kayaking, along within close distance to fine dining, St. Armands Circle, downtown Sarasota, Sarasota International Airport, and Florida’s Gulf Coast, all at your doorstep!
Listing is courtesy of: FINE PROPERTIES
TRITON COVE - A4692587 - 3040 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228 22 Days on yellowkey
$1,899,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar
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!
COUNTRY CLUB SHORES SEC 2 - A4692210 - 524 HORNBLOWER LN, LONGBOAT KEY, FL 34228 23 Days on yellowkey
$2,900,000 | Single Family Home | 3 beds | 3.5 baths | 3 gar
Tucked along one of the most sought-after canals in Country Club Shores, 524 Hornblower Lane is a waterfront residence that fully embodies the Longboat Key lifestyle, where boating access, beach proximity, and refined coastal living intersect with intention. Set on a 0.28-acre canal-front homesite with 107 feet of water frontage, the property offers what experienced boaters immediately recognize as premier water: wide, deep canals with quick, unobstructed access to Sarasota Bay and the Intracoastal. A composite dock, dual boat lifts accommodating vessels up to approximately 38 feet, and a dedicated jet ski lift create a true boating compound, designed for both serious use and effortless enjoyment. Behind its stately, columned façade, the residence spans over 3,000 square feet of living space, thoughtfully updated over time with an effective build year of 2005 and continued improvements, including impact-rated glass, a newer metal roof (2025), and recently replaced mechanical systems. The layout is both functional and flexible, with three bedrooms, three full baths, and a half bath arranged across a two-story design that balances everyday livability with elevated entertaining. The main living areas unfold with a coastal-modern sensibility, wood flooring, crown molding, and expansive sliders that frame views of the pool, lanai, and canal beyond. The kitchen, finished in a soft seafoam palette, blends custom shaker cabinetry, quartz surfaces, and professional-grade KitchenAid appliances with a dedicated beverage station, creating a space that feels equally suited for quiet mornings or hosting at scale. A standout feature of the home is its full entertainment space; an expansive theater and bar lounge designed as a destination in itself. With a projector system, surround sound, custom wet bar, and multiple gathering zones, it introduces a layer of lifestyle rarely found in properties of this scale. A cylindrical tube elevator provides a striking architectural moment while connecting this space directly to the private primary suite above. Upstairs, the primary suite is positioned to take full advantage of the waterfront setting, with a private balcony overlooking the canal, an oversized walk-in closet, and a spa-like bath complete with a jetted soaking tub, dual vanities, and a glass-enclosed shower with dual heads. Outdoors, the experience is equally intentional. A resort-style saltwater pool and spa anchor multiple seating and entertaining areas, complemented by an outdoor kitchen and low-maintenance landscaping that keeps the focus on the water. What elevates 524 Hornblower beyond its physical attributes is its location within the broader context of Longboat Key. Deeded beach access provides a direct connection to the Gulf, while proximity to St. Armand's Circle and the St. Regis Longboat Key Resort places world-class dining, shopping, and amenities just minutes away. The result is a rare dual lifestyle, boating on one side, beach on the other, anchored by one of the island’s most established and desirable neighborhoods. At its core, this is a property defined by access: to water, to the Gulf, to the lifestyle that has long made Longboat Key one of Florida’s most enduring coastal addresses.
Listing is courtesy of: DOUGLAS ELLIMAN