Homes for Sale Near Bayshore High in Longboat Key - 70 homes

Remarks: Gulfside Condo on north Longboat Key with direct beach access: This 2-bedroom, with bonus room, second floor condo offers the island lifestyle you've been searching for—a waterfront community, stunning sunset views from the lanai, and steps to the beach. Located in Longbeach Condo community on Longboat Key, this turnkey furnished, coastal Florida condo features 2 bedrooms, 2 bathrooms,and a bonus room currently used as a den. The comfortable floorplan features a bonus room for bunks, an office, or a reading room, a wide galley kitchen with Corian counters and tossed marble tile backsplash, in-unit washer/dryer, tile floors throughout, and a private balcony with views of the Gulf. At 19.5 foot base flood elevation, this unit was well above the storm surge of previous hurricanes. Longboat Key Living means beach access, world-class golf courses, world class tennis and waterfront dining just minutes away. The Longbeach Condo community offers 9.2 acres of gulf front, beach property, amenities like heated pool, club house, open parking, private beach access, kayak storage and private tennis. You're 15 minutes to St. Armands Circle shopping, 20 minutes to downtown Sarasota, and close to world-class fishing charters from Cortez Fishing Village. This barrier island property is perfect for full-time Florida living, a vacation home, a snowbird retreat or investment rental property. Rental history/projections available. The location puts you near Coquina Beach, Marina Jack, and easy access to Sarasota-Bradenton International Airport. Nationally ranked medical facilities located within minutes and all LBK first responders are EMTs!

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listing Agent: Diana Kryszak (941-993-4078)

Remarks: Pre-Construction. To be built. Build your dream waterfront home on North Longboat Key! Discover an exceptional opportunity to create your custom coastal retreat on this build-to-suit lot with 120 feet of waterfront frontage. The property is primed for development, with a permit filed and anticipated approval. Included in the price are complete architectural plans by Sweet Sparkman Architecture and Interiors, renowned for their innovative designs that harmonize modern luxury with beauty of Florida's coastal landscapes. The thoughtfully designed floor plan ensures a seamless flow for everyday living and entertaining, capturing breathtaking water views from key living areas. Whether you’re relaxing indoors or going out to enjoy the vibrant outdoor spaces, this home has been envisioned to maximize its unparalleled waterfront location. Key features include a new seawall in 2023 that provides a solid foundation for waterfront living. Deeded beach access, just a short distance away, offers private enjoyment of pristine sandy shores on Longboat Key. Boating enthusiasts will appreciate the ample frontage for a dock and boat, providing easy access to Sarasota Bay and beyond. On sought-after North Longboat Key, the property offers proximity to acclaimed restaurants like Shore, Whitney’s and Mar Vista, ensuring dining and entertainment are always nearby. This is your chance to bring a remarkable vision to life in one of Florida’s desired locations. Schedule your private showing today and imagine the possibilities.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Moriah Taliaferro (941-504-9910)

Remarks: Wow, Excellent New Price! Your opportunity to own a piece of Longboat Key paradise just got even better. The stunning Cali-Modern residence has a new, more attractive price! Presenting an amazing opportunity for this stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. Presenting a stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. This sophisticated, move-in ready home offers an abundance of good vibes and professional quality, available now on the highly sought-after North End of exclusive Longboat Key. Sleek, chic, and absolutely move-in ready, this property is an instant atmosphere setter. From the moment you step inside, you'll feel the coastal modern bliss. Enjoy the clean, modern lines, vaulted ceilings, and stunning stone tile floors, all bathed in gorgeous southern sun light. The upgraded kitchen and bathrooms sparkle with new features, complemented by new appliances. This home has been lovingly and extensively renovated, offering quality and style that goes well beyond the expected. You will find thoughtful design and premium features in every corner. Step outside to your own private backyard oasis, the perfect spot to sip a sunset cocktail. Fully fenced and private this oasis sets up perfectly for the future pool. And talk about location! You are literally steps from both Gulf and Bay access. This home boasts unbeatable walkability to island favorites like Harry's Deli and The Continental Kitchen, Euphymya Haye and the Hayloft, Lo-Key Island Grille, Cedars East Tennis and Fitness Resort and many others. The best-kept secret? A private back gate leads you directly into the 32 acres of Joan Durante Park, offering pure, natural Florida coastal hammock. This park is a true gem filled with nature walking trails, fishing piers, playground for the kids and multiple Bay access points (perfect for the kayak launch) No fuss, no stress. With a standing seam metal roof, Hardi board siding, newer double-pane windows, New interior, new appliances and offered fully furnished, this charmer is ready for your island life to begin immediately. Don't wait, come feel the charm for yourself!

Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)

Listing Agent: Jesse Griffin (941-822-6165)

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!

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Debby Mccaig (941-544-1713)

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)

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!

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Debby Mccaig (941-544-1713)

Remarks: SELLER SAYS “SELL!” Unbeatable opportunity at $649,900 for a full Bayfront Waterview, corner end-unit on Longboat Key. Exceptionally priced below market value—this residence represents the lowest-priced Bayfront end unit in the highly desirable community of Windward Bay, in over 5 years. A compelling price point, providing rare access for those seeking to own a premium waterfront residence at an extraordinary price. Encompassing 1,523 square feet, this stylishly furnished, two-bedroom, two-bath residence is thoughtfully designed to showcase uninterrupted panoramic Bay views from every room. Natural light fills the open living and dining areas, where expansive windows frame ever-changing Bay views from sunrise through the evening’s sunset. The remodeled 2024 kitchen opens seamlessly to the main living area and features recently completed upper cabinetry and a sophisticated yet functional layout ideal for both relaxed daily living and entertaining. Recently acquired “chic” French doors in both bedrooms open to the Florida Room, a signature feature for Longboat Key residences, offering additional living space to enjoy morning light and serene Bay vistas. The spacious primary suite includes a private en-suite bath and a generous walk-in closet, providing comfort, supporting everyday living, and abundant storage. “Pet Friendly” Windward Bay is a well-established waterfront community known for its mature landscaping, waterfront setting, resort-style amenities, a strong proactive association with solid reserves, and an enduring reputation as one of Longboat Key’s most welcoming communities. (Attributes that continue to attract owners who value lifestyle as much as long-term stability.) The Milestone Inspection and Capital Reserve Study are complete. Windward Bay’s Monthly Condo Fees for 2025 were actually reduced and for 2026 only increased slightly by $13 a month, demonstrating a financially healthy Condo Association. Offered furnished and move-in ready, this corner end-unit provides flexibility as a full-time residence, seasonal retreat, or investment opportunity. 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, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. An uncommon offering distinguished by exceptional value, location, and the timeless appeal of gulf to bay living. Private showings are available for those seeking a rare chance to own a premium waterfront residence at an extraordinary price.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Debby Mccaig (941-544-1713)

Remarks: Under contract-accepting backup offers. Gulf front Masterpiece with Bayside Boathouse and 12klb lift Experience the pinnacle of coastal living at this unparalleled Gulf-to-Bay estate on Longboat Key, where 100 feet of private, sugar-white beachfront meets the rare luxury of a deeded bayside boathouse—a coveted feature seldom available on the island. For the discerning boater, this exceptional amenity includes a 12,000-lb lift and upgraded dockage on tranquil Sarasota Bay, allowing seamless access to open water adventures while preserving the serenity of Gulf-front living. Architecturally envisioned by Clifford M. Scholz and brought to life by Perrone Construction, the residence is a timeless fusion of coastal elegance and enduring craftsmanship. Elevated concrete block construction, a newly installed metal roof, and impact-rated windows ensure peace of mind, while expansive verandas and elevated terraces provide panoramic views of the Gulf, Bay, and captivating sunsets. Spanning three levels with elevator access from garage to top-level owner’s suite, the home’s interior is equally refined 4BR/4,224sf (7,758sf total) - anchored by a gourmet kitchen with Sub-Zero, Viking, and Neff appointments, and graced with fluid indoor-outdoor spaces designed for both grand-scale entertaining and quiet personal retreats. The primary suite is a sanctuary unto itself, featuring dual walk-in closets, spa-inspired bath, and breathtaking views of the Gulf from its private balcony. The ground level offers over 2,600 sq ft of flex space, ideal for a collector’s garage, home gym, or additional guest accommodations. Outdoors, the Gulf-front pool deck with summer kitchen invites year-round al fresco living, while a private path leads directly to one of Florida’s most pristine beaches. Perfectly positioned on North Longboat Key - near Anna Maria Island, St. Armands Circle, and downtown Sarasota, this rare estate offers absolute privacy without sacrificing access to the region’s finest dining, shopping, and cultural experiences. This is not simply a beachfront home—it is an irreplaceable legacy property offering the best of both Gulf-front tranquility and Bayfront boating. Private showings by appointment only for qualified buyers.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listing Agent: Steve Walter (941-809-0907)

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. 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 is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Nicholle Mckiernan (941-928-2922)

Remarks: Rarely Available at Longboat Landing! This 3-bedroom, 2-bath second-floor condo offers the ultimate in coastal living with only 9 total units/owners in the entire community—providing privacy, exclusivity, and a boutique feel. Enjoy full Sarasota Bay views from your living room, with the added peace of mind of being on the second floor (no flood concerns). Inside, you’ll find engineered hardwood floors, a granite countertop kitchen, and hurricane impact windows that fill the space with light and frame the water beyond. The spacious primary suite offers a private retreat, while two additional bedrooms provide room for guests, a home office, or flex space. Outside, embrace the Longboat Key lifestyle with a boat dock slip, fishing pier, and community amenities designed for waterfront enjoyment. Perfectly located on Gulf of Mexico Drive, just minutes from island dining, boutique shopping, and the world-renowned beaches of Longboat Key. Rarely available. Bayfront views. Exclusive 9-owner community. This one is not to be missed!

Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)

Listing Agent: Schuyler Burke (907-223-8161)

Remarks: This is the one you have been waiting for!! INCREDIBLE UNOBSTRUCTED BAY VIEWS & BREATHTAKING SUNRISES from this light-filled CORNER unit in the beach-to-bay community of Sutton Place. Enjoy stunning vistas from nearly every room through impact windows and doors! Meticulously maintained and beautifully renovated, this spacious two-bedroom, two-bath coastal retreat is truly exceptional. The thoughtfully designed open concept chef’s kitchen with premium cabinetry, plentiful storage, and Cambria quartz countertops seamlessly connects to the expansive living area through a custom dining island with wraparound seating. Plantation shutters throughout the kitchen and living area add to the coastal island feel. The enclosed lanai, featuring walls of glass that span along the rear of the unit, provides an ideal setting for morning coffee, evening relaxation, remote work, or accommodating additional guests. The spacious primary and secondary bedrooms provide exceptional views, each with direct access to the lanai through impact-rated sliding doors. The serene primary bedroom boasts a generous walk-in closet fitted with a custom organizer and an elegantly renovated bathroom with a walk-in shower, complete with a linen closet. The secondary bedroom offers ample storage with a double closet, also fitted with custom organizers. The adjacent guest bath has been tastefully renovated. Parking is easy with a covered, assigned space in a convenient location, plus plenty of overflow and guest parking. While the stairs are easily accessible; there is also an elevator for added convenience. The in-building storage unit provides extra space for any additional storage needs. Sutton Place offers a wide range of amenities, including two heated swimming pools, a community clubhouse, marina facilities with boat slips (current wait list but only $300 annually!!), kayak storage equipped with electric launch, a fish cleaning station, designated grilling areas, car wash stations, and deeded beach access with private beach pavilion featuring storage lockers, showers, and restrooms. The community successfully endured the recent storms, experiencing minimal overall damage and no impact to any individual units. With its exceptional location, unmatched views, and wonderful amenities, this property is an opportunity not to be missed! Schedule your private showing today!

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: Melissa Rodocker (703-969-2345)

Remarks: Significant Price Reduction on this NEW in 2024, dream retreat that is uniquely positioned in the highly sought after “Village” of Longboat Key, a neighborhood known for its quaint charm and vibrant community atmosphere. Featuring 4 bedrooms and 4 and a half baths in open and light filled rooms, a backyard oasis with a pool and outdoor kitchen, high impact windows and doors throughout, 1230 sq ft of porches and balconies and an amazing rooftop top deck with spectacular water views: this is truly the epitome of luxury island living! The stunning chefs kitchen features high end appliances, including a 6 burner gas range, double ovens and a large center island. A perfect open flow into the inviting dining and living area, allows for exceptional entertaining with picturesque views out to the backyard oasis, seamlessly connecting indoor and outdoor spaces. This rare offering of NEW construction in this wonderful neighborhood is hard to come by. It affords its owner peace of mind, whether this is your forever home, your part time vacation retreat or a fabulous investment rental property. The community features multiple restaurants, a couple of Bayfront docks and even a community boat ramp. The gorgeous Gulf of Mexico is within a short walk, bike or golf cart ride away and is one of the nicest beaches on the island. It stretches for miles and is the perfect spot to spend the day before returning to watch the sunset from your rooftop deck. Come savoir the laid back island lifestyle that Longboat Key is known for and make this tranquil coastal retreat your own.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listing Agent: Jodene Moneuse, Pa (941-302-4913)

Remarks: $100,000 PRICE REDUCTION!!! Live the ultimate Florida Waterfront lifestyle in this private, calm, secure, spacious and elegant large elevated coastal home. Located on the North end of Longboat Key less than a mile to Anna Maria Island in the relaxed Sleepy Lagoon neighborhood with deeded beach access just around the corner, leading you to never crowded stretches of sand. The home is located on a boating canal just three houses in from the bay offering direct access to Sarasota Bay and the Intercoastal Waterway. This large ( 5328 SF total) very well maintained and upgraded elevated home offers 2800 SF on the main living level plus 2500 SF of bonus space on the first floor with an elevator. This elevated, well-built custom home sustained no damage nor have any flood claims ever been filed. This home spans two level of living and has an open floor plan, blending indoor and outdoor living. The main living area is upstairs with large flowing open rooms, vaulted ceilings, a fireplace and features French Doors leading to a screened Lanai overlooking the natural canal with foliage for privacy. The bedrooms are arranged in a split plan with each having en-suite bathrooms with lots of closets and built-ins. The large eat-in kitchen has custom cabinetry with crown molding, pull-outs, granite countertops and stainless appliances plus a large separate dining room perfect for all your family or friends. Just off the kitchen on the main living level is a very large laundry room along with all the closets in this home you will have all the storage you need. On the first level is the open foyer leading up to the living area with the elevator access and oversized split garages. There is an additional 2500 SF of AC/heated of interior space that is finished with polished concrete floors and walls of sliding doors leading to the pool area, porch, deck, yard and dock area. Also just outside your bonus space is private 60’ long screened, heated lap pool with a full bath. The property would provide great renal income also for a part time owner as it has in the past. Walk the beach, swim in the pool or ocean, ride your bike on the Longboat Key Bike path, fish, boat, kayak, paddle board, jet ski and enjoy your spacious home that is just a short drive to Sarasota, St. Armand’s circle and Anna Maria Island. Please see the videos. What are you waiting for? Start living the dream.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listing Agent: Marta Altizer (941-383-7591)

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)

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.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)

Listing Agent: Cindy Fischer (941-465-1124)

Remarks: Enjoy the best of the Longboat Key lifestyle in this beautifully updated 2-bedroom, 2-bath waterfront condo at Sutton Place, offering a rare Gulf-to-Bay experience with Sarasota Bay views and PRIVATE DEEDED BEACH ACCESS to a Gulf-front beach just across the street. This light and bright residence features a spacious, open floor plan with quality finishes throughout, including porcelain tile and engineered hardwood flooring for a clean, modern, low-maintenance feel. The updated kitchen is both stylish and functional, showcasing quartz countertops, a mother-of-pearl mosaic backsplash, tray ceiling, and stainless steel appliances. The primary suite includes a fully remodeled bathroom with quartz counters, custom glass shower, and marble tile, while the guest bathroom features granite countertops and a vessel sink. A glass-enclosed and screened lanai extends the living space, bringing in natural light and allowing you to enjoy peaceful bay breezes year-round. Recent upgrades include newly installed IMPACT RESISTANT WINDOWS & DOORS, providing added safety, energy efficiency, and peace of mind. Updated lighting was also added in the living area This residence is being sold TURNKEY FURNISHED, making it truly move-in ready or ideal as a second home or investment property. As an added bonus, the sale includes four brand new KAYAKS—perfect for enjoying the community’s direct bay access and embracing the waterfront lifestyle. Sutton Place is a highly desirable waterfront community offering exceptional amenities, including deeded Gulf beach access with pavilion, gated parking, showers, and picnic areas, TWO heated bayside POOLS, BBQ grills, BOAT SLIPS (first-come, $300/year), kayak storage and launch, fishing dock, clubhouse, and covered parking with ample guest spaces. The community is pet-friendly (2 pets up to 25 lbs each), not age restricted, and allows two rentals per year with a one-month minimum after the first year of ownership, making it ideal for both personal use and investment. Recent community improvements include new roofs, exterior repainting, and resealing (2023), along with a completed milestone inspection. Ideally located mid-key, close to Bayfront Park, dining, shopping, and just a short drive to Anna Maria Island, St. Armands Circle, and downtown Sarasota. Don’t miss this opportunity to own a piece of paradise on Longboat Key.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Debbie Mchardy (941-960-6099)

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 is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Marcela Terrell (941-929-3010)

Remarks: One or more photo(s) has been virtually staged. Welcome to 550 De Narvaez Drive, a meticulously maintained WATERFRONT residence set on an ELEVATED 10,000 sq. ft. lot in the highly desirable Sleepy Lagoon neighborhood on the NORTH END of Longboat Key. This solid concrete block home has experienced NO FLOODING & NO STORM DAMAGE, offering exceptional peace of mind. Spanning 1,758 sq. ft., the light-filled interior features 3 SPACIOUS BEDROOMS and 2 beautifully RENOVATED BATHS. Generous room sizes, abundant natural light, and an inviting floor plan create a true sense of warmth throughout the home. The UPDATED KITCHEN and baths showcase contemporary finishes while maintaining comfort and functionality. Enjoy peaceful CANAL VIEWS with direct access to Sarasota Bay—perfect for boating enthusiasts and embracing the ultimate Florida waterfront lifestyle. NEW DOUBLE PANE IMPACT-RESISTANT WINDOWS and sliding glass doors provide enhanced protection and energy efficiency. Additional upgrades include NEWLY LINED PLUMBING PIPES and UPGRADED ATTIC INSULATION for lasting durability and comfort. Offered FULLY FURNISHED, all furnishings convey with the sale—making this a true TURNKEY opportunity. Simply bring your suitcase and start enjoying coastal living immediately. The expansive elevated lot offers ample space for outdoor entertaining, gardening, or FUTURE EXPANSION POTENTIAL. Ideally located near world-renown Gulf beaches with DEEDED BEACH ACCESS, exclusive dining, boutique shopping, and recreational amenities, this exceptional property is well-suited as a primary residence, seasonal retreat, or investment opportunity. Schedule your private showing today and experience refined, worry-free waterfront living at its finest.

Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)

Listing Agent: Dean Hinterstoisser (941-726-0314)

Remarks: Welcome to elevated beachfront living in highly desirable Windward Bay — a premier bayside enclave offering serene coastal charm and resort-style amenities on picturesque Sarasota Bay. This fully reimagined 2-bedroom, 2-bath villa has been thoughtfully renovated from top to bottom with impeccable attention to detail and contemporary finishes throughout. Step inside to discover an open, light-filled interior featuring brand-new electrical and plumbing systems, new drywall and insulation, new kitchen and bathrooms — everything crafted for modern comfort and peace of mind. A dedicated 220-volt receptacle makes electric vehicle charging effortless, blending convenience with conscientious living. Enjoy easy walk-in access with no stairs, and take full advantage of Windward Bay’s pet-friendly policy — perfect for up to two pets — making this the ideal coastal retreat for the whole family. Relax and unwind on your private back patio overlooking lush landscaping, where tranquil sunsets frame the entrance to the beach access just steps away. Cozy evenings by the fire pit become part of your daily rhythm. Windward Bay is cherished for its park-like grounds, complete with: Nearly a half-mile of scenic walking trails. Three distinct Gulf beach access points. Two heated pools. Six pickleball/tennis courts. A well-appointed clubhouse with fitness center, sauna, library, and meeting spaces. Two marinas with boat and jet ski slips. A private fishing pier. Outdoor grilling areas, firepits, and kayak storage. This exceptional villa effortlessly combines the ease of turn-key living with premium upgrades and unparalleled community amenities — all in one of Longboat Key’s most sought-after waterfront communities.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)

Listing Agent: Sharon Austin (678-756-4020)

Remarks: WOW, A SECOND Early Price Drop. Motivated seller, Priced for immediate sale on this fully renovated and furnished Village of Longboat Key Home. Take Advantage Today. Coastal Elegance Meets Island Ease in Longboat Key's Coveted Village. Discover a sanctuary of sophistication at the exclusive North Tip of Longboat Key. Located in the heart of historic Long Beach Village, this is more than a home; it's the ultimate island lifestyle, delivered. Just a short, serene stroll separates you from the pristine beach and the island's best waterside dining. This property has been meticulously and fully remodeled, representing a rare "move-in ready" opportunity where every detail has been elevated. From top to bottom, inside and out, virtually nothing has been untouched. A Home Designed for Seamless Living: Open Concept: Step into an airy, open-plan great room, anchored by a brand-new kitchen - perfect for hosting intimate gatherings or unwinding after a day on the water. Chef's Delight: The remodeled kitchen is a masterpiece featuring stunning marble countertops, custom cabinetry, all-new luxury appliances (including a mini wine refrigerator), and a chic island/bar. High-End Finishes: Enjoy the cohesive flow of new luxury vinyl plank flooring throughout every room, complemented by fresh, designer-selected interior paint. Peace of Mind: Recently installed, all new windows and sliding glass doors are Miami-Dade impact resistant, offering superior protection and efficiency. Also a brand new architectural three-tab shingle roof was just installed. Your Private Island Retreat: Spa-Inspired Baths: Both the master and second bathrooms have been fully renovated with premium stone shower flooring, elegant new tiles, and updated fixtures. Outdoor Oasis: Off the master suite, a new impact-resistant glass door opens to a spacious, private backyard. The highlight is the expansive, screened-in porch that wraps around the back of the house, overlooking a charming outdoor fire pit and grilling area. Beach Ready: An exterior shower and dedicated storage for your gear make rinsing off after a day at the beach effortless. The Village Lifestyle: To know The Village is to fall in love with its relaxed, yet refined rhythm. This community places everything you desire at your fingertips: secluded walking trails, Bay access, community docks, and the island's best beach access. The Village is one of the few places on Longboat Key where the golf cart isn't just legal, it's the preferred, fun, and convenient way to live. This is your unique chance to maximize a truly effortless, luxury island lifestyle. Come and see it today. * Seller has been averaging $55k Gross on seasonal rental.

Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)

Listing Agent: Jesse Griffin (941-822-6165)