Homes for Sale Near Bayshore High in Longboat Key - 87 homes

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: 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)

Remarks: Rare Turn-Key Gem in Cedars East | Proven $55k+ Annual Income! Experience the ultimate in coastal luxury and investment savvy in this stunning, fully furnished 3-level retreat. Nestled within the lush, sought-after Cedars East community, this 2-bedroom, 2-bathroom home is a proven performer, having generated over $55,000 in short-term rental income in 2025 alone. Whether you are looking for a lucrative addition to your portfolio or a seamless move into your dream primary residence, this property is truly "turn-key"—every piece of stylish furniture and essential household item is included. Simply bring your suitcase and start living the Longboat Key lifestyle from day one. The thoughtful layout begins with an oversized attached garage on the first floor, providing ample space for vehicles and beach gear. Ascend to the second level to find an entertainer's dream: an expansive open-concept kitchen featuring sleek bamboo cabinetry, convenient pull-out drawers, and a central cooking island with bar seating. The living and dining areas flow effortlessly from the kitchen, anchored by a unique illuminated feature wall that adds a touch of modern sophistication. On the third floor, privacy and views take center stage. The primary suite serves as a serene sanctuary overlooking tranquil wooded vistas, while the front guest bedroom offers picturesque views of the sparkling community pool. Beyond your front door, Cedars East offers a resort experience without the extra membership fees. Spend your days lounging by the Junior Olympic-sized pool, strolling the scenic boardwalks through the mangroves, or casting a line off the bayside fishing pier. For the active resident, the world-class Cedars East Tennis Club is just steps away, featuring 10 Har-Tru courts and professional instruction. You are perfectly positioned just minutes from the pristine sands of Longboat Key, the upscale shopping of St. Armand’s Circle, and the cultural heartbeat of Sarasota, including the Ringling Museum and Mote Marine.

Listing is courtesy of: REDFIN CORPORATION (617-458-2883)

Listing Agent: Marcia Van Ginhoven (704-497-0664)

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: 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: Public showings are now available for the first time on 5/2/2026. After months of restricted access due to a tenant, this residence is finally available for public showings. Restricted access resulted in only a handful of private showings, giving today’s buyers a rare chance to discover a home that’s been under the radar. 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: 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: "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. 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. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”

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

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

Remarks: Paradise at Harbour Villa Club – Waterfront Luxury with a boat slip on Longboat Key! Enjoy this condo year round, or rent it weekly when you cannot be there- you choose! Discover this fully renovated 2BR/2BA condo with panoramic views of the gorgeous Sarasota Bay. Bright and spacious, the open floor plan features soaring 9 ft ceilings, custom finishes, a gourmet kitchen with top-of-the-line appliances and a sleek wet bar. The primary suite offers stunning water views, dual closets, and a spa-inspired bath. The second bedroom is spacious and set apart from the primary. Step into the enclosed lanai for breathtaking 180° water views and added living space— perfect for relaxing or entertaining. This unit comes with a deeded 40' boat slip #3 which features upgraded power and plumbing, new wraps, caps, marine grade bumpers and a deck box- a rare bonus that can accommodate a 55' vessel! Harbour Villa Club is nestled in a quiet corner and you can walk or bike to the beach, area restaurants, and beloved Harry's Corner Store. This is a pet friendly community with covered parking, storage, elevators, kayak and bike storage, private dock, heated pool, tennis/pickleball courts, grills and beautiful landscaping. Weekly rentals allowed. Call today!

Listing is courtesy of: CENTURY 21 BILL NYE REALTY (813-782-5506)

Listing Agent: Lori Lahart (813-297-9610)

Remarks: An incredible opportunity to purchase a canal front home on a 10,000 sf lot with 100 feet on the waterfront! Priced for you to bring your vision and remodel or tear it down and build your dream island getaway on the fabulous North end of Longboat Key. A short walk or bike ride to the neighborhood beach access and with no high rises on this end of the island, some days it feels like its privately yours! The home is on a nicely elevated lot and suffered only minimal water intrusion in the storms from 2 years ago. As new multi million dollar homes are going up everywhere, don't miss your chance to get this one at lot value!

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

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

Remarks: New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—competitively priced and move-in ready. Nestled along a private canal, this 4-bedroom plus den, 4,106 sq ft residence blends contemporary sophistication with coastal appeal. Designed for effortless indoor-outdoor living, the home boasts two spacious lanais, a private pool and spa, and an elevated foundation at 9.5 feet for added peace of mind. Boaters will enjoy concrete canal bulkhead with quick access to the Gulf of Mexico, perfect for endless days on the water. Inside, the home features engineered hardwood flooring, sleek quartz countertops throughout, a large walk-in pantry, and the convenience of dual laundry rooms. Set in a tranquil, private location just minutes from Longboat Key’s renowned beaches, golf courses, and upscale dining, this home is a rare gem. Don’t miss your opportunity to own a waterfront retreat in one of Florida’s most sought-after coastal communities.

Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)

Listing Agent: Joshua Freed (941-577-5121)

Remarks: A Gulf-Front Masterpiece on Longboat Key! This stunning Gulf-front estate is perfectly placed on nearly an acre of pristine Gulf-front property along the shoreline on Longboat Key. With direct Gulf frontage, this architectural masterpiece offers more than 6,900 square feet of refined interiors and panoramic views that stretch endlessly across the Gulf of Mexico. Designed for both privacy and grand-scale entertaining, the residence balances timeless craftsmanship with recent enhancements including a 2025 primary bath remodel, newer French doors, and resort-style pool and spa with natural gas heating and fire pit. From the moment you arrive through the circular drive, the home’s elegant façade, manicured landscaping, and elevated design make a commanding first impression. Inside, expansive living areas are defined by travertine and hardwood flooring, soaring coffered ceilings, crown molding, and walls of glass framing breathtaking views. The open floor plan flows effortlessly from the formal living and dining rooms to the family room and gourmet kitchen, designed for effortless entertaining. The chef’s kitchen showcases custom wood cabinetry, granite counters, a large island, high-end appliances, double ovens, and a breakfast nook overlooking the Gulf. The main-floor primary suite offers a serene retreat with direct beach views, its own private terrace, dual walk-in closets, and a spa-like new bath featuring dual vanities, stone counters, and a freestanding soaking tub. A private elevator connects all levels, including a versatile second-story loft, media room, and four additional bedrooms (some en-suite) providing ample comfort for family and guests. The outdoor living space defines Florida luxury—complete with an expansive travertine deck, heated pool and spa, summer kitchen, and multiple covered terraces designed for dining and relaxation. Enjoy vibrant sunsets over the Gulf from nearly every vantage point. The property also features new hurricane-rated French doors, a whole-house generator with raised platform, and a three-car side-entry garage with guest parking. Located on the prestigious north end of Longboat Key, this gated estate offers the perfect balance of seclusion and accessibility. Stroll along miles of private beach or take a short drive to the Longboat Key Club, offering championship golf, tennis, and fine dining. Just minutes away, St. Armands Circle and downtown Sarasota offer a vibrant mix of boutique shopping, art galleries, and acclaimed restaurants. With world-class marinas, cultural landmarks, and pristine beaches within reach, this exceptional residence captures the very best of Sarasota’s luxury coastal lifestyle. Offering an unparalleled combination of design, craftsmanship, and Gulf-front serenity, 6001 Gulf of Mexico Drive stands as a statement of timeless coastal elegance—where every sunset feels like home.

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

Listing Agent: Roger Pettingell (941-387-1840)

Remarks: NEW PRICE, AMAZING OPPORTUNITY!!! Experience the ultimate island lifestyle in this masterfully renovated 2,880 sqft, 4 Bed/3 Bath "lock-and-leave" condo at Cedars Tennis Resort and Club. Elevated sanctuary on the tranquil north end of Longboat Key. Offering the expansive feel of a single-family residence with the effortless "lock-and-leave" ease of being in the beautiful condo community of Cedars Tennis Resort and Club. This exquisite 4BR/3BA retreat defines coastal chic. A private elevator serves all three levels, opening into a sun-drenched great room with soaring ceilings, a fireplace, and a gourmet kitchen featuring dual islands and designer finishes. The refined dining room opens right off of this space with its custom built-in cabinetry and dry bar, ideal for any social gathering. Relax on your private, screened lanais overlooking lush tropical foliage and serene ponds, with peek-a-boo views of the Gulf. There is one on each living level. Rounding out the main living area is a versatile den/office (currently used as the 4th bedroom), a full third bathroom, beautiful hardwood floors throughout and a dedicated laundry room. The primary suite is a true oasis with a spa-inspired sunken bath, large walk-in shower, dual vanities and walk-in closets. Upstairs beyond the oasis of a primary there are two additional oversized guest bedrooms and a beautifully renovated guest bathroom with a walk-in shower. Recent updates beyond the full interior renovation include 2026 garage door replacements, and 2024 roof and AC replacement. Hardi- Board siding on exterior and Pella high-impact windows. The split 3-car garage provides total peace of mind and the rare abundance of space and storage. Nestled in the 66-acre village-like townhome community enveloped by nature, providing effortless access to both the beach and the bay on the beautiful north end of Longboat Key. The spacious and tropical community features lit boardwalks winding through mangroves, leading to an array of exceptional amenities including a heated Jr. Olympic Size Pool, nine Har-Tru Tennis Courts, three Pickleball courts, a Clubhouse with a Pro-Shop, a 24-hour Fitness Center, a Tiki bar, a restaurant, a fishing pier, and a kayak launch. Please note that some amenities require an additional club membership. The property is within walking distance to a variety of local attractions, such as Harry's Deli & Continental Kitchen, the true island gem that is Joan Durante Park, Euphemia Haye Restaurant & The Haye Loft, and, of course, Longboat Key's globally renowned sugary white sand beaches. Furthermore, it offers convenient proximity to other major attractions and cultural venues, including St. Armand's Circle, Mote Aquarium, the Asolo Repertory Theatre, Van Zel Performing Arts Center, Marie Selby Gardens, Anna Maria Island, the Ringling Museum complex, and numerous dining options on Longboat Key and in downtown Sarasota. Cedars East is the rare community on LBK that offers shorter-term rental allowance with its 2-week minimum, making it the perfect balance for offsetting costs when not in use, without living in a hotel community. Exceptional onsite management is in place if desired. Fantastic residence, rare opportunity, come take a look today!

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

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

Remarks: Experience the ultimate Bay-to-Beach lifestyle in this turnkey 2-bedroom, 2-bath condo at Longboat Harbour, where nearly every room offers sparkling water views and a sense of calm that only waterfront living can bring. Perfect for investors or seasonal residents, this home combines desirable updates with a lifestyle that’s hard to beat. Fully updated in 2025, this home blends modern luxury with coastal charm. LVP flooring, textured ceilings, and fresh paint flow throughout, while the brand-new kitchen boasts with all-white cabinetry, coffee bar, coastal glass backsplash, and quartz countertops. The master suite features custom closet doors, a new porcelain shower with frameless glass, porcelain flooring, and a quartz-top vanity with Bosch washer/dryer in the bath. The hall bath includes a new porcelain shower/tub combo, stylish vanity with quartz countertops, and contemporary Euroflush toilets. Every detail is designed to make the interior as inviting as the stunning views outside. Every update you could hope for in a ready-to-enjoy condo! Step outside and enjoy the resort-style amenities of a vibrant waterfront community. Longboat Harbour offers four heated pools, tennis and pickleball courts, a recreation hall, billiards, game rooms, docks with sailboat access (no bridges to the bay), and a fitness center. Social committee events, on-site grills, and beautiful landscaping surround you at every turn. For beach lovers, the private deeded beach access at 4415 Gulf of Mexico includes a beach house with restrooms, showers, and reserved parking. A short drive from Longboat Key, St. Armands Circle, and downtown Sarasota, you’ll find boutique shops, delightful dining, arts, festivals, and the wonder of Selby Botanical Gardens. Watch Gulf sunsets paint the sky while manatees, ospreys, and egrets play in the waters below… this condo is all about a life of fun, relaxation, and unforgettable moments.

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

Listing Agent: Ryan Skrzypkowski (941-328-8307)

Remarks: Under contract-accepting backup offers. 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: Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900 square feet, the open-concept layout showcases a chef’s kitchen with an oversized quartz island, premium appliances, and generous counter space ideal for entertaining family and friends. Light-filled second-level living and dining spaces open to an expansive porch and outdoor dining space , creating a seamless indoor-outdoor flow. The first living level features a serene primary suite with a spa-inspired bath and private balcony, offering a peaceful retreat. Upstairs guest suites provide privacy and comfort, with terraces to capture the island’s cooling breezes and glowing Gulf sunsets. A stunning rooftop deck with jacuzzi crowns the home, creating an unforgettable setting for evening relaxation or gatherings under the stars. Additional highlights include impact-rated windows and doors, elevator ready, and a two-car garage with ample storage. The award-winning Conrad Beach community offers a recently renovated resort-style pool with bath facilities and beautifully maintained landscaping, all just a short stroll from the shoreline. Enjoy the vibrant charm of nearby Anna Maria Island, Longbeach Village dining, marinas, and boutique shopping at St. Armands Circle and Sarasota. This home blends coastal sophistication, privacy, and comfort—an ideal winter haven to share with family and friends.

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

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

Remarks: This must-see hidden gem on the north end of Longboat Key offers a quintessential Florida lifestyle. Waterview’s galore as you walk into your newly completed, renovated Florida paradise home, on a deepwater marina and canal, which epitomizes beauty and style. Boat lovers will want the location of this totally turnkey furnished 1,423-square-foot standalone two-bedroom, two-bath home, with your upgraded composite boat dock just 15 feet behind your villa. Completely remodeled, this home provides contemporary classic design features that create an open airy gorgeous living space. All new stainless appliances in 2026, air-conditioner 2025, roof 2019 and more. The open kitchen design with a large island, new quartz countertops, plenty of beautiful new cabinets with roll-out drawers and a contrasting white and gray classic color scheme. Great counter space makes the kitchen ideal for entertaining and enjoying the coastal casual lifestyle. Beautiful porcelain tile flows throughout the home, providing continuity from room to room. An oversized skylight in the great room with retractable shade provides lots of extra natural brightness. The large primary bedroom is complete with a fully refashioned en-suite bath with gorgeous granite countertops and custom-tiled shower. A spacious walk-in closet provides plenty of room for your coastal style wardrobe. The second bath mimics the maintained class and elegance of this home with granite counters and tiled shower. The lanai has been transformed into extra living space with a cozy study and separate office nook. The study is an ideal spot to curl up with a book or just sit privately and watch the beautiful white pelicans float by with dolphins and manatees alongside. This flexplace can also house extra sleepover guests. The double lanai facing the water allows a panoramic view and full access to your large, elevated brick paver patio and dock from floor-to-ceiling, impact-grade patio doors. Go outside to a private oasis that overlooks the wide-open canal, marina and bay views. Sit, dine, entertain or sunbathe while you enjoy the abundant wildlife from the comfort of your patio paradise, or hop in your boat secured to your 5-by-25-foot dock and head out to one of the many Longboat Key restaurants. Some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico. Impact windows and new hurricane-rated doors throughout. The Spanish Main maintenance-free community has a wonderful neighborhood feel with heated pool, deeded beach access, a 40-foot slip marina with social events galore, making every day feel like a vacation as you lounge in the sun poolside and enjoy the sea The deeded beach access is ideal for those numerous beach days and magnificent sunsets. Pet-friendly, maintenance-free, and an active 55-plus community are added benefits for your enjoyment. Only a short drive to fantastic shops and restaurants, including Anna Maria Island, plus cultural events Sarasota and St. Armands Circle have to offer. This villa has been fully renovated in compliance with FEMA standards due to hurricane flooding in 2024.

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

Listing Agent: Kimberly Freiwald (941-256-6775)

Remarks: Wow! Panoramic water views from almost every window, plus rare direct access to Bay waters just near the back paver patio. This completely renovated two-bedroom, two-bath, 1,449-square-foot home is a must see! Fully remodeled in 2025/2026 in full compliance with FEMA requirements. It is all about details as this gorgeous Spanish Main turnkey furnished villa is ready to welcome you home! The centerpiece of the kitchen is the large, strategically custom-designed quartz island that doubles as a dining table, in a soft color palette that can seat 10. The kitchen features beautiful all wood 42-inch cabinetry, stainless steel appliances, large undermount sink with a push-button garbage disposal, lovely backsplash and lots of storage with an abundance of additional counter space, ideally designed for entertaining. The villa flows seamlessly with an expansive open floor plan, plank tile flooring in every room plus crown molding that frames each room. The large primary bath has an oversized, classically designed walk-in shower created for handicap access with double sinks. The tastefully appointed guest bath has an all-glass enclosed walk-in shower. From guest bath, enter the 9-by-6-foot in villa laundry room with new Electrolux washer and dryer. All hurricane-grade windows and doors to secure the home from the Florida storms. Custom window shades provide sun mitigation and ultimate privacy. The fully enclosed glass Florida room is a treasure in and of itself with extensive views of Sarasota Bay, with a lush backdrop providing total privacy. There is also a built-in office space, large walk-in closet, additional flex space for dining and/or lounging plus a dry bar and wine center, which makes this a useful space. Go outside onto the brick paver patio and lounge, grill and relax with the sound and views of Bay waters and abundant bird and wildlife. Grab your kayak or paddleboard and launch right from the backyard with direct water access to the open Bay waters. This villa is packed with so many upgraded features with new tile roof in 2019, air conditioner in 2020 and tankless hot water in 2018. The villa is part of the Spanish Main Yacht Club community, which has some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico, with restaurants you can get to by boat. The Spanish Main maintenance-free community has a wonderful neighborhood feel with a heated pool overlooking the 40-slip marina, deeded beach access, with social events galore making every day feel like a vacation as you lounge in the sun and enjoy the sea breeze. Slips are available for affordable leasing. Beach access is ideal for those numerous beach days and magnificent sunsets. This pet-friendly very active 55-plus community are added benefits for your enjoyment. Only a short drive to the fantastic shops and restaurants including Anna Maria Island plus cultural events Sarasota and St. Armands Circle have to offer. Private second-deeded parking place with this villa.

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

Listing Agent: Kimberly Freiwald (941-256-6775)

Remarks: Stunning full bay views as you enter this jaw-dropping magnificent, completely custom renovated stand-alone villa on Sarasota Bay. Professionally designed starting with an 18-by-11-foot gourmet kitchen. With 10-12-foot wood beam ceilings, a beautiful 12-foot quartz island that seats 10-plus people, solid wood cabinetry, Café’ brand double oven, refrigerator with two additional drawers, stainless steel appliance, huge undermount sink, glass backsplash, separate wet bar and more. The 2-by4-foot white porcelain rectangular tile flows seamlessly from room to room with water views that entertain you every moment of every day. With the Intracoastal Waterway just beyond the brick paver back patio, the wildlife is abundant, more than you can imagine, with morning sunrises that softly greet you as you awaken to a true slice of paradise. The entire glass-enclosed 23-by-12-foot lanai brings so much light, brightness and cheerfulness that it makes your heart smile. The end unit offers privacy and protection with lush green mangroves creating a protected area plus easy access for entering the water, going for a swim, fishing or kayaking. Back to the renovations, the main bedroom en suite offers privacy with upscale bath appointments, a double sink, and large designer shower. The enclosed laundry area right off the bedroom was carefully crafted with a walk-in closet, extra storage room and a rare whole-house water purification system. Not to mention all hurricane windows and doors throughout with additional footings, foam support and steel beams under the sliding doors to ensure structural integrity and peace of mind. All appliances are 2025, LG Thin Q washer and dryer, Café kitchen appliances, tankless hot water tank, custom fan and lights, all new plumbing and electrical as the home was taken down to the studs. PVC sewer lines completely replaced all cast iron pipes. New tile roof in 2025. There is nothing to do except move in and relax. You will not be disappointed. All FEMA regulations have been completed, including inspections. Vibrant waterfront 55-plus community with 40-slip marina and deeded beach access to gorgeous beaches of Longboat Key. Close to restaurants, shops, renowned St. Armands Circle, plus 30 minutes to Sarasota International Airport. Take a look.

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

Listing Agent: Kimberly Freiwald (941-256-6775)

Remarks: Introducing a Cedars East condominium unit offering the space and privacy of a single-family home with the ease of condo living. Elevated among the treetops on the Bay side of the island, the home enjoys partial Sarasota Bay views and exceptional access to Sarasota Bay waters perfect for launching a kayak, fishing, enjoying the tide pools. There is a private bay beach access for residents. This premier tennis community home features 2 oversized garage spaces, wood floors throughout the first elevated floor, a bright, open great room with a large open kitchen for entertaining, with water views of Sarasota Bay, and inviting fireplace, screened decks for bay breezes, and an office/den. Upstairs is the primary bedroom with multiple walk-in closets, ensuite bathroom and screened porch where you can unwind and catch a glimpse of the sunset glow over the treetops. Two guest bedrooms share a full bathroom. Offered furnished. Cedars East is filled with amenities. From the clubhouse with a restaurant and Tiki Bar, pool, to walking trails through the mangroves, a kayak launch and a bayside community pier for gathering, fishing and enjoying the sunrise. A tennis club membership allows access to tennis and pickleball courts, tournaments and more. There's even an onsite tennis pro if you need lessons. Cedars East offers destination packages and Tennis Pro Clinics on 10 clay courts! The game of Tennis is taken seriously...beginning June 1 the Nike Tennis Camps will be managed by John Eagleton, Co-founder and Executive Director of SportsEdTv and world-renowned tennis coach Sekou Bangoura providing focused instruction to sharpen skills and develop strategy. The program includes personal evaluation to identify strengths and opportunities for development. And...if you are not a camp candidate, the camp offers opportunity for enhanced rental income during this season! What are you waiting for? Make this your home or income opportunity today!

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

Listing Agent: Eileen Saunders (662-404-0816)