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

Remarks: This is West Coast of Florida living at its finest, designed for those seeking a refined and effortless second home near the Gulf. Elevated and elegantly appointed, this custom residence is ideally located west of Gulf of Mexico Drive in the highly desirable Conrad Beach community on Longboat Key, where coastal serenity meets thoughtful design. Surrounded by lush tropical landscaping with accent lighting, the home blends timeless island architecture with modern comforts ideal for seasonal or extended stays. Inside, an open and inviting floor plan centers around a gourmet kitchen featuring a large quartz island perfect for entertaining, abundant workspace, and seamless flow into the main living areas. A full in-house generator provides peace of mind while you are away, making ownership as easy as it is enjoyable. Multiple porches and terraces, including a rooftop observation deck, create exceptional indoor-outdoor living and invite you to savor Gulf breezes and unforgettable West Coast Florida sunsets. The primary suite, located on the main living level, offers a private retreat with a spa-inspired bath and a serene balcony overlooking the tropical surroundings. Upstairs, guest bedrooms and a spacious loft-style family room provide flexible accommodations for visiting friends and family, all with access to wraparound terraces that capture the beauty of the island setting. The home comfortably sleeps ten, making it ideal for hosting while still maintaining privacy and comfort. Outdoor living is equally well designed, with expansive decks perfect for quiet mornings or relaxed gatherings. A beautifully landscaped path leads to the oversized resort-style community pool, complete with bath facilities and entertaining space, offering all the benefits of a luxury amenity without the responsibility of maintaining a private pool. From the community observation deck, enjoy glimpses of the Gulf and dramatic evening skies. Favorite features include high-impact windows and doors, full house generator and 5 minute walk to the soft powder sand beaches and  beautiful Gulf waters. The award-winning Conrad Beach community enhances the lock-and-leave lifestyle with lawn care, irrigation, and landscaping services included. Just moments from pristine beaches, the charm of Longboat Key’s north end, marinas, and the dining and boutiques of St. Armands Circle, this home offers the ideal blend of privacy, convenience, and coastal living. Schedule your private showing and experience how effortless owning a second home on Florida’s West Coast can be.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)

Listing Agent: Kathy Harman (941-900-9828)

Remarks: Located in the gated waterfront community of Longboat Harbour, this updated first floor residence offers direct walkout access to manicured green space and peaceful water views. Positioned near deeded beach access, the home provides a seamless blend of coastal living and everyday convenience. Interior features include tile flooring throughout, Frigidaire appliances, plantation shutters and automated blinds. The residence is offered turnkey furnished, including a West Elm leather sofa, coordinated coastal accent tables, coffee table, breakfast set and dining table with six chairs. The air conditioning system was replaced approximately two and a half years ago. All appliances and the hot water heater are under warranty, including parts and labor, through February 2027. Covered assigned parking and ample guest parking are included. Longboat Harbour is home to the Longboat Yacht Club, offering an active social calendar and waterfront gatherings for residents, whether or not they maintain a slip. Dock slips are available on a first-come basis for $460 per year. Community amenities include kayak storage and launch, seasonal dock rentals, a fitness center with instructor-led classes, tennis and pickleball courts, sauna, craft room, woodshop, library, and game rooms. No pets permitted. Rentals allowed twice annually with a 30 day minimum.

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

Listing Agent: Sharon Meier (407-927-5669)

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: 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: Recently reduced—don’t miss this opportunity. No special assessments after the 2024 storms, no history of flooding, well-funded reserves, and structural soundness supported by SIRS report! Exceptional value for a Longboat Key condo with private beach access. Enjoy deeded Gulf access with a residents-only community beach house featuring bathrooms, indoor/outdoor showers, seating, cabana space, and parking—your personal gateway to Gulf Coast living. Experience exceptional bayfront living at 4310 Falmouth Drive, Unit 102, located in the sought-after Longboat Harbour community on Longboat Key—a premier coastal city and barrier island along Florida’s Gulf Coast, renowned for attracting year-round residents, second-home owners, seasonal residents, and visitors seeking a refined, upscale seaside lifestyle. This A-Building, direct bayfront residence captures full Sarasota Bay views from the kitchen, dining area, living room, enclosed lanai, and primary bedroom—offering a front-row seat to sunrise skies, passing boats, dolphins, manatees, eagles and all kinds of exciting wildlife just 40 feet from the tranquil water vistas. Thoughtfully updated, the home features luxury vinyl flooring, upscale LG quartz Viatera Rococo countertops in the kitchen and both bathrooms, and soft-close drawers and custom cabinetry throughout. The spacious primary suite includes double vanities and a beautifully updated walk-in shower, while the guest bath also offers a walk-in shower with quartz finishes. Significant capital improvements provide peace of mind, including new hurricane-rated windows and sliders (2024, Cat5), HVAC (2021) with approximately 8 years remaining on a 12-year warranty, and a water heater (2023). The enclosed lanai expands usable living space while maintaining sweeping Sarasota Bay views. Offered fully furnished for a seamless, move-in-ready bayfront lifestyle. Longboat Harbour is a gated, resort-style community offering an impressive array of amenities, including four heated pools, tennis and pickleball courts with active player groups, fitness center, sauna, meeting rooms, billiards, putting green, woodworking shop, kayak storage, shuffleboard, locker rooms, fishing piers, two community grills, on-site management, and a protected harbor. Boat slips are available to members of the Longboat Harbour Yacht Club (subject to availability). Enjoy the best of island living with private deeded beach access just a short walk or drive across the street—complete with seating, chair storage, cabana, restrooms, indoor and outdoor showers, parking, and a convenient car-wash area. Additional features in the condo include washer and dryer connections in a hall closet and assigned covered carport parking with abundant guest spaces nearby. In the living room, open the sliders to seamlessly expand your indoor–outdoor living space, or keep them closed and enjoy the patio as an enclosed lanai—then open the glass sliders to let in refreshing coastal breezes and salt air. Located just 7.5 miles north of St. Armands Circle, and a short drive to downtown Sarasota’s Arts District, world-class dining and shopping, with Sarasota-Bradenton International Airport nearby. Direct Sarasota Bay views and private deeded Gulf beach access make this exceptional residence the ultimate Longboat Key lifestyle opportunity.

Listing is courtesy of: MARCUS & COMPANY REALTY (941-932-8550)

Listing Agent: Kerre Allman (941-909-3095)

Remarks: Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)

Listing Agent: Beth Ann Boyer (941-780-6606)

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: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, a premier luxury builder known for crafting high-end coastal residences with exceptional attention to detail and durability, this stunning new construction home at 592 Juan Anasco Dr offers an unparalleled blend of sophistication, comfort, and waterfront living. Perfectly positioned on a canal-front lot in Longboat Key, this 5-bedroom, 5.5-bath residence is thoughtfully designed to capture the essence of refined coastal living. Expansive windows, soaring ceilings, and a light-filled interior create an inviting atmosphere, while the home’s modern coastal aesthetic is complemented by carefully curated finishes and timeless design elements that elevate every space. The spacious and well-appointed floor plan offers a seamless balance of functionality and privacy, making it ideal for both everyday living and elevated entertaining. Generous living areas provide a welcoming environment for gathering, while the primary suite serves as a true retreat—offering a peaceful escape with a spa-like feel. Each additional bedroom is designed with comfort in mind, providing flexibility for guests, family, or extended stays. Step outside to your private waterfront oasis, where a resort-style setting invites relaxation and effortless entertaining. Whether hosting friends, enjoying quiet evenings by the water, or taking advantage of Florida’s year-round sunshine, this outdoor space is designed to be experienced. With direct canal access, boating enthusiasts will appreciate the ability to enjoy the Intracoastal lifestyle right from their backyard. Built to meet current FEMA guidelines and elevation requirements, this home offers enhanced protection, improved insurance efficiency, and long-term peace of mind—an essential advantage for waterfront properties. The elevated construction is thoughtfully designed to perform in coastal conditions while maintaining both functionality and architectural appeal. Living on Longboat Key means embracing a lifestyle that is both refined and relaxed. Known for its pristine Gulf beaches, world-class golf, and exclusive residential feel, the island offers a quieter, more private alternative to neighboring destinations. Residents enjoy convenient access to the renowned shops and restaurants of St. Armands Circle, the cultural attractions of downtown Sarasota, and nearby marinas, beach clubs, and nature preserves. From morning walks along the shoreline to sunset cruises and evenings of coastal dining, every day feels like a getaway. This is more than a home—it’s a lifestyle defined by waterfront elegance, modern construction standards, and one of Florida’s most sought-after coastal communities. Pricing, availability, and final details subject to adjustment prior to completion.

Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)

Listing Agent: Holly Wikfors, Llc (239-777-8075)

Remarks: Under contract-accepting backup offers. Live the Longboat Key lifestyle in this beautifully updated two-story, two-bedroom townhome, where more than $60,000 in upgrades and improvements create the perfect blend of comfort, style, and coastal charm . Features include a private deeded beach, 2 heated pools, garage, pet-friendly, a marina with boat slips, and outdoor entertaining space. Offered furnished and move-in ready. Every room reflects thoughtful, elegant design, from curated furnishings to refined color palettes. The first floor features beautiful tile flooring and numerous upgrades, including a stunning kitchen with quartz countertops and backsplash, custom cabinetry, a designer sink and faucet, Bathrooms have been tastefully updated with designer fixtures, and smart recessed lighting enhances the ambiance throughout the home. Spacious bedrooms offer ample closet space and excellent storage throughout. Upstairs, elegant dark engineered wood flooring complements the tiled bathroom, creating a warm and sophisticated retreat. The enclosed lanai provides versatile bonus space ideal for a home office or family room. Additional highlights include an A/C system with iWave-R ionization generator, washer and dryer in unit, a private garage with extra storage, an electric kayak lift with 2 tandem kayaks included. . A lovely, remodeled community room, BBQ, a private beach pavilion with parking and restrooms. Gulf to Bay access, walking distance to Bayfront Park with dog park and pickleball.

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

Listing Agent: Michael Yawitz (941-587-8091)

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: Under contract-accepting backup offers. Resort-style living at Longboat Harbour! This move in ready one bedroom, one bath condo is one of the best get-aways in the area. From your lanai, the serene view down the canal makes for a great place to have your morning coffee or enjoy a sunset cocktail. Steps away, you have private gated access to the Gulf beaches including a pavilion with washrooms, lockers and parking. If you like, this condo can be an incredible investment opportunity, earning rental income from day one. In 2025 the A/C unit was replaced, water heater 2023. In 2025, all the roofs were replaced, along with the elevators in Building E. There is private storage, assigned covered parking, and plenty of guest parking. The pool nearest you has been resurfaced and new pavers added throughout the complex. Longboat Harbour is a friendly community with numerous amenities and an on-site management team. It boasts four heated pools, tennis and pickleball courts, putting green, and kayak storage with launch. For boating enthusiasts, slips are available for powerboats and sailboats up to 34 feet on a first-come, first-served basis. At the clubhouse there is a fully equipped gym (with sauna and lockers) and the renovated community room overlooking the bay hosts many social occasions and private parties. Whether for a warm winter getaway, year-round residence or investment opportunity, Longboat Harbour is resort-style living at its best!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Tracey Fiedler (303-809-2582)

Remarks: Exceptional opportunity to own a Longboat Key waterfront home in the highly desired community of Emerald Harbor. This 3BR/2BA, 1,926-sf canal front home with pool sits on an oversized 100x155-ft lot along one of Longboat’s widest canals (~110 ft) offering deep-water boating access just a half mile to the Intracoastal Waterway. Private beach access with parking is less than half a mile away. The property experienced storm-related water damage in 2024 and is ready for renovation or a brand-new custom home build. Enjoy island living close to The St. Regis Longboat Key Resort, The Resort at Longboat Key Club, St. Armands Circle, and North Longboat Village favorites—Shore, Mar Vista, Whitney’s, and Lazy Lobster. Emerald Harbor Longboat Key home for sale combines boating, beach access, and the ultimate Florida lifestyle—an unbeatable fixer-upper Longboat Key canal-front opportunity in one of the island’s premier neighborhoods.

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

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

Remarks: Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.

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

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

Remarks: Discover Longboat Key waterfront living at its very best at 718 Spanish Dr N, a beautifully updated freestanding villa in the sought-after Spanish Main Yacht Club. This home has been completely renovated to today’s highest standards following Hurricane Ian, delivering a fresh, high-end coastal finish throughout with meticulous craftsmanship and premium materials. Just steps from your door, enjoy private deeded beach access to the powder sands and turquoise color of the Gulf of Mexico — perfect for sunrise walks, beachcombing, or sunset gatherings. Boaters will appreciate the community’s deep-water marina with boat slips priced around $1,200 annually that have direct access to the Intracoastal Waterway, and quick passage to the open Gulf, along with kayak racks and fishing right at hand. Inside, the bright open-concept 2-bedroom, 2-bath villa showcases an elevated, contemporary coastal design. The gourmet kitchen is a true entertainer’s dream, featuring sleek modern cabinetry, elegant stone countertops, a spacious island, and high-end stainless steel appliances. Sunlight pours through the generous windows and sliders, highlighting the beautiful new flooring that flows seamlessly into the living and dining areas. A sun-drenched Florida room/lanai offers flexible space, ideal for a home office, artist studio, or casual living — all overlooking lush tropical landscaping and a peaceful community setting. Both bedrooms are generously sized with ample closet space, while the updated baths feature contemporary fixtures and finishes for a spa-like feel. Additional highlights include a private outdoor shower, a spacious carport for your island toys, and thoughtful storage throughout. This vibrant, friendly 55+ community (can be under 55 to purchase) offers a heated pool, a clubhouse with marina views, shuffleboard courts, and a welcoming social atmosphere. Maintenance-free living, beautifully landscaped grounds, and covered parking complete the carefree Longboat Key lifestyle. Whether you seek a full-time waterfront residence, seasonal escape, or outstanding investment, 718 Spanish Dr N offers turnkey luxury with effortless deeded beach access and marina convenience in one of Longboat Key’s most desirable waterfront enclaves. Minutes to St. Armand's Circle, downtown Sarasota, and Anna Maria Island, yet tucked away in paradise. Don’t miss this rare opportunity to own a freshly renovated gem in Spanish Main Yacht Club — where high-end coastal living meets the best of island boating and beach life!

Listing is courtesy of: SARASOTA REAL ESTATE GROUP (941-922-8400)

Listing Agent: John Woodward (941-922-8400)

Remarks: Longboat Key waterfront lifestyle at its finest is now yours to discover. We are proud to present this stunning, fully renovated waterfront two-bedroom, two-bathroom freestanding villa-arguably a premier location within the Spanish Main Yacht Club. Situated in the middle of the north shore of serene Lake Spanish Main, it provides breathtaking views in every direction. The effortless waterfront views are the star of the show, especially enjoyed from your oversized paver patio-ideally designed for perfect island lounging-but also from nearly every room in the home. The waterfront backyard of this residence is framed by mature Black Olive trees that provide dappled shade while perfectly preserving the bright southern light and glistening water. This "center-of-everything" location is truly unbeatable, offering effortless access to your private deeded beach, the deep-water marina, the community pool, and boat slips. Modern Luxury Meets Coastal Comfort- Inside, a comprehensive renovation features custom tile flooring throughout, immediately setting an elevated, modern tone. The gourmet kitchen is an entertainer's dream, boasting custom cabinetry, designer stone countertops, and new stainless steel appliances centered around a first-class island with updated statement lighting. The open-concept floor plan flows seamlessly from the kitchen into an elegant dining area and a spacious family room, where natural light pours in alongside expansive lake views. Beyond, a sun-drenched Florida room?perfectly suited for an artist's studio and private office?offers southern-facing windows where you can watch the sunlight glisten off the water. Private Retreats-The primary suite is a sanctuary of its own, featuring a walk-in closet, generous proportions, Lake Views and a fully renovated ensuite bath. The guest wing is equally impressive, offering an ample bedroom and a stunningly renovated bathroom with a contemporary walk-in shower. Rounding out this exceptional property are the interior workshop, laundry room, additional storage, outdoor shower and a spacious carport perfectly sized for all your island toys. New Windows installed 2019, 2022 brought a new Roof and AC.

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

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

Remarks: One or more photo(s) has been virtually staged. This gorgeous two-bedroom, two-bath Spanish Main standalone villa is a must-see! The fully complete custom remodel has been beautifully and tastefully appointed with meticulous craftsmanship. So many upgrades. Starting with the neutral tile plank flooring that runs throughout the villa, providing a seamless flow from room to room. The kitchen is a chef's dream. All wood 42-inch cabinets complete the kitchen with tons of storage, slow-close drawers, under-counter sink. Friends and family will love the oversized kitchen with all your new appliances and served on the large quartz counter/island that will easily seat seven barstools. The open floor plan allows for easy social gatherings. The primary bedroom has an en-suite bath with a spacious shower with custom glass frameless shower doors. Double sinks are topped off with beautiful lighting. The walk-in closet provides plenty of storage and is complete with sensor lighting. New double heavy wood and glass doors separate the primary bedroom from the spacious lanai. The lanai is the place to sit and enjoy the view of the lush wetlands that provide privacy and a sense of tropical retreat in your backyard. The expansive lanai can be used as a flex room, such as a dining area, office, reading room, a third sleeping place or workout area. Roof new in 2019 plus all hurricane windows and doors. Go out the hurricane-grade sliders to see the view of the Bay waters and smell the sea air. The Bay view from the lanai and backyard is lovely and definitely an added bonus that adds even more beauty to your backyard paradise. Feel secure with motion sensor lights at back of the home. Electric blinds on the windows provide ease of privacy and light control. A retractable awning will allow you to enjoy your oversized brick paver patio without the warm Florida sun being an issue. Extra outdoor PVC storage room. This vibrant 55-plus community of Spanish Main Yacht Club neighborhood is full of wonderful neighbors, and lots of amenities, shuffleboards, swimming pool, private deeded beach access to the gorgeous Longboat Key beaches and warm Gulf waters. Fishing, boating, cycling and more. Close to St. Armands Circle and downtown Sarasota makes this location ideal for shopping, dining, theater, botanical gardens, airport and more. All 212 units in Spanish Main Yacht Club are under FEMA regulations, guidelines and stringent adherence to rebuild specifications. New owners will receive any balance of insurance funds that are allotted to this villa. Call for details. All FEMA regulations completed, including inspections. Ready to enjoy your piece of paradise. Can be under 55 to purchase. With 1,300 square feet under air since lanai was closed in.

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

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

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: PRICE REDUCED on this rarely available waterfront villa in Windward Bay, which lives like a single-family home while offering the convenience of maintenance-free island living. With nearly 1,900 square feet, this is the largest floor plan in the community and offers beautiful Sarasota Bay and canal views from the main living areas. The well-designed layout includes a spacious waterfront great room, two large bedrooms, two updated bathrooms, and a flexible bonus room that can easily serve as a third bedroom, home office, or private guest suite with its own exterior entrance. The open kitchen features quartz countertops, stainless steel appliances, generous cabinetry, and overlooks the living space, making it ideal for everyday living or entertaining. Recent improvements including hurricane impact windows and luxury vinyl flooring throughout provide both comfort and peace of mind. A large interior laundry room with newer full-size washer and dryer offers additional storage and the potential to add a third bathroom if desired. The attached covered carport provides convenient access directly into the home. Enjoy true Florida waterfront living from the enclosed Florida room and private patio where you can relax, grill, or watch dolphins and manatees in the canal. This well-managed community has completed its structural integrity requirements and allows rentals twice per year with a one-month minimum and no ownership waiting period, making this an excellent option for both personal use and investment. Flood insurance is included in the condo fee for additional peace of mind. Located directly across from Zota Beach Resort and close to dining, shopping, and the best beaches on Longboat Key, this property presents an outstanding opportunity to own a spacious waterfront residence at an attractive value.Windward Bay offers exceptional resort-style amenities: two heated pools with complimentary chaises, saunas, tennis and pickleball courts, a fitness center, shuffleboard, boat slips ($60/month with an owner-supplied lift), kayaking and paddleboarding (storage/launches $40/year), fishing, and three deeded beach accesses. Stroll or bike through 26 acres of professionally landscaped bayfront grounds, or head across the street to Zota Beach Resort for fine dining and sunset cocktails. This proactive community has passed its structural integrity inspection and is certified for another ten years. Owners may rent twice per year with a one-month minimum and no ownership waiting period—ideal for generating income while enjoying a peaceful coastal lifestyle. Exceptionally pet-friendly, Windward Bay welcomes two large pets up to 75 lbs each, with pet comfort stations throughout the property. Even Renters can have pets…a uniquely appealing feature for those seeking rental income. For peace of mind, flood insurance is included in the Condo fee. Seize this rare opportunity to own a tranquil island haven that combines space, style, and simplicity in a paradise-like setting. What could be better? It could be yours!

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

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

Remarks: New photos coming on this beautifully updated free-standing villa in Spanish Main Yacht Club on Longboat Key, a warm and vital boating community with private beach access, pool, clubhouse and boat slips. The community is undergoing a renaissance of sorts as many units (including this one) did have water intrusion in the summer storms of 2024. This owner contracted with the community contractor. has paid related assessment and work is nearly completed! This unit has a bright open floor plan and hurricane windows. Main living area has tile flooring and both bedrooms will have new carpet. There are two bonus areas, one is adjacent to the primary bedroom and could be a private reading area or office and the other adjoins the great room. Once completed, this unit will have two new baths, new appliances, kitchen updated, new doors and new paint throughout. This villa is on the corner and has a much-desired additional parking pad, giving as many as four parking spaces depending on car size. The laundry room, typical of Florida, is in a separate room under the carport. Longboat Key is paradise. A barrier island off Sarasota, where you can find wonderful restaurants, community tennis facilities, parks, bike lanes and a short drive to Sarasota and Anna Maria Island.

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

Listing Agent: Holly Switow (941-735-3186)

Remarks: Under contract-accepting backup offers. Nestled in the heart of Longboat Key, this exceptional two-bedroom, two-bathroom beachfront condo offers a rare blend of luxury, comfort, and high rental potential. Situated within the meticulously maintained Seagrape Inn, this turnkey furnished unit is an investor’s dream, boasting a potential gross annual revenue of $108,000 and a net operating income of $66,000. The Seagrape Inn's lush landscaping and upscale tropical ambiance create an idyllic setting along the stunning Gulf of Mexico, perfect for both personal enjoyment and income generation. Amenities at Seagrape Inn include a private entrance to each condo, a private heated pool, a private beach area with lounge chairs and umbrellas, on-site laundry and ice machine, upgraded Wi-Fi throughout the resort, cable TV, a gazebo with a gas BBQ grill, and beach towels and linens. Unit 7, perched on the second floor, provides breathtaking views of the ocean and the inviting pool below. Upon entry, the condo exudes sophistication, with a thoughtfully designed living space that seamlessly connects the living room, dining area, and upgraded kitchen. The kitchen, recently renovated to perfection, features new cabinets, countertops, recessed lighting, plumbing fixtures, and state-of-the-art appliances. The entire unit has been enhanced with new waterproof LVP flooring, fresh interior paint, and modern light fixtures, ensuring a contemporary and elegant aesthetic throughout. Both bedrooms are tastefully furnished, offering serene retreats after a day at the beach. The bathrooms have been completely remodeled, showcasing new vanities, tile work, shower doors, and plumbing fixtures. Step onto the screened balcony to savor unparalleled views of the ocean, pool, and lush greenery a perfect spot to relax and soak in the tranquil surroundings. Beyond the condo's exquisite interior, significant exterior improvements have been made, including the installation of hurricane windows and doors, new deck waterproofing, and exterior painting. The convenience of a designated parking spot adds to the property’s appeal. Located in a prime area of Longboat Key, this condo provides easy access to the beach, Gulf, and nearby restaurants and shops. Whether you're seeking a lucrative investment or a luxurious personal retreat, this beachfront condo offers an extraordinary opportunity to experience the best of coastal living in an unparalleled location.

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

Listing Agent: Patrick Brogley (941-361-9031)