luxury seaside houses for sale Longboat Key, United States

Some properties tell the story of Sarasota's evolution. Offered for the first time publicly in half a century, this waterfront estate in Lido Shores presents a rare opportunity to become the next steward of 1.34 acres with 247 feet of western shoreline. Held by only two families since 1974, both recognized for their lasting contributions to the Sarasota community. A rare slice of Sarasota's legacy is now ready for its next chapter. Designed by Seibert Architects, the residence reflects an important chapter in Sarasota's architectural heritage. The home encompasses more than 9,000 square feet with six bedrooms and six baths, including a library and billiards room. This home was thoughtfully designed to embrace its waterfront setting through expansive living spaces, gathering areas and water views throughout, including multiple terraces. The generous homesite presents exceptional possibilities for restoration, renovation or the creation of a new waterfront estate. Opportunities offering this scale of western-facing water frontage, private beach access and architectural provenance are increasingly rare along Sarasota's coastline. Offering a remarkable sense of privacy, yet just minutes from the boutiques and fine dining of St. Armands Circle, downtown Sarasota's renowned arts and cultural institutions, theaters, galleries and museums, this exceptional property also enjoys convenient access to international airports and multiple international gateways, connecting this storied waterfront setting to destinations around the world.

For Those Who See Home as an Expression of Art. 541 S Washington offers a rare blend of architectural character, quality craftsmanship, and waterfront living. Beautifully renovated to reflect the enduring principles of Mid-Century Modern design, where clean lines, natural light, and a connection to the outdoors shape the living experience. Set on 75 feet of canal frontage along prestigious South Washington Drive, just moments from St. Armands Circle, Lido Beach, and downtown Sarasota. From the moment you enter, expansive folding glass doors frame the water beyond. A striking gas fireplace anchors the main living spaces, while thoughtfully proportioned rooms balance openness with comfort. Offering four bedrooms, four-and-a-half baths, and a flexible bonus space, the 3,395-square-foot floor plan was designed for easy every day living. At the center of the home, a custom Poliform kitchen with premium Miele appliances combines clean design with exceptional functionality. The primary suite serves as a private retreat, complete with a spa-inspired bath and outdoor shower. Throughout the residence, the current owners have also enhanced the property with Control4 home automation, security system, new HVAC system, instant-on hot water heaters, whole-home water treatment, Icynene insulation, and a reinforced roof with tiedowns. Outside, curated tropical landscaping creates privacy around the heated saltwater pool. Multiple outdoor living spaces, including an expansive balcony and rooftop deck, provide beautiful settings for sunset views, while a private kayak launch offers direct access to Sarasota's waterways. A distinctive waterfront residence in one of Sarasota's most sought-after island neighborhoods, inspired by timeless design and a connection to the water. Inquire with the listing agents for a complete list of updates and to schedule your private showing.

Incredible income potential with this premier, Florida vacation-rental property. Ideally located just steps from the coveted, white-powder, sands of Lido Beach, this high-occupancy, luxury rental home combines high-end design with exceptional income-producing potential. A resort-style sanctuary for up to twelve guests, this Sarasota property offers 9,258 of masterfully-curated, square feet. Zoned for seven-day rentals and supported by a strong rental history, the property makes an attractive opportunity for investors, families or business owners seeking both personal enjoyment and revenue generation. The outdoor living is exceptional with more than 3,300 square feet of covered patios and six balconies culminating in a rooftop deck with 360-degree views of the gulf, bay and city skyline. Dine under the stars with a well-appointed summer kitchen and relax after dinner on the fun putting green. The grounds offer a lush, tropical oasis with a refreshing waterfall spilling into a sparkling saltwater pool. Serene, fiber-optic lighting and the exterior music system will transform the evening while guests relax in the twelve-person spa. Multiple outdoor lounging and dining areas accommodate everything from family gatherings to corporate retreats with multiple TVs, beverage refrigerators and game spaces for pool or ping pong. Designed with entertainment in mind, the refined interior spaces come complete with a collection of premium furnishings. A Sonos multi-room audio system and 12 high-definition TVs enhance entertainment throughout the property. The chef's kitchen offers a spacious waterfall-edge island and features a Sub-Zero refrigerator, Wolf eight-burner gas range, dual dishwashers, floating shelves and sleek European-style cabinetry. Bespoke finishes elevate every space, including quartz countertops, designer lighting, an interior elevator, custom tambour wood walls, artisanal iron stair rails, 7-inch baseboards and 8-foot interior doors. Each floor includes a wet bar with beverage refrigerators, ice makers or dishwashers, creating effortless flow for entertaining. The primary suite offers a serene private retreat with a spa-inspired bath featuring a backlit marble wall, designer fixtures and a walk-in shower with rain and handheld showerheads. Five additional bedrooms each feature uniquely designed en-suite baths with custom mirrors, distinctive tile work, sleek cabinetry and under-lit vanities. Advanced smart-home technology includes a comprehensive surveillance system with high-definition cameras, whole-property Wi-Fi, intelligent access control, programmable architectural lighting and motorized window treatments. Ideally located near pristine Gulf beaches, St. Armands Circle and downtown Sarasota's dining, arts and entertainment, this residence offers the rare combination of luxury living, strong rental income and exceptional appeal for families, executives or investors.

LAST OPPORTUNITY to acquire a COMMERCIAL/RETAIL SPACE in Sarasota's walkable Rosemary Arts and Design District with the prospect of OWNING rather than leasing commercial space in this active downtown setting. Now available, this 882-square-foot retail and commercial office condominium suite at Villa Ballada offers street-level access, prominent visibility and the flexibility to customize the space for its intended use. MOST IMPORTANTLY: SARASOTA'S OFFICE MARKET EARNS NATIONAL SPOTLIGHT: 1. Sarasota ranked #2 out of Top 50 US Markets! 2. LOOPNET says – Sarasota Market offers strong underlying demand to offset its tighter asset pool. 3. Sarasota job market growing faster than all but 2 of the 49 markets studied , driving long term demand for office space. 4. Strong job growth, Quality Buildings, and Limited Supply drives Long Term Demand for Office Space. Source: LOOPNET: “Best Cities for Office Investing in 2026”, Sarasota Magazine and Business Observer. VILLA BALLADA, Czech for “House of Harmony,” is a modern mixed-use condominium development featuring two professional retail spaces beneath 22 residences. The suite features approximately 34 linear feet of glass frontage, providing substantial street exposure for a business, professional office, retail concept or gallery. Designed by Sarasota-based architecture firm Halflants + Pichette, the award-winning development features contemporary architecture, masonry walls between suites and valuable Downtown Edge zoning. Currently due to be completed in November, the suite is scheduled to include a new half bath, new heating, ventilation and air-conditioning system, installed fire sprinklers and 100-amp electrical service. Walls and ceilings will receive a painted finish, while the concrete floors allow the buyer to select a preferred finish and further customize the space for its commercial use. MONTHLY CONDOMINIUM FEES are $480 which includes water/sewer/trash, building insurance, building maintenance and management. Street parking is available along Kumquat Court, Fourth Street, Lemon Avenue and Orange Avenue. THE LOCATION PROVIDES CONVENIENT ACCESS TO CITRUS SQUARE, ORANGE AVENUE, LEMON AVENUE, BOULEVARD OF THE ARTS, FOURTH STREET AND FRUITVILLE ROAD, WITH NEARBY RESTAURANTS, RETAIL, SHOPPING, ARTS AND CULTURAL DESTINATIONS. Whether establishing a business location or adding a commercial property to an INVESTMENT PORTFOLIO, this offering provides an ownership opportunity within Sarasota's mixed-use ROSEMARY ARTS & DESIGN DISTRICT. The space may accommodate a range of permitted professional, retail or gallery uses, subject to applicable condominium documents, zoning regulations and governmental requirements. Contact agent to schedule a property tour and request the complete property information package.

What if you could get an interest rate of 2% lower than the going interest rates? Well, we can, and our Seller is looking to make that happen by buying down the rate! Contact your agent for further details. A rare opportunity to own a single-family residence in Sarasota's sought-after Rosemary District. Set on a beautifully landscaped property, this home features a towering century-old oak tree that anchors the backyard and creates a distinctive outdoor setting rarely found in downtown locations. Spanish and Mediterranean architectural elements introduce the residence, offering classic Old World character paired with solid construction and an elevation of approximately 25 feet above sea level. The property is in Flood Zone X, where flood insurance is not required. Inside, the home features high ceilings, hardwood flooring and extensive crown molding throughout. A gas fireplace adds warmth and character to the living area during cooler winter evenings. Multiple windows allow natural light to flow throughout the interior spaces. The residence includes three bedrooms, with one configured as an office or study and featuring a separate exterior entrance, offering flexibility for work-from-home use or private guest access. Outdoor living spaces include a spacious garden area, an oversized patio and a pergola surrounded by mature landscaping, creating a private setting for dining and entertaining. In the heart of the Rosemary District, the home places residents within proximity to many culinary delights, Sarasota's cultural amenities, including galleries, theaters and live music venues. More than 65 restaurants, cafés and shops are within approximately a six-block radius. The Bay Park waterfront district, a 53-acre public park along Sarasota Bay, is just five blocks away. Payne Park, the Legacy Trail for recreation and biking, Sarasota Farmers Market and Whole Foods Market are all nearby. The John Ringling Bridge provides convenient access to St. Armands Circle and Lido Beach. The property is zoned DTE, which offers future redevelopment potential, subject to city approvals. Owners may choose to enjoy the residence as a private downtown home while maintaining long-term flexibility for future planning. Or alternatively, since this is DTE zoning, this is ideal property for a restaurant possibility, just something else to consider! A unique opportunity to experience downtown Sarasota living in one of the city's vibrant and evolving neighborhoods.

PRE-CONSTRUCTION - TO BE BUILT. Divald Homes presents its? latest architectural design offering urban island-style living in downtown Sarasota with a completion date of summer 2017. This stunning courtyard pool home of 1,796 air-conditioned square feet ($625,000 including pool package), features quality construction throughout, offering light, bright, spacious living with master suite, kitchen, breakfast bar, dining room and great room opening onto 27-by-38-foot walled courtyard through tons of sliding doors and 10-to-11-foot ceilings! Plus add a paver lanai of 20-by-9 feet which provides dreamy Florida outdoor living! An alley at the rear offers access to your paver driveway and spacious two-car garage. Welcome to your huge tiled kitchen featuring a walk-in pantry, expansive island with seating for four, Energy Star rated stainless steel appliances and undermount sink, wood cabinetry with 36-inch uppers and sleek granite countertops. Tiled floor baths offer custom wood cabinetry with granite countertops detailed with undermount sinks and plenty of ceramic tile, as well as accessories. Top quality construction features steel reinforced concrete walls, beams, columns and concrete floor slab, ALL just two doors down from 10-acre Gillespie Park! Builder Warranty and 10-year Structural Warranty included. And the best part- no rules, rental restrictions or HOA fees here, with this single-family custom home! Call today - don?t miss the opportunity to view renderings, floor plans and customize your new home now.

Completely renovated two-bedroom and two-bathroom walkout (no stairs to take) on Longboat Key! Welcome to coastal luxury living in Windward Bay, one of Longboat Key's most sought-after waterfront communities. Perfectly positioned between the sparkling waters of Sarasota Bay and the pristine Gulf beaches, this completely renovated 2-bedroom, 2-bath villa offers an exceptional blend of modern elegance, resort-style amenities, and the coveted island lifestyle buyers dream about. Fully reimagined and rebuilt from the studs, this stunning residence showcases high-end craftsmanship and designer finishes throughout. Every detail has been thoughtfully upgraded, including brand-new electrical systems, plumbing, drywall, insulation, kitchen, bathrooms, fixtures, and finishes—providing the peace of mind and comfort of essentially new construction within an established waterfront community. The bright, open-concept floor plan is flooded with natural light and designed for effortless indoor-outdoor living. The beautifully appointed chef's kitchen flows seamlessly into the living and dining areas, creating an inviting space ideal for entertaining, seasonal gatherings, or everyday enjoyment. A dedicated 220-volt outlet offers convenient electric vehicle charging, adding modern functionality and future-ready convenience. One of the villa's most desirable features is its easy ground-level access with no stairs, making everyday living simple and accessible. Pet lovers will appreciate Windward Bay's generous pet-friendly policy allowing up to two pets, a rare and highly desirable amenity on Longboat Key. Step outside to your private patio retreat surrounded by lush tropical landscaping and mature greenery. Enjoy peaceful mornings with coffee, spectacular sunset skies, and relaxing evenings gathered around the fire pit just moments from beach access. The Gulf of Mexico is only steps away, offering endless opportunities for shelling, beach walks, swimming, paddleboarding, and breathtaking sunsets. Residents of Windward Bay enjoy an unmatched collection of resort-style amenities set across nearly 27 acres of beautifully maintained waterfront property, including: Three beach access points to the powdery sand beaches of Longboat Key. Nearly one-half mile of scenic waterfront walking paths and nature trails. Two heated swimming pools. Six tennis and pickleball courts. Fitness center, sauna, clubhouse, library, and social gathering spaces. Two private marinas with boat slips and jet ski slips (for rent and subject to availability). Private fishing pier with panoramic bay views. Kayak storage and launch areas. Outdoor grilling stations, fire pits, and waterfront gathering areas. Lush park-like grounds with mature tropical landscaping. Whether you're searching for a primary residence, seasonal retreat, second home, snowbird escape, waterfront villa, beach getaway, or investment opportunity, this move-in-ready residence offers an unparalleled combination of location, lifestyle, and value. Ideally located minutes to St. Armands Circle, Sarasota's vibrant arts and dining scene, championship golf courses, boating destinations, waterfront restaurants, and world-renowned Gulf Coast beaches, this exceptional property delivers the very best of Longboat Key living. Experience the ultimate in island living where luxury, comfort, boating, beach access, and resort-style amenities come together in one extraordinary coastal retreat.

Pre-Construction. To be built. Welcome to Your Dream Coastal Retreat Steps from Siesta Beach! This custom three-story home on Siesta Key's coveted north end features five bedrooms, 4 full and 1 half bathrooms and combines elegant design, elevated construction, and thoughtful luxury finishes. The light-filled, open-concept floor plan seamlessly connects the great room, dining space, and a gourmet chef's kitchen, which features a quartz waterfall island, custom cabinetry, and high-end appliances. **Expansive sliding glass doors open to over 1,200 square feet of covered outdoor living space, framing views of lush tropical landscaping and a resort-style pool with a sun shelf. The primary suite is a true sanctuary, complete with a free-standing soaking tub and an oversized walk-in shower. The outdoor living experience is unrivaled. Multiple covered lanais and balconies provide perfect spaces for entertaining, relaxing with morning coffee, or enjoying Sarasota's sunsets. **Additional features include an elevator servicing all three levels, additional guest suites, flexible bonus spaces, a two-car garage, and storm-rated windows and doors for elevated construction. Stylish coastal architecture with Hardie board siding and a metal roof completes the package. **Located just steps from Siesta Key's world-famous beaches and minutes from the vibrant shops and restaurants of Siesta Village, this location offers the perfect blend of luxury and island lifestyle. **Short-term rentals are permitted, providing a flexible investment opportunity. **This property is also conveniently located in close proximity to Downtown Sarasota, Southside Village, and top hospitals, restaurants, and entertainment. This is your chance to build a custom masterpiece in a truly unparalleled location. Build your dream home with us, or purchase the lot and plans separately. Use our trusted general contractor or bring your own builder. Are you ready to turn your vision into a reality?

On a rare freshwater spring-fed pond filled with wildlife, you'll enjoy over 3,000 square feet of living space with 4 bedrooms, 3.5 baths, a wine room, a very private office, a large family room, a chef insprired kitchen and a car enthusiast's dream 4-car garage. This house offers versatility at every turn. Have a large family in need of plenty of private space? Work from home and need a private office? Need A-rated school district? Have a lot of cars or stuff you need to store? Love outdoor entertaining? Want to moped to Siesta Key Beach? This home has a very lucrative short term rental record - set up perfectly with separate entrances, separate air conditioning, all on the east side of the house. Professionally managed, easy to continue using this home as an investment property if that is something you are looking to have in your home. Located in the coveted Southside school district and close to multiple restaurants, delis, shops, nightclubs, Sarasota Memorial Hospital and a short drive to downtown Sarasota and St. Armands Circle. Recent improvements include a metal roof (2020), exterior painting and Hardie board shingles. Come be inspired by this truly unique masterpiece. Come see for yourself.

Discover the charm of Florida living in the beautifully landscaped community of Wild Oak Bay, where lush tropical surroundings, tree-shaded streets and refreshing bay breezes create a peaceful retreat. This inviting three-bedroom, two-bath residence offers a distinctive architectural design, thoughtful improvements, and a wonderful connection between indoor and outdoor living. One of the home's captivating features is its wraparound courtyard, showcased through expansive floor-to-ceiling sliding glass doors in the living room and Florida room. These walls of glass bring in the outdoors, filling the living spaces with natural light and offering peaceful views of the tropical surroundings. Vaulted ceilings enhance the home's bright, open atmosphere, while the courtyard provides a lovely setting for relaxation or entertaining. Recently revitalized with freshly painted surfaces and replaced wood trim, the courtyard also features an upgraded, more efficient irrigation system and enhanced drainage thoughtfully integrated with the new gutter system, complementing the surrounding tropical landscaping. Numerous improvements add comfort, convenience and value, including a new roof (2025), new gutters with leaf guard system (2026), exterior painting (2025), air-conditioning system and ductwork (2021), and a newer water heater (2024). Additional updates include an impact-resistant garage door and new opener (2025), washer and dryer (2024), and new oven/range (August 2026). Garage storage cabinetry and plumbing valve replacements provide added convenience. The home is in an X Flood Zone, a favorable designation where lenders generally do not require flood insurance, potentially offering savings in homeownership costs. Wild Oak Bay is a wonderfully accessible community with winding, tree-canopied streets, tropical landscaping and gentle breezes from nearby Sarasota Bay. The home is ideally positioned near the community pool, offering convenient access to relaxation and recreation. Its desirable location provides easy access to IMG Academy, shopping, dining, cultural attractions and beautiful Gulf beaches, including Anna Maria Island. With its distinctive courtyard design, abundant natural light, extensive improvements and tranquil tropical setting, this home offers an exceptional opportunity to enjoy the relaxed Florida lifestyle.

BACK ON THE MARKET DUE SOLELY TO BUYER FINANCING. Ideally just one block from Arlington Park, this thoughtfully reimagined Tropical Mid-Century Bauhaus residence captures the effortless Sarasota lifestyle so many dream about. Filled with natural light, the inviting split-bedroom floor plan offers three generously sized bedrooms, two beautifully renovated baths, luxury vinyl plank flooring throughout, and an open kitchen that naturally becomes the heart of the home, flowing seamlessly into comfortable living and entertaining spaces. Walls of windows blur the line between indoors and out, creating a bright, cheerful atmosphere that immediately feels like home. Set on an oversized homesite, the expansive backyard offers abundant space to create the resort-style pool you've always imagined while providing generous room for outdoor dining, entertaining, gardening, pets or play. A detached studio invites endless possibilities as a yoga retreat, art studio, fitness room, workshop, or private creative space. Recent updates provide added value and peace of mind, including a new roof (2024), four year old HVAC, and a full suite of Whirlpool kitchen appliances that are approximately 2½ years old. To preserve the home's clean Bauhaus architecture, the roof vents were thoughtfully relocated to the rear of the home. Offered turnkey furnished, this exceptional residence is ready for you to unpack, unwind and begin enjoying everything Sarasota has to offer from the moment you arrive. Arlington Park is one of Sarasota's treasured neighborhoods, featuring a heated lap pool, aquatic center, tennis and pickleball courts, basketball courts, playground, dog park, recreational trails, outdoor fitness areas and expansive green spaces just a short distance away. Ideally minutes from Southside Village, downtown Sarasota, Sarasota Memorial Hospital, Siesta Key Beach, exceptional dining, boutique shopping, and Sarasota's renowned arts and cultural attractions, you'll enjoy the ideal balance of relaxation, recreation and convenience. The neighborhood continues to flourish with underground electric utilities planned throughout the area and striking new homes completed and under construction nearby, underscoring the enduring desirability and long-term value of this sought-after location. Whether you're searching for a full-time residence, seasonal escape or investment in one of Sarasota's vibrant neighborhoods, this is a rare opportunity to own a beautifully updated architectural home on an oversized lot where timeless design, modern comfort and an exceptional lifestyle come together. Schedule your private showing today and discover why so many buyers fall in love with Arlington Park.

Looking for a stunning home close to the Siesta Key Village and America's number one beach? Looking for a home that has a built-in mother-in-law suite or the potential for income? Envision this beautifully re-modeled, turn-key furnished, four bedroom home with office, private dock potential on the Grand Canal, fully fenced yard, private heated pool and spa, wood-burning fireplace, new coastal kitchen, new bathroom with steam shower, Travertine and Mexican tile throughout, two newer air conditioning units and large private deck. This property exemplifies everything needed for true island living in a quiet neighborhood. In addition, this home may be used as a duplex, allowing for monthly rentals as an extra income benefit ($60,000 in 2014). The space can be configured as a 3/2 and 2/1.

A boater's paradise on Siesta Key! This sprawling single-story waterfront residence positioned on a half-acre home site adjacent to the Grand Canal comes with two lifts and dual personal watercraft platforms. Everything about this home invites its owners to relax and embrace the Siesta lifestyle. From the abundant outdoor space including a heated saltwater pool and spa, multiple entertaining areas overlooking the lush landscaping and water, to the easy-flowing floor plan with generous gathering areas, 829 Idlewild Way invites you to stay a while, every day. With 4 bedrooms and 3 and a half baths (two are en suites) positioned at the corners of the home, privacy is ensured for everyone. The extraordinary primary suite offers a luxurious respite at the end of the day with spa-like bath awash in natural light, with a dual-entry shower of travertine and glass and multiple showerheads, sliding privacy glass doors to the outdoor area, jetted spa tub, dual separate vanities and a water closet with a bidet, a large walk-in closet with custom built-ins and dressing area and a spacious bedroom featuring an architectural ceiling, fireplace and with abundant natural light, this elevated retreat awaits you. The center of the home is where everything and everyone comes together. Separate yet open areas flow seamlessly from dining to entertaining to lounging, ultimately leading through the four sets of impact-rated double doors to the resort-like environs beyond. At the center of all this is a kitchen that will inspire and satisfy accomplished and aspiring chefs. Miele appliances including dual ovens, microwave drawer, cooktop, two-drawer dishwasher, built-in separate refrigerator and freezer and central cooking island are surrounded by contemporary custom cabinetry, exotic granite surfaces and accent lighting throughout. Of course, if you prefer to present and serve alfresco, everything you need is just nearby. For those who value a bit of practicality beyond luxury, the oversized three-plus-car garage (a lift is included to accommodate four vehicles) will provide ample space for vehicles and toys. Additional practicality is possible given the orientation of two guest rooms, full bath and separate living room, potentially providing a generous guest/in-law suite within the home. If you are dreaming of a laid-back beach and boating lifestyle at the number one beach in the U.S., this is your place.

Pre-Construction. To be built. Welcome to a luxurious modern retreat in The Preserve on Longboat Key. This exquisite residence boasts 4 bedrooms and 4.5 bathrooms across 2,788 square feet of impeccable design. Built with Italian flooring, cabinetry, and fixtures, the home exudes a timeless elegance. Enjoy the ultimate privacy and relaxation with a spacious primary bedroom, complemented by a spa-like ensuite. The primary wing extends its allure outdoors with a wrap-around balcony, offering panoramic views of the lush surroundings. The open-concept living spaces seamlessly blend style and functionality, creating an ideal environment for both entertaining and everyday living. The kitchen is a culinary masterpiece, featuring top-of-the-line appliances and sleek design, the sliding glass doors invite natural light to illuminate the interiors, enhancing the overall ambiance. Step outside to a meticulously landscaped yard, where outdoor living spaces beckon for gatherings or peaceful solitude. Enjoy the convenience of being just a short stroll from exceptional restaurants, upscale shopping, and breathtaking sunsets. Experience the sophisticated yet relaxed lifestyle that comes with being a resident of the North Village on Longboat Key.

Private island home for sale on Jewfish Key, Longboat Key, Florida. This 4-bedroom, 4-bath waterfront residence sits on a 1.24-acre titled lot with approximately 300 feet of water frontage and a private deep-water dock, and it is reached only by boat. It is one of just eight homes on this roughly 38-acre island at Longboat Pass. 7143 La Lenaire Drive is offered turnkey and furnished, and it is on the market for the first time in more than two decades. Reached only by boat, this private island home offers something rare on Florida's coast: luxury, privacy, and room to truly disconnect. Far from crowded waterfront rentals, it's a place to slow down, enjoy the people you came with, and share an experience your family and friends will never forget. The home was custom built in 2011 and has more than 2,700 square feet of living space, designed around sweeping west-facing water views and easy indoor-outdoor living. The main living areas open to covered outdoor space overlooking the Intracoastal Waterway, and at sunset the evening light fills the rooms. The layout works as well for a quiet weekend for two as it does for a full house of guests. Walk down to your own deep-water dock, with direct boating access to Sarasota Bay, the Intracoastal, Longboat Pass, and the Gulf. Anna Maria Island, Longboat Key, and St. Armands Circle are minutes away by water, so Sarasota and Bradenton dining, shopping, beaches, and culture are easy to reach while your evenings stay quiet and private. Jewfish Key is surrounded by sandbars, clear shallows, native wildlife, and natural shoreline, a setting that is increasingly hard to find along the Gulf Coast. This property works as a primary residence, a private Florida vacation home, or an income-producing investment. With four bedrooms, four baths, and a boat-access location unlike anything else on the rental market, it offers strong short-term and seasonal rental potential for investors seeking a one-of-a-kind luxury waterfront asset between Longboat Key and Anna Maria Island. Schedule your private boat tour today.

Imagine this, morning bike rides to Siesta Key Beach, afternoons beside your private pool, sunsets from the west-facing deck and dinner under café lights in the screened lanai. Minutes from Siesta Key, The Hollywood House offers a coastal Sarasota lifestyle from a private setting right at the end of the street in Emerald Harbor. Surrounded by tropical landscaping, this renovated four-bedroom, three-bath residence brings together indoor/outdoor living with an expansive swimming pool, fenced backyard, screened-in lanai and outdoor shower. Above the two-car garage, an elevated west-facing rooftop deck provides another place to unwind as the sun sets. Inside, mid-century character meets thoughtful updates, with vaulted ceilings, exposed beams, updated flooring, quartz kitchen with new appliances and renovated baths. The primary suite delivers one of the home's must-see details, a clawfoot bathtub beside a window overlooking the private tropical landscaping. There are so many significant improvements throughout the residence so please ask for our detailed list. Experience a home that puts beaches, outdoor living and Sarasota lifestyle just minutes from your door. Shopping, fine dining, downtown, Sarasota cultural arts, and top-rated schools and medical facilities are a short drive from home.

Virtually Staged. This exquisitely reimagined waterfront estate embodies modern luxury and serene exclusivity, offering 174 feet of prime waterfrontage in the prestigious Sanderling Club on Siesta Key. On a lush, nearly half-acre parcel, the residence enjoys a southern orientation, where panoramic views of a bridgeless bay unfold through walls of glass. A backdrop of meticulously landscaped greenery ensures privacy, all just near the water's edge. At the heart of the home lies a state-of-the-art culinary haven. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, including a gas range and integrated espresso system, set within rich Merillat solid-wood cabinetry and dual islands designed for function and entertaining. Flowing seamlessly into the sunlit living and dining areas, the open-plan design creates an effortless connection between indoors and out. The living space extends gracefully to a sophisticated entertainment patio, where a firelit lounge, sparkling pool and fully appointed outdoor kitchen echo the refinement found within. The primary suite offers a tranquil retreat, framed by a garden and oak vista, and complemented by a spa-inspired bath featuring a deep soaking tub, dual vanities, and indoor and outdoor showers. An adjoining office doubles as a guest suite, while additional en-suite accommodations ensure privacy and comfort for visitors. Modern conveniences and peace of mind abound such as remote-controlled wrought-iron gates, impact-resistant windows and doors, whole-house water treatment, advanced smart-home systems, new roof, backup generator and environmentally conscious amenities, including a 500-gallon propane supply and integrated mosquito-repellent system. As a resident of Sanderling Club, you'll enjoy access to a private beach, boat slips, tennis courts, clubhouse and 24-hour security, an unrivaled blend of leisure, privacy and coastal sophistication. This residence has been meticulously curated for those who seek the ultimate fusion of luxury and tranquility, an invitation to a lifestyle defined by elegance, ease and timeless waterfront living.

It's All About the View. Some homes are defined by their architecture. Others by their location. This one is defined by what you see the moment you walk through the front door. Tucked away at the end of one of Siesta Key's most private, tree-lined streets, this exceptional bayfront retreat enjoys nearly 180-degree panoramic views across Sarasota Bay, where endless open water, spectacular sunrises, and distant estate homes create a setting that is nothing short of mesmerizing. It is a view that changes by the hour and never gets old. Originally designed by Tollyn Twitchell, son of Sarasota architectural pioneer Ralph Twitchell, this distinctive mid-century residence embraces its architectural heritage with soaring ceilings, expansive walls of glass, and light-filled living spaces designed to celebrate the waterfront. The main residence offers two bedrooms, two baths, plus a spacious office or den, while the detached one-bedroom guest house provides the perfect private retreat for family, friends, or extended stays. With 75 feet of Sarasota Bay frontage, a newly updated dock featuring composite decking and a 13,500-pound boat lift, mornings can begin with coffee overlooking the bay before heading out for a day of boating, fishing, paddleboarding, or simply enjoying the peaceful waterfront surroundings. Tucked behind a natural mangrove shoreline, the property offers both beauty and protection while remaining just minutes from Siesta Beach, Siesta Village, and convenient access on and off the island. Whether you're searching for a peaceful island escape, an architecturally significant waterfront residence, or the perfect site to create a future dream home, opportunities like this rarely become available.

Pre-Construction. To be built. Architectural Rendering Of What Could Be Built Are For Planning Purposes Only. An Extraordinary Gulf-Front Estate Opportunity! There are few opportunities remaining to create a legacy estate directly on the Gulf of Mexico. At 7740 Sanderling Road, nearly one acre of pristine beachfront offers an exceptional canvas for a world-class custom residence in one of Florida's most exclusive coastal communities. Positioned along the sugar-white sands of Siesta Key, this rare Gulf-front homesite presents an unparalleled opportunity to design a private waterfront retreat with sweeping panoramic views of the Gulf of Mexico, spectacular year-round sunsets, and direct access to one of the world's most celebrated beaches. With expansive frontage and generous dimensions, the property invites limitless architectural possibilities-from a contemporary coastal masterpiece to a timeless estate designed for generations to enjoy. Located within the prestigious Sanderling Club, this exceptional property enjoys the distinction of being part of Siesta Key's only private, gated Gulf-front community with 24-hour manned security. Originally envisioned by renowned Architect Paul Rudolph, Sarasota School of Architecture, Sanderling Club has long been recognized as one of Sarasota's most coveted residential enclaves, where privacy, natural beauty, and architectural excellence come together in a setting unlike any other on Florida's Gulf Coast. Residents enjoy an exclusive collection of amenities, including a private beachfront clubhouse overlooking the Gulf, tennis and pickleball courts, a marina with boating access to Sarasota Bay, scenic nature canopy roads , and beautifully maintained grounds that preserve the community's tranquil coastal character. The neighborhood's low density and commitment to preserving its natural environment have made Sanderling Club one of the region's most enduring luxury addresses. Beyond the gates, Siesta Key offers an internationally acclaimed lifestyle defined by its powder-soft quartz beaches, turquoise Gulf waters, and relaxed sophistication. From waterfront dining and boutique shopping in Siesta Key Village to boating, paddleboarding, fishing, and endless days on the water, the island offers an effortless blend of recreation and refinement. Just minutes away, downtown Sarasota provides a vibrant cultural scene that rivals much larger metropolitan destinations. Residents enjoy world-class performing arts, acclaimed restaurants, private clubs, championship golf, luxury shopping, art galleries, marinas, and exceptional healthcare. From evenings at the Sarasota Opera or the Van Wezel Performing Arts Hall to waterfront dining at Marina Jack and shopping at St. Armands Circle, Sarasota continues to rank among the nation's premier luxury lifestyle destinations. Large Gulf-front homesites of this caliber have become exceedingly rare. Combining nearly an acre of buildable beachfront, extraordinary privacy, direct Gulf frontage, and the prestige of Sanderling Club, 7740 Sanderling Road represents an opportunity to create an iconic waterfront estate in one of the most desirable addresses on Florida's Gulf Coast. This is more than a homesite-it is the foundation for a legacy.

Newly built direct bay front home in gated Sunset Harbor offers full sunset views over Anna Maria Island. Situated on a private cul-de-sac with 85 feet of Intracoastal Waterway frontage, the elevated residence includes 4 bedrooms, 3.5 baths, 2,798 square feet of heated living space, a private elevator, and an oversized four-car garage. The open floor plan features high ceilings, a gas fireplace, and a kitchen with solid wood cabinetry, solid-surface countertops, and built-in appliances. Upstairs includes the primary suite, a study/den, and guest bedrooms. Outdoor amenities include a heated saltwater pool with a 38-foot lap lane, an in-ground spa, covered living areas, and an outdoor kitchen-all overlooking the water with sunset views toward Anna Maria Island. A deeded on-site boat slip includes a private dock with water and electric, a fish-cleaning station, and a 10,000-pound boat lift. Enjoy sunsets all year long! Walking distance to the beaches, shops and restaurants of Anna Maria Island!

Just completed and ready for immediate occupancy! Discover refined island living in this newly built coastal contemporary residence by Modus Builders, recognized as the 2025 Home of the Year. Nestled in the heart of Holmes Beach, this exceptional four-bedroom, 3.5-bath home showcases modern architecture, superior craftsmanship and an unbeatable setting only three blocks to the beach and five blocks to dining and shopping. Constructed with exceptional attention to detail, the home features an elevator, impact-rated glass, a durable metal roof and upscale finishes throughout, offering both elegance and lasting durability. Outside, enjoy your own secluded tropical oasis complete with a heated pool and spa, expansive covered lounge area and a fully equipped summer kitchen designed for effortless year-round enjoyment. The rooftop deck and upper level provide breathtaking sunrise views over the mangrove preserve along with glowing sunsets across the Gulf. Conveniently located near IMG Academy, pristine Gulf beaches, Publix and beloved local destinations including Toasted Mango Café, Duffys Tavern, Bridge Street and The Beach House, this home offers the perfect balance of luxury and accessibility. Situated within a monthly rental zone, the property provides enhanced tranquility and privacy without the frequent turnover associated with weekly rental areas. This newly completed coastal sanctuary presents a rare opportunity to own in one of Holmes Beach's most sought-after locations and enjoy the island lifestyle. Further reinforcing the home's value, the property recently appraised at $3.1 million in connection with the seller's bank financing and is currently offered at $2.85 million. This newly completed coastal sanctuary presents a rare opportunity to own in one of Holmes Beach's most sought-after locations and enjoy the island lifestyle.

At the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little Sarasota and Blackburn Bay, an extraordinary private estate unfolds between two worlds of water. Beyond a secluded entrance lies a residence of remarkable distinction, an Italianate architectural masterpiece spanning more than 8,000 square feet, with a private sandy beach on the Gulf and a rare, grandfathered covered boat lift on the bay. Designed by renowned architect Clifford A. Scholz and masterfully built by Delta Southern Construction, the estate was envisioned not simply as a home but as a setting for an exceptional life. Here, timeless architecture, impeccable craftsmanship and modern coastal luxury converge in a residence designed to bring family and guests together while preserving moments of treasured privacy. From the moment of arrival, the architecture reveals a quiet sense of grandeur. Cypress-beamed ceilings, graceful arches, French doors, handcrafted millwork, and luminous water views create a sequence of spaces that feel both magnificent and deeply welcoming. The living room commands a captivating panorama across the Bay, while walls of glass and elegantly framed openings blend the boundary between interior and landscape. The culinary spaces are equally impressive. A sophisticated kitchen is complemented by a dedicated wine cellar, butler's pantry, and wet bar—an entertainer's dream conceived for intimate dinners and spectacular gatherings alike. Beyond, a grand media room provides an elegant retreat for cinematic evenings, music, and cultural pursuits. The primary suite is a private sanctuary unto itself. A serene sitting room, sumptuous bath, dual closets, breakfast nook, and expansive water views create an atmosphere of effortless indulgence. Three additional bedroom suites offer luxurious accommodations for family and guests, while a fifth suite transforms into a private wellness retreat with a home gym, steam room, and sauna. A magnificent marble staircase leads to an office and library distinguished by leaded-glass doors, handcrafted built-in shelving, a coffered ceiling, and mesmerizing Gulf views. Throughout the residence, additional spaces for recreation, relaxation, and quiet spaces have been thoughtfully integrated, ensuring that every corner serves the extraordinary rhythm of life on the water. Outside, stone terraces cascade toward a shimmering infinity pool, where the architecture gives way to sky and water. Days unfold between the pool and the Gulf, afternoons drift toward the bay, and evenings become unforgettable beneath the coastal sky. For the boating enthusiast, the deep-water dock offers quick access with no bridges to the Gulf through Midnight Pass and features one of the area's rare grandfathered covered boat lifts. For those drawn to the Gulf, a private sandy beach provides a front-row seat to spectacular sunsets and the timeless beauty of the sea. Yet perhaps the estate's greatest luxury is its sense of place. North Casey Key remains one of Sarasota County's most coveted enclaves—a sanctuary of quiet privacy and natural beauty, remarkably close to world-class golf, tennis, dining, shopping, and the cultural attractions of Sarasota. This is more than an exceptional residence. It is a private coastal world—an irreplaceable estate where architecture, water, nature, and the art of gracious living come together in extraordinary harmony.

One of the most distinctive residences on Anna Maria Island, this exceptional coastal home is a true celebration of thoughtful design, effortless entertaining, and spectacular Gulf views. Just steps from the shoreline and the island's world-renowned beaches, this four-bedroom retreat was designed as a private haven for family and guests, with every detail carefully considered. An established and successful vacation rental, the property grosses over $350,000 annually, offering an exceptional opportunity for both personal enjoyment and investment. Three expansive travertine terraces create extraordinary outdoor living spaces, each offering its own unique setting. The second-level covered terrace features a fully equipped summer kitchen with grill, sink, and ice machine, overlooking the large heated pool and spa. The third-level terrace is open to the sky and furnished with a fire pit, creating the perfect place to gather while taking in unobstructed views of the Gulf of Mexico. Above it all, the rooftop terrace offers breathtaking panoramic views stretching from the Gulf to the Skyway Bridge. Every level is easily accessible by elevator or stairs. Designed for both luxury and efficiency, the home features more than 9,000 watts of solar power, offering exceptional performance with low-maintenance coastal living. The ground level includes two garages-one oversized two-car garage and a separate garage ideal for a golf cart, beach equipment, water toys, or owner storage. The second level showcases an inviting living and great room, dining area, and gourmet kitchen, with French doors opening directly to the covered terrace and summer kitchen. The kitchen is appointed with state-of-the-art appliances and a wine cooler, perfectly suited for both intimate gatherings and larger-scale entertaining. The thoughtfully designed bedroom layout offers four private en-suite retreats. Two are located on the second level alongside an office/media room, while the third level features the home's expansive primary suite and an additional guest suite. From its exceptional outdoor living spaces and sweeping Gulf views to its sophisticated interiors, impressive energy features, and proven rental history, this extraordinary Anna Maria Island residence offers a rare opportunity to experience island living at its finest.