luxury seaside properties for sale Longboat Key, United States

Welcome to island living on Longboat Key, one of Sarasota's premier barrier island destinations. In Triton Cove, this coastal residence offers direct Gulf Beach access across the street and a lifestyle designed for boating, seasonal use or year-round living along Florida's Gulf Coast. Enjoy nightly sunsets along Gulf of Mexico Drive or experience world-class dining and shopping on nearby St. Armands Circle. An elevated entry leads to the main living level, where expansive glass defines the open-concept design, connecting the living room, kitchen and dining areas. Positioned within a five-residence enclave, this property offers convenient access to Sarasota dining, shopping and waterfront recreation while supporting a low-maintenance ownership experience. This tri-level single-family home features four bedrooms and 2.5 baths, complemented by a two-car garage with dual 8-foot doors and extensive storage. The ground level includes multiple flexible-use rooms ideal for fitness, storage or organization of beach equipment, kayaks, bicycles and boating gear. A dumbwaiter provides direct access from the garage to the kitchen. Interior features include engineered wood flooring in main living areas and new carpet in bedrooms. The kitchen is designed with wood cabinetry, granite countertops, deep storage drawers, an appliance garage, a rollout pantry wall and stainless steel appliances, including a GE wall oven/microwave combo, an induction cooktop and an LG refrigerator. Additional features include a wet bar with cabinetry and a mirrored wall, an electric fireplace and plantation shutters. The primary suite offers a private setting with dual vanities, a soaking tub, a separate shower, two walk-in closets and a Juliette balcony with partial gulf views. The third level includes a bonus room suitable for media, an office or a private retreat. Outdoor living includes a natural gas-heated pool and spa, an outdoor shower and a private fenced setting. Pool systems including a new motor, filters and heater, and the interior of the pool has been refinished. Recent improvements include a 2024 shingle roof with warranty, zoned HVAC systems installed in 2018 and 2020, and a 2025 water heater. The home includes a monitored alarm system. Triton Cove offers a maintained environment with low monthly HOA fees of $500, including landscape maintenance of common areas, pest control, pool service and exterior lighting. Leasing is permitted up to four times annually with a one-month minimum. Located near Longboat Key Bayfront Park and Longboat Dog Park, residents may enjoy pickleball, tennis, playgrounds and picnic areas. Nearby conveniences include grocery, pharmacy, boat rentals and storage options along Longboat Key, as well as being within reach of Sarasota amenities. Optional membership to the Longboat Key Club provides access to golf, tennis, beach and social amenities, enhancing the gulf-front lifestyle experience on Florida's west coast. Don't miss out on your private tour of this special coastal home featuring four bedrooms, 3000-plus square feet of air-conditioned living space, a two-car garage, a 30-foot pool and a hot tub on Longboat Key with beach access with low taxes for under $2 million; this is an extraordinary value!

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.

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.

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.

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.

One or more photo(s) has been 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.

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.

Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness. With five bedrooms, 7.5 baths and a sprawling layout, this magnificent property is an exceptional backdrop, just waiting for your personal touch. Arrive in style via the elegant front circular driveway or utilize the private rear driveway leading to a rare four-car garage. Inside, the home is masterfully designed for grand entertaining and everyday comfort, with a sweeping curved stairway at the entrance, setting the stage to an exquisite residence. The first floor features a formal living room and a sun-drenched family room complete with a fireplace, custom built-ins and multiple French doors, leading to the outdoor bliss. A screened lanai lays the foundation for Florida living at its finest, showcasing an enormous 33-by-46-foot sparkling heated pool and spa, expansive patio and an outdoor kitchen. The expansive open kitchen is a chef's dream, flowing seamlessly into a casual breakfast nook. For formal affairs, the large dining room offers custom cabinetry and an adjacent wet bar. The main-floor primary retreat is a sanctuary, featuring a dedicated sitting area and luxurious dual en-suite baths. There is more closet space than a clothes diva could possibly desire. The first floor is completed by a handsome office/library with built-ins, a powder room and a guest bedroom. Upstairs, you will find three additional en-suite bedrooms, one of which benefits from private back-staircase access, ideal for an au pair, in-laws or VIP guests. With every bedroom featuring its private bath, privacy is guaranteed for all. Outdoors, the walled double lot provides a private tropical oasis, all with tranquil, serene views. On a practical note, roof was replaced in 2019, with hurricane shutters, for peace of mind. Two 18-hole championship golf courses, 12 Har-Tru tennis courts (four lighted), croquet and pickleball courts, a state-of-the art fitness center, fine and casual dining options and a calendar of social events, The Oaks is Sarasota's leading golf and country club.