Lido Key Homes with Gulf/Ocean to Bay Frontage

Welcome to Lido Key, a stunning barrier island nestled off the coast of Sarasota, Florida. Known for its pristine beaches, vibrant culture, and breathtaking natural beauty, Lido Key is the perfect destination for those seeking a slice of paradise. With its unique charm, this idyllic locale offers a harmonious blend of relaxation and adventure, making it an ideal place to call home.

Lido Key boasts an array of luxurious homes with Gulf and Ocean-to-Bay frontage, providing residents with unparalleled access to the sparkling waters of the Gulf of Mexico and the tranquil bayside. Imagine waking up each morning to the gentle sound of waves lapping against the shore and enjoying panoramic views from your own private balcony. These exquisite properties are not just homes; they are a lifestyle, offering a front-row seat to stunning sunsets and the vibrant marine life that inhabits the surrounding waters.

In addition to the stunning real estate, Lido Key is home to a variety of outdoor activities. Residents can enjoy kayaking, paddleboarding, or simply strolling along the soft sandy beaches. The nearby Lido Beach Park offers picnic areas, walking trails, and convenient access to the beach, making it a perfect spot for family gatherings or a day of relaxation in the sun.

With its rich history, artistic flair, and close-knit community, Lido Key is more than just a place to live; it’s a place to thrive. Explore the charming boutiques, gourmet restaurants, and cultural attractions that dot the island, and discover why so many choose to make Lido Key their forever home. Come experience the allure of coastal living in this enchanting Florida gem!

Newest Lido Key Homes with Gulf/Ocean to Bay Frontage

$3,650,000

3 Beds ⋅ 3 Baths ⋅ Saint Armands Division John Ringling Estates SubDv. ⋅ 34236 Zip Code

The ultimate beachside condo alternative is now available furnished and move-in ready! From the moment you step inside, you're greeted by an architectural transformation designed to maximize light and luxury. Stunning porcelain flooring runs throughout the home, extending seamlessly out to the pool and outdoor living spaces. The heart of the home is the newly reimagined open kitchen, where a raised ceiling sets the stage for a beautiful marriage of modern amenities and timeless charm. Walls of glass frame the waterfront views, bathing the entire living space in natural light. For ultimate peace of mind, the property is fully fortified with impact doors and windows, along with premium flood barrier protection. The lifestyle continues outside on a wide boating canal that opens endless possibilities for water activities right from your backyard. Whether it's fishing, kayaking through the lagoon, cruising the open bay, or watching the manatees play. A boater's dream, the property features a new dock and a secure seawall. Outdoor living is completely redefined. The tropical courtyard pool has been newly landscaped with carefree plantings, offering total privacy for swimming or alfresco dining. Entertain guests in a dedicated barbecue area complete with a beautiful pergola, a cozy fire pit, and two outdoor showers for rinsing off after a day at the beach. Convenience matches the luxury with a two-car garage featuring a loft, offering additional space for storage or future expansion. This residence is more than just a home, it's an exquisite retreat in a coveted location, offering the ultimate combination of luxury and privacy. Whether you're throwing in a line to catch dinner or winding down to a breathtaking sunset, this home invites you to embrace the Florida waterfront lifestyle, and just a quick stroll away from Lido Beach and St. Armands Circle.

556 N Washington Drive, Sarasota

$11,900,000

5 Beds ⋅ 8 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code

At the end of Westway Drive, where Lido Shores meets the open water of New Pass, 1435 Westway Drive occupies one of Sarasota’s most extraordinary waterfront settings. Private, gated, and set on a double lot, the estate captures sweeping views across New Pass toward Longboat Key while offering direct deepwater access to the Gulf of Mexico and Sarasota Bay. This is the rare property that delivers every element of elevated coastal living in one address: boating, privacy, architectural presence, beach access, proximity to St. Armands Circle, and a level of land rarely found on Lido Key. Designed by Brian Phipps and built in 2013, the British West Indies–inspired residence blends timeless coastal architecture with modern luxury. Inside, expansive living spaces are framed by tall ceilings, walls of glass, rich wood flooring, custom millwork, and a natural connection to the water beyond. The great room opens to the waterfront terraces, creating an effortless flow between interior comfort and outdoor living. The kitchen is designed for both daily living and large-scale entertaining, with premium appliances including Sub-Zero and Wolf, generous stone surfaces, custom cabinetry, and an open connection to the main living and dining areas. Whether hosting guests after a day on the boat or enjoying a quiet evening overlooking the water, the home feels equally suited to celebration and retreat. With five bedrooms, two primary suites, and elevator service, the floor plan offers rare flexibility for owners, family, and extended guests. The upper-level owner’s retreat is a private sanctuary, complete with a sitting area, wet bar, wine refrigeration, espresso station, study, dual walk-in closets, and a terrace overlooking New Pass, the Gulf, and the lights of Longboat Key beyond. The outdoor living experience is exceptional. Covered terraces, a summer kitchen, resort-style pool, waterfall feature, and waterfront lounge spaces create a private setting designed around the view. The dock includes a 24,000-lb boat lift and additional jet ski lift, placing premier boating waters directly at your door. From here, New Pass provides immediate access to the Gulf, Sarasota Bay, Longboat Key, and the surrounding barrier islands. What truly sets the property apart is its scale. The estate spans approximately three-quarters of an acre, including an adjacent parcel that has been transformed into a lush private garden with mature landscaping, open lawn, fire pit, pond, cascading waterfall, and meandering paths. It gives the home a sense of arrival and breathing room that is almost impossible to recreate in this location. With its own gated access and generous dimensions, this portion of the property also offers future flexibility for a guest house, wellness pavilion, additional structure, or further reimagining, subject to applicable approvals. Lido Shores remains one of Sarasota’s most coveted coastal enclaves, known for its architectural pedigree, quiet streets, private beach access, and rare positioning between the Gulf, New Pass, St. Armands Circle, downtown Sarasota, and Longboat Key. Residents enjoy the privacy of a true neighborhood while remaining moments from dining, shopping, boating, beaches, and culture. Previously recognized as an HGTV Ultimate House Hunt winner for waterside living, 1435 Westway Drive is more than a waterfront residence—it is a private Sarasota estate with presence, scale, and a setting that cannot be duplicated.

1435 Westway Drive, Sarasota

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