luxury waterfront houses for sale Windermere, United States

Welcome to Crane's Point, one of Central Florida's most private lakefront enclaves, a gated community of just eight estate homes. This home alone commands nearly two acres with 186 feet of private frontage on 294-acre Lake Jessamine, one of the region's premier ski lakes. This is a community you have to be invited into, and a lifestyle you have to see to believe. From the moment you arrive, majestic oak trees and manicured landscaping welcome you home. Bring the boat, the jet skis, and your favorite people. This is the lakefront lifestyle you've been waiting for. At the water's edge, a private dock is outfitted with a boat lift and a double drive-on jet ski lift, putting boating, skiing, wakeboarding, and sunrise paddles just steps from your back door. Just beyond, a custom lagoon-style heated pool and spa with a telescoping fountain unfolds beneath a three-ton Tennessee stone waterfall, framed by travertine and Italian porcelain decking. An outdoor kitchen with a built-in grill, a Perlick refrigerator, and a fully wired Sonos sound system make the pergola and patio an everyday destination, not just a weekend one. Inside, 14-foot ceilings with hand-hewn wood beams, rich hardwood floors, custom millwork, and walls of windows keep the lake in view at every turn. A dedicated downstairs office and an inviting sitting room offer flexible living space, while a relaxed dining room, warmed by its own fireplace and built-in bookcases, sets an easy tone for gathering. The living room flows seamlessly into the kitchen, creating one connected, comfortable space for everyday life and entertaining alike. At the center of it all is a fully remodeled chef's kitchen built for entertaining. A 6' x 10' island topped in a single seamless slab of quartzite anchors the space, surrounded by custom maple cabinetry, a Thermador appliance suite with induction cooktop, a Rachiele workstation sink, and a dedicated beverage station with its own wine refrigerator and sink. The split floor plan offers rare flexibility. A first-floor primary suite with a spa-inspired bath and zero-entry shower is tucked away for privacy, with walk-out access directly to the pool and outdoor living space and amazing lake views. Upstairs, a second primary suite captures panoramic lake views and includes a sitting room, an expansive walk-in closet connected to your private gym that could also be extended for your dream closet with an additional private dressing space, along with a luxurious en-suite bath. Two primary suites make this an exceptional fit for multigenerational living, extended family, or long-term guests. Every major system has already been addressed, from a new commercial-grade water heater and irrigation pump to an updated septic system, French drains, all-new electrical, and an epoxy-floored three-car garage, so the only thing left to do is move in and enjoy it. Just minutes from Downtown Orlando, Orlando International Airport, and the Mall at Millenia, Crane's Point offers true lakefront seclusion behind private gates without sacrificing convenience. Homes here rarely come available. Schedule your private showing today. From Holden Ave turn onto Jessamine Lane and follow to Cranes Point Ct. Go through gate, home is the 2nd home to the left.

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.

Virtually Staged. LEGACY ON THE LAKE A ONE-OF-A-KIND PRIVATE WATERFRONT ESTATE Welcome to Legacy on the Lake, an extraordinary custom waterfront estate where luxury, recreation, innovation, and multigenerational living come together on the shores of Lake Irma. Privately gated and situated on nearly one acre with direct frontage on this approximately 123-acre skiable lake, this remarkable property offers a rare Central Florida lifestyle with opportunities for boating, waterskiing, wakeboarding, tubing, fishing, paddleboarding, and sunset views. Offering nearly 7,000 square feet of living space, the residence features 5 bedrooms and 4.5 bathrooms, expansive gathering areas, and exceptional spaces designed for everyday living and entertaining. The main residence is filled with natural light and beautiful lake views, creating a seamless connection between indoor and outdoor living. A custom TrackMan golf simulator room adds another dimension of entertainment; practice your game, play iconic courses, or enjoy the space as a private movie theater for family movie nights, sporting events, gaming, and more. Adding exceptional flexibility is the large attached yet private guest wing, complete with its own full kitchen, living room, bedroom, full bathroom, and loft. Designed to function almost as a residence within the residence, this versatile space is ideal for extended stays, guests, a private retreat, workspace, or other lifestyle needs. Outside, the property becomes a private waterfront playground with a resort-style pool and spa, expansive outdoor living areas, and direct access to Lake Irma. One of the estate's most distinctive features is an incredible custom pirate ship playground designed by Vanilla Ice, creating a truly one-of-a-kind backyard setting. Automotive enthusiasts and collectors will appreciate the massive 6-car garage, with the potential to accommodate up to 12 vehicles through the installation of professional lifts. The space also provides flexibility for storage, projects, or a private workshop. The home is equipped with an advanced energy infrastructure, including a substantial solar energy system designed to keep annual electric costs near zero under normal usage conditions, along with 12 Tesla Powerwall batteries providing significant energy storage and whole-home backup capability. While offering the privacy of a gated waterfront retreat, the location provides convenient access to UCF, Siemens, major professional and technology employers, Lake Nona, Winter Park, Downtown Orlando, Orlando International Airport, and major highways. Legacy on the Lake is more than a home it is a destination where days on the water, evenings overlooking the lake, golf, entertainment, and exceptional amenities come together to create a lifestyle that is difficult to replicate. Legacy on the Lake where today's moments become tomorrow's legacy. Schedule your private tour today. From SR 417, take University Blvd exit heading west. Go past Econlockhatchee Trl and make your first available U-turn. After a few hundred feet, 8922 will be on your right hand side.