luxury waterfront houses for sale Winter Park, United States

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.

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.

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.

Pre-Construction. To be built. Generational ownership property is now available to new owners! This six-acre lakefront property presents a rare opportunity to own one of Lake Mary's true legacy estates. This property is available as as-is without build (old home and structures remain). Set behind the private gates of The Cove, yet uniquely exempt from the community's HOA, the property is reached by a long, tree-lined private drive that opens to more than 800 feet of shoreline along Crystal Lake. Here, the lake becomes part of everyday life, offering endless opportunities for boating, waterskiing, fishing, swimming and kayaking, while western sunsets, abundant wildlife and the natural beauty of the waterfront create a sense of privacy and place that is increasingly hard to find. Planned for the site is a Transitional Modern estate to be built by Konkol Custom Homes, one of Central Florida's premier luxury homebuilders. With approximately 7,768 square feet under air and 10,790 total square feet, the residence is designed to take full advantage of the waterfront setting while offering the comfort, scale and flexibility expected of a custom luxury home. The floor plan includes five bedrooms, five full and two half baths, along with four garage spaces arranged as two separate two-car garages. Inside, expansive living areas are defined by dramatic open-to-below spaces and an easy connection between the home's main gathering areas. The great room is centered around a fireplace and flows naturally into the dining area and kitchen, where a large island and separate scullery create a layout equally suited for everyday living and entertaining. The primary suite is privately positioned in its own wing with generous walk-in closets, a spacious bath and an adjacent yoga room or flex space. A separate guest or multigenerational suite includes its own en-suite bath and walk-in closet, providing privacy and comfort for extended stays. A dedicated gym with a dry sauna creates a private wellness space at home, while upstairs an open loft, two private offices, additional storage, a covered balcony and open overlooks add versatility. An elevator provides convenient access between levels. The outdoor spaces are designed to feel like an extension of the home. A generous covered living area and summer kitchen open to the pool, deck and expansive grounds, with the lake always part of the view. Beyond the backyard, more than 800 feet of shoreline, a private dock and a boathouse make it easy to enjoy Crystal Lake, whether heading out on the boat, spending an afternoon on the water or settling in to watch the sunset. Lake Mary's dining, shopping, entertainment and everyday conveniences are only minutes away, while Interstate 4, SR 417 and the Wekiva Parkway provide easy access throughout Central Florida. (Illustrations are renderings and subject to change by buyer or builder).

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.

Pre-Construction. To be built. Live. Life. Lakefront. A rare and compelling expression of newly constructed lakefront luxury awaits on the shores of Lake Markham, where architectural brilliance meets effortless beauty of waterfront living. This property is available as LAND ONLY (call for details) or as built as shown with many interior options customizable by buyer. Expertly envisioned to maximize views and lifestyle, this extraordinary residence showcases a striking exterior clad in a curated blend of rich, luxurious materials, setting the tone for refinement that unfolds within. Spanning more than 4,700 square feet of living space and 6,600 square feet under roof, the open concept design is defined by grand yet inviting spaces, where walls of glass frame panoramic lake vistas and flood the interiors with natural light. The great room, dining space and chef's kitchen flow seamlessly together, each oriented to capture the shimmering water beyond. Designed for elevated entertaining, the expansive lanai introduces a fully appointed summer kitchen, resort-style pool and sweeping lake backdrop, an idyllic setting for sunset gatherings and elegant outdoor soirées. Days begin on the water and end in serenity, launch your boat from your private dock for a morning cruise or an afternoon of watersports along Lake Markham's scenic chain of lakes, returning home just near your door. The owner's suite is a sanctuary unto itself, privately positioned to overlook the pool and lake, complemented by a spa-inspired bath and expansive walk in wardrobes. The main level is further enhanced by a private office, mudroom, secondary bedroom suite and thoughtfully designed living spaces. Upstairs, additional bedroom suites, a loft retreat, and flexible gathering areas provide comfort and versatility for family and guests alike. With building plans submission ready, the path to completion is significantly accelerated. For those seeking a more bespoke vision, full custom design opportunities remain available. With no HOA restrictions, the freedom to create a legacy estate is without limitation. Ideally near boutique shopping, fine dining, championship golf, private clubs, premier medical facilities and miles of picturesque trails, this remarkable offering pairs tranquil lakefront seclusion with everyday convenience. This is more than a home, it is a newly built waterfront lifestyle of distinction on sought-after Lake Markham.

Exceptional waterfront living on the prestigious Butler Chain of Lakes. Discover an extraordinary expression of waterfront luxury in the charming Town of Windermere, where timeless Tuscan and Mediterranean architecture meets the elegance of refined Florida living. Ideally along the shores of Lake Down, part of the desired Butler Chain of Lakes, this exceptional residence offers a rare opportunity to experience breathtaking water views, sophisticated interiors and an unparalleled boating lifestyle. From moment you arrive, exquisite stone detailing and custom wrought-iron double entry doors establish a sense of architectural distinction. Beyond the grand entrance, soaring ceilings, expansive living spaces, and thoughtfully curated design elements create an atmosphere of understated elegance and effortless sophistication. Designed for grand-scale entertaining and intimate gatherings, the home's gracious formal dining room provides an elegant setting for memorable occasions. At the heart of the residence, an expansive great room seamlessly integrates a gourmet kitchen, casual dining area, custom bar and inviting natural gas fireplace. Framed by captivating waterfront views, this exceptional gathering space offers the ideal balance of luxury, comfort and functionality. The main-level primary suite serves as a private sanctuary, offering serene views of Lake Down and a beautifully appointed en-suite bath featuring dual vanities, two spacious walk-in closets, a luxurious jetted soaking tub and an oversized travertine shower. An additional main-level bedroom provides exceptional versatility, ideally suited for guest accommodations, a private executive office, fitness studio or creative retreat. Upstairs, two generously proportioned bedrooms provide additional privacy and comfort. Thoughtfully reconfigured from the home's original three-bedroom upper-level layout, one of these bedrooms has been transformed into an exceptionally spacious retreat, complete with its private balcony. Abundant storage throughout the residence, a spacious laundry room with a recently updated washer and dryer, and a three-car garage further enhance the home's everyday convenience. Beyond the interiors, an extraordinary outdoor oasis awaits. An expansive covered and screened lanai, custom swimming pool, lush, mature landscaping and picturesque waterfront surroundings create a private resort-inspired setting. Whether hosting elegant outdoor gatherings, enjoying a leisurely afternoon poolside, or simply taking in the tranquil beauty of the lake, every moment invites relaxation and enjoyment. For boating enthusiasts, the property's enclosed boathouse offers a distinctive waterfront amenity, featuring a protected boat area and an inviting screened retreat. With direct access to the 13 interconnected lakes of the Butler Chain, an exceptional lifestyle of boating, waterskiing, wakeboarding, paddleboarding and waterfront exploration awaits just beyond your doorstep. Adding to its appeal is the timeless charm of Windermere itself. Enjoy the town's celebrated weekly farmers market, boutique shops, inviting restaurants, local brewery, wine market and cherished community events. All this is complemented by convenient access to Orlando's premier shopping, acclaimed dining destinations, world-renowned attractions and Orlando International Airport.

Magnificent Waterfront Sanctuary on Lake Hart Tucked away behind the gates of the premier golf community of North Shore at Lake Hart, this custom-built estate delivers the ultimate Florida waterfront lifestyle on a private, oak-shaded 1.11-acre parcel. Offering 5,370 square feet of impeccably maintained living space, the home pairs classic architectural elegance with modern upgrades, including a newly replaced 2026 A/C unit for the main living quarters and bedrooms, professional interior repainting, a whole-home mesh Wi-Fi network, and kitchen remodel. Designed for effortless entertaining, the interior showcases soaring 14-foot ceilings, engineered hardwood floors, and a gorgeous living room anchored by a warm fireplace. Culinary enthusiasts will appreciate the reimagined chef's kitchen, fully equipped with a suite of brand-new high-end appliances including a Thermador double oven and refrigerator, Sharp microwave, and Bosch dishwasher. The expansive great room features 10-foot picture windows framing tranquil water views, flowing seamlessly out to the covered lanai. The main-floor primary suite serves as a true private retreat, complete with expansive lake vistas, custom walk-in closets, and a spa-inspired ensuite bathroom featuring a striking Restoration Hardware chandelier and Italian-crafted drapery. Three additional generously sized ensuite bedrooms (including an upper-level flexible suite) and a dedicated home office round out the interior. Step into your private backyard resort boasting a 625-square-foot covered outdoor living space with a fully outfitted summer kitchen, and an upgraded saltwater pool and hot tub system featuring a new propane heater, heat exchanger, Pool system with new piping and filters installed August 2026, and automated Hayward Salinator. Down at the water, a premium composite Trex dock provides direct access to Lake Hart and comes outfitted with a 15,000 lb covered boat lift with an automatic drop-down cover, dual aluminum jet-ski lifts, and dual swim platforms. Making this the largest dock on the lake. Positioned for ultimate convenience, this property places you just moments from the neighborhood North Shore Golf Club and daily shopping at Publix. Furthermore, it offers rapid access to the cutting-edge medical infrastructure of Lake Nona Medical City, including the Orlando VA Medical Center, Nemours Children's Hospital, and UCF Lake Nona Hospital. Families will also appreciate being served by top-rated local schools, including Moss Park Elementary (GreatSchools 9/10), Innovation Middle School (GreatSchools 9/10), and Lake Nona High School (GreatSchools 7/10). An exceptional lakefront opportunity, schedule your exclusive private tour today.

Set behind the gates of Windermere Club, this extraordinary lakefront estate presents a rare opportunity to experience refined luxury on the shores of Lake Crescent. Situated on a pristine one-acre homesite, this custom-built residence was thoughtfully crafted in 2015 to blend contemporary sophistication with timeless architectural elegance. Fresh exterior and interior paint enhance the home's striking architectural presence and timeless appeal. Encompassing nearly 9,000 square feet of impeccably designed living space, the home features seven bedrooms, seven full baths and one half bath, offering an exceptional balance of grandeur and comfort. Soaring 12-foot ceilings on the main level, 10-foot ceilings upstairs and elegant eight-foot doors enhance the home's impressive architectural scale. Expansive windows and doors frame breathtaking panoramic lake views, flooding the interiors with natural light and creating a seamless connection between indoor and outdoor living. The dramatic great room showcases polished travertine flooring, designer lighting fixtures and stunning vistas at every turn. Designed to inspire culinary excellence, the gourmet kitchen is appointed with professional-grade appliances, a handcrafted wine display, an oversized granite island and an expansive walk-in pantry. Adjacent gathering spaces include an elegant dining room and a welcoming family room. Outdoor living is equally impressive, featuring a resort-style heated swimming pool with a new pool pump, a fully equipped summer kitchen and expansive entertaining areas overlooking the water. An automated mosquito misting system enhances year-round enjoyment of the outdoor spaces. The residence offers first-floor and second-floor primary suites, four additional en-suite guest bedrooms, a private office, a theater room, a sophisticated bar and spacious balconies that capture spectacular sunrise views across the lake. The luxurious primary bath offers a steam room in the shower, creating a spa-inspired retreat within the comfort of home. Thoughtfully equipped with modern efficiencies, the property includes a 25-kW solar energy system with bidirectional metering, two 80-gallon solar-assisted water heaters, a whole-home water purification system, four HVAC systems, a recently installed septic drain field, an underground propane tank and a three-car garage. A private dock provides direct access to Lake Crescent, completing this exceptional waterfront lifestyle. Spanning approximately 187 acres, spring-fed Lake Crescent offers an exceptional setting for boating, waterskiing, fishing and watersports. Unlike the busier Butler Chain of Lakes, Lake Crescent provides a more intimate waterfront experience, combining recreational freedom with the tranquility and privacy of an exclusive lakefront retreat. Ideally situated within reach of Windermere and Winter Garden's premier shopping, dining and recreational destinations, this remarkable estate embodies the very finest in Central Florida lakefront real estate.