Windermere Homes with Lake Front Water Frontage

Windermere Homes with Lake Front Water Frontage

Welcome to Windermere, Florida, a picturesque gem nestled in the heart of Orange County. Known for its stunning lakes and serene landscapes, Windermere offers a unique blend of small-town charm and modern conveniences. With its vibrant community and lush surroundings, it’s no wonder that this enchanting locale has become a sought-after destination for homebuyers.

One of Windermere's most alluring features is its breathtaking lakefront properties. Imagine waking up to the gentle lapping of water against your dock, with panoramic views of the sparkling lakes right from your backyard. Homes with lakefront waterfrontage in Windermere provide not just a residence, but a lifestyle filled with tranquility and natural beauty. Whether you’re an avid fisherman, a water sports enthusiast, or someone who simply enjoys the calming presence of water, these properties offer a perfect gateway to endless outdoor adventures.

The town is also home to top-rated schools, exquisite dining options, and boutique shopping, ensuring that residents have access to all the amenities they need. Windermere’s close-knit community hosts various events throughout the year, fostering a welcoming atmosphere that makes it easy to feel at home.

Explore the charm of Windermere and discover the exceptional lakefront homes that await you. Here, every day feels like a vacation, and the beauty of nature is just outside your door. Embrace the lakeside lifestyle in Windermere, where your dream home is not just a house, but a sanctuary.

Newest Windermere Homes with Lake Front Water Frontage

9601 Ambleside Drive, Windermere
$1,160,000
4 Beds ⋅ 3 Baths ⋅ Lake Down Shores Rep SubDv. ⋅ 34786 Zip Code
Virtually Staged. Move in. Reimagine. Or build new. Welcome to the Lake Down Shores lifestyle, where one-acre homesites and private community access to the Windermere Chain of Lakes offer a special opportunity. Set on a beautiful corner lot just a few homes from the lake, 9601 Ambleside Drive offers something increasingly difficult to find: a move-in-ready home today, an exceptional amount of land, and the flexibility to imagine something entirely different for the future. Situated on a full, flat acre, the property offers a generous front yard while still leaving an enormous backyard with incredible possibilities. Offering more than 3,000 square feet of single-story living, 4 bedrooms, 2.5 baths, and garage parking for four vehicles, the home has been refreshed with a roof replaced in 2021, one of two HVAC systems replaced in 2022, new interior and exterior paint, lighting and fixtures, updated bathrooms, new door hardware, new front door, new carpet in many rooms, plumbing updates, new water softener, and new water heater. Generously sized rooms and an interconnected floor plan make this a wonderful home for entertaining. Wood flooring complements the main gathering areas, while expansive near-floor-to-ceiling windows and Solatubes bring in abundant natural light. The family room connects to the kitchen and air-conditioned Florida room, which features casement windows and plantation shutters. Updated in 2020, the kitchen features abundant cabinetry with wood pull-out drawers, a large island, quartz countertops, stainless-steel Samsung and LG appliances, and a glass-top convection range. The spacious primary suite features an ensuite bath and walk-in closet, plus French doors leading to a flexible bonus room ideal for a home office, nursery, or sitting room. Three additional bedrooms are also generously sized, and a large laundry room provides additional storage. What truly distinguishes this property is the opportunity it presents. Enjoy the beautifully refreshed residence today, reimagine the existing home through a comprehensive transformation, or create an entirely new custom residence on this exceptional one-acre homesite. Additional features include a 2-car attached garage plus a separate 2-car detached garage, dedicated irrigation well, and septic system pumped in April 2026. Lake Down Shores residents enjoy access to the community’s private HOA boat ramp onto the Windermere Chain of Lakes. The seller, an experienced luxury home builder, has already developed concepts specifically for the property, including plans for both a complete renovation of the existing residence and new construction. These concepts offer a compelling vision of what this remarkable homesite could become while letting the next owner choose the path that best reflects their lifestyle. Conceptual plans are available for review and are presented for inspiration only; future improvements and construction are subject to applicable governmental and HOA approvals. To experience the builder’s design aesthetic, finishes, and portfolio of completed residences, please ask to view Web Link 1.

9601 Ambleside Drive, Windermere

5650 Nectarine Drive, Windermere
$1,475,000
5 Beds ⋅ 5 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code
NEWLY BUILT HOME WITH LAKE CAWOOD ACCESS ON APPROXIMATELY 1.70 ACRES! Discover refined lake living in this Ashton Woods Duval residence in Lake Cawood Cove, Windermere, with the opportunity to build your own PRIVATE BOAT DOCK. With approximately 3,612 square feet of living space, 5 BEDROOMS, 4 FULL BATHROOMS, 1 HALF BATHROOM, and a 3-CAR TANDEM GARAGE, this home combines generous space with thoughtfully selected upgrades. 10-FOOT CEILINGS ON THE FIRST FLOOR, 9-FOOT CEILINGS ON THE SECOND FLOOR, and 8-FOOT DOORS enhance the spacious feel. NEW LUXURY VINYL PLANK FLOORING extends throughout the home, including the staircase, while the bathrooms and laundry room feature tile flooring. The impressive great room features a SOARING 2-STORY CEILING, creating an open, airy atmosphere that connects seamlessly to the GOURMET KITCHEN and breakfast area. Designed for everyday enjoyment and entertaining, the kitchen features a SPACIOUS ISLAND, an upgraded appliance package, UPGRADED CABINETRY, additional storage cabinets at the back of the island, and a customized pantry layout. A separate dining room provides space for special gatherings. The FIRST-FLOOR BEDROOM SUITE includes a closet and private full bathroom, creating a comfortable retreat for guests. Upstairs, the spacious PRIMARY SUITE features a TRAY CEILING, a LARGE WALK-IN CLOSET, and a private bathroom with separate vanities and a walk-in shower. An additional bedroom suite includes its own full bathroom, while 2 more bedrooms share another full bathroom. A versatile LOFT and conveniently located laundry room complete the second floor. Carefully selected enhancements include UPGRADED BATHROOM TILE with wall tile extending to the ceiling, upgraded toilets, LIGHTING UPGRADES, and wood stair railings. Additional features include sound insulation in selected walls, FOAM INSULATION in the block walls of the living space and garage, and prewiring for ceiling fans, security, and 2 additional wireless access points. An UPGRADED FRENCH DOOR opens to the COVERED LANAI, creating an inviting connection to outdoor living. SUMMER KITCHEN PLUMBING AND ELECTRICAL PROVISIONS provide the flexibility to customize your outdoor entertaining space. A conservation area toward Lake Cawood provides a peaceful, natural backdrop. Enjoy convenient access to Windermere Preparatory School, Windermere High School, Publix, Aldi, shopping, dining, Winter Garden Village, the 429 Expressway, and world-famous theme parks. With its desirable Windermere location, stylish finishes, and spacious layout, this newly built home provides an exceptional opportunity to enjoy the Florida lifestyle. Schedule your private showing today! VIDEO, 3D TOUR, AND FLOOR PLAN LINKS ABOVE.

5650 Nectarine Drive, Windermere

12620 S Lake Sawyer Lane, Windermere
$3,250,000
4 Beds ⋅ 6 Baths ⋅ Acreage SubDv. ⋅ 34786 Zip Code
Finding a MODERN, CUSTOM-BUILT LAKEFRONT HOME in Windermere, set on 1.15 ACRES with NO HOA or CDD, is an increasingly rare opportunity. Add exceptional PRIVACY, your own PRIVATE BOAT DOCK with TWO BOAT LIFTS, extensive high-end upgrades and beautiful lake views, and this home truly stands apart. Offering approximately 4,200 square feet of thoughtfully designed living space, this striking contemporary residence combines luxurious finishes with an effortless indoor-outdoor lifestyle, all within minutes of Windermere's everyday conveniences. From the moment you enter, the home's clean architectural lines, expansive windows and natural light create an immediate sense of space and connection to the outdoors. Beautiful PORCELAIN TILE flooring flows throughout the main level, while warm WOOD FLOORING upstairs complements the modern design. At the heart of the home is a stunning GOURMET KITCHEN featuring contrasting granite countertops, extensive CUSTOM BLUM BIRCH CABINETRY with premium aluminum detailing, and an impressive suite of WOLF APPLIANCES, including a six-burner gas range top, convection steam oven, dual-fan convection oven and warming oven. A built-in coffee station, generous pantry storage and cleverly concealed cabinetry complete this exceptional space. The adjoining living area is anchored by a dramatic 72-INCH GAS FIREPLACE, creating an inviting setting for both everyday living and entertaining. The MAIN-FLOOR PRIMARY SUITE is a peaceful retreat, with large windows framing beautiful lake views and direct access to the lanai. Two separate custom-fitted walk-in closets provide exceptional storage, while the luxurious en-suite bathroom features a freestanding soaking tub, separate oversized shower, dual vanities and elegant FLOOR-TO-CEILING PORCELAIN TILE. Upstairs, THREE ADDITIONAL EN-SUITE BEDROOMS provide excellent privacy and comfort for family and guests. The expansive LOFT area offers an additional living and entertaining space, complete with a fitted kitchenette, granite countertops and wine cooler. Multiple oversized patio doors open onto both a front balcony and a generous REAR TERRACE OVERLOOKING THE LAKE, creating a wonderful setting for morning coffee, evening drinks or simply enjoying the peaceful surroundings. Outside, the lifestyle is every bit as impressive. Approximately 80 FEET OF LAKEFRONT, a PRIVATE DOCK WITH TWO BOAT LIFTS and a beautifully secluded setting create your own waterfront escape. The spacious LANAI features MOTORIZED SCREENS, allowing indoor and outdoor living to flow seamlessly together. There's also ample room to create a spectacular POOL AND OUTDOOR ENTERTAINING AREA if desired. And as the sun goes down, enjoy views of the DISNEY FIREWORKS illuminating the evening sky. Beyond its beautiful design, this home has been built and equipped with exceptional attention to quality, comfort and efficiency. Notable features include IMPACT INSULATED WINDOWS AND DOORS, enhanced interior insulation, a WHOLE-HOUSE NATURAL GAS GENERATOR, TWO RINNAI TANKLESS WATER HEATERS, motorized window shades, extensive custom storage and a THREE-CAR GARAGE with insulated doors and RHINO garage storge shelves. The generous homesite also offers potential for future expansion. Perfectly positioned in WINDERMERE, the property offers a rare combination of PRIVACY, WATERFRONT LIVING and everyday convenience, with easy access to shopping, dining, schools, major roadways and Orlando's world-famous attractions.

12620 S Lake Sawyer Lane, Windermere

6518 Sawyer Shores Lane, Windermere
$2,190,000
5 Beds ⋅ 6 Baths ⋅ Sawyer Shores Sub SubDv. ⋅ 34786 Zip Code
Virtually Staged. Under Construction. Estimated completion: January 2027. Commanding architecture, soaring interiors and access to Lake Sawyer define this new contemporary residence in sought-after Windermere. Set on a wide 0.39-acre lot, its striking facade makes an immediate impression, while approximately 100 feet of canal frontage opens the door to a lifestyle on the water. As the first home along the canal from the lake, the property enjoys a short waterway connection to Lake Sawyer, with an existing floating platform designed for a personal watercraft. Offering 3,582 square feet of conditioned living space and 4,865 total square feet, the home features five bedrooms, each with an en-suite bathroom, plus a powder room, dedicated office and three-car garage. Twelve-foot ceilings on both floors and a dramatic double-height space create an exceptional sense of scale. The open layout connects the kitchen, dining and living areas for effortless everyday living and entertaining, while the main-floor primary suite offers a comfortable retreat with a walk-in closet and spacious bathroom. Extensive cabinetry and built-ins bring a tailored aesthetic throughout the home. Planned finishes include stone countertops, porcelain tile and warm wood-look flooring, complemented by a gas cooktop and an electric fireplace. The design balances contemporary presence with inviting spaces that feel comfortable to live in. Outside, a private heated pool and covered rear lanai with a grill and sink set the scene for relaxed afternoons and evenings with guests. Planned artificial turf around the pool, hardscape surfaces and landscaping complete an outdoor setting designed for enjoyment with easy upkeep. With no HOA, this property pairs the appeal of new construction with a waterfront setting close to the lake. Within walking distance of Windermere Preparatory School, ranked No. 1 among private high schools in Orange County by Niche for 2027, and conveniently located near Windermere High School. Public schools listed for this address are Windermere Elementary, Bridgewater Middle and Windermere High, all earning an A in Florida's 2026 school grades. Buyers should verify current school zoning. Limited personalization may be considered, subject to builder approval and construction timing. Discover a home where the arrival is memorable, the interiors feel expansive and time on Lake Sawyer can become part of everyday life. Images include architectural renderings and virtual staging; final materials and finishes may vary.

6518 Sawyer Shores Lane, Windermere

12785 Westside Village Loop, Windermere
$769,000
4 Beds ⋅ 4 Baths ⋅ Westside Village SubDv. ⋅ 34786 Zip Code
NEW PRICE! MOVE-IN READY WINDERMERE HOME WITH PEACEFUL CONSERVATION VIEWS + $12,000 DECOR/RATE BUY DOWN CREDIT! Discover the perfect blend of comfort, style, and location in desirable Westside Village! This beautifully maintained 4-bedroom, 3.5-bath home features an inviting open-concept floor plan, classic tile roof, professionally landscaped yard, and spacious front porch. Enjoy tranquil conservation views from the backyard, creating a peaceful backdrop for relaxing or entertaining. The light-filled kitchen is designed for everyday living and effortless entertaining, featuring granite countertops, stainless steel appliances, and an oversized center island with abundant storage and seating. The kitchen flows seamlessly into the living room and breakfast nook, while French doors open to the patio for easy indoor-outdoor living. Enjoy a $12,000 decor credit toward a flooring upgrade and EV charger, offering an opportunity to personalize your home and add modern convenience. Westside Village offers an exceptional lifestyle with resort-style amenities, including a community pool, clubhouse, playground, paved walking trails, and scenic water features. Conveniently located near top-rated schools, shopping, dining, major highways, and just minutes from Walt Disney World, this home combines peaceful surroundings with easy access to everything Central Florida has to offer.

12785 Westside Village Loop, Windermere

8576 Powder Ridge Trail, Windermere
$620,000
4 Beds ⋅ 4 Baths ⋅ Windermere Trails SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this exceptional, energy-efficient modern residence built in 2017, perfectly positioned with tranquil lake views in one of the area’s most desirable neighborhoods. Offering a spacious and thoughtfully designed main home alongside a full apartment—ideal as a private guest suite or a lucrative rental income opportunity—this property delivers unmatched versatility and lifestyle appeal. The main home features an expansive open-concept layout designed for daily living and sophisticated entertaining. The bright, airy living and dining area flow seamlessly into a modern kitchen, equipped with premium stainless steel appliances, abundant counter space, and extensive storage. A second family room offers additional possibilities for entertaining and comfort. Upstairs, the spacious primary suite features a dual-sink vanity and a walk-in shower. Two additional well-sized bedrooms offer exceptional flexibility for family, guests, or a home office. A large balcony spans the entire width of the home on both stories. A standout feature of this property is the fully independent detached granny flat, complete with its own kitchenette, bedroom, living room and full bathroom. Whether utilized for multi-generational living, visiting family, or leased out for steady rental income, this private space adds extraordinary value. Additional highlights include a secure two-car garage and patio. Situated in a vibrant community, residents enjoy resort-style amenities including a sparkling pool overlooking the lake, a dedicated dog park, playgrounds, scenic walking trails, and a picnic pavilion. This home boasts a few minute walk from top-rated schools, including Bay Lake Elementary, Horizon West Middle School and Windermere High School. This prime, highly sought-after location is just a few minute drive from historical downtown Windermere, equipped with charming boutiques and picturesque views, and in close proximity to top shopping and dining at Lakeside Village and Winter Garden Village, as well as world-famous Orlando attractions including Disney, Universal Studios, and SeaWorld. A rare find combining modern 2017 construction, income potential, and a premium neighborhood setting—schedule your private tour today!

8576 Powder Ridge Trail, Windermere

8229 Tibet Butler Drive, Windermere
$1,999,000
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Gracious Golf-Course Living in Keene’s Pointe . Welcome to an exceptional retreat in the prestigious, 24-hour guard-gated community where refined interiors, resort-style outdoor living and the coveted Windermere lifestyle come together beautifully. Perfectly positioned on 0.35 acres overlooking the 8th fairway of The Golden Bear Club’s Jack Nicklaus Signature golf course, this extensively updated 4-bedroom, 4-bath residence offers 3,912 square feet of living space designed for both elegant entertaining and comfortable everyday living. From the moment you enter, thoughtful upgrades and sophisticated finishes set the tone. Rich wood floors, designer lighting, custom window treatments and beautifully renovated living spaces flow into the heart of the home: a show-stopping gourmet kitchen featuring quartz countertops, an impressive 9-foot island, six-burner gas cooktop, wine refrigerator and stand-alone ice maker. Whether hosting a celebration or enjoying a quiet evening at home, this kitchen was made to gather around. The home's flexible floor plan is one of its greatest luxuries. Three bedrooms and three full baths are conveniently located on the first floor, including an expansive primary suite with a spa-inspired bath, oversized walk-in jetted shower and spectacular 12x14 ft. closet. A generously sized secondary primary bedroom features its own en-suite bath, while a dedicated home office with French doors provides a private and polished work-from-home environment. Upstairs becomes a retreat of its own, with a spacious bonus/gathering room, full bath and large bedroom accommodating two queen beds—an ideal arrangement for extended family, older children, visiting guests or a private second living area. Then step outside to your own Florida resort. The screen-enclosed Gunite pool has been completely resurfaced with new inset tile and is complemented by a new pool heater, pump and motor. A covered outdoor kitchen and bar invite year-round entertaining, the perfect setting for evenings under the stars—all framed by peaceful views across the golf course. And the improvements go far beyond what you can see. Recent investments include a new Carrier HVAC system with Wi-Fi-enabled Ecobee smart thermostats and UV systems, a refurbished whole-house Briggs & Stratton generator, enhanced landscape lighting, whole-house water purification, automated electric blinds in the primary suite, an EV charging outlet and overhead garage storage. Country Club living at its membership opportunities at The Golden Bear Club offer golf, tennis, fitness, swimming, dining, clubhouse amenities and an active social lifestyle. This is more than a beautifully renovated home. It is a thoughtfully designed sanctuary offering the space to gather, the privacy to retreat, and an extraordinary setting in which to enjoy the very best of Windermere living. Turnkey luxury. Golf-course views. Resort-style outdoor living. Welcome home to Keene’s Pointe.

8229 Tibet Butler Drive, Windermere

9602 Maywood Drive, Windermere
$4,350,000
5 Beds ⋅ 5 Baths ⋅ Lake Down Shores SubDv. ⋅ 34786 Zip Code
Welcome to 9602 Maywood Drive, a privately gated lakefront estate on Windermere's prestigious Butler Chain of Lakes. The home was reimagined through a renovation of more than $1 million by the award-winning firm KBF Design Gallery, and every detail was carefully considered. From dawn to dusk, the estate looks out over unobstructed sunrises and sunsets on Lake Down, the Butler Chain’s Northernmost lake known for crystal-clear water and premier largemouth bass fishing. As evening falls, it offers front-row views of the Walt Disney World and Universal Studios Orlando fireworks. Oversized custom steel-and-glass doors open to a grand foyer with soaring 26-foot ceilings. Overhead hangs a statement designer chandelier, mounted on a lift system for easy upkeep. Beyond it, Lake Down comes into view through walls of glass and draws you into light-filled living spaces. They are open and airy, yet warm and thoughtfully designed. At the heart of the home, the chef's kitchen is built for both everyday living and grand entertaining. It features a full Thermador appliance suite, a built-in GE Monogram pizza oven, two additional ovens including a speed oven, gas range, a warming drawer, a prep sink, and extensive custom storage. Next to it, a handsomely appointed bar offers generous wine storage, a sink, and an ice maker. It's an ideal setting for hosting guests. The main level includes a comfortable family room, an elegant dining area, a laundry room, and a guest bedroom and full bath. The primary suite is privately set apart on this floor and has dedicated his-and-hers closets. Its open, spa-inspired bath includes a deep soaking tub, a multi-head shower, a vanity, and a private water closet. Upstairs are three additional bedrooms, each with its own en-suite bath, along with a second living area and an impressive private theater. Outdoors, a resort-style retreat invites relaxed living in every season. It has a sparkling saltwater pool, a fully equipped summer kitchen, generous spaces to lounge and dine, and expansive, manicured green space. The renovated two-story dock featuring a hydraulic boat lift is made for fishing, boating the chain, or simply enjoying the view over the clear waters of Lake Down. The HOA free estate also includes smart-home technology for everyday convenience, exterior IP camera system with High Res cameras, gated access to the property, a new tile roof (2024), four AC units, and two hot-water heaters. There's a three-car garage with ample on-site parking, no HOA, and zoning for A-rated schools. A turnkey lakefront estate of this caliber is a rare find in Windermere, just minutes from Orlando's finest dining, shopping, and attractions.

9602 Maywood Drive, Windermere

1221 Oakdale Street, Windermere
$1,250,000
Windermere Town SubDv. ⋅ 34786 Zip Code
Build Your Dream Lakefront Home in the Town of Windermere! Opportunity is knocking in one of Central Florida’s most desirable areas! This exceptional one-acre lakefront homesite on Oakdale Street in the town offers a rare opportunity to bring your vision to life and build the custom home you have always dreamed of. With an impressive 105 feet of direct frontage on beautiful Lake Bessie, this property provides the space, privacy, and waterfront setting to create something truly special. One of the biggest advantages of this property is NO HOA. Enjoy the freedom and flexibility that comes with owning your own piece of land without the restrictions and monthly fees often associated with planned communities. Whether you envision a stunning custom estate, a spacious family home, or a private lakeside retreat, this property gives you the opportunity to create a home that is uniquely yours. The expansive one-acre lot provides plenty of room to design the lifestyle you want. Imagine a beautiful custom residence with expansive living spaces, a resort-style pool, outdoor entertaining areas, lush landscaping, a private garden, oversized garage, and breathtaking views of Lake Bessie. With 105 feet of lake frontage, you can take full advantage of the waterfront setting and enjoy the beauty and tranquility of lakefront living right in the heart of Windermere. Instead of settling for someone else’s floor plan, start with a blank canvas and create a home designed around the way you live. Bring your architect, builder, and ideas and transform this exceptional homesite into your own private sanctuary. Location is everything, and this property offers the best of the Old Windermere lifestyle. Ideally located within a short distance of the Windermere Farmers Market, local shops, restaurants, and more, while beautiful Lake Butler is just blocks away. Town residents also have access to a boat ramp on Lake Butler and Lake Bessie, along with tennis courts, providing even more opportunities to enjoy the outdoors and the unique lifestyle that makes Windermere so desirable. Windermere is known for its beautiful lakes, charming community atmosphere, desirable residential neighborhoods, and convenient proximity to everything that makes Central Florida such a sought-after place to live. Opportunities to own a large lakefront homesite with no HOA and 105 feet of Lake Bessie frontage are truly special. This is your opportunity to stop dreaming about the perfect home and start building it. Make your vision come to life. Make this exceptional Windermere lakefront property the place you call home. Don't miss this rare opportunity!

1221 Oakdale Street, Windermere

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