4 Beds ⋅ 4 Baths ⋅ Casa De Lago Rep SubDv. ⋅ 34786 Zip Code

Original-owner David Weekley Mediterranean in gated Casa Del Lago, on the coveted east side of Windermere near Isleworth and Keenes Pointe, minutes from Walt Disney World and an easy walk to Sunset Park Elementary.From the moment you step inside, rich hardwood floors draw you through the study, formal dining room, family room, and primary suite, giving the home a warmth and continuity rarely found at this price point. The gourmet kitchen is the heart of it all, with 42" cabinetry, granite counters, a cooktop crowned by a designer vent hood, and stainless GE appliances, all open to the family room so no one misses the conversation. Sliders lead to an expansive covered lanai and a generous backyard with plenty of room for a pool, a garden, or simply space to breathe. A 3-car garage handles vehicles, toys, and storage with ease. Cared for by a single owner since David Weekley handed over the keys, this home delivers the Windermere address buyers are searching for. Gated privacy, top-rated schools, and Winter Garden Village shopping and dining are all minutes away, with quick access to the 429 and the charm of Downtown Windermere.

7230 Sangalla Drive, Windermere

$1,100,000

4 Beds ⋅ 4 Baths ⋅ Summerport Ph 02 SubDv. ⋅ 34786 Zip Code

Rare Windermere opportunity with water on TWO sides... Direct waterfront on one, and premium scenic water views on the other. Set on a premium 1.08-acre homesite with pond access and only one neighboring residence, this 4-bedroom, 4-bath home offers privacy, panoramic views, a private pool and spa, and nearly 3,400 square feet of living space. With more than $70,000 in recent improvements, the property combines an expansive indoor layout with exceptional outdoor living. Inside, soaring ceilings, designer finishes, and a grand staircase create a striking first impression. Designed for both everyday living and entertaining, the home features two spacious living areas, a well-appointed kitchen, formal dining room, butler’s pantry, dedicated office, and a custom home theater. Outfitted with a Sony 4K projector, Philips 110-inch film screen, Dolby Atmos surround-sound speakers, and seating for eight, the theater delivers an exceptional cinematic experience at home. Recent improvements include fresh interior paint, custom accent walls, a striking fireplace feature wall, updated designer lighting, a built-in Sub-Zero/Viking refrigerator, an undercounter ice maker, and reverse-osmosis water filtration. Additional highlights include a 2021 architectural roof and gutters, two HVAC systems replaced in 2020, and a split three-car garage with a climate-controlled third bay currently configured as a fitness space. Step outside to a private waterfront retreat with a pool and spa, stone firepit, expansive brick-paver lanai, and custom MegaView screen enclosure. The outdoor setting showcases panoramic water views with minimal visual obstructions, while the spacious driveway and welcoming front porch add to the home’s functionality. The backyard also provides views of Disney fireworks. Summerport amenities include a neighborhood park, playground, community beach, dock, walking and biking paths, clubhouse, community pool, fitness center, tennis and basketball courts, and gathering spaces. This Windermere residence offers a rare combination of acreage, privacy, direct waterfront, scenic water views, and resort-style outdoor living.

14038 Bluebird Park Road, 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

$1,189,000

5 Beds ⋅ 5 Baths ⋅ Enclave SubDv. ⋅ 34786 Zip Code

WATER VIEW! DISNEY FIREWORKS! 4,999 SQ FT OF LIVING SPACE! TWO PRIMARY SUITES, ONE ON EACH FLOOR! 3 CAR GARAGE! Located in the desirable Enclave community of Windermere, this spacious 5 bedroom home offers an exceptional floor plan with a primary suite on the first floor and a generously sized primary retreat upstairs. Highlights include expansive living areas, formal dining room, private office, dedicated Media Room, and a large upstairs Loft, offering plenty of space for entertaining, relaxing, and everyday living. The spacious kitchen features a pantry and ample storage, complemented by a covered lanai overlooking the water. A well designed Mudroom with extensive custom cabinetry and generous storage, plus a central vacuum system, adds everyday convenience. Beautifully maintained, this residence combines generous living space, comfort, and versatility, with excellent potential to personalize its interiors to your own style. Enjoy the best of Windermere living with beautiful water views, Disney fireworks in the distance, and an exceptional combination of space, functionality, and location.

17538 Black Rail Street, Windermere

$1,050,000

4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

AVAILABLE FOR SALE OR LEASE. Keene's Pointe, 24-hour gated/attended golf community. Tucked adjacent to the Butler Chain of Lakes this home offers 4 bedrooms, 3 baths, formal living and dining and an office/den. As you enter this one level home you will find 3-way split functional plan. Boasting the primary ensuite separate from the three additional bedrooms with a spacious bath and TWO WALK-IN CLOSETS, and access to the covered/screened lanai. Spacious kitchen with an abundance of cabinetry, convenient desk area and island. Newer stainless Steel appliances. The kitchen, dinette and great room feature two sets of French doors that give way to the covered screened lanai and back yard. Beyond the screened lanai is an oversized paved patio and custom pergola seating. Privacy is included with the 6 ft vinyl fence. New Roof ('20), AC units(’18/’19), Hot Water Heater (’21/Natural Gas), Exterior Paint(’20) Shallow well for irrigation, termite bond, 5 Camera Ring System (8/21) including Flood lights and doorbell, expanded paver driveway (2025) for additional parking, blinds and plantation shutters, central vacuum system, and new septic pump('22) are just a few of the great features of this home. Located close to dining, shopping, expressways, tourist attractions, and top-rated public and private schools, this home and community has it all!

5944 Caymus Loop, Windermere

2009 Westover Reserve Boulevard, Windermere

$1,095,000

4 Beds ⋅ 4 Baths ⋅ Westover Reserve Ph 02 SubDv. ⋅ 34786 Zip Code

ELEGANCE, PRIVACY & EXCEPTIONAL OUTDOOR LIVING IN GATED WESTOVER RESERVE. Beautifully maintained custom residence set on approximately half an acre in one of Windermere’s desirable gated communities. From the moment you arrive, the property makes an impression. The expansive front yard is framed by mature landscaping and established greenery, creating a welcoming sense of privacy and a beautiful approach to the home. The generous lot provides a rare feeling of space and separation that is increasingly difficult to find in Windermere. The front and rear grounds are equally impressive, with generous lawn areas, established landscaping and mature vegetation creating a sense of scale, privacy and tranquility. The backyard is an extraordinary private retreat, with expansive green space and peaceful conservation views providing a beautiful natural backdrop. The screened outdoor living area surrounds a private pool, offering an ideal setting for relaxing, entertaining and enjoying the Florida lifestyle with no neighbors in the back. The combination of the oversized yard, conservation setting, mature landscaping and pool area creates an outdoor environment that feels exceptionally private and resort-like. Inside, the approximately 3,678-square-foot residence offers an inviting combination of refined architectural details, thoughtful updates and comfortable Florida living. Soaring ceilings, abundant natural light and thoughtfully designed living spaces create an impressive yet warm atmosphere. The formal living and dining areas provide elegant spaces for entertaining, while the spacious family room, complete with a gas fireplace, serves as a comfortable gathering area. The beautifully redone kitchen blends style, functionality and modern technology, featuring updated cabinetry, stone countertops, a breakfast bar, pantry and brand-new appliances. The adjoining dining area provides an inviting setting for everyday meals and entertaining. The split-bedroom floor plan offers privacy, with the primary suite positioned as a relaxing retreat and additional bedrooms located on the opposite side of the home. The primary suite features high ceilings, a spacious walk-in closet, dual vanities, garden-style tub and separate shower, along with French doors providing direct access to the screened lanai. A dedicated office/den adds flexibility for work, study or additional living space, while the upstairs oversized bonus room provides another versatile area that can adapt to a variety of needs. Additional recent improvements enhance the home’s comfort, functionality and appeal, including a redone laundry room with state-of-the-art washer and dryer, new light fixtures throughout the home, a new water heater, new garage doors and a new irrigation system serving both the front and rear grounds. Additional highlights include a three-car garage, screened lanai, private pool and spa, roof replaced in 2017, and pool improvements including resurfacing and updated equipment. Located within gated Westover Reserve, this residence combines a substantial homesite, beautiful interior spaces, thoughtful modern updates and remarkable outdoor living in a highly desirable Windermere setting. A truly special property where space, privacy, elegance and exceptional Florida outdoor living come together.

2009 Westover Reserve Boulevard, Windermere

$1,159,000

4 Beds ⋅ 4 Baths ⋅ Westside Village SubDv. ⋅ 34786 Zip Code

Beautifully upgraded 4-bedroom residence featuring a thoughtfully designed floor plan, custom finishes, and exceptional indoor-outdoor living. The main level offers a private en-suite bedroom, ideal for guests or multigenerational living, along with a dedicated home office, spacious living areas, and a beautifully designed custom kitchen featuring tailored cabinetry, a large center island, integrated lighting, and generous storage. A separate TV/media room provides the perfect space for movie nights, entertainment, or relaxing with family. Upstairs, the spacious primary suite offers a private retreat with a truly special feature: Disney fireworks can be enjoyed right from the comfort of your bed. The suite also includes a generous walk-in closet and a spa-inspired primary bathroom featuring a freestanding soaking tub, dual vanities, and an oversized shower with separate his-and-hers shower fixtures. Extensive custom details can be found throughout the home, including Italian wallpaper, custom window treatments, bespoke cabinetry, decorative wall paneling, wood accents, designer lighting, and integrated LED lighting. Every element has been thoughtfully selected to create a comfortable contemporary interior. Designed for the Florida lifestyle, the outdoor living space features a spacious covered lanai with plenty of room for dining and lounging, overlooking the private heated pool and landscaped backyard. The seamless connection between the indoor and outdoor spaces makes this home equally suited for everyday living and entertaining. With a first-floor en-suite bedroom, dedicated office, media room, custom-designed kitchen, extensive interior upgrades, heated pool, and Disney fireworks views from the primary suite, this home offers an exceptional combination of style, comfort, and functionality. Thoughtfully customized and beautifully maintained, this is a home designed to be enjoyed inside and out.

12989 Westside Village Loop, Windermere

$1,204,990

6 Beds ⋅ 5 Baths ⋅ Palms At Windermere SubDv. ⋅ 34786 Zip Code

Virtually Staged. Under Construction. SWEETWATER H - Our beautiful huge 2 story home, located on a conservation lot, with 6 Bedrooms and 4.5 Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42" wrap around cabinets, and an extended island. The owner's bath also contains a spa package with upgraded 3/8" glass enclosure, an additional rainfall shower head, and wall niche. The living area has an extension to the room, 9' hidden sliding glass doors and a huge lanai that runs the width of the home. Downstairs flex room works well as an office or study. Upstairs, find 5 large bedrooms most with walk in closets, 3 full baths, and a second laundry room,(that's right! 1 upstairs, and 1 downstairs). Common areas upstairs include a spacious bonus room with wet bar, and a second flex room that works well as a theatre room. SAMPLE IMAGES

14213 Crest Palm Avenue, Windermere

$1,065,000

4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Virtually Staged. One or more photo(s) was virtually staged. *** BRAND NEW ROOF AUG 2026 *** This is your opportunity to own a home in Keene's Pointe, a 24-hour guard-gated golf community on the Butler Chain of Lakes and home to the Golden Bear Club. Built by David Weekley and proudly offered by its original owner, this 4-bedroom, 4-bathroom home offers 3,646 square feet of flexible living space, including a dedicated home office, a flex room, and a spacious upstairs bonus room that could serve as a potential fifth bedroom, media room, or game room. Upstairs is also equipped with a full bathroom. A tandem three-car garage provides room for multiple vehicles, a golf cart, additional storage, or a workshop area. Inside, the thoughtfully designed floor plan begins with a formal dining room and dedicated home office just off the foyer. A secondary bedroom and full bathroom are conveniently located near the front of the home, while the open-concept family room and kitchen create the heart of the home. The kitchen features a center island, cabinetry, and countertop space. There is an existing electric range, but the community is connected to natural gas, offering the option to convert the existing electric range. Sliding glass doors open to the covered lanai and private backyard, extending the living space outdoors. The spacious first-floor primary suite offers plenty of room for a sitting area or reading nook. The primary bathroom features dual vanities, a walk-in shower, garden tub, and a spacious closet. Two additional bedrooms are privately situated on the opposite side of the home and are separated by a flex room, making it ideal as a study area, hobby space, or additional sitting room. A full bathroom with direct access to the covered lanai completes this wing of the home. Residents of Keene's Pointe enjoy private boardwalks to Lake Tibet of the Butler Chain of Lakes, community boat ramp to Lake Burden, four playgrounds, scenic green spaces, and neighborhood events. Optional membership to the Golden Bear Club offers championship golf course, tennis, a swimming pool, fitness center, dining, and an active social calendar. In order to utilize these amenities, a Golden Bear Club membership is needed. Conveniently located near Walt Disney World, shopping, dining, everyday conveniences and services, this home offers an opportunity to enjoy the lifestyle and amenities of Keene's Pointe. Disclosure: Artificial Intelligence has been utilized in public remarks and removal of some personal property.

8344 Bowden Way, Windermere

$1,125,000

4 Beds ⋅ 3 Baths ⋅ Windermere Downs SubDv. ⋅ 34786 Zip Code

Welcome home to your own Florida retreat, nestled on a generous 0.74-acre lot along the canopy-shaded, oak-lined streets of highly sought-after Windermere Downs. With access to the famed Butler Chain of Lakes and an array of community amenities, this property offers a rare combination of privacy, space, and the Windermere lifestyle. Windermere Downs residents enjoy amenities such as a private beach recreation area with access to the Butler Chain of Lakes, complete with a boat ramp and dock, white sandy beach, roped-off swimming area, and playgrounds. Two additional neighborhood parks offer playgrounds and tennis courts, making it easy to enjoy everything this established community has to offer. A spacious paver driveway leads to the garages offering parking for four cars., while a flagstone walkway welcomes you through the double-door entry. Inside, the foyer opens to bright formal living and dining rooms framed by two large bay windows. The kitchen features travertine flooring, multiple French doors, stainless steel appliances, and a gas range, with convenient access to the dining and family rooms. The inviting family room centers around an authentic Old Chicago Brick fireplace and features three skylights that bring in an abundance of natural light. The spacious primary suite offers a private retreat of its own, with French doors opening directly to the screened pool lanai. The en-suite bathroom is finished with a Kohler clawfoot tub and high-end fixtures. Beyond the living spaces, the backyard is a private oasis surrounded by mature greenery. A screened-in pool with travertine decking provides the perfect place to relax, while the expansive open travertine patio offers plenty of room for gatherings and outdoor dining. Additional features include a whole-house propane generator, 1,000-gallon underground gas tank, hybrid water heater, irrigation well, and valuable 2026 updates including a whole-house re-pipe, fresh exterior paint, and new soffits. With an expansive homesite, four-car garage, pool, and coveted Windermere Downs amenities, this is Florida living at its best.

2009 Woody Drive, Windermere

$1,250,000

4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Nestled on a quiet cul-de-sac in the desirable Hamilton Village section of Keene's Pointe, this beautifully maintained one-story Golf Villa offers the perfect blend of comfort, elegance, and low-maintenance living. Featuring 4 bedrooms, 3 bathrooms, and nearly 2,900 square feet of thoughtfully designed living space, this residence showcases extensive hardwood flooring, upgraded cabinetry, granite countertops, a whole home Kinetico water filtration system and an inviting open layout ideal for both everyday living and entertaining. Recent improvements provide peace of mind and exceptional value, including a brand-new metal roof, new a/c unit and fresh interior and exterior paint, enhancing both the home's appearance and long-term durability. The spacious floor plan offers generous gathering areas filled with natural light, while the well-appointed kitchen opens seamlessly to the main living spaces. The private primary suite provides a relaxing retreat, and the guest accommodations are thoughtfully positioned to offer comfort and privacy for family and visitors alike. Step outside to the screened lanai and enjoy Florida living year-round. Complete with a summer kitchen and fenced backyard, the outdoor space is perfect for dining, entertaining, or simply unwinding in a peaceful setting. Additional highlights include a two-car garage plus a dedicated golf cart garage, custom closet storage, and mature landscaping. Located within the 24-hour guard-gated community of Keene's Pointe, residents enjoy access to one of Central Florida's premier golf and lifestyle communities, with optional membership opportunities at The Golden Bear Club. Conveniently located near top-rated schools, dining, shopping, and major roadways, this exceptional Windermere home offers an outstanding opportunity to enjoy the Keene's Pointe lifestyle. Virtual Floorplan available.

6124 Foxfield Court, Windermere

$1,000,000

Willows At Lake Rhea Ph 03 SubDv. ⋅ 34786 Zip Code

Rare Waterfront Estate Opportunity in Windermere. Discover an exceptional opportunity to build your dream home on over 2.72 acres in the Willows at Lake Rhea community. This remarkable homesite offers approximately 150 feet of lake frontage and breathtaking water views from every angle. Enjoy the serenity of Lake Rhea in your backyard and a private pond in the front, creating a truly unique and picturesque setting. The property is enhanced by a 25-foot conservation buffer to the south, providing added privacy, while substantial brick privacy walls along the north and west boundaries further contribute to the estate-like atmosphere. Opportunities like this are seldom available—experience the setting in person to fully appreciate its beauty, privacy, and potential.

11544 Willow Gardens Drive, Windermere

Homes for Sale in Windermere, FL Between $1,000,000 to $1,250,000

All Windermere, FL Homes for Sale Between $1,000,000 to $1,250,000

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