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Windermere, FL Homes For Sale | Discover Your Dream Property with The Nest Group

Explore an exquisite selection ofhomes for sale in Windermere, FL,a highly sought-after Central Florida locale known for its Chain of Lakes,opulent residences,and top-tier lifestyle.From elegant waterfront estates to charming family homes in desirable communities like Isleworth and Keene's Pointe,Windermere offers diverse properties.Finding the perfect abode amidst this vibrant community requires local expertise.The Nest Group specializes in connecting discerning buyers with their ideal Windermere home,providing unparalleled insight into local market trends and exclusive listings.Begin your journey to owning a piece of this picturesque town,where luxury and convenience converge beautifully.

Why Windermere, FL Attracts Discerning Homebuyers

Windermere,Florida,consistently ranks among the most desirable places to live in Central Florida,makinghomes for salehere a prime investment for those seeking an elevated lifestyle.The town's unique charm,defined by its pristine lakes and lush landscapes,offers a serene escape while maintaining convenient access to metropolitan amenities.

The Chain of Lakes Lifestyle

At the heart of Windermere's allure are the stunning Butler Chain of Lakes.Many homes for salein this area boast direct lake access or breathtaking waterfront views,allowing residents to indulge in boating,fishing,and watersports right from their backyard.The lifestyle here is intrinsically tied to these magnificent waterways,offering unparalleled recreational opportunities.

Top-Rated Schools & Family Amenities

Families exploring homes for sale in Windermere will find reassurance in the area's commitment to education.The community is served by highly-rated public and private schools,contributing to its reputation as an excellent place to raise children.Furthermore,Windermere offers numerous parks,community events,and youth sports programs,fostering a vibrant family-friendly environment.

Proximity to Orlando Attractions

While enjoying the tranquility of Windermere,residents are never far from the excitement of Orlando.World-class theme parks like Walt Disney World and Universal Studios,upscale shopping,and diverse dining options are just a short drive away.This ideal balance of peaceful residential living and urban accessibility makesWindermere,FL homes for saleincredibly appealing.

Types of Homes for Sale in Windermere, FL

The real estate market in Windermere is remarkably diverse,catering to various tastes and budgets,though predominantly featuring luxury and upscale properties.Whether you're searching for an expansive estate or a modern family home,there are many exceptionalhomes for saleto consider.

Luxury Waterfront Estates

Windermere is synonymous with luxury,and its waterfront estates are a testament to this.These opulenthomes for saleoften feature custom designs,private docks,infinity pools,and expansive grounds.They represent the pinnacle of Florida living,offering breathtaking views and unparalleled privacy on the Butler Chain.

Spacious Single-Family Homes

Beyond the grand estates,a significant portion ofhomes for sale in Windermereconsists of spacious single-family residences.These properties often reside in master-planned communities,providing excellent amenities like community pools,tennis courts,and walking trails,perfect for families and those seeking ample living space.

Modern Townhomes & Villas

For those desiring a low-maintenance lifestyle without compromising on location or quality,Windermere also offers a selection of modern townhomes and villas.Thesehomes for saleare increasingly popular,providing contemporary designs,often within gated communities,and proximity to local conveniences and downtown Windermere.

Popular Windermere Neighborhoods & Communities

Understanding the distinct character of Windermere's neighborhoods is crucial when exploringhomes for sale.Each community offers a unique blend of amenities,architectural styles,and lifestyle options.

Isleworth:Premier Golf & Lakefront Living

Isleworth stands as one of Florida's most exclusive golf and country club communities.Thehomes for salehere are magnificent custom estates,many with direct lake frontage or golf course views.It's a sanctuary of luxury,privacy,and world-class amenities,appealing to high-net-worth individuals.

Keene's Pointe:Gated Community Excellence

Another prestigious gated community,Keene's Pointe offers an exquisite collection of customhomes for salesurrounding the Golden Bear Club golf course.Residents enjoy private access to the Butler Chain of Lakes,tennis courts,and a community pool,embodying an upscale,active lifestyle.

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Summerport & Lakeside at Windermere:Family-Centric Options

For families seeking vibrant communities with robust amenities,Summerport and Lakeside at Windermere offer compellinghomes for sale.These neighborhoods are known for their strong community spirit,excellent schools,and amenities such as pools,playgrounds,and recreational facilities,providing an ideal environment for raising children.

The Reserve at Windermere & Butler Bay:Exclusive Enclaves

The Reserve at Windermere and Butler Bay represent smaller,yet equally exclusive,enclaves offering custom-builthomes for sale.These communities are cherished for their tranquility,spacious lots,and often,direct access or stunning views of the Butler Chain,providing a more intimate luxury living experience.

Navigating the Windermere, FL Real Estate Market with The Nest Group

The Windermere real estate market is dynamic and competitive,especially for premiumhomes for sale.Partnering with a local expert is essential to successfully navigate its complexities and secure your dream property.

Understanding Market Trends

The Nest Group provides invaluable insights into current market trends forhomes for sale in Windermere, FL.Our deep understanding of property values,demand,and growth areas ensures you make informed decisions,whether buying a primary residence or an investment property.

Finding Your Ideal Property

With an extensive network and access to exclusive listings,The Nest Group is uniquely positioned to help you discoverhomes for sale in Windermerethat perfectly match your criteria.From secluded lakefront retreats to bustling family homes within top-tier school zones,we are dedicated to finding your ideal home in this coveted Central Florida paradise.

Newest Homes for Sale in Windermere, FL

$1,750,000
4 Beds 3 Baths Butler Bay SubDv. 34786 Zip Code
Set behind the gates of Windermere Club, this lakefront residence delivers everyday comfort with a resort-style backdrop on beautiful Lake Crescent. Offering 4 bedrooms and 3 baths, the home is designed for easy living and effortless entertaining, with bright, open gathering spaces that keep the water views front and center. At the heart of the home, the kitchen pairs generous prep space with a welcoming bar and an adjacent dining area that comfortably seats six, while a separate formal dining room adds flexibility for holidays and special occasions. The main living area is wrapped in expansive windows, filling the home with natural light and framing tranquil lake scenery throughout the day. Step outside to a covered lanai and screened pool area ideal for quiet mornings, sunset dinners, and everything in between. Take a dip in the saltwater pool, now enhanced with a new pool heater and an Aqua Link pool & spa control system for simple, modern management. The primary suite is a private retreat with captivating lake views and a spa-like bath featuring large windows overlooking a secluded courtyard. Three additional bedrooms provide plenty of space for family, guests, or a home office setup. For true lakefront living, enjoy the newer dock with a covered boat lift, perfect for skiing, cruising, kayaking, or paddle boarding whenever the mood strikes. Upgrades and highlights include double pane windows and sliding glass doors, Shark Coating garage floors, a water purifier, Paradise Grill outdoor kitchen with cover and TV, new pool heater, two brand new AC units, a new water heater, plus additional notable improvements throughout. This is the Windermere waterfront lifestyle, refined, relaxed, and ready to enjoy. Be sure to click on the virtual tour links.

2503 Butler Bay Drive N, Windermere

$2,195,000
4 Beds 4 Baths Kelso On Lake Butler SubDv. 34786 Zip Code
Opportunities like this in Windermere rarely reach the open market and are often treasured for generations.Welcome to an extraordinary lakefront estate in the highly coveted community of Kelso on Lake Butler, where timeless architecture, unmatched privacy and the ultimate Florida lifestyle come together on over 2 pristine acres along the shores of private Lake Davis. This sprawling custom one-story estate offers almost 4000 square feet of thoughtfully designed living space with breathtaking sunset views, a private sandy shoreline,private boat ramp and covered boat dock on Lake Davis. Residents of Kelso on Lake Butler also enjoy exclusive access to a private community boat ramp, fishing pier and park on the world-renowned Butler Chain of Lakes,connecting you to 13 interconnected ski lakes and more than 5,000 acres of recreational paradise just moments from your front door. From the moment you arrive, the heavily landscaped grounds,massive brick paver driveway,lush tropical landscaping & mature oak trees create a commanding first impression.Oversized double entry doors open to soaring 14-foot ceilings and an incredible open-concept living space designed for both grand entertaining and everyday comfort.The impressive great room (34x25) is anchored by a dramatic wall of custom built-ins, stunning stonework and an electric fireplace that creates an incredible focal point. The chef’s kitchen is equally spectacular,featuring an oversized gathering island,separate Sub-Zero refrigerator and freezer,custom cabinetry and a showstopping Wolf freestanding range,vented hood and pot filler.This space was designed to bring people together and will quickly become the centerpiece of every gathering. The owner’s retreat is a true private sanctuary , massive custom walk-in closet with additional full sized W & D, massive spa and secluded outdoor shower. On the opposite side of the home, a bonus/flex room leads to an additional ensuite bedroom and two oversized secondary bedrooms connected by a Jack and Jill bath provide exceptional privacy and flexibility for family and guests. A secondary garage exit also allows this area to easily be converted into an in law suite. One of the home’s most captivating features is the massive pocketing glass wall that completely opens the interior to the enormous covered & screened lanai, creating a seamless indoor-outdoor living experience. Tongue & groove ceilings,a summer kitchen and panoramic lake views transform this space into the ultimate entertaining destination.Every evening feels special as you enjoy postcard-worthy sunsets over Lake Davis from the comfort of your own backyard. Additional highlights include a climate-controlled garage,irrigation sourced directly from the lake for reduced waterbill &a durable metal roof designed for decades of drama free ownership. Kelso on Lake Butler is one of Windermere’s most sought-after luxury lakefront communities,known for its canopy oak-lined streets,estate homes and unmatched access to the Butler Chain of Lakes.Tucked away in one of Windermere’s best-kept secrets,yet only minutes from top-rated schools, dining, shopping and major attractions,this location perfectly balances tranquility and convenience. This is more than a home,it is a rare legacy property and a true unicorn opportunity in the Windermere luxury real estate market. Opportunities like this are few and far between.Do not miss your chance to own one of Central Florida’s most special lakefront estates.

5624 W Lake Butler Road, Windermere

$2,099,995
5 Beds 5 Baths Estancia/Windermere SubDv. 34786 Zip Code
A Masterpiece of Luxury Living in Windermere Welcome to an extraordinary custom estate in the prestigious gated community of Estancia at Windermere, where timeless elegance meets modern luxury. Enhanced with over $400,000 in post-construction upgrades, this exceptional 2019 residence is a true showpiece. Offering more than 4,230 square feet of beautifully designed living space, the home features 5 bedrooms, 5 bathrooms, soaring ceilings, designer lighting, expansive walls of glass, and premium finishes throughout. Every detail has been thoughtfully curated to create an atmosphere that is both sophisticated and inviting. At the heart of the home is a spectacular chef's kitchen equipped with Sub-Zero and Wolf appliances, custom cabinetry, an oversized island, wine refrigerator, and seamless flow into the spacious living and dining areas—perfect for everyday living and effortless entertaining. The luxurious first-floor owner's suite serves as a private retreat, complete with a spa-inspired bath and oversized custom walk-in closet. Additional highlights include a private executive office, formal dining room, upstairs loft, media/flex room, oversized laundry room, and abundant storage. Step outside to your own private resort. The professionally designed backyard features a heated saltwater pool, elegant Travertine deck, covered lanai, fully equipped summer kitchen, lush tropical landscaping, and a fully fenced yard—creating the perfect setting for relaxing weekends or unforgettable gatherings. Luxury is matched by intelligent design with a $70,000 whole-home solar energy system and automatic backup generator, providing exceptional efficiency, long-term savings, and uninterrupted comfort during Florida's storm season. Completing the property are a three-car garage, concrete tile roof, impeccable landscaping, and striking curb appeal. Located within the Town of Windermere, residents enjoy exclusive amenities including private tennis courts, boating access to the Butler Chain of Lakes, parks, playgrounds, dog parks, walking trails, and year-round community events. Just minutes away are championship golf courses, premier private schools, upscale shopping, fine dining, major highways, and Orlando's world-famous attractions. Estancia at Windermere is one of Central Florida's most desirable luxury communities, known for its estate-sized homesites, beautifully maintained surroundings, and private atmosphere. This is more than a home—it's an exceptional lifestyle. Luxury residences of this caliber rarely become available. Experience one of Windermere's finest addresses and discover a home where every detail has been elevated beyond expectation.

1118 Estancia Woods Loop, Windermere

$30,000,000
7 Beds 14 Baths N/A SubDv. 34786 Zip Code
Showcasing Central Florida’s most iconic lakefront estate: an 18-acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Ridge Estate is comprised of multiple buildings spanning 51,000 square feet of space including an expansive 20,333 square-foot Georgian-style Plantation mansion that is a showplace residence with generous luxurious spaces, classic elegance, and the ultimate in security and serenity. The walled entry opens to a grand foyer with a floating mahogany staircase, marble floors, paneled walls, and Murano chandeliers. An art gallery leads to a spacious living room featuring rich mahogany millwork and expansive lake vistas. Gourmet kitchen: salamander, dual double convection ovens, commercial icemaker, full-size refrigerator, and freezer. The main level includes one of two owners' suites, plus a library-lounge or a possible sixth bedroom. Dual staircases or a Thyssenkrupp elevator provide access to the upper level, which features four-bedroom suites, including the primary retreat. An 85-foot parlor with 20-foot ceilings, built-in bookshelves, and a wet bar provide a dramatic entertaining space. Screened porch captures southern lake views and Disney fireworks. Breezeway connects to a 5,600 SF rustic lodge with a bar, catering kitchen, entertainment hall, and locker facilities. Outdoor amenities: Junior Olympic pool, spa, decorative fountain, architectural lighting, direct lake access. The vast and open water location offers an ideal space for seaplane arrivals and departures. Additional structures include a 4,000 SF paneled garage with 20-foot ceilings, an office, and a guest apartment; a 3,800 SF storage building; three separate garages accommodating motor coach and car collection; and staff quarters with a private courtyard. A rare fusion of Southern grandeur, lakefront serenity, and equestrian potential—without any interference of an HOA. Truly a legacy compound crafted for those who demand the extraordinary.

9508 Windy Ridge Road, Windermere

$640,000
4 Beds 4 Baths Eden Isle SubDv. 34786 Zip Code
Welcome to 13936 Eden Isle Blvd, where comfort, space, and modern updates come together in one of Windermere’s desirable and sought after gated communities - Eden Isle. Step into a fresh chapter of elevated living with this beautifully updated 4-bedroom, bonus room, 3.5-bathroom residence offering approximately 2,675 square feet of thoughtfully designed living space. The open and functional floor plan creates the perfect balance for both everyday living and effortless entertaining. The first floor features a seamless flow between the kitchen, dining, and living areas, all enhanced by a blend of vinyl and tile flooring. The sleek kitchen showcases stainless-steel appliances, generous counter space, and brand-new cabinetry with elegant granite countertops, creating a stylish and functional centerpiece of the home. Upstairs, three well-proportioned bedrooms, including a secondary suite, offer comfort, privacy, and a versatile layout ideal for family or guests. The upper level provides a bright and functional living arrangement designed for everyday convenience. The spacious primary suite is located on the main level and features dual vanities, a separate shower, and generous closet space, creating a relaxing private retreat. A versatile bonus room located near the entry adds exceptional flexibility—ideal as a home office, media room, playroom, or additional lounge space. A first-floor laundry room adds everyday convenience, while the attached two-car garage and extended driveway provide ample parking. Recent upgrades include a new roof (2021), downstairs A/C unit replacement (2021), new water heater (2024), new exterior paint (April – May 2026), new carpet fully replaced upstairs and in the downstairs primary suite creating a fresh and cohesive interior feel (April – May 2026), and full kitchen and bathroom cabinetry upgrades with granite countertops (April – May 2026), delivering both style and long-term peace of mind. Outdoor living is just as inviting, with front and back porches perfect for morning coffee or evening relaxation, all set within a well-maintained community environment. Perfectly positioned in Windermere, known for its A-rated schools. The residents from Eden Isle Community enjoy gated security, a private boat dock with canal access to Lake Speer, and a prime location just outside the Summerport shopping plaza and Publix. You’re also minutes from Winter Garden Village, top-rated schools, grocery stores, dining, and major conveniences. This move-in-ready Windermere home delivers the ideal combination of location, upgrades, and lifestyle—an opportunity not to be missed. Schedule your showing today.

13936 Eden Isle Boulevard, Windermere

$12,350,000
7 Beds 10 Baths Isleworth 5th Amd SubDv. 34786 Zip Code
Set along beautiful Lake Blanche within the gates of Isleworth, this extraordinary modern estate is a grand haven of remarkable scale and design. Spanning more than 11,000 square feet, the residence is thoughtfully positioned to capture sweeping views across the lakefront, with walls of glass framing the water from nearly every room and filling the interiors with natural light. Beauty and modernity define the home, where sleek architectural lines are complemented by elegant oak wood flooring throughout. The main living areas flow effortlessly, creating both an impressive setting for entertaining and a comfortable environment for everyday living. At the heart of the home, a striking kitchen features distinctive Viking appliances, a Miele espresso machine, two wine refrigerators, and a seamless connection to the family room, patio, and surrounding living and dining spaces.The estate offers 7 spacious bedrooms and 9.5 baths, with each suite designed for privacy and comfort. Multiple levels—including a rooftop terrace—provide an array of vantage points from which to enjoy the lake and surrounding grounds. Additional highlights of the estate include a private home theater; a versatile lakefront bonus room ideal for a game room, wellness studio, or creative space; and two adjoining offices with custom built-ins that can be closed off for quiet focus. A standout feature of the property is the expansive guest residence on the lower level, complete with its own full kitchen, living room, two en-suite bedrooms, laundry room, and private patio—perfect for extended family or long-term guests. Practicality meets luxury with three laundry rooms throughout the estate, an elevator servicing multiple levels, and a four-bay garage. Outdoors, the expansive grounds offer both privacy and possibility, anchored by a spacious yard that leads to a private dock along the shores of Lake Blanche. A covered lanai with summer kitchen and screened living area creates an inviting setting for year-round entertaining, seamlessly blending indoor and outdoor living. This is a home that delivers on every level—scale, setting, and sophistication—offering a truly exceptional lakefront lifestyle within one of the finest golf club communities in the world.

9312 Blanche Cove Dr, Windermere

$535,000
3 Beds 3 Baths Windermere Lndgs Ph 02 SubDv. 34786 Zip Code
RARE OPPORTUNITY IN WINDERMERE LANDINGS! Beautifully upgraded 4-bedroom home in one of Windermere's most desirable communities, just steps from Windermere Preparatory School. Originally designed with an expansive downstairs living and family room layout, the spacious loft was thoughtfully converted into a versatile fourth bedroom, creating exceptional value rarely found at this price point. The result is a flexible floor plan ideal for families, remote work, guests, or a growing household. Pride of ownership shines throughout this one-owner home. Elegant porcelain tile flooring, custom wood accent walls, designer finishes, and abundant natural light create a sophisticated yet welcoming atmosphere. Every detail has been carefully maintained and thoughtfully enhanced. The location is simply unmatched. Enjoy a short walk to the community pool and playground, while being just minutes from top-rated schools, shopping, dining, and everyday conveniences. Disney, major attractions, and Orlando's world-class entertainment are only a short drive away. Whether you're searching for a primary residence, a relocation home, or an investment in one of Central Florida's most sought-after areas, this property delivers the perfect combination of location, upgrades, functionality, and value. Homes offering this level of quality, flexibility, and proximity to Windermere Prep rarely become available. Schedule your private showing today.

6412 Golden Dewdrop Trail, Windermere

$320,000
3 Beds 2 Baths Lakeside/Lks/Windermere SubDv. 34786 Zip Code
investment property with a very high rental demand for its location and comfort or a vacation retreat, this condo is perfect for you. Beautiful condo located in Lakeside at Lakes of Windermere, corner unit on the first floor (ground floor) with covered lanai Welcome to this stunning condo located in one of the best and most exclusive areas of Orlando Fl such as Windermere, with 3 bedrooms and 2 bathrooms, this condo which is in perfect condition of care and maintenance, offers a spacious and open layout that perfectly combines the kitchen, dining and living areas, ideal for both everyday life and entertaining. The master suite, located to one side for privacy, has a generous bathroom with a garden-style tub/shower and a large walk-in closet. The kitchen is beautifully equipped with wood cabinets. On the opposite side, you will find the secondary bedrooms along with the second bathroom, a convenient laundry closet and ample storage space throughout. The gated resort-style community includes a clubhouse, pool, fitness room, walkways, green areas, parks, sports areas, on-site management and valet trash service, ensuring convenience and comfort. Located in the heart of Windermere in a strategic location just minutes from Walt Disney World and Downtown Winter Garden, easy access to major streets and highways that bring you closer to other important areas of the city and other local attractions such as Universal Studios, it is close to Publix, shops, restaurants and stores.

11434 Jasper Kay Terrace Unit 106, Windermere

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