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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.

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Windermere, FL Communities

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

7663 Bramwell Street, Windermere
$369,990
3 Beds ⋅ 3 Baths ⋅ Wickham Park 04 05 06 09 10 11 12 01 SubDv. ⋅ 34786 Zip Code
Welcome to 7663 Bramwell Street, a well-kept 3-bedroom townhome in Windermere’s Wickham Park community, offering low-maintenance living in one of West Orange County’s most in-demand areas. With 1,510 sq ft, the home features an open main level where the living, dining, and kitchen areas flow together, ideal for everyday living and entertaining. The kitchen offers an open layout , a French door fridge and spacious bar and island. Upstairs, sits the primary suite, joined by two additional bedrooms with generous closet space and a full bath. Additional highlights include a 5 year old roof and ac, an inside laundry area, and an detached 2 -car garage. The HOA covers [exterior maintenance/lawn care/community pool], so you can spend more time enjoying Central Florida. Conveniently located near Winter Garden–Vineland Road, you’re minutes from shopping, dining, and major roadways, with easy access to the theme parks and the Horizon West area. Whether you’re a first-time buyer, downsizing, or adding to your investment portfolio, this townhome is a must-see. Schedule your showing today!

7663 Bramwell Street, Windermere
13731 Calera Alley, Windermere
$465,000
3 Beds ⋅ 3 Baths ⋅ Vineyards/Horizons West Ph 2b SubDv. ⋅ 34786 Zip Code
Welcome home to this highly upgraded, move-in ready outside end unit in the Vineyards of Horizons West. This unit features a fenced side yard with patio, walkway to garage, front porch and landscaping, pond and open views. The front of the unit has a quiet courtyard setting. Inside you will find a beautiful large gourmet kitchen w/upgraded cabinets and sink, including a large kitchen island. A very large open great room and dining area. The first floor is wood look "porcelain tile" with sealed grout for minimal upkeep. Downstairs also features a spacious half bath and a large storage area under the stairs and separate laundry area. The garage is oversized with a finished floor. Upstairs are three bedrooms and a loft. Bath in the primary has been upgraded to frameless glass, a large spacious closet with extra racks added. $48K in upgrades from the builder when new. Pond and open space views from the first and second floor make the setting of this unit even more appealing. A quiet community with a park-like atmosphere, community pool and playground, and walking distance to Windermere High School.

13731 Calera Alley, Windermere
5021 Carillon Lane, Windermere
$625,000
4 Beds ⋅ 3 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code
Welcome to this beautiful home in a highly desirable community known for its top-rated schools and beautifully maintained surroundings. Lush landscaping, graceful palm trees, and a covered front porch create a warm welcome. Inside, the foyer opens to a formal dining room with an elegant chandelier and a home office enclosed by glass French doors. Neutral tones, arched walkways, and wood laminate flooring are found throughout the main living areas. The spacious, open floor plan flows into the kitchen featuring shaker cabinets, granite countertops, a decorative backsplash, stainless steel appliances, a wine rack, and a large custom pantry with built-in storage. A dedicated laundry area with folding space adds convenience. The light-filled living room opens to a breakfast nook with a stylish rattan light fixture, bay window seating, and sliding glass doors leading to the pool. The private primary suite features double-door entry, a custom walk-in closet with extensive built-ins, and a spa-inspired bathroom with dual vanities, a large soaking tub, and a separate glass-enclosed shower. Three additional bedrooms and two full guest bathrooms with tub/shower combinations provide plenty of space for family and guests. Step outside to your own tropical retreat, complete with a screened-in pool, shaded gazebo, and vinyl fencing for added privacy. Updates include HWT 2023, HVAC 2019, and roof replacement in 2020. Conveniently located near entertainment, shopping and dining at Winter Garden Village, Walt Disney World, and major roadways including Florida's Turnpike, this home offers both comfort and accessibility. Schedule your private showing today!

5021 Carillon Lane, Windermere
5231 Lemon Twist Lane, Windermere
$559,900
4 Beds ⋅ 4 Baths ⋅ Summerport Ph 03 SubDv. ⋅ 34786 Zip Code
?? REMODELED HOME IN WINDERMERE! HIGHLY MOTIVATED SELLER! ?? 5231 Lemon Twist Ln, Windermere ??? 4 Bedrooms | ?? 2.5 Bathrooms Discover a spacious home that combines comfort and style. Featuring a remodeled kitchen, updated bathrooms, and carpet-free flooring throughout, this home is ready for you to make it your own. All appliances are included! Generous living spaces plenty of room to relax, entertain, and create lasting memories. Don’t miss this opportunity to call Windermere home! The seller is highly motivated and welcomes! ?? Contact me to schedule your showing and submit!

5231 Lemon Twist Lane, Windermere
8582 Powder Ridge Trail, Windermere
$630,000
4 Beds ⋅ 4 Baths ⋅ Windermere Trls Ph 3b SubDv. ⋅ 34786 Zip Code
Virtually Staged. EXCELLENT OPPORTUNITY TO LIVE OR INVEST! This impressive Kipling model with lake views offers an exceptional combination of comfort, upgrades, and flexibility. The property features fully paid-off solar panels, a whole-house water filtration system, and electrical connections in the parking area with the option to install EV chargers. The main home has been thoughtfully updated. All bathrooms have been renovated, including 3 smart toilets with heated seats. The flooring throughout the main home has been replaced with high-quality waterproof luxury vinyl, providing a modern, seamless look that is both stylish and easy to maintain. The primary bedroom features a private balcony, offering an inviting additional space to relax and unwind. The kitchen features stainless steel KitchenAid appliances, granite countertops, backsplash, and LED-lit cabinetry. The spacious loft above the garage provides even more versatility and additional living space. The main home is currently VACANT and easy to show. Only the attached in-law suite is currently rented on a month-to-month basis, and the property can be delivered completely vacant at closing, ready for its new owners to move in. One of the property's greatest advantages is the in-law suite with a private entrance, making it ideal for extended family, guests, or as an opportunity to generate additional rental income. The parking area also offers the option to add a separate washer and dryer for the future occupant or guest of the in-law suite. This flexibility makes the property an excellent option for first-time homebuyers, families looking for additional space, or investors seeking additional income potential. Outside, the property features fencing and paver walkways, creating welcoming spaces to enjoy the outdoors. Strategically located just minutes from Disney, restaurants, shopping, and Central Florida's major attractions, this property combines location, upgrades, and multiple possibilities under one roof. Ready for its next owner!

8582 Powder Ridge Trail, Windermere
8631 Greenbank Boulevard, Windermere
$669,000
4 Beds ⋅ 4 Baths ⋅ Lakes/Windermere-Peachtree SubDv. ⋅ 34786 Zip Code
Very nice two story executive home in the gated community of Lakes of Windermere. Location provides easy access to Disney employees parking, shopping in Windermere. The community is very well maintained and provides a community pool, playground and more.

8631 Greenbank Boulevard, Windermere
Quail Cove Court, Windermere
$995,000
34786 Zip Code
Introducing 1.44 private acres on Quail Cove Court, a rare opportunity to build your custom Windermere estate. Located in the Windermere Downs neighborhood but not subject to the HOA, this homesite is set at the end of a quiet street and framed by mature trees. There are no deed or build restrictions, so you can choose your builder and design a home that is entirely your own. Natural gas is available on site, and the property is served by septic. The Town of Windermere, the Butler Chain of Lakes, top golf, and fine dining are all just minutes away. Bring your vision and build the home you’ve imagined.

Quail Cove Court, Windermere
8516 Danforth Drive, Windermere
$350,000
2 Beds ⋅ 3 Baths ⋅ Lakes/Windermere - Lake Reams Townhomes SubDv. ⋅ 34786 Zip Code
Live Where the Magic Happens! This beautifully maintained, FULLY FURNISHED 2-bedroom, 2.5-bath Townhome is located in the coveted Windermere area, perfectly situated just minutes from DISNEY’S BACKYARD!! A quiet placement towards the rear of the community, this unit provides peaceful views of the conservation and walking trail surrounded by majestic oak-lined streets that capture the charm and serenity of this sought-after community. Step inside to an inviting open-concept layout with tile flooring throughout the main level and a seamless flow between the Living, Dining and Kitchen areas, perfect for everyday living or entertaining. Stunningly renovated Kitchen features Granite countertops, Stainless Steel Appliances, Island, Stone Backsplash and Dinette space. Upstairs, all bedrooms provide comfort and privacy with newer carpet. The Primary Bedroom boasts a walk-in closet and ensuite Bathroom with garden tub/shower combo. The second Bedroom also features an ensuite bathroom. Relax outdoors in your private, fenced courtyard with artificial turf, the perfect spot for morning coffee or evening gatherings, leading to your detached 2-car rear entry garage. Have complete peace of mind with the big-ticket expenses that have been recently taken care of: Roof 2021, Hot Water Heater 2021, AC 2021 and new Plumbing shut off valves and main water pressure reducer valve 2024. Low HOA includes a sparkling Community Pool and walking trails throughout! Zoned for top-rated Schools and conveniently close to major Theme Parks, and fantastic Shopping and Dining in Lakeside Village and Winter Garden Village. Experience the best of Florida living: Quiet Nature, Disney Magic and Windermere Charm - all in one!

8516 Danforth Drive, Windermere
14500 Bridgewater Crossings Boulevard, Windermere
$400,000
4 Beds ⋅ 3 Baths ⋅ Tennyson Pk/Summerport SubDv. ⋅ 34786 Zip Code
Morning coffee at Foxtail, an evening walk for Kelly’s Homemade Ice Cream, and a move-in-ready home waiting when you get back. At 14500 Bridgewater Crossings Boulevard, that can be your everyday routine. Located in Windermere’s Summerport community, this 4-bedroom, 2.5-bath townhome combines a convenient neighborhood setting with fresh interior paint throughout, new luxury vinyl plank flooring upstairs, and no carpet anywhere in the home. A main-floor primary suite is a standout feature, offering the convenience of having your bedroom and private bathroom downstairs, with three additional bedrooms, a full bathroom, and a loft upstairs. Whether you need room for guests, a dedicated home office, or a second gathering space, the layout gives you options. Downstairs, the living and dining areas, kitchen, and guest half bath keep everyday activities on the main level. A courtyard provides an outdoor spot for plants, coffee outside, or unwinding at the end of the day, while a covered walkway connects the home to the two-car garage. And the neighborhood gives you plenty of reasons to step outside. Walk across the street for your favorite coffee or a scoop of ice cream, enjoy nearby Summerport Park, and appreciate the convenience of having Keene’s Crossing Elementary close by. Summerport’s community pool, clubhouse, fitness center, tennis courts, playgrounds, and walking paths make it easy to fit recreation into your routine without planning an entire day around it. Beyond the neighborhood, Publix at Cornerstone at Summerport keeps grocery runs convenient, while Winter Garden Village and Hamlin offer nearby shopping, restaurants, and entertainment. Walt Disney World is also within easy reach, whether your plans call for a full park day or a spontaneous evening out. With fresh updates already completed, a main-floor primary suite, and neighborhood favorites just a walk away, this home is ready for you to settle in and start enjoying everything beyond the front door. Schedule your private showing today.

14500 Bridgewater Crossings Boulevard, Windermere
9621 Windy Ridge Road, Windermere
$8,999,999
9 Beds ⋅ 16 Baths ⋅ Windsor Hill SubDv. ⋅ 34786 Zip Code
Under Construction. Seller is selling as is buyer to take over and find new builder

9621 Windy Ridge Road, Windermere
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
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