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

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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

$459,000
3 Beds ⋅ 3 Baths ⋅ Lake Burden South Ph I SubDv. ⋅ 34786 Zip Code
Virtually Staged. This former model corner unit townhome (3 bed, 2.5 bath) offers maintenance free living in one of Windermere's most sought-after neighborhoods. It features an open floor plan, a bright corner kitchen with granite countertops, a spacious paved backyard, ample storage and a rear large attached 2 car garage. Enjoy nature views from the large front porch. Located in a highly desirable Windermere location known for its beautiful tree lined streets and tranquil setting. Residents enjoy resort style amenities, proximity to two stunning lakes with a dockside, and an active lifestyle.

7327 Millstone Street, Windermere
$1,029,990
4 Beds ⋅ 4 Baths ⋅ Palms At Windermere SubDv. ⋅ 34786 Zip Code
Virtually Staged. Arlington Floorplan – 3,140 Sq. Ft. | 4 Beds | 4Baths | 2.5-Car Garage | Move-In ReadyWelcome to the Arlington with Bonus – a thoughtfully designed, 2-story home that perfectly blends luxury, functionality, and comfort. This brand new 3,140 square foot residence sits on an wooded lot, offering expansive indoor and outdoor living space, ready for immediate move-in.Key Features:4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with spa-like en-suite bathroom and large walk-in closet.4 Full Bathrooms: Modern finishes with quartz countertops, tile flooring, and upgraded fixtures throughout.Gourmet Kitchen: A chef’s dream featuring built-in stainless steel appliances, large center island, upgraded cabinetry, quartz countertops, walk-in pantry, and designer lighting – perfect for hosting or everyday meals.Open-Concept Living: The heart of the home flows seamlessly from the kitchen to the dining area and large family room, all overlooking the covered lanai for indoor-outdoor living.2.5-Car Garage: Ample space for two vehicles plus additional storage or hobby area.Oversized Lot: Extra space for a garden,—ideal for entertaining or relaxing outdoors.Move-In Ready: No waiting required.

14371 Crest Palm Avenue, Windermere
$415,000
2 Beds ⋅ 3 Baths ⋅ Lakes/Windermere-Lk Reams Twhm SubDv. ⋅ 34786 Zip Code
Discover this spotless corner-unit townhome in Windermere Lakes, offering some privacy with a serene conservation area behind the home and no neighbors on one side. The open-concept layout seamlessly connects the kitchen to the living area, creating an inviting space for everyday living and entertaining. The kitchen features stainless steel appliances, 42” cabinets, added custom cabinetry, and tile flooring throughout the main areas. An extra half bath downstairs adds convenience for guests. Upstairs, the master bedroom and shower are sure to impress. Enjoy beautiful tree-lined streets, mature landscaping, and a detached two-car garage with a charming, paved courtyard perfect for grilling and relaxing outdoors. The community offers a pool and clubhouse, ideal for soaking up the Florida sunshine. The low HOA includes exterior maintenance, roof maintenance, landscaping, and access to community amenities. Located just minutes from Disney World and all the Disney parks, with shopping, dining, major highways, and top attractions close by, as well as minutes from the Tibet Butler Preserve, where you can enjoy the natural beauty of Florida. Make your appointment today to view this beautiful home.

12405 Cruxbury Drive, Windermere
$749,995
3 Beds ⋅ 2 Baths ⋅ Silver Woods Ph 01 SubDv. ⋅ 34786 Zip Code
Nestled in the charming and highly desirable Silverwoods subdivision of Windermere, this beautifully maintained home offers the perfect blend of comfort, convenience, and community living. Ideally situated between Bay Hill and Isleworth, Silverwoods is a sought-after neighborhood of just over 250 homes, known for its tree-lined streets, sidewalks, street lighting, and welcoming atmosphere. Residents enjoy access to tennis courts and the ease of walkable surroundings, all while being just minutes from shopping, dining, grocery stores, churches, and everyday conveniences. This inviting residence features three bedrooms and two bathrooms in a thoughtfully designed layout, enhanced by an impressive 650-square-foot addition that includes a spacious sunroom, bar area, and den—creating versatile living spaces ideal for both everyday comfort and entertaining. Originally built in 1985, the home has been extensively updated with a remodeled kitchen featuring new cabinetry, a standalone island, and updated appliances, all complemented by wood and tile flooring throughout. Additional upgrades include high-efficiency windows, a new 4-ton HVAC system with Nest thermostat, new ductwork and attic insulation, and a new 50-gallon water heater—offering both comfort and energy efficiency. Interior improvements such as new doors, refinished ceilings with LED recessed lighting, and a beautifully refinished stone fireplace add to the home’s modern appeal. The expansive Florida room provides a bright and relaxing retreat with year-round enjoyment of the backyard, while exterior enhancements include premium architectural shingles, a new septic field, a 7-zone irrigation system, and a water softener system. Fiber optic internet is also available, supporting today’s connected lifestyle. This is more than a home—it is an opportunity to experience elevated living in one of Windermere’s most desirable and conveniently located communities.

9237 Sabal Palm Circle, Windermere
$760,000
5 Beds ⋅ 5 Baths ⋅ Stillwater Xings Prcl Sc-13 Ph SubDv. ⋅ 34786 Zip Code
Check out 4309 Saltmarsh Sparrow Dr, a residence featuring a partial flooring replacement that enhances its overall presentation. The kitchen is equipped with all stainless steel appliances and includes a functional island. The primary bedroom provides a walk in closet, while the primary bathroom contains double sinks and a separate tub and shower. An exterior covered patio extends to a fully fenced in backyard, creating defined outdoor space. This property includes updated finishes and functional living spaces. Included 100-Day Home Warranty with buyer activation

4309 Saltmarsh Sparrow Drive, Windermere
$600,000
4 Beds ⋅ 3 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code
**BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE BUY DOWN for qualified buyers on new loan locks completed on or before 6/30/26!!** Don't miss out on this 4 bedroom 3 bathrooms in the tranquil Summerport community in Windermere. The first floor consists of the Kitchen, dining, family room, living room, the Master bedroom and the 3 other bedrooms and the guest bathroom. The second floor consists of the large loft, closets and a full bathroom. Don’t miss your chance to experience exceptional living very close to Keenes Crossing Elementary, Bridgewater Middle and Windermere high

14217 Bridgewater Crossings Boulevard, Windermere
$1,775,000
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
SIGNIFICANT PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to a truly exceptional custom home in Keene's Pointe, one of Windermere’s most sought-after guard-gated communities. Built by W. J. Sauerwine and set on a beautifully landscaped .43-acre homesite with mature oak trees, this residence offers a rare combination of privacy, thoughtful design, and extensive modern upgrades. This 4-bedroom plus office, 4-bath home features a highly functional, split floorplan layout with nearly all living space on the main floor, including the primary suite and main living areas, with one bedroom and full bath upstairs. The home has been extensively updated throughout, beginning with all new interior paint and continuing into a fully renovated kitchen with updated finishes and appliances. All four bathrooms have been completely reimagined from floor to ceiling with today’s luxury buyer in mind, creating a cohesive and elevated feel throughout the home. Attention to detail is evident in every space, from the custom built-ins in the office and family room to the all-new lighting and chandeliers installed throughout both the interior and exterior, all integrated with a Lutron system for seamless control. Sonos in-ceiling speakers have been installed throughout the home, creating a whole-home audio experience. What truly sets this home apart is its advanced energy efficiency and independence. Equipped with a Tesla solar system, multiple Powerwalls and electricity backup, the home is designed to operate seamlessly even during outages while significantly reducing long-term energy costs. With the ability to sell excess power back to the grid and the convenience of EV charging at the ready, this is a rare blend of luxury and forward-thinking functionality. The primary suite offers a private retreat with French doors leading to the lanai, ample space for a sitting area, and a spa-inspired bath with dual vanities, soaking tub, walk-in shower, and generous closet space. Secondary bedrooms are well-positioned with direct bath access, providing both comfort and functionality. Outdoor living is equally impressive, featuring a screened pool and an expansive covered lanai designed for both relaxation and entertaining. The rear patio is equipped with an outdoor refrigerator, sink, and TV, creating the perfect setting for year-round enjoyment. The home is also equipped with a Ring security camera system covering the exterior. Ideally located directly across from The Golden Bear Club members' driving range from the front, with golf course views to the rear, this home also provides access to Keene’s Pointe amenities, such as parks and playgrounds, including community boat ramp to Lake Burden, and access to the Butler Chain of Lakes for recreation. Membership at The Golden Bear Club further allows for access to the Jack Nicklaus-designed golf course, tennis courts, fitness center, and restaurant. Residents of Keene's Pointe enjoy a lifestyle that blends privacy, recreation, and convenience, all just minutes from the world's best theme parks and entertainment, Winter Garden Village, Restaurant Row, and top-rated schools. This is a rare opportunity to own a fully updated, energy-efficient custom home in Keene’s Pointe that truly stands apart from the rest. Furniture custom-designed specifically for the home is negotiable, offering a potential turnkey opportunity for the next owner.

6110 Keenes Pointe Drive, Windermere
$460,000
3 Beds ⋅ 3 Baths ⋅ Carrington SubDv. ⋅ 34786 Zip Code
The house does not include furniture. Welcome to this beautifully maintained 3-bedroom, 3-bathroom townhouse, with furniture available for negotiation, located in the desirable Carrington at Windermere community. This residence provides a well-designed open-concept floor plan that seamlessly blends comfort and functionality, ideal for both everyday living and entertaining. The home features spacious bedrooms, full bathrooms thoughtfully distributed for convenience, and a bright living area enhanced by natural light. The kitchen is equipped with modern finishes, ample cabinetry, and a layout that connects effortlessly to the dining and living spaces, creating a warm and inviting atmosphere. Residents of Carrington enjoy a peaceful and well-maintained environment, with amenities that may include a community pool, walking areas, and beautifully landscaped surroundings that enhance the overall lifestyle experience. Ideally situated in the heart of Windermere, the property provides quick access to everyday conveniences and top destinations such as Lakeside Village Center, The Grove at Windermere, and Walt Disney World Resort. Enjoy proximity to shopping, dining, major roadways, and everything Central Florida has to provide. This is an excellent opportunity to own a well-located home in one of the most sought-after areas in Windermere.

12353 Via Derna Place, Windermere
$2,170,000
5 Beds ⋅ 7 Baths ⋅ Estancia/Windermere SubDv. ⋅ 34786 Zip Code
Elegant and spacious home in the highly sought after Estancia at Windermere community, offering the perfect blend of luxury, comfort, and prime Central Florida living. Built in 2019 on an oversized homesite, this beautifully appointed residence showcases modern architecture, generous living areas filled with natural light, and high end finishes throughout. The open concept layout is ideal for both everyday living and entertaining, with a gourmet style kitchen, elegant dining spaces, and seamless flow to the outdoor living area. Enjoy Windermere’s signature lifestyle just minutes from top rated schools, charming downtown Windermere, and world class Orlando attractions, including Walt Disney World and Universal Studios. Estancia is a boutique community of luxury homes featuring a private, serene atmosphere with conservation surroundings, while still offering quick access to major highways, shopping, dining, parks, and the Butler Chain of Lakes. This is an outstanding opportunity to own a stylish, move in ready home in one of Windermere’s most desirable neighborhoods.

1316 Estancia Woods Loop, Windermere
$1,099,000
4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Reduced 50k! Seller motivated! Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal dining, family room, and separate sitting area, all anchored by a gourmet chef’s kitchen featuring quartzite countertops, premium stainless steel appliances, and custom cabinetry—effortlessly flowing into expansive living and dining spaces ideal for both everyday comfort and refined entertaining. The luxurious primary suite offers a tranquil retreat with a sitting area, a spa-inspired en-suite bath, and a spacious walk-in closet. 2 of the additional bedrooms are split from the main suite, providing comfort and flexibility with a jack-n-jill bathroom. While a separate 4th bedroom is set apart from the others and can be used as a guest suite or office, it's in a perfect space for remote work or study. Outside, your private oasis awaits—a covered lanai overlooks a sparkling pool and lushly landscaped backyard, creating a serene setting for alfresco dining or lounging under the Florida sun. This residence is also zoned for A-rated schools, within minutes of Windermere’s charming shops, fine dining, and world-renowned attractions. (Roof Replace 2026), Driveway replaced 06/2026. This exceptional home invites you to experience the very best of Central Florida living. Schedule your showing today!

8351 Bowden Way, Windermere
$795,000
4 Beds ⋅ 4 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code
Discover the charm of this water front, 4 bedroom 3.5 bath home located in the desirable Summerport community. This unique property is nestled in the cul de sac for complete privacy. Enjoy scenic water views while relaxing poolside on the spacious screen enclosed lanai, which is also great for entertaining. The interior features granite countertops, stainless appliances, 42" cabinets, built in speakers on both levels and exterior. The community amenities include pool, fitness center, tennis courts, clubhouse, parks, dock, and walking paths. Conveniently located near theme parks, dining, and shopping.

5413 Walsh Pond Court, Windermere
$724,900
4 Beds ⋅ 3 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code
Short Sale. Super Rare Opportunity! Tucked away in one of Windermere’s most desirable areas is the beautiful home on over 1 half acre homesite on a corner lot with no rear neighbors and a gorgeous lake view. Don't sleep 'on' this home if you want to sleep 'in' this home! New roof 2023. Interior features include a fully remodeled kitchen with white 42" cabinets with crown moulding and gold hardware, custom vent hood with a tile backsplash. In addition a huge quartz centerpiece island with upgraded stainless steel appliances including a gas range plus a farmhouse sink. All overlooking the huge family room, 3 gold pendant lights and gold chandelier. New vinyl plank flooring throughout the entire first floor plus the stairs and loft on the 2nd floor. Spacious master suite with double sink vanity with garden tub and separate shower. 2 walk in closets as well. Formal living room, independent den/office with storage closet, half bath with custom vessel sink and indoor laundry room round out the first floor. Upstairs you will find the aforementioned loft along with 3 additional bedrooms and full bath with updated floor to ceiling tile and glass door shower. As you walk out onto the covered patio, along with the tremendous screen enclosed pool and spa you will find plenty of green grass to run and play in the fully fenced yard and if you need even more, utilize the greenspace to the side of the home as well. Enjoy the tranquil views of the serene lake from the back or relax on the extended covered front porch on a rocker from Cracker Barrel and if your in the mood for some ice cream or coffee, just a 5 minute walk from the front door is Kelly's Ice Cream and Foxtail coffee and even a pizza shop, and on your way you will pace by the "A" rated Keene Crossing Elementary school. .Additional community amenities include clubhouse with pool, tennis and basketball courts, sand volleyball and a private pier. Location benefits include easy access to Horizon West Town Center and all the monthly activities, Windermere Prep, Foundation Academy private schools, numerous restaurants and shopping, SR 429, Florida Turnpike and so much more!

14255 Sonco Avenue, Windermere
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