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

$1,499,900
5 Beds ⋅ 6 Baths ⋅ Windsor Hill SubDv. ⋅ 34786 Zip Code
UPDATED PHOTOS! Rare opportunity to purchase in the Windermere's Windsor Hill community on a quiet cul-de-sac. This spacious 5-bedroom home offers over 5,300 square feet of flexible living space designed for both everyday living and entertaining. Situated on nearly half an acre, the property features a functional layout with large gathering spaces, high ceilings, and plenty of natural light throughout. The kitchen includes stainless steel appliances, ample cabinet space, a center island, and connects directly to the main living areas, making it ideal for hosting or family life. The first-floor primary suite offers dual walk-in closets and a large ensuite bath, while the additional bedrooms and living spaces provide room for guests, work-from-home setups, or multigenerational living. One of the standout features of the home is the custom Indiana Jones-themed movie room, creating a unique and immersive entertainment space. The home also includes a bonus enclosed patio area that can function as a home gym or creative workspace. Outside, enjoy a large backyard, covered outdoor areas, and a private pool setting perfect for Florida living. Conveniently located near top-rated schools, shopping, dining, and major roadways, this Windermere home combines size, character, and functionality in a desirable location.

9527 Queensbury Court, Windermere
$1,450,000
5 Beds ⋅ 5 Baths ⋅ Reserve At Lake Butler Sound SubDv. ⋅ 34786 Zip Code
Located within the guard gated community of Reserve at Lake Sound in Windermere, this beautifull 5-bedroom, 5-bath residence offers the perfect blend of elegance, comfort, and functionality. Featuring nearly 3,900 square feet of living space, the home showcases tall ceilings, travertine flooring throughout the main living areas, and thoughtful modern updates completed in recent years. A grand double-door entry opens to formal living and dining spaces highlighted by contemporary accent walls and a striking fireplace. The spacious kitchen is designed for both everyday living and entertaining, featuring upgraded stainless steel appliances, abundant cabinetry, stylish countertops, a beverage refrigerator, and an open flow into the family room. The split-bedroom floor plan includes a private office and a spacious primary suite complete with California closets and a luxurious ensuite bath featuring dual vanities, a walk-in shower, and a freestanding soaking tub. Upstairs, the oversized bonus room with full bath offers flexibility as a guest suite, second primary suite, or media room. Sliding doors lead to an expansive screened pool area ideal for relaxing or entertaining, while the lush backyard garden creates a peaceful setting to enjoy your morning coffee. The home also features a spacious 3-car garage. *Roof and water heater was replaced 5 years ago.* Ideally located near top-rated schools, shopping, dining, and area attractions, this move-in ready Windermere home is one you won’t want to miss.

11015 Hawkshead Court, Windermere
$1,130,643
4 Beds ⋅ 4 Baths ⋅ Palms At Windermere SubDv. ⋅ 34786 Zip Code
One or more photo(s) has been virtually staged. Under Construction. Arlington Floorplan – 3,153 Sq. Ft. | 4 Beds | 4 Baths | 2.5-Car Garage | Arlington with Bonus Room – a thoughtfully designed, 1-story home plus a Bonus Room on the 2nd floor that perfectly blends luxury, functionality, and comfort. This brand new 3,153 square foot residence sits on a wooded lot, offering expansive indoor and outdoor living space. 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, a large center island, upgraded cabinetry, quartz countertops, a 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. Projected Completion August/September. Preferred Lender incentives apply.

14341 Crest Palm Avenue, Windermere
$1,450,000
4 Beds ⋅ 4 Baths ⋅ Windsor Hill SubDv. ⋅ 34786 Zip Code
Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s modern buyer in mind. The stunning chef’s kitchen is a true showpiece, appointed with brand-new premium Thermador appliances, custom cabinetry, designer finishes, and elegant lighting that elevate the entire living experience. Wide-plank luxury vinyl flooring flows seamlessly throughout the home, combining sophistication with durability and low-maintenance living. Designed for both everyday comfort and entertaining, the flexible floor plan includes an oversized upstairs BONUS ROOM, with a built-in-closet and a full bathroom, ideal for a home theater, game room, executive office, fitness studio, or private guest retreat/in-law suite. Major upgrades provide exceptional value and peace of mind, including a 2021 roof, dual high-efficiency HVAC systems (2 units/ 2026), new water heater, upgraded sliding glass doors, and an epoxy-coated garage. The expansive backyard offers endless possibilities to create your dream outdoor oasis, resort-style pool, or entertaining space. Located just minutes from the renowned Butler Chain of Lakes, championship golf courses, upscale dining, shopping, and top-rated schools, this exceptional property combines luxury, privacy, and convenience in one of Central Florida’s most desirable locations. Rarely does a fully updated home with this level of quality, land, and location become available. Some photos have been virtually staged. Furnishings shown are for illustrative purposes only and are not included in the sale.

9548 Crown Prince Lane, Windermere
$549,900
Roberts Landing SubDv. ⋅ 34786 Zip Code
Location, Location, Location!! Windermere Lot: 2.62 acres, with 1 acre buildable, for an incredible luxury designer estate with partial water views of Lake Olivia and a stream. NO HOA REQUIRED! Bring your custom builder. When you see this land, you will admire the beauty of nature. Gorgeous conservation views and spacious areas between the homes in the community. Nestled in the heart of Central Florida, the city of Windermere, FL, is a charming lakeside town boasting a rich history, luxurious real estate, and an exceptional quality of life. With easy access to Orlando's world-famous attractions, Windermere, Florida, offers the perfect balance between serene lakeside living and vibrant city life. Top-rated schools, fine dining, shopping, world-class golf, theme parks, and quick access to major expressways. Roberts Landing in Windermere, FL, is located on the east shore of Lake Olivia. The main entrance is on Westover Roberts Road across from Westover Club and Westover Reserve, two other Windermere, FL, communities. The streets here are winding and well-shaded, like most mature Windermere communities. Lake Olivia in north Windermere, FL, is a private lake. This rare lot in Windermere is an incredible opportunity. Build the luxury estate of your dreams.

1661 Roberts Landing Road, Windermere
$430,000
3 Beds ⋅ 3 Baths ⋅ Legado 95/47 Lot 100 SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home featuring a spacious loft area perfect for a home office, media room, or play space. This move-in ready property offers an open-concept layout, stylish finishes, abundant natural light, and comfortable living spaces throughout. Located in the highly desirable Windermere area, this home offers easy access to top-rated schools, shopping, dining, major highways, and Orlando attractions. Enjoy the perfect blend of comfort, convenience, and Florida living in a great location!

8866 Herencia Aly, Windermere
$27,000,000
7 Beds ⋅ 10 Baths ⋅ Na SubDv. ⋅ 34786 Zip Code
A rare legacy estate of extraordinary scale and architectural significance, this magnificent lakefront compound spans over 22,000 square feet across more than 11 private acres with over 440 feet of pristine frontage on Cypress Lake. Masterfully designed to deliver the ultimate blend of grandeur, privacy, and resort-inspired living, the residence is statement of uncompromising luxury. Beyond the gated entrance, a sweeping motor court and dramatic porte-cochère introduce the home’s commanding Mediterranean-inspired architecture, where turreted wings, natural stone detailing, and elegant arched windows create an unforgettable arrival experience. Inside, a breathtaking 28-foot grand foyer unfolds beneath soaring ceilings, anchored by a spectacular double staircase with intricate custom ironwork that evokes the elegance of a world-class villa. Flooded with natural light through towering arched windows, the space immediately establishes the scale and sophistication that define the estate. Designed for intimate living and large-scale entertaining, the interiors blend timeless craftsmanship with modern refinement. The gourmet chef’s kitchen is a showpiece of its own, featuring custom wood cabinetry, expansive stone countertops, professional-grade appliances, a dramatic custom range hood, oversized center island, hidden pantry and richly detailed ceiling treatments that elevate the space into a culinary centerpiece. Adjacent gathering areas showcase exposed wood beams, designer lighting and seamless indoor-outdoor connectivity, creating warm yet grand living environments ideal for entertaining on any scale. Every amenity within the residence has been thoughtfully curated to rival the finest luxury resorts. Highlights include a state-of-the-art theater, golf simulator, multiple game rooms, an expansive wine room, private elevator, smart home automation system and a fully equipped fitness center. Elegant fireplaces and sophisticated entertaining spaces add warmth and intimacy throughout the home. A private guest wing with two bedrooms, its own living room, and separate entrance offers luxurious accommodations for extended family, guests or staff. The outdoor experience is nothing short of spectacular. The rear elevation unfolds around a breathtaking 125,000-gallon resort-style pool complete with cascading waterfalls, bordered by natural stones, a water slide, diving board and expansive terraces that rival five-star destinations. At twilight, the towering palms and illuminated architecture reflect across the shimmering water, creating a setting reminiscent of an exclusive private resort with intimate lounge settings that invite grand entertaining and quiet moments of retreat. For the automotive enthusiast, the estate includes a 10-car garage equipped with two vehicle lifts. Recreational amenities continue across the grounds with a private basketball court, boat dock and private community boat ramp, which provide effortless access to the desired Butler Chain of Lakes for world-class boating and waterfront living. Surrounded by expansive lawns, mature landscaping and unmatched privacy, this extraordinary residence represents a once-in-a-generation opportunity to own a waterfront legacy estate, a property designed not only to impress, but to endure for generations to come.

5603 Marleon Drive, Windermere
$1,572,000
4 Beds ⋅ 2 Baths ⋅ Davis Shores SubDv. ⋅ 34786 Zip Code
BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress trees line the beautiful serene canal leading directly to the 12 lakes of the Butler Chain. PRIVATE FINANCING IS AVAILABLE - (ask for terms and conditions). Access the Butler chain of lakes from your back yard to Lake Down or Lake Wauseon. Renovate or Build your own modern upscale dream home. Town of Windermere residents can access Fernwood Park and boat ramp 8/10 mile away. Drive your Golf Cart to downtown Windermere. Multiple possibilities for this property in the prime location of Windermere. Home needs major renovation or demolish and rebuild. Sold AS IS.

33 Main Street, Windermere
$1,350,000
4 Beds ⋅ 3 Baths ⋅ Reserve At Belmere SubDv. ⋅ 34786 Zip Code
Price Improvement! Located behind the gates of the prestigious Reserve at Belmere in sought-after Windermere, this exceptional Mediterranean-inspired estate offers a rare blend of timeless architecture, modern luxury and thoughtful custom enhancements. Built in 2004 by the original owners and expanded during construction, the residence offers more than 3,427 square feet of refined living space and over 4,528 total square feet, creating a larger footprint than many comparable homes within the community. Extensively upgraded with more than $250,000 in recent improvements, this meticulously maintained home showcases true pride of ownership. Significant updates completed within the last three years include three new Trane HVAC systems, replacement windows, premium appliances, pool renovations, designer lighting and numerous interior and exterior enhancements. From the moment you enter, soaring 24-foot ceilings and elegant architectural details set the tone. Crown molding, coffered ceilings, engineered hardwood flooring, custom window treatments and a marble wood-burning fireplace create a sophisticated yet inviting atmosphere. Expansive glass sliding doors frame the outdoor living spaces and provide seamless indoor-outdoor flow ideal for everyday living and entertaining. The chef’s kitchen has been thoughtfully curated with luxurious quartzite countertops, custom pullout cabinetry with rotating shelving systems and an impressive suite of premium German appliances, including a Miele built-in coffee system, convection oven, dishwasher and refrigerator. A professional-grade 48-inch chef gas range with six burners and a griddle, custom lighting and a built-in three-stage water filtration system complete the space. Privately on the main level, the primary suite offers a tranquil retreat with coffered ceilings, newly installed commercial-grade carpeting, serene pool views and direct patio access. The spa-inspired primary bath is appointed with marble and travertine finishes, a soaking tub, a separate shower and custom walk-in closet built-ins. Upstairs, generously sized secondary bedrooms and a spacious loft overlook the formal living and dining areas below. Designed for elevated outdoor living, the resort-style backyard features a resurfaced saltwater pool and spa, an updated pool heater, decorative fountains, remote-controlled pool systems and multiple entertaining areas surrounded by lush European-inspired landscaping, stone pathways and manicured grounds. Canary palms and mature landscaping create a private, luxurious setting. Additional highlights include a new front entry door, an oversized three-car garage, an upgraded security system, a partial roof replacement and designer chandeliers and lighting throughout. Ideally located in one of Windermere’s premier gated communities, residents of Reserve at Belmere enjoy convenient access to top-rated schools, dining, shopping, golf, major roadways and the area’s renowned luxury lifestyle offerings.

1554 Lake Rhea Drive, Windermere
$440,000
3 Beds ⋅ 3 Baths ⋅ Windermere Sound Ph 2 SubDv. ⋅ 34786 Zip Code
Beautiful two-story townhome in the desirable Windermere Sound community! This stunning residence offers 3 bedrooms, 2.5 bathrooms, and a spacious 2-car garage, spanning 1,742 sq. ft. of elegant living space. The home features stainless steel appliances, granite countertops, and modern finishes throughout. Windermere Sound provides residents with resort-style amenities, including a swimming pool, tennis and basketball courts, playgrounds, and scenic ponds, all with lawn care included. Ideally situated just minutes from Disney World, premium shopping, fine dining, and top-rated schools such as Windermere High School, this home perfectly blends comfort, convenience, and luxury living in one of Orlando's most sought-after areas.

7612 Fairgrove Avenue, Windermere
$940,000
4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Keene's Pointe - 24-hour gated/attended community in Windermere, Florida. 4 bedroom/3 bath home with formal living and dining rooms, kitchen and great room. This quaint home features a functional floor plan. Kitchen with newer stainless appliances, open concept floor plan joining the kitchen, nook and great room and private primary with walk-in closet and bath with dual vanities, shower and garden tub. Enjoy peaceful evenings in the private back yard with spacious lanai, screened oversized pool and large yard. The fourth bedroom is currently being used as a den with French doors. NEW ROOF IN 2022, WATER HEATER 2020, two car garage with storage, and much more. Discover all this community has to offer, including The Golden Bear Club, a private 18-hole golf course designed by Jack Nicklaus offering golf, tennis, swimming, dining and clubhouse. Located close to shopping, dining, expressways and top-rated public and private schools, this home is perfect as a primary home or vacation home. Call today for you private viewing.

8525 Bowden Way, Windermere
$6,995,000
5 Beds ⋅ 8 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Set along the pristine shores of Lake Tibet Butler, this exceptional estate within Keene's Pointe is a masterclass in timeless design, refined craftsmanship, and elevated lakefront living. Spanning over 7,500 square feet, every detail has been thoughtfully curated to balance grandeur with comfort. This home is meticulously cared for with improvements which recent improvements such as a new tile 250k roof (August 2024) and upgraded dock system, ensuring both beauty and peace of mind for years to come. A dramatic foyer makes a lasting first impression, overlooking formal living and dining spaces defined by architectural ceilings, designer lighting, and rich travertine flooring. At the heart of the home, the gourmet kitchen is both stunning and functional—featuring professional-grade appliances, custom cabinetry, stone countertops, and an expansive island that seamlessly connects to the dining area and inviting family room. Designed for entertaining, a showstopping game room features a 2,000-gallon saltwater aquarium—famously showcased in The Wall Street Journal—while French doors throughout the main living areas open to a fully screened resort-style patio. Here, a spa, fireplace, and summer kitchen create the ultimate indoor-outdoor living experience. The owner’s suite offers a true private retreat, complete with a fireplace, sitting area, wet bar, and dual dressing rooms—including a two-story boutique-style closet with an adjoining massage room. The spa-inspired bath features a soaking tub and steam shower, delivering a serene, resort-like escape. The main level also includes a private guest suite, a dedicated office with built-in safe, and an oversized laundry and utility space designed for both efficiency and versatility. Upstairs, a fully equipped fitness room and three additional en-suite bedrooms with sleek, modern finishes provide comfort and privacy for family and guests. Outdoors, lush landscaping and mature trees frame a tranquil setting designed for both relaxation and connection to nature. Meandering pathways lead past fountains and gardens to a secluded fire pit beside a gentle stream, while a charming bridge guides you to a private dock on the lake—enhanced with a Trex system for lasting durability. Located within the guard-gated community of Keene’s Pointe—home to the Jack Nicklaus Signature Golf Course at Golden Bear Club and offering direct access to the Butler Chain of Lakes—this residence represents a rare opportunity to own a true legacy property.

9349 Tibet Pointe Circle, Windermere
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