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Windermere is a town in west Orange County, Florida. It is considered part of the Orlando Metropolitan Statistical Area and known for its amazing lakes and being the community of the rich and famous. A highly sought after place to live, Windermere has a noble history that gives the town its modern charm. Founded in 1887, Windermere prides itself on many historical sites such as its Town Hall, Cal Palmer Memorial Building and the Parramore House aka Historic 1890 Windermere Schoolhouse. In 1925, Windermere was incorporated as a town. While its population has exploded over the last three decades, Windermere continues to retain many of its original roads and homes to honor its proud history. The Town of Windermere was recently voted the "Number One Top Choice Towns for Families with Children in the Sunshine State." The prestigious award was given by Neighborhood Scout, which combines data from the national, regional and local sources.

Windermere is a great place to live, raise a family, enjoy your career, or even choose to retire. It offers many housing options for all ages and interests and has become known for its famous sports, movie and television celebrities who call Windermere home, including:  Shaquille O'Neal, Wesley Snipes, Tiger Woods, Bubba Watson, Vince Carter, Joey Fatone, Johnny Damon, Delta Burke, Rick Goings, Ken Griffey Jr, Grant Hill, Philip Michael Thomas, Jim Courier and many more.

Windermere offers many forms of housing including luxury, waterfront, golf front, single-family homes, townhomes, condos, and villas. Prices range from $300K to over $20 million offering opportunities for all types of buyers. Some of the most desirable and elite communities in Central Florida are located in Windermere including Bellaria, Butler Bay, Casa Del Lago, Casabella, Cassabella At Windermere, Chaine Du Lac, Diamondhead, Estates At Lake Clarise, Gotha Town, Harbor Island, Isleworth, Keenes Pointe, Kelso On Lake Butler, Lake Burden, Lake Cypress Cove, Lake Davis Estates, Lake Davis Reserve, Lake Down Shores, Lakes of Windermere, Oxford Moor, Metcalf Park, Reserve At Lake Butler Sound, Sawyer Sound, Summerport Beach, Waterford Pointe, Waterstone, Weatherstone On Lake Olivia and many more.

Looking to sell your home in Windermere? Follow this link to get an "Instant" Home Value Report

Newest Windermere Homes for Sale

8531 Eagles Loop Circle, Windermere image
8531 Eagles Loop Circle, Windermere $725,000

Take advantage of a great opportunity to live in Keene’s Pointe in the private enclave of custom homes located within the Village of Lyndhurst. This custom home built ...

  • 4 Beds
  • 4 Baths
  • Keenes Pointe Ut 06 50 95 SubDv.
  • 34786 Zip Code
8620 Crescendo Avenue, Windermere image
8620 Crescendo Avenue, Windermere $399,900

Single story energy-efficient home with an open kitchen with center island/bar counter area, granite counter-tops, large walk in pantry, opening to inviting great room/fa...

  • 4 Beds
  • 3 Baths
  • Windermere Trails Ph 1c SubDv.
  • 34786 Zip Code
1113 Main Street, Windermere image
1113 Main Street, Windermere $499,900

Tropical Oasis in Windermere Among the Lakes! Large 1/3 Acre+ property with lush, mature landscaping. A true Vacation Paradise in your own backyard. Very large pool, i...

  • 4 Beds
  • 2 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
7045 Horizon Circle, Windermere image
7045 Horizon Circle, Windermere $1,500,000

Prime 1+ acre Windermere waterfront lot. 100’ on the Butler Chain of Lakes conveniently located walking distance to restaurants, shopping and fitness. On the fringe, but ...

  • Windermere Reserve SubDv.
  • 34786 Zip Code
620 Forest Street, Windermere image
620 Forest Street, Windermere $729,000

Rare new ENERGY STAR CERTIFIED, ICF construction home in the heart of Historic Downtown Windermere. Just steps from the weekly farmers market, monthly food trucks, and lo...

  • 4 Beds
  • 4 Baths
  • Marsh Sub SubDv.
  • 34786 Zip Code
12867 Butler Bay Court, Windermere image
12867 Butler Bay Court, Windermere $325,000

Amazing cul-de-sac lot available in Windermere Club. Build your own custom dream home here on the incredibly private and large lot. Current property taxes based upon pr...

  • Butler Bay SubDv.
  • 34786 Zip Code
6977 Nobleton Drive, Windermere image
6977 Nobleton Drive, Windermere $424,900

Popular community of Lakes of Windermere! This 2 story home features 4 bedrooms and 2.5 baths and is just what you are looking for! Great location with a green space acro...

  • 4 Beds
  • 2.5 Baths
  • Lakes Of Windermere Ph 01 49 108 SubDv.
  • 34786 Zip Code
13073 Lake Roper Court, Windermere image
13073 Lake Roper Court, Windermere $898,900

This stunning recently updated waterfront home features 5 bedrooms and 4 bathrooms on a 2.9-acre lot in the desirable town of Windermere. Situated on a secluded flag lot ...

  • 5 Beds
  • 4 Baths
  • Windermere Pointe At Lake Roper SubDv.
  • 34786 Zip Code
14339 Red Cardinal Court, Windermere image
14339 Red Cardinal Court, Windermere $439,000

This beautiful home is presented pristinely with its upgrades, major renovations estimated in $50K, and golf course views in the desirable Windermere community of Summerp...

  • 5 Beds
  • 2.5 Baths
  • Summerport Ph 05 SubDv.
  • 34786 Zip Code
83 Pine Street, Windermere image
83 Pine Street, Windermere $845,000

Welcome to 83 Pine Street! One of the most prestigious and coveted streets in Windermere. This home is located in the heart of Windermere which is situated among larg...

  • 4 Beds
  • 3.5 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
11654 Delwick Drive, Windermere image
11654 Delwick Drive, Windermere $539,000

Great opportunity to own this contemporary and luxurious retreat with an open space floor plan, brand new roof (30NOV/2019). Located in The Reserve at Belmere, a gated co...

  • 4 Beds
  • 3 Baths
  • Reserve At Belmere SubDv.
  • 34786 Zip Code
1230 Kelso Blvd, Windermere image
1230 Kelso Blvd, Windermere $765,000

Impressive Cathedral-style home with soaring vaulted ceilings, floor-to-ceiling Great Room windows, and monumental architecture – set on a full-acre, across the street fr...

  • 4 Beds
  • 3 Baths
  • Kelso On Lake Butler SubDv.
  • 34786 Zip Code
8796 Peachtree Park Court, Windermere image
8796 Peachtree Park Court, Windermere $635,000

This Key West Style former MODEL HOME is a MUST SEE! The spacious, immaculate Bimini floor plan is loaded with upgrades throughout the home and has a beautiful designer p...

  • 4 Beds
  • 3.5 Baths
  • Peachtree Park SubDv.
  • 34786 Zip Code
5145 Honeynut Lane, Windermere image
5145 Honeynut Lane, Windermere $415,000

SPECTACULAR 4 BEDROOM/2.5 BATH POOL HOME IN WINDERMERE! LOCATION SAYS IT ALL WHEN IT COMES TO THIS HOME! OH SO CLOSE TO SHOPPING AT THE ISLEWORTH CASCADES SHOPPING CENT...

  • 4 Beds
  • 2.5 Baths
  • Silver Woods Ph 05 SubDv.
  • 34786 Zip Code
13548 Gorgona Isle Drive, Windermere image
13548 Gorgona Isle Drive, Windermere $517,000

Home located in Windermere Isle is ready for a quick sale!!! This Energy Star Certified Luciana model home has 4-bedrooms, 3-baths! Walk up to its gorgeous stone features...

  • 4 Beds
  • 3 Baths
  • Windermere Isle 91/135 Lot 22 SubDv.
  • 34786 Zip Code
65 Pine Street, Windermere image
65 Pine Street, Windermere $2,995,000

Pre-Construction. To be built. Rare opportunity to own a 5-bedroom, 5-and-2-half-bath custom-built lakefront home in the town of Windermere! Through the impressive front ...

  • 5 Beds
  • 5.5 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
8498 Powder Ridge Trail, Windermere image
8498 Powder Ridge Trail, Windermere $547,280

Come see the only BUNGALOW of its kind for sale in Windermere Trails! This Corner LOT residence enjoyed many upgrades including a professionally designed outdoor area wit...

  • 4 Beds
  • 3.5 Baths
  • Windermere Trls Ph 3b SubDv.
  • 34786 Zip Code
4785 Blue Major Drive, Windermere image
4785 Blue Major Drive, Windermere $480,000

This Windermere two-story home offers a loft, granite countertops, and a two-car garage. This home is vacant and cleaned regularly.

  • 5 Beds
  • 3 Baths
  • Summerport Ph 05 SubDv.
  • 34786 Zip Code
13651 Reams Road, Windermere image
13651 Reams Road, Windermere $1,599,999

5+/- acres located within the most sought after area known as Windermere, Florida within the Horizon West Development Corridor. Rare opportunity for developer, investor,...

  • Acreage SubDv.
  • 34786 Zip Code
1124 Estancia Woods Loop, Windermere image
1124 Estancia Woods Loop, Windermere $985,000

The Monte Carlo model is FULL OF UPGRADES and DESIGNER DECORTION. Elegant courtyard design. Most open plan featuring single level living. Signature California Island with...

  • 4 Beds
  • 4.5 Baths
  • Estancia/Windermere SubDv.
  • 34786 Zip Code
8 Chase Road, Windermere image
8 Chase Road, Windermere $1,989,000

Beautiful Lakefront Home with over 190ft on Lake Butler and located in the Historic Town of Windermere. This 4bedroom 3.5 bath home has been completely rehabilitated betw...

  • 4 Beds
  • 3.5 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
6602 Bridgewater Village Road, Windermere image
6602 Bridgewater Village Road, Windermere $455,000

Welcome home! Bring your offer today! You will love this beautiful 2-story, Windermere home. This 5-bedroom, 3-bathroom, 2 car garage house. The outdoor kitchen will make...

  • 5 Beds
  • 3 Baths
  • Vineyards/Horizons West Ph 1b SubDv.
  • 34786 Zip Code
5049 Latrobe Drive Drive, Windermere image
5049 Latrobe Drive Drive, Windermere $1,850,000

Majestic golf course views abound from this beautifully-crafted Isleworth estate. Situated on the 6th fairway in the main phase of the Isleworth Golf & Country Club, thi...

  • 5 Beds
  • 4.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
13161 Lake Butler Boulevard, Windermere image
13161 Lake Butler Boulevard, Windermere $1,750,000

Extraordinary lake front opportunity in Windermere on 1.75 acres! This estate could house a family compound for the individual seeking security and privacy with it's own ...

  • 5 Beds
  • 3.5 Baths
  • Lake Roper Pointe SubDv.
  • 34786 Zip Code
38 Orange Isle Drive, Windermere image
38 Orange Isle Drive, Windermere $418,590

Pre-Construction. To be built. The Sanctuary at Lakes of Windermere is the perfect sanctuary for living in Central Florida’s most desired suburb. The Sanctuary is located...

  • 4 Beds
  • 2.5 Baths
  • The Sanctuary At Lakes Of Windermere SubDv.
  • 34786 Zip Code

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