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Windermere Homes for Sale

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

8360 Vivaro Isle Way, Windermere image
8360 Vivaro Isle Way, Windermere $446,900

Under Construction. Ready in August, second image depicts actual exterior color scheme. Enjoy a cup of coffee and sunrises from your front porch as you wake up refreshed ...

  • 4 Beds
  • 3 Baths
  • Windermere Isle SubDv.
  • 34786 Zip Code
101 Lee Street, Windermere image
101 Lee Street, Windermere $825,000

RARE opportunity in the Town of Windermere! This 4,200 square foot 5 bedroom updated home is a must see! Beautifully situated on a hill, you will enjoy the views of the t...

  • 5 Beds
  • 4 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
Windermere image
Windermere $699,000

There is so much to love about this home located in the village of Camden within the Guard-gated golf community of Keene's Pointe. Open and functional layout of living sp...

  • 4 Beds
  • 3 Baths
  • 34786 Zip Code
6952 Mapperton Drive, Windermere image
6952 Mapperton Drive, Windermere $515,000

Spectacular pond front Windermere residence. Prepare to be impressed by this homes stunning upgrades, including porcelain tile throughout, crown molding, plantation shutt...

  • 5 Beds
  • 3 Baths
  • Lakes Windermere Ph 01 49 108 SubDv.
  • 34786 Zip Code
Windermere image
Windermere $329,000

Your 1903 SF 2-story single family home includes a lovely covered front porch overlooking the beautifully landscaped community. Tranquility and peace surrounds you. Open ...

  • 3 Beds
  • 2.5 Baths
  • 34786 Zip Code
6803 Valhalla Way Unit 3, Windermere image
6803 Valhalla Way Unit 3, Windermere $1,495,000

Beautifully sited Mediterranean Villa, with Breathtaking Panoramic Golf Course Views awaits new owners. As you approach this Custom built home, you are greeted by a Gated...

  • 5 Beds
  • 5.5 Baths
  • Keenes Pointe 46/104 SubDv.
  • 34786 Zip Code
7604 Colbury Avenue, Windermere image
7604 Colbury Avenue, Windermere $375,000

The best lot in the entire Community!! You will see Disney's Fireworks all night from your backyard. Berkshire Park is located in Windermere, 4 bedrooms 2 baths and 2 car...

  • 4 Beds
  • 2 Baths
  • Lake Sawyer South Ph 02 SubDv.
  • 34786 Zip Code
6046 Blakeford Drive Unit 1, Windermere image
6046 Blakeford Drive Unit 1, Windermere $659,000

GREAT LOCATION , GREAT PRICE, GREAT HOUSE, ON MUCH DISERED STREET IN KEENE'S POINTE!! Come home to one of the most desired oak tree canopied streets in all of Keene's Poi...

  • 4 Beds
  • 4 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
5848 Oxford Moor Boulevard, Windermere image
5848 Oxford Moor Boulevard, Windermere $769,900

Please bring your Buyers and Investors to this Breathtaking Waterfront Luxurious Pool and Spa Home, located in a Magnificent Virtual-Guard Gate Windermere Subdivision! Ho...

  • 5 Beds
  • 4.5 Baths
  • Oxford Moor 47/30 SubDv.
  • 34786 Zip Code
12831 Cragside Lane, Windermere image
12831 Cragside Lane, Windermere $356,900

Welcome to your new home in the desirable Lake of Windermere community. This Delightful, Open Concept Home Features both Formal and Informal Living Spaces. Luxury Featu...

  • 4 Beds
  • 2.5 Baths
  • Lakes Of Windermere Ph 02a SubDv.
  • 34786 Zip Code
2021 Westover Reserve Boulevard, Windermere image
2021 Westover Reserve Boulevard, Windermere $769,000

Enjoy the Windermere lifestyle in this stunning home located in the gated community of Westover Reserve. Excellent curb appeal and professionally landscaped grounds highl...

  • 6 Beds
  • 5.5 Baths
  • Westover Reserve Ph 02 SubDv.
  • 34786 Zip Code
9530 Kingsbury Court, Windermere image
9530 Kingsbury Court, Windermere $639,000

Located on a half acre on a cul-de-sac in Windsor Hill this impeccably maintained 4 bedroom, 3.5 pool home with 14 ft ceilings in the kitchen and family room is all on on...

  • 4 Beds
  • 3.5 Baths
  • Windsor Hill SubDv.
  • 34786 Zip Code
13037 Water Point Boulevard, Windermere image
13037 Water Point Boulevard, Windermere $1,100,000

This beautiful Lakefront home features a total of 4,686 Sq ft air conditioned space of which 3,390 are a 3 bedroom plus office home and a 1,296 sq ft air-conditioned RV g...

  • 3 Beds
  • 3.5 Baths
  • Waterford Pointe Ph 02 Rep SubDv.
  • 34786 Zip Code
5408 Gemgold Court, Windermere image
5408 Gemgold Court, Windermere $410,000

Location says it all! In the popular community of Summerport, in the city of Windermere, this community remains one of the most popular neighborhoods in the area. The bac...

  • 4 Beds
  • 2.5 Baths
  • Eden's Hammock SubDv.
  • 34786 Zip Code
5818 Oxford Moor Boulevard, Windermere image
5818 Oxford Moor Boulevard, Windermere $300,000

PROPERTY IN NEED OF SOME REPAIRS, COST OF REPAIRS ARE UNKNOWN. HIGHEST AND BEST OFFERS. WATER DAMAGE AND MOLD. HOUSE IS BACK ON THE MARKET AFTER INSPECTION REPORT, ESTIMA...

  • 6 Beds
  • 4 Baths
  • Oxford Moor 47/30 SubDv.
  • 34786 Zip Code
1711 Maple Leaf Drive, Windermere image
1711 Maple Leaf Drive, Windermere $498,000

Welcome to Florida living at its finest in this renovated 4 Bedroom and 2.5 Bath Mediterranean Home. Immediately upon driving up, you are greeted with lovely TILE ROOF an...

  • 4 Beds
  • 2.5 Baths
  • Windermere Downs 1st Add SubDv.
  • 34786 Zip Code
6538 Chagford Lane, Windermere image
6538 Chagford Lane, Windermere $375,000

Make your appointment today to view this 4 bedroom + loft, and 3 full bathroom home in the Lakes of Windermere community. Walking into the foyer is your formal living roo...

  • 4 Beds
  • 3 Baths
  • Lakes Of Windermere Ph 2a SubDv.
  • 34786 Zip Code
8657 Lookout Pointe Drive, Windermere image
8657 Lookout Pointe Drive, Windermere $495,900

This home is located on a corner lot offering front porch living that overlooks conservation. It offers 4 bedrooms, 3.5 baths, optional den and bonus room with a 2-car ga...

  • 4 Beds
  • 3.5 Baths
  • Windermere Trls Ph 1c SubDv.
  • 34786 Zip Code
14166 Eden Isle Boulevard, Windermere image
14166 Eden Isle Boulevard, Windermere $475,000

Stunning 4BR pool home w/canal view-experience the WOW factor with every turn. You'll be impressed from the moment you arrive. Nicely landscaped front, quaint front porch...

  • 4 Beds
  • 3 Baths
  • West Point Commons SubDv.
  • 34786 Zip Code
6321 Greatwater Drive, Windermere image
6321 Greatwater Drive, Windermere $5,999,999

Welcome to Maison des Fleurs in Keene’s Pointe in Windermere, Florida. Custom estate home located on a private cove on Lake Tibet, of the Butler Chain of Lakes. Offering ...

  • 6 Beds
  • 6.5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
6298 Golden Dewdrop Trail, Windermere image
6298 Golden Dewdrop Trail, Windermere $320,000

This Modern and stylish home is the one you've been looking for! Located in desired heart of Windermere with all its privileges. This 3 bedroom, 2.5 bath home has it all....

  • 3 Beds
  • 2.5 Baths
  • Windermere Lndgs Ph 02 SubDv.
  • 34786 Zip Code
4205 Clarice Ests Drive, Windermere image
4205 Clarice Ests Drive, Windermere $1,025,000

Enter through the stately 12 foot iron and glass doors from the convenience of a courtyard driveway. This unique design offers formal living room and dining room privacy,...

  • 4 Beds
  • 5 Baths
  • Estates At Lake Clarice SubDv.
  • 34786 Zip Code
7684 Ripplepointe Way, Windermere image
7684 Ripplepointe Way, Windermere — 7684 $305,000

LOCATION - LOCATION . Come see this beautiful modern townhome located in the subdivision of Lake Burden in Windermere FL. 4 BR 3 BA. Located in the Community Lake burden ...

  • 4 Beds
  • 3 Baths
  • Lake Burden South Ph 2 #35 36 SubDv.
  • 34786 Zip Code
5624 Remsen Cay Lane, Windermere image
5624 Remsen Cay Lane, Windermere $399,900

Former model home. Make this your Florida getaway. This 4 bedroom 3 bathroom is in immaculate condition. Located in Eden's Hammock and is in the best school district z...

  • 4 Beds
  • 3 Baths
  • Edens Hammock SubDv.
  • 34786 Zip Code
7266 Londale Boulevard, Windermere image
7266 Londale Boulevard, Windermere $394,000

Come settle into the best school district in Orange County. A new 2nd floor central AC was installed in June of 2018 and over $5,000 in home refresh is scheduled the last...

  • 5 Beds
  • 3.5 Baths
  • Enclave / Berkshire Park B G H I SubDv.
  • 34786 Zip Code

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