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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.

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Newest Windermere Homes for Sale

7358 Tattant Boulevard, Windermere image
7358 Tattant Boulevard, Windermere $394,900

STUNNING executive style home in the Berkshire Park Subdivision in Windermere. Impressive and meticulously maintained home that is 4 bedrooms, 3 1/2 baths and well-appo...

  • 4 Beds
  • 3.5 Baths
  • Lake Sawyer South Ph 01 SubDv.
  • 34786 Zip Code
8449 Greenbank Boulevard, Windermere image
8449 Greenbank Boulevard, Windermere $385,000 ▲

**Click on the Interactive Tour** Private pool home featuring one of the largest floor plans in the community, Disney Fireworks at night, a real 3 Car Garage, wooded back...

  • 4 Beds
  • 3.5 Baths
  • Lakes/Windermere-Peachtree SubDv.
  • 34786 Zip Code
6207 Cypress Chase Drive, Windermere image
6207 Cypress Chase Drive, Windermere $2,250,000

Immerse yourself in Mediterranean style living inside this exceptional two-story fully furnished and expertly decorated executive estate. This brilliant estate is locate...

  • 5 Beds
  • 5.5 Baths
  • Isleworth West SubDv.
  • 34786 Zip Code
8754 Peachtree Park Court, Windermere image
8754 Peachtree Park Court, Windermere $415,000

Welcome to this meticulously maintained 3 bed 2 bath Windermere home boasting 1,710 sf of living space, practically walking distance to Disney and shopping. The pavered d...

  • 3 Beds
  • 2 Baths
  • Peachtree Park SubDv.
  • 34786 Zip Code
4754 Blue Major Drive, Windermere image
4754 Blue Major Drive, Windermere $365,000

Absolutely charming home in the desirable Windermere community of Summerport! This 4 bed, 3 full bath, and 2 car garage home features, beautiful laminate floors in Master...

  • 4 Beds
  • 3 Baths
  • Summerport Ph 05 SubDv.
  • 34786 Zip Code
6564 Lagoon Street, Windermere image
6564 Lagoon Street, Windermere $328,800

Windermere Lake front is a rare find, even rarer in this price range with no HOA. Bring your own builder and build your dream home on private ski Lake Sawyer with Disney ...

  • Sawyer Shores SubDv.
  • 34786 Zip Code
7935 Jailene Drive, Windermere image
7935 Jailene Drive, Windermere $420,000

Beautiful 4-BR/3.5 -BA home w/den and 2,922 SF of living space in The Reserve at Berkshire Park. This stunning home sits on a corner lot w/an oversized 3-car garage. Buil...

  • 4 Beds
  • 3.5 Baths
  • Lake Sawyer South Ph 05 SubDv.
  • 34786 Zip Code
2118 Ridgewind Way, Windermere image
2118 Ridgewind Way, Windermere $599,000

Appraised prior to listing! WOW! Welcome to this extraordinary, immaculate, executive estate home located within the private gates of the “Estates at Windermere” and only...

  • 4 Beds
  • 3 Baths
  • Estates At Windermere First Add SubDv.
  • 34786 Zip Code
5137 Tildens Grove Boulevard, Windermere image
5137 Tildens Grove Boulevard, Windermere $1,200,000

This custom luxury 6 bed.,4,5 bath.,5300 sq ft home is located on over half an acre private lot in guard gated Tildens Grove. It just minutes away from fine dining, world...

  • 6 Beds
  • 4.5 Baths
  • Tildens Grove Ph 01 47/65 SubDv.
  • 34786 Zip Code
8351 Bowden Way, Windermere image
8351 Bowden Way, Windermere $569,000

“JEWEL BOX” IS THE TERM THAT COMES TO MIND WHEN YOU ENTER THIS PERFECTLY MAINTAINED 4 BEDROOM/3 BATH POOL HOME WITH ABUNDANT UPDATES AND FEATURES TO BE ENJOYED! START ...

  • 4 Beds
  • 3 Baths
  • Keenes Pointe Unit 1 SubDv.
  • 34786 Zip Code
6022 Blakeford Drive, Windermere image
6022 Blakeford Drive, Windermere $749,000

Sellers are motivated & have spent in excess of $120,000 on additions and upgrades! The home sits on one of the most beautiful streets in Keenes Pointe with both golf & ...

  • 4 Beds
  • 4 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
13316 Bellaria Circle, Windermere image
13316 Bellaria Circle, Windermere $1,800,000

One or more photo(s) has been virtually staged. Luxury living and at home comfort come together at this stunning Mediterranean style property! This beautiful home sits on...

  • 6 Beds
  • 6.5 Baths
  • Bellaria SubDv.
  • 34786 Zip Code
1131 Lascala Drive, Windermere image
1131 Lascala Drive, Windermere $505,000

Stunning Belmere home featuring 5 bedrooms and 5.5 baths PLUS a downstairs bonus room that could serve as a mother in law suite, game room, office or second master. Hardw...

  • 6 Beds
  • 5.5 Baths
  • Belmere Village G2 SubDv.
  • 34786 Zip Code
13796 Ingelnook Drive, Windermere image
13796 Ingelnook Drive, Windermere $375,000

The best value in WINDERMERE! Immaculate 3 bedroom, 3 bath features a spacious layout with a split bedroom floor plan and a den that could be an optional 4th bedroom. Se...

  • 3 Beds
  • 3 Baths
  • Vineyards/Horizons West Ph 1b SubDv.
  • 34786 Zip Code
7231 Sangalla Drive, Windermere image
7231 Sangalla Drive, Windermere $695,000

Beautiful Windermere home in gated Casa Del Lago boasts over 3800 square feet of luxury living. The two story floor plan has a huge bonus room and extra bedroom on the se...

  • 5 Beds
  • 4.5 Baths
  • Casa Del Lago SubDv.
  • 34786 Zip Code
9815 Laurel Valley Drive, Windermere image
9815 Laurel Valley Drive, Windermere $4,000,000

The house situated in the southwest suburb of Windermere.

  • 5 Beds
  • 5 Baths
  • Isleworth 1st Amendment SubDv.
  • 34786 Zip Code
11220 Ledgement Lane, Windermere image
11220 Ledgement Lane, Windermere $549,000

Stunning, fully updated, move-in ready pool home on large lot in gated community in Windermere. Modern kitchen with all new stainless steel appliances. Custom made but...

  • 4 Beds
  • 3.5 Baths
  • Glenmuir 48 39 SubDv.
  • 34786 Zip Code
6239 Rydal Court, Windermere image
6239 Rydal Court, Windermere $949,000 ▼

LUXURY LIVING! 5 Bedroom 4.5 Bathroom Spanish Mediterranean style custom-built ESTATE pool home in the exquisite 24/7 Guard-Gated RESERVE AT LAKE BUTLER SOUND! The doubl...

  • 5 Beds
  • 4.5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
8929 Blue Mesa Drive, Windermere image
8929 Blue Mesa Drive, Windermere $550,000

Live like you are on vacation every day in this MOVE-IN READY HOME! This STUNNING HOME offers serene WATER VIEWS and is nestled within the highly sought-after Windermere ...

  • 5 Beds
  • 4 Baths
  • Windermere Trls Ph 1 SubDv.
  • 34786 Zip Code
919 Algare Loop, Windermere image
919 Algare Loop, Windermere $545,000

One or more photo(s) has been virtually staged. Beautiful home in gate community BELMERE VILLAGE in WINDERMERE, A former model home by Taylor Morrison Builder, fresh pai...

  • 5 Beds
  • 4 Baths
  • Belmere Village G3 48 70 SubDv.
  • 34786 Zip Code
5024 Blue Major Drive, Windermere image
5024 Blue Major Drive, Windermere $379,990

Welcome Home... this beautiful 2-Story 4 bedroom, 2.5 bathroom home which sits on a pond in the highly sought after Summerport neighborhood is now ready for new owners. U...

  • 4 Beds
  • 2.5 Baths
  • Creeks Run SubDv.
  • 34786 Zip Code
5408 Marleon Drive, Windermere image
5408 Marleon Drive, Windermere $967,000

Traditional and contemporary meld perfectly in this custom-built home on 2/3 acre in the heart of Windermere. Situated on a cul-de-sac in gated Lake Davis Reserve, the We...

  • 4 Beds
  • 3 Baths
  • Lake Davis Reserve SubDv.
  • 34786 Zip Code
12821 Holdenbury Lane, Windermere image
12821 Holdenbury Lane, Windermere $369,000

WOW! Don’t miss out on this BEAUTIFUL WINDERMERE GEM! Biking distance to top schools and zoned for desirable Windermere High school! Freshly painted inside and out this M...

  • 4 Beds
  • 2.5 Baths
  • Lakes Of Windermere SubDv.
  • 34786 Zip Code
8376 Lookout Pointe Drive, Windermere image
8376 Lookout Pointe Drive, Windermere $700,000

More pictures coming soon! Beautiful Home in Windermere Trails, Breathtaking lake views of Lake reams, Spacious Hawthorne floor plan by Meritage Homes. Tons of upgrades. ...

  • 7 Beds
  • 4.5 Baths
  • Windermere Trls Ph 3b SubDv.
  • 34786 Zip Code
12000 Silverlake Park Drive, Windermere image
12000 Silverlake Park Drive, Windermere $345,000

Great oportunitty to own a Home in this great community Windermere Trails!!!! Build in 2014, original owner, 1,829d sqft, with a lot of upgrades. With 3 bedroom and 2 bat...

  • 3 Beds
  • 2.5 Baths
  • Windermere Trls Ph 1c SubDv.
  • 34786 Zip Code

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