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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

13939 Ancilla Boulevard, Windermere image
13939 Ancilla Boulevard, Windermere — 13900 $305,000

WELCOME HOME to this perfectly positioned townhome in the highly sought-after community of Summerport in Horizon West! This town home is surrounded by stunning bodies of ...

  • 3 Beds
  • 2 Baths
  • Summerport Phase 3 SubDv.
  • 34786 Zip Code
12218 Mckinnon Road, Windermere image
12218 Mckinnon Road, Windermere $1,100,000

Looking for a Lakefront Windermere home with the ability to customize it the way you want? This waterfront home under remodel and new construction is 50% complete and is...

  • 6 Beds
  • 6 Baths
  • N/A SubDv.
  • 34786 Zip Code
11442 Via Lucerna Circle, Windermere image
11442 Via Lucerna Circle, Windermere $630,000

This spectacular home is on a corner home site with brick paver driveway and exquisite stone elevation. Once inside, you are greeted by extensive hardwood floors in the l...

  • 6 Beds
  • 5 Baths
  • Belmere Village G-5 SubDv.
  • 34786 Zip Code
5819 Oxford Moor Boulevard, Windermere image
5819 Oxford Moor Boulevard, Windermere $970,000

Beautiful and well-maintained executive 5 BEDROOM, 4.5 BATH home located in the private GATED community of OXFORD MOOR in exclusive WINDERMERE! This home is full of immen...

  • 5 Beds
  • 4 Baths
  • Oxford Moor 47/30 SubDv.
  • 34786 Zip Code
11626 Claymont Cir, Windermere image
11626 Claymont Cir, Windermere $879,000

Keene's Pointe - highly desired gated/24-hour attended community in Windermere. This 4 bedroom/4 bath home has been meticulously maintained. Featuring formal living roo...

  • 4 Beds
  • 4 Baths
  • Keenes Pointe Ut 04 Sec 31 48 82 SubDv.
  • 34786 Zip Code
11133 Camden Park Drive, Windermere image
11133 Camden Park Drive, Windermere $1,927,000

Welcome to Golf Front luxury in this former custom builder's model home on the 2nd hole of the Golden Bear Club golf course in the 24-hour attended Windermere community o...

  • 5 Beds
  • 4 Baths
  • Keenes Pointe Ut 05 50 93 SubDv.
  • 34786 Zip Code
9320 Woodbreeze Boulevard, Windermere image
9320 Woodbreeze Boulevard, Windermere $460,000

One or more photo(s) has been virtually staged. This Windermere one-story home offers granite countertops, and a two-car garage.

  • 4 Beds
  • 2 Baths
  • Silver Woods Ph 03 SubDv.
  • 34786 Zip Code
13742 Amelia Pond Drive, Windermere image
13742 Amelia Pond Drive, Windermere $589,900

Welcome to this gorgeous home on an oversized lot in the very desirable community of Summerport with incredible amenities! As you enter, you will be wowed by the soaring...

  • 4 Beds
  • 2 Baths
  • Summerport Ph I SubDv.
  • 34786 Zip Code
9520 Windy Ridge Road, Windermere image
9520 Windy Ridge Road, Windermere $5,995,000

EXCEPTIONAL PROPERTY Over 6 acres on Lake Down - on the coveted Butler Chain of Lakes. The size and uniquely high elevation of this coveted address with southern exposure...

  • 34786 Zip Code
9401 Palm Tree Drive, Windermere image
9401 Palm Tree Drive, Windermere $395,000

When they say location is everything..Location, Location,Location! This wonderful Windermere home ,with top rated orange county schools. Home sits backing up to Isleworth...

  • 3 Beds
  • 2 Baths
  • Silver Woods Ph 03 SubDv.
  • 34786 Zip Code
6537 Helmsley Circle, Windermere image
6537 Helmsley Circle, Windermere $485,000

One or more photo(s) has been virtually staged. BEAUTIFUL home in a highly DESIRABLE area - Preston Square of Horizon West in Windermere. Home and Neighborhood are absolu...

  • 5 Beds
  • 3 Baths
  • Preston Square SubDv.
  • 34786 Zip Code
5409 Gemgold Court, Windermere image
5409 Gemgold Court, Windermere $550,000

Absolutely Beautiful Pool Home in the Highly Desirable Community of Summerport in Windermere. This home sits on an OVERSIZED lot in a cul-de-sac, Enjoy the Stunning Water...

  • 5 Beds
  • 3 Baths
  • Eden's Hammock SubDv.
  • 34786 Zip Code
9341 Westover Club Circle, Windermere image
9341 Westover Club Circle, Windermere $575,000

*WESTOVER CLUB* Wonderful Windermere Home sitting on a .33 acre lot that does not back up to another home, No Rear Neighbors. Featuring 4 bedrooms and 3 full bathrooms, a...

  • 4 Beds
  • 3 Baths
  • Westover Club Ph 02 47/71 SubDv.
  • 34786 Zip Code
6602 Bridgewater Village Road, Windermere image
6602 Bridgewater Village Road, Windermere $560,000 ▲

Welcome home! Beautiful two-story, Windermere home. This is a 5 bedroom, 3 bathroom, 2 car garage home. The outdoor kitchen will make your home the life of the party and...

  • 5 Beds
  • 3 Baths
  • Vineyards/Horizons West Ph 1b SubDv.
  • 34786 Zip Code
8441 Lake Burden Cir, Windermere image
8441 Lake Burden Cir, Windermere $1,684,900

Keene's Pointe 24-hour/gated attended community featuring The Golden Bear Club. Gorgeous custom built pool home in Keene's Pointe!!!! This home has it all with 6 BEDROOM...

  • 6 Beds
  • 5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
9370 Palm Tree Drive, Windermere image
9370 Palm Tree Drive, Windermere $465,000

One or more photo(s) has been virtually staged. Location, location, location. Welcome to this gorgeous Windermere pool home, completely updated and truly move-in ready. L...

  • 4 Beds
  • 2 Baths
  • Silver Woods Ph 03 SubDv.
  • 34786 Zip Code
4863 Flint Road, Windermere image
4863 Flint Road, Windermere $538,995 ▼

Beautiful 5 bedroom 3 bath home with oversized bonus room in Summerport community walking or short bike ride to 3 A rated schools. Inside professionally painted last wee...

  • 5 Beds
  • 3 Baths
  • Summerport Ph 05 SubDv.
  • 34786 Zip Code
3026 Porto Lago Court, Windermere image
3026 Porto Lago Court, Windermere $3,369,000

Almost 9000 heated square feet of SUPERIOR LIVING ON THE BUTLER CHAIN! Located within the private and gated community of Marbella, this exquisite custom windermere pool...

  • 6 Beds
  • 7 Baths
  • Lake Down Pointe 50 42 SubDv.
  • 34786 Zip Code
11532 Waterstone Loop Drive, Windermere image
11532 Waterstone Loop Drive, Windermere $1,599,000

Stunning and immaculately maintained Silliman home on the best street within desirable Waterstone Community. This all one floor home is like brand new and never lived in...

  • 4 Beds
  • 4 Baths
  • Waterstone SubDv.
  • 34786 Zip Code
0000 Reserve Windermere Court, Windermere image
0000 Reserve Windermere Court, Windermere $515,000

Welcome to The Reserve at Windemere, Windermere's newest custom home neighborhood. This quaint community offers only 8 homesites in an A+ school district in Windermere. ...

  • Reserve At Windermere SubDv.
  • 34786 Zip Code
13736 Amelia Pond Drive, Windermere image
13736 Amelia Pond Drive, Windermere $650,000

Welcome to your dream oasis! From the moment you see this home you’ll fall in love with it’s lush mature landscaping and brick paver driveway. Upon entering the home, yo...

  • 4 Beds
  • 3 Baths
  • Summerport SubDv.
  • 34786 Zip Code
5356 Water Creek Drive, Windermere image
5356 Water Creek Drive, Windermere $600,000 ▲

Here is your opportunity to purchase vacant land and build your dream home in the Lake Davis Estates Community. Enjoy luxury living at it’s finest Conveniently located ...

  • Lake Davis Estates SubDv.
  • 34786 Zip Code
6037 Caymus Loop, Windermere image
6037 Caymus Loop, Windermere $777,000

Situated on a spacious, maturely landscaped lot overlooking the 14th fairway of The Golden Bear Club is the perfect Key West style family or vacation home for your buyer!...

  • 3 Beds
  • 2 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
9095 Reflection Pointe Drive, Windermere image
9095 Reflection Pointe Drive, Windermere $570,000

Take advance of this incredible single family residence in Windermere, close to many shops, groceries, attractions and many more. This home features an open flor plan in ...

  • 4 Beds
  • 3 Baths
  • Windermere Trls Ph 5b SubDv.
  • 34786 Zip Code
2634 Tryon Place, Windermere image
2634 Tryon Place, Windermere $799,900

Beautiful home on over 1/2 acre, wonderfully-landscaped. Single story, no stairs to climb. Spacious and open floor plan. Tropical screened pool with covered seating ar...

  • 4 Beds
  • 3 Baths
  • Manors At Butler Bay SubDv.
  • 34786 Zip Code

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