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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

2608 Midsummer Drive, Windermere image
2608 Midsummer Drive, Windermere $2,395,000

PRIME LOCATION. TWO ACRE lot with almost 200 ft of shoreline. High elevation affords stunning, panoramic LAKE views and FIREWORK displays. On the East side of the BUTLER ...

  • Lake Down Shores Rep SubDv.
  • 34786 Zip Code
8427 Vivaro Isle Way, Windermere image
8427 Vivaro Isle Way, Windermere $514,990

READY NOW! This Energy Star Certified home has 4-bedrooms, 3-baths, loft, extended covered lanai and 2-car garage on a homesite with no rear neighbors that backs to beaut...

  • 4 Beds
  • 3 Baths
  • Windermere Isle SubDv.
  • 34786 Zip Code
10809 Bayshore Drive, Windermere image
10809 Bayshore Drive, Windermere $1,895,000

EXQUISITE LAKEFRONT LOCATION! This exclusive home is situated on 3.46 acres with 288 feet of lake frontage on beautiful Lake Down. In addition to the vast lake frontage,...

  • 5 Beds
  • 5.5 Baths
  • Bayshore Estates SubDv.
  • 34786 Zip Code
9206 Reflection Pointe Drive, Windermere image
9206 Reflection Pointe Drive, Windermere $425,000

From the time you enter this light bright home, you will appreciate the contemporary lifestyle it offers. Built in 2016, the great room is all tile, with tall ceilings an...

  • 4 Beds
  • 3 Baths
  • Windermere Trls Ph 4a SubDv.
  • 34786 Zip Code
5181 Latrobe Drive, Windermere image
5181 Latrobe Drive, Windermere $1,395,000

Set behind the manned gates of Central Florida’s most exclusive neighborhood and on the 4th hole of the Isleworth Golf Course, this executive pool home offers peace and p...

  • 4 Beds
  • 3.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
Windermere image
Windermere $345,000

Windermere home built by Ashton Woods. Great location, no rear neighbors!!! New exterior paint. Two-story home, welcoming front porch. Enter the foyer to living room, din...

  • 3 Beds
  • 2.5 Baths
  • 34786 Zip Code
620 Ridgewood Drive, Windermere image
620 Ridgewood Drive, Windermere $875,000

Custom renovation blends modern and craftsman style in the Town of Windermere. Lake views from the welcoming front porch that also serves as a gathering place. This home...

  • 3 Beds
  • 2.5 Baths
  • Windermere Town Rep SubDv.
  • 34786 Zip Code
2617 Carter Grove Circle, Windermere image
2617 Carter Grove Circle, Windermere $695,000

OPPORTUNITY TO LIVE IN THE QUAINT TOWN OF WINDERMERE in pristine The Manors at Butler Bay! Beautiful traditional & elegant 5 bedroom, 3.5 bath home located on an acre is ...

  • 5 Beds
  • 3.5 Baths
  • Manors At Butler Bay Ph 01 SubDv.
  • 34786 Zip Code
5120 Isleworth Country Club Drive, Windermere image
5120 Isleworth Country Club Drive, Windermere $3,600,000

This modern estate, featuring five bedrooms and six full and one half baths, rests on an acre overlooking the seventh fairway of Isleworth’s championship golf course and...

  • 5 Beds
  • 6.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
Ridgewood Drive, Windermere image
Ridgewood Drive, Windermere $450,000

BUTLER CHAIN BOATHOUSE FOR SALE. Enjoy lakefront living without moving and high taxes!! This gorgeous park setting is a tranquil get away and offers a recreational pla...

  • 34786 Zip Code
5114 Fairway Oaks Drive, Windermere image
5114 Fairway Oaks Drive, Windermere $995,900

Welcome to the gated , manned and luxury community of ISLEWORTH, which offers lake access and premier golfing and more. This is a great opportunity to own this two story ...

  • 7 Beds
  • 7 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
13025 Garridan Avenue, Windermere image
13025 Garridan Avenue, Windermere $384,900

This MOVE-IN READY HOME beautiful 4 bedroom, 3.5 bath home in the desirable community of Windermere Sound! This warm and welcoming home was built in 2015 and features an ...

  • 4 Beds
  • 3.5 Baths
  • Windermere Sound Ph 2 SubDv.
  • 34786 Zip Code
6630 Duncaster Street, Windermere image
6630 Duncaster Street, Windermere $509,900

VIRTUAL TOUR/FLOOR PLAN WITH MEASUREMENTS BOTH AVAILABLE**RENOVATED LAKES OF WINDERMERE HOME** This immaculate 2 story home features 5 spacious bedrooms, 4 full bathrooms...

  • 5 Beds
  • 5 Baths
  • Lakes/Windermere Ph 02a SubDv.
  • 34786 Zip Code
4613 Indian Deer Road, Windermere image
4613 Indian Deer Road, Windermere $474,900

This beautiful 4 bed - 4 bath home is in excellent condition and is located in desirable Summerport neighborhood. Incredible neighborhood with tree lined streets, walkwa...

  • 4 Beds
  • 4 Baths
  • Summerport Ph 05 SubDv.
  • 34786 Zip Code
9304 Isleworth Gardens Drive, Windermere image
9304 Isleworth Gardens Drive, Windermere $1,895,000

Stately elegance and exceptional craftsmanship define luxury living from inside this graceful waterfront villa with 3-bedroom suites, Executive office, and private movie ...

  • 3 Beds
  • 3.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
6298 Golden Dewdrop Trail, Windermere image
6298 Golden Dewdrop Trail, Windermere $309,000

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

  • 3 Beds
  • 2.5 Baths
  • Windermere Lndgs Ph 02 SubDv.
  • 34786 Zip Code
11566 Ashlin Park Boulevard, Windermere image
11566 Ashlin Park Boulevard, Windermere $375,000

Tour the home you have been dreaming about! This beautiful Two Story - 3 bedroom 2.5 bathroom Single Family Home with detached Two Car Garage offers an amazing open floor...

  • 3 Beds
  • 2.5 Baths
  • Ashlin Park Ph 1 SubDv.
  • 34786 Zip Code
6885 Northwich Drive, Windermere image
6885 Northwich Drive, Windermere $410,000

This amazing, 5-bedroom home has been IMPECCABLY MAINTAINED by the original owners. You have just over 3,000 sq ft ideally located in one of the most sought-after neighbo...

  • 5 Beds
  • 2.5 Baths
  • Lakes Windermere Ph 01 49 108 SubDv.
  • 34786 Zip Code
13813 Orange Crest Drive, Windermere image
13813 Orange Crest Drive, Windermere $329,988

This is your perfect Windermere home! This charming property has curb appeal for days! As you enter, the cozy front porch welcomes you into this quaint and beautifully up...

  • 4 Beds
  • 2 Baths
  • Eden Isle SubDv.
  • 34786 Zip Code
8436 Lake Burden Cir, Windermere image
8436 Lake Burden Cir, Windermere $839,000

Keene's Pointe - 24-hour gated/attended community. This home offers 5 bedrooms and 5 1/2 baths, formal living and dining rooms and an optional bonus/hobby/storage room. T...

  • 5 Beds
  • 5.5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
5323 W Lake Butler Road, Windermere image
5323 W Lake Butler Road, Windermere $800,000

LAKEFRONT HOME…. located directly on Lake Butler of the famed Butler Chain of Lakes! The chain has over 5000 acres of water distributed in 13 interconnected lakes & is d...

  • Summerport Beach SubDv.
  • 34786 Zip Code
11824 Camden Park Drive, Windermere image
11824 Camden Park Drive, Windermere $619,000

The house, recently painted is located in a cul-de-sac quite street with matured landscaping and full grown Oak trees and Magnolia trees, setting a desirable environment ...

  • 4 Beds
  • 3 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
11650 Vicolo Loop, Windermere image
11650 Vicolo Loop, Windermere $498,000

Beautiful home in the Gated Community of Belmere, in Windermere. with 4 Bedroom, 3 Bath with a huge Family Room. Split Bedroom Configuration with In-Law Bedroom Bathroom ...

  • 4 Beds
  • 3 Baths
  • Belmere Village G4 50 58 SubDv.
  • 34786 Zip Code
6061 Caymus Loop, Windermere image
6061 Caymus Loop, Windermere $695,000

Beautiful, fully Remodeled, 4BR/4.5 Bath Charleston Row House with gorgeous open pool situated on the 14th fairway of the Jack Nicklaus Signature Golf Course in Keene’s P...

  • 4 Beds
  • 4.5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
6126 Kirkstone Lane, Windermere image
6126 Kirkstone Lane, Windermere $4,999,995

Perfectly sited along the shores of the coveted Lake Butler, this exquisite home has amazing sunsets in the 24 hour guard gated community of The Reserve at Lake Butler So...

  • 5 Beds
  • 6.5 Baths
  • Reserve At Lake Butler Sound 45/120 SubDv.
  • 34786 Zip Code

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