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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

11421 Arborside Bend Way, Windermere image

11421 Arborside Bend Way, Windermere $340,100

Awesome opportunity to own this 4 bedroom 3 bath home plus office in Windermere!! This home is located in the gated neighborhood of Glenmuir, minutes away from downtown W...

4 Beds
3 Baths
Glenmuir 48 39 SubDv.
34786 Zip Code

5559 Remsen Cay Lane, Windermere $369,900

Welcome to this move-in-ready 4 bedroom, 3 bathroom single-family home located in the wonderful community of Edens Hammock in Windermere. This home features a formal livi...

4 Beds
3 Baths
Eden's Hammock SubDv.
34786 Zip Code

3992 Isabella Circle, Windermere $1,720,000

Stunning home located in Casabella, a luxury gated community. This 5 bedroom and 4/1 bath home is located on a .05 acres lot. As you enter the home you are greeted by a f...

5 Beds
4.5 Baths
Casabella Ph 2 SubDv.
34786 Zip Code

12246 Montalcino Circle, Windermere image

12246 Montalcino Circle, Windermere $2,390,000

For the connoisseur of life, an ideal home is in perfect harmony with its surroundings. So true for this beautiful West Indies inspired custom home, Castellina. The home ...

4 Beds
4.5 Baths
Casa Del Lago Rep SubDv.
34786 Zip Code

11548 Ashlin Park Boulevard, Windermere image

11548 Ashlin Park Boulevard, Windermere $434,900

Why wait for a new build when you can move into this stunning very well maintained 2 story 3 bed 2.5 bath home in the upscale community of Ashlin Park located in the soug...

3 Beds
2.5 Baths
Ashlin Park Ph 1 SubDv.
34786 Zip Code

11103 Bridge House Road, Windermere image

11103 Bridge House Road, Windermere $3,999,900

Located in the 24-hour guard gated neighborhood of Lake Butler Sound, this impressive estate is brilliantly designed to deliver the perfect balance between architecture, ...

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

6138 S Hampshire Court, Windermere image

6138 S Hampshire Court, Windermere $900,000

Short Sale. This wonderful golf front home sits on the highly desirable street of South Hampshire within the renowned community of Keene's Pointe. At just under 4,900 s...

4 Beds
3.5 Baths
Keene's Pointe SubDv.
34786 Zip Code

611 Magnolia Street, Windermere $676,000

Amazing Opportunity! Everyone must see this custom built Akers home with endless features. 2 story / split plan with 5 bedrooms, 3.5 Baths - screened pool with heated spa...

5 Beds
3.5 Baths
Windermere Town SubDv.
34786 Zip Code

6625 Duncaster Street, Windermere $388,000

Don't let this one slip away!!! Welcome to your new home in the beautiful Lakes of Windermere community. At your new abode, you can retreat to your spacious 4 Bedroom + l...

4 Beds
3 Baths
Lakes/Windermere Ph 02a SubDv.
34786 Zip Code

11807 Vermillion Avenue, Windermere image

11807 Vermillion Avenue, Windermere $310,000

Like brand new! This end unit townhouse has all the perks! The 3 bedroom 2.5 bathroom 2 car garage is waiting for you! Enter into the open floor living room with tile t...

3 Beds
2.5 Baths
Windermere Trls Prcl 3 SubDv.
34786 Zip Code

12436 Summerport Beach Way, Windermere image

12436 Summerport Beach Way, Windermere $1,150,000

One lucky buyer will truly embrace lake life and have access to the famed Windermere Chain of Lakes in their own back yard. With 180 degree views of the best lake on the ...

3 Beds
2 Baths
Summerport Beach SubDv.
34786 Zip Code

12675 Hawkstone Drive, Windermere $984,900

Gorgeous 4 bed 4 bath lakefront home in the heart of Windermere! Enjoy breathtaking views of Lake Sawyer! New hardwood flooring and stone throughout. Gourmet kitchen with...

4 Beds
4 Baths
Lakes Windermere Ph 01 49 108 SubDv.
34786 Zip Code

11060 Ullswater Lane Unit 2, Windermere image

11060 Ullswater Lane Unit 2, Windermere $490,000

We are proud to offer this gorgeous oversized homesite (.83 acres) as the perfect location for your dream custom home! This prestigious homesite is very unique because it...

Reserve At Lake Butler Sound SubDv.
34786 Zip Code

11557 Waterstone Loop Drive, Windermere image

11557 Waterstone Loop Drive, Windermere $2,290,000

Stunning contemporary custom home. This amazing home with a luxury view to Cypress lake. Lakefront home with breathtaking view of the lake and woods from almost every roo...

5 Beds
5.5 Baths
Waterstone SubDv.
34786 Zip Code

11804 Silverlake Park Drive, Windermere image

11804 Silverlake Park Drive, Windermere $345,000

Front Porch Living in this beautiful 4 bedroom, 2 1/2 bath Windermere Trails Home. This 2-story home is situated on an oversized corner lot. As you enter the house there ...

4 Beds
2.5 Baths
Windermere Trls SubDv.
34786 Zip Code

8176 Jailene Drive, Windermere $495,000

Beautiful Home located in Berkshire park, Windermere !!! With 3,454 SqFt living space ,4 bedroom 3.5 bath home offers you all the comfort and luxury you are looking for...

4 Beds
3.5 Baths
Lake Sawyer South Ph 5 SubDv.
34786 Zip Code

1433 Whitney Isles Drive, Windermere image

1433 Whitney Isles Drive, Windermere $499,000

This fantastic pool home has just had a full make over - full exterior paint including 2 garage blocks, interior has new paint and carpets throughout so ready for new own...

4 Beds
3.5 Baths
Whitney Isles/Belmere Ph 02 SubDv.
34786 Zip Code

502 Jennifer Lane, Windermere $2,900,000

Undoubtedly & unequivocally one of the most unique estate homes on the Butler Chain of Lakes! This 4-story dream home was designed and built by the present owners who wer...

6 Beds
7.5 Baths
Windermere Oaks SubDv.
34786 Zip Code

11521 Camden Park Drive Unit 1, Windermere image

11521 Camden Park Drive Unit 1, Windermere $695,000

Beautiful 5 bedroom 5 bath two story house immediately available in guard gated Keenes Pointe golf community! Highly sought after Camden Village section of Keenes Pointe ...

5 Beds
4.5 Baths
Keenes Pointe Unit 8 SubDv.
34786 Zip Code

5025 Latrobe Drive, Windermere $1,750,000

Nestled within the main gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers a fabulous location along the front nine. An impres...

4 Beds
5.5 Baths
Isleworth SubDv.
34786 Zip Code

9921 Brentford Court Unit 1, Windermere image

9921 Brentford Court Unit 1, Windermere $969,000

Look no further. Take this opportunity to live in Keenes Pointe, home of the Golden Bear Club 18 hole Jack Nicklaus designed course featuring golf, tennis, fitness, swimm...

6 Beds
5.5 Baths
Keenes Pointe SubDv.
34786 Zip Code

13826 Eden Isle Boulevard, Windermere image

13826 Eden Isle Boulevard, Windermere $375,000

Short Sale. Come see a well designed spacious Craftsman home located in the well sought after community of Eden Isle. This 4 bed 3 ½ half bath has lots of room for ente...

4 Beds
3.5 Baths
West Point Commons SubDv.
34786 Zip Code

12624 Park Avenue, Windermere $1,849,900

Make this picture-perfect sunrise yours!! This home site is one of the last remaining in Chaine Du Lac a gated custom home neighborhood. This lot sits on perfectly on a r...

Chaine Du Lac SubDv.
34786 Zip Code

5119 Tildens Grove Boulevard, Windermere image

5119 Tildens Grove Boulevard, Windermere $798,880

BEST deal in Tildens Grove, fully renovated 4-BR (3 oversized), 4.5 bath (all renovated) POOL home (with new 2-story screen enclosure) on private .62-acre conservation lo...

4 Beds
4.5 Baths
Tildens Grove Ph 01 47/65 SubDv.
34786 Zip Code

9732 Carillon Park Drive, Windermere image

9732 Carillon Park Drive, Windermere $1,595,000

1.37 ACRE LAKEFRONT LOT WITH ACCESS TO THE BUTLER CHAIN. This MAGNIFICENT WATERFRONT LOT IS POSITIONED IN THE SPECTACULAR VILLAGE OF GROSVENOR POINTE IN KEENE'S POINTE. ...

Keene's Pointe SubDv.
34786 Zip Code

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