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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

13238 Longacre Drive, Windermere image
13238 Longacre Drive, Windermere $688,000

Former Model Home. Home does not have a garage, it was built out as living space by the new homebuilder. 3280 sf, 4 bed, 3.5 bath, study, loft.

  • 4 Beds
  • 3.5 Baths
  • Windermere Terrace SubDv.
  • 34786 Zip Code
5327 Segari Way, Windermere image
5327 Segari Way, Windermere — 5327 $330,000

Cozy townhome. One floor. New Roof 2022, Corner home with lots of natural light. Eat-in kitchen, Real Wood Cabinets and Breakfast Bar. Split bedroom plan. French Doors le...

  • 2 Beds
  • 2 Baths
  • Summerport Ph 04 SubDv.
  • 34786 Zip Code
8409 Lake Burden Circle, Windermere image
8409 Lake Burden Circle, Windermere $1,549,000

This chic, recently renovated home maintains its timeless Mediterranean architecture and successfully evokes an appreciation for the past, while maintaining a mindset for...

  • 4 Beds
  • 4 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
14363 Red Cardinal Court, Windermere image
14363 Red Cardinal Court, Windermere $629,000

Perhaps thee primo lot in Summerport! This one is on the West Orange Country Club's Golf Course with land only on the west side of this ideal property! This Park Square d...

  • 4 Beds
  • 3 Baths
  • Summerport Ph 05 SubDv.
  • 34786 Zip Code
13013 Water Point Boulevard, Windermere image
13013 Water Point Boulevard, Windermere $2,740,000

Check out this gorgeous, well-priced property located in the wonderful town of Windermere! Just Minutes to the theme parks areas and Downtown Orlando. This luxurious 7-be...

  • 7 Beds
  • 6.5 Baths
  • Waterford Pointe Ph Ii Rep SubDv.
  • 34786 Zip Code
1560 Lake Rhea Drive, Windermere image
1560 Lake Rhea Drive, Windermere $1,200,000

Gorgeous home! Gated community. Fully renovated. The moment you enter the front door, you are greeted by bright open spaces and a picture window overlooking the private p...

  • 3 Beds
  • 4 Baths
  • Reserve At Belmere Ph 02 48 144 SubDv.
  • 34786 Zip Code
1238 Lake Whitney Drive, Windermere image
1238 Lake Whitney Drive, Windermere $2,500,000

Welcome to the exquisite and elegant Reserve At Belmere. A true luxury Tuscan style luxury home with spectacular views of Lake Whitney is being sold furnished. Step into ...

  • 4 Beds
  • 5.5 Baths
  • Reserve At Belmere Ph 02 48 144 SubDv.
  • 34786 Zip Code
8156 Boat Hook Loop Unit 306, Windermere image
8156 Boat Hook Loop Unit 306, Windermere — Na $349,000

Move in ready, three bedroom, two bathroom condo with elevator access, located within the gated community of Lakeside at Lakes of Windermere. This third floor unit featur...

  • 3 Beds
  • 2 Baths
  • Lakeside/Lks/Windermere SubDv.
  • 34786 Zip Code
11155 Coniston Way, Windermere image
11155 Coniston Way, Windermere $2,499,000

Lake Butler Sound, 24 hour gated/attended community - From the moment you enter through the stunning 12 ft arched glass and iron doors you will be impressed with this cus...

  • 5 Beds
  • 5.5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
9508 Windy Ridge Road, Windermere image
9508 Windy Ridge Road, Windermere $30,000,000

Perfectly positioned on 18 acres of meticulously manicured grounds, this walled and gated compound offers over 625 feet of picturesque and panoramic views on Lake Down of...

  • 7 Beds
  • 14.5 Baths
  • Acreage & Unrec SubDv.
  • 34786 Zip Code
9328 Westover Club Circle, Windermere image
9328 Westover Club Circle, Windermere $950,000

Welcome home. Beautiful fully renovated home that checks all your must haves and wants. The floor plan offers the ideal layout to embrace Florida living. Separate formal ...

  • 5 Beds
  • 3 Baths
  • Westover Club Ph 02 47/71 SubDv.
  • 34786 Zip Code
11948 Provincial Way, Windermere image
11948 Provincial Way, Windermere $2,250,000

You will fall in love with this absolutely beautiful Arthur Rutenberg, Calais model, estate home. Situated ideally on Lake Whitney with Covered Boat Dock, this home is re...

  • 4 Beds
  • 5 Baths
  • Reserve At Belmere Ph4 SubDv.
  • 34786 Zip Code
8047 Enchantment Drive Unit 1106, Windermere image
8047 Enchantment Drive Unit 1106, Windermere — 8047 $398,900

Beautiful newer Townhouse in Oasis Cove - Lakeside Village. Minutes from back side of Disney, and all the stores on SR 535. This 1647 Sq. Ft. 2 Story 2 Car Garage end uni...

  • 3 Beds
  • 2.5 Baths
  • Oasis Cove At Lakeside Village SubDv.
  • 34786 Zip Code
1455 Long Meadow Way, Windermere image
1455 Long Meadow Way, Windermere $769,995

Just Wonderful!! Windermere home in the exclusive, 24 Hour Guard Gated “RESERVE AT BELMERE” – A MUST SEE! Resort Style, Upscale Community! This elegant ONE FLOOR 4 bedro...

  • 5 Beds
  • 3 Baths
  • Reserve/Belmere Ph 04 SubDv.
  • 34786 Zip Code
1005 Down Reserve Court, Windermere image
1005 Down Reserve Court, Windermere $4,699,995

Under Construction. COME HOME TO A DREAM!! This Beautiful Modern Castle is being built in the lovely Lake Down Reserve neighborhood in Windermere, Florida. This home is d...

  • 6 Beds
  • 7.5 Baths
  • Rosser Reserve Rep SubDv.
  • 34786 Zip Code
13826 Summerport Trail Loop, Windermere image
13826 Summerport Trail Loop, Windermere $528,000

Welcome to this beautiful 4 bedroom / 2.5 bath Bungalow style home with open concept floor plan in the Summerport Trail community in Windermere, FL. As you enter this fan...

  • 4 Beds
  • 2.5 Baths
  • Summerport Trail SubDv.
  • 34786 Zip Code
13900 Darchance Road, Windermere image
13900 Darchance Road, Windermere $675,000

Popular Ashton Woods Ashbury model in the Enclave at Berkshire Park in Windermere. Great floor plan featuring 3 bedrooms, 3 bathrooms and a bonus room upstairs, totaling...

  • 4 Beds
  • 3 Baths
  • Enclave/Berkshire Park B G H I SubDv.
  • 34786 Zip Code
7490 Tattant Boulevard, Windermere image
7490 Tattant Boulevard, Windermere $675,000

Expect to be impressed with this 5BR estate-style home in the desirable Enclave at Berkshire Park in the Lake Sawyer South community. Room for everyone and everything, an...

  • 5 Beds
  • 3 Baths
  • Lake Sawyer South Ph 02 SubDv.
  • 34786 Zip Code
8052 Tibet Butler Drive, Windermere image
8052 Tibet Butler Drive, Windermere $1,748,000

Beautiful home located on 3rd fairway in the sought after guard gated Keenes Pointe community. This home has been completely updated with 6 bedrooms, 5 bathrooms, office,...

  • 6 Beds
  • 5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
8800 Crescendo Avenue, Windermere image
8800 Crescendo Avenue, Windermere $740,000

LOCATION, LOCATION, LOCATION...SOLAR POWERED HOME! This SPACIOUS home features 4bed with 2 FLEX SPACES (5th bed, office, den, etc) and 3.5 bath. Located in AMAZING Winder...

  • 4 Beds
  • 3.5 Baths
  • Windermere Trails SubDv.
  • 34786 Zip Code
13352 Bellaria Circle, Windermere image
13352 Bellaria Circle, Windermere $2,525,000

Located in the guard-gated neighborhood of Bellaria, this 5,524-square-foot Mediterranean estate is the perfect blend of design, architecture and luxury. Brilliantly and ...

  • 5 Beds
  • 5.5 Baths
  • Bellaria SubDv.
  • 34786 Zip Code
13124 Filly Ct, Windermere image
13124 Filly Ct, Windermere $1,450,000 ▼

Stunning semi rural pool home, nestled on 1.07 acres with idyllic views across 15 acres of community horse fields/stables. Fully renovated and lovingly maintained by its...

  • 5 Beds
  • 3 Baths
  • Farms SubDv.
  • 34786 Zip Code
9838 Laurel Valley Drive, Windermere image
9838 Laurel Valley Drive, Windermere $7,000,000

Majestic Lake Butler lakefront, Sunset views, Disney fireworks and the 15th hole of Isleworth's renowned championship golf course. As far as location goes, this home has ...

  • 5 Beds
  • 6.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
13136 Bellaria Circle, Windermere image
13136 Bellaria Circle, Windermere $2,285,000

Elegance and transitional modern style combine into a luxurious showplace of sophistication. This custom 5-bedroom estate home features a dramatic two-story entry foyer ...

  • 5 Beds
  • 5.5 Baths
  • Bellaria SubDv.
  • 34786 Zip Code
1727 Down Lake Drive, Windermere image
1727 Down Lake Drive, Windermere $1,095,000

One or more photo(s) has been virtually staged. Newly renovated home located on an acre in sought after Windermere with Chain of Lakes access. This one story 3261 square ...

  • 4 Beds
  • 2.5 Baths
  • Lakes SubDv.
  • 34786 Zip Code

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