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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

11409 N Camden Commons Drive, Windermere image
11409 N Camden Commons Drive, Windermere $1,100,000

Don't miss out on this home inside the exclusive guard gated community of Keens Pointe and home to the Golden Bear Country Club featuring Jack Nicklaus golf course. This ...

  • 4 Beds
  • 4.5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
411 E 6th Avenue, Windermere image
411 E 6th Avenue, Windermere $899,900

Beautifully updated home in the heart of downtown Windermere on a spacious homesite just a short stroll to Main Street. Nestled among majestic oaks and down a long pavere...

  • 4 Beds
  • 3 Baths
  • Windermere Rep SubDv.
  • 34786 Zip Code
12842 Jacob Grace Court, Windermere image
12842 Jacob Grace Court, Windermere $1,388,800

Custom Video www.12842jacobgrace.site/mls FIRST TIME EVER OFFERED FOR SALE, original owner and very first lot ever sold in Tildens Grove ! Pride of ownership is self e...

  • 5 Beds
  • 3.5 Baths
  • Tildens Grove Ph 01 47/65 SubDv.
  • 34786 Zip Code
1825 Windermeredown Place, Windermere image
1825 Windermeredown Place, Windermere $1,295,000

One or more photo(s) has been virtually staged. Gorgeous Executive Estate on over an acre is SUPER SPACIOUS with versatile floor plan where rooms can be repurposed as you...

  • 6 Beds
  • 4.5 Baths
  • Windermere Downs Ph 03 SubDv.
  • 34786 Zip Code
13534 Bramham Lane, Windermere image
13534 Bramham Lane, Windermere $469,900

* Multiple offers received, Seller has requested Highest and/or Best by 2:00 PM Monday April 4, 2023 * Attention Disney Lovers! On a quiet tree lined street approximatel...

  • 3 Beds
  • 2 Baths
  • Lakes/Windermere-Peachtree SubDv.
  • 34786 Zip Code
11486 Misty Oak Alley, Windermere image
11486 Misty Oak Alley, Windermere $499,900

Beautiful single family home with 3 bedrooms and 2 1/2 baths located in the Ashlin Park Community in Windermere. The kitchen is upgraded with stainless steel appliances....

  • 3 Beds
  • 2.5 Baths
  • Ashlin Park Ph 1 SubDv.
  • 34786 Zip Code
11644 Ashlin Park Boulevard, Windermere image
11644 Ashlin Park Boulevard, Windermere $600,000

This lovely two-story home found in desirable Ashlin Park offers the convenience of a premium location to A- rated schools in Windermere. This home features exquisite upg...

  • 4 Beds
  • 2.5 Baths
  • Ashlin Park Ph 1 SubDv.
  • 34786 Zip Code
12264 Montalcino Circle, Windermere image
12264 Montalcino Circle, Windermere $6,295,000

A masterpiece of artful design nestled in Windermere, Florida, this one-of-a kind, Lake Burden home immediately transports you to a level of world-class beauty, serenity...

  • 4 Beds
  • 4.5 Baths
  • Casa Del Lago Rep SubDv.
  • 34786 Zip Code
12224 Mckinnon Road, Windermere image
12224 Mckinnon Road, Windermere $1,799,000

One acre of Windermere lakefront living, with no HOA! This home is situated on Lake Crescent, which is crystal clear and the largest private lake in Windermere. When the ...

  • 4 Beds
  • 4.5 Baths
  • Butler Bay SubDv.
  • 34786 Zip Code
12846 Langstaff Drive, Windermere image
12846 Langstaff Drive, Windermere — Lake Reams Townhomes $365,000

Rare Lake Reams Townhome in Windermere, Fl. 1380 sq ft, 2 bedroom, 2.5 bath Home on Beautiful Mature Oak Tree Lined Street. 2 Car Garage with Courtyard in between. Ne...

  • 2 Beds
  • 2.5 Baths
  • Lakes/Windermere-Lk Reams Twnh SubDv.
  • 34786 Zip Code
12856 Strode Lane, Windermere image
12856 Strode Lane, Windermere — Lot 244 $430,000

Two story town home in excellent condition and newly painted inside! The kitchen features wood cabinets, granite counter tops, backsplash and a large island. The lighting...

  • 3 Beds
  • 2.5 Baths
  • Windermere Sound Ph 2 SubDv.
  • 34786 Zip Code
9725 Chestnut Ridge Drive, Windermere image
9725 Chestnut Ridge Drive, Windermere $4,399,000

This home features 6885 square feet of AC living space and 11,000 square feet under roof! The home is situated inside Isleworth, a gated community with 24 hour security b...

  • 5 Beds
  • 6 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
5507 Worsham Ct, Windermere image
5507 Worsham Ct, Windermere $5,950,000

This stunning custom estate overlooks the fourteenth green on Isleworth Golf and Country Club, one of the world’s most prestigious private golf club communities. As you c...

  • 5 Beds
  • 5.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9247 Legado Drive, Windermere image
9247 Legado Drive, Windermere — Mattamy Homes $820,000

Luxury first rental property in Windermere with excellent schools. The property is located in the best and largest lot of the condominium and with a privileged view of th...

  • 4 Beds
  • 2.5 Baths
  • Legado SubDv.
  • 34786 Zip Code
1810 Westover Reserve Boulevard, Windermere image
1810 Westover Reserve Boulevard, Windermere $999,000

Rare opportunity to own a home in the sought-after gated community of Westover Reserve in the heart of Windermere! An enclave of only 81 homes, this community offers imma...

  • 4 Beds
  • 5 Baths
  • Westover Reserve Ph 01 SubDv.
  • 34786 Zip Code
11545 Brickyard Pond Lane, Windermere image
11545 Brickyard Pond Lane, Windermere $1,699,765

Magnificent Lakefront home set on a calm cul-de-sac! This spectacular residence treats you to ample privacy, space, and comfort in Windermere. Occupying an oversized 3/4-...

  • 6 Beds
  • 6.5 Baths
  • Lake Burden South Ph I SubDv.
  • 34786 Zip Code
12525 Montalcino Circle, Windermere image
12525 Montalcino Circle, Windermere $989,000

ENOUGH LOOKING!! CHECK OUT this Gorgeous POOL home located in the Exclusive GATED Community Casa Del Lago in Windermere. This home has a lovely **courtyard feature** at t...

  • 4 Beds
  • 3.5 Baths
  • Casa Del Lago Rep SubDv.
  • 34786 Zip Code
8057 Tibet Butler Drive, Windermere image
8057 Tibet Butler Drive, Windermere $1,695,000

THIS HOME IS THE ENTERTAINERS DREAM HOME! Located in the best community of Central Florida, it has a guard gated, golf, tennis and lakefront country club with a Signatur...

  • 4 Beds
  • 4 Baths
  • Keenes Pointe Unit 2 SubDv.
  • 34786 Zip Code
11444 Misty Oak Alley, Windermere image
11444 Misty Oak Alley, Windermere $599,990 ▼

Don’t miss out on this absolutely remarkable, MOVE-IN ready home which will accommodate any family's needs. Upon entering the home you are greeted with many upgrades: hig...

  • 4 Beds
  • 2.5 Baths
  • Ashlin Park Ph 1 SubDv.
  • 34786 Zip Code
11952 Camden Park Drive, Windermere image
11952 Camden Park Drive, Windermere $1,690,000

Welcome to your own private oasis in one of the largest lots at Keene’s Pointe! With plenty of space, both indoor and outdoor, a formal living and dining room, a kitchen ...

  • 5 Beds
  • 4 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
11129 Lake Butler Boulevard, Windermere image
11129 Lake Butler Boulevard, Windermere $849,000 ▲

Rare Opportunity to own 1 of the last affordable move in ready homes in Downtown Windermere - Recent sales of new homes are over $2.0 on this street - The Lot is 100 feet...

  • 3 Beds
  • 2 Baths
  • Wauseon Ridge SubDv.
  • 34786 Zip Code
9306 Blanche Cove Drive, Windermere image
9306 Blanche Cove Drive, Windermere $17,500,000

Sophisticated elegance masterfully packaged into a custom-crafted lakefront mansion built specifically for the ultimate sports enthusiast, situated behind the secured man...

  • 5 Beds
  • 6.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
11237 Camden Park Drive, Windermere image
11237 Camden Park Drive, Windermere $1,200,000

Welcome to your dream home located in the desirable Keene's Pointe community! This updated and upgraded 4 bedroom, 4 bath pool home boasts 3,492 square feet of luxurious ...

  • 4 Beds
  • 4 Baths
  • Keenes Pointe Unit 7 SubDv.
  • 34786 Zip Code
5139 Isleworth Country Club Dr, Windermere image
5139 Isleworth Country Club Dr, Windermere $7,500,000

With a fabulous location along the front nine of Isleworth’s renowned championship golf course overlooking Hole 3, this expansive estate showcases just under 14,000 squar...

  • 7 Beds
  • 7.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
10430 Birch Tree Lane, Windermere image
10430 Birch Tree Lane, Windermere $1,475,000

Now is your opportunity to own a luxurious estate home in the highly sought after Windermere Downs neighborhood! This 6 bedroom, 4.5 bath Brierhill custom-built home sits...

  • 6 Beds
  • 4.5 Baths
  • Windermere Downs Ph 03 SubDv.
  • 34786 Zip Code

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