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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

5344 Water Creek Drive, Windermere image
5344 Water Creek Drive, Windermere $849,000

IMMEDIATE OCCUPANCY AVAILABLE! Lake Front View CUSTOM BUILT HOME. Entertainers dream overlooking spacious enclosed lanai/pool deck, Oversized 8ft deep pool you can swim l...

  • 5 Beds
  • 4 Baths
  • Lake Davis Estates SubDv.
  • 34786 Zip Code
14248 Confetti Drive, Windermere image
14248 Confetti Drive, Windermere — 14248 $305,000

One of a Kind in the heart of Windermere! Come view this large Townhome with an additional guest house/mother in law suite with private entrance. 2 properties for the pri...

  • 4 Beds
  • 3.5 Baths
  • Summerport Ph 04 C E F & G SubDv.
  • 34786 Zip Code
8447 Woburn Court, Windermere image
8447 Woburn Court, Windermere $600,000

This beautiful home BACKS to TIBET BUTLER PRESERVE affording privacy and natural beauty. Truly gracious Southern living is yours in the beautiful 24 hour guard gated comm...

  • 4 Beds
  • 3 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
13094 Overstreet Road, Windermere image
13094 Overstreet Road, Windermere $339,900

DOUBLE MASTER | LOW HOAs THAT INCLUDE LAWN MAINTENANCE | RESORT STYLE AMMENITIES!!! This two-story home is tucked away in the luxury of the Windermere Sound Subdivision. ...

  • 4 Beds
  • 3.5 Baths
  • Windermere Sound SubDv.
  • 34786 Zip Code
3702 Lake Buynak Road, Windermere image
3702 Lake Buynak Road, Windermere $450,000

One or more photo(s) has been virtually staged. WOW...Lakefront on Lake Buynak in Windermere and 1.8 acres with mature oaks and magnolias for only $450,000!!! You will ha...

  • 4 Beds
  • 2 Baths
  • Lake Buynak Estates SubDv.
  • 34786 Zip Code
13737 Calera Alley, Windermere image
13737 Calera Alley, Windermere — 13737 $313,500

Windermere living at its best! Immaculate 3 Bedroom 2.5 Bath modern townhome located in the charming area of Windermere! Shows like a model! This home features: upgrade k...

  • 3 Beds
  • 2.5 Baths
  • Vineyards/Horizons West Ph 2b SubDv.
  • 34786 Zip Code
13770 Bressler Aly, Windermere image
13770 Bressler Aly, Windermere — 0121 $319,999

Enjoy a low maintenance lifestyle conveniently located in Windermere with this two-story wonderfully upgraded end unit townhome that is less than two years new. This hom...

  • 4 Beds
  • 2.5 Baths
  • Vineyards Of Horizons West SubDv.
  • 34786 Zip Code
1922 Hempel Avenue, Windermere image
1922 Hempel Avenue, Windermere $699,900

This 2-story French Country home sits on a PRIVATE 1+ ACRE ESTATE. You must experience to appreciate! NO HOA. Deep setback from road, powered GATE ENTRANCE & NEWLY PAV...

  • 5 Beds
  • 3.5 Baths
  • Gotha Town SubDv.
  • 34786 Zip Code
5005 W Lake Butler Rd, Windermere image
5005 W Lake Butler Rd, Windermere $2,325,000

GORGEOUS ESTATE LOT ON LAKE BUTLER! Nearly 2 acres of level, cleared land with a covered boat dock and lift. This privately gated property features century-old oak trees ...

  • Un-Incorporated SubDv.
  • 34786 Zip Code
5005 W Lake Butler Rd, Windermere image
5005 W Lake Butler Rd, Windermere $2,325,000

Old Florida living with modern luxuries! With nearly 2 acres on Lake Butler, this beautifully renovated mid-century home features unmatched panoramic lake views. This pri...

  • 3 Beds
  • 3 Baths
  • Un-Incorporated SubDv.
  • 34786 Zip Code
11216 Rapallo Lane, Windermere image
11216 Rapallo Lane, Windermere $449,000

A MUST SEE in the gated Belmere Village! A newly renovated gem, that is move-in ready. Upon entering you see the open floor plan, the view of the pool through the sliding...

  • 4 Beds
  • 2.5 Baths
  • Belmere Village SubDv.
  • 34786 Zip Code
11946 Waterstone Loop Drive, Windermere image
11946 Waterstone Loop Drive, Windermere $1,118,000

Luxurious Silliman Custom Built Windermere Retreat with 4 bedrooms, 4 and a half baths overlooking a park-like pond is located in much sought after West Orange County sit...

  • 4 Beds
  • 4.5 Baths
  • Waterstone A D E F G H J L SubDv.
  • 34786 Zip Code
11555 Willow Gardens Drive, Windermere image
11555 Willow Gardens Drive, Windermere $599,900

PRICE ADJUSTMENT! This is a GREAT INVESTMENT OPPORTUNITY. This Stunning custom builds home features 3754/SQF of living area 5bedroom 4bathroom and 3 car garage screened b...

  • 5 Beds
  • 4 Baths
  • Willows At Lake Rhea Ph 03 SubDv.
  • 34786 Zip Code
13219 Charfield Street, Windermere image
13219 Charfield Street, Windermere $329,900

Come see this charming move-in ready home in the sought after community of Lake Sawyer South in Windermere. This open split plan has 3 bedrooms and 2 baths. You are welc...

  • 3 Beds
  • 2 Baths
  • Lake Sawyer South Ph 02 SubDv.
  • 34786 Zip Code
2545 Meadowview Circle, Windermere image
2545 Meadowview Circle, Windermere $564,000

***NEW tile ROOF coming soon! Windermere Downs, a community nestled along LAKE DOWN with access to the highly sought after BUTLER CHAIN of Lakes w/ windy lush landscaped ...

  • 4 Beds
  • 3.5 Baths
  • Windermere Downs SubDv.
  • 34786 Zip Code
2515 Crescent Pointe Court, Windermere image
2515 Crescent Pointe Court, Windermere $624,900

This gorgeous home is located on a 1.04 acre lot in Windermere at the end of a cul-de-sac, featuring an open floor plan. The 4 bedrooms and 3 baths are design in a split ...

  • 4 Beds
  • 3 Baths
  • Crescent Pointe SubDv.
  • 34786 Zip Code
11425 Waterstone Loop Drive, Windermere image
11425 Waterstone Loop Drive, Windermere $1,985,000

Lake Butler access!!! Stunning Contemporary and modern style home builded in 2017 in the amazing gated Waterstone Community with private access to Windermere Preparatory ...

  • 5 Beds
  • 5.5 Baths
  • Waterstone SubDv.
  • 34786 Zip Code
6453 Lake Burden View Drive, Windermere image
6453 Lake Burden View Drive, Windermere $2,390,000

BREATH TAKING LAKE and GOLF FRONT ESTATE at Butler Chain of Lakes in the UPSCALE and EXCLUSIVE Keene's Pointe gated community in Windermere. ONE OF A KIND custom home was...

  • 5 Beds
  • 6 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
8742 Peachtree Park Ct, Windermere image
8742 Peachtree Park Ct, Windermere $399,000

Enjoy living in a great location. This enchanted one-story level Key West Style home is located in desirable Peachtree Park subdivision. The home offers an unparalleled d...

  • 3 Beds
  • 2 Baths
  • Peachtree Park SubDv.
  • 34786 Zip Code
13745 Eden Isle Boulevard, Windermere image
13745 Eden Isle Boulevard, Windermere $395,900

Bring your buyers to this charming 3 bedroom, 2.5 bathroom pool home in the gated Eden Isle Community. This spacious home is move in ready. The welcoming front porch is a...

  • 3 Beds
  • 2 Baths
  • Eden Isle SubDv.
  • 34786 Zip Code
1702 Glenwick Drive, Windermere image
1702 Glenwick Drive, Windermere $559,300

Beautiful spacious home available in Windermere. Step inside to find 4 bedrooms, 4.5 baths, 3 car garage, soaring ceilings, family room and living room with fireplace, wo...

  • 5 Beds
  • 4.5 Baths
  • Reserve At Belmere 48 23 SubDv.
  • 34786 Zip Code
7421 Leighside Drive, Windermere image
7421 Leighside Drive, Windermere — Na $310,000

You can instantly unlock and tour this home any day of the week from 6am to 9pm, no appointment needed.

  • 3 Beds
  • 2.5 Baths
  • Lake Burden South Ph 2 SubDv.
  • 34786 Zip Code
4121 Clarice Estates Drive, Windermere image
4121 Clarice Estates Drive, Windermere $2,100,000

Live the dream in this spectacular luxurious designer residence. The grand entrance and manicured gardens set the tone for a home that will truly take your breath away....

  • 5 Beds
  • 8.5 Baths
  • Estates/Lk Clarice SubDv.
  • 34786 Zip Code
13145 Zori Lane, Windermere image
13145 Zori Lane, Windermere $475,000

Come see this Beautiful and very spacious home in the heart of Windermere. This home features an open floor plan with high vaulted ceilings. It boasts with a lot of upgr...

  • 5 Beds
  • 4 Baths
  • Providence Ph 01 50 03 SubDv.
  • 34786 Zip Code
9303 Sir Lawrence Court, Windermere image
9303 Sir Lawrence Court, Windermere $889,000

Rare opportunity to own this beautiful LAKEFRONT home on skiable Lake Olivia in Windermere. Enjoy colorful skies and sunsets from every room. Completely remodeled in 2012...

  • 5 Beds
  • 3 Baths
  • Roberts Landing SubDv.
  • 34786 Zip Code

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