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Windermere Real Estate Analysis

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Windermere with a population estimated to be around 2,300, Windermere has that small town feeling. It’s serene ways and great location have made it a desirable choice for families with children. Windermere has remained a popular town due to it’s numerous lakes and bordering, upscale communities. The picturesque, sandy bottom lakes of Lake Butler, Lake Bessie, and Lake Down along with other smaller lakes join together to form the Butler Chain of Lakes.
History: In 1885 Joseph Hill Scott purchased 150 acres in the Windermere area and supposedly named it after Lake Windermere in England. In 1889 a railroad was built from Kissimmee to Windermere. The city really started to grow in 1910 when two investors from Ohio decided to start developing the area.
Real Estate: The area slightly outside of Windermere is home to a growing real estate market for some of central Florida’s most expensive homes. The development of new real estate has led to a few pristine and upscale golf courses being created throughout the area.
Notable Nearby Communities:

  • Isleworth – Considered to be one of the countries premier country clubs and has a private golf course designed by Arnold Palmer. The estate homes in the 600 acre community range in price from 1 to 12 million dollars.
  • Butler Bay – Located between Lake Crescent and Lake Roberts. This community has an 18 hole golf course as well as many lake front properties. The lots are between half an acre and 2 acres.
  • Keene’s Point – A gated community containing 14 separate neighborhoods and is located on the shore of Lake Butler. The 250 acre private golf course is a signature design by Jack Nicklaus.

  • Stats: Population 2,300 70.3% married couples 11.1% of population over 65
    Location: Fourteen miles southwest of Orlando, six miles southeast of Winter Garden, two miles south of Ocoee.

    To find homes in Windermere, use our Real Estate Search with zip code 34786.

    Windermere Real Estate Listings

    Active Listings in Windermere

    2024 Bellamere Court WINDERMERE, FL 34786
    Photo of 2024 Bellamere Court, WINDERMERE, FL 34786 (MLS # O5837859)
    4 beds 5 baths 4,884 sqft $1,900,000
    12973 Borland Street WINDERMERE, FL 34786
    Photo of 12973 Borland Street, WINDERMERE, FL 34786 (MLS # S5028983)
    3 beds 3 baths 1,428 sqft $255,500
    14338 Red Cardinal Court WINDERMERE, FL 34786
    Photo of 14338 Red Cardinal Court, WINDERMERE, FL 34786 (MLS # O5838004)
    5 beds 3 baths 3,211 sqft $459,900
    13869 Amelia Pond Drive WINDERMERE, FL 34786
    Photo of 13869 Amelia Pond Drive, WINDERMERE, FL 34786 (MLS # O5837878)
    4 beds 3 baths 2,278 sqft $345,900
    1444 Whitney Isles Drive WINDERMERE, FL 34786
    Photo of 1444 Whitney Isles Drive, WINDERMERE, FL 34786 (MLS # O5835915)
    4 beds 4 baths 3,268 sqft $459,500
    11755 Bella Milano Court WINDERMERE, FL 34786
    Photo of 11755 Bella Milano Court, WINDERMERE, FL 34786 (MLS # S5028522)
    5 beds 5 baths 3,121 sqft $439,900
    2073 Roberts Point Drive WINDERMERE, FL 34786
    Photo of 2073 Roberts Point Drive, WINDERMERE, FL 34786 (MLS # O5837670)
    5 beds 6 baths 5,641 sqft $1,195,000
    8356 Bowden Way WINDERMERE, FL 34786
    Photo of 8356 Bowden Way, WINDERMERE, FL 34786 (MLS # O5837013)
    4 beds 4 baths 3,488 sqft $649,000
    2103 Butler Bay Drive N WINDERMERE, FL 34786
    Photo of 2103 Butler Bay Drive N, WINDERMERE, FL 34786 (MLS # O5837832)
    4 beds 3 baths 3,265 sqft $719,000
    2455 Maguire Road WINDERMERE, FL 34786
    Photo of 2455 Maguire Road, WINDERMERE, FL 34786 (MLS # O5837809)
    5 beds 5 baths 3,987 sqft $1,490,000
    6827 Thornhill Circle WINDERMERE, FL 34786
    Photo of 6827 Thornhill Circle, WINDERMERE, FL 34786 (MLS # O5837800)
    4 beds 3 baths 3,378 sqft $1,000,000
    9014 Via Di Canti Drive WINDERMERE, FL 34786
    Photo of 9014 Via Di Canti Drive, WINDERMERE, FL 34786 (MLS # O5837504)
    4 beds 4 baths 1,888 sqft $320,000
    5427 Gemgold Court WINDERMERE, FL 34786
    Photo of 5427 Gemgold Court, WINDERMERE, FL 34786 (MLS # O5837380)
    5 beds 4 baths 3,070 sqft $389,999
    8817 Danforth Drive WINDERMERE, FL 34786
    Photo of 8817 Danforth Drive, WINDERMERE, FL 34786 (MLS # O5836050)
    2 beds 3 baths 1,380 sqft $245,000
    9033 Tavolini Terrace WINDERMERE, FL 34786
    Photo of 9033 Tavolini Terrace, WINDERMERE, FL 34786 (MLS # G5024827)
    5 beds 5 baths 3,931 sqft $750,000

    Sold Listings in Windermere

    14156 Bridgewater Crossings Boulevard WINDERMERE, FL 34786
    Photo of 14156 Bridgewater Crossings Boulevard, WINDERMERE, FL 34786 (MLS # O5831461)
    3 beds 3 baths 1,485 sqft $260,000
    8342 Tibet Butler Drive WINDERMERE, FL 34786
    Photo of 8342 Tibet Butler Drive, WINDERMERE, FL 34786 (MLS # O5830154)
    5 beds 5 baths 3,924 sqft $835,000
    13459 Gorgona Isle Drive WINDERMERE, FL 34786
    Photo of 13459 Gorgona Isle Drive, WINDERMERE, FL 34786 (MLS # J910250)
    3 beds 3 baths 1,788 sqft $316,346
    13345 Gorgona Isle Drive WINDERMERE, FL 34786
    Photo of 13345 Gorgona Isle Drive, WINDERMERE, FL 34786 (MLS # J909913)
    3 beds 3 baths 1,570 sqft $288,444
    13635 Darchance Road WINDERMERE, FL 34786
    Photo of 13635 Darchance Road, WINDERMERE, FL 34786 (MLS # O5791389)
    4 beds 4 baths 2,699 sqft $398,000
    9519 Westover Club Circle WINDERMERE, FL 34786
    Photo of 9519 Westover Club Circle, WINDERMERE, FL 34786 (MLS # O5829531)
    4 beds 4 baths 3,633 sqft $590,000
    13000 Westside Village Loop WINDERMERE, FL 34786
    Photo of 13000 Westside Village Loop, WINDERMERE, FL 34786 (MLS # S5020898)
    5 beds 4 baths 3,689 sqft $426,000
    14269 Desert Haven Street, Unit 3401 WINDERMERE, FL 34786
    Photo of 14269 Desert Haven Street, Unit 3401, WINDERMERE, FL 34786 (MLS # O5829250)
    3 beds 3 baths 1,840 sqft $282,000
    MLS # O5816886 WINDERMERE, FL 34786
    Photo of WINDERMERE, FL 34786 (MLS # O5816886)
    5 beds 3 baths 4,895 sqft $561,900
    9526 Pine Terrace Court WINDERMERE, FL 34786
    Photo of 9526 Pine Terrace Court, WINDERMERE, FL 34786 (MLS # O5828449)
    3 beds 2 baths 1,814 sqft $305,000
    14248 Confetti Drive WINDERMERE, FL 34786
    Photo of 14248 Confetti Drive, WINDERMERE, FL 34786 (MLS # O5827873)
    4 beds 4 baths 2,132 sqft $285,000
    12784 Garridan Avenue WINDERMERE, FL 34786
    Photo of 12784 Garridan Avenue, WINDERMERE, FL 34786 (MLS # O5827919)
    4 beds 3 baths 2,044 sqft $318,000
    11746 Water Run Alley WINDERMERE, FL 34786
    Photo of 11746 Water Run Alley, WINDERMERE, FL 34786 (MLS # O5827694)
    3 beds 3 baths 1,629 sqft $285,000
    13874 Summerport Trail Loop WINDERMERE, FL 34786
    Photo of 13874 Summerport Trail Loop, WINDERMERE, FL 34786 (MLS # O5827136)
    4 beds 3 baths 2,233 sqft $325,500
    2037 Lake Crescent Court WINDERMERE, FL 34786
    Photo of 2037 Lake Crescent Court, WINDERMERE, FL 34786 (MLS # O5813810)
    4 beds 4 baths 2,649 sqft $610,000

    Windermere School Data

    Windermere School Districts

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    Windermere Schools

    Windermere Elementary School
    K-5, public
    Gotha Middle School
    6-8, public
    Buena Vista Academy
    PK-8, private
    Premier Academy
    K-1, private
    http://premieracademyschools.com/
    Windermere Preparatory School
    PK-12, private
    http://www.windermereprep.com/
    The Crenshaw School
    PK-12, private
    http://www.crenshawschool.com
    Sunset Park Elementary School
    K-5, public
    Keenes Crossing Elementary School
    PK-5, public
    The New Academy
    1-12, private