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Windermere Homes For Sale & Real Estate - 336 homes

Windermere homes for sale are located in Orange County, Florida. Find homes in Windermere for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Windermere houses.

Location: Windermere

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  • 14506 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786

    $410,0005 Days on yellowkey   MLS ID: O6417034

    For Sale O6417034 - 14506 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 2006
    Monthly Fee: $201
       Tax: $2,500 (2025)
    Community: Tennyson Pk/Summerport
    Townhouse


    Estimated Monthly Payment: $2,656 (change assumption)
    Mortgage ($2,247) + Fees ($201) + Taxes in 2025 ($208)


    Taxes:$2,500

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13330 LONGACRE DR, WINDERMERE, FL 34786

    $550,0003 Days on yellowkey   MLS ID: O6418405

    For Sale O6418405 - 13330 LONGACRE DR, WINDERMERE, FL 34786 13 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2306
       Built: 2013
    Monthly Fee: $115
       Tax: $8,281 (2025)
    Community: Windermere Terrace
    Single Family


    Estimated Monthly Payment: $3,819 (change assumption)
    Mortgage ($3,014) + Fees ($115) + Taxes in 2025 ($690)


    Taxes:$8,281

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11407 WILLOW GARDENS DR, WINDERMERE, FL 34786

    $1,200,0004 Days on yellowkey   MLS ID: O6417997

    0 Days Off yellowkey (back on 6/21/2026)

    For Sale O6417997 - 11407 WILLOW GARDENS DR, WINDERMERE, FL 34786 53 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3501
       Built: 1992
    Monthly Fee: $122
       Tax: $12,617 (2025)
    Community: Willows At Lake Rhea Ph 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,749 (change assumption)
    Mortgage ($6,575) + Fees ($122) + Taxes in 2025 ($1,051)


    Taxes:$12,617

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6558 HELMSLEY CIR, WINDERMERE, FL 34786

    $635,00013 Days on yellowkey   MLS ID: S5151342

    For Sale S5151342 - 6558 HELMSLEY CIR, WINDERMERE, FL 34786 57 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2575
       Built: 2009
    Monthly Fee: $129
       Tax: $4,553 (2025)
    Community: Preston Square
    Single Family


    Estimated Monthly Payment: $3,988 (change assumption)
    Mortgage ($3,479) + Fees ($129) + Taxes in 2025 ($379)


    Taxes:$4,553

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8821 DANFORTH DR, WINDERMERE, FL 34786

    $355,00013 Days on yellowkey   MLS ID: O6415522

    0 Days Off yellowkey (back on 6/21/2026)

    For Sale O6415522 - 8821 DANFORTH DR, WINDERMERE, FL 34786 29 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1480
       Built: 2004
    Monthly Fee: $200
       Tax: $5,493 (2025)
    Community: Lakes/Windermere-Lk Reams Twnh
    Townhouse


    Estimated Monthly Payment: $2,603 (change assumption)
    Mortgage ($1,945) + Fees ($200) + Taxes in 2025 ($458)


    Taxes:$5,493

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 14371 CREST PALM AVE, WINDERMERE, FL 34786

    $1,049,99079 Days on yellowkey   MLS ID: G5110664

    REDUCED by $64,999 (5.8%) on 06/17/2026

    For Sale G5110664 - 14371 CREST PALM AVE, WINDERMERE, FL 34786 42 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3100
       Built: 2025
    Monthly Fee: $245
       Tax: $1,309 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,107 (change assumption)
    Mortgage ($5,753) + Fees ($245) + Taxes in 2025 ($109)


    Taxes:$1,309

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13124 FILLY CT, WINDERMERE, FL 34786

    $1,575,000425 Days on yellowkey   MLS ID: O6303140

    For Sale O6303140 - 13124 FILLY CT, WINDERMERE, FL 34786 51 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3300
       Built: 1989
    Monthly Fee: $46
       Tax: $15,459 (2024)
    Community: Farms
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,964 (change assumption)
    Mortgage ($8,630) + Fees ($46) + Taxes in 2024 ($1,288)


    Taxes:$15,459

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 13836 BLUEBIRD POND RD, WINDERMERE, FL 34786

    $675,00057 Days on yellowkey   MLS ID: TB8502779

    REDUCED by $23,000 (3.3%) on 06/04/2026

    For Sale TB8502779 - 13836 BLUEBIRD POND RD, WINDERMERE, FL 34786 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2108
       Built: 2004
    Monthly Fee: $100
       Tax: $3,052 (2025)
    Community: Summerport
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,053 (change assumption)
    Mortgage ($3,699) + Fees ($100) + Taxes in 2025 ($254)


    Taxes:$3,052

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9117 OUTLOOK ROCK TRL, WINDERMERE, FL 34786

    $1,125,00019 Days on yellowkey   MLS ID: O6413948

    For Sale O6413948 - 9117 OUTLOOK ROCK TRL, WINDERMERE, FL 34786 37 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4936
       Built: 2014
    Monthly Fee: $94
       Tax: $15,179 (2025)
    Community: Windermere Trls Ph 5A
    Single Family


    Estimated Monthly Payment: $7,523 (change assumption)
    Mortgage ($6,164) + Fees ($94) + Taxes in 2025 ($1,265)


    Taxes:$15,179

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 14422 CREST PALM AVE, WINDERMERE, FL 34786

    $1,100,0004 Days on yellowkey   MLS ID: O6418503

    For Sale O6418503 - 14422 CREST PALM AVE, WINDERMERE, FL 34786 30 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3140
       Built: 2025
    Monthly Fee: $245
       Tax: $2,889 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,513 (change assumption)
    Mortgage ($6,027) + Fees ($245) + Taxes in 2025 ($241)


    Taxes:$2,889

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 8582 POWDER RIDGE TRL, WINDERMERE, FL 34786

    $670,000323 Days on yellowkey   MLS ID: S5132123

    For Sale S5132123 - 8582 POWDER RIDGE TRL, WINDERMERE, FL 34786 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2297
       Built: 2017
    Monthly Fee: $81
       Tax: $8,182 (2024)
    Community: Windermere Trls Ph 3B
    Single Family


    Estimated Monthly Payment: $4,434 (change assumption)
    Mortgage ($3,671) + Fees ($81) + Taxes in 2024 ($682)


    Taxes:$8,182

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 9011 PINNACLE CIR, WINDERMERE, FL 34786

    $2,250,00065 Days on yellowkey   MLS ID: O6400872

    0 Days Off yellowkey (back on 6/20/2026)

    For Sale O6400872 - 9011 PINNACLE CIR, WINDERMERE, FL 34786 53 photos

    Bed: 5   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 6546
       Built: 2002
    Monthly Fee: $172
       Tax: $23,090 (2025)
    Community: Lake Down Crest
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,425 (change assumption)
    Mortgage ($12,328) + Fees ($172) + Taxes in 2025 ($1,924)


    Taxes:$23,090

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 6648 HELSTON LN, WINDERMERE, FL 34786

    $665,0009 Days on yellowkey   MLS ID: O6413354

    0 Days Off yellowkey (back on 6/20/2026)

    For Sale O6413354 - 6648 HELSTON LN, WINDERMERE, FL 34786 47 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3072
       Built: 2005
    Monthly Fee: $82
       Tax: $9,709 (2025)
    Community: Lakes/Windermere Ph 02A
    Single Family


    Estimated Monthly Payment: $4,535 (change assumption)
    Mortgage ($3,644) + Fees ($82) + Taxes in 2025 ($809)


    Taxes:$9,709

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11326 LEDGEMENT LN, WINDERMERE, FL 34786

    $899,99934 Days on yellowkey   MLS ID: O6409714

    REDUCED by $19,001 (2.1%) on 06/20/2026

    For Sale O6409714 - 11326 LEDGEMENT LN, WINDERMERE, FL 34786 63 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3182
       Built: 2002
    Monthly Fee: $170
       Tax: $9,509 (2025)
    Community: Glenmuir 48 39
    Single Family


    Estimated Monthly Payment: $5,894 (change assumption)
    Mortgage ($4,931) + Fees ($170) + Taxes in 2025 ($792)


    Taxes:$9,509

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11545 BRICKYARD POND LN, WINDERMERE, FL 34786

    $2,200,000127 Days on yellowkey   MLS ID: O6378961

    For Sale O6378961 - 11545 BRICKYARD POND LN, WINDERMERE, FL 34786 35 photos

    Bed: 8   Bath: 8.5   Gar: 3
    Liv Area Sq Ft: 4735
       Built: 2014
    Monthly Fee: $91
       Tax: $22,505 (2024)
    Community: Lake Burden South Ph I
    Single Family


    Estimated Monthly Payment: $14,021 (change assumption)
    Mortgage ($12,054) + Fees ($91) + Taxes in 2024 ($1,875)


    Taxes:$22,505

    Elementary School: Sunset Park Elem

    High School: None

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 9648 WEATHERSTONE CT, WINDERMERE, FL 34786

    $2,500,00065 Days on yellowkey   MLS ID: O6400680

    For Sale O6400680 - 9648 WEATHERSTONE CT, WINDERMERE, FL 34786 65 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4482
       Built: 2000
    Monthly Fee: $227
       Tax: $20,450 (2025)
    Community: Weatherstone On Lake Olivia
    Spa: No

    Single Family


    Estimated Monthly Payment: $15,629 (change assumption)
    Mortgage ($13,698) + Fees ($227) + Taxes in 2025 ($1,704)


    Taxes:$20,450

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 12929 WESTSIDE VILLAGE LOOP, WINDERMERE, FL 34786

    $950,0007 Days on yellowkey   MLS ID: O6417680

    For Sale O6417680 - 12929 WESTSIDE VILLAGE LOOP, WINDERMERE, FL 34786 58 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4043
       Built: 2017
    Monthly Fee: $133
       Tax: $13,487 (2025)
    Community: Westside Village
    Single Family


    Estimated Monthly Payment: $6,462 (change assumption)
    Mortgage ($5,205) + Fees ($133) + Taxes in 2025 ($1,124)


    Taxes:$13,487

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2503 BUTLER BAY DR N, WINDERMERE, FL 34786

    $1,799,00021 Days on yellowkey   MLS ID: O6413242

    For Sale O6413242 - 2503 BUTLER BAY DR N, WINDERMERE, FL 34786 98 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3297
       Built: 1990
    Monthly Fee: $199
       Tax: $16,376 (2025)
    Community: Windermere Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,421 (change assumption)
    Mortgage ($9,857) + Fees ($199) + Taxes in 2025 ($1,365)


    Taxes:$16,376

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8266 BRYCE CANYON AVE, WINDERMERE, FL 34786

    $489,50013 Days on yellowkey   MLS ID: O6410344

    For Sale O6410344 - 8266 BRYCE CANYON AVE, WINDERMERE, FL 34786 57 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1825
       Built: 2016
    Monthly Fee: $81
       Tax: $5,441 (2025)
    Community: Windermere Trls Ph 3B
    Single Family


    Estimated Monthly Payment: $3,217 (change assumption)
    Mortgage ($2,682) + Fees ($81) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 4718 BLUE MAJOR DR, WINDERMERE, FL 34786

    $520,00021 Days on yellowkey   MLS ID: O6410820

    For Sale O6410820 - 4718 BLUE MAJOR DR, WINDERMERE, FL 34786 61 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1911
       Built: 2005
    Monthly Fee: $143
       Tax: $7,296 (2025)
    Community: Summerport Ph 05
    Single Family


    Estimated Monthly Payment: $3,600 (change assumption)
    Mortgage ($2,849) + Fees ($143) + Taxes in 2025 ($608)


    Taxes:$7,296

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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Windermere home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Windermere . You can use our website to view Multiple Listing Service (MLS) data on Windermere Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Windermere listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.