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Windermere Single Family Homes For Sale - 259 homes

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

Location: Windermere

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  • 5538 W LAKE BUTLER RD, WINDERMERE, FL 34786

    $3,195,000174 Days on yellowkey   MLS ID: O6376859

    3 Days Off yellowkey (back on 7/20/2026)

    REDUCED by $300,000 (8.6%) on 05/15/2026

    For Sale O6376859 - 5538 W LAKE BUTLER RD, WINDERMERE, FL 34786 71 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6000
       Built: 1982
    Monthly Fee: $67
       Tax: $25,546 (2025)
    Community: Kelso On Lake Butler
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,702 (change assumption)
    Mortgage ($17,506) + Fees ($67) + Taxes in 2025 ($2,129)


    Taxes:$25,546

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9316 GLADYS GARDEN CT, WINDERMERE, FL 34786

    $6,500,00022 Days on yellowkey   MLS ID: O6420326

    For Sale O6420326 - 9316 GLADYS GARDEN CT, WINDERMERE, FL 34786 73 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5471
       Built: 2026
    Monthly Fee: $2,370
       Tax: $9,424 (2025)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $38,771 (change assumption)
    Mortgage ($35,616) + Fees ($2,370) + Taxes in 2025 ($785)


    Taxes:$9,424

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 9150 OUTLOOK ROCK TRL, WINDERMERE, FL 34786

    $915,000131 Days on yellowkey   MLS ID: S5145642

    For Sale S5145642 - 9150 OUTLOOK ROCK TRL, WINDERMERE, FL 34786 27 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2988
       Built: 2015
    Monthly Fee: $13
       Tax: $10,964 (2024)
    Community: Windermere Trls Ph 5B
    Single Family


    Estimated Monthly Payment: $5,940 (change assumption)
    Mortgage ($5,014) + Fees ($13) + Taxes in 2024 ($914)


    Taxes:$10,964

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 8552 POWDER RIDGE TRL, WINDERMERE, FL 34786

    $680,000146 Days on yellowkey   MLS ID: S5144276

    0 Days Off yellowkey (back on 7/3/2026)

    For Sale S5144276 - 8552 POWDER RIDGE TRL, WINDERMERE, FL 34786 30 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2612
       Built: 2016
    Monthly Fee: $82
       Tax: $8,150 (2024)
    Community: Windermere Trls Ph 3B
    Single Family


    Estimated Monthly Payment: $4,487 (change assumption)
    Mortgage ($3,726) + Fees ($82) + Taxes in 2024 ($679)


    Taxes:$8,150

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6363 SEDONA LEAF CT, WINDERMERE, FL 34786

    $749,90033 Days on yellowkey   MLS ID: O6416993

    For Sale O6416993 - 6363 SEDONA LEAF CT, WINDERMERE, FL 34786 38 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2665
       Built: 2004
    Monthly Fee: $111
       Tax: $10,803 (2025)
    Community: Eden Isle Boat Ramp
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,120 (change assumption)
    Mortgage ($4,109) + Fees ($111) + Taxes in 2025 ($900)


    Taxes:$10,803

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5199 LATROBE DR, WINDERMERE, FL 34786

    $5,300,00055 Days on yellowkey   MLS ID: O6409961

    For Sale O6409961 - 5199 LATROBE DR, WINDERMERE, FL 34786 64 photos

    Bed: 6   Bath: 6.5   Gar: 4
    Liv Area Sq Ft: 4665
       Built: 1993
    Monthly Fee: $1,224
       Tax: $37,241 (2025)
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $33,368 (change assumption)
    Mortgage ($29,040) + Fees ($1,224) + Taxes in 2025 ($3,103)


    Taxes:$37,241

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 12417 MONTALCINO CIR, WINDERMERE, FL 34786

    $1,595,000Listed 07/20/2026 9:06AM   MLS ID: O6425494

    For Sale O6425494 - 12417 MONTALCINO CIR, WINDERMERE, FL 34786 100 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3166
       Built: 2012
    Monthly Fee: $150
       Tax: $11,488 (2025)
    Community: Casa Del Lago-Replat
    Single Family


    Estimated Monthly Payment: $9,847 (change assumption)
    Mortgage ($8,740) + Fees ($150) + Taxes in 2025 ($957)


    Taxes:$11,488

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13542 GORGONA ISLE DR, WINDERMERE, FL 34786

    $879,000130 Days on yellowkey   MLS ID: O6390582

    REDUCED by $16,000 (1.8%) on 07/17/2026

    For Sale O6390582 - 13542 GORGONA ISLE DR, WINDERMERE, FL 34786 10 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2224
       Built: 2018
    Monthly Fee: $268
       Tax: $9,762 (2024)
    Community: Windermere Isle
    Single Family


    Estimated Monthly Payment: $5,898 (change assumption)
    Mortgage ($4,816) + Fees ($268) + Taxes in 2024 ($814)


    Taxes:$9,762

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786

    $2,240,000305 Days on yellowkey   MLS ID: O6344907

    REDUCED by $100,000 (4.3%) on 07/20/2026

    For Sale O6344907 - 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786 53 photos

    Bed: 4   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4810
       Built: 2002
    Monthly Fee: $277
       Tax: $17,161 (2024)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,981 (change assumption)
    Mortgage ($12,274) + Fees ($277) + Taxes in 2024 ($1,430)


    Taxes:$17,161

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 11015 HAWKSHEAD CT, WINDERMERE, FL 34786

    $1,450,00062 Days on yellowkey   MLS ID: O6405977

    REDUCED by $39,999 (2.7%) on 07/20/2026

    For Sale O6405977 - 11015 HAWKSHEAD CT, WINDERMERE, FL 34786 42 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3868
       Built: 2004
    Monthly Fee: $640
       Tax: $18,824 (2025)
    Community: Reserve At Lake Butler Sound
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,154 (change assumption)
    Mortgage ($7,945) + Fees ($640) + Taxes in 2025 ($1,569)


    Taxes:$18,824

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 4474 BEGONIA CT, WINDERMERE, FL 34786

    $1,070,00087 Days on yellowkey   MLS ID: O6402227

    REDUCED by $50,000 (4.5%) on 07/14/2026

    For Sale O6402227 - 4474 BEGONIA CT, WINDERMERE, FL 34786 41 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4380
       Built: 1998
    Monthly Fee: $133
       Tax: $7,670 (2025)
    Community: Magnolia Park Windermere
    Single Family


    Estimated Monthly Payment: $6,635 (change assumption)
    Mortgage ($5,863) + Fees ($133) + Taxes in 2025 ($639)


    Taxes:$7,670

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11249 RAPALLO LN, WINDERMERE, FL 34786

    $750,00020 Days on yellowkey   MLS ID: O6421056

    2 Days Off yellowkey (back on 7/20/2026)

    For Sale O6421056 - 11249 RAPALLO LN, WINDERMERE, FL 34786 37 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2366
       Built: 2002
    Monthly Fee: $136
       Tax: $9,355 (2025)
    Community: Belmere Village G2 48 65
    Single Family


    Estimated Monthly Payment: $5,025 (change assumption)
    Mortgage ($4,109) + Fees ($136) + Taxes in 2025 ($780)


    Taxes:$9,355

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 11617 CAMDEN PARK DR, WINDERMERE, FL 34786

    $1,375,00074 Days on yellowkey   MLS ID: O6405409

    REDUCED by $22,000 (1.6%) on 06/18/2026

    For Sale O6405409 - 11617 CAMDEN PARK DR, WINDERMERE, FL 34786 65 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3463
       Built: 2005
    Monthly Fee: $283
       Tax: $7,189 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $8,416 (change assumption)
    Mortgage ($7,534) + Fees ($283) + Taxes in 2025 ($599)


    Taxes:$7,189

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6601 DUNCASTER ST, WINDERMERE, FL 34786

    $624,90040 Days on yellowkey   MLS ID: O6416272

    REDUCED by $3,000 (0.5%) on 07/20/2026

    For Sale O6416272 - 6601 DUNCASTER ST, WINDERMERE, FL 34786 65 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3001
       Built: 2006
    Monthly Fee: $82
       Tax: $9,473 (2025)
    Community: Lakes/Windermere Ph 02A
    Single Family


    Estimated Monthly Payment: $4,295 (change assumption)
    Mortgage ($3,424) + Fees ($82) + Taxes in 2025 ($789)


    Taxes:$9,473

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 5624 W LAKE BUTLER RD, WINDERMERE, FL 34786

    $2,375,00048 Days on yellowkey   MLS ID: O6411407

    REDUCED by $175,000 (6.9%) on 07/08/2026

    For Sale O6411407 - 5624 W LAKE BUTLER RD, WINDERMERE, FL 34786 81 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3736
       Built: 2016
    Monthly Fee: $67
       Tax: $15,440 (2025)
    Community: Kelso On Lake Butler
    Single Family


    Estimated Monthly Payment: $14,367 (change assumption)
    Mortgage ($13,013) + Fees ($67) + Taxes in 2025 ($1,287)


    Taxes:$15,440

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8254 PROCIDA ISLE LN, WINDERMERE, FL 34786

    $1,050,0001 Day on yellowkey   MLS ID: G5115289

    For Sale G5115289 - 8254 PROCIDA ISLE LN, WINDERMERE, FL 34786 52 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3267
       Built: 2019
    Monthly Fee: $297
       Tax: $11,840 (2025)
    Community: Windermere Isle Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,037 (change assumption)
    Mortgage ($5,753) + Fees ($297) + Taxes in 2025 ($987)


    Taxes:$11,840

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6417 LAKE BURDEN VIEW DR, WINDERMERE, FL 34786

    $2,960,00021 Days on yellowkey   MLS ID: O6418943

    For Sale O6418943 - 6417 LAKE BURDEN VIEW DR, WINDERMERE, FL 34786 86 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 5935
       Built: 2006
    Monthly Fee: $298
       Tax: $25,461 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $18,639 (change assumption)
    Mortgage ($16,219) + Fees ($298) + Taxes in 2025 ($2,122)


    Taxes:$25,461

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8355 TORCELLO ISLE DR, WINDERMERE, FL 34786

    $925,00069 Days on yellowkey   MLS ID: O6407061

    REDUCED by $25,000 (2.6%) on 07/10/2026

    For Sale O6407061 - 8355 TORCELLO ISLE DR, WINDERMERE, FL 34786 73 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4202
       Built: 2019
    Monthly Fee: $299
       Tax: $9,036 (2025)
    Community: Windermere Isle
    Single Family


    Estimated Monthly Payment: $6,120 (change assumption)
    Mortgage ($5,068) + Fees ($299) + Taxes in 2025 ($753)


    Taxes:$9,036

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 4309 SALTMARSH SPARROW DR, WINDERMERE, FL 34786

    $760,000109 Days on yellowkey   MLS ID: O6396295

    REDUCED by $15,000 (1.9%) on 07/08/2026

    For Sale O6396295 - 4309 SALTMARSH SPARROW DR, WINDERMERE, FL 34786 45 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3697
       Built: 2015
    Monthly Fee: $130
       Tax: $8,724 (2025)
    Community: Stillwater Xings Prcl Sc-13 Ph
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,021 (change assumption)
    Mortgage ($4,164) + Fees ($130) + Taxes in 2025 ($727)


    Taxes:$8,724

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1009 DOWN RESERVE CT, WINDERMERE, FL 34786

    $3,950,000301 Days on yellowkey   MLS ID: O6346638

    REDUCED by $700,000 (15.1%) on 06/28/2026

    For Sale O6346638 - 1009 DOWN RESERVE CT, WINDERMERE, FL 34786 73 photos

    Bed: 5   Bath: 7.0   Gar: 4
    Liv Area Sq Ft: 7940
       Built: 2026
    Monthly Fee: $433
       Tax: $7,458 (2025)
    Community: Lake Down Reserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $22,698 (change assumption)
    Mortgage ($21,643) + Fees ($433) + Taxes in 2025 ($622)


    Taxes:$7,458

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle




Why Bother Searching Elsewhere for Windermere Single Family Homes for Sale?

Windermere home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Windermere . You can use our website to view Multiple Listing Service (MLS) data on Windermere single family homes. 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 single family home 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.