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Windermere Single Family Homes For Sale - 260 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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  • 516 JENNIFER LN, WINDERMERE, FL 34786

    $1,295,00022 Days on yellowkey   MLS ID: O6419731

    0 Days Off yellowkey (back on 6/29/2026)

    For Sale O6419731 - 516 JENNIFER LN, WINDERMERE, FL 34786 71 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3021
       Built: 1982
    Monthly Fee: $333
       Tax: $6,252 (2025)
    Community: Windermere Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,950 (change assumption)
    Mortgage ($7,096) + Fees ($333) + Taxes in 2025 ($521)


    Taxes:$6,252

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 11617 CAMDEN PARK DR, WINDERMERE, FL 34786

    $1,375,00070 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 64 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


  • 1408 LAKE WHITNEY DRIVE, WINDERMERE, FL 34786

    $2,650,00025 Days on yellowkey   MLS ID: O6418721

    For Sale O6418721 - 1408 LAKE WHITNEY DRIVE, WINDERMERE, FL 34786 80 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5433
       Built: 2003
    Monthly Fee: $271
       Tax: $24,189 (2025)
    Community: Reserve At Belmere Ph 02 48 144
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,807 (change assumption)
    Mortgage ($14,520) + Fees ($271) + Taxes in 2025 ($2,016)


    Taxes:$24,189

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13424 HOPKINTON CT, WINDERMERE, FL 34786

    $549,99922 Days on yellowkey   MLS ID: O6419100

    For Sale O6419100 - 13424 HOPKINTON CT, WINDERMERE, FL 34786 8 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2190
       Built: 2005
    Monthly Fee: $169
       Tax: $7,268 (2025)
    Community: Lakes Of Windermere-Peachtree
    Single Family


    Estimated Monthly Payment: $3,788 (change assumption)
    Mortgage ($3,014) + Fees ($169) + Taxes in 2025 ($606)


    Taxes:$7,268

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 9316 GLADYS GARDEN CT, WINDERMERE, FL 34786

    $6,500,00018 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


  • 9011 CHAPMAN OAK CT, WINDERMERE, FL 34786

    $599,00092 Days on yellowkey   MLS ID: S5148031

    REDUCED by $30,000 (4.8%) on 06/29/2026

    For Sale S5148031 - 9011 CHAPMAN OAK CT, WINDERMERE, FL 34786 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2050
       Built: 1987
    Monthly Fee: $31
       Tax: $8,592 (2025)
    Community: Silver Woods Ph 05
    Single Family


    Estimated Monthly Payment: $4,029 (change assumption)
    Mortgage ($3,282) + Fees ($31) + Taxes in 2025 ($716)


    Taxes:$8,592

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786

    $6,000,000196 Days on yellowkey   MLS ID: O6370294

    REDUCED by $150,000 (2.4%) on 05/01/2026

    For Sale O6370294 - 9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786 64 photos

    Bed: 7   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 8000
       Built: 1999
    Monthly Fee: $1,043
       Tax: $29,046 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $36,339 (change assumption)
    Mortgage ($32,876) + Fees ($1,043) + Taxes in 2024 ($2,421)


    Taxes:$29,046

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 1554 LAKE RHEA DR, WINDERMERE, FL 34786

    $1,350,00070 Days on yellowkey   MLS ID: O6406297

    REDUCED by $50,000 (3.6%) on 05/29/2026

    For Sale O6406297 - 1554 LAKE RHEA DR, WINDERMERE, FL 34786 59 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3427
       Built: 2004
    Monthly Fee: $241
       Tax: $9,102 (2025)
    Community: Reserve At Belmere
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,397 (change assumption)
    Mortgage ($7,397) + Fees ($241) + Taxes in 2025 ($759)


    Taxes:$9,102

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9110 PALM TREE DR, WINDERMERE, FL 34786

    $650,00035 Days on yellowkey   MLS ID: O6414631

    REDUCED by $25,000 (3.7%) on 06/29/2026

    For Sale O6414631 - 9110 PALM TREE DR, WINDERMERE, FL 34786 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1819
       Built: 1985
    Monthly Fee: $32
       Tax: $8,182 (2025)
    Community: Silver Woods Ph 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,275 (change assumption)
    Mortgage ($3,562) + Fees ($32) + Taxes in 2025 ($682)


    Taxes:$8,182

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 6601 DUNCASTER ST, WINDERMERE, FL 34786

    $627,90036 Days on yellowkey   MLS ID: O6416272

    REDUCED by $100 (0.0%) on 06/22/2026

    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: $4,312 (change assumption)
    Mortgage ($3,440) + 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


  • 12720 JACOB GRACE CT, WINDERMERE, FL 34786

    $2,750,000134 Days on yellowkey   MLS ID: TB8476930

    1 Days Off yellowkey (back on 6/29/2026)

    REDUCED by $95,000 (3.3%) on 06/16/2026

    For Sale TB8476930 - 12720 JACOB GRACE CT, WINDERMERE, FL 34786 88 photos

    Bed: 6   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5882
       Built: 2005
    Monthly Fee: $300
       Tax: $13,298 (2024)
    Community: Tildens Grove Ph 01 47/65
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,476 (change assumption)
    Mortgage ($15,068) + Fees ($300) + Taxes in 2024 ($1,108)


    Taxes:$13,298

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 9620 MAYWOOD DR, WINDERMERE, FL 34786

    $2,349,00093 Days on yellowkey   MLS ID: O6399315

    REDUCED by $51,000 (2.1%) on 06/16/2026

    For Sale O6399315 - 9620 MAYWOOD DR, WINDERMERE, FL 34786 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3004
       Built: 1979   Tax: $20,433 (2025)
    Community: Lake Down Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $14,574 (change assumption)
    Mortgage ($12,871) + Taxes in 2025 ($1,703)


    Taxes:$20,433

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 6965 TETTENHALL LN, WINDERMERE, FL 34786

    $699,000289 Days on yellowkey   MLS ID: O6340538

    REDUCED by $11,000 (1.5%) on 06/28/2026

    For Sale O6340538 - 6965 TETTENHALL LN, WINDERMERE, FL 34786 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3050
       Built: 2007
    Monthly Fee: $75
       Tax: $4,946 (2024)
    Community: Lakes/Windermere Ph 04
    Single Family


    Estimated Monthly Payment: $4,317 (change assumption)
    Mortgage ($3,830) + Fees ($75) + Taxes in 2024 ($412)


    Taxes:$4,946

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 9663 GOTHA RD, WINDERMERE, FL 34786

    $1,299,90092 Days on yellowkey   MLS ID: O6399130

    REDUCED by $100,100 (7.2%) on 05/17/2026

    For Sale O6399130 - 9663 GOTHA RD, WINDERMERE, FL 34786 100 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3731
       Built: 2000   Tax: $8,425 (2025)
    Community: Gotha Town
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,825 (change assumption)
    Mortgage ($7,123) + Taxes in 2025 ($702)


    Taxes:$8,425

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 4303 ISABELLA CIR, WINDERMERE, FL 34786

    $2,899,00052 Days on yellowkey   MLS ID: O6409406

    For Sale O6409406 - 4303 ISABELLA CIR, WINDERMERE, FL 34786 100 photos

    Bed: 7   Bath: 5.0   Gar: 5
    Liv Area Sq Ft: 5122
       Built: 2017
    Monthly Fee: $480
       Tax: $22,725 (2025)
    Community: Casabella
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $18,258 (change assumption)
    Mortgage ($15,885) + Fees ($480) + Taxes in 2025 ($1,894)


    Taxes:$22,725

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13339 ROSKIN LN, WINDERMERE, FL 34786

    $680,000188 Days on yellowkey   MLS ID: S5141148

    For Sale S5141148 - 13339 ROSKIN LN, WINDERMERE, FL 34786 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2947
       Built: 2012
    Monthly Fee: $82
       Tax: $8,674 (2024)
    Community: Lake Sawyer South Ph 01
    Single Family


    Estimated Monthly Payment: $4,531 (change assumption)
    Mortgage ($3,726) + Fees ($82) + Taxes in 2024 ($723)


    Taxes:$8,674

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 1009 DOWN RESERVE CT, WINDERMERE, FL 34786

    $3,950,000297 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


  • 3057 PORTO LAGO CT, WINDERMERE, FL 34786

    $13,995,00034 Days on yellowkey   MLS ID: O6411245

    For Sale O6411245 - 3057 PORTO LAGO CT, WINDERMERE, FL 34786 98 photos

    Bed: 6   Bath: 8.5   Gar: 8
    Liv Area Sq Ft: 12067
       Built: 2026
    Monthly Fee: $375
       Tax: $18,356 (2025)
    Community: Lake Down Pointe 50 42
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $78,588 (change assumption)
    Mortgage ($76,683) + Fees ($375) + Taxes in 2025 ($1,530)


    Taxes:$18,356

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 13330 LONGACRE DR, WINDERMERE, FL 34786

    $550,00026 Days on yellowkey   MLS ID: O6418405

    For Sale O6418405 - 13330 LONGACRE DR, WINDERMERE, FL 34786 17 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


  • 5128 BUTLER RIDGE DR, WINDERMERE, FL 34786

    $1,175,00049 Days on yellowkey   MLS ID: O6412016

    2 Days Off yellowkey (back on 6/27/2026)

    REDUCED by $75,000 (6.0%) on 06/04/2026

    For Sale O6412016 - 5128 BUTLER RIDGE DR, WINDERMERE, FL 34786 35 photos

    Bed: 4   Bath: 3.0   Gar: 7
    Liv Area Sq Ft: 2816
       Built: 1989   Tax: $9,506 (2025)
    Community: Butler Ridge
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,230 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($792)


    Taxes:$9,506

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater 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.