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Displaying: For Sale

Location: Windermere

Property Type(s): Single Family

Price: $1,000,000+

Windermere - 178 properties found

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  • 9575 WESTOVER ROBERTS RD, WINDERMERE, FL 34786

    $4,850,000210 Days on yellowkey   MLS ID: O6357873

    REDUCED by $75,000 (1.5%) on 05/11/2026

    For Sale O6357873 - 9575 WESTOVER ROBERTS RD, WINDERMERE, FL 34786 95 photos

    Bed: 7   Bath: 8.0   Gar: 6
    Liv Area Sq Ft: 8931
       Built: 2008   Tax: $30,908 (2024)
    Community: Gotha Town
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $29,150 (change assumption)
    Mortgage ($26,575) + Taxes in 2024 ($2,576)


    Taxes:$30,908

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 11472 PARK AVE NE, WINDERMERE, FL 34786

    $1,125,000147 Days on yellowkey   MLS ID: G5105731

    5 Days Off yellowkey (back on 4/28/2026)

    For Sale G5105731 - 11472 PARK AVE NE, WINDERMERE, FL 34786 67 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3166
       Built: 1985
    Monthly Fee: $21
       Tax: $5,774 (2025)
    Community: Windermere
    Single Family


    Estimated Monthly Payment: $6,666 (change assumption)
    Mortgage ($6,164) + Fees ($21) + Taxes in 2025 ($481)


    Taxes:$5,774

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Gotha Middle


  • 6606 SAWYER SHORES LN, WINDERMERE, FL 34786

    $2,500,000103 Days on yellowkey   MLS ID: O6386058

    For Sale O6386058 - 6606 SAWYER SHORES LN, WINDERMERE, FL 34786 19 photos

    Bed: 5   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 5516
       Built: 2025   Tax: $3,720 (2024)
    Community: Sawyer Shores Sub
    Single Family


    Estimated Monthly Payment: $14,008 (change assumption)
    Mortgage ($13,698) + Taxes in 2024 ($310)


    Taxes:$3,720

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6560 LAKE BURDEN VIEW DR, WINDERMERE, FL 34786

    $1,890,000110 Days on yellowkey   MLS ID: O6381835

    For Sale O6381835 - 6560 LAKE BURDEN VIEW DR, WINDERMERE, FL 34786 30 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3687
       Built: 2006
    Monthly Fee: $298
       Tax: $24,050 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,658 (change assumption)
    Mortgage ($10,356) + Fees ($298) + Taxes in 2025 ($2,004)


    Taxes:$24,050

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13420 BONICA WAY, WINDERMERE, FL 34786

    $1,875,000256 Days on yellowkey   MLS ID: O6347722

    For Sale O6347722 - 13420 BONICA WAY, WINDERMERE, FL 34786 63 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4489
       Built: 2006
    Monthly Fee: $297
       Tax: $19,325 (2025)
    Community: Tildens Grove
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,181 (change assumption)
    Mortgage ($10,274) + Fees ($297) + Taxes in 2025 ($1,610)


    Taxes:$19,325

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5070 DOWN POINT LN, WINDERMERE, FL 34786

    $4,995,000103 Days on yellowkey   MLS ID: O6385276

    For Sale O6385276 - 5070 DOWN POINT LN, WINDERMERE, FL 34786 57 photos

    Bed: 6   Bath: 6.5   Gar: 4
    Liv Area Sq Ft: 7349
       Built: 1998
    Monthly Fee: $229
       Tax: $58,446 (2025)
    Community: Sunset Bay
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $32,469 (change assumption)
    Mortgage ($27,369) + Fees ($229) + Taxes in 2025 ($4,871)


    Taxes:$58,446

    Elementary School: Windermere Elem

    High School: None

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786

    $5,500,00045 Days on yellowkey   MLS ID: O6401757

    For Sale O6401757 - 5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786 51 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4330
       Built: 1994
    Monthly Fee: $1,224
       Tax: $19,599 (2025)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $32,994 (change assumption)
    Mortgage ($30,136) + Fees ($1,224) + Taxes in 2025 ($1,633)


    Taxes:$19,599

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 436 E 7TH AVE, WINDERMERE, FL 34786

    $2,175,000244 Days on yellowkey   MLS ID: O6350454

    For Sale O6350454 - 436 E 7TH AVE, WINDERMERE, FL 34786 30 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3136
       Built: 2025   Tax: $13,016 (2025)
    Community: Windermere Town Rep
    Single Family


    Estimated Monthly Payment: $13,002 (change assumption)
    Mortgage ($11,918) + Taxes in 2025 ($1,085)


    Taxes:$13,016

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5151 LATROBE DR, WINDERMERE, FL 34786

    $3,900,00081 Days on yellowkey   MLS ID: O6392380

    REDUCED by $200,000 (4.9%) on 05/05/2026

    For Sale O6392380 - 5151 LATROBE DR, WINDERMERE, FL 34786 57 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5301
       Built: 2000
    Monthly Fee: $1,224
       Tax: $23,020 (2025)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $24,512 (change assumption)
    Mortgage ($21,369) + Fees ($1,224) + Taxes in 2025 ($1,918)


    Taxes:$23,020

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2 CHASE RD, WINDERMERE, FL 34786

    $3,200,000265 Days on yellowkey   MLS ID: O6345197

    For Sale O6345197 - 2 CHASE RD, WINDERMERE, FL 34786 3 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3889
       Built: 2026   Tax: $3,100 (2024)
    Community: Windermere
    Single Family


    Estimated Monthly Payment: $17,792 (change assumption)
    Mortgage ($17,534) + Taxes in 2024 ($258)


    Taxes:$3,100

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9721 CARILLON PARK DR, WINDERMERE, FL 34786

    $5,000,000295 Days on yellowkey   MLS ID: O6336879

    For Sale O6336879 - 9721 CARILLON PARK DR, WINDERMERE, FL 34786 81 photos

    Bed: 6   Bath: 8.0   Gar: 4
    Liv Area Sq Ft: 8305
       Built: 2011
    Monthly Fee: $283
       Tax: $47,936 (2023)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,674 (change assumption)
    Mortgage ($27,397) + Fees ($283) + Taxes in 2023 ($3,995)


    Taxes:$47,936

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2023

    Middle School: Bridgewater Middle


  • 4029 ISABELLA CIR, WINDERMERE, FL 34786

    $3,299,00054 Days on yellowkey   MLS ID: O6400064

    0 Days Off yellowkey (back on 5/4/2026)

    For Sale O6400064 - 4029 ISABELLA CIR, WINDERMERE, FL 34786 98 photos

    Bed: 6   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 7217
       Built: 2018
    Monthly Fee: $480
       Tax: $30,300 (2025)
    Community: Casabella
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,081 (change assumption)
    Mortgage ($18,076) + Fees ($480) + Taxes in 2025 ($2,525)


    Taxes:$30,300

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 4301 DOWN POINT LN, WINDERMERE, FL 34786

    $2,950,00059 Days on yellowkey   MLS ID: O6398366

    For Sale O6398366 - 4301 DOWN POINT LN, WINDERMERE, FL 34786 61 photos

    Bed: 5   Bath: 4.0   Gar: 6
    Liv Area Sq Ft: 7153
       Built: 1983   Tax: $19,012 (2025)
    Community: Down Point Sub
    Single Family


    Estimated Monthly Payment: $17,748 (change assumption)
    Mortgage ($16,164) + Taxes in 2025 ($1,584)


    Taxes:$19,012

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 9940 GROSVENOR POINTE CIR, WINDERMERE, FL 34786

    $3,195,000120 Days on yellowkey   MLS ID: O6380812

    1 Days Off yellowkey (back on 5/2/2026)

    For Sale O6380812 - 9940 GROSVENOR POINTE CIR, WINDERMERE, FL 34786 50 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 5071
       Built: 2014
    Monthly Fee: $283
       Tax: $29,036 (2024)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $20,209 (change assumption)
    Mortgage ($17,506) + Fees ($283) + Taxes in 2024 ($2,420)


    Taxes:$29,036

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786

    $6,000,000158 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 61 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


  • 5036 LATROBE DR, WINDERMERE, FL 34786

    $4,900,000249 Days on yellowkey   MLS ID: O6346003

    1 Days Off yellowkey (back on 3/28/2026)

    For Sale O6346003 - 5036 LATROBE DR, WINDERMERE, FL 34786 47 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5548
       Built: 1990
    Monthly Fee: $1,224
       Tax: $17,326 (2024)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $29,516 (change assumption)
    Mortgage ($26,849) + Fees ($1,224) + Taxes in 2024 ($1,444)


    Taxes:$17,326

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9639 WESTOVER ROBERTS RD, WINDERMERE, FL 34786

    $5,900,000274 Days on yellowkey   MLS ID: O6341883

    REDUCED by $495,000 (7.7%) on 04/28/2026

    For Sale O6341883 - 9639 WESTOVER ROBERTS RD, WINDERMERE, FL 34786 78 photos

    Bed: 5   Bath: 8.5   Gar: 7
    Liv Area Sq Ft: 11861
       Built: 2017   Tax: $50,738 (2024)
    Community: Gotha Town
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $36,556 (change assumption)
    Mortgage ($32,328) + Taxes in 2024 ($4,228)


    Taxes:$50,738

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 17538 BLACK RAIL ST, WINDERMERE, FL 34786

    $1,390,000249 Days on yellowkey   MLS ID: O6349325

    For Sale O6349325 - 17538 BLACK RAIL ST, WINDERMERE, FL 34786 32 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4522
       Built: 2014
    Monthly Fee: $167
       Tax: $16,404 (2024)
    Community: Enclave
    Single Family


    Estimated Monthly Payment: $9,150 (change assumption)
    Mortgage ($7,616) + Fees ($167) + Taxes in 2024 ($1,367)


    Taxes:$16,404

    Elementary School: None

    High School: Windermere High School

    Tax Year: 2024

    Middle School: None


  • 9259 TIBET POINTE CIR, WINDERMERE, FL 34786

    $6,499,000378 Days on yellowkey   MLS ID: O6312645

    2 Days Off yellowkey (back on 4/26/2026)

    For Sale O6312645 - 9259 TIBET POINTE CIR, WINDERMERE, FL 34786 70 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 6257
       Built: 2007
    Monthly Fee: $298
       Tax: $35,727 (2024)
    Community: Keenes Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $38,885 (change assumption)
    Mortgage ($35,610) + Fees ($298) + Taxes in 2024 ($2,977)


    Taxes:$35,727

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 6149 GROSVENOR SHORE DR, WINDERMERE, FL 34786

    $10,900,000211 Days on yellowkey   MLS ID: O6356355

    For Sale O6356355 - 6149 GROSVENOR SHORE DR, WINDERMERE, FL 34786 75 photos

    Bed: 6   Bath: 7.0   Gar: 7
    Liv Area Sq Ft: 6783
       Built: 2013
    Monthly Fee: $298
       Tax: $57,807 (2023)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $64,840 (change assumption)
    Mortgage ($59,725) + Fees ($298) + Taxes in 2023 ($4,817)


    Taxes:$57,807

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2023

    Middle School: Bridgewater Middle






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.