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Windermere Homes For Sale & Real Estate - 281 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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  • 13013 OVERSTREET RD, WINDERMERE, FL 34786

    $679,99449 Days on yellowkey   MLS ID: O6380917

    For Sale O6380917 - 13013 OVERSTREET RD, WINDERMERE, FL 34786 47 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2053
       Built: 2009
    Monthly Fee: $82
       Tax: $3,146 (2024)
    Community: Lakes/Windermere
    Single Family


    Estimated Monthly Payment: $4,070 (change assumption)
    Mortgage ($3,726) + Fees ($82) + Taxes in 2024 ($262)


    Taxes:$3,146

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 4 CHASE RD, WINDERMERE, FL 34786

    $900,00055 Days on yellowkey   MLS ID: O6384257

    For Sale O6384257 - 4 CHASE RD, WINDERMERE, FL 34786 47 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 2386
       Built: 1971   Tax: $7,637 (2024)
    Community: Windermere Town
    Single Family


    Estimated Monthly Payment: $5,568 (change assumption)
    Mortgage ($4,931) + Taxes in 2024 ($636)


    Taxes:$7,637

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11835 GOLD CREEK TRL, WINDERMERE, FL 34786

    $900,00063 Days on yellowkey   MLS ID: O6382068

    For Sale O6382068 - 11835 GOLD CREEK TRL, WINDERMERE, FL 34786 11 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3119
       Built: 2012
    Monthly Fee: $75
       Tax: $9,395 (2024)
    Community: Windermere Trls Ph 1A
    Single Family


    Estimated Monthly Payment: $5,789 (change assumption)
    Mortgage ($4,931) + Fees ($75) + Taxes in 2024 ($783)


    Taxes:$9,395

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13421 BONICA WAY, WINDERMERE, FL 34786

    $1,369,99927 Days on yellowkey   MLS ID: O6392381

    For Sale O6392381 - 13421 BONICA WAY, WINDERMERE, FL 34786 48 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4869
       Built: 2005
    Monthly Fee: $317
       Tax: $19,939 (2025)
    Community: Tildens Grove Ph 02
    Single Family


    Estimated Monthly Payment: $9,485 (change assumption)
    Mortgage ($7,507) + Fees ($317) + Taxes in 2025 ($1,662)


    Taxes:$19,939

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8375 BOWDEN WAY, WINDERMERE, FL 34786

    $1,369,000171 Days on yellowkey   MLS ID: S5137385

    1 Days Off yellowkey (back on 4/4/2026)

    REDUCED by $1,000 (0.1%) on 03/31/2026

    For Sale S5137385 - 8375 BOWDEN WAY, WINDERMERE, FL 34786 68 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3809
       Built: 1999
    Monthly Fee: $283
       Tax: $9,709 (2025)
    Community: Keenes Pointe Unit 1
    Single Family


    Estimated Monthly Payment: $8,593 (change assumption)
    Mortgage ($7,501) + Fees ($283) + Taxes in 2025 ($809)


    Taxes:$9,709

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 3138 SEIGNEURY DR, WINDERMERE, FL 34786

    $1,350,00037 Days on yellowkey   MLS ID: O6387397

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

    For Sale O6387397 - 3138 SEIGNEURY DR, WINDERMERE, FL 34786 28 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3831
       Built: 1997
    Monthly Fee: $250
       Tax: $11,794 (2024)
    Community: Harbor Isle
    Single Family


    Estimated Monthly Payment: $8,630 (change assumption)
    Mortgage ($7,397) + Fees ($250) + Taxes in 2024 ($983)


    Taxes:$11,794

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 14217 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786

    $600,00013 Days on yellowkey   MLS ID: O6396155

    For Sale O6396155 - 14217  BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2419
       Built: 2006
    Monthly Fee: $131
       Tax: $8,205 (2026)
    Community: Summerport
    Single Family


    Estimated Monthly Payment: $4,102 (change assumption)
    Mortgage ($3,288) + Fees ($131) + Taxes in 2026 ($684)


    Taxes:$8,205

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 8533 GREENBANK BLVD, WINDERMERE, FL 34786

    $550,000176 Days on yellowkey   MLS ID: O6354672

    0 Days Off yellowkey (back on 4/3/2026)

    For Sale O6354672 - 8533 GREENBANK BLVD, WINDERMERE, FL 34786 22 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2551
       Built: 2004
    Monthly Fee: $176
       Tax: $3,300 (2024)
    Community: Lakes/Windermere-Peachtree
    Single Family


    Estimated Monthly Payment: $3,465 (change assumption)
    Mortgage ($3,014) + Fees ($176) + Taxes in 2024 ($275)


    Taxes:$3,300

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9323 GLADYS GARDEN CT, WINDERMERE, FL 34786

    $12,500,00062 Days on yellowkey   MLS ID: O6381880

    REDUCED by $1,495,000 (10.7%) on 04/03/2026

    For Sale O6381880 - 9323 GLADYS GARDEN CT, WINDERMERE, FL 34786 84 photos

    Bed: 6   Bath: 8.0   Gar: 4
    Liv Area Sq Ft: 9770
       Built: 2026
    Monthly Fee: $1,099
       Tax: $21,279 (2025)
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $71,364 (change assumption)
    Mortgage ($68,491) + Fees ($1,099) + Taxes in 2025 ($1,773)


    Taxes:$21,279

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 8256 MARITIME FLAG ST #103| 1710, WINDERMERE, FL 34786

    $338,49023 Days on yellowkey   MLS ID: O6393278

    0 Days Off yellowkey (back on 4/1/2026)

    For Sale O6393278 - 8256 MARITIME FLAG ST #103| 1710, WINDERMERE, FL 34786 32 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1442
       Built: 2009   Tax: $1,540 (2024)
    Community: Lakeside/Lks/Windermere Ph 17
    Condo


    Estimated Monthly Payment: $1,983 (change assumption)
    Mortgage ($1,855) + Taxes in 2024 ($128)


    Taxes:$1,540

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 5130 SUN PALM DR, WINDERMERE, FL 34786

    $525,00014 Days on yellowkey   MLS ID: O6390875

    For Sale O6390875 - 5130 SUN PALM DR, WINDERMERE, FL 34786 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1723
       Built: 1987
    Monthly Fee: $30
       Tax: $8,032 (2025)
    Community: Silver Woods Ph 04
    Single Family


    Estimated Monthly Payment: $3,576 (change assumption)
    Mortgage ($2,877) + Fees ($30) + Taxes in 2025 ($669)


    Taxes:$8,032

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 12305 VIA DERNA PL, WINDERMERE, FL 34786

    $470,00086 Days on yellowkey   MLS ID: O6374964

    For Sale O6374964 - 12305 VIA DERNA PL, WINDERMERE, FL 34786 24 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1891
       Built: 2014
    Monthly Fee: $316
       Tax: $5,016 (2025)
    Community: Carrington
    Townhouse


    Estimated Monthly Payment: $3,309 (change assumption)
    Mortgage ($2,575) + Fees ($316) + Taxes in 2025 ($418)


    Taxes:$5,016

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6712 THORNHILL CIR, WINDERMERE, FL 34786

    $680,000185 Days on yellowkey   MLS ID: O6351284

    For Sale O6351284 - 6712 THORNHILL CIR, WINDERMERE, FL 34786 50 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2976
       Built: 2002
    Monthly Fee: $80
       Tax: $4,096 (2024)
    Community: Lakes Windermere Ph 01 49 108
    Single Family


    Estimated Monthly Payment: $4,147 (change assumption)
    Mortgage ($3,726) + Fees ($80) + Taxes in 2024 ($341)


    Taxes:$4,096

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786

    $325,00091 Days on yellowkey   MLS ID: TB8465266

    For Sale TB8465266 - 8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786 70 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1442
       Built: 2006   Tax: $4,422 (2024)
    Community: Lakeside/Lks/Windermere Ph 3
    Condo


    Estimated Monthly Payment: $2,149 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($368)


    Taxes:$4,422

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11450 ARBORSIDE BEND WAY, WINDERMERE, FL 34786

    $749,901176 Days on yellowkey   MLS ID: O6354816

    For Sale O6354816 - 11450 ARBORSIDE BEND WAY, WINDERMERE, FL 34786 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2622
       Built: 2002
    Monthly Fee: $170
       Tax: $4,856 (2024)
    Community: Glenmuir 48 39
    Single Family


    Estimated Monthly Payment: $4,684 (change assumption)
    Mortgage ($4,109) + Fees ($170) + Taxes in 2024 ($405)


    Taxes:$4,856

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 6110 KEENES POINTE DR, WINDERMERE, FL 34786

    $1,900,00014 Days on yellowkey   MLS ID: O6393573

    For Sale O6393573 - 6110 KEENES POINTE DR, WINDERMERE, FL 34786 78 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3196
       Built: 2002
    Monthly Fee: $298
       Tax: $10,956 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $11,622 (change assumption)
    Mortgage ($10,411) + Fees ($298) + Taxes in 2025 ($913)


    Taxes:$10,956

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 7719 ANSELMO LN, WINDERMERE, FL 34786

    $387,50023 Days on yellowkey   MLS ID: O6392007

    For Sale O6392007 - 7719 ANSELMO LN, WINDERMERE, FL 34786 31 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1644
       Built: 2008
    Monthly Fee: $375
       Tax: $5,537 (2025)
    Community: Lake Sawyer South Ph 03
    Townhouse


    Estimated Monthly Payment: $2,960 (change assumption)
    Mortgage ($2,123) + Fees ($375) + Taxes in 2025 ($461)


    Taxes:$5,537

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13411 LEMON ORCHARD BND, WINDERMERE, FL 34786

    $562,09514 Days on yellowkey   MLS ID: TB8493546

    For Sale TB8493546 - 13411 LEMON ORCHARD BND, WINDERMERE, FL 34786 2 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1649
       Built: 2026
    Monthly Fee: $280
       Tax: $8,670 (2026)
    Community: Lake Cawood Cove
    Townhouse


    Estimated Monthly Payment: $4,082 (change assumption)
    Mortgage ($3,080) + Fees ($280) + Taxes in 2026 ($723)


    Taxes:$8,670

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 6288 BLAKEFORD DR, WINDERMERE, FL 34786

    $2,600,000148 Days on yellowkey   MLS ID: O6361679

    For Sale O6361679 - 6288 BLAKEFORD DR, WINDERMERE, FL 34786 90 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5366
       Built: 2003
    Monthly Fee: $283
       Tax: $34,766 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $17,426 (change assumption)
    Mortgage ($14,246) + Fees ($283) + Taxes in 2025 ($2,897)


    Taxes:$34,766

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11531 VICOLO LOOP, WINDERMERE, FL 34786

    $600,00088 Days on yellowkey   MLS ID: O6374016

    REDUCED by $25,000 (4.0%) on 04/03/2026

    For Sale O6374016 - 11531 VICOLO LOOP, WINDERMERE, FL 34786 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2280
       Built: 2003
    Monthly Fee: $122
       Tax: $8,726 (2025)
    Community: Belmere Village
    Single Family


    Estimated Monthly Payment: $4,137 (change assumption)
    Mortgage ($3,288) + Fees ($122) + Taxes in 2025 ($727)


    Taxes:$8,726

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle




Why Bother Searching Elsewhere for Windermere Homes for Sale and Other Real Estate?

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.