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Windermere Homes For Sale & Real Estate - 275 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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  • 414 E 5TH AVE, WINDERMERE, FL 34786

    $1,200,00042 Days on yellowkey   MLS ID: O6387808

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

    For Sale O6387808 - 414 E 5TH AVE, WINDERMERE, FL 34786 77 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2521
       Built: 2000   Tax: $7,227 (2024)
    Community: Windermere Rep
    Single Family


    Estimated Monthly Payment: $7,177 (change assumption)
    Mortgage ($6,575) + Taxes in 2024 ($602)


    Taxes:$7,227

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 6953 TETTENHALL LN, WINDERMERE, FL 34786

    $605,00012 Days on yellowkey   MLS ID: O6396363

    For Sale O6396363 - 6953 TETTENHALL LN, WINDERMERE, FL 34786 61 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2452
       Built: 2007
    Monthly Fee: $82
       Tax: $8,337 (2026)
    Community: Lakes/Windermere Ph 04
    Single Family


    Estimated Monthly Payment: $4,092 (change assumption)
    Mortgage ($3,315) + Fees ($82) + Taxes in 2026 ($695)


    Taxes:$8,337

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 13263 STRODE LN, WINDERMERE, FL 34786

    $798,90058 Days on yellowkey   MLS ID: O6383141

    For Sale O6383141 - 13263 STRODE LN, WINDERMERE, FL 34786 53 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2559
       Built: 2008
    Monthly Fee: $86
       Tax: $8,367 (2024)
    Community: Berkshire Park
    Single Family


    Estimated Monthly Payment: $5,161 (change assumption)
    Mortgage ($4,377) + Fees ($86) + Taxes in 2024 ($697)


    Taxes:$8,367

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 5074 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786

    $7,595,00092 Days on yellowkey   MLS ID: O6373191

    For Sale O6373191 - 5074 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786 83 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 6937
       Built: 1988
    Monthly Fee: $1,043
       Tax: $21,279 (2024)
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $44,432 (change assumption)
    Mortgage ($41,615) + Fees ($1,043) + Taxes in 2024 ($1,773)


    Taxes:$21,279

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12936 DROXFORD RD, WINDERMERE, FL 34786

    $670,00076 Days on yellowkey   MLS ID: O6376097

    INCREASED by $21,000 (3.2%) on 04/01/2026

    For Sale O6376097 - 12936 DROXFORD RD, WINDERMERE, FL 34786 29 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2960
       Built: 2006
    Monthly Fee: $82
       Tax: $9,928 (2024)
    Community: Lakes/Windermere Ph 02A
    Single Family


    Estimated Monthly Payment: $4,580 (change assumption)
    Mortgage ($3,671) + Fees ($82) + Taxes in 2024 ($827)


    Taxes:$9,928

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13712 SUMMERPORT VILLAGE PKWY, WINDERMERE, FL 34786

    $444,90066 Days on yellowkey   MLS ID: S5143431

    For Sale S5143431 - 13712 SUMMERPORT VILLAGE PKWY, WINDERMERE, FL 34786 64 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1997
       Built: 2019
    Monthly Fee: $171
       Tax: $5,448 (2025)
    Community: Vineyards/Horizons West Ph 4
    Townhouse


    Estimated Monthly Payment: $3,063 (change assumption)
    Mortgage ($2,438) + Fees ($171) + Taxes in 2025 ($454)


    Taxes:$5,448

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13858 CAYWOOD POND DR, WINDERMERE, FL 34786

    $963,00051 Days on yellowkey   MLS ID: O6382987

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

    For Sale O6382987 - 13858 CAYWOOD POND DR, WINDERMERE, FL 34786 54 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3070
       Built: 2004
    Monthly Fee: $130
       Tax: $12,050 (2025)
    Community: Summerport Ph 1
    Single Family


    Estimated Monthly Payment: $6,411 (change assumption)
    Mortgage ($5,277) + Fees ($130) + Taxes in 2025 ($1,004)


    Taxes:$12,050

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12132 MONTALCINO CIR, WINDERMERE, FL 34786

    $3,950,000162 Days on yellowkey   MLS ID: O6319854

    For Sale O6319854 - 12132 MONTALCINO CIR, WINDERMERE, FL 34786 91 photos

    Bed: 6   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 5709
       Built: 2016
    Monthly Fee: $242
       Tax: $38,798 (2024)
    Community: Casa Del Lago Rep
    Single Family


    Estimated Monthly Payment: $25,118 (change assumption)
    Mortgage ($21,643) + Fees ($242) + Taxes in 2024 ($3,233)


    Taxes:$38,798

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 11455 CLAYMONT CIR, WINDERMERE, FL 34786

    $1,249,00012 Days on yellowkey   MLS ID: O6396381

    For Sale O6396381 - 11455 CLAYMONT CIR, WINDERMERE, FL 34786 36 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2262
       Built: 2003
    Monthly Fee: $298
       Tax: $7,673 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $7,781 (change assumption)
    Mortgage ($6,844) + Fees ($298) + Taxes in 2025 ($639)


    Taxes:$7,673

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9237 SABAL PALM CIR, WINDERMERE, FL 34786

    $789,99512 Days on yellowkey   MLS ID: G5110005

    For Sale G5110005 - 9237 SABAL PALM CIR, WINDERMERE, FL 34786 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2469
       Built: 1985
    Monthly Fee: $32
       Tax: $3,444 (2025)
    Community: Silver Woods Ph 01
    Single Family


    Estimated Monthly Payment: $4,648 (change assumption)
    Mortgage ($4,329) + Fees ($32) + Taxes in 2025 ($287)


    Taxes:$3,444

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1002 DOWN RESERVE CT, WINDERMERE, FL 34786

    $6,490,00054 Days on yellowkey   MLS ID: O6383597

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

    For Sale O6383597 - 1002 DOWN RESERVE CT, WINDERMERE, FL 34786 30 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6706
       Built: 2021
    Monthly Fee: $433
       Tax: $61,838 (2024)
    Community: Rosser Reserve Rep
    Single Family


    Estimated Monthly Payment: $41,147 (change assumption)
    Mortgage ($35,561) + Fees ($433) + Taxes in 2024 ($5,153)


    Taxes:$61,838

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 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




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.