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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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  • 13013 OVERSTREET RD, WINDERMERE, FL 34786

    $639,994140 Days on yellowkey   MLS ID: O6380917

    REDUCED by $10,000 (1.5%) on 06/17/2026

    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
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,851 (change assumption)
    Mortgage ($3,507) + 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


  • 6124 FOXFIELD CT, WINDERMERE, FL 34786

    $1,295,00023 Days on yellowkey   MLS ID: O6419393

    For Sale O6419393 - 6124 FOXFIELD CT, WINDERMERE, FL 34786 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2887
       Built: 2001
    Monthly Fee: $298
       Tax: $8,717 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $8,120 (change assumption)
    Mortgage ($7,096) + Fees ($298) + Taxes in 2025 ($726)


    Taxes:$8,717

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13525 GORGONA ISLE DR, WINDERMERE, FL 34786

    $1,095,000150 Days on yellowkey   MLS ID: O6377789

    REDUCED by $3,000 (0.3%) on 07/11/2026

    For Sale O6377789 - 13525 GORGONA ISLE DR, WINDERMERE, FL 34786 39 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4625
       Built: 2018
    Monthly Fee: $268
       Tax: $9,351 (2025)
    Community: Windermere Isle
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,047 (change assumption)
    Mortgage ($6,000) + Fees ($268) + Taxes in 2025 ($779)


    Taxes:$9,351

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2630 STANTON HALL CT, WINDERMERE, FL 34786

    $899,99917 Days on yellowkey   MLS ID: O6420386

    For Sale O6420386 - 2630 STANTON HALL CT, WINDERMERE, FL 34786 10 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2258
       Built: 1988
    Monthly Fee: $60
       Tax: $10,084 (2025)
    Community: Manors At Butler Bay Ph 01
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,832 (change assumption)
    Mortgage ($4,931) + Fees ($60) + Taxes in 2025 ($840)


    Taxes:$10,084

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 13542 GORGONA ISLE DR, WINDERMERE, FL 34786

    $895,000125 Days on yellowkey   MLS ID: O6390582

    REDUCED by $55,000 (5.8%) on 04/25/2026

    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: $5,985 (change assumption)
    Mortgage ($4,904) + 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


  • 13450 SUNKISS LOOP, WINDERMERE, FL 34786

    $564,90050 Days on yellowkey   MLS ID: O6407409

    REDUCED by $5,000 (0.9%) on 07/10/2026

    For Sale O6407409 - 13450 SUNKISS LOOP, WINDERMERE, FL 34786 16 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2272
       Built: 2005
    Monthly Fee: $131
       Tax: $8,219 (2025)
    Community: Summerport Ph 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,911 (change assumption)
    Mortgage ($3,095) + Fees ($131) + Taxes in 2025 ($685)


    Taxes:$8,219

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9648 WEATHERSTONE CT, WINDERMERE, FL 34786

    $2,450,00087 Days on yellowkey   MLS ID: O6400680

    REDUCED by $50,000 (2.0%) on 07/12/2026

    For Sale O6400680 - 9648 WEATHERSTONE CT, WINDERMERE, FL 34786 65 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4482
       Built: 2000
    Monthly Fee: $227
       Tax: $20,450 (2025)
    Community: Weatherstone On Lake Olivia
    Spa: No

    Single Family


    Estimated Monthly Payment: $15,355 (change assumption)
    Mortgage ($13,424) + Fees ($227) + Taxes in 2025 ($1,704)


    Taxes:$20,450

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 14353 CREST PALM AVE, WINDERMERE, FL 34786

    $1,039,09182 Days on yellowkey   MLS ID: G5111542

    For Sale G5111542 - 14353 CREST PALM AVE, WINDERMERE, FL 34786 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $245
       Tax: $1,309 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,048 (change assumption)
    Mortgage ($5,694) + Fees ($245) + Taxes in 2025 ($109)


    Taxes:$1,309

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11994 MCKINNON RD, WINDERMERE, FL 34786

    $849,90034 Days on yellowkey   MLS ID: O6416526

    For Sale O6416526 - 11994 MCKINNON RD, WINDERMERE, FL 34786 56 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2450
       Built: 2004   Tax: $4,163 (2025)
    Community: N/A
    Single Family


    Estimated Monthly Payment: $5,004 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($347)


    Taxes:$4,163

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6752 TRELLIS VINE LOOP, WINDERMERE, FL 34786

    $930,000174 Days on yellowkey   MLS ID: O6376318

    REDUCED by $40,000 (4.1%) on 04/30/2026

    For Sale O6376318 - 6752 TRELLIS VINE LOOP, WINDERMERE, FL 34786 22 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3820
       Built: 2018
    Monthly Fee: $200
       Tax: $10,983 (2024)
    Community: Windstone
    Single Family


    Estimated Monthly Payment: $6,211 (change assumption)
    Mortgage ($5,096) + Fees ($200) + Taxes in 2024 ($915)


    Taxes:$10,983

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 11413 CAMDEN PARK DR, WINDERMERE, FL 34786

    $1,395,00029 Days on yellowkey   MLS ID: O6417791

    0 Days Off yellowkey (back on 6/17/2026)

    For Sale O6417791 - 11413 CAMDEN PARK DR, WINDERMERE, FL 34786 65 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3840
       Built: 2005
    Monthly Fee: $298
       Tax: $14,973 (2025)
    Community: Keene's Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,189 (change assumption)
    Mortgage ($7,644) + Fees ($298) + Taxes in 2025 ($1,248)


    Taxes:$14,973

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 17538 BLACK RAIL ST, WINDERMERE, FL 34786

    $1,380,000286 Days on yellowkey   MLS ID: O6349325

    REDUCED by $10,000 (0.7%) on 07/11/2026

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

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4999
       Built: 2014
    Monthly Fee: $167
       Tax: $16,404 (2024)
    Community: Enclave
    Single Family


    Estimated Monthly Payment: $9,095 (change assumption)
    Mortgage ($7,561) + Fees ($167) + Taxes in 2024 ($1,367)


    Taxes:$16,404

    Elementary School: None

    High School: Windermere High School

    Tax Year: 2024

    Middle School: None


  • 2053 WOODY DR, WINDERMERE, FL 34786

    $679,00013 Days on yellowkey   MLS ID: O6421738

    For Sale O6421738 - 2053 WOODY DR, WINDERMERE, FL 34786 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2177
       Built: 1973
    Monthly Fee: $88
       Tax: $4,023 (2025)
    Community: Windermere Downs
    Single Family


    Estimated Monthly Payment: $4,144 (change assumption)
    Mortgage ($3,720) + Fees ($88) + Taxes in 2025 ($335)


    Taxes:$4,023

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 4718 BLUE MAJOR DR, WINDERMERE, FL 34786

    $500,00043 Days on yellowkey   MLS ID: O6410820

    REDUCED by $20,000 (3.8%) on 07/10/2026

    For Sale O6410820 - 4718 BLUE MAJOR DR, WINDERMERE, FL 34786 61 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1911
       Built: 2005
    Monthly Fee: $143
       Tax: $7,296 (2025)
    Community: Summerport Ph 05
    Single Family


    Estimated Monthly Payment: $3,491 (change assumption)
    Mortgage ($2,740) + Fees ($143) + Taxes in 2025 ($608)


    Taxes:$7,296

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11536 CLAYMONT CIR, WINDERMERE, FL 34786

    $1,175,000112 Days on yellowkey   MLS ID: O6392958

    1 Days Off yellowkey (back on 7/12/2026)

    REDUCED by $75,000 (6.0%) on 05/26/2026

    For Sale O6392958 - 11536 CLAYMONT CIR, WINDERMERE, FL 34786 68 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2882
       Built: 2002
    Monthly Fee: $298
       Tax: $8,766 (2025)
    Community: Keenes Pointe Ut 04 Sec 31 48 82
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,467 (change assumption)
    Mortgage ($6,438) + Fees ($298) + Taxes in 2025 ($731)


    Taxes:$8,766

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11217 WILLOW GARDENS DR, WINDERMERE, FL 34786

    $1,075,00019 Days on yellowkey   MLS ID: O6417903

    REDUCED by $95,000 (8.1%) on 07/07/2026

    For Sale O6417903 - 11217 WILLOW GARDENS DR, WINDERMERE, FL 34786 51 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2824
       Built: 1994
    Monthly Fee: $122
       Tax: $13,562 (2026)
    Community: Willows At Lake Rhea
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,142 (change assumption)
    Mortgage ($5,890) + Fees ($122) + Taxes in 2026 ($1,130)


    Taxes:$13,562

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Bridgewater Middle


  • 1629 HEMPEL AVE, WINDERMERE, FL 34786

    $2,500,0005 Days on yellowkey   MLS ID: O6418226

    For Sale O6418226 - 1629 HEMPEL AVE, WINDERMERE, FL 34786 89 photos

    Bed: 6   Bath: 4.0
    Liv Area Sq Ft: 4858
       Built: 1979   Tax: $10,219 (2025)
    Community: Gotha Town
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,550 (change assumption)
    Mortgage ($13,698) + Taxes in 2025 ($852)


    Taxes:$10,219

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786

    $2,399,000300 Days on yellowkey   MLS ID: O6344907

    REDUCED by $100,000 (4.0%) on 05/29/2026

    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: $14,852 (change assumption)
    Mortgage ($13,145) + 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


  • 14422 CREST PALM AVE, WINDERMERE, FL 34786

    $1,100,00026 Days on yellowkey   MLS ID: O6418503

    For Sale O6418503 - 14422 CREST PALM AVE, WINDERMERE, FL 34786 30 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3140
       Built: 2025
    Monthly Fee: $245
       Tax: $2,889 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,513 (change assumption)
    Mortgage ($6,027) + Fees ($245) + Taxes in 2025 ($241)


    Taxes:$2,889

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 9433 PALM TREE DR, WINDERMERE, FL 34786

    $560,0007 Days on yellowkey   MLS ID: O6423262

    For Sale O6423262 - 9433 PALM TREE DR, WINDERMERE, FL 34786 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1819
       Built: 1986
    Monthly Fee: $32
       Tax: $7,836 (2025)
    Community: Silver Woods Ph 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,753 (change assumption)
    Mortgage ($3,068) + Fees ($32) + Taxes in 2025 ($653)


    Taxes:$7,836

    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.