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Windermere Single Family Homes For Sale - 282 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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  • 1700 LAKE ROBERTS CT, WINDERMERE, FL 34786

    $1,450,00023 Days on yellowkey   MLS ID: O6410847

    For Sale O6410847 - 1700 LAKE ROBERTS CT, WINDERMERE, FL 34786 47 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3929
       Built: 2002
    Monthly Fee: $216
       Tax: $10,637 (2025)
    Community: Butler Bay,Windermere Club
    Single Family


    Estimated Monthly Payment: $9,047 (change assumption)
    Mortgage ($7,945) + Fees ($216) + Taxes in 2025 ($886)


    Taxes:$10,637

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 2 CHASE RD, WINDERMERE, FL 34786

    $2,200,000274 Days on yellowkey   MLS ID: O6345197

    REDUCED by $1,000,000 (31.3%) on 06/16/2026

    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: $12,313 (change assumption)
    Mortgage ($12,054) + Taxes in 2024 ($258)


    Taxes:$3,100

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 2503 BUTLER BAY DR N, WINDERMERE, FL 34786

    $1,799,00015 Days on yellowkey   MLS ID: O6413242

    For Sale O6413242 - 2503 BUTLER BAY DR N, WINDERMERE, FL 34786 98 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3297
       Built: 1990
    Monthly Fee: $199
       Tax: $16,376 (2025)
    Community: Windermere Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,421 (change assumption)
    Mortgage ($9,857) + Fees ($199) + Taxes in 2025 ($1,365)


    Taxes:$16,376

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11536 CLAYMONT CIR, WINDERMERE, FL 34786

    $1,175,00084 Days on yellowkey   MLS ID: O6392958

    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


  • 9312 BLANCHE COVE DR, WINDERMERE, FL 34786

    $12,350,00017 Days on yellowkey   MLS ID: O6407102

    For Sale O6407102 - 9312 BLANCHE COVE DR, WINDERMERE, FL 34786 96 photos

    Bed: 7   Bath: 9.5   Gar: 4
    Liv Area Sq Ft: 11465
       Built: 2022
    Monthly Fee: $1,224
       Tax: $116,012 (2025)
    Community: Isleworth 5Th Amd
    Spa: No

    Single Family


    Estimated Monthly Payment: $78,561 (change assumption)
    Mortgage ($67,670) + Fees ($1,224) + Taxes in 2025 ($9,668)


    Taxes:$116,012

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 9832 LAUREL VALLEY DR, WINDERMERE, FL 34786

    $13,900,0007 Days on yellowkey   MLS ID: O6416194

    For Sale O6416194 - 9832 LAUREL VALLEY DR, WINDERMERE, FL 34786 97 photos

    Bed: 6   Bath: 8.5   Gar: 4
    Liv Area Sq Ft: 11100
       Built: 2004
    Monthly Fee: $1,167
       Tax: $93,184 (2025)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $85,095 (change assumption)
    Mortgage ($76,162) + Fees ($1,167) + Taxes in 2025 ($7,765)


    Taxes:$93,184

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12720 JACOB GRACE CT, WINDERMERE, FL 34786

    $2,750,000105 Days on yellowkey   MLS ID: TB8476930

    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


  • 5500 W LAKE BUTLER RD, WINDERMERE, FL 34786

    $4,700,00031 Days on yellowkey   MLS ID: O6408637

    0 Days Off yellowkey (back on 6/9/2026)

    For Sale O6408637 - 5500 W LAKE BUTLER RD, WINDERMERE, FL 34786 97 photos

    Bed: 8   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 7000
       Built: 1997   Tax: $17,387 (2025)
    Community: West Lake Butler Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,202 (change assumption)
    Mortgage ($25,753) + Taxes in 2025 ($1,449)


    Taxes:$17,387

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6558 HELMSLEY CIR, WINDERMERE, FL 34786

    $635,0007 Days on yellowkey   MLS ID: S5151342

    For Sale S5151342 - 6558 HELMSLEY CIR, WINDERMERE, FL 34786 55 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2575
       Built: 2009
    Monthly Fee: $129
       Tax: $4,553 (2025)
    Community: Preston Square
    Single Family


    Estimated Monthly Payment: $3,988 (change assumption)
    Mortgage ($3,479) + Fees ($129) + Taxes in 2025 ($379)


    Taxes:$4,553

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9620 MAYWOOD DR, WINDERMERE, FL 34786

    $2,349,00064 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


  • 11486 MISTY OAK ALY, WINDERMERE, FL 34786

    $549,00058 Days on yellowkey   MLS ID: S5148331

    3 Days Off yellowkey (back on 5/18/2026)

    For Sale S5148331 - 11486 MISTY OAK ALY, WINDERMERE, FL 34786 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 2016
    Monthly Fee: $107
       Tax: $7,492 (2025)
    Community: Ashlin Park Ph 1
    Single Family


    Estimated Monthly Payment: $3,739 (change assumption)
    Mortgage ($3,008) + Fees ($107) + Taxes in 2025 ($624)


    Taxes:$7,492

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11539 LAKE BUTLER BLVD, WINDERMERE, FL 34786

    $3,800,0003 Days on yellowkey   MLS ID: O6416913

    For Sale O6416913 - 11539 LAKE BUTLER BLVD, WINDERMERE, FL 34786 80 photos

    Bed: 5   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 5018
       Built: 2017   Tax: $14,654 (2025)
    Community: Lake Butler Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $22,043 (change assumption)
    Mortgage ($20,821) + Taxes in 2025 ($1,221)


    Taxes:$14,654

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 6648 HELSTON LN, WINDERMERE, FL 34786

    $665,0003 Days on yellowkey   MLS ID: O6413354

    For Sale O6413354 - 6648 HELSTON LN, WINDERMERE, FL 34786 47 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3072
       Built: 2005
    Monthly Fee: $82
       Tax: $9,709 (2025)
    Community: Lakes/Windermere Ph 02A
    Single Family


    Estimated Monthly Payment: $4,535 (change assumption)
    Mortgage ($3,644) + Fees ($82) + Taxes in 2025 ($809)


    Taxes:$9,709

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6897 NORTHWICH DR, WINDERMERE, FL 34786

    $574,90057 Days on yellowkey   MLS ID: O6400673

    0 Days Off yellowkey (back on 5/18/2026)

    REDUCED by $5,000 (0.9%) on 05/13/2026

    For Sale O6400673 - 6897 NORTHWICH DR, WINDERMERE, FL 34786 31 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2229
       Built: 2003
    Monthly Fee: $82
       Tax: $7,925 (2025)
    Community: Lakes Windermere Ph 01 49 108
    Single Family


    Estimated Monthly Payment: $3,892 (change assumption)
    Mortgage ($3,150) + Fees ($82) + Taxes in 2025 ($660)


    Taxes:$7,925

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9621 WINDY RIDGE RD, WINDERMERE, FL 34786

    $12,999,99959 Days on yellowkey   MLS ID: O6400740

    REDUCED by $430,001 (3.2%) on 06/15/2026

    For Sale O6400740 - 9621 WINDY RIDGE RD, WINDERMERE, FL 34786 28 photos

    Bed: 9   Bath: 13.0   Gar: 8
    Liv Area Sq Ft: 20445
       Built: 2025   Tax: $13,931 (2025)
    Community: Windsor Hill
    Single Family


    Estimated Monthly Payment: $72,392 (change assumption)
    Mortgage ($71,231) + Taxes in 2025 ($1,161)


    Taxes:$13,931

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8236 PROCIDA ISLE LN, WINDERMERE, FL 34786

    $1,100,000118 Days on yellowkey   MLS ID: O6383546

    REDUCED by $90,000 (7.6%) on 04/15/2026

    For Sale O6383546 - 8236 PROCIDA ISLE LN, WINDERMERE, FL 34786 27 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4176
       Built: 2018
    Monthly Fee: $299
       Tax: $12,887 (2025)
    Community: Windermere Isle Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,400 (change assumption)
    Mortgage ($6,027) + Fees ($299) + Taxes in 2025 ($1,074)


    Taxes:$12,887

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 9548 CROWN PRINCE LN, WINDERMERE, FL 34786

    $1,450,00034 Days on yellowkey   MLS ID: O6407352

    For Sale O6407352 - 9548 CROWN PRINCE LN, WINDERMERE, FL 34786 41 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3997
       Built: 1999
    Monthly Fee: $108
       Tax: $9,227 (2025)
    Community: Windsor Hill
    Single Family


    Estimated Monthly Payment: $8,822 (change assumption)
    Mortgage ($7,945) + Fees ($108) + Taxes in 2025 ($769)


    Taxes:$9,227

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 9072 WOODBREEZE BLVD, WINDERMERE, FL 34786

    $549,90043 Days on yellowkey   MLS ID: O6403789

    1 Days Off yellowkey (back on 6/15/2026)

    REDUCED by $12,600 (2.2%) on 05/31/2026

    For Sale O6403789 - 9072 WOODBREEZE BLVD, WINDERMERE, FL 34786 63 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1721
       Built: 1985
    Monthly Fee: $30
       Tax: $3,899 (2025)
    Community: Silver Woods
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,368 (change assumption)
    Mortgage ($3,013) + Fees ($30) + Taxes in 2025 ($325)


    Taxes:$3,899

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 8662 ABBOTSBURY DR, WINDERMERE, FL 34786

    $525,0006 Days on yellowkey   MLS ID: O6416099

    For Sale O6416099 - 8662 ABBOTSBURY DR, WINDERMERE, FL 34786 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1877
       Built: 2004
    Monthly Fee: $170
       Tax: $2,511 (2025)
    Community: Lakes/Windermere-Peachtree
    Single Family


    Estimated Monthly Payment: $3,256 (change assumption)
    Mortgage ($2,877) + Fees ($170) + Taxes in 2025 ($209)


    Taxes:$2,511

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 12826 WOODMERE CLOSE DR, WINDERMERE, FL 34786

    $665,00016 Days on yellowkey   MLS ID: O6412588

    REDUCED by $10,000 (1.5%) on 06/15/2026

    For Sale O6412588 - 12826 WOODMERE CLOSE DR, WINDERMERE, FL 34786 44 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2214
       Built: 2013
    Monthly Fee: $81
       Tax: $5,273 (2025)
    Community: Lake Sawyer South Ph 5
    Single Family


    Estimated Monthly Payment: $4,164 (change assumption)
    Mortgage ($3,644) + Fees ($81) + Taxes in 2025 ($439)


    Taxes:$5,273

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School




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.