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Windermere Single Family Homes For Sale - 261 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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  • 5061 SAWYER COVE WAY, WINDERMERE, FL 34786

    $2,590,00071 Days on yellowkey   MLS ID: O6403804

    0 Days Off yellowkey (back on 7/8/2026)

    REDUCED by $160,000 (5.8%) on 06/24/2026

    For Sale O6403804 - 5061 SAWYER COVE WAY, WINDERMERE, FL 34786 77 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3888
       Built: 2020
    Monthly Fee: $253
       Tax: $22,337 (2025)
    Community: Sawyer Sound
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,306 (change assumption)
    Mortgage ($14,191) + Fees ($253) + Taxes in 2025 ($1,861)


    Taxes:$22,337

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 910 LASCALA DR, WINDERMERE, FL 34786

    $750,00097 Days on yellowkey   MLS ID: O6397847

    REDUCED by $15,000 (2.0%) on 07/08/2026

    For Sale O6397847 - 910 LASCALA DR, WINDERMERE, FL 34786 54 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2742
       Built: 2003
    Monthly Fee: $140
       Tax: $6,213 (2025)
    Community: Belmere Village G2 48 65
    Single Family


    Estimated Monthly Payment: $4,767 (change assumption)
    Mortgage ($4,109) + Fees ($140) + Taxes in 2025 ($518)


    Taxes:$6,213

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 6120 GREATWATER DR, WINDERMERE, FL 34786

    $3,999,99973 Days on yellowkey   MLS ID: O6404574

    REDUCED by $399,001 (9.1%) on 07/08/2026

    For Sale O6404574 - 6120 GREATWATER DR, WINDERMERE, FL 34786 92 photos

    Bed: 5   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 5580
       Built: 1999
    Monthly Fee: $298
       Tax: $32,016 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $24,883 (change assumption)
    Mortgage ($21,917) + Fees ($298) + Taxes in 2025 ($2,668)


    Taxes:$32,016

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8342 BOYLA CT, WINDERMERE, FL 34786

    $6,700,0009 Days on yellowkey   MLS ID: O6422852

    For Sale O6422852 - 8342 BOYLA CT, WINDERMERE, FL 34786 93 photos

    Bed: 8   Bath: 8.5   Gar: 4
    Liv Area Sq Ft: 8133
       Built: 2026
    Monthly Fee: $298
       Tax: $9,014 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $37,761 (change assumption)
    Mortgage ($36,711) + Fees ($298) + Taxes in 2025 ($751)


    Taxes:$9,014

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 7231 SANGALLA DR, WINDERMERE, FL 34786

    $1,300,0009 Days on yellowkey   MLS ID: O6422598

    For Sale O6422598 - 7231 SANGALLA DR, WINDERMERE, FL 34786 58 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3835
       Built: 2011
    Monthly Fee: $250
       Tax: $11,139 (2025)
    Community: Casa Del Lago-Replat
    Single Family


    Estimated Monthly Payment: $8,301 (change assumption)
    Mortgage ($7,123) + Fees ($250) + Taxes in 2025 ($928)


    Taxes:$11,139

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6558 HELMSLEY CIR, WINDERMERE, FL 34786

    $630,00035 Days on yellowkey   MLS ID: S5151342

    REDUCED by $5,000 (0.8%) on 06/29/2026

    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: $3,960 (change assumption)
    Mortgage ($3,452) + Fees ($129) + Taxes in 2025 ($379)


    Taxes:$4,553

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9222 TIBET POINTE CIR, WINDERMERE, FL 34786

    $2,599,00069 Days on yellowkey   MLS ID: O6405278

    2 Days Off yellowkey (back on 7/6/2026)

    REDUCED by $100,000 (3.7%) on 05/30/2026

    For Sale O6405278 - 9222 TIBET POINTE CIR, WINDERMERE, FL 34786 99 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 5323
       Built: 2009
    Monthly Fee: $298
       Tax: $27,697 (2025)
    Community: Keenes Pointe 46/104
    Single Family


    Estimated Monthly Payment: $16,847 (change assumption)
    Mortgage ($14,241) + Fees ($298) + Taxes in 2025 ($2,308)


    Taxes:$27,697

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4224 CLARICE ESTATES DR, WINDERMERE, FL 34786

    $2,275,000398 Days on yellowkey   MLS ID: S5128974

    REDUCED by $100,000 (4.2%) on 07/07/2026

    For Sale S5128974 - 4224 CLARICE ESTATES DR, WINDERMERE, FL 34786 63 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4793
       Built: 2018
    Monthly Fee: $200
       Tax: $19,640 (2024)
    Community: Estates At Lake Clarice
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,302 (change assumption)
    Mortgage ($12,465) + Fees ($200) + Taxes in 2024 ($1,637)


    Taxes:$19,640

    Elementary School: None

    High School: Windermere High School

    Tax Year: 2024

    Middle School: None


  • 9639 WESTOVER ROBERTS RD, WINDERMERE, FL 34786

    $5,900,000311 Days on yellowkey   MLS ID: O6341883

    4 Days Off yellowkey (back on 6/22/2026)

    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


  • 7011 NOBLETON DR, WINDERMERE, FL 34786

    $580,00046 Days on yellowkey   MLS ID: O6412101

    For Sale O6412101 - 7011 NOBLETON DR, WINDERMERE, FL 34786 85 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 2460
       Built: 2003
    Monthly Fee: $82
       Tax: $9,209 (2025)
    Community: Lakes Windermere Ph 01 49 108
    Single Family


    Estimated Monthly Payment: $4,027 (change assumption)
    Mortgage ($3,178) + Fees ($82) + Taxes in 2025 ($767)


    Taxes:$9,209

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2009 WOODY DR, WINDERMERE, FL 34786

    $1,200,00010 Days on yellowkey   MLS ID: O6422132

    For Sale O6422132 - 2009 WOODY DR, WINDERMERE, FL 34786 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3540
       Built: 1974
    Monthly Fee: $85
       Tax: $6,392 (2024)
    Community: Windermere Downs
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,193 (change assumption)
    Mortgage ($6,575) + Fees ($85) + Taxes in 2024 ($533)


    Taxes:$6,392

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 6241 BLAKEFORD DR, WINDERMERE, FL 34786

    $1,795,00010 Days on yellowkey   MLS ID: O6417788

    For Sale O6417788 - 6241 BLAKEFORD DR, WINDERMERE, FL 34786 59 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3556
       Built: 1999
    Monthly Fee: $298
       Tax: $18,784 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,699 (change assumption)
    Mortgage ($9,835) + Fees ($298) + Taxes in 2025 ($1,565)


    Taxes:$18,784

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8715 QUIET MEADOWS TRL, WINDERMERE, FL 34786

    $825,00052 Days on yellowkey   MLS ID: O6410762

    0 Days Off yellowkey (back on 6/14/2026)

    REDUCED by $15,000 (1.8%) on 06/04/2026

    For Sale O6410762 - 8715 QUIET MEADOWS TRL, WINDERMERE, FL 34786 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3388
       Built: 2013
    Monthly Fee: $10
       Tax: $11,511 (2025)
    Community: Windermere Trls Ph 1C
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,490 (change assumption)
    Mortgage ($4,520) + Fees ($10) + Taxes in 2025 ($959)


    Taxes:$11,511

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11249 RAPALLO LN, WINDERMERE, FL 34786

    $750,00015 Days on yellowkey   MLS ID: O6421056

    For Sale O6421056 - 11249 RAPALLO LN, WINDERMERE, FL 34786 37 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2366
       Built: 2002
    Monthly Fee: $136
       Tax: $9,355 (2025)
    Community: Belmere Village G2 48 65
    Single Family


    Estimated Monthly Payment: $5,025 (change assumption)
    Mortgage ($4,109) + Fees ($136) + Taxes in 2025 ($780)


    Taxes:$9,355

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 20 OAKDALE ST, WINDERMERE, FL 34786

    $1,499,00015 Days on yellowkey   MLS ID: O6421265

    For Sale O6421265 - 20 OAKDALE ST, WINDERMERE, FL 34786 30 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2188
       Built: 2004   Tax: $21,535 (2025)
    Community: Davis Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,008 (change assumption)
    Mortgage ($8,213) + Taxes in 2025 ($1,795)


    Taxes:$21,535

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 8351 BOWDEN WAY, WINDERMERE, FL 34786

    $1,149,000111 Days on yellowkey   MLS ID: O6393659

    REDUCED by $50,000 (4.2%) on 06/02/2026

    For Sale O6393659 - 8351 BOWDEN WAY, WINDERMERE, FL 34786 71 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2599
       Built: 2001
    Monthly Fee: $283
       Tax: $8,252 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $7,266 (change assumption)
    Mortgage ($6,296) + Fees ($283) + Taxes in 2025 ($688)


    Taxes:$8,252

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 81 OAKDALE ST, WINDERMERE, FL 34786

    $2,300,000241 Days on yellowkey   MLS ID: S5138567

    11 Days Off yellowkey (back on 6/28/2026)

    For Sale S5138567 - 81 OAKDALE ST, WINDERMERE, FL 34786 87 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4284
       Built: 2001   Tax: $24,940 (2025)
    Community: Davis Shores
    Single Family


    Estimated Monthly Payment: $14,681 (change assumption)
    Mortgage ($12,602) + Taxes in 2025 ($2,078)


    Taxes:$24,940

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 715 MAGNOLIA ST, WINDERMERE, FL 34786

    $1,175,00096 Days on yellowkey   MLS ID: S5147648

    REDUCED by $75,000 (6.0%) on 04/27/2026

    For Sale S5147648 - 715 MAGNOLIA ST, WINDERMERE, FL 34786 44 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3390
       Built: 1999   Tax: $5,631 (2024)
    Community: Windermere Town
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,907 (change assumption)
    Mortgage ($6,438) + Taxes in 2024 ($469)


    Taxes:$5,631

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 5413 WALSH POND CT, WINDERMERE, FL 34786

    $798,000114 Days on yellowkey   MLS ID: O6391919

    REDUCED by $2,000 (0.3%) on 07/05/2026

    For Sale O6391919 - 5413 WALSH POND CT, WINDERMERE, FL 34786 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3124
       Built: 2006
    Monthly Fee: $130
       Tax: $10,646 (2025)
    Community: Edens Hammock
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,390 (change assumption)
    Mortgage ($4,372) + Fees ($130) + Taxes in 2025 ($887)


    Taxes:$10,646

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8236 PROCIDA ISLE LN, WINDERMERE, FL 34786

    $1,080,000146 Days on yellowkey   MLS ID: O6383546

    REDUCED by $20,000 (1.8%) on 06/19/2026

    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: $7,291 (change assumption)
    Mortgage ($5,918) + 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




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.