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Windermere Single Family Homes For Sale - 265 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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  • 11486 MISTY OAK ALY, WINDERMERE, FL 34786

    $549,00040 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


  • 12720 JACOB GRACE CT, WINDERMERE, FL 34786

    $2,845,00087 Days on yellowkey   MLS ID: TB8476930

    REDUCED by $50,000 (1.7%) on 05/18/2026

    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: $16,997 (change assumption)
    Mortgage ($15,589) + 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


  • 2806 WINDSOR HILL DR, WINDERMERE, FL 34786

    $1,099,00052 Days on yellowkey   MLS ID: O6385977

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

    REDUCED by $51,000 (4.4%) on 05/02/2026

    For Sale O6385977 - 2806 WINDSOR HILL DR, WINDERMERE, FL 34786 72 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3181
       Built: 1989
    Monthly Fee: $111
       Tax: $13,057 (2024)
    Community: Windsor Hill
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,221 (change assumption)
    Mortgage ($6,022) + Fees ($111) + Taxes in 2024 ($1,088)


    Taxes:$13,057

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 12533 CRAGSIDE LN, WINDERMERE, FL 34786

    $575,00023 Days on yellowkey   MLS ID: O6405628

    For Sale O6405628 - 12533 CRAGSIDE LN, WINDERMERE, FL 34786 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2151
       Built: 2004
    Monthly Fee: $82
       Tax: $8,484 (2025)
    Community: Lakes Windermere Ph 01 49 108
    Single Family


    Estimated Monthly Payment: $3,940 (change assumption)
    Mortgage ($3,151) + Fees ($82) + Taxes in 2025 ($707)


    Taxes:$8,484

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11208 LEDGEMENT LN, WINDERMERE, FL 34786

    $999,950243 Days on yellowkey   MLS ID: O6325096

    1 Days Off yellowkey (back on 5/17/2026)

    REDUCED by $50 (0.0%) on 05/09/2026

    For Sale O6325096 - 11208 LEDGEMENT LN, WINDERMERE, FL 34786 37 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2788
       Built: 2002
    Monthly Fee: $140
       Tax: $6,561 (2024)
    Community: Glenmuir 48 39
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,166 (change assumption)
    Mortgage ($5,479) + Fees ($140) + Taxes in 2024 ($547)


    Taxes:$6,561

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 5145 LATROBE DR, WINDERMERE, FL 34786

    $3,299,000105 Days on yellowkey   MLS ID: O6382287

    REDUCED by $150,000 (4.3%) on 05/17/2026

    For Sale O6382287 - 5145 LATROBE DR, WINDERMERE, FL 34786 73 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4512
       Built: 1991
    Monthly Fee: $1,224
       Tax: $27,776 (2025)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $21,615 (change assumption)
    Mortgage ($18,076) + Fees ($1,224) + Taxes in 2025 ($2,315)


    Taxes:$27,776

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 14341 CREST PALM AVE, WINDERMERE, FL 34786

    $1,130,64315 Days on yellowkey   MLS ID: G5112469

    For Sale G5112469 - 14341 CREST PALM AVE, WINDERMERE, FL 34786 1 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3153
       Built: 2026
    Monthly Fee: $245
       Tax: $1,309 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,549 (change assumption)
    Mortgage ($6,195) + 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


  • 12863 HOLDENBURY LN, WINDERMERE, FL 34786

    $539,00067 Days on yellowkey   MLS ID: O6393781

    For Sale O6393781 - 12863 HOLDENBURY LN, WINDERMERE, FL 34786 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2006
    Monthly Fee: $82
       Tax: $7,361 (2024)
    Community: Lakes Of Windermere
    Single Family


    Estimated Monthly Payment: $3,649 (change assumption)
    Mortgage ($2,953) + Fees ($82) + Taxes in 2024 ($613)


    Taxes:$7,361

    Elementary School: Sunset Park Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 8796 PEACHTREE PARK CT, WINDERMERE, FL 34786

    $949,99946 Days on yellowkey   MLS ID: O6399023

    REDUCED by $30,000 (3.1%) on 05/16/2026

    For Sale O6399023 - 8796 PEACHTREE PARK CT, WINDERMERE, FL 34786 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3299
       Built: 2014
    Monthly Fee: $218
       Tax: $9,513 (2025)
    Community: Peachtree Park
    Single Family


    Estimated Monthly Payment: $6,216 (change assumption)
    Mortgage ($5,205) + Fees ($218) + Taxes in 2025 ($793)


    Taxes:$9,513

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 9011 PINNACLE CIR, WINDERMERE, FL 34786

    $2,250,00041 Days on yellowkey   MLS ID: O6400872

    For Sale O6400872 - 9011 PINNACLE CIR, WINDERMERE, FL 34786 53 photos

    Bed: 5   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 6546
       Built: 2002
    Monthly Fee: $172
       Tax: $23,090 (2025)
    Community: Lake Down Crest
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,425 (change assumption)
    Mortgage ($12,328) + Fees ($172) + Taxes in 2025 ($1,924)


    Taxes:$23,090

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 9548 CROWN PRINCE LN, WINDERMERE, FL 34786

    $1,450,00016 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


  • 505 JENNIFER LN, WINDERMERE, FL 34786

    $2,199,00093 Days on yellowkey   MLS ID: O6384643

    4 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $51,000 (2.3%) on 04/28/2026

    For Sale O6384643 - 505 JENNIFER LN, WINDERMERE, FL 34786 95 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3525
       Built: 1989
    Monthly Fee: $333
       Tax: $7,624 (2024)
    Community: Windermere Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,017 (change assumption)
    Mortgage ($12,049) + Fees ($333) + Taxes in 2024 ($635)


    Taxes:$7,624

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 5825 OXFORD MOOR BLVD, WINDERMERE, FL 34786

    $1,500,00045 Days on yellowkey   MLS ID: O6399697

    1 Days Off yellowkey (back on 5/15/2026)

    For Sale O6399697 - 5825 OXFORD MOOR BLVD, WINDERMERE, FL 34786 57 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4319
       Built: 2002
    Monthly Fee: $183
       Tax: $16,530 (2025)
    Community: Oxford Moor
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,779 (change assumption)
    Mortgage ($8,219) + Fees ($183) + Taxes in 2025 ($1,378)


    Taxes:$16,530

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 2219 RIDGEWIND WAY, WINDERMERE, FL 34786

    $1,299,00042 Days on yellowkey   MLS ID: O6400508

    1 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $50,000 (3.7%) on 05/04/2026

    For Sale O6400508 - 2219 RIDGEWIND WAY, WINDERMERE, FL 34786 45 photos

    Bed: 6   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3364
       Built: 1997
    Monthly Fee: $218
       Tax: $10,027 (2024)
    Community: Estates At Windermere
    Single Family


    Estimated Monthly Payment: $8,171 (change assumption)
    Mortgage ($7,118) + Fees ($218) + Taxes in 2024 ($836)


    Taxes:$10,027

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 212 W 1ST AVE, WINDERMERE, FL 34786

    $3,900,00034 Days on yellowkey   MLS ID: S5148430

    INCREASED by $2,300,000 (143.8%) on 05/13/2026

    For Sale S5148430 - 212 W 1ST AVE, WINDERMERE, FL 34786 11 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3800
       Built: 2026   Tax: $12,463 (2025)
    Community: Windermere Town
    Spa: No

    Single Family


    Estimated Monthly Payment: $22,408 (change assumption)
    Mortgage ($21,369) + Taxes in 2025 ($1,039)


    Taxes:$12,463

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 2127 LILYPAD LN, WINDERMERE, FL 34786

    $1,250,00030 Days on yellowkey   MLS ID: O6403899

    0 Days Off yellowkey (back on 5/14/2026)

    For Sale O6403899 - 2127 LILYPAD LN, WINDERMERE, FL 34786 60 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3349
       Built: 1989
    Monthly Fee: $122
       Tax: $10,870 (2025)
    Community: Willows At Lake Rhea Ph 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,877 (change assumption)
    Mortgage ($6,849) + Fees ($122) + Taxes in 2025 ($906)


    Taxes:$10,870

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 81 OAKDALE ST, WINDERMERE, FL 34786

    $2,300,000195 Days on yellowkey   MLS ID: S5138567

    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


  • 13609 ANCILLA BLVD, WINDERMERE, FL 34786

    $749,999107 Days on yellowkey   MLS ID: O6381542

    0 Days Off yellowkey (back on 5/12/2026)

    REDUCED by $39,001 (4.9%) on 04/14/2026

    For Sale O6381542 - 13609 ANCILLA BLVD, WINDERMERE, FL 34786 66 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3360
       Built: 2005
    Monthly Fee: $130
       Tax: $9,521 (2024)
    Community: Summerport Ph 03
    Single Family


    Estimated Monthly Payment: $5,033 (change assumption)
    Mortgage ($4,109) + Fees ($130) + Taxes in 2024 ($793)


    Taxes:$9,521

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 8648 POWDER RIDGE TRL, WINDERMERE, FL 34786

    $499,000131 Days on yellowkey   MLS ID: O6373065

    1 Days Off yellowkey (back on 5/13/2026)

    REDUCED by $17,000 (3.3%) on 04/13/2026

    For Sale O6373065 - 8648 POWDER RIDGE TRL, WINDERMERE, FL 34786 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1876
       Built: 2014
    Monthly Fee: $81
       Tax: $6,733 (2025)
    Community: Windermere Trls Ph 1C
    Single Family


    Estimated Monthly Payment: $3,376 (change assumption)
    Mortgage ($2,734) + Fees ($81) + Taxes in 2025 ($561)


    Taxes:$6,733

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 606 E 6TH AVE, WINDERMERE, FL 34786

    $2,350,00074 Days on yellowkey   MLS ID: O6390327

    2 Days Off yellowkey (back on 5/13/2026)

    For Sale O6390327 - 606 E 6TH AVE, WINDERMERE, FL 34786 42 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4471
       Built: 2016   Tax: $25,043 (2025)
    Community: Diamondhead
    Single Family


    Estimated Monthly Payment: $14,963 (change assumption)
    Mortgage ($12,876) + Taxes in 2025 ($2,087)


    Taxes:$25,043

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha 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.