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Windermere Single Family Homes For Sale in Windermere - 66 homes

Windermere single family homes for sale are located in Orange County, Florida. Find Windermere single family homes in Windermere for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Windermere, Windermere single family houses.

Location: Windermere, Windermere

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  • 2617 BUTLER BAY DR N, WINDERMERE, FL 34786

    $1,649,00015 Days on yellowkey   MLS ID: O6420023

    For Sale O6420023 - 2617 BUTLER BAY DR N, WINDERMERE, FL 34786 36 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3086
       Built: 1990
    Monthly Fee: $216
       Tax: $10,025 (2025)
    Community: Windermere Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,087 (change assumption)
    Mortgage ($9,035) + Fees ($216) + Taxes in 2025 ($835)


    Taxes:$10,025

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 1700 LAKE ROBERTS CT, WINDERMERE, FL 34786

    $1,400,00051 Days on yellowkey   MLS ID: O6410847

    REDUCED by $50,000 (3.4%) on 07/15/2026

    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: $8,773 (change assumption)
    Mortgage ($7,671) + 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


  • 6820 THORNHILL CIR, WINDERMERE, FL 34786

    $520,00088 Days on yellowkey   MLS ID: V4948591

    For Sale V4948591 - 6820 THORNHILL CIR, WINDERMERE, FL 34786 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1725
       Built: 2009
    Monthly Fee: $82
       Tax: $7,228 (2025)
    Community: Lake Sawyer
    Single Family


    Estimated Monthly Payment: $3,534 (change assumption)
    Mortgage ($2,849) + Fees ($82) + Taxes in 2025 ($602)


    Taxes:$7,228

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2230 RIDGEWIND WAY, WINDERMERE, FL 34786

    $1,259,00055 Days on yellowkey   MLS ID: O6410264

    REDUCED by $90,000 (6.7%) on 06/24/2026

    For Sale O6410264 - 2230 RIDGEWIND WAY, WINDERMERE, FL 34786 44 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3064
       Built: 1999
    Monthly Fee: $220
       Tax: $8,790 (2025)
    Community: Estates At Windermere
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,851 (change assumption)
    Mortgage ($6,898) + Fees ($220) + Taxes in 2025 ($732)


    Taxes:$8,790

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 4474 BEGONIA CT, WINDERMERE, FL 34786

    $1,070,00082 Days on yellowkey   MLS ID: O6402227

    REDUCED by $50,000 (4.5%) on 07/14/2026

    For Sale O6402227 - 4474 BEGONIA CT, WINDERMERE, FL 34786 41 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4380
       Built: 1998
    Monthly Fee: $133
       Tax: $7,670 (2025)
    Community: Magnolia Park Windermere
    Single Family


    Estimated Monthly Payment: $6,635 (change assumption)
    Mortgage ($5,863) + Fees ($133) + Taxes in 2025 ($639)


    Taxes:$7,670

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 2503 BUTLER BAY DR N, WINDERMERE, FL 34786

    $1,750,00043 Days on yellowkey   MLS ID: O6413242

    REDUCED by $49,000 (2.7%) on 07/13/2026

    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: $11,152 (change assumption)
    Mortgage ($9,589) + 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


  • 109 E 12TH AVE, WINDERMERE, FL 34786

    $1,195,00092 Days on yellowkey   MLS ID: O6394569

    REDUCED by $3,000 (0.3%) on 07/13/2026

    For Sale O6394569 - 109 E 12TH AVE, WINDERMERE, FL 34786 43 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2791
       Built: 1989   Tax: $18,865 (2025)
    Community: Windermere Town
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,120 (change assumption)
    Mortgage ($6,548) + Taxes in 2025 ($1,572)


    Taxes:$18,865

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 10624 REAMS RD, WINDERMERE, FL 34786

    $475,000329 Days on yellowkey   MLS ID: O6338130

    0 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $12,000 (2.5%) on 05/28/2026

    For Sale O6338130 - 10624 REAMS RD, WINDERMERE, FL 34786 61 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2092
       Built: 2014
    Monthly Fee: $81
       Tax: $5,459 (2024)
    Community: Windermere Trls Ph 1C
    Single Family


    Estimated Monthly Payment: $3,139 (change assumption)
    Mortgage ($2,603) + Fees ($81) + Taxes in 2024 ($455)


    Taxes:$5,459

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 8662 ABBOTSBURY DR, WINDERMERE, FL 34786

    $500,00034 Days on yellowkey   MLS ID: O6416099

    0 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $25,000 (4.8%) on 06/30/2026

    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: $3,119 (change assumption)
    Mortgage ($2,740) + 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


  • 14371 CREST PALM AVE, WINDERMERE, FL 34786

    $1,049,990101 Days on yellowkey   MLS ID: G5110664

    REDUCED by $64,999 (5.8%) on 06/17/2026

    For Sale G5110664 - 14371 CREST PALM AVE, WINDERMERE, FL 34786 42 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3100
       Built: 2025
    Monthly Fee: $245
       Tax: $1,309 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,107 (change assumption)
    Mortgage ($5,753) + 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


  • 8316 LOOKOUT POINTE DR, WINDERMERE, FL 34786

    $1,075,00022 Days on yellowkey   MLS ID: S5152477

    For Sale S5152477 - 8316 LOOKOUT POINTE DR, WINDERMERE, FL 34786 74 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4332
       Built: 2016
    Monthly Fee: $8
       Tax: $14,774 (2026)
    Community: Windermere Trls Ph 3B
    Single Family


    Estimated Monthly Payment: $7,129 (change assumption)
    Mortgage ($5,890) + Fees ($8) + Taxes in 2026 ($1,231)


    Taxes:$14,774

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Horizon West Middle School


  • 13303 PENSHURST LN, WINDERMERE, FL 34786

    $669,9003 Days on yellowkey   MLS ID: O6423867

    For Sale O6423867 - 13303 PENSHURST LN, WINDERMERE, FL 34786 13 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2959
       Built: 2015   Tax: $8,999 (2025)
    Community: Windermere Sound
    Single Family


    Estimated Monthly Payment: $4,421 (change assumption)
    Mortgage ($3,671) + Taxes in 2025 ($750)


    Taxes:$8,999

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12912 DROXFORD RD, WINDERMERE, FL 34786

    $650,00013 Days on yellowkey   MLS ID: O6422064

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6422064 - 12912 DROXFORD RD, WINDERMERE, FL 34786 52 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2966
       Built: 2006
    Monthly Fee: $82
       Tax: $9,868 (2025)
    Community: Lakes/Windermere Ph 02A
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,466 (change assumption)
    Mortgage ($3,562) + Fees ($82) + Taxes in 2025 ($822)


    Taxes:$9,868

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 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


  • 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


  • 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


  • 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


  • 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


  • 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


  • 9117 OUTLOOK ROCK TRL, WINDERMERE, FL 34786

    $1,125,00041 Days on yellowkey   MLS ID: O6413948

    For Sale O6413948 - 9117 OUTLOOK ROCK TRL, WINDERMERE, FL 34786 37 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4936
       Built: 2014
    Monthly Fee: $94
       Tax: $15,179 (2025)
    Community: Windermere Trls Ph 5A
    Single Family


    Estimated Monthly Payment: $7,523 (change assumption)
    Mortgage ($6,164) + Fees ($94) + Taxes in 2025 ($1,265)


    Taxes:$15,179

    Elementary School: Bay Lake Elementary

    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.