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Windermere Single Family Homes For Sale - 229 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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  • 13304 BELLARIA CIR, WINDERMERE, FL 34786

    $2,868,00016 Days on yellowkey   MLS ID: O6391558

    For Sale O6391558 - 13304 BELLARIA CIR, WINDERMERE, FL 34786 69 photos

    Bed: 6   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4920
       Built: 2013
    Monthly Fee: $483
       Tax: $30,699 (2025)
    Community: Bellaria
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $18,756 (change assumption)
    Mortgage ($15,715) + Fees ($483) + Taxes in 2025 ($2,558)


    Taxes:$30,699

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14383 CREST PALM AVE, WINDERMERE, FL 34786

    $1,166,99081 Days on yellowkey   MLS ID: G5107222

    For Sale G5107222 - 14383 CREST PALM AVE, WINDERMERE, FL 34786 51 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3550
       Built: 2026
    Monthly Fee: $245
       Tax: $2,489 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,847 (change assumption)
    Mortgage ($6,394) + Fees ($245) + Taxes in 2025 ($207)


    Taxes:$2,489

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 14354 CREST PALM AVE, WINDERMERE, FL 34786

    $1,119,99099 Days on yellowkey   MLS ID: G5106241

    For Sale G5106241 - 14354 CREST PALM AVE, WINDERMERE, FL 34786 51 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3542
       Built: 2025
    Monthly Fee: $245
       Tax: $1,309 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,491 (change assumption)
    Mortgage ($6,137) + 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


  • 8724 PEACHTREE PARK CT, WINDERMERE, FL 34786

    $850,000194 Days on yellowkey   MLS ID: S5135795

    REDUCED by $49,000 (5.5%) on 04/07/2026

    For Sale S5135795 - 8724 PEACHTREE PARK CT, WINDERMERE, FL 34786 45 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3315
       Built: 2015
    Monthly Fee: $216
       Tax: $9,856 (2024)
    Community: Peachtree Park
    Single Family


    Estimated Monthly Payment: $5,695 (change assumption)
    Mortgage ($4,657) + Fees ($216) + Taxes in 2024 ($821)


    Taxes:$9,856

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 13124 FILLY CT, WINDERMERE, FL 34786

    $1,575,000355 Days on yellowkey   MLS ID: O6303140

    For Sale O6303140 - 13124 FILLY CT, WINDERMERE, FL 34786 51 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3300
       Built: 1989
    Monthly Fee: $46
       Tax: $15,459 (2024)
    Community: Farms
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,964 (change assumption)
    Mortgage ($8,630) + Fees ($46) + Taxes in 2024 ($1,288)


    Taxes:$15,459

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 14347 CREST PALM AVE, WINDERMERE, FL 34786

    $1,108,990392 Days on yellowkey   MLS ID: G5094526

    For Sale G5094526 - 14347 CREST PALM AVE, WINDERMERE, FL 34786 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3100
       Built: 2025
    Monthly Fee: $275
       Tax: $1,309 (2023)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,461 (change assumption)
    Mortgage ($6,077) + Fees ($275) + Taxes in 2023 ($109)


    Taxes:$1,309

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2023

    Middle School: Horizon West Middle School


  • 3328 WAX BERRY CT, WINDERMERE, FL 34786

    $925,000169 Days on yellowkey   MLS ID: O6355868

    For Sale O6355868 - 3328 WAX BERRY CT, WINDERMERE, FL 34786 56 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 1984
    Monthly Fee: $21
       Tax: $10,867 (2024)
    Community: Lake Butler Estates
    Single Family


    Estimated Monthly Payment: $5,995 (change assumption)
    Mortgage ($5,068) + Fees ($21) + Taxes in 2024 ($906)


    Taxes:$10,867

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 8337 VIVARO ISLE WAY, WINDERMERE, FL 34786

    $800,000203 Days on yellowkey   MLS ID: O6332989

    For Sale O6332989 - 8337 VIVARO ISLE WAY, WINDERMERE, FL 34786 49 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3294
       Built: 2018
    Monthly Fee: $268
       Tax: $6,438 (2024)
    Community: Windermere Isle
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,188 (change assumption)
    Mortgage ($4,383) + Fees ($268) + Taxes in 2024 ($537)


    Taxes:$6,438

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 9548 CROWN PRINCE LN, WINDERMERE, FL 34786

    $1,450,00046 Days on yellowkey   MLS ID: S5144606

    REDUCED by $10,000 (0.7%) on 04/12/2026

    For Sale S5144606 - 9548 CROWN PRINCE LN, WINDERMERE, FL 34786 22 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3997
       Built: 1999
    Monthly Fee: $108
       Tax: $8,883 (2024)
    Community: Windsor Hill
    Single Family


    Estimated Monthly Payment: $8,793 (change assumption)
    Mortgage ($7,945) + Fees ($108) + Taxes in 2024 ($740)


    Taxes:$8,883

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13525 GORGONA ISLE DR, WINDERMERE, FL 34786

    $1,120,00058 Days on yellowkey   MLS ID: O6377789

    For Sale O6377789 - 13525 GORGONA ISLE DR, WINDERMERE, FL 34786 38 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: $7,184 (change assumption)
    Mortgage ($6,137) + 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


  • 6133 S HAMPSHIRE CT, WINDERMERE, FL 34786

    $3,150,0006 Days on yellowkey   MLS ID: O6397043

    0 Days Off yellowkey (back on 4/11/2026)

    For Sale O6397043 - 6133 S HAMPSHIRE CT, WINDERMERE, FL 34786 71 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 6335
       Built: 2000
    Monthly Fee: $298
       Tax: $35,657 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $20,529 (change assumption)
    Mortgage ($17,260) + Fees ($298) + Taxes in 2025 ($2,971)


    Taxes:$35,657

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13734 LAKE CAWOOD DR, WINDERMERE, FL 34786

    $1,390,00070 Days on yellowkey   MLS ID: G5107723

    2 Days Off yellowkey (back on 4/11/2026)

    REDUCED by $110,000 (7.3%) on 04/08/2026

    For Sale G5107723 - 13734 LAKE CAWOOD DR, WINDERMERE, FL 34786 81 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4437
       Built: 2006
    Monthly Fee: $172
       Tax: $11,421 (2024)
    Community: Lake Cawood Estates
    Single Family


    Estimated Monthly Payment: $8,740 (change assumption)
    Mortgage ($7,616) + Fees ($172) + Taxes in 2024 ($952)


    Taxes:$11,421

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 6799 HELMSLEY CIR, WINDERMERE, FL 34786

    $658,000149 Days on yellowkey   MLS ID: O6361417

    REDUCED by $12,000 (1.8%) on 04/08/2026

    For Sale O6361417 - 6799 HELMSLEY CIR, WINDERMERE, FL 34786 69 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2615
       Built: 2011
    Monthly Fee: $129
       Tax: $9,339 (2024)
    Community: Preston Square
    Single Family


    Estimated Monthly Payment: $4,513 (change assumption)
    Mortgage ($3,605) + Fees ($129) + Taxes in 2024 ($778)


    Taxes:$9,339

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 2806 WINDSOR HILL DR, WINDERMERE, FL 34786

    $1,150,0006 Days on yellowkey   MLS ID: O6385977

    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: $7,500 (change assumption)
    Mortgage ($6,301) + 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


  • 12863 HOLDENBURY LN, WINDERMERE, FL 34786

    $539,00021 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


  • 13312 LONGACRE DR, WINDERMERE, FL 34786

    $534,90099 Days on yellowkey   MLS ID: S5141031

    REDUCED by $9,000 (1.7%) on 04/06/2026

    For Sale S5141031 - 13312 LONGACRE DR, WINDERMERE, FL 34786 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 2013
    Monthly Fee: $120
       Tax: $7,533 (2024)
    Community: Windermere Terrace
    Single Family


    Estimated Monthly Payment: $3,679 (change assumption)
    Mortgage ($2,931) + Fees ($120) + Taxes in 2024 ($628)


    Taxes:$7,533

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 801 W 2ND AVE, WINDERMERE, FL 34786

    $3,995,00084 Days on yellowkey   MLS ID: O6375693

    For Sale O6375693 - 801 W 2ND AVE, WINDERMERE, FL 34786 44 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5639
       Built: 2008   Tax: $49,401 (2024)
    Community: Aladar On Lake Butler
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $26,007 (change assumption)
    Mortgage ($21,890) + Taxes in 2024 ($4,117)


    Taxes:$49,401

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 3130 BUTLER BAY DR N, WINDERMERE, FL 34786

    $1,725,00012 Days on yellowkey   MLS ID: O6395307

    For Sale O6395307 - 3130 BUTLER BAY DR N, WINDERMERE, FL 34786 51 photos

    Bed: 5   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 4490
       Built: 1985
    Monthly Fee: $181
       Tax: $21,502 (2025)
    Community: Butler Bay
    Single Family


    Estimated Monthly Payment: $11,425 (change assumption)
    Mortgage ($9,452) + Fees ($181) + Taxes in 2025 ($1,792)


    Taxes:$21,502

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6152 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786

    $1,130,0007 Days on yellowkey   MLS ID: O6396835

    For Sale O6396835 - 6152 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786 3 photos

    Bed: 8   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4830
       Built: 2012
    Monthly Fee: $133
       Tax: $14,684 (2025)
    Community: Windermere Lndgs Fd-1
    Single Family


    Estimated Monthly Payment: $7,548 (change assumption)
    Mortgage ($6,192) + Fees ($133) + Taxes in 2025 ($1,224)


    Taxes:$14,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786

    $2,499,000208 Days on yellowkey   MLS ID: O6344907

    For Sale O6344907 - 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786 26 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: $15,400 (change assumption)
    Mortgage ($13,693) + 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




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.