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Windermere Homes For Sale & Real Estate - 314 homes

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

Location: Windermere

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  • 13124 FILLY CT, WINDERMERE, FL 34786

    $1,575,000401 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


  • 9222 TIBET POINTE CIR, WINDERMERE, FL 34786

    $2,599,00023 Days on yellowkey   MLS ID: O6405278

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

    For Sale O6405278 - 9222 TIBET POINTE CIR, WINDERMERE, FL 34786 100 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


  • 5538 W LAKE BUTLER RD, WINDERMERE, FL 34786

    $3,195,000123 Days on yellowkey   MLS ID: O6376859

    REDUCED by $300,000 (8.6%) on 05/15/2026

    For Sale O6376859 - 5538 W LAKE BUTLER RD, WINDERMERE, FL 34786 71 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6000
       Built: 1982
    Monthly Fee: $67
       Tax: $25,546 (2025)
    Community: Kelso On Lake Butler
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,702 (change assumption)
    Mortgage ($17,506) + Fees ($67) + Taxes in 2025 ($2,129)


    Taxes:$25,546

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8409 VIVARO ISLE WAY, WINDERMERE, FL 34786

    $1,235,00020 Days on yellowkey   MLS ID: G5112154

    For Sale G5112154 - 8409 VIVARO ISLE WAY, WINDERMERE, FL 34786 92 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4176
       Built: 2019
    Monthly Fee: $299
       Tax: $9,493 (2025)
    Community: Windermere Isle
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,857 (change assumption)
    Mortgage ($6,767) + Fees ($299) + Taxes in 2025 ($791)


    Taxes:$9,493

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 325 MAGNOLIA ST, WINDERMERE, FL 34786

    $2,450,00075 Days on yellowkey   MLS ID: O6391047

    REDUCED by $25,000 (1.0%) on 05/30/2026

    For Sale O6391047 - 325 MAGNOLIA ST, WINDERMERE, FL 34786 52 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3975
       Built: 1954   Tax: $24,094 (2025)
    Community: Windermere Town
    Single Family


    Estimated Monthly Payment: $15,432 (change assumption)
    Mortgage ($13,424) + Taxes in 2025 ($2,008)


    Taxes:$24,094

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 9960 6TH ST, WINDERMERE, FL 34786

    $3,750,0002 Days on yellowkey   MLS ID: O6412077

    For Sale O6412077 - 9960 6TH ST, WINDERMERE, FL 34786 1 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6182
       Built: 2027   Tax: $5,791 (2025)
    Community: Gotha Town
    Single Family


    Estimated Monthly Payment: $21,030 (change assumption)
    Mortgage ($20,547) + Taxes in 2025 ($483)


    Taxes:$5,791

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 12812 JACOB GRACE CT, WINDERMERE, FL 34786

    $3,699,888324 Days on yellowkey   MLS ID: V4943735

    For Sale V4943735 - 12812 JACOB GRACE CT, WINDERMERE, FL 34786 91 photos

    Bed: 4   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6054
       Built: 2007
    Monthly Fee: $317
       Tax: $25,596 (2024)
    Community: Tildens Grove Ph 01 47/65
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $22,723 (change assumption)
    Mortgage ($20,273) + Fees ($317) + Taxes in 2024 ($2,133)


    Taxes:$25,596

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786

    $2,399,000254 Days on yellowkey   MLS ID: O6344907

    REDUCED by $100,000 (4.0%) on 05/29/2026

    For Sale O6344907 - 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786 47 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: $14,852 (change assumption)
    Mortgage ($13,145) + 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


  • 8715 QUIET MEADOWS TRL, WINDERMERE, FL 34786

    $840,0006 Days on yellowkey   MLS ID: O6410762

    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: $5,572 (change assumption)
    Mortgage ($4,603) + Fees ($10) + Taxes in 2025 ($959)


    Taxes:$11,511

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786

    $2,290,00062 Days on yellowkey   MLS ID: S5146178

    REDUCED by $90,000 (3.8%) on 05/29/2026

    For Sale S5146178 - 1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786 63 photos

    Bed: 5   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 5448
       Built: 2019
    Monthly Fee: $250
       Tax: $1,982 (2025)
    Community: Estancia/Windermere
    Single Family


    Estimated Monthly Payment: $12,963 (change assumption)
    Mortgage ($12,548) + Fees ($250) + Taxes in 2025 ($165)


    Taxes:$1,982

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12966 VENNETTA WAY, WINDERMERE, FL 34786

    $386,00032 Days on yellowkey   MLS ID: S5148828

    For Sale S5148828 - 12966 VENNETTA WAY, WINDERMERE, FL 34786 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1644
       Built: 2008
    Monthly Fee: $380
       Tax: $3,153 (2025)
    Community: Lake Sawyer South Ph 3
    Townhouse


    Estimated Monthly Payment: $2,758 (change assumption)
    Mortgage ($2,115) + Fees ($380) + Taxes in 2025 ($263)


    Taxes:$3,153

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12132 MONTALCINO CIR, WINDERMERE, FL 34786

    $3,790,000207 Days on yellowkey   MLS ID: O6319854

    0 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $160,000 (4.1%) on 05/13/2026

    For Sale O6319854 - 12132 MONTALCINO CIR, WINDERMERE, FL 34786 90 photos

    Bed: 6   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 5709
       Built: 2016
    Monthly Fee: $242
       Tax: $38,798 (2024)
    Community: Casa Del Lago Rep
    Single Family


    Estimated Monthly Payment: $24,242 (change assumption)
    Mortgage ($20,767) + Fees ($242) + Taxes in 2024 ($3,233)


    Taxes:$38,798

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 5067 SAWYER COVE WAY, WINDERMERE, FL 34786

    $2,224,90071 Days on yellowkey   MLS ID: O6391750

    REDUCED by $74,100 (3.2%) on 05/20/2026

    For Sale O6391750 - 5067 SAWYER COVE WAY, WINDERMERE, FL 34786 40 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3510
       Built: 2018
    Monthly Fee: $253
       Tax: $21,824 (2025)
    Community: Sawyer Sound
    Single Family


    Estimated Monthly Payment: $14,263 (change assumption)
    Mortgage ($12,191) + Fees ($253) + Taxes in 2025 ($1,819)


    Taxes:$21,824

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6315 CLEARMEADOW CT, WINDERMERE, FL 34786

    $618,00047 Days on yellowkey   MLS ID: O6398505

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

    For Sale O6398505 - 6315 CLEARMEADOW CT, WINDERMERE, FL 34786 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2077
       Built: 2002
    Monthly Fee: $170
       Tax: $3,701 (2024)
    Community: Glenmuir 48 39
    Single Family


    Estimated Monthly Payment: $3,865 (change assumption)
    Mortgage ($3,386) + Fees ($170) + Taxes in 2024 ($308)


    Taxes:$3,701

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 801 W 2ND AVE, WINDERMERE, FL 34786

    $3,750,000130 Days on yellowkey   MLS ID: O6375693

    REDUCED by $245,000 (6.1%) on 05/29/2026

    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: $24,664 (change assumption)
    Mortgage ($20,547) + Taxes in 2024 ($4,117)


    Taxes:$49,401

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 1554 LAKE RHEA DR, WINDERMERE, FL 34786

    $1,350,00023 Days on yellowkey   MLS ID: O6406297

    REDUCED by $50,000 (3.6%) on 05/29/2026

    For Sale O6406297 - 1554 LAKE RHEA DR, WINDERMERE, FL 34786 59 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3427
       Built: 2004
    Monthly Fee: $241
       Tax: $9,102 (2025)
    Community: Reserve At Belmere
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,397 (change assumption)
    Mortgage ($7,397) + Fees ($241) + Taxes in 2025 ($759)


    Taxes:$9,102

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 6507 ROSELLA CT, WINDERMERE, FL 34786

    $7,400,000209 Days on yellowkey   MLS ID: O6353035

    5 Days Off yellowkey (back on 3/31/2026)

    For Sale O6353035 - 6507 ROSELLA CT, WINDERMERE, FL 34786 92 photos

    Bed: 7   Bath: 7.5   Gar: 4
    Liv Area Sq Ft: 10485
       Built: 2007
    Monthly Fee: $283
       Tax: $82,440 (2024)
    Community: Keenes Pointe 46/104
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $47,700 (change assumption)
    Mortgage ($40,547) + Fees ($283) + Taxes in 2024 ($6,870)


    Taxes:$82,440

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9376 WOODBREEZE BLVD, WINDERMERE, FL 34786

    $675,0003 Days on yellowkey   MLS ID: O6411270

    For Sale O6411270 - 9376 WOODBREEZE BLVD, WINDERMERE, FL 34786 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2026
       Built: 1986
    Monthly Fee: $32
       Tax: $6,103 (2025)
    Community: Silver Woods Ph 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,239 (change assumption)
    Mortgage ($3,699) + Fees ($32) + Taxes in 2025 ($509)


    Taxes:$6,103

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13019 LANGSTAFF DR, WINDERMERE, FL 34786

    $360,0003 Days on yellowkey   MLS ID: O6411551

    For Sale O6411551 - 13019 LANGSTAFF DR, WINDERMERE, FL 34786 52 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1375
       Built: 2005
    Monthly Fee: $200
       Tax: $5,303 (2025)
    Community: Lakes/Windermere-Lk Reams Twnh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,614 (change assumption)
    Mortgage ($1,973) + Fees ($200) + Taxes in 2025 ($442)


    Taxes:$5,303

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11822 SILVERLAKE PARK DR, WINDERMERE, FL 34786

    $495,0003 Days on yellowkey   MLS ID: O6409301

    For Sale O6409301 - 11822 SILVERLAKE PARK DR, WINDERMERE, FL 34786 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1829
       Built: 2014
    Monthly Fee: $85
       Tax: $6,641 (2025)
    Community: Windermere Trls Ph 1C
    Single Family


    Estimated Monthly Payment: $3,351 (change assumption)
    Mortgage ($2,712) + Fees ($85) + Taxes in 2025 ($553)


    Taxes:$6,641

    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 Homes for Sale and Other Real Estate?

Windermere home, townhome, condo, villa, and other listing sales 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 houses for sale in Windermere. You can use our website to view Multiple Listing Service (MLS) data on Windermere Real Estate. 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 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.