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Windermere Homes For Sale & Real Estate - 286 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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  • 12305 VIA DERNA PL, WINDERMERE, FL 34786

    $465,00089 Days on yellowkey   MLS ID: O6374964

    REDUCED by $5,000 (1.1%) on 04/17/2026

    For Sale O6374964 - 12305 VIA DERNA PL, WINDERMERE, FL 34786 24 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1891
       Built: 2014
    Monthly Fee: $316
       Tax: $5,016 (2025)
    Community: Carrington
    Townhouse


    Estimated Monthly Payment: $3,282 (change assumption)
    Mortgage ($2,548) + Fees ($316) + Taxes in 2025 ($418)


    Taxes:$5,016

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2068 ROBERTS POINT DR, WINDERMERE, FL 34786

    $2,350,0003 Days on yellowkey   MLS ID: O6397543

    For Sale O6397543 - 2068 ROBERTS POINT DR, WINDERMERE, FL 34786 80 photos

    Bed: 5   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 4876
       Built: 1999
    Monthly Fee: $325
       Tax: $12,356 (2025)
    Community: Waterford Pointe Ph 02 Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,231 (change assumption)
    Mortgage ($12,876) + Fees ($325) + Taxes in 2025 ($1,030)


    Taxes:$12,356

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13369 GORGONA ISLE DR, WINDERMERE, FL 34786

    $449,98095 Days on yellowkey   MLS ID: O6373676

    1 Days Off yellowkey (back on 4/17/2026)

    For Sale O6373676 - 13369 GORGONA ISLE DR, WINDERMERE, FL 34786 39 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1767
       Built: 2019
    Monthly Fee: $240
       Tax: $4,623 (2024)
    Community: Legado
    Townhouse


    Estimated Monthly Payment: $3,091 (change assumption)
    Mortgage ($2,466) + Fees ($240) + Taxes in 2024 ($385)


    Taxes:$4,623

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 109 E 12TH AVE, WINDERMERE, FL 34786

    $1,225,0004 Days on yellowkey   MLS ID: O6394569

    For Sale O6394569 - 109 E 12TH AVE, WINDERMERE, FL 34786 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2791
       Built: 1989   Tax: $20,244 (2025)
    Community: Windermere Town
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,399 (change assumption)
    Mortgage ($6,712) + Taxes in 2025 ($1,687)


    Taxes:$20,244

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786

    $2,499,000212 Days on yellowkey   MLS ID: O6344907

    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: $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


  • 1329 GLENHEATHER DR, WINDERMERE, FL 34786

    $821,00013 Days on yellowkey   MLS ID: O6395704

    For Sale O6395704 - 1329 GLENHEATHER DR, WINDERMERE, FL 34786 68 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2519
       Built: 2002
    Monthly Fee: $201
       Tax: $7,240 (2025)
    Community: Reserve At Belmere
    Single Family


    Estimated Monthly Payment: $5,303 (change assumption)
    Mortgage ($4,499) + Fees ($201) + Taxes in 2025 ($603)


    Taxes:$7,240

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 5525 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786

    $14,250,000335 Days on yellowkey   MLS ID: O6304800

    0 Days Off yellowkey (back on 4/17/2026)

    For Sale O6304800 - 5525 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786 100 photos

    Bed: 5   Bath: 5.5   Gar: 6
    Liv Area Sq Ft: 9511
       Built: 1999
    Monthly Fee: $1,224
       Tax: $37,372 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $82,419 (change assumption)
    Mortgage ($78,080) + Fees ($1,224) + Taxes in 2024 ($3,114)


    Taxes:$37,372

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 11866 CAMDEN PARK DR, WINDERMERE, FL 34786

    $984,90045 Days on yellowkey   MLS ID: O6381558

    For Sale O6381558 - 11866 CAMDEN PARK DR, WINDERMERE, FL 34786 57 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3337
       Built: 2006
    Monthly Fee: $298
       Tax: $13,742 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $6,840 (change assumption)
    Mortgage ($5,397) + Fees ($298) + Taxes in 2025 ($1,145)


    Taxes:$13,742

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 4029 ISABELLA CIR, WINDERMERE, FL 34786

    $3,299,0003 Days on yellowkey   MLS ID: O6400064

    For Sale O6400064 - 4029 ISABELLA CIR, WINDERMERE, FL 34786 98 photos

    Bed: 6   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 7217
       Built: 2018
    Monthly Fee: $480
       Tax: $30,300 (2025)
    Community: Casabella
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,081 (change assumption)
    Mortgage ($18,076) + Fees ($480) + Taxes in 2025 ($2,525)


    Taxes:$30,300

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9011 CHAPMAN OAK CT, WINDERMERE, FL 34786

    $649,0003 Days on yellowkey   MLS ID: S5148031

    For Sale S5148031 - 9011 CHAPMAN OAK CT, WINDERMERE, FL 34786 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2050
       Built: 1987
    Monthly Fee: $31
       Tax: $8,592 (2025)
    Community: Silver Woods Ph 05
    Single Family


    Estimated Monthly Payment: $4,303 (change assumption)
    Mortgage ($3,556) + Fees ($31) + Taxes in 2025 ($716)


    Taxes:$8,592

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5825 OXFORD MOOR BLVD, WINDERMERE, FL 34786

    $1,500,0003 Days on yellowkey   MLS ID: O6399697

    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


  • 9663 GOTHA RD, WINDERMERE, FL 34786

    $1,400,0003 Days on yellowkey   MLS ID: O6399130

    For Sale O6399130 - 9663 GOTHA RD, WINDERMERE, FL 34786 100 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3731
       Built: 2000   Tax: $8,425 (2025)
    Community: Gotha Town
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,373 (change assumption)
    Mortgage ($7,671) + Taxes in 2025 ($702)


    Taxes:$8,425

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 1420 DINGENS AVE, WINDERMERE, FL 34786

    $1,600,00080 Days on yellowkey   MLS ID: O6376538

    For Sale O6376538 - 1420 DINGENS AVE, WINDERMERE, FL 34786 41 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4072
       Built: 2018   Tax: $13,393 (2025)
    Community: Gotha
    Single Family


    Estimated Monthly Payment: $9,883 (change assumption)
    Mortgage ($8,767) + Taxes in 2025 ($1,116)


    Taxes:$13,393

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 4812 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786

    $3,699,000228 Days on yellowkey   MLS ID: O6339134

    For Sale O6339134 - 4812 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786 66 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4262
       Built: 2007
    Monthly Fee: $1,146
       Tax: $45,888 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $25,238 (change assumption)
    Mortgage ($20,268) + Fees ($1,146) + Taxes in 2024 ($3,824)


    Taxes:$45,888

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 11434 JASPER KAY TER #1120, WINDERMERE, FL 34786

    $315,00066 Days on yellowkey   MLS ID: O6382035

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale O6382035 - 11434 JASPER KAY TER #1120, WINDERMERE, FL 34786 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1332
       Built: 2007
    Monthly Fee: $489
       Tax: $2,663 (2024)
    Community: Lakeside/Lks/Windermere
    Condo


    Estimated Monthly Payment: $2,437 (change assumption)
    Mortgage ($1,726) + Fees ($489) + Taxes in 2024 ($222)


    Taxes:$2,663

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 13302 ROSKIN LN, WINDERMERE, FL 34786

    $849,90071 Days on yellowkey   MLS ID: O6380701

    For Sale O6380701 - 13302 ROSKIN LN, WINDERMERE, FL 34786 46 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3424
       Built: 2011
    Monthly Fee: $82
       Tax: $10,244 (2024)
    Community: Lake Sawyer South Ph 1
    Single Family


    Estimated Monthly Payment: $5,593 (change assumption)
    Mortgage ($4,657) + Fees ($82) + Taxes in 2024 ($854)


    Taxes:$10,244

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 713 MAIN ST, WINDERMERE, FL 34786

    $2,235,000122 Days on yellowkey   MLS ID: O6368185

    For Sale O6368185 - 713 MAIN ST, WINDERMERE, FL 34786 82 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 5031
       Built: 2013   Tax: $9,559 (2025)
    Community: Windermere
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,043 (change assumption)
    Mortgage ($12,246) + Taxes in 2025 ($797)


    Taxes:$9,559

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 6799 HELMSLEY CIR, WINDERMERE, FL 34786

    $658,000153 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


  • 8552 POWDER RIDGE TRL, WINDERMERE, FL 34786

    $680,00053 Days on yellowkey   MLS ID: S5144276

    For Sale S5144276 - 8552 POWDER RIDGE TRL, WINDERMERE, FL 34786 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2612
       Built: 2016
    Monthly Fee: $82
       Tax: $8,150 (2024)
    Community: Windermere Trls Ph 3B
    Single Family


    Estimated Monthly Payment: $4,487 (change assumption)
    Mortgage ($3,726) + Fees ($82) + Taxes in 2024 ($679)


    Taxes:$8,150

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6840 HELMSLEY CIR, WINDERMERE, FL 34786

    $719,99972 Days on yellowkey   MLS ID: S5142930

    1 Days Off yellowkey (back on 4/16/2026)

    For Sale S5142930 - 6840 HELMSLEY CIR, WINDERMERE, FL 34786 76 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2847
       Built: 2009
    Monthly Fee: $129
       Tax: $5,044 (2024)
    Community: Preston Square
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,494 (change assumption)
    Mortgage ($3,945) + Fees ($129) + Taxes in 2024 ($420)


    Taxes:$5,044

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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.