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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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  • 84 OAKDALE ST, WINDERMERE, FL 34786

    $1,875,00095 Days on yellowkey   MLS ID: O6372842

    For Sale O6372842 - 84 OAKDALE ST, WINDERMERE, FL 34786 52 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3519
       Built: 2020   Tax: $12,265 (2024)
    Community: Davis Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,296 (change assumption)
    Mortgage ($10,274) + Taxes in 2024 ($1,022)


    Taxes:$12,265

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 11449 LAKE BUTLER BLVD, WINDERMERE, FL 34786

    $1,730,000Listed 04/17/2026 7:34AM   MLS ID: O6399319

    For Sale O6399319 - 11449 LAKE BUTLER BLVD, WINDERMERE, FL 34786 48 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4648
       Built: 1995   Tax: $19,423 (2025)
    Community: Lake Butler Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,098 (change assumption)
    Mortgage ($9,479) + Taxes in 2025 ($1,619)


    Taxes:$19,423

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 5525 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786

    $14,250,000333 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

    $984,90043 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

    $3,299,000Listed 04/16/2026 11:38PM   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

    $649,0001 Day 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

    $1,500,0001 Day 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


  • 8179 MARITIME FLAG ST #101, WINDERMERE, FL 34786

    $330,0001 Day on yellowkey   MLS ID: O6399551

    For Sale O6399551 - 8179 MARITIME FLAG ST #101, WINDERMERE, FL 34786 34 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1442
       Built: 2006   Tax: $4,106 (2025)
    Community: Lakeside/Lks/Windermere
    Condo


    Estimated Monthly Payment: $2,150 (change assumption)
    Mortgage ($1,808) + Taxes in 2025 ($342)


    Taxes:$4,106

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 9663 GOTHA RD, WINDERMERE, FL 34786

    $1,400,0001 Day 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

    $1,600,00078 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


  • 3328 WAX BERRY CT, WINDERMERE, FL 34786

    $925,000171 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


  • 4812 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786

    $3,699,000226 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

    $315,00064 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

    $849,90069 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


  • 17514 BLACK RAIL ST, WINDERMERE, FL 34786

    $725,00082 Days on yellowkey   MLS ID: O6376756

    For Sale O6376756 - 17514 BLACK RAIL ST, WINDERMERE, FL 34786 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2373
       Built: 2014
    Monthly Fee: $167
       Tax: $8,578 (2025)
    Community: Enclave
    Single Family


    Estimated Monthly Payment: $4,854 (change assumption)
    Mortgage ($3,973) + Fees ($167) + Taxes in 2025 ($715)


    Taxes:$8,578

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 713 MAIN ST, WINDERMERE, FL 34786

    $2,235,000120 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

    $658,000151 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

    $680,00051 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


  • 8796 PEACHTREE PARK CT, WINDERMERE, FL 34786

    $979,9991 Day on yellowkey   MLS ID: O6399023

    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: $6,380 (change assumption)
    Mortgage ($5,370) + 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


  • 6840 HELMSLEY CIR, WINDERMERE, FL 34786

    $719,99970 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.