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Windermere Homes For Sale & Real Estate - 309 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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  • 7435 RIPPLEPOINTE WAY, WINDERMERE, FL 34786

    $424,00040 Days on yellowkey   MLS ID: S5150741

    REDUCED by $1,000 (0.2%) on 07/02/2026

    For Sale S5150741 - 7435 RIPPLEPOINTE WAY, WINDERMERE, FL 34786 66 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1700
       Built: 2013
    Monthly Fee: $240
       Tax: $3,239 (2025)
    Community: Lake Burden South Ph I
    Townhouse


    Estimated Monthly Payment: $2,833 (change assumption)
    Mortgage ($2,323) + Fees ($240) + Taxes in 2025 ($270)


    Taxes:$3,239

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 17538 BLACK RAIL ST, WINDERMERE, FL 34786

    $1,380,000285 Days on yellowkey   MLS ID: O6349325

    REDUCED by $10,000 (0.7%) on 07/11/2026

    For Sale O6349325 - 17538 BLACK RAIL ST, WINDERMERE, FL 34786 32 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4999
       Built: 2014
    Monthly Fee: $167
       Tax: $16,404 (2024)
    Community: Enclave
    Single Family


    Estimated Monthly Payment: $9,095 (change assumption)
    Mortgage ($7,561) + Fees ($167) + Taxes in 2024 ($1,367)


    Taxes:$16,404

    Elementary School: None

    High School: Windermere High School

    Tax Year: 2024

    Middle School: None


  • 2053 WOODY DR, WINDERMERE, FL 34786

    $679,00012 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


  • 4718 BLUE MAJOR DR, WINDERMERE, FL 34786

    $500,00042 Days on yellowkey   MLS ID: O6410820

    REDUCED by $20,000 (3.8%) on 07/10/2026

    For Sale O6410820 - 4718 BLUE MAJOR DR, WINDERMERE, FL 34786 61 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1911
       Built: 2005
    Monthly Fee: $143
       Tax: $7,296 (2025)
    Community: Summerport Ph 05
    Single Family


    Estimated Monthly Payment: $3,491 (change assumption)
    Mortgage ($2,740) + Fees ($143) + Taxes in 2025 ($608)


    Taxes:$7,296

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11536 CLAYMONT CIR, WINDERMERE, FL 34786

    $1,175,000111 Days on yellowkey   MLS ID: O6392958

    1 Days Off yellowkey (back on 7/12/2026)

    REDUCED by $75,000 (6.0%) on 05/26/2026

    For Sale O6392958 - 11536 CLAYMONT CIR, WINDERMERE, FL 34786 68 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2882
       Built: 2002
    Monthly Fee: $298
       Tax: $8,766 (2025)
    Community: Keenes Pointe Ut 04 Sec 31 48 82
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,467 (change assumption)
    Mortgage ($6,438) + Fees ($298) + Taxes in 2025 ($731)


    Taxes:$8,766

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11217 WILLOW GARDENS DR, WINDERMERE, FL 34786

    $1,075,00018 Days on yellowkey   MLS ID: O6417903

    REDUCED by $95,000 (8.1%) on 07/07/2026

    For Sale O6417903 - 11217 WILLOW GARDENS DR, WINDERMERE, FL 34786 51 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2824
       Built: 1994
    Monthly Fee: $122
       Tax: $13,562 (2026)
    Community: Willows At Lake Rhea
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,142 (change assumption)
    Mortgage ($5,890) + Fees ($122) + Taxes in 2026 ($1,130)


    Taxes:$13,562

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Bridgewater Middle


  • 1629 HEMPEL AVE, WINDERMERE, FL 34786

    $2,500,0004 Days on yellowkey   MLS ID: O6418226

    For Sale O6418226 - 1629 HEMPEL AVE, WINDERMERE, FL 34786 89 photos

    Bed: 6   Bath: 4.0
    Liv Area Sq Ft: 4858
       Built: 1979   Tax: $10,219 (2025)
    Community: Gotha Town
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,550 (change assumption)
    Mortgage ($13,698) + Taxes in 2025 ($852)


    Taxes:$10,219

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786

    $2,399,000299 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 53 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


  • 14422 CREST PALM AVE, WINDERMERE, FL 34786

    $1,100,00025 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


  • 9433 PALM TREE DR, WINDERMERE, FL 34786

    $560,0006 Days on yellowkey   MLS ID: O6423262

    For Sale O6423262 - 9433 PALM TREE DR, WINDERMERE, FL 34786 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1819
       Built: 1986
    Monthly Fee: $32
       Tax: $7,836 (2025)
    Community: Silver Woods Ph 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,753 (change assumption)
    Mortgage ($3,068) + Fees ($32) + Taxes in 2025 ($653)


    Taxes:$7,836

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 8146 JAILENE DR, WINDERMERE, FL 34786

    $574,90014 Days on yellowkey   MLS ID: O6420838

    0 Days Off yellowkey (back on 7/10/2026)

    For Sale O6420838 - 8146 JAILENE DR, WINDERMERE, FL 34786 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2099
       Built: 2012
    Monthly Fee: $81
       Tax: $4,437 (2025)
    Community: Lake Sawyer South Phase 5
    Single Family


    Estimated Monthly Payment: $3,601 (change assumption)
    Mortgage ($3,150) + Fees ($81) + Taxes in 2025 ($370)


    Taxes:$4,437

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 9117 OUTLOOK ROCK TRL, WINDERMERE, FL 34786

    $1,125,00040 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


  • 8266 BRYCE CANYON AVE, WINDERMERE, FL 34786

    $484,50034 Days on yellowkey   MLS ID: O6410344

    REDUCED by $5,000 (1.0%) on 07/09/2026

    For Sale O6410344 - 8266 BRYCE CANYON AVE, WINDERMERE, FL 34786 57 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1825
       Built: 2016
    Monthly Fee: $81
       Tax: $5,441 (2025)
    Community: Windermere Trls Ph 3B
    Single Family


    Estimated Monthly Payment: $3,189 (change assumption)
    Mortgage ($2,655) + Fees ($81) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 7327 MILLSTONE ST, WINDERMERE, FL 34786

    $459,00099 Days on yellowkey   MLS ID: O6397203

    REDUCED by $20,000 (4.2%) on 04/21/2026

    For Sale O6397203 - 7327 MILLSTONE ST, WINDERMERE, FL 34786 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1531
       Built: 2007
    Monthly Fee: $240
       Tax: $5,184 (2025)
    Community: Lake Burden South Ph I
    Townhouse


    Estimated Monthly Payment: $3,187 (change assumption)
    Mortgage ($2,515) + Fees ($240) + Taxes in 2025 ($432)


    Taxes:$5,184

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8724 PEACHTREE PARK CT, WINDERMERE, FL 34786

    $839,500285 Days on yellowkey   MLS ID: S5135795

    REDUCED by $10,500 (1.2%) on 06/23/2026

    For Sale S5135795 - 8724 PEACHTREE PARK CT, WINDERMERE, FL 34786 26 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: $5,637 (change assumption)
    Mortgage ($4,600) + 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


  • 5032 BEACH RIVER RD, WINDERMERE, FL 34786

    $569,00023 Days on yellowkey   MLS ID: O6418594

    For Sale O6418594 - 5032 BEACH RIVER RD, WINDERMERE, FL 34786 29 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2306
       Built: 2004
    Monthly Fee: $130
       Tax: $4,711 (2025)
    Community: Summerport Ph 02
    Single Family


    Estimated Monthly Payment: $3,640 (change assumption)
    Mortgage ($3,118) + Fees ($130) + Taxes in 2025 ($393)


    Taxes:$4,711

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1002 OAKDALE ST, WINDERMERE, FL 34786

    $950,00092 Days on yellowkey   MLS ID: TB8495717

    REDUCED by $15,000 (1.6%) on 07/11/2026

    For Sale TB8495717 - 1002 OAKDALE ST, WINDERMERE, FL 34786 60 photos

    Bed: 4   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 3516
       Built: 1973   Tax: $8,799 (2025)
    Community: Windermere Town
    Single Family


    Estimated Monthly Payment: $5,939 (change assumption)
    Mortgage ($5,205) + Taxes in 2025 ($733)


    Taxes:$8,799

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11472 CENTER LAKE DR, WINDERMERE, FL 34786

    $429,00027 Days on yellowkey   MLS ID: O6418257

    REDUCED by $14,000 (3.2%) on 07/10/2026

    For Sale O6418257 - 11472 CENTER LAKE DR, WINDERMERE, FL 34786 53 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1898
       Built: 2014
    Monthly Fee: $366
       Tax: $6,854 (2025)
    Community: Lake Burden South Ph 2
    Townhouse


    Estimated Monthly Payment: $3,288 (change assumption)
    Mortgage ($2,351) + Fees ($366) + Taxes in 2025 ($571)


    Taxes:$6,854

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9057 BALMORAL MEWS SQ, WINDERMERE, FL 34786

    $1,854,000123 Days on yellowkey   MLS ID: O6390656

    REDUCED by $5,000 (0.3%) on 07/10/2026

    For Sale O6390656 - 9057 BALMORAL MEWS SQ, WINDERMERE, FL 34786 67 photos

    Bed: 6   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5430
       Built: 1997
    Monthly Fee: $267
       Tax: $12,735 (2025)
    Community: Balmoral
    Single Family


    Estimated Monthly Payment: $11,487 (change assumption)
    Mortgage ($10,159) + Fees ($267) + Taxes in 2025 ($1,061)


    Taxes:$12,735

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 14506 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786

    $405,00026 Days on yellowkey   MLS ID: O6417034

    0 Days Off yellowkey (back on 7/9/2026)

    REDUCED by $5,000 (1.2%) on 07/08/2026

    For Sale O6417034 - 14506 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 2006
    Monthly Fee: $201
       Tax: $2,500 (2025)
    Community: Tennyson Pk/Summerport
    Townhouse


    Estimated Monthly Payment: $2,628 (change assumption)
    Mortgage ($2,219) + Fees ($201) + Taxes in 2025 ($208)


    Taxes:$2,500

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle




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.