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Windermere Homes For Sale & Real Estate - 303 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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  • 2806 WINDSOR HILL DR, WINDERMERE, FL 34786

    $1,150,00020 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


  • 8226 SERENITY SPRING DR #2402, WINDERMERE, FL 34786

    $399,90057 Days on yellowkey   MLS ID: O6386960

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

    For Sale O6386960 - 8226 SERENITY SPRING DR #2402, WINDERMERE, FL 34786 56 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2028
       Built: 2013
    Monthly Fee: $541
       Tax: $3,326 (2024)
    Community: Oasis Cove At Lakes
    Spa: No

    Townhouse


    Estimated Monthly Payment: $3,009 (change assumption)
    Mortgage ($2,191) + Fees ($541) + Taxes in 2024 ($277)


    Taxes:$3,326

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 2219 RIDGEWIND WAY, WINDERMERE, FL 34786

    $1,349,00010 Days on yellowkey   MLS ID: O6400508

    For Sale O6400508 - 2219 RIDGEWIND WAY, WINDERMERE, FL 34786 45 photos

    Bed: 6   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3364
       Built: 1997
    Monthly Fee: $218
       Tax: $10,027 (2024)
    Community: Estates At Windermere
    Single Family


    Estimated Monthly Payment: $8,445 (change assumption)
    Mortgage ($7,392) + Fees ($218) + Taxes in 2024 ($836)


    Taxes:$10,027

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786

    $3,475,00092 Days on yellowkey   MLS ID: O6377244

    REDUCED by $25,000 (0.7%) on 04/22/2026

    For Sale O6377244 - 10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786 100 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 5273
       Built: 1986
    Monthly Fee: $103
       Tax: $28,092 (2025)
    Community: Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,485 (change assumption)
    Mortgage ($19,041) + Fees ($103) + Taxes in 2025 ($2,341)


    Taxes:$28,092

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 11636 WATER RUN ALY, WINDERMERE, FL 34786

    $425,000194 Days on yellowkey   MLS ID: S5136888

    For Sale S5136888 - 11636 WATER RUN ALY, WINDERMERE, FL 34786 18 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1584
       Built: 2017
    Monthly Fee: $332
       Tax: $5,634 (2024)
    Community: Ashlin Park Ph 2
    Townhouse


    Estimated Monthly Payment: $3,130 (change assumption)
    Mortgage ($2,329) + Fees ($332) + Taxes in 2024 ($469)


    Taxes:$5,634

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13420 BONICA WAY, WINDERMERE, FL 34786

    $1,875,000215 Days on yellowkey   MLS ID: O6347722

    For Sale O6347722 - 13420 BONICA WAY, WINDERMERE, FL 34786 62 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4489
       Built: 2006
    Monthly Fee: $297
       Tax: $17,970 (2024)
    Community: Tildens Grove
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,068 (change assumption)
    Mortgage ($10,274) + Fees ($297) + Taxes in 2024 ($1,498)


    Taxes:$17,970

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 7644 RIPPLEPOINTE WAY, WINDERMERE, FL 34786

    $445,00027 Days on yellowkey   MLS ID: O6395582

    For Sale O6395582 - 7644 RIPPLEPOINTE WAY, WINDERMERE, FL 34786 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1881
       Built: 2015
    Monthly Fee: $240
       Tax: $6,847 (2025)
    Community: Lake Burden South Ph 2 #35 36
    Townhouse


    Estimated Monthly Payment: $3,249 (change assumption)
    Mortgage ($2,438) + Fees ($240) + Taxes in 2025 ($571)


    Taxes:$6,847

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6552 HELMSLEY CIRCLE, WINDERMERE, FL 34786

    $469,00036 Days on yellowkey   MLS ID: O6392752

    REDUCED by $10,000 (2.1%) on 04/23/2026

    For Sale O6392752 - 6552 HELMSLEY CIRCLE, WINDERMERE, FL 34786 53 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 2008
    Monthly Fee: $315
       Tax: $3,248 (2025)
    Community: Preston Square
    Townhouse


    Estimated Monthly Payment: $3,155 (change assumption)
    Mortgage ($2,570) + Fees ($315) + Taxes in 2025 ($271)


    Taxes:$3,248

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 4 CHASE RD, WINDERMERE, FL 34786

    $875,00068 Days on yellowkey   MLS ID: O6384257

    0 Days Off yellowkey (back on 4/23/2026)

    REDUCED by $25,000 (2.8%) on 04/20/2026

    For Sale O6384257 - 4 CHASE RD, WINDERMERE, FL 34786 47 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 2386
       Built: 1971   Tax: $7,637 (2024)
    Community: Windermere Town
    Single Family


    Estimated Monthly Payment: $5,431 (change assumption)
    Mortgage ($4,794) + Taxes in 2024 ($636)


    Taxes:$7,637

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14255 SONCO AVE, WINDERMERE, FL 34786

    $849,90039 Days on yellowkey   MLS ID: O6392262

    REDUCED by $25,000 (2.9%) on 04/25/2026

    For Sale O6392262 - 14255 SONCO AVE, WINDERMERE, FL 34786 100 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2698
       Built: 2006
    Monthly Fee: $130
       Tax: $11,194 (2025)
    Community: Summerport
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,720 (change assumption)
    Mortgage ($4,657) + Fees ($130) + Taxes in 2025 ($933)


    Taxes:$11,194

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13542 GORGONA ISLE DR, WINDERMERE, FL 34786

    $895,00047 Days on yellowkey   MLS ID: O6390582

    REDUCED by $55,000 (5.8%) on 04/25/2026

    For Sale O6390582 - 13542 GORGONA ISLE DR, WINDERMERE, FL 34786 16 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2224
       Built: 2018
    Monthly Fee: $268
       Tax: $9,762 (2024)
    Community: Windermere Isle
    Single Family


    Estimated Monthly Payment: $5,985 (change assumption)
    Mortgage ($4,904) + Fees ($268) + Taxes in 2024 ($814)


    Taxes:$9,762

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 12879 EMERSONDALE AVE, WINDERMERE, FL 34786

    $399,00070 Days on yellowkey   MLS ID: O6383280

    1 Days Off yellowkey (back on 3/28/2026)

    For Sale O6383280 - 12879 EMERSONDALE AVE, WINDERMERE, FL 34786 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1565
       Built: 2010
    Monthly Fee: $185
       Tax: $5,505 (2024)
    Community: Wickham Park 04 05 06 09 10 11 12 01
    Townhouse


    Estimated Monthly Payment: $2,830 (change assumption)
    Mortgage ($2,186) + Fees ($185) + Taxes in 2024 ($459)


    Taxes:$5,505

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 14236 OASIS COVE BLVD, WINDERMERE, FL 34786

    $374,40029 Days on yellowkey   MLS ID: O6395058

    REDUCED by $5,500 (1.4%) on 04/25/2026

    For Sale O6395058 - 14236 OASIS COVE BLVD, WINDERMERE, FL 34786 70 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1512
       Built: 2011
    Monthly Fee: $541
       Tax: $3,995 (2025)
    Community: Oasis Cove At Lakeside Village
    Townhouse


    Estimated Monthly Payment: $2,925 (change assumption)
    Mortgage ($2,051) + Fees ($541) + Taxes in 2025 ($333)


    Taxes:$3,995

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 12761 HOLDENBURY LN, WINDERMERE, FL 34786

    $529,90040 Days on yellowkey   MLS ID: O6392337

    REDUCED by $10,000 (1.9%) on 04/25/2026

    For Sale O6392337 - 12761 HOLDENBURY LN, WINDERMERE, FL 34786 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2380
       Built: 2002
    Monthly Fee: $82
       Tax: $3,561 (2025)
    Community: Lakes/Windermere Ph 01 49 108
    Single Family


    Estimated Monthly Payment: $3,282 (change assumption)
    Mortgage ($2,903) + Fees ($82) + Taxes in 2025 ($297)


    Taxes:$3,561

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11333 CAMDEN PARK DR, WINDERMERE, FL 34786

    $1,196,000305 Days on yellowkey   MLS ID: O6322386

    REDUCED by $54,000 (4.3%) on 04/25/2026

    For Sale O6322386 - 11333 CAMDEN PARK DR, WINDERMERE, FL 34786 62 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3449
       Built: 2004
    Monthly Fee: $283
       Tax: $12,506 (2024)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $7,878 (change assumption)
    Mortgage ($6,553) + Fees ($283) + Taxes in 2024 ($1,042)


    Taxes:$12,506

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 12305 VIA DERNA PL, WINDERMERE, FL 34786

    $465,00099 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


  • 9639 WESTOVER CLUB CIR, WINDERMERE, FL 34786

    $847,5005 Days on yellowkey   MLS ID: O6401787

    For Sale O6401787 - 9639 WESTOVER CLUB CIR, WINDERMERE, FL 34786 58 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3248
       Built: 2001
    Monthly Fee: $115
       Tax: $11,000 (2025)
    Community: Westover Club Ph 01 44/139
    Single Family


    Estimated Monthly Payment: $5,675 (change assumption)
    Mortgage ($4,644) + Fees ($115) + Taxes in 2025 ($917)


    Taxes:$11,000

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 9721 CARILLON PARK DR, WINDERMERE, FL 34786

    $5,000,000254 Days on yellowkey   MLS ID: O6336879

    For Sale O6336879 - 9721 CARILLON PARK DR, WINDERMERE, FL 34786 81 photos

    Bed: 6   Bath: 8.0   Gar: 4
    Liv Area Sq Ft: 8305
       Built: 2011
    Monthly Fee: $277
       Tax: $47,936 (2023)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,668 (change assumption)
    Mortgage ($27,397) + Fees ($277) + Taxes in 2023 ($3,995)


    Taxes:$47,936

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2023

    Middle School: Bridgewater Middle


  • 6149 GROSVENOR SHORE DR, WINDERMERE, FL 34786

    $10,900,000170 Days on yellowkey   MLS ID: O6356355

    For Sale O6356355 - 6149 GROSVENOR SHORE DR, WINDERMERE, FL 34786 75 photos

    Bed: 6   Bath: 7.0   Gar: 7
    Liv Area Sq Ft: 6783
       Built: 2013
    Monthly Fee: $298
       Tax: $57,807 (2023)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $64,840 (change assumption)
    Mortgage ($59,725) + Fees ($298) + Taxes in 2023 ($4,817)


    Taxes:$57,807

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2023

    Middle School: Bridgewater Middle


  • 5018 RIVER GEM AVE, WINDERMERE, FL 34786

    $775,00091 Days on yellowkey   MLS ID: TB8469061

    0 Days Off yellowkey (back on 4/24/2026)

    For Sale TB8469061 - 5018 RIVER GEM AVE, WINDERMERE, FL 34786 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2379
       Built: 2005
    Monthly Fee: $130
       Tax: $8,026 (2025)
    Community: Summerport Ph 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,045 (change assumption)
    Mortgage ($4,246) + Fees ($130) + Taxes in 2025 ($669)


    Taxes:$8,026

    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.