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Windermere Homes For Sale & Real Estate - 302 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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  • 14215 DESERT HAVEN ST #3507, WINDERMERE, FL 34786

    $389,00036 Days on yellowkey   MLS ID: S5145972

    2 Days Off yellowkey (back on 4/14/2026)

    For Sale S5145972 - 14215 DESERT HAVEN ST #3507, WINDERMERE, FL 34786 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2028
       Built: 2012
    Monthly Fee: $522
       Tax: $5,453 (2025)
    Community: Oasis Cove 2 At Lakeside Village Condo Ph 1
    Townhouse


    Estimated Monthly Payment: $3,108 (change assumption)
    Mortgage ($2,131) + Fees ($522) + Taxes in 2025 ($454)


    Taxes:$5,453

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 715 MAGNOLIA ST, WINDERMERE, FL 34786

    $1,250,00013 Days on yellowkey   MLS ID: S5147648

    For Sale S5147648 - 715 MAGNOLIA ST, WINDERMERE, FL 34786 44 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3390
       Built: 1999   Tax: $5,631 (2024)
    Community: Windermere Town
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,318 (change assumption)
    Mortgage ($6,849) + Taxes in 2024 ($469)


    Taxes:$5,631

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 6343 MERRICK LANDING BLVD, WINDERMERE, FL 34786

    $325,000125 Days on yellowkey   MLS ID: O6368529

    For Sale O6368529 - 6343 MERRICK LANDING BLVD, WINDERMERE, FL 34786 43 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1068
       Built: 2003
    Monthly Fee: $300
       Tax: $4,465 (2024)
    Community: Merrick Landing
    Townhouse


    Estimated Monthly Payment: $2,453 (change assumption)
    Mortgage ($1,781) + Fees ($300) + Taxes in 2024 ($372)


    Taxes:$4,465

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 5106 TILDENS GROVE BLVD, WINDERMERE, FL 34786

    $1,700,00016 Days on yellowkey   MLS ID: O6397273

    For Sale O6397273 - 5106 TILDENS GROVE BLVD, WINDERMERE, FL 34786 57 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4572
       Built: 2006
    Monthly Fee: $317
       Tax: $12,584 (2025)
    Community: Tildens Grove Ph 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,680 (change assumption)
    Mortgage ($9,315) + Fees ($317) + Taxes in 2025 ($1,049)


    Taxes:$12,584

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 1703 ROBERTS LANDING RD, WINDERMERE, FL 34786

    $1,520,000216 Days on yellowkey   MLS ID: O6346120

    For Sale O6346120 - 1703 ROBERTS LANDING RD, WINDERMERE, FL 34786 63 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3288
       Built: 1996   Tax: $17,269 (2024)
    Community: Roberts Landing
    Single Family


    Estimated Monthly Payment: $9,768 (change assumption)
    Mortgage ($8,329) + Taxes in 2024 ($1,439)


    Taxes:$17,269

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 8724 PEACHTREE PARK CT, WINDERMERE, FL 34786

    $850,000203 Days on yellowkey   MLS ID: S5135795

    REDUCED by $49,000 (5.5%) on 04/07/2026

    For Sale S5135795 - 8724 PEACHTREE PARK CT, WINDERMERE, FL 34786 45 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: $5,695 (change assumption)
    Mortgage ($4,657) + 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


  • 13734 LAKE CAWOOD DR, WINDERMERE, FL 34786

    $1,390,00079 Days on yellowkey   MLS ID: G5107723

    2 Days Off yellowkey (back on 4/11/2026)

    REDUCED by $110,000 (7.3%) on 04/08/2026

    For Sale G5107723 - 13734 LAKE CAWOOD DR, WINDERMERE, FL 34786 81 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4437
       Built: 2006
    Monthly Fee: $172
       Tax: $11,421 (2024)
    Community: Lake Cawood Estates
    Single Family


    Estimated Monthly Payment: $8,740 (change assumption)
    Mortgage ($7,616) + Fees ($172) + Taxes in 2024 ($952)


    Taxes:$11,421

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 12863 HOLDENBURY LN, WINDERMERE, FL 34786

    $539,00030 Days on yellowkey   MLS ID: O6393781

    For Sale O6393781 - 12863 HOLDENBURY LN, WINDERMERE, FL 34786 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2006
    Monthly Fee: $82
       Tax: $7,361 (2024)
    Community: Lakes Of Windermere
    Single Family


    Estimated Monthly Payment: $3,649 (change assumption)
    Mortgage ($2,953) + Fees ($82) + Taxes in 2024 ($613)


    Taxes:$7,361

    Elementary School: Sunset Park Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 6152 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786

    $1,130,00016 Days on yellowkey   MLS ID: O6396835

    For Sale O6396835 - 6152 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786 3 photos

    Bed: 8   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4830
       Built: 2012
    Monthly Fee: $133
       Tax: $14,684 (2025)
    Community: Windermere Lndgs Fd-1
    Single Family


    Estimated Monthly Payment: $7,548 (change assumption)
    Mortgage ($6,192) + Fees ($133) + Taxes in 2025 ($1,224)


    Taxes:$14,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5145 LATROBE DR, WINDERMERE, FL 34786

    $3,449,00068 Days on yellowkey   MLS ID: O6382287

    For Sale O6382287 - 5145 LATROBE DR, WINDERMERE, FL 34786 73 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4512
       Built: 1991
    Monthly Fee: $1,224
       Tax: $27,776 (2025)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $22,437 (change assumption)
    Mortgage ($18,898) + Fees ($1,224) + Taxes in 2025 ($2,315)


    Taxes:$27,776

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 8350 BOWDEN WAY, WINDERMERE, FL 34786

    $1,199,00021 Days on yellowkey   MLS ID: O6395966

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale O6395966 - 8350 BOWDEN WAY, WINDERMERE, FL 34786 45 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3368
       Built: 2001
    Monthly Fee: $298
       Tax: $8,638 (2025)
    Community: Keenes Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,588 (change assumption)
    Mortgage ($6,570) + Fees ($298) + Taxes in 2025 ($720)


    Taxes:$8,638

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14368 DESERT HAVEN ST #4106, WINDERMERE, FL 34786

    $360,00018 Days on yellowkey   MLS ID: O6396784

    For Sale O6396784 - 14368 DESERT HAVEN ST #4106, WINDERMERE, FL 34786 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1840
       Built: 2013
    Monthly Fee: $541
       Tax: $3,885 (2025)
    Community: Oasis Cove Ii/Lakeside Village #Xi
    Spa: No

    Condo


    Estimated Monthly Payment: $2,837 (change assumption)
    Mortgage ($1,973) + Fees ($541) + Taxes in 2025 ($324)


    Taxes:$3,885

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1849 WATERMERE LN, WINDERMERE, FL 34786

    $1,325,00041 Days on yellowkey   MLS ID: O6389840

    REDUCED by $70,000 (5.0%) on 04/03/2026

    For Sale O6389840 - 1849 WATERMERE LN, WINDERMERE, FL 34786 31 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3934
       Built: 2005
    Monthly Fee: $267
       Tax: $8,439 (2024)
    Community: Windermere Grande
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,230 (change assumption)
    Mortgage ($7,260) + Fees ($267) + Taxes in 2024 ($703)


    Taxes:$8,439

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 8259 MARITIME FLAG ST #4, WINDERMERE, FL 34786

    $320,000274 Days on yellowkey   MLS ID: O6329585

    1 Days Off yellowkey (back on 3/24/2026)

    For Sale O6329585 - 8259 MARITIME FLAG ST #4, WINDERMERE, FL 34786 34 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1460
       Built: 2011
    Monthly Fee: $459
       Tax: $4,052 (2024)
    Community: Lakeside Villas
    Condo


    Estimated Monthly Payment: $2,550 (change assumption)
    Mortgage ($1,753) + Fees ($459) + Taxes in 2024 ($338)


    Taxes:$4,052

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5151 LATROBE DR, WINDERMERE, FL 34786

    $4,100,00035 Days on yellowkey   MLS ID: O6392380

    For Sale O6392380 - 5151 LATROBE DR, WINDERMERE, FL 34786 57 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5301
       Built: 2000
    Monthly Fee: $1,224
       Tax: $23,020 (2025)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $25,608 (change assumption)
    Mortgage ($22,465) + Fees ($1,224) + Taxes in 2025 ($1,918)


    Taxes:$23,020

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6631 CRESTMONT GLEN LN, WINDERMERE, FL 34786

    $834,000289 Days on yellowkey   MLS ID: O6323076

    For Sale O6323076 - 6631 CRESTMONT GLEN LN, WINDERMERE, FL 34786 19 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3068
       Built: 2002
    Monthly Fee: $170
       Tax: $9,573 (2024)
    Community: Glenmuir
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,537 (change assumption)
    Mortgage ($4,570) + Fees ($170) + Taxes in 2024 ($798)


    Taxes:$9,573

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 6117 LOUISE COVE DR, WINDERMERE, FL 34786

    $5,250,000105 Days on yellowkey   MLS ID: O6372197

    For Sale O6372197 - 6117 LOUISE COVE DR, WINDERMERE, FL 34786 58 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5752
       Built: 2002
    Monthly Fee: $1,224
       Tax: $50,728 (2025)
    Community: Isleworth West
    Single Family


    Estimated Monthly Payment: $34,218 (change assumption)
    Mortgage ($28,766) + Fees ($1,224) + Taxes in 2025 ($4,227)


    Taxes:$50,728

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786

    $3,200,000274 Days on yellowkey   MLS ID: O6330108

    For Sale O6330108 - 4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786 44 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3745
       Built: 2006
    Monthly Fee: $1,146
       Tax: $33,607 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,480 (change assumption)
    Mortgage ($17,534) + Fees ($1,146) + Taxes in 2024 ($2,801)


    Taxes:$33,607

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9648 MCCORMICK PL, WINDERMERE, FL 34786

    $3,800,000210 Days on yellowkey   MLS ID: O6346918

    For Sale O6346918 - 9648 MCCORMICK PL, WINDERMERE, FL 34786 61 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4751
       Built: 1988
    Monthly Fee: $1,224
       Tax: $33,873 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $24,868 (change assumption)
    Mortgage ($20,821) + Fees ($1,224) + Taxes in 2024 ($2,823)


    Taxes:$33,873

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9731 CHESTNUT RIDGE DR, WINDERMERE, FL 34786

    $3,400,000251 Days on yellowkey   MLS ID: O6336655

    For Sale O6336655 - 9731 CHESTNUT RIDGE DR, WINDERMERE, FL 34786 57 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4877
       Built: 1986
    Monthly Fee: $1,224
       Tax: $19,867 (2024)
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $21,509 (change assumption)
    Mortgage ($18,630) + Fees ($1,224) + Taxes in 2024 ($1,656)


    Taxes:$19,867

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes 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.