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Windermere Single Family Homes For Sale - 227 homes

Windermere Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Windermere with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Windermere single family houses.

Location: Windermere

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  • 10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786

    $3,500,00077 Days on yellowkey   MLS ID: O6377244

    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: $21,622 (change assumption)
    Mortgage ($19,178) + 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


  • 13734 LAKE CAWOOD DR, WINDERMERE, FL 34786

    $1,390,00069 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


  • 11208 LEDGEMENT LN, WINDERMERE, FL 34786

    $1,000,000196 Days on yellowkey   MLS ID: O6325096

    For Sale O6325096 - 11208 LEDGEMENT LN, WINDERMERE, FL 34786 36 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2988
       Built: 2002
    Monthly Fee: $140
       Tax: $6,561 (2024)
    Community: Glenmuir 48 39
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,166 (change assumption)
    Mortgage ($5,479) + Fees ($140) + Taxes in 2024 ($547)


    Taxes:$6,561

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 6799 HELMSLEY CIR, WINDERMERE, FL 34786

    $658,000148 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


  • 2806 WINDSOR HILL DR, WINDERMERE, FL 34786

    $1,150,0005 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


  • 12863 HOLDENBURY LN, WINDERMERE, FL 34786

    $539,00020 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


  • 13312 LONGACRE DR, WINDERMERE, FL 34786

    $534,90098 Days on yellowkey   MLS ID: S5141031

    REDUCED by $9,000 (1.7%) on 04/06/2026

    For Sale S5141031 - 13312 LONGACRE DR, WINDERMERE, FL 34786 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 2013
    Monthly Fee: $120
       Tax: $7,533 (2024)
    Community: Windermere Terrace
    Single Family


    Estimated Monthly Payment: $3,679 (change assumption)
    Mortgage ($2,931) + Fees ($120) + Taxes in 2024 ($628)


    Taxes:$7,533

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 801 W 2ND AVE, WINDERMERE, FL 34786

    $3,995,00083 Days on yellowkey   MLS ID: O6375693

    For Sale O6375693 - 801 W 2ND AVE, WINDERMERE, FL 34786 44 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5639
       Built: 2008   Tax: $49,401 (2024)
    Community: Aladar On Lake Butler
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $26,007 (change assumption)
    Mortgage ($21,890) + Taxes in 2024 ($4,117)


    Taxes:$49,401

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 3130 BUTLER BAY DR N, WINDERMERE, FL 34786

    $1,725,00011 Days on yellowkey   MLS ID: O6395307

    For Sale O6395307 - 3130 BUTLER BAY DR N, WINDERMERE, FL 34786 51 photos

    Bed: 5   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 4490
       Built: 1985
    Monthly Fee: $181
       Tax: $21,502 (2025)
    Community: Butler Bay
    Single Family


    Estimated Monthly Payment: $11,425 (change assumption)
    Mortgage ($9,452) + Fees ($181) + Taxes in 2025 ($1,792)


    Taxes:$21,502

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6152 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786

    $1,130,0006 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


  • 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786

    $2,499,000207 Days on yellowkey   MLS ID: O6344907

    For Sale O6344907 - 6102 S HAMPSHIRE CT, WINDERMERE, FL 34786 26 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


  • 1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786

    $2,380,00015 Days on yellowkey   MLS ID: S5146178

    For Sale S5146178 - 1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786 63 photos

    Bed: 5   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 5108
       Built: 2019
    Monthly Fee: $250
       Tax: $1,982 (2025)
    Community: Estancia/Windermere
    Single Family


    Estimated Monthly Payment: $13,456 (change assumption)
    Mortgage ($13,041) + Fees ($250) + Taxes in 2025 ($165)


    Taxes:$1,982

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5145 LATROBE DR, WINDERMERE, FL 34786

    $3,449,00058 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

    $1,199,00011 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


  • 1849 WATERMERE LN, WINDERMERE, FL 34786

    $1,325,00031 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


  • 5151 LATROBE DR, WINDERMERE, FL 34786

    $4,100,00025 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


  • 11578 ASHLIN PARK BLVD, WINDERMERE, FL 34786

    $619,90089 Days on yellowkey   MLS ID: O6373714

    For Sale O6373714 - 11578 ASHLIN PARK BLVD, WINDERMERE, FL 34786 58 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2396
       Built: 2016
    Monthly Fee: $107
       Tax: $9,270 (2025)
    Community: Ashlin Park Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,276 (change assumption)
    Mortgage ($3,397) + Fees ($107) + Taxes in 2025 ($772)


    Taxes:$9,270

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6631 CRESTMONT GLEN LN, WINDERMERE, FL 34786

    $834,000279 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


  • 1329 GLENHEATHER DR, WINDERMERE, FL 34786

    $821,0008 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


  • 6117 LOUISE COVE DR, WINDERMERE, FL 34786

    $5,250,00095 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




Why Bother Searching Elsewhere for Windermere Single Family Homes for Sale?

Windermere home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Windermere . You can use our website to view Multiple Listing Service (MLS) data on Windermere single family homes. 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 single family home 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.