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Windermere Single Family Homes For Sale - 242 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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  • 2806 WINDSOR HILL DR, WINDERMERE, FL 34786

    $1,150,0008 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


  • 10870 BAYSHORE DR, WINDERMERE, FL 34786

    $2,995,00077 Days on yellowkey   MLS ID: O6371471

    For Sale O6371471 - 10870 BAYSHORE DR, WINDERMERE, FL 34786 60 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4693
       Built: 1999   Tax: $27,527 (2024)
    Community: Lake Down Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $18,704 (change assumption)
    Mortgage ($16,411) + Taxes in 2024 ($2,294)


    Taxes:$27,527

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 8520 GREENBANK BLVD, WINDERMERE, FL 34786

    $549,9009 Days on yellowkey   MLS ID: O6396673

    For Sale O6396673 - 8520 GREENBANK BLVD, WINDERMERE, FL 34786 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1726
       Built: 2004
    Monthly Fee: $170
       Tax: $6,960 (2025)
    Community: Lakes/Windermere-Peachtree
    Single Family


    Estimated Monthly Payment: $3,763 (change assumption)
    Mortgage ($3,013) + Fees ($170) + Taxes in 2025 ($580)


    Taxes:$6,960

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11162 LEDGEMENT LN, WINDERMERE, FL 34786

    $995,000184 Days on yellowkey   MLS ID: O6346461

    For Sale O6346461 - 11162 LEDGEMENT LN, WINDERMERE, FL 34786 55 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3248
       Built: 2002
    Monthly Fee: $170
       Tax: $7,747 (2024)
    Community: Glenmuir Ut 02 51 42
    Single Family


    Estimated Monthly Payment: $6,268 (change assumption)
    Mortgage ($5,452) + Fees ($170) + Taxes in 2024 ($646)


    Taxes:$7,747

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 13243 CHARFIELD ST, WINDERMERE, FL 34786

    $699,00050 Days on yellowkey   MLS ID: O6385405

    For Sale O6385405 - 13243 CHARFIELD ST, WINDERMERE, FL 34786 39 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2794
       Built: 2010
    Monthly Fee: $81
       Tax: $6,403 (2024)
    Community: Lake Sawyer South Ph 02
    Single Family


    Estimated Monthly Payment: $4,445 (change assumption)
    Mortgage ($3,830) + Fees ($81) + Taxes in 2024 ($534)


    Taxes:$6,403

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6857 VALHALLA WAY, WINDERMERE, FL 34786

    $3,700,0003 Days on yellowkey   MLS ID: S5147781

    For Sale S5147781 - 6857 VALHALLA WAY, WINDERMERE, FL 34786 90 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 7153
       Built: 2006
    Monthly Fee: $298
       Tax: $35,537 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,533 (change assumption)
    Mortgage ($20,273) + Fees ($298) + Taxes in 2025 ($2,961)


    Taxes:$35,537

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1002 OAKDALE ST, WINDERMERE, FL 34786

    $975,0003 Days on yellowkey   MLS ID: TB8495717

    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: $6,076 (change assumption)
    Mortgage ($5,342) + Taxes in 2025 ($733)


    Taxes:$8,799

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13609 ANCILLA BLVD, WINDERMERE, FL 34786

    $749,99963 Days on yellowkey   MLS ID: O6381542

    REDUCED by $39,001 (4.9%) on 04/14/2026

    For Sale O6381542 - 13609 ANCILLA BLVD, WINDERMERE, FL 34786 56 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3360
       Built: 2005
    Monthly Fee: $130
       Tax: $9,521 (2024)
    Community: Summerport Ph 03
    Single Family


    Estimated Monthly Payment: $5,033 (change assumption)
    Mortgage ($4,109) + Fees ($130) + Taxes in 2024 ($793)


    Taxes:$9,521

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 4301 DOWN POINT LN, WINDERMERE, FL 34786

    $2,950,0006 Days on yellowkey   MLS ID: O6398366

    For Sale O6398366 - 4301 DOWN POINT LN, WINDERMERE, FL 34786 61 photos

    Bed: 5   Bath: 4.0   Gar: 6
    Liv Area Sq Ft: 7153
       Built: 1983   Tax: $19,012 (2025)
    Community: Down Point Sub
    Single Family


    Estimated Monthly Payment: $17,748 (change assumption)
    Mortgage ($16,164) + Taxes in 2025 ($1,584)


    Taxes:$19,012

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 8411 WOBURN CT, WINDERMERE, FL 34786

    $1,260,00022 Days on yellowkey   MLS ID: O6391980

    For Sale O6391980 - 8411 WOBURN CT, WINDERMERE, FL 34786 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2582
       Built: 1999
    Monthly Fee: $222
       Tax: $12,964 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,206 (change assumption)
    Mortgage ($6,904) + Fees ($222) + Taxes in 2025 ($1,080)


    Taxes:$12,964

    Elementary School: Windermere Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 6310 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786

    $490,000115 Days on yellowkey   MLS ID: O6368983

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

    For Sale O6368983 - 6310 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786 15 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1977
       Built: 2012
    Monthly Fee: $125
       Tax: $7,927 (2024)
    Community: Windermere Lndgs Ph 02
    Single Family


    Estimated Monthly Payment: $3,470 (change assumption)
    Mortgage ($2,685) + Fees ($125) + Taxes in 2024 ($661)


    Taxes:$7,927

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11608 CLAYMONT CIRCLE, WINDERMERE, FL 34786

    $1,299,00036 Days on yellowkey   MLS ID: O6390072

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

    For Sale O6390072 - 11608 CLAYMONT CIRCLE, WINDERMERE, FL 34786 44 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2614
       Built: 2004
    Monthly Fee: $298
       Tax: $7,193 (2025)
    Community: Keenes Pointe Ut 04 Sec 31 48 82
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,015 (change assumption)
    Mortgage ($7,118) + Fees ($298) + Taxes in 2025 ($599)


    Taxes:$7,193

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5018 RIVER GEM AVE, WINDERMERE, FL 34786

    $775,00079 Days on yellowkey   MLS ID: TB8469061

    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


  • 6752 TRELLIS VINE LOOP, WINDERMERE, FL 34786

    $1,000,00084 Days on yellowkey   MLS ID: O6376318

    For Sale O6376318 - 6752 TRELLIS VINE LOOP, WINDERMERE, FL 34786 30 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3820
       Built: 2018
    Monthly Fee: $200
       Tax: $10,983 (2024)
    Community: Windstone
    Single Family


    Estimated Monthly Payment: $6,595 (change assumption)
    Mortgage ($5,479) + Fees ($200) + Taxes in 2024 ($915)


    Taxes:$10,983

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 11226 MACAW CT, WINDERMERE, FL 34786

    $1,825,0004 Days on yellowkey   MLS ID: O6393210

    For Sale O6393210 - 11226 MACAW CT, WINDERMERE, FL 34786 77 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4549
       Built: 2004
    Monthly Fee: $283
       Tax: $19,332 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,894 (change assumption)
    Mortgage ($10,000) + Fees ($283) + Taxes in 2025 ($1,611)


    Taxes:$19,332

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12411 MONTALCINO CIR, WINDERMERE, FL 34786

    $1,550,0004 Days on yellowkey   MLS ID: O6398677

    For Sale O6398677 - 12411 MONTALCINO CIR, WINDERMERE, FL 34786 65 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3399
       Built: 2011
    Monthly Fee: $150
       Tax: $11,027 (2025)
    Community: Casa Del Lago
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,562 (change assumption)
    Mortgage ($8,493) + Fees ($150) + Taxes in 2025 ($919)


    Taxes:$11,027

    Elementary School: Sunset Park Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 825 OAKDALE ST, WINDERMERE, FL 34786

    $792,50010 Days on yellowkey   MLS ID: O6396351

    2 Days Off yellowkey (back on 4/13/2026)

    For Sale O6396351 - 825 OAKDALE ST, WINDERMERE, FL 34786 50 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1664
       Built: 1935   Tax: $9,799 (2025)
    Community: Windermere Town
    Single Family


    Estimated Monthly Payment: $5,159 (change assumption)
    Mortgage ($4,342) + Taxes in 2025 ($817)


    Taxes:$9,799

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786

    $3,500,00080 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


  • 8648 POWDER RIDGE TRL, WINDERMERE, FL 34786

    $499,00087 Days on yellowkey   MLS ID: O6373065

    REDUCED by $17,000 (3.3%) on 04/13/2026

    For Sale O6373065 - 8648 POWDER RIDGE TRL, WINDERMERE, FL 34786 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1876
       Built: 2014
    Monthly Fee: $81
       Tax: $6,733 (2025)
    Community: Windermere Trls Ph 1C
    Single Family


    Estimated Monthly Payment: $3,376 (change assumption)
    Mortgage ($2,734) + Fees ($81) + Taxes in 2025 ($561)


    Taxes:$6,733

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6957 NORTHWICH DR, WINDERMERE, FL 34786

    $585,000108 Days on yellowkey   MLS ID: A4676454

    For Sale A4676454 - 6957 NORTHWICH DR, WINDERMERE, FL 34786 22 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2667
       Built: 2007
    Monthly Fee: $100
       Tax: $8,184 (2024)
    Community: Lakes/Windermere Ph 04
    Single Family


    Estimated Monthly Payment: $3,987 (change assumption)
    Mortgage ($3,205) + Fees ($100) + Taxes in 2024 ($682)


    Taxes:$8,184

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School




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.