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Windermere Single Family Homes For Sale - 260 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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  • 4474 BEGONIA CT, WINDERMERE, FL 34786

    $1,070,00083 Days on yellowkey   MLS ID: O6402227

    REDUCED by $50,000 (4.5%) on 07/14/2026

    For Sale O6402227 - 4474 BEGONIA CT, WINDERMERE, FL 34786 41 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4380
       Built: 1998
    Monthly Fee: $133
       Tax: $7,670 (2025)
    Community: Magnolia Park Windermere
    Single Family


    Estimated Monthly Payment: $6,635 (change assumption)
    Mortgage ($5,863) + Fees ($133) + Taxes in 2025 ($639)


    Taxes:$7,670

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786

    $3,350,000171 Days on yellowkey   MLS ID: O6377244

    REDUCED by $100,000 (2.9%) on 06/23/2026

    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: $20,800 (change assumption)
    Mortgage ($18,356) + 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


  • 2503 BUTLER BAY DR N, WINDERMERE, FL 34786

    $1,750,00044 Days on yellowkey   MLS ID: O6413242

    REDUCED by $49,000 (2.7%) on 07/13/2026

    For Sale O6413242 - 2503 BUTLER BAY DR N, WINDERMERE, FL 34786 98 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3297
       Built: 1990
    Monthly Fee: $199
       Tax: $16,376 (2025)
    Community: Windermere Club
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,152 (change assumption)
    Mortgage ($9,589) + Fees ($199) + Taxes in 2025 ($1,365)


    Taxes:$16,376

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 109 E 12TH AVE, WINDERMERE, FL 34786

    $1,195,00093 Days on yellowkey   MLS ID: O6394569

    REDUCED by $3,000 (0.3%) on 07/13/2026

    For Sale O6394569 - 109 E 12TH AVE, WINDERMERE, FL 34786 43 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2791
       Built: 1989   Tax: $18,865 (2025)
    Community: Windermere Town
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,120 (change assumption)
    Mortgage ($6,548) + Taxes in 2025 ($1,572)


    Taxes:$18,865

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 13845 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786

    $474,90014 Days on yellowkey   MLS ID: O6421552

    REDUCED by $14,100 (2.9%) on 07/14/2026

    For Sale O6421552 - 13845 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1636
       Built: 2015
    Monthly Fee: $71
       Tax: $7,026 (2025)
    Community: Summerport Trail Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,259 (change assumption)
    Mortgage ($2,602) + Fees ($71) + Taxes in 2025 ($586)


    Taxes:$7,026

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12826 WOODMERE CLOSE DR, WINDERMERE, FL 34786

    $650,00045 Days on yellowkey   MLS ID: O6412588

    REDUCED by $15,000 (2.3%) on 07/14/2026

    For Sale O6412588 - 12826 WOODMERE CLOSE DR, WINDERMERE, FL 34786 44 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2214
       Built: 2013
    Monthly Fee: $81
       Tax: $5,273 (2025)
    Community: Lake Sawyer South Ph 5
    Single Family


    Estimated Monthly Payment: $4,082 (change assumption)
    Mortgage ($3,562) + Fees ($81) + Taxes in 2025 ($439)


    Taxes:$5,273

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 10624 REAMS RD, WINDERMERE, FL 34786

    $475,000330 Days on yellowkey   MLS ID: O6338130

    0 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $12,000 (2.5%) on 05/28/2026

    For Sale O6338130 - 10624 REAMS RD, WINDERMERE, FL 34786 61 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2092
       Built: 2014
    Monthly Fee: $81
       Tax: $5,459 (2024)
    Community: Windermere Trls Ph 1C
    Single Family


    Estimated Monthly Payment: $3,139 (change assumption)
    Mortgage ($2,603) + Fees ($81) + Taxes in 2024 ($455)


    Taxes:$5,459

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 8662 ABBOTSBURY DR, WINDERMERE, FL 34786

    $500,00035 Days on yellowkey   MLS ID: O6416099

    0 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $25,000 (4.8%) on 06/30/2026

    For Sale O6416099 - 8662 ABBOTSBURY DR, WINDERMERE, FL 34786 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1877
       Built: 2004
    Monthly Fee: $170
       Tax: $2,511 (2025)
    Community: Lakes/Windermere-Peachtree
    Single Family


    Estimated Monthly Payment: $3,119 (change assumption)
    Mortgage ($2,740) + Fees ($170) + Taxes in 2025 ($209)


    Taxes:$2,511

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 14371 CREST PALM AVE, WINDERMERE, FL 34786

    $1,049,990102 Days on yellowkey   MLS ID: G5110664

    REDUCED by $64,999 (5.8%) on 06/17/2026

    For Sale G5110664 - 14371 CREST PALM AVE, WINDERMERE, FL 34786 42 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3100
       Built: 2025
    Monthly Fee: $245
       Tax: $1,309 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,107 (change assumption)
    Mortgage ($5,753) + Fees ($245) + Taxes in 2025 ($109)


    Taxes:$1,309

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 8316 LOOKOUT POINTE DR, WINDERMERE, FL 34786

    $1,075,00023 Days on yellowkey   MLS ID: S5152477

    For Sale S5152477 - 8316 LOOKOUT POINTE DR, WINDERMERE, FL 34786 74 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4332
       Built: 2016
    Monthly Fee: $8
       Tax: $14,774 (2026)
    Community: Windermere Trls Ph 3B
    Single Family


    Estimated Monthly Payment: $7,129 (change assumption)
    Mortgage ($5,890) + Fees ($8) + Taxes in 2026 ($1,231)


    Taxes:$14,774

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Horizon West Middle School


  • 7867 BERKSHIRE OAK ALY, WINDERMERE, FL 34786

    $519,00056 Days on yellowkey   MLS ID: S5149947

    REDUCED by $20,000 (3.7%) on 07/14/2026

    For Sale S5149947 - 7867 BERKSHIRE OAK ALY, WINDERMERE, FL 34786 39 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2221
       Built: 2017
    Monthly Fee: $133
       Tax: $7,755 (2025)
    Community: Westside Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,623 (change assumption)
    Mortgage ($2,844) + Fees ($133) + Taxes in 2025 ($646)


    Taxes:$7,755

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2512 TRYON PL, WINDERMERE, FL 34786

    $1,190,00014 Days on yellowkey   MLS ID: O6422154

    REDUCED by $40,000 (3.3%) on 07/14/2026

    For Sale O6422154 - 2512 TRYON PL, WINDERMERE, FL 34786 69 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3478
       Built: 1989
    Monthly Fee: $60
       Tax: $6,180 (2025)
    Community: Manors At Butler Bay Ph 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,095 (change assumption)
    Mortgage ($6,520) + Fees ($60) + Taxes in 2025 ($515)


    Taxes:$6,180

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 13303 PENSHURST LN, WINDERMERE, FL 34786

    $669,9004 Days on yellowkey   MLS ID: O6423867

    For Sale O6423867 - 13303 PENSHURST LN, WINDERMERE, FL 34786 13 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2959
       Built: 2015   Tax: $8,999 (2025)
    Community: Windermere Sound
    Single Family


    Estimated Monthly Payment: $4,421 (change assumption)
    Mortgage ($3,671) + Taxes in 2025 ($750)


    Taxes:$8,999

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13328 OVERSTREET RD, WINDERMERE, FL 34786

    $639,9007 Days on yellowkey   MLS ID: O6423949

    For Sale O6423949 - 13328 OVERSTREET RD, WINDERMERE, FL 34786 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2648
       Built: 2014
    Monthly Fee: $81
       Tax: $5,013 (2025)
    Community: Lake Sawyer South
    Single Family


    Estimated Monthly Payment: $4,005 (change assumption)
    Mortgage ($3,506) + Fees ($81) + Taxes in 2025 ($418)


    Taxes:$5,013

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 12912 DROXFORD RD, WINDERMERE, FL 34786

    $650,00014 Days on yellowkey   MLS ID: O6422064

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6422064 - 12912 DROXFORD RD, WINDERMERE, FL 34786 52 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2966
       Built: 2006
    Monthly Fee: $82
       Tax: $9,868 (2025)
    Community: Lakes/Windermere Ph 02A
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,466 (change assumption)
    Mortgage ($3,562) + Fees ($82) + Taxes in 2025 ($822)


    Taxes:$9,868

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 1238 LAKE WHITNEY DR, WINDERMERE, FL 34786

    $2,099,90017 Days on yellowkey   MLS ID: O6421211

    FORECLOSURE O6421211 - 1238 LAKE WHITNEY DR, WINDERMERE, FL 34786 55 photos

    Bed: 4   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5515
       Built: 2005
    Monthly Fee: $203
       Tax: $34,190 (2025)
    Community: Reserve At Belmere Ph 02 48 144
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,558 (change assumption)
    Mortgage ($11,506) + Fees ($203) + Taxes in 2025 ($2,849)


    Taxes:$34,190

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 5067 SAWYER COVE WAY, WINDERMERE, FL 34786

    $2,100,00045 Days on yellowkey   MLS ID: O6409382

    For Sale O6409382 - 5067 SAWYER COVE WAY, WINDERMERE, FL 34786 70 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3567
       Built: 2018
    Monthly Fee: $287
       Tax: $21,824 (2025)
    Community: Sawyer Sound
    Single Family


    Estimated Monthly Payment: $13,612 (change assumption)
    Mortgage ($11,507) + Fees ($287) + Taxes in 2025 ($1,819)


    Taxes:$21,824

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13118 SUNKISS LOOP, WINDERMERE, FL 34786

    $560,000137 Days on yellowkey   MLS ID: O6385211

    0 Days Off yellowkey (back on 7/13/2026)

    REDUCED by $10,000 (1.8%) on 07/06/2026

    For Sale O6385211 - 13118 SUNKISS LOOP, WINDERMERE, FL 34786 52 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2547
       Built: 2005
    Monthly Fee: $130
       Tax: $7,821 (2024)
    Community: Summerport Ph 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,850 (change assumption)
    Mortgage ($3,068) + Fees ($130) + Taxes in 2024 ($652)


    Taxes:$7,821

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 1136 LAKE WHITNEY DR, WINDERMERE, FL 34786

    $2,225,00072 Days on yellowkey   MLS ID: O6405536

    0 Days Off yellowkey (back on 7/13/2026)

    REDUCED by $70,000 (3.1%) on 06/22/2026

    For Sale O6405536 - 1136 LAKE WHITNEY DR, WINDERMERE, FL 34786 87 photos

    Bed: 4   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5722
       Built: 2006
    Monthly Fee: $203
       Tax: $24,153 (2025)
    Community: Reserve At Belmere Ph 02 48 144
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,407 (change assumption)
    Mortgage ($12,191) + Fees ($203) + Taxes in 2025 ($2,013)


    Taxes:$24,153

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 13013 OVERSTREET RD, WINDERMERE, FL 34786

    $639,994141 Days on yellowkey   MLS ID: O6380917

    REDUCED by $10,000 (1.5%) on 06/17/2026

    For Sale O6380917 - 13013 OVERSTREET RD, WINDERMERE, FL 34786 47 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2053
       Built: 2009
    Monthly Fee: $82
       Tax: $3,146 (2024)
    Community: Lakes/Windermere
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,851 (change assumption)
    Mortgage ($3,507) + Fees ($82) + Taxes in 2024 ($262)


    Taxes:$3,146

    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.