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Windermere Homes For Sale & Real Estate - 333 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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  • 6442 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786

    $575,000164 Days on yellowkey   MLS ID: G5106279

    REDUCED by $10,000 (1.7%) on 05/20/2026

    SHORT SALE G5106279 - 6442 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2139
       Built: 2012
    Monthly Fee: $125
       Tax: $7,649 (2024)
    Community: Windermere Lndgs Ph 02
    Single Family


    Estimated Monthly Payment: $3,913 (change assumption)
    Mortgage ($3,151) + Fees ($125) + Taxes in 2024 ($637)


    Taxes:$7,649

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11753 VINCI DR, WINDERMERE, FL 34786

    $2,150,00049 Days on yellowkey   MLS ID: O6404892

    1 Days Off yellowkey (back on 5/20/2026)

    For Sale O6404892 - 11753 VINCI DR, WINDERMERE, FL 34786 52 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4037
       Built: 2012
    Monthly Fee: $298
       Tax: $22,953 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,991 (change assumption)
    Mortgage ($11,781) + Fees ($298) + Taxes in 2025 ($1,913)


    Taxes:$22,953

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9648 MCCORMICK PL, WINDERMERE, FL 34786

    $3,800,000270 Days on yellowkey   MLS ID: O6346918

    1 Days Off yellowkey (back on 5/20/2026)

    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


  • 1925 BREEZY HILL DRIVE WINDERMERE FLORIDA 34786, WINDERMERE, FL 34786

    $862,00069 Days on yellowkey   MLS ID: O6398784

    1 Days Off yellowkey (back on 5/20/2026)

    REDUCED by $18,000 (2.0%) on 05/15/2026

    For Sale O6398784 - 1925 BREEZY HILL DRIVE WINDERMERE FLORIDA 34786, WINDERMERE, FL 34786 39 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3063
       Built: 2001
    Monthly Fee: $115
       Tax: $6,661 (2025)
    Community: Westover Club Ph 1 Rep
    Single Family


    Estimated Monthly Payment: $5,393 (change assumption)
    Mortgage ($4,723) + Fees ($115) + Taxes in 2025 ($555)


    Taxes:$6,661

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 1028 LASCALA DR, WINDERMERE, FL 34786

    $749,00063 Days on yellowkey   MLS ID: O6400649

    2 Days Off yellowkey (back on 5/20/2026)

    For Sale O6400649 - 1028 LASCALA DR, WINDERMERE, FL 34786 60 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2208
       Built: 2002
    Monthly Fee: $140
       Tax: $8,185 (2025)
    Community: Belmere Village G2 48 65
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,926 (change assumption)
    Mortgage ($4,104) + Fees ($140) + Taxes in 2025 ($682)


    Taxes:$8,185

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 4806 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786

    $4,200,00035 Days on yellowkey   MLS ID: O6408804

    0 Days Off yellowkey (back on 5/19/2026)

    For Sale O6408804 - 4806 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786 67 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 5695
       Built: 2008
    Monthly Fee: $1,224
       Tax: $41,679 (2025)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,710 (change assumption)
    Mortgage ($23,013) + Fees ($1,224) + Taxes in 2025 ($3,473)


    Taxes:$41,679

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 4948 WISE BIRD DR, WINDERMERE, FL 34786

    $679,00040 Days on yellowkey   MLS ID: O6405511

    0 Days Off yellowkey (back on 5/19/2026)

    For Sale O6405511 - 4948 WISE BIRD DR, WINDERMERE, FL 34786 54 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 2003
    Monthly Fee: $130
       Tax: $8,593 (2025)
    Community: Summerport
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,567 (change assumption)
    Mortgage ($3,720) + Fees ($130) + Taxes in 2025 ($716)


    Taxes:$8,593

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 84 OAKDALE ST, WINDERMERE, FL 34786

    $1,875,000162 Days on yellowkey   MLS ID: O6372842

    1 Days Off yellowkey (back on 5/19/2026)

    For Sale O6372842 - 84 OAKDALE ST, WINDERMERE, FL 34786 52 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3519
       Built: 2020   Tax: $12,265 (2024)
    Community: Davis Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,296 (change assumption)
    Mortgage ($10,274) + Taxes in 2024 ($1,022)


    Taxes:$12,265

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 13304 BELLARIA CIR, WINDERMERE, FL 34786

    $2,798,00085 Days on yellowkey   MLS ID: O6391558

    REDUCED by $70,000 (2.4%) on 05/19/2026

    For Sale O6391558 - 13304 BELLARIA CIR, WINDERMERE, FL 34786 69 photos

    Bed: 6   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4920
       Built: 2013
    Monthly Fee: $483
       Tax: $30,699 (2025)
    Community: Bellaria
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $18,372 (change assumption)
    Mortgage ($15,331) + Fees ($483) + Taxes in 2025 ($2,558)


    Taxes:$30,699

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1330 LAKE OLIVIA, WINDERMERE, FL 34786

    $5,500,00089 Days on yellowkey   MLS ID: S5144942

    For Sale S5144942 - 1330 LAKE OLIVIA, WINDERMERE, FL 34786 13 photos

    Bed: 6   Bath: 7.0   Gar: 4
    Liv Area Sq Ft: 6442
       Built: 2026
    Monthly Fee: $400
       Tax: $9,870 (2024)
    Community: Lake Olivia Reserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,359 (change assumption)
    Mortgage ($30,136) + Fees ($400) + Taxes in 2024 ($823)


    Taxes:$9,870

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 8340 LAKE BURDEN CIR, WINDERMERE, FL 34786

    $3,250,00043 Days on yellowkey   MLS ID: O6406513

    0 Days Off yellowkey (back on 5/18/2026)

    For Sale O6406513 - 8340 LAKE BURDEN CIR, WINDERMERE, FL 34786 71 photos

    Bed: 6   Bath: 6.0   Gar: 4
    Liv Area Sq Ft: 6848
       Built: 2008
    Monthly Fee: $298
       Tax: $28,798 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $20,506 (change assumption)
    Mortgage ($17,808) + Fees ($298) + Taxes in 2025 ($2,400)


    Taxes:$28,798

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13339 ROSKIN LN, WINDERMERE, FL 34786

    $680,000164 Days on yellowkey   MLS ID: S5141148

    For Sale S5141148 - 13339 ROSKIN LN, WINDERMERE, FL 34786 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2947
       Built: 2012
    Monthly Fee: $82
       Tax: $8,674 (2024)
    Community: Lake Sawyer South Ph 01
    Single Family


    Estimated Monthly Payment: $4,531 (change assumption)
    Mortgage ($3,726) + Fees ($82) + Taxes in 2024 ($723)


    Taxes:$8,674

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 11923 LAKE BUTLER BLVD, WINDERMERE, FL 34786

    $1,630,000390 Days on yellowkey   MLS ID: O6311003

    For Sale O6311003 - 11923 LAKE BUTLER BLVD, WINDERMERE, FL 34786 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2238
       Built: 1985   Tax: $12,907 (2024)
    Community: Lake Butler Estates
    Single Family


    Estimated Monthly Payment: $10,007 (change assumption)
    Mortgage ($8,931) + Taxes in 2024 ($1,076)


    Taxes:$12,907

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 12533 CRAGSIDE LN, WINDERMERE, FL 34786

    $575,00046 Days on yellowkey   MLS ID: O6405628

    For Sale O6405628 - 12533 CRAGSIDE LN, WINDERMERE, FL 34786 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2151
       Built: 2004
    Monthly Fee: $82
       Tax: $8,484 (2025)
    Community: Lakes Windermere Ph 01 49 108
    Single Family


    Estimated Monthly Payment: $3,940 (change assumption)
    Mortgage ($3,151) + Fees ($82) + Taxes in 2025 ($707)


    Taxes:$8,484

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11636 WATER RUN ALY, WINDERMERE, FL 34786

    $408,000249 Days on yellowkey   MLS ID: S5136888

    REDUCED by $17,000 (4.0%) on 05/06/2026

    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: $3,037 (change assumption)
    Mortgage ($2,236) + Fees ($332) + Taxes in 2024 ($469)


    Taxes:$5,634

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5145 LATROBE DR, WINDERMERE, FL 34786

    $3,299,000128 Days on yellowkey   MLS ID: O6382287

    REDUCED by $150,000 (4.3%) on 05/17/2026

    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: $21,615 (change assumption)
    Mortgage ($18,076) + 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


  • 14341 CREST PALM AVE, WINDERMERE, FL 34786

    $1,130,64338 Days on yellowkey   MLS ID: G5112469

    For Sale G5112469 - 14341 CREST PALM AVE, WINDERMERE, FL 34786 1 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3153
       Built: 2026
    Monthly Fee: $245
       Tax: $1,309 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,549 (change assumption)
    Mortgage ($6,195) + 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


  • 12863 HOLDENBURY LN, WINDERMERE, FL 34786

    $539,00090 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


  • 8179 MARITIME FLAG ST #101, WINDERMERE, FL 34786

    $325,00068 Days on yellowkey   MLS ID: O6399551

    0 Days Off yellowkey (back on 5/16/2026)

    REDUCED by $5,000 (1.5%) on 05/05/2026

    For Sale O6399551 - 8179 MARITIME FLAG ST #101, WINDERMERE, FL 34786 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1442
       Built: 2006   Tax: $4,106 (2025)
    Community: Lakeside/Lks/Windermere
    Condo


    Estimated Monthly Payment: $2,123 (change assumption)
    Mortgage ($1,781) + Taxes in 2025 ($342)


    Taxes:$4,106

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2219 RIDGEWIND WAY, WINDERMERE, FL 34786

    $1,299,00065 Days on yellowkey   MLS ID: O6400508

    1 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $50,000 (3.7%) on 05/04/2026

    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: $8,171 (change assumption)
    Mortgage ($7,118) + 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




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.