REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Windermere Homes For Sale & Real Estate - 314 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

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

    $360,00057 Days on yellowkey   MLS ID: O6396784

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

    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


  • 2127 LILYPAD LN, WINDERMERE, FL 34786

    $1,250,00032 Days on yellowkey   MLS ID: O6403899

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

    For Sale O6403899 - 2127 LILYPAD LN, WINDERMERE, FL 34786 60 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3349
       Built: 1989
    Monthly Fee: $122
       Tax: $10,870 (2025)
    Community: Willows At Lake Rhea Ph 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,877 (change assumption)
    Mortgage ($6,849) + Fees ($122) + Taxes in 2025 ($906)


    Taxes:$10,870

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 81 OAKDALE ST, WINDERMERE, FL 34786

    $2,300,000197 Days on yellowkey   MLS ID: S5138567

    For Sale S5138567 - 81 OAKDALE ST, WINDERMERE, FL 34786 87 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4284
       Built: 2001   Tax: $24,940 (2025)
    Community: Davis Shores
    Single Family


    Estimated Monthly Payment: $14,681 (change assumption)
    Mortgage ($12,602) + Taxes in 2025 ($2,078)


    Taxes:$24,940

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786

    $322,000138 Days on yellowkey   MLS ID: TB8465266

    REDUCED by $3,000 (0.9%) on 05/14/2026

    For Sale TB8465266 - 8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786 70 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1442
       Built: 2006   Tax: $4,422 (2024)
    Community: Lakeside/Lks/Windermere Ph 3
    Condo


    Estimated Monthly Payment: $2,133 (change assumption)
    Mortgage ($1,764) + Taxes in 2024 ($368)


    Taxes:$4,422

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 8866 HERENCIA ALY, WINDERMERE, FL 34786

    $430,00020 Days on yellowkey   MLS ID: O6407518

    For Sale O6407518 - 8866 HERENCIA ALY, WINDERMERE, FL 34786 31 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1577
       Built: 2021
    Monthly Fee: $240
       Tax: $5,532 (2025)
    Community: Legado 95/47 Lot 100
    Townhouse


    Estimated Monthly Payment: $3,057 (change assumption)
    Mortgage ($2,356) + Fees ($240) + Taxes in 2025 ($461)


    Taxes:$5,532

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13609 ANCILLA BLVD, WINDERMERE, FL 34786

    $749,999109 Days on yellowkey   MLS ID: O6381542

    0 Days Off yellowkey (back on 5/12/2026)

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

    For Sale O6381542 - 13609 ANCILLA BLVD, WINDERMERE, FL 34786 66 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


  • 8648 POWDER RIDGE TRL, WINDERMERE, FL 34786

    $499,000133 Days on yellowkey   MLS ID: O6373065

    1 Days Off yellowkey (back on 5/13/2026)

    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


  • 606 E 6TH AVE, WINDERMERE, FL 34786

    $2,350,00076 Days on yellowkey   MLS ID: O6390327

    2 Days Off yellowkey (back on 5/13/2026)

    For Sale O6390327 - 606 E 6TH AVE, WINDERMERE, FL 34786 42 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4471
       Built: 2016   Tax: $25,043 (2025)
    Community: Diamondhead
    Single Family


    Estimated Monthly Payment: $14,963 (change assumption)
    Mortgage ($12,876) + Taxes in 2025 ($2,087)


    Taxes:$25,043

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 7503 LAKE ALBERT DR, WINDERMERE, FL 34786

    $1,650,00025 Days on yellowkey   MLS ID: S5149564

    3 Days Off yellowkey (back on 5/11/2026)

    For Sale S5149564 - 7503 LAKE ALBERT DR, WINDERMERE, FL 34786 77 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4329
       Built: 2015
    Monthly Fee: $180
       Tax: $17,734 (2025)
    Community: Lake Burden South Phase 1
    Single Family


    Estimated Monthly Payment: $10,699 (change assumption)
    Mortgage ($9,041) + Fees ($180) + Taxes in 2025 ($1,478)


    Taxes:$17,734

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 1515 LAKE WHITNEY DR, WINDERMERE, FL 34786

    $1,350,00026 Days on yellowkey   MLS ID: O6405903

    0 Days Off yellowkey (back on 5/12/2026)

    For Sale O6405903 - 1515 LAKE WHITNEY DR, WINDERMERE, FL 34786 73 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3931
       Built: 2005
    Monthly Fee: $272
       Tax: $12,979 (2025)
    Community: Reserve At Belmere 48 23
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,751 (change assumption)
    Mortgage ($7,397) + Fees ($272) + Taxes in 2025 ($1,082)


    Taxes:$12,979

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 2635 TRYON PL, WINDERMERE, FL 34786

    $1,475,00028 Days on yellowkey   MLS ID: O6402029

    0 Days Off yellowkey (back on 5/12/2026)

    For Sale O6402029 - 2635 TRYON PL, WINDERMERE, FL 34786 73 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4027
       Built: 1997
    Monthly Fee: $60
       Tax: $8,425 (2026)
    Community: Manors At Butler Bay
    Single Family


    Estimated Monthly Payment: $8,844 (change assumption)
    Mortgage ($8,082) + Fees ($60) + Taxes in 2026 ($702)


    Taxes:$8,425

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2026

    Middle School: Gotha Middle


  • 6001 CAYMUS LOOP, WINDERMERE, FL 34786

    $1,599,000119 Days on yellowkey   MLS ID: O6379564

    0 Days Off yellowkey (back on 2/10/2026)

    For Sale O6379564 - 6001 CAYMUS LOOP, WINDERMERE, FL 34786 44 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3520
       Built: 2005
    Monthly Fee: $298
       Tax: $9,709 (2024)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,869 (change assumption)
    Mortgage ($8,761) + Fees ($298) + Taxes in 2024 ($809)


    Taxes:$9,709

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 5603 MARLEON DR, WINDERMERE, FL 34786

    $27,000,00022 Days on yellowkey   MLS ID: O6404938

    For Sale O6404938 - 5603 MARLEON DR, WINDERMERE, FL 34786 92 photos

    Bed: 7   Bath: 9.0   Gar: 10
    Liv Area Sq Ft: 22108
       Built: 2008   Tax: $138,635 (2025)
    Community: Na
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $159,494 (change assumption)
    Mortgage ($147,942) + Taxes in 2025 ($11,553)


    Taxes:$138,635

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3413 LILAS CT, WINDERMERE, FL 34786

    $1,975,00022 Days on yellowkey   MLS ID: O6401129

    0 Days Off yellowkey (back on 5/11/2026)

    For Sale O6401129 - 3413 LILAS CT, WINDERMERE, FL 34786 53 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5084
       Built: 1996
    Monthly Fee: $687
       Tax: $27,450 (2025)
    Community: Chaine De Lac
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,796 (change assumption)
    Mortgage ($10,822) + Fees ($687) + Taxes in 2025 ($2,288)


    Taxes:$27,450

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5421 TILDENS GROVE BLVD, WINDERMERE, FL 34786

    $1,999,90032 Days on yellowkey   MLS ID: O6402594

    For Sale O6402594 - 5421 TILDENS GROVE BLVD, WINDERMERE, FL 34786 66 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5922
       Built: 2005
    Monthly Fee: $317
       Tax: $17,783 (2025)
    Community: Tildens Grove
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,757 (change assumption)
    Mortgage ($10,958) + Fees ($317) + Taxes in 2025 ($1,482)


    Taxes:$17,783

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12333 VIA DERNA PL, WINDERMERE, FL 34786

    $458,000188 Days on yellowkey   MLS ID: O6362685

    REDUCED by $1,000 (0.2%) on 05/11/2026

    For Sale O6362685 - 12333 VIA DERNA PL, WINDERMERE, FL 34786 57 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1919
       Built: 2014
    Monthly Fee: $316
       Tax: $6,305 (2024)
    Community: Carrington
    Townhouse


    Estimated Monthly Payment: $3,351 (change assumption)
    Mortgage ($2,510) + Fees ($316) + Taxes in 2024 ($525)


    Taxes:$6,305

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 713 MAIN ST, WINDERMERE, FL 34786

    $2,175,000166 Days on yellowkey   MLS ID: O6368185

    REDUCED by $60,000 (2.7%) on 05/11/2026

    For Sale O6368185 - 713 MAIN ST, WINDERMERE, FL 34786 82 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 5031
       Built: 2013   Tax: $9,559 (2025)
    Community: Windermere
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,714 (change assumption)
    Mortgage ($11,918) + Taxes in 2025 ($797)


    Taxes:$9,559

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 11686 WATER RUN ALY, WINDERMERE, FL 34786

    $409,90081 Days on yellowkey   MLS ID: O6390542

    REDUCED by $2,000 (0.5%) on 04/20/2026

    For Sale O6390542 - 11686 WATER RUN ALY, WINDERMERE, FL 34786 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1584
       Built: 2017
    Monthly Fee: $332
       Tax: $6,025 (2025)
    Community: Ashlin Park Ph 2
    Spa: No

    Townhouse


    Estimated Monthly Payment: $3,080 (change assumption)
    Mortgage ($2,246) + Fees ($332) + Taxes in 2025 ($502)


    Taxes:$6,025

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13733 BRESSLER ALY, WINDERMERE, FL 34786

    $455,000116 Days on yellowkey   MLS ID: O6379257

    1 Days Off yellowkey (back on 5/11/2026)

    REDUCED by $9,999 (2.2%) on 04/20/2026

    For Sale O6379257 - 13733 BRESSLER ALY, WINDERMERE, FL 34786 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2002
       Built: 2019
    Monthly Fee: $185
       Tax: $7,023 (2024)
    Community: Vineyards/Horizons West Ph 4
    Townhouse


    Estimated Monthly Payment: $3,263 (change assumption)
    Mortgage ($2,493) + Fees ($185) + Taxes in 2024 ($585)


    Taxes:$7,023

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 9575 WESTOVER ROBERTS RD, WINDERMERE, FL 34786

    $4,850,000203 Days on yellowkey   MLS ID: O6357873

    REDUCED by $75,000 (1.5%) on 05/11/2026

    For Sale O6357873 - 9575 WESTOVER ROBERTS RD, WINDERMERE, FL 34786 95 photos

    Bed: 7   Bath: 8.0   Gar: 6
    Liv Area Sq Ft: 8931
       Built: 2008   Tax: $30,908 (2024)
    Community: Gotha Town
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $29,150 (change assumption)
    Mortgage ($26,575) + Taxes in 2024 ($2,576)


    Taxes:$30,908

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha 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.