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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Price: $500,000 to $599,000

Winter Garden - 164 properties found

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  • 17058 QUICKSILVER AVE, WINTER GARDEN, FL 34787

    $539,000198 Days on yellowkey   MLS ID: O6365686

    0 Days Off yellowkey (back on 6/1/2026)

    For Sale O6365686 - 17058 QUICKSILVER AVE, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2492
       Built: 2021
    Monthly Fee: $215
       Tax: $7,682 (2024)
    Community: Waterside/Johns Lake Ph 2C
    Single Family


    Estimated Monthly Payment: $3,809 (change assumption)
    Mortgage ($2,953) + Fees ($215) + Taxes in 2024 ($640)


    Taxes:$7,682

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 12915 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $594,000135 Days on yellowkey   MLS ID: O6381156

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

    For Sale O6381156 - 12915 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,526 (change assumption)
    Mortgage ($3,255) + Fees ($77) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $548,000140 Days on yellowkey   MLS ID: O6379918

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

    For Sale O6379918 - 12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2062
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,273 (change assumption)
    Mortgage ($3,003) + Fees ($77) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17124 BEACHGRASS ALY, WINTER GARDEN, FL 34787

    $559,99037 Days on yellowkey   MLS ID: O6408024

    0 Days Off yellowkey (back on 6/1/2026)

    For Sale O6408024 - 17124 BEACHGRASS ALY, WINTER GARDEN, FL 34787 4 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1983
       Built: 2026
    Monthly Fee: $112
       Tax: $6,874 (2025)
    Community: Lake Star At Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,753 (change assumption)
    Mortgage ($3,068) + Fees ($112) + Taxes in 2025 ($573)


    Taxes:$6,874

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 516 S HIGHLAND AVE, WINTER GARDEN, FL 34787

    $500,00030 Days on yellowkey   MLS ID: O6409675

    1 Days Off yellowkey (back on 5/29/2026)

    For Sale O6409675 - 516 S HIGHLAND AVE, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1716
       Built: 1955   Tax: $709 (2025)
    Community: Rep Pt Pleasant Park Sub
    Single Family


    Estimated Monthly Payment: $2,799 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($59)


    Taxes:$709

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 10301 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787

    $530,00027 Days on yellowkey   MLS ID: O6411527

    For Sale O6411527 - 10301 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2078
       Built: 2020
    Monthly Fee: $154
       Tax: $7,738 (2024)
    Community: Watermark Ph 4
    Single Family


    Estimated Monthly Payment: $3,703 (change assumption)
    Mortgage ($2,904) + Fees ($154) + Taxes in 2024 ($645)


    Taxes:$7,738

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16632 POINT ROCK DR, WINTER GARDEN, FL 34787

    $550,000177 Days on yellowkey   MLS ID: OM715702

    0 Days Off yellowkey (back on 5/29/2026)

    SHORT SALE OM715702 - 16632 POINT ROCK DR, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2292
       Built: 2023
    Monthly Fee: $281
       Tax: $8,546 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,007 (change assumption)
    Mortgage ($3,014) + Fees ($281) + Taxes in 2024 ($712)


    Taxes:$8,546

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787

    $594,000136 Days on yellowkey   MLS ID: S5143009

    For Sale S5143009 - 15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787 23 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2695
       Built: 2016
    Monthly Fee: $241
       Tax: $8,470 (2024)
    Community: Summerlake Pd Ph 2C 2D 2E
    Single Family


    Estimated Monthly Payment: $4,202 (change assumption)
    Mortgage ($3,255) + Fees ($241) + Taxes in 2024 ($706)


    Taxes:$8,470

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787

    $579,90070 Days on yellowkey   MLS ID: O6396640

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

    For Sale O6396640 - 15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2626
       Built: 2013
    Monthly Fee: $128
       Tax: $6,746 (2025)
    Community: Johns Lake Pointe A & S
    Single Family


    Estimated Monthly Payment: $3,868 (change assumption)
    Mortgage ($3,177) + Fees ($128) + Taxes in 2025 ($562)


    Taxes:$6,746

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16197 WIND VIEW LN, WINTER GARDEN, FL 34787

    $517,00076 Days on yellowkey   MLS ID: O6397229

    REDUCED by $3,000 (0.6%) on 05/24/2026

    For Sale O6397229 - 16197 WIND VIEW LN, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2016
    Monthly Fee: $332
       Tax: $7,677 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,805 (change assumption)
    Mortgage ($2,833) + Fees ($332) + Taxes in 2025 ($640)


    Taxes:$7,677

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14571 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $519,900188 Days on yellowkey   MLS ID: O6368387

    0 Days Off yellowkey (back on 5/23/2026)

    For Sale O6368387 - 14571 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2063
       Built: 2012
    Monthly Fee: $251
       Tax: $7,507 (2024)
    Community: Summerlake Pd Ph 01A
    Single Family


    Estimated Monthly Payment: $3,725 (change assumption)
    Mortgage ($2,849) + Fees ($251) + Taxes in 2024 ($626)


    Taxes:$7,507

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 2200 ROMANUM DR, WINTER GARDEN, FL 34787

    $560,00040 Days on yellowkey   MLS ID: O6408190

    For Sale O6408190 - 2200 ROMANUM DR, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2561
       Built: 2015
    Monthly Fee: $211
       Tax: $8,843 (2025)
    Community: Alexander Rdg
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,016 (change assumption)
    Mortgage ($3,068) + Fees ($211) + Taxes in 2025 ($737)


    Taxes:$8,843

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17098 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $560,000226 Days on yellowkey   MLS ID: O6357599

    REDUCED by $20,000 (3.4%) on 05/21/2026

    For Sale O6357599 - 17098 WATER SPRING BLVD, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2484
       Built: 2023
    Monthly Fee: $271
       Tax: $9,199 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,106 (change assumption)
    Mortgage ($3,068) + Fees ($271) + Taxes in 2024 ($767)


    Taxes:$9,199

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $529,999149 Days on yellowkey   MLS ID: NS1087076

    1 Days Off yellowkey (back on 5/21/2026)

    REDUCED by $38,001 (6.7%) on 05/02/2026

    For Sale NS1087076 - 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787 23 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2024
    Monthly Fee: $291
       Tax: $2,273 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,384 (change assumption)
    Mortgage ($2,904) + Fees ($291) + Taxes in 2024 ($189)


    Taxes:$2,273

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 8906 DODDINGTON WAY, WINTER GARDEN, FL 34787

    $550,000146 Days on yellowkey   MLS ID: O6377538

    2 Days Off yellowkey (back on 5/6/2026)

    For Sale O6377538 - 8906 DODDINGTON WAY, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2352
       Built: 2016
    Monthly Fee: $115
       Tax: $9,036 (2025)
    Community: Latham Park North
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,882 (change assumption)
    Mortgage ($3,014) + Fees ($115) + Taxes in 2025 ($753)


    Taxes:$9,036

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14736 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $550,00099 Days on yellowkey   MLS ID: O6391435

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

    For Sale O6391435 - 14736 FIELD DAISY DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2149
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $3,243 (change assumption)
    Mortgage ($3,014) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16809 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $559,990167 Days on yellowkey   MLS ID: O6372242

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

    REDUCED by $10,000 (1.8%) on 05/14/2026

    For Sale O6372242 - 16809 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2025
    Monthly Fee: $248
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,482 (change assumption)
    Mortgage ($3,068) + Fees ($248) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6102 WHISPERING GLEN, WINTER GARDEN, FL 34787

    $576,89042 Days on yellowkey   MLS ID: O6407803

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

    For Sale O6407803 - 6102 WHISPERING GLEN, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1913
       Built: 2024
    Monthly Fee: $152
       Tax: $1,372 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,427 (change assumption)
    Mortgage ($3,161) + Fees ($152) + Taxes in 2024 ($114)


    Taxes:$1,372

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 2230 ROMANUM DR, WINTER GARDEN, FL 34787

    $565,000104 Days on yellowkey   MLS ID: O6389947

    1 Days Off yellowkey (back on 5/17/2026)

    For Sale O6389947 - 2230 ROMANUM DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2562
       Built: 2014
    Monthly Fee: $207
       Tax: $8,425 (2025)
    Community: Alexander Rdg
    Single Family


    Estimated Monthly Payment: $4,005 (change assumption)
    Mortgage ($3,096) + Fees ($207) + Taxes in 2025 ($702)


    Taxes:$8,425

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15518 FOUNTAIN COVE CT, WINTER GARDEN, FL 34787

    $574,99041 Days on yellowkey   MLS ID: O6407942

    For Sale O6407942 - 15518 FOUNTAIN COVE CT, WINTER GARDEN, FL 34787 74 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2040
       Built: 2018
    Monthly Fee: $342
       Tax: $8,434 (2025)
    Community: Waterleigh Ph 1A
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,195 (change assumption)
    Mortgage ($3,151) + Fees ($342) + Taxes in 2025 ($703)


    Taxes:$8,434

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle






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.