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Winter Garden Homes For Sale & Real Estate - 843 homes

Winter Garden homes for sale are located in Orange County, Florida. Find homes in Winter Garden for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden houses.

Location: Winter Garden

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  • 2217 RICKOVER PL, WINTER GARDEN, FL 34787

    $1,059,00066 Days on yellowkey   MLS ID: O6388647

    1 Days Off yellowkey (back on 4/27/2026)

    REDUCED by $16,000 (1.5%) on 04/20/2026

    For Sale O6388647 - 2217 RICKOVER PL, WINTER GARDEN, FL 34787 49 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4324
       Built: 2008
    Monthly Fee: $260
       Tax: $8,547 (2025)
    Community: Bronsons Lndgs F & M
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,775 (change assumption)
    Mortgage ($5,803) + Fees ($260) + Taxes in 2025 ($712)


    Taxes:$8,547

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 4136 WILLOW BAY DR, WINTER GARDEN, FL 34787

    $655,00035 Days on yellowkey   MLS ID: R4911030

    1 Days Off yellowkey (back on 4/27/2026)

    For Sale R4911030 - 4136 WILLOW BAY DR, WINTER GARDEN, FL 34787 14 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2472
       Built: 2001
    Monthly Fee: $315
       Tax: $8,781 (2025)
    Community: Woodbridge On Green
    Single Family


    Estimated Monthly Payment: $4,636 (change assumption)
    Mortgage ($3,589) + Fees ($315) + Taxes in 2025 ($732)


    Taxes:$8,781

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 344 ERON WAY #12, WINTER GARDEN, FL 34787

    $159,000218 Days on yellowkey   MLS ID: O6349452

    0 Days Off yellowkey (back on 4/27/2026)

    For Sale O6349452 - 344 ERON WAY #12, WINTER GARDEN, FL 34787 16 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1987
    Monthly Fee: $425
       Tax: $2,408 (2024)
    Community: Townhomes Winter Garden
    Condo


    Estimated Monthly Payment: $1,497 (change assumption)
    Mortgage ($871) + Fees ($425) + Taxes in 2024 ($201)


    Taxes:$2,408

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 150 WINDTREE LN #150, WINTER GARDEN, FL 34787

    $195,000160 Days on yellowkey   MLS ID: O6365343

    REDUCED by $4,900 (2.5%) on 04/20/2026

    For Sale O6365343 - 150 WINDTREE LN #150, WINTER GARDEN, FL 34787 31 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1984
    Monthly Fee: $300
       Tax: $2,565 (2025)
    Community: Windree Gardens Ph 5
    Condo


    Estimated Monthly Payment: $1,582 (change assumption)
    Mortgage ($1,068) + Fees ($300) + Taxes in 2025 ($214)


    Taxes:$2,565

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15684 ORANGE HARVEST LOOP, WINTER GARDEN, FL 34787

    $469,90019 Days on yellowkey   MLS ID: W7885221

    INCREASED by $100,000 (27.0%) on 04/26/2026

    For Sale W7885221 - 15684 ORANGE HARVEST LOOP, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2012
       Built: 2016
    Monthly Fee: $366
       Tax: $5,348 (2025)
    Community: Hickory Hammock
    Spa: No

    Townhouse


    Estimated Monthly Payment: $3,386 (change assumption)
    Mortgage ($2,575) + Fees ($366) + Taxes in 2025 ($446)


    Taxes:$5,348

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14501 GROVE RESORT AVE, WINTER GARDEN, FL 34787

    $235,00019 Days on yellowkey   MLS ID: O6401424

    For Sale O6401424 - 14501 GROVE RESORT AVE, WINTER GARDEN, FL 34787 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2025
    Monthly Fee: $905
       Tax: $7,772 (2025)
    Community: Grove Resort And Spa Hotel Condo 1
    Condo


    Estimated Monthly Payment: $2,840 (change assumption)
    Mortgage ($1,288) + Fees ($905) + Taxes in 2025 ($648)


    Taxes:$7,772

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16548 RAVEN ROCK PL, WINTER GARDEN, FL 34787

    $1,459,90081 Days on yellowkey   MLS ID: S5144064

    For Sale S5144064 - 16548 RAVEN ROCK PL, WINTER GARDEN, FL 34787 36 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4263
       Built: 2017
    Monthly Fee: $178
       Tax: $16,938 (2024)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $9,589 (change assumption)
    Mortgage ($7,999) + Fees ($178) + Taxes in 2024 ($1,411)


    Taxes:$16,938

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13212 SOCIAL LN, WINTER GARDEN, FL 34787

    $595,00029 Days on yellowkey   MLS ID: O6398708

    For Sale O6398708 - 13212 SOCIAL LN, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2526
       Built: 2005
    Monthly Fee: $100
       Tax: $4,474 (2025)
    Community: Regency Oaks F
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,733 (change assumption)
    Mortgage ($3,260) + Fees ($100) + Taxes in 2025 ($373)


    Taxes:$4,474

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15563 ORCHID ROSE COURT, WINTER GARDEN, FL 34787

    $799,00029 Days on yellowkey   MLS ID: O6399638

    1 Days Off yellowkey (back on 4/22/2026)

    For Sale O6399638 - 15563 ORCHID ROSE COURT, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2808
       Built: 2026
    Monthly Fee: $544
       Tax: $545 (2025)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,967 (change assumption)
    Mortgage ($4,378) + Fees ($544) + Taxes in 2025 ($45)


    Taxes:$545

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787

    $929,00047 Days on yellowkey   MLS ID: O6394506

    REDUCED by $20,900 (2.2%) on 04/20/2026

    For Sale O6394506 - 1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3841
       Built: 2017
    Monthly Fee: $184
       Tax: $12,543 (2025)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $6,320 (change assumption)
    Mortgage ($5,090) + Fees ($184) + Taxes in 2025 ($1,045)


    Taxes:$12,543

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 2230 ROMANUM DR, WINTER GARDEN, FL 34787

    $565,00064 Days on yellowkey   MLS ID: O6389947

    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


  • 14626 BLACK QUILL DR, WINTER GARDEN, FL 34787

    $799,90029 Days on yellowkey   MLS ID: O6399975

    0 Days Off yellowkey (back on 4/26/2026)

    For Sale O6399975 - 14626 BLACK QUILL DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2907
       Built: 2016
    Monthly Fee: $215
       Tax: $6,816 (2025)
    Community: Overlook At Hamlin
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,166 (change assumption)
    Mortgage ($4,383) + Fees ($215) + Taxes in 2025 ($568)


    Taxes:$6,816

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5966 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $695,000112 Days on yellowkey   MLS ID: O6376219

    For Sale O6376219 - 5966 CYPRESS HILL RD, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2839
       Built: 2017
    Monthly Fee: $195
       Tax: $9,648 (2025)
    Community: Signature Lakes Ph 3B-4, 3B-5 & 3B-7 83/27 Lot 184
    Single Family


    Estimated Monthly Payment: $4,807 (change assumption)
    Mortgage ($3,808) + Fees ($195) + Taxes in 2025 ($804)


    Taxes:$9,648

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12965 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $882,93253 Days on yellowkey   MLS ID: O6392975

    1 Days Off yellowkey (back on 4/26/2026)

    For Sale O6392975 - 12965 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3101
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,978 (change assumption)
    Mortgage ($4,838) + Fees ($140) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 15391 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $949,000115 Days on yellowkey   MLS ID: O6375228

    1 Days Off yellowkey (back on 4/26/2026)

    For Sale O6375228 - 15391 LEBEAU LOOP, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3042
       Built: 2022
    Monthly Fee: $101
       Tax: $10,724 (2025)
    Community: Winding Bay Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,195 (change assumption)
    Mortgage ($5,200) + Fees ($101) + Taxes in 2025 ($894)


    Taxes:$10,724

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 6177 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $729,38520 Days on yellowkey   MLS ID: G5111566

    0 Days Off yellowkey (back on 4/25/2026)

    For Sale G5111566 - 6177 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2688
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,147 (change assumption)
    Mortgage ($3,997) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9201 GRAN TEATRO DR, WINTER GARDEN, FL 34787

    $525,00020 Days on yellowkey   MLS ID: O6401827

    For Sale O6401827 - 9201 GRAN TEATRO DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1715
       Built: 2024
    Monthly Fee: $292
       Tax: $6,402 (2025)
    Community: Tribute/Ovation
    Townhouse


    Estimated Monthly Payment: $3,702 (change assumption)
    Mortgage ($2,877) + Fees ($292) + Taxes in 2025 ($534)


    Taxes:$6,402

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17588 LAKE STAR RD, WINTER GARDEN, FL 34787

    $1,185,00064 Days on yellowkey   MLS ID: O6387269

    REDUCED by $10,000 (0.8%) on 04/25/2026

    For Sale O6387269 - 17588 LAKE STAR RD, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4026
       Built: 2024
    Monthly Fee: $84
       Tax: $3,806 (2024)
    Community: Northlake At Ovation
    Single Family


    Estimated Monthly Payment: $6,894 (change assumption)
    Mortgage ($6,493) + Fees ($84) + Taxes in 2024 ($317)


    Taxes:$3,806

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 4918 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787

    $680,000335 Days on yellowkey   MLS ID: S5129072

    For Sale S5129072 - 4918 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787 38 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2868
       Built: 2015
    Monthly Fee: $172
       Tax: $10,554 (2024)
    Community: Orchard Hills Ph 2
    Single Family


    Estimated Monthly Payment: $4,777 (change assumption)
    Mortgage ($3,726) + Fees ($172) + Taxes in 2024 ($880)


    Taxes:$10,554

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 14501 GROVE RESORT AVE #2535, WINTER GARDEN, FL 34787

    $179,900102 Days on yellowkey   MLS ID: O6378144

    REDUCED by $5,000 (2.7%) on 04/25/2026

    FORECLOSURE O6378144 - 14501 GROVE RESORT AVE #2535, WINTER GARDEN, FL 34787 70 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1434
       Built: 2018   Tax: $8,168 (2025)
    Community: Grove Resort And Spa
    Spa: Yes

    Condo


    Estimated Monthly Payment: $1,666 (change assumption)
    Mortgage ($986) + Taxes in 2025 ($681)


    Taxes:$8,168

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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Winter Garden 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 Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden 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 Winter Garden 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.