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Winter Garden Single Family Homes For Sale - 515 homes

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

Location: Winter Garden

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  • 15070 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $729,90015 Days on yellowkey   MLS ID: S5146881

    REDUCED by $15,100 (2.0%) on 04/03/2026

    For Sale S5146881 - 15070 SUMMER HARVEST ST, WINTER GARDEN, FL 34787 38 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2025
    Monthly Fee: $233
       Tax: $9,545 (2024)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $5,028 (change assumption)
    Mortgage ($3,999) + Fees ($233) + Taxes in 2024 ($795)


    Taxes:$9,545

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 2031 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $489,00021 Days on yellowkey   MLS ID: O6394075

    1 Days Off yellowkey (back on 4/3/2026)

    For Sale O6394075 - 2031 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 17 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2000
    Monthly Fee: $90
       Tax: $4,516 (2025)
    Community: Wintermere Pointe
    Single Family


    Estimated Monthly Payment: $3,146 (change assumption)
    Mortgage ($2,679) + Fees ($90) + Taxes in 2025 ($376)


    Taxes:$4,516

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787

    $1,170,000147 Days on yellowkey   MLS ID: O6361968

    5 Days Off yellowkey (back on 4/2/2026)

    For Sale O6361968 - 10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787 97 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4305
       Built: 2020
    Monthly Fee: $159
       Tax: $13,997 (2024)
    Community: Watermark Ph 4
    Single Family


    Estimated Monthly Payment: $7,736 (change assumption)
    Mortgage ($6,411) + Fees ($159) + Taxes in 2024 ($1,166)


    Taxes:$13,997

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 869 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $535,000157 Days on yellowkey   MLS ID: O6358341

    For Sale O6358341 - 869 BENDING OAK TRL, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1975
       Built: 2012
    Monthly Fee: $109
       Tax: $5,262 (2024)
    Community: Oaks/Brandy Lake 01 Rep A & B
    Single Family


    Estimated Monthly Payment: $3,479 (change assumption)
    Mortgage ($2,931) + Fees ($109) + Taxes in 2024 ($438)


    Taxes:$5,262

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $749,90019 Days on yellowkey   MLS ID: O6394192

    For Sale O6394192 - 11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $295
       Tax: $3,196 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,670 (change assumption)
    Mortgage ($4,109) + Fees ($295) + Taxes in 2025 ($266)


    Taxes:$3,196

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787

    $874,99014 Days on yellowkey   MLS ID: O6395693

    For Sale O6395693 - 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2650
       Built: 2026
    Monthly Fee: $240
       Tax: $1,955 (2025)
    Community: Winter Grove
    Single Family


    Estimated Monthly Payment: $5,197 (change assumption)
    Mortgage ($4,794) + Fees ($240) + Taxes in 2025 ($163)


    Taxes:$1,955

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • WINTER GARDEN, FL 34787

    $688,78915 Days on yellowkey   MLS ID: G5110452

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

    For Sale G5110452 - WINTER GARDEN, FL 34787 2 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3117
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,924 (change assumption)
    Mortgage ($3,774) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17061 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $565,99015 Days on yellowkey   MLS ID: G5110436

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

    For Sale G5110436 - 17061 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,223 (change assumption)
    Mortgage ($3,101) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8197 LAKEVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $434,900115 Days on yellowkey   MLS ID: TB8458488

    0 Days Off yellowkey (back on 4/2/2026)

    For Sale TB8458488 - 8197 LAKEVIEW CROSSING DR, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1685
       Built: 2016
    Monthly Fee: $265
       Tax: $6,511 (2024)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,191 (change assumption)
    Mortgage ($2,383) + Fees ($265) + Taxes in 2024 ($543)


    Taxes:$6,511

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 1836 WINGED ELM PL, WINTER GARDEN, FL 34787

    $462,00032 Days on yellowkey   MLS ID: O6390771

    REDUCED by $13,000 (2.7%) on 04/02/2026

    For Sale O6390771 - 1836 WINGED ELM PL, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1712
       Built: 2005
    Monthly Fee: $55
       Tax: $6,075 (2025)
    Community: Winter Garden Trls 01-3
    Single Family


    Estimated Monthly Payment: $3,093 (change assumption)
    Mortgage ($2,531) + Fees ($55) + Taxes in 2025 ($506)


    Taxes:$6,075

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4937 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787

    $869,00074 Days on yellowkey   MLS ID: S5142834

    1 Days Off yellowkey (back on 4/2/2026)

    For Sale S5142834 - 4937 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787 80 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3289
       Built: 2015
    Monthly Fee: $187
       Tax: $10,004 (2024)
    Community: Orchard Hills Ph 2
    Single Family


    Estimated Monthly Payment: $5,782 (change assumption)
    Mortgage ($4,762) + Fees ($187) + Taxes in 2024 ($834)


    Taxes:$10,004

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 16077 BARKLY RIDGE CT, WINTER GARDEN, FL 34787

    $2,200,00027 Days on yellowkey   MLS ID: O6391901

    For Sale O6391901 - 16077 BARKLY RIDGE CT, WINTER GARDEN, FL 34787 47 photos

    Bed: 6   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 5524
       Built: 2024
    Monthly Fee: $225
       Tax: $8,585 (2025)
    Community: Avalon Rdg
    Single Family


    Estimated Monthly Payment: $12,995 (change assumption)
    Mortgage ($12,054) + Fees ($225) + Taxes in 2025 ($715)


    Taxes:$8,585

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 4842 LIME RICKEY ALY, WINTER GARDEN, FL 34787

    $539,90063 Days on yellowkey   MLS ID: O6381954

    REDUCED by $5,000 (0.9%) on 04/02/2026

    For Sale O6381954 - 4842 LIME RICKEY ALY, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 2023
    Monthly Fee: $148
       Tax: $8,002 (2024)
    Community: Silverleaf Reserve/Haml Ph 2A
    Single Family


    Estimated Monthly Payment: $3,773 (change assumption)
    Mortgage ($2,958) + Fees ($148) + Taxes in 2024 ($667)


    Taxes:$8,002

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $690,90078 Days on yellowkey   MLS ID: S5142710

    2 Days Off yellowkey (back on 4/2/2026)

    For Sale S5142710 - 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2908
       Built: 2024
    Monthly Fee: $202
       Tax: $9,669 (2025)
    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,793 (change assumption)
    Mortgage ($3,786) + Fees ($202) + Taxes in 2025 ($806)


    Taxes:$9,669

    Elementary School: Whispering Oak Elem

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 5778 LAUREL CHERRY AVE, WINTER GARDEN, FL 34787

    $540,00015 Days on yellowkey   MLS ID: O6395452

    For Sale O6395452 - 5778 LAUREL CHERRY AVE, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2524
       Built: 2016
    Monthly Fee: $195
       Tax: $9,031 (2025)
    Community: Signature Lakes
    Single Family


    Estimated Monthly Payment: $3,906 (change assumption)
    Mortgage ($2,959) + Fees ($195) + Taxes in 2025 ($753)


    Taxes:$9,031

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1720 PORTCASTLE CIR, WINTER GARDEN, FL 34787

    $389,90078 Days on yellowkey   MLS ID: O6377195

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

    For Sale O6377195 - 1720 PORTCASTLE CIR, WINTER GARDEN, FL 34787 27 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1606
       Built: 2004
    Monthly Fee: $46
       Tax: $5,520 (2024)
    Community: Stone Creek Unit 4
    Single Family


    Estimated Monthly Payment: $2,642 (change assumption)
    Mortgage ($2,136) + Fees ($46) + Taxes in 2024 ($460)


    Taxes:$5,520

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 327 S LAKEVIEW AVE, WINTER GARDEN, FL 34787

    $849,00017 Days on yellowkey   MLS ID: O6394438

    0 Days Off yellowkey (back on 4/2/2026)

    For Sale O6394438 - 327 S LAKEVIEW AVE, WINTER GARDEN, FL 34787 72 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2225
       Built: 2014   Tax: $2,758 (2025)
    Community: G T Smith Sub 3
    Single Family


    Estimated Monthly Payment: $4,882 (change assumption)
    Mortgage ($4,652) + Taxes in 2025 ($230)


    Taxes:$2,758

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $724,90039 Days on yellowkey   MLS ID: O6388830

    For Sale O6388830 - 18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2924
       Built: 2024
    Monthly Fee: $280
       Tax: $10,366 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,116 (change assumption)
    Mortgage ($3,972) + Fees ($280) + Taxes in 2024 ($864)


    Taxes:$10,366

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: None


  • 16826 BROADWATER AVE, WINTER GARDEN, FL 34787

    $1,540,00043 Days on yellowkey   MLS ID: O6387379

    REDUCED by $50,000 (3.1%) on 04/02/2026

    For Sale O6387379 - 16826 BROADWATER AVE, WINTER GARDEN, FL 34787 58 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4451
       Built: 2019
    Monthly Fee: $218
       Tax: $9,892 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Single Family


    Estimated Monthly Payment: $9,480 (change assumption)
    Mortgage ($8,438) + Fees ($218) + Taxes in 2025 ($824)


    Taxes:$9,892

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • WINTER GARDEN, FL 34787

    $510,88015 Days on yellowkey   MLS ID: G5110456

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

    For Sale G5110456 - WINTER GARDEN, FL 34787 2 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $2,949 (change assumption)
    Mortgage ($2,799) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle




Why Bother Searching Elsewhere for Winter Garden Single Family Homes for Sale?

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