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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Beds: 5 to 5

Winter Garden - 138 properties found

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  • 1209 CASTLEPORT RD, WINTER GARDEN, FL 34787

    $664,90051 Days on yellowkey   MLS ID: O6390760

    REDUCED by $10,090 (1.5%) on 04/14/2026

    For Sale O6390760 - 1209 CASTLEPORT RD, WINTER GARDEN, FL 34787 36 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2001
    Monthly Fee: $243
       Tax: $4,030 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,222 (change assumption)
    Mortgage ($3,643) + Fees ($243) + Taxes in 2025 ($336)


    Taxes:$4,030

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15312 GILLIGAN CT, WINTER GARDEN, FL 34787

    $1,150,000102 Days on yellowkey   MLS ID: O6372954

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale O6372954 - 15312 GILLIGAN CT, WINTER GARDEN, FL 34787 69 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3652
       Built: 2020
    Monthly Fee: $102
       Tax: $9,787 (2024)
    Community: Winding Bay Ii Llc
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,219 (change assumption)
    Mortgage ($6,301) + Fees ($102) + Taxes in 2024 ($816)


    Taxes:$9,787

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17031 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $646,09022 Days on yellowkey   MLS ID: G5110934

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale G5110934 - 17031 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2680
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,680 (change assumption)
    Mortgage ($3,540) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9014 MORGANA CT, WINTER GARDEN, FL 34787

    $2,190,000117 Days on yellowkey   MLS ID: O6371050

    REDUCED by $35,000 (1.6%) on 04/12/2026

    For Sale O6371050 - 9014 MORGANA CT, WINTER GARDEN, FL 34787 55 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4436
       Built: 2022
    Monthly Fee: $424
       Tax: $24,481 (2025)
    Community: Avalon Cove
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,464 (change assumption)
    Mortgage ($12,000) + Fees ($424) + Taxes in 2025 ($2,040)


    Taxes:$24,481

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5526 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787

    $649,000147 Days on yellowkey   MLS ID: O6365476

    REDUCED by $31,000 (4.6%) on 04/11/2026

    For Sale O6365476 - 5526 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787 59 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2240
       Built: 2013
    Monthly Fee: $184
       Tax: $8,004 (2025)
    Community: Signature Lakes
    Single Family


    Estimated Monthly Payment: $4,407 (change assumption)
    Mortgage ($3,556) + Fees ($184) + Taxes in 2025 ($667)


    Taxes:$8,004

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 915 WESTCLIFFE DR, WINTER GARDEN, FL 34787

    $620,00095 Days on yellowkey   MLS ID: G5107429

    REDUCED by $10,000 (1.6%) on 04/09/2026

    For Sale G5107429 - 915 WESTCLIFFE DR, WINTER GARDEN, FL 34787 47 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2868
       Built: 2006
    Monthly Fee: $50
       Tax: $4,426 (2024)
    Community: Fullers Lndg B
    Single Family


    Estimated Monthly Payment: $3,816 (change assumption)
    Mortgage ($3,397) + Fees ($50) + Taxes in 2024 ($369)


    Taxes:$4,426

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16167 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $699,50060 Days on yellowkey   MLS ID: O6387577

    2 Days Off yellowkey (back on 4/9/2026)

    For Sale O6387577 - 16167 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787 73 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2017
    Monthly Fee: $341
       Tax: $5,669 (2024)
    Community: Waterleigh Ph 1C
    Single Family


    Estimated Monthly Payment: $4,646 (change assumption)
    Mortgage ($3,833) + Fees ($341) + Taxes in 2024 ($472)


    Taxes:$5,669

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 743 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,499,99941 Days on yellowkey   MLS ID: O6392705

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale O6392705 - 743 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 71 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4283
       Built: 2018
    Monthly Fee: $298
       Tax: $10,715 (2025)
    Community: Canopy Oaks Ph I
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,410 (change assumption)
    Mortgage ($8,219) + Fees ($298) + Taxes in 2025 ($893)


    Taxes:$10,715

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15060 BRODIE LN, WINTER GARDEN, FL 34787

    $925,000409 Days on yellowkey   MLS ID: O6292102

    3 Days Off yellowkey (back on 2/23/2026)

    For Sale O6292102 - 15060 BRODIE LN, WINTER GARDEN, FL 34787 79 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3256
       Built: 2024
    Monthly Fee: $110
       Tax: $2,642 (2024)
    Community: Westhaven/Ovation
    Single Family


    Estimated Monthly Payment: $5,399 (change assumption)
    Mortgage ($5,068) + Fees ($110) + Taxes in 2024 ($220)


    Taxes:$2,642

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $819,00080 Days on yellowkey   MLS ID: O6380281

    REDUCED by $30,000 (3.5%) on 04/06/2026

    For Sale O6380281 - 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 58 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3747
       Built: 2000
    Monthly Fee: $90
       Tax: $10,152 (2025)
    Community: Wintermere Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,424 (change assumption)
    Mortgage ($4,488) + Fees ($90) + Taxes in 2025 ($846)


    Taxes:$10,152

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 730 RIVER GRASS LN, WINTER GARDEN, FL 34787

    $649,90099 Days on yellowkey   MLS ID: G5107248

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

    For Sale G5107248 - 730 RIVER GRASS LN, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2647
       Built: 2014
    Monthly Fee: $72
       Tax: $3,572 (2024)
    Community: Covington Chase Ph 2C
    Single Family


    Estimated Monthly Payment: $3,931 (change assumption)
    Mortgage ($3,561) + Fees ($72) + Taxes in 2024 ($298)


    Taxes:$3,572

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15518 HONEY MANDARIN WAY, WINTER GARDEN, FL 34787

    $869,90031 Days on yellowkey   MLS ID: O6396204

    For Sale O6396204 - 15518 HONEY MANDARIN WAY, WINTER GARDEN, FL 34787 70 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3640
       Built: 2018
    Monthly Fee: $113
       Tax: $11,489 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $5,837 (change assumption)
    Mortgage ($4,766) + Fees ($113) + Taxes in 2025 ($957)


    Taxes:$11,489

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1073 VINSETTA CIR, WINTER GARDEN, FL 34787

    $725,000288 Days on yellowkey   MLS ID: O6328215

    INCREASED by $10,000 (1.4%) on 04/02/2026

    For Sale O6328215 - 1073 VINSETTA CIR, WINTER GARDEN, FL 34787 72 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3568
       Built: 2014
    Monthly Fee: $95
       Tax: $5,710 (2024)
    Community: Avalon Reserve Village 1
    Single Family


    Estimated Monthly Payment: $4,543 (change assumption)
    Mortgage ($3,973) + Fees ($95) + Taxes in 2024 ($476)


    Taxes:$5,710

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787

    $874,99032 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

    $688,78933 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


  • 15625 SYLVESTER PALM DR, WINTER GARDEN, FL 34787

    $1,115,00088 Days on yellowkey   MLS ID: O6379346

    For Sale O6379346 - 15625 SYLVESTER PALM DR, WINTER GARDEN, FL 34787 72 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 3886
       Built: 2018
    Monthly Fee: $360
       Tax: $9,571 (2024)
    Community: Lakeshore Preserve Ph 1
    Single Family


    Estimated Monthly Payment: $7,267 (change assumption)
    Mortgage ($6,109) + Fees ($360) + Taxes in 2024 ($798)


    Taxes:$9,571

    Elementary School: Panther Lake Elementary

    High School: None

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 11229 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $806,801105 Days on yellowkey   MLS ID: O6375011

    2 Days Off yellowkey (back on 3/31/2026)

    For Sale O6375011 - 11229 HOLLOW BAY DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,785 (change assumption)
    Mortgage ($4,421) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14254 SUNRIDGE BLVD, WINTER GARDEN, FL 34787

    $1,150,00037 Days on yellowkey   MLS ID: TB8489171

    For Sale TB8489171 - 14254 SUNRIDGE BLVD, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 3.5
    Liv Area Sq Ft: 4004
       Built: 2017
    Monthly Fee: $75
       Tax: $11,716 (2025)
    Community: Cypress Reserve Ph 1
    Single Family


    Estimated Monthly Payment: $7,353 (change assumption)
    Mortgage ($6,301) + Fees ($75) + Taxes in 2025 ($976)


    Taxes:$11,716

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 2450 DAHLGREN WAY, WINTER GARDEN, FL 34787

    $1,950,00063 Days on yellowkey   MLS ID: TB8481106

    For Sale TB8481106 - 2450 DAHLGREN WAY, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 5.0
    Liv Area Sq Ft: 4365
       Built: 2007
    Monthly Fee: $225
       Tax: $8,970 (2024)
    Community: Bronsons Lndgs F & M
    Single Family


    Estimated Monthly Payment: $11,657 (change assumption)
    Mortgage ($10,685) + Fees ($225) + Taxes in 2024 ($748)


    Taxes:$8,970

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 1226 PORTMOOR WAY, WINTER GARDEN, FL 34787

    $650,00079 Days on yellowkey   MLS ID: O6381941

    For Sale O6381941 - 1226 PORTMOOR WAY, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2856
       Built: 2003
    Monthly Fee: $243
       Tax: $7,279 (2024)
    Community: Stoneybrook West 44/134
    Single Family


    Estimated Monthly Payment: $4,411 (change assumption)
    Mortgage ($3,562) + Fees ($243) + Taxes in 2024 ($607)


    Taxes:$7,279

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge 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.