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


Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 2500 to 2999

Winter Garden - 156 properties found

Sort:
  • 13780 FRESH IVY ST, WINTER GARDEN, FL 34787

    $865,00049 Days on yellowkey   MLS ID: O6403387

    REDUCED by $30,000 (3.4%) on 06/06/2026

    For Sale O6403387 - 13780 FRESH IVY ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2862
       Built: 2025
    Monthly Fee: $642
       Tax: $2,578 (2025)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $5,596 (change assumption)
    Mortgage ($4,740) + Fees ($642) + Taxes in 2025 ($215)


    Taxes:$2,578

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $669,990147 Days on yellowkey   MLS ID: S5142710

    REDUCED by $22,000 (3.2%) on 06/19/2026

    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: $4,679 (change assumption)
    Mortgage ($3,671) + 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


  • 12390 CLEAR SAPPHIRE, WINTER GARDEN, FL 34787

    $764,99086 Days on yellowkey   MLS ID: O6394850

    1 Days Off yellowkey (back on 6/19/2026)

    REDUCED by $5,000 (0.6%) on 06/16/2026

    For Sale O6394850 - 12390 CLEAR SAPPHIRE, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2552
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,288 (change assumption)
    Mortgage ($4,192) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 1219 SADDLEBACK DR, WINTER GARDEN, FL 34787

    $1,050,00019 Days on yellowkey   MLS ID: O6412381

    0 Days Off yellowkey (back on 6/18/2026)

    For Sale O6412381 - 1219 SADDLEBACK DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2667
       Built: 2022
    Monthly Fee: $215
       Tax: $11,474 (2025)
    Community: Oakland Parkb-1
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,924 (change assumption)
    Mortgage ($5,753) + Fees ($215) + Taxes in 2025 ($956)


    Taxes:$11,474

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 12451 CLEAR SAPPHIRE DR, WINTER GARDEN, FL 34787

    $599,99028 Days on yellowkey   MLS ID: O6411261

    REDUCED by $24,000 (3.8%) on 06/18/2026

    For Sale O6411261 - 12451 CLEAR SAPPHIRE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2500
       Built: 2026
    Monthly Fee: $96
       Tax: $5,390 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $3,833 (change assumption)
    Mortgage ($3,288) + Fees ($96) + Taxes in 2026 ($449)


    Taxes:$5,390

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 214 S WOODLAND ST, WINTER GARDEN, FL 34787

    $800,00021 Days on yellowkey   MLS ID: O6413395

    For Sale O6413395 - 214 S WOODLAND ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2868
       Built: 1925   Tax: $2,450 (2025)
    Community: Fries Winter Garden
    Single Family


    Estimated Monthly Payment: $4,588 (change assumption)
    Mortgage ($4,383) + Taxes in 2025 ($204)


    Taxes:$2,450

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 745 MARSH REED DR, WINTER GARDEN, FL 34787

    $598,00021 Days on yellowkey   MLS ID: TB8514854

    REDUCED by $37,000 (5.8%) on 06/18/2026

    For Sale TB8514854 - 745 MARSH REED DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2596
       Built: 2015
    Monthly Fee: $132
       Tax: $8,274 (2025)
    Community: John Lake Pointe
    Single Family


    Estimated Monthly Payment: $4,098 (change assumption)
    Mortgage ($3,277) + Fees ($132) + Taxes in 2025 ($690)


    Taxes:$8,274

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 10174 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $999,00059 Days on yellowkey   MLS ID: O6402434

    REDUCED by $26,000 (2.5%) on 06/18/2026

    For Sale O6402434 - 10174 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2758
       Built: 2020
    Monthly Fee: $250
       Tax: $7,946 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Single Family


    Estimated Monthly Payment: $6,386 (change assumption)
    Mortgage ($5,474) + Fees ($250) + Taxes in 2025 ($662)


    Taxes:$7,946

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15174 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $689,0007 Days on yellowkey   MLS ID: O6415990

    For Sale O6415990 - 15174 FIELD DAISY DR, WINTER GARDEN, FL 34787 62 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2686
       Built: 2025
    Monthly Fee: $96
       Tax: $2,290 (2025)
    Community: Osprey Ranch Ph 1
    Single Family


    Estimated Monthly Payment: $4,062 (change assumption)
    Mortgage ($3,775) + Fees ($96) + Taxes in 2025 ($191)


    Taxes:$2,290

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13706 WERRINGTON DR, WINTER GARDEN, FL 34787

    $715,000230 Days on yellowkey   MLS ID: S5138020

    For Sale S5138020 - 13706 WERRINGTON DR, WINTER GARDEN, FL 34787 77 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2807
       Built: 2022
    Monthly Fee: $192
       Tax: $8,345 (2023)
    Community: Encore At Ovation-Ph 3
    Single Family


    Estimated Monthly Payment: $4,805 (change assumption)
    Mortgage ($3,918) + Fees ($192) + Taxes in 2023 ($695)


    Taxes:$8,345

    Elementary School: Water Spring Elementary

    High School: None

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 5966 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $695,000152 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


  • 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $650,000447 Days on yellowkey   MLS ID: O6280496

    REDUCED by $98,000 (13.1%) on 06/10/2026

    SHORT SALE O6280496 - 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2023
    Monthly Fee: $250
       Tax: $9,777 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,626 (change assumption)
    Mortgage ($3,562) + Fees ($250) + Taxes in 2024 ($815)


    Taxes:$9,777

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17379 CHANNEL WAY, WINTER GARDEN, FL 34787

    $678,00021 Days on yellowkey   MLS ID: O6412749

    REDUCED by $11,000 (1.6%) on 06/16/2026

    For Sale O6412749 - 17379 CHANNEL WAY, WINTER GARDEN, FL 34787 61 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2782
       Built: 2019
    Monthly Fee: $215
       Tax: $9,049 (2025)
    Community: Waterside At Johns Lake
    Single Family


    Estimated Monthly Payment: $4,684 (change assumption)
    Mortgage ($3,715) + Fees ($215) + Taxes in 2025 ($754)


    Taxes:$9,049

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8289 TOPSAIL PL, WINTER GARDEN, FL 34787

    $890,00021 Days on yellowkey   MLS ID: S5151179

    REDUCED by $30,000 (3.3%) on 06/16/2026

    For Sale S5151179 - 8289 TOPSAIL PL, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2755
       Built: 2020
    Monthly Fee: $350
       Tax: $11,564 (2024)
    Community: Lakeshore Preserve Ph 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,190 (change assumption)
    Mortgage ($4,877) + Fees ($350) + Taxes in 2024 ($964)


    Taxes:$11,564

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 12541 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787

    $819,99022 Days on yellowkey   MLS ID: O6412476

    REDUCED by $10,000 (1.2%) on 06/16/2026

    For Sale O6412476 - 12541 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 2026
    Monthly Fee: $96
       Tax: $10,790 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $5,488 (change assumption)
    Mortgage ($4,493) + Fees ($96) + Taxes in 2026 ($899)


    Taxes:$10,790

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 13843 LANYARD WAY, WINTER GARDEN, FL 34787

    $619,00024 Days on yellowkey   MLS ID: O6412130

    REDUCED by $29,000 (4.5%) on 06/16/2026

    For Sale O6412130 - 13843 LANYARD WAY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2568
       Built: 2022
    Monthly Fee: $225
       Tax: $9,717 (2025)
    Community: Encore/Ovation Ph 3
    Single Family


    Estimated Monthly Payment: $4,426 (change assumption)
    Mortgage ($3,392) + Fees ($225) + Taxes in 2025 ($810)


    Taxes:$9,717

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14776 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787

    $880,0009 Days on yellowkey   MLS ID: O6416354

    For Sale O6416354 - 14776 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787 72 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2876
       Built: 2017
    Monthly Fee: $187
       Tax: $11,232 (2025)
    Community: Orchard Hills Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,945 (change assumption)
    Mortgage ($4,822) + Fees ($187) + Taxes in 2025 ($936)


    Taxes:$11,232

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 925 EASLEY AVE, WINTER GARDEN, FL 34787

    $1,175,0009 Days on yellowkey   MLS ID: O6412977

    For Sale O6412977 - 925 EASLEY AVE, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2667
       Built: 2016
    Monthly Fee: $208
       Tax: $12,692 (2025)
    Community: Oakland Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,704 (change assumption)
    Mortgage ($6,438) + Fees ($208) + Taxes in 2025 ($1,058)


    Taxes:$12,692

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15160 TEA TREE DR, WINTER GARDEN, FL 34787

    $879,80611 Days on yellowkey   MLS ID: G5113740

    For Sale G5113740 - 15160 TEA TREE DR, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,971 (change assumption)
    Mortgage ($4,821) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14241 SUNRIDGE BLVD, WINTER GARDEN, FL 34787

    $749,80012 Days on yellowkey   MLS ID: O6416383

    0 Days Off yellowkey (back on 6/15/2026)

    For Sale O6416383 - 14241 SUNRIDGE BLVD, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2952
       Built: 2019
    Monthly Fee: $75
       Tax: $4,240 (2025)
    Community: Cypress Reserve Ph 1
    Single Family


    Estimated Monthly Payment: $4,537 (change assumption)
    Mortgage ($4,108) + Fees ($75) + Taxes in 2025 ($353)


    Taxes:$4,240

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    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.