271 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 15419 UGLIS ALLEY Winter Garden, FL MLS# O6403047
$565,000
3

Beds

2.1

Baths

2,270

Sq.Ft.

15419 UGLIS ALLEY

Winter Garden, FL

Courtesy of STOCKWORTH REALTY GROUP
View 14099 LOCHEND WAY Winter Garden, FL MLS# O6404015
$479,900
3

Beds

2.1

Baths

1,720

Sq.Ft.

14099 LOCHEND WAY

Winter Garden, FL

Courtesy of INTERNATIONAL REAL ESTATE LLC
View 12003 HOLYSTONE STREET Winter Garden, FL MLS# L4961121
$445,000
3

Beds

2.1

Baths

1,814

Sq.Ft.

12003 HOLYSTONE STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY SMART
The time to sell is now! THE TIME TO SELL IS NOW!
View 17090 HARBOR OAK PARKWAY Winter Garden, FL MLS# G5111718
$534,900
3

Beds

3.0

Baths

2,148

Sq.Ft.

17090 HARBOR OAK PARKWAY

Winter Garden, FL

Courtesy of TOWERSIDE REALTY INC
View 10361 AUSTRINA OAK LOOP Winter Garden, FL MLS# S5148904
$550,000
4

Beds

2.1

Baths

2,204

Sq.Ft.

10361 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of PM ELITE REALTY LLC
View 113 W DIVISION STREET Winter Garden, FL MLS# S5148787
$539,900
3

Beds

2.0

Baths

1,487

Sq.Ft.

113 W DIVISION STREET

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 1032 BURLAND CIRCLE Winter Garden, FL MLS# O6401764
$529,990
5

Beds

2.0

Baths

2,487

Sq.Ft.

1032 BURLAND CIRCLE

Winter Garden, FL

Courtesy of RE/MAX ASSURED
View 15684 ORANGE HARVEST LOOP Winter Garden, FL MLS# W7885221
$459,900
3

Beds

2.1

Baths

2,012

Sq.Ft.

15684 ORANGE HARVEST LOOP

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 9354 MEADOW HUNT WAY Winter Garden, FL MLS# O6400695
  • Virtual Tour
1 of 50
OPEN HOUSE: Sunday 6/7 12:00 PM - 2:30 PM
$525,000
3

Beds

2.1

Baths

2,079

Sq.Ft.

9354 MEADOW HUNT WAY

Winter Garden, FL

Courtesy of INFINITY REALTY GROUP LLC
View 837 GRANDE REGAL POINT Winter Garden, FL MLS# O6400571
$450,000
3

Beds

2.0

Baths

1,874

Sq.Ft.

837 GRANDE REGAL POINT

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 199 E CREST AVENUE Winter Garden, FL MLS# O6401923
$525,000
3

Beds

2.0

Baths

1,659

Sq.Ft.

199 E CREST AVENUE

Winter Garden, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 521 COPPERDALE AVE Winter Garden, FL MLS# O6402408
$525,000
5

Beds

3.0

Baths

2,328

Sq.Ft.

521 COPPERDALE AVE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 16834 HOBE SOUND COURT Winter Garden, FL MLS# O6401373
  • New Construction with Virtual Tour
1 of 18
$599,990
4

Beds

3.1

Baths

2,494

Sq.Ft.

16834 HOBE SOUND COURT

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 2281 OAKINGTON STREET Winter Garden, FL MLS# S5148475
$475,000
3

Beds

2.0

Baths

1,628

Sq.Ft.

2281 OAKINGTON STREET

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 776 RAINFALL DRIVE Winter Garden, FL MLS# O6400904
$550,000
3

Beds

2.0

Baths

2,238

Sq.Ft.

776 RAINFALL DRIVE

Winter Garden, FL

Courtesy of ONLI REALTY GROUP LLC
View 7036 BOLANZO ALLEY Winter Garden, FL MLS# O6401429
$475,000
4

Beds

3.1

Baths

1,920

Sq.Ft.

7036 BOLANZO ALLEY

Winter Garden, FL

Courtesy of SERHANT
View 2478 PRAIRIE VIEW DRIVE Winter Garden, FL MLS# O6400594
$499,900
4

Beds

3.0

Baths

2,766

Sq.Ft.

2478 PRAIRIE VIEW DRIVE

Winter Garden, FL

Courtesy of ENTERA REALTY LLC
View 236 DONALD DRIVE Winter Garden, FL MLS# O6401940
$465,000
2

Beds

1.0

Baths

1,080

Sq.Ft.

236 DONALD DRIVE

Winter Garden, FL

Courtesy of GLOBAL FLORIDA REALTY
View 8012 BLUEJACK OAK DRIVE Winter Garden, FL MLS# FC317938
$535,000
4

Beds

3.1

Baths

2,222

Sq.Ft.

8012 BLUEJACK OAK DRIVE

Winter Garden, FL

Courtesy of Palm Coast - WEICHERT, REALTORS® - Hallmark Properties
View 14280 BRAEMAR STREET Winter Garden, FL MLS# TB8500322
    1 of 33
    OPEN HOUSE: Sunday 6/7 11:00 AM - 2:00 PM
    $539,000
    3

    Beds

    2.1

    Baths

    1,964

    Sq.Ft.

    14280 BRAEMAR STREET

    Winter Garden, FL

    Courtesy of LPT REALTY, LLC

    About Winter Garden

    The balance between reverence for yesterday and vibrant growth is reflected in the Winter Garden slogan, "A City with a Future…Preserving Its Past."  Walking down historic Plant Street or catching a glimpse of landmark buildings like Tanner Hall immediately creates an image of small-town life at its finest in the heart of this quaint Main Street community. At the same time, redevelopment and growth are evident at every turn.  Antique stores, ice cream shops, and charming cafés combine with dynamic new businesses and residential development.  Covering approximately 17 square miles, Winter Garden offers access to the West Orange Trail for biking or jogging in a naturally beautiful setting.  Other amenities include large parks, a public boat ramp on Lake Apopka, and recreational complexes for tennis, swimming, and sports play.  This vast area once covered by citrus groves is rapidly transforming into a suburban environment that preserves the friendly, intimate spirit of yesterday.  Residents enjoy easy access to Highway 50, the East West Expressway, and the Florida Turnpike.

    Listings in Winter Garden, FL

    1,047

    Estimated median home price

    $615,000
    Winter Garden FL Homes for Sale & Properties

    Weichert Realtors is one of the nation's leading providers of Winter Garden, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Garden, FL.

    Homes for Sale by Price in Winter Garden, FL

    PriceCount
    $0 - 100K1
    $100K - 200K24
    $200K - 300K88
    $300K - 400K80
    $400K - 500K145
    $500K - 600K170
    $600K - 700K129
    $700K - 800K117
    $800K - 900K92
    $900K - 1M72
    $1M - Max129

    Homes for Sale by Type in Winter Garden, FL

    Property TypeCount
    Single Family731
    Townhouse139
    Condo137
    Commercial11
    Rental197
    Lots and Land26
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home1
    Farms0

    (Data as of 6/7/2026)

    Information deemed reliable but not guaranteed.

    The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

    The data relating to real estate for sale/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. 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. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

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    © Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

    The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

    The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

    Data is updated as of 6/7/2026.

    The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

    The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

    Copyright 2026 BeachesMLS, Inc. All rights reserved.

    All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

    The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

    Data is updated as of 6/7/2026.

    Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

    Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

    Data is updated as of 6/7/2026.