1,089 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 15138 SHONAN GOLD DRIVE Winter Garden, FL MLS# O6417357
$2,799,950
5

Beds

5.2

Baths

5,551

Sq.Ft.

15138 SHONAN GOLD DRIVE

Winter Garden, FL

View 12959 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6417449
  • Recently Listed with Virtual Tour
1 of 13
$750,000
4

Beds

3.1

Baths

2,858

Sq.Ft.

12959 HARVEST RAIN AVENUE

Winter Garden, FL

View 8750 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# O6416046
  • Recently Listed with Virtual Tour
1 of 88
$1,895,000
5

Beds

5.1

Baths

4,641

Sq.Ft.

8750 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 7558 BISHOP SQUARE DRIVE Winter Garden, FL MLS# O6417556
$554,900
4

Beds

2.0

Baths

1,952

Sq.Ft.

7558 BISHOP SQUARE DRIVE

Winter Garden, FL

View 142 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# O6414551
  • Recently Listed with Virtual Tour
1 of 58
$297,900
3

Beds

2.0

Baths

1,453

Sq.Ft.

142 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

View 13037 SERENE GLADE ROAD Winter Garden, FL MLS# G5113926
  • Recently Listed with Virtual Tour
1 of 34
$559,990
3

Beds

2.1

Baths

1,836

Sq.Ft.

13037 SERENE GLADE ROAD

Winter Garden, FL

View 2022 BOSS HEWETT STREET Winter Garden, FL MLS# O6417697
  • Recently Listed with Virtual Tour
1 of 36
$679,000
4

Beds

3.0

Baths

2,281

Sq.Ft.

2022 BOSS HEWETT STREET

Winter Garden, FL

View 15154 TEA TREE DRIVE Winter Garden, FL MLS# G5113803
$994,733
5

Beds

4.1

Baths

3,839

Sq.Ft.

15154 TEA TREE DRIVE

Winter Garden, FL

View 925 EASLEY AVENUE Winter Garden, FL MLS# O6412977
  • Recently Listed with Virtual Tour
1 of 47
$1,175,000
4

Beds

3.1

Baths

2,667

Sq.Ft.

925 EASLEY AVENUE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 519 TEAGARDEN COURT Winter Garden, FL MLS# O6416709
  • Recently Listed with Virtual Tour
1 of 23
$898,000
4

Beds

3.0

Baths

3,061

Sq.Ft.

519 TEAGARDEN COURT

Winter Garden, FL

View 6334 WILD PERSIMMON WAY Winter Garden, FL MLS# G5113852
  • New Construction with Virtual Tour
1 of 49
$913,313
6

Beds

4.1

Baths

3,543

Sq.Ft.

6334 WILD PERSIMMON WAY

Winter Garden, FL

View 15367 GILLIGAN COURT Winter Garden, FL MLS# O6417175
  • Recently Listed with Virtual Tour
1 of 30
$590,000
4

Beds

2.1

Baths

2,156

Sq.Ft.

15367 GILLIGAN COURT

Winter Garden, FL

View 9362 WOODCRANE DRIVE Winter Garden, FL MLS# O6417277
  • Recently Listed with Virtual Tour
1 of 8
$459,300
3

Beds

2.1

Baths

2,058

Sq.Ft.

9362 WOODCRANE DRIVE

Winter Garden, FL

View 1105 LINCOLN TERRACE Winter Garden, FL MLS# O6416937
  • Recently Listed with Virtual Tour
1 of 25
$255,000
3

Beds

1.0

Baths

814

Sq.Ft.

1105 LINCOLN TERRACE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 9503 BEAUTIFUL WAY Winter Garden, FL MLS# O6416825
$745,990
4

Beds

3.0

Baths

3,062

Sq.Ft.

9503 BEAUTIFUL WAY

Winter Garden, FL

Courtesy of WYNNMORE REALTY LLC
View 13856 GLYNSHEL DRIVE Winter Garden, FL MLS# O6416757
  • Recently Listed with Virtual Tour
1 of 31
$850,000
5

Beds

4.0

Baths

3,538

Sq.Ft.

13856 GLYNSHEL DRIVE

Winter Garden, FL

View 4958 CITRUS LEAF BLVD Winter Garden, FL MLS# S5151791
  • Recently Listed with Virtual Tour
1 of 41
$540,000
3

Beds

2.1

Baths

1,788

Sq.Ft.

4958 CITRUS LEAF BLVD

Winter Garden, FL

View 6316 MANUSCRIPT STREET Winter Garden, FL MLS# O6409661
  • Recently Listed with Virtual Tour
1 of 32
$619,000
4

Beds

2.1

Baths

2,608

Sq.Ft.

6316 MANUSCRIPT STREET

Winter Garden, FL

View 13404 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5113736
  • Recently Listed with Virtual Tour
1 of 19
$769,990
4

Beds

3.1

Baths

2,689

Sq.Ft.

13404 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13380 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5113738
  • Recently Listed with Virtual Tour
1 of 26
$699,990
4

Beds

3.0

Baths

2,235

Sq.Ft.

13380 PEACEFUL MELODY DRIVE

Winter Garden, FL

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

1,094

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 - 200K25
$200K - 300K90
$300K - 400K77
$400K - 500K148
$500K - 600K191
$600K - 700K133
$700K - 800K116
$800K - 900K103
$900K - 1M74
$1M - Max136

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family773
Townhouse142
Condo140
Commercial11
Rental211
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 6/23/2026)

Information deemed reliable but not guaranteed.

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.

This data updated periodically, at an interval not to exceed 7 days.

IDX information 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

© 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 6/23/2026.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 6/23/2026.

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

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 6/23/2026.