257 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 2200 ROMANUM DRIVE Winter Garden, FL MLS# O6408190
  • Recently Listed with Virtual Tour
1 of 33
$560,000
4

Beds

4.0

Baths

2,561

Sq.Ft.

2200 ROMANUM DRIVE

Winter Garden, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 17001 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112433
$485,705
3

Beds

2.1

Baths

1,644

Sq.Ft.

17001 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17007 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112438
$491,490
3

Beds

2.1

Baths

1,764

Sq.Ft.

17007 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 7280 WINDY WILLOW STREET Winter Garden, FL MLS# G5112439
  • Recently Listed with Virtual Tour
1 of 5
$493,583
3

Beds

2.1

Baths

1,772

Sq.Ft.

7280 WINDY WILLOW STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13958 MAGNOLIA RIDGE LOOP Winter Garden, FL MLS# O6406860
  • Recently Listed with Virtual Tour
1 of 58
$600,000
3

Beds

2.0

Baths

2,075

Sq.Ft.

13958 MAGNOLIA RIDGE LOOP

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 729 MEADOW GLADE DRIVE Winter Garden, FL MLS# O6407943
$530,000
3

Beds

2.0

Baths

2,070

Sq.Ft.

729 MEADOW GLADE DRIVE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 16230 Carraway Bay Alley Winter Garden, FL MLS# 1226408
$529,999
4

Beds

3.1

Baths

2,474

Sq.Ft.

16230 Carraway Bay Alley

Winter Garden, FL

View 14755 MASTHEAD LANDING CIRCLE Winter Garden, FL MLS# O6408082
  • Recently Listed with Virtual Tour
1 of 12
$580,000
4

Beds

2.0

Baths

2,258

Sq.Ft.

14755 MASTHEAD LANDING CIRCLE

Winter Garden, FL

Courtesy of SUSANA JORDAN STUTSMAN
View 15518 FOUNTAIN COVE COURT Winter Garden, FL MLS# O6407942
  • Recently Listed with Virtual Tour
1 of 73
$574,990
3

Beds

3.0

Baths

2,040

Sq.Ft.

15518 FOUNTAIN COVE COURT

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 5545 BOWMAN DRIVE Winter Garden, FL MLS# O6407484
  • Recently Listed with Virtual Tour
1 of 29
OPEN HOUSE: Saturday 5/16 9:00 AM - 7:00 PM
$485,000
2

Beds

2.1

Baths

1,998

Sq.Ft.

5545 BOWMAN DRIVE

Winter Garden, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 6044 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5112346
$579,820
4

Beds

3.0

Baths

2,102

Sq.Ft.

6044 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6102 WHISPERING GLEN Winter Garden, FL MLS# O6407803
  • Recently Listed with Virtual Tour
1 of 28
$576,890
4

Beds

2.1

Baths

1,913

Sq.Ft.

6102 WHISPERING GLEN

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 6174 WHISPERING GLEN Winter Garden, FL MLS# O6407807
  • Recently Listed with Virtual Tour
1 of 20
$546,290
3

Beds

2.1

Baths

1,628

Sq.Ft.

6174 WHISPERING GLEN

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 11117 BOSTWICK ALLEY Winter Garden, FL MLS# O6407552
  • Recently Listed with Virtual Tour
1 of 19
$520,000
3

Beds

2.0

Baths

1,685

Sq.Ft.

11117 BOSTWICK ALLEY

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 15025 PIGEON PLUM LANE Winter Garden, FL MLS# O6404948
$599,990
4

Beds

2.1

Baths

2,605

Sq.Ft.

15025 PIGEON PLUM LANE

Winter Garden, FL

Courtesy of BLOOM HOME GROUP REALTY LLC
View 7667 SILVER MEADOW STREET Winter Garden, FL MLS# G5112278
$551,130
4

Beds

3.0

Baths

2,102

Sq.Ft.

7667 SILVER MEADOW STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1431 VISCAYA COVE BOULEVARD Winter Garden, FL MLS# O6407306
  • Recently Listed with Virtual Tour
1 of 43
OPEN HOUSE: Saturday 5/16 11:00 AM - 2:00 PM
$535,000
4

Beds

3.0

Baths

2,030

Sq.Ft.

1431 VISCAYA COVE BOULEVARD

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 5960 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5112227
  • Recently Listed with Virtual Tour
1 of 5
$557,123
3

Beds

2.0

Baths

1,772

Sq.Ft.

5960 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 12308 BRACCO STREET Winter Garden, FL MLS# O6406923
  • Recently Listed with Virtual Tour
1 of 35
$525,000
4

Beds

2.1

Baths

2,094

Sq.Ft.

12308 BRACCO STREET

Winter Garden, FL

Courtesy of ELITE INTERNATIONAL REALTY INC
View 13552 AUTUMN HARVEST AVENUE Winter Garden, FL MLS# O6404264
  • Recently Listed with Virtual Tour
1 of 31
$530,000
3

Beds

3.0

Baths

1,955

Sq.Ft.

13552 AUTUMN HARVEST AVENUE

Winter Garden, FL

Courtesy of REALTY ONE GROUP EVOLUTION

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

1,032

Estimated median home price

$610,000
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 - 200K20
$200K - 300K99
$300K - 400K77
$400K - 500K144
$500K - 600K163
$600K - 700K129
$700K - 800K118
$800K - 900K85
$900K - 1M80
$1M - Max116

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family709
Townhouse142
Condo138
Commercial10
Rental211
Lots and Land30
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/16/2026)

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.

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

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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 5/16/2026.

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 5/16/2026.

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 5/16/2026.