994 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 988 STUCKI TERRACE Winter Garden, FL MLS# TB8539994
  • Recently Listed with Virtual Tour
1 of 12
$230,000
3

Beds

2.1

Baths

1,216

Sq.Ft.

988 STUCKI TERRACE

Winter Garden, FL

Courtesy of BEACHFRONT REALTY INC
View 5506 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6439560
  • Recently Listed with Virtual Tour
1 of 32
OPEN HOUSE: Saturday 9/12 11:00 AM - 2:00 PM
$629,000
5

Beds

3.1

Baths

2,369

Sq.Ft.

5506 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 13184 DENDY WAY Winter Garden, FL MLS# O6440321
  • Recently Listed with Virtual Tour
1 of 48
OPEN HOUSE: Saturday 9/12 11:00 AM - 2:00 PM
$649,900
4

Beds

2.1

Baths

2,211

Sq.Ft.

13184 DENDY WAY

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 15279 HARROWGATE WAY Winter Garden, FL MLS# O6440200
  • Recently Listed with Virtual Tour
1 of 24
$375,000
3

Beds

2.1

Baths

1,845

Sq.Ft.

15279 HARROWGATE WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1707 FULLERS OAK LOOP Winter Garden, FL MLS# S5157229
  • Recently Listed with Virtual Tour
1 of 64
$839,000
6

Beds

4.0

Baths

4,181

Sq.Ft.

1707 FULLERS OAK LOOP

Winter Garden, FL

View 17108 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5117579
$712,735
4

Beds

3.0

Baths

3,038

Sq.Ft.

17108 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1720 LAKE ROBERTS LANDING DRIVE Winter Garden, FL MLS# O6436608
  • Recently Listed with Virtual Tour
1 of 90
$1,399,999
5

Beds

4.1

Baths

4,919

Sq.Ft.

1720 LAKE ROBERTS LANDING DRIVE

Winter Garden, FL

View 1415 SHERBOURNE STREET Winter Garden, FL MLS# O6439948
  • Recently Listed with Virtual Tour
1 of 30
$415,000
3

Beds

2.1

Baths

1,369

Sq.Ft.

1415 SHERBOURNE STREET

Winter Garden, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 15240 SHONAN GOLD DRIVE Winter Garden, FL MLS# O6440016
$1,349,000
4

Beds

3.1

Baths

4,000

Sq.Ft.

15240 SHONAN GOLD DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 1527 VISCAYA COVE BOULEVARD Winter Garden, FL MLS# O6440090
$635,000
4

Beds

3.1

Baths

2,478

Sq.Ft.

1527 VISCAYA COVE BOULEVARD

Winter Garden, FL

View 8866 BISMARCK PALM DRIVE Winter Garden, FL MLS# O6440535
  • Recently Listed with Virtual Tour
1 of 64
$795,000
5

Beds

4.0

Baths

3,174

Sq.Ft.

8866 BISMARCK PALM DRIVE

Winter Garden, FL

Courtesy of MARIANI REALTY GROUP
View 12021 WINDSTONE STREET Winter Garden, FL MLS# O6440149
  • Recently Listed with Virtual Tour
1 of 87
$749,000
4

Beds

3.0

Baths

2,335

Sq.Ft.

12021 WINDSTONE STREET

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 1553 SPRING RIDGE CIRCLE Winter Garden, FL MLS# S5156629
  • Recently Listed with Virtual Tour
1 of 47
OPEN HOUSE: Saturday 9/12 12:00 PM - 3:00 PM
$475,000
3

Beds

2.0

Baths

1,729

Sq.Ft.

1553 SPRING RIDGE CIRCLE

Winter Garden, FL

Courtesy of WATSON REALTY CORP
View 13056 SANDCASTLE DRIVE Winter Garden, FL MLS# O6439937
  • Recently Listed with Virtual Tour
1 of 22
$775,000
2

Beds

2.0

Baths

1,889

Sq.Ft.

13056 SANDCASTLE DRIVE

Winter Garden, FL

View 144 TILDENVILLE SCHOOL ROAD Winter Garden, FL MLS# O6439913
  • Recently Listed with Virtual Tour
1 of 49
$899,900
Studio

Beds

0.0

Baths

144 TILDENVILLE SCHOOL ROAD

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 8931 DODDINGTON WAY Winter Garden, FL MLS# O6440410
  • Recently Listed with Virtual Tour
1 of 46
OPEN HOUSE: Saturday 9/12 10:00 AM - 2:00 PM
$479,000
3

Beds

2.1

Baths

1,944

Sq.Ft.

8931 DODDINGTON WAY

Winter Garden, FL

View 14075 LOCHEND WAY Winter Garden, FL MLS# O6439835
  • Recently Listed with Virtual Tour
1 of 66
$490,000
4

Beds

3.0

Baths

2,197

Sq.Ft.

14075 LOCHEND WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 17882 ADRIFT ROAD Winter Garden, FL MLS# O6439888
  • Recently Listed with Virtual Tour
1 of 46
$879,999
4

Beds

3.0

Baths

2,931

Sq.Ft.

17882 ADRIFT ROAD

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 148 ROPER DRIVE Winter Garden, FL MLS# O6435330
$795,000
3

Beds

2.0

Baths

1,807

Sq.Ft.

148 ROPER DRIVE

Winter Garden, FL

View 109 WINDTREE LANE N Winter Garden, FL MLS# O6438852
$224,900
2

Beds

2.0

Baths

918

Sq.Ft.

109 WINDTREE LANE N

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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

995

Estimated median home price

$606,440
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 - 200K22
$200K - 300K89
$300K - 400K72
$400K - 500K149
$500K - 600K162
$600K - 700K103
$700K - 800K114
$800K - 900K112
$900K - 1M59
$1M - Max112

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family694
Townhouse136
Condo129
Commercial7
Rental181
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 9/10/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

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. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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.

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 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 9/11/2026.