903 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 15594 SHOREBIRD LANE Winter Garden, FL MLS# R4910779
$1,350,000
4

Beds

3.1

Baths

2,829

Sq.Ft.

15594 SHOREBIRD LANE

Winter Garden, FL

Courtesy of FAIRBANKS REALTY
View 11021 BOSTWICK ALLEY Winter Garden, FL MLS# O6379924
$632,000
4

Beds

3.1

Baths

2,474

Sq.Ft.

11021 BOSTWICK ALLEY

Winter Garden, FL

Courtesy of LA ROSA REALTY KISSIMMEE
View 16563 BARBOURS CREEK WAY Winter Garden, FL MLS# O6386283
  • Recently Listed with Virtual Tour
1 of 14
$419,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16563 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 18167 CIDER MILL LANE Winter Garden, FL MLS# O6386278
  • Recently Listed with Virtual Tour
1 of 15
$487,500
3

Beds

2.1

Baths

1,817

Sq.Ft.

18167 CIDER MILL LANE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 15371 GILLIGAN COURT Winter Garden, FL MLS# O6385886
  • Recently Listed
1 of 57
OPEN HOUSE: Sunday 3/1 1:00 PM - 3:00 PM
$550,000
4

Beds

2.1

Baths

2,152

Sq.Ft.

15371 GILLIGAN COURT

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 13184 DENDY WAY Winter Garden, FL MLS# O6384386
  • Recently Listed with Virtual Tour
1 of 46
$669,000
4

Beds

2.1

Baths

2,211

Sq.Ft.

13184 DENDY WAY

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View 15210 SOUTHERN MARTIN STREET Winter Garden, FL MLS# O6386453
  • Recently Listed with Virtual Tour
1 of 48
OPEN HOUSE: Sunday 3/1 1:00 PM - 3:00 PM
$930,000
5

Beds

4.0

Baths

3,728

Sq.Ft.

15210 SOUTHERN MARTIN STREET

Winter Garden, FL

Courtesy of DOUGLAS ELLIMAN
View 13291 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5108893
  • New Construction with Virtual Tour
1 of 53
$428,405
3

Beds

2.1

Baths

1,644

Sq.Ft.

13291 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13007 SERENE GLADE ROAD Winter Garden, FL MLS# S5144801
  • Recently Listed with Virtual Tour
1 of 26
$599,990
4

Beds

3.0

Baths

2,083

Sq.Ft.

13007 SERENE GLADE ROAD

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 13386 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# S5144786
  • Recently Listed with Virtual Tour
1 of 35
$799,990
5

Beds

4.0

Baths

2,856

Sq.Ft.

13386 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 14326 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL MLS# O6386513
  • Recently Listed with Virtual Tour
1 of 56
$511,500
3

Beds

2.1

Baths

1,936

Sq.Ft.

14326 MURCOTT BLOSSOM BOULEVARD

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 9218 HOLLISTON CREEK PLACE Winter Garden, FL MLS# O6386394
$980,000
4

Beds

3.1

Baths

3,087

Sq.Ft.

9218 HOLLISTON CREEK PLACE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 8901 LAKESHORE POINTE DRIVE Winter Garden, FL MLS# O6385271
  • Recently Listed with Virtual Tour
1 of 58
$786,000
4

Beds

3.1

Baths

3,272

Sq.Ft.

8901 LAKESHORE POINTE DRIVE

Winter Garden, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 648 ORANGE BELT LOOP Winter Garden, FL MLS# S5144591
  • Recently Listed with Virtual Tour
1 of 61
$525,000
3

Beds

2.1

Baths

1,688

Sq.Ft.

648 ORANGE BELT LOOP

Winter Garden, FL

Courtesy of CORCORAN CONNECT LLC
View 430 COURTLEA OAKS BOULEVARD Winter Garden, FL MLS# O6385851
  • Recently Listed with Virtual Tour
1 of 54
OPEN HOUSE: Sunday 3/1 1:00 PM - 3:00 PM
$1,290,000
3

Beds

2.1

Baths

2,163

Sq.Ft.

430 COURTLEA OAKS BOULEVARD

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 5374 LAKE VIRGINIA STREET Winter Garden, FL MLS# O6385721
  • Recently Listed with Virtual Tour
1 of 26
$580,000
4

Beds

3.0

Baths

2,038

Sq.Ft.

5374 LAKE VIRGINIA STREET

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
View 14447 PRUNNINGWOOD PLACE Winter Garden, FL MLS# O6385194
$340,000
2

Beds

2.1

Baths

1,250

Sq.Ft.

14447 PRUNNINGWOOD PLACE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 15327 HAMLIN PARK DRIVE Winter Garden, FL MLS# TB8480916
  • Recently Listed with Virtual Tour
1 of 32
$492,990
3

Beds

3.1

Baths

2,072

Sq.Ft.

15327 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 709 PAMELA AVENUE Winter Garden, FL MLS# V4947516
  • Recently Listed with Virtual Tour
1 of 36
$315,000
4

Beds

3.0

Baths

1,056

Sq.Ft.

709 PAMELA AVENUE

Winter Garden, FL

Courtesy of GLORY INTL. REAL ESTATE CO
View 18309 OLIVER TWIST WAY Winter Garden, FL MLS# O6386008
  • Recently Listed with Virtual Tour
1 of 37
OPEN HOUSE: Sunday 3/1 12:00 PM - 2:00 PM
$725,000
5

Beds

4.0

Baths

2,832

Sq.Ft.

18309 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of LOKATION

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

904

Estimated median home price

$594,495
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 - 100K6
$100K - 200K13
$200K - 300K89
$300K - 400K78
$400K - 500K150
$500K - 600K137
$600K - 700K108
$700K - 800K89
$800K - 900K68
$900K - 1M63
$1M - Max103

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family606
Townhouse130
Condo128
Commercial9
Rental232
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 2/28/2026)

Information deemed reliable but not guaranteed.

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 2/28/2026.

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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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 2/28/2026.

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

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.

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 2/28/2026.