View 14629 BAHAMA SWALLOW BOULEVARD Winter Garden, FL MLS# O6421797
  • Recently Listed with Virtual Tour
1 of 25
$492,900
3

Beds

2.0

Baths

2,223

Sq.Ft.

14629 BAHAMA SWALLOW BOULEVARD

Winter Garden, FL

View 6843 POINT HANCOCK DRIVE Winter Garden, FL MLS# G5114589
  • Recently Listed with Virtual Tour
1 of 16
$435,000
3

Beds

2.0

Baths

1,720

Sq.Ft.

6843 POINT HANCOCK DRIVE

Winter Garden, FL

View 7467 JOHN HANCOCK DRIVE Winter Garden, FL MLS# O6421848
  • Recently Listed with Virtual Tour
1 of 90
$1,350,000
4

Beds

3.1

Baths

3,964

Sq.Ft.

7467 JOHN HANCOCK DRIVE

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 8873 FOUNTAIN PALM ALLEY Winter Garden, FL MLS# O6423477
$565,000
3

Beds

2.1

Baths

2,162

Sq.Ft.

8873 FOUNTAIN PALM ALLEY

Winter Garden, FL

View 7840 WINTER WREN STREET Winter Garden, FL MLS# O6421167
$533,900
3

Beds

2.1

Baths

2,004

Sq.Ft.

7840 WINTER WREN STREET

Winter Garden, FL

View 1152 PRADO LANE Winter Garden, FL MLS# O6413825
  • Recently Listed with Virtual Tour
1 of 13
$2,615,320
6

Beds

6.1

Baths

4,658

Sq.Ft.

1152 PRADO LANE

Winter Garden, FL

View 6207 SUNNY TIME AVENUE Winter Garden, FL MLS# O6421162
  • New Construction with Virtual Tour
1 of 23
$547,190
3

Beds

2.1

Baths

1,628

Sq.Ft.

6207 SUNNY TIME AVENUE

Winter Garden, FL

View 2006 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# O6420951
  • Recently Listed with Virtual Tour
1 of 50
$750,000
5

Beds

4.0

Baths

3,011

Sq.Ft.

2006 WINTERMERE POINTE DRIVE

Winter Garden, FL

View 6137 WATERSIDE ISLAND LANE Winter Garden, FL MLS# O6418786
  • Recently Listed with Virtual Tour
1 of 34
$599,900
4

Beds

3.1

Baths

2,607

Sq.Ft.

6137 WATERSIDE ISLAND LANE

Winter Garden, FL

View 16082 HAMPTON CROSSING DRIVE Winter Garden, FL MLS# O6420606
  • Recently Listed with Virtual Tour
1 of 46
$739,900
4

Beds

3.0

Baths

2,240

Sq.Ft.

16082 HAMPTON CROSSING DRIVE

Winter Garden, FL

Courtesy of Lake Mary - WEICHERT, REALTORS® - Hallmark Properties
View 15162 SPINNAKER COVE LANE Winter Garden, FL MLS# S5152807
$765,000
5

Beds

3.0

Baths

3,902

Sq.Ft.

15162 SPINNAKER COVE LANE

Winter Garden, FL

Courtesy of SERHANT
View 15063 GROVESIDE ROAD Winter Garden, FL MLS# O6420626
  • New Construction with Virtual Tour
1 of 19
$516,430
3

Beds

2.1

Baths

1,846

Sq.Ft.

15063 GROVESIDE ROAD

Winter Garden, FL

View 12632 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# S5152652
  • Recently Listed with Virtual Tour
1 of 20
$575,000
4

Beds

2.1

Baths

2,148

Sq.Ft.

12632 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

View 502 PALM DRIVE Winter Garden, FL MLS# O6415316
  • Recently Listed with Virtual Tour
1 of 59
$710,000
4

Beds

2.1

Baths

3,009

Sq.Ft.

502 PALM DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13361 SUNNY RETREAT LANE Winter Garden, FL MLS# O6419110
  • Recently Listed with Virtual Tour
1 of 74
$869,900
4

Beds

3.0

Baths

3,172

Sq.Ft.

13361 SUNNY RETREAT LANE

Winter Garden, FL

View 14543 GOLDEN HARBOR LANE Winter Garden, FL MLS# O6420711
$525,000
3

Beds

2.1

Baths

2,039

Sq.Ft.

14543 GOLDEN HARBOR LANE

Winter Garden, FL

View 17059 HARBOR OAK PARKWAY Winter Garden, FL MLS# G5114379
  • Recently Listed with Virtual Tour
1 of 67
$620,000
4

Beds

3.0

Baths

2,692

Sq.Ft.

17059 HARBOR OAK PARKWAY

Winter Garden, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 14301 WHITE MOSS WAY Winter Garden, FL MLS# G5114391
  • Recently Listed with Virtual Tour
1 of 60
$949,999
5

Beds

3.1

Baths

4,053

Sq.Ft.

14301 WHITE MOSS WAY

Winter Garden, FL

View 9976 BEACH PORT DRIVE Winter Garden, FL MLS# O6420960
$1,274,000
5

Beds

3.1

Baths

3,910

Sq.Ft.

9976 BEACH PORT DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 14591 BLACK QUILL DRIVE Winter Garden, FL MLS# O6420836
  • Recently Listed with Virtual Tour
1 of 61
$1,335,000
4

Beds

3.1

Baths

4,057

Sq.Ft.

14591 BLACK QUILL 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

957

Estimated median home price

$609,611
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 - 200K21
$200K - 300K91
$300K - 400K65
$400K - 500K137
$500K - 600K160
$600K - 700K101
$700K - 800K103
$800K - 900K89
$900K - 1M63
$1M - Max126

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family653
Townhouse134
Condo135
Commercial11
Rental201
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/15/2026)

Information deemed reliable but not guaranteed.

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 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 7/15/2026.