View 15262 NIGHT HERON DRIVE Winter Garden, FL MLS# O6378811
$3,150
3

Beds

2.0

Baths

2,089

Sq.Ft.

15262 NIGHT HERON DRIVE

Winter Garden, FL

Courtesy of PREMIUM PROPERTIES R.E. SERVICE
View 18153 CIDER MILL LANE Winter Garden, FL MLS# O6378946
$2,550
3

Beds

2.1

Baths

1,567

Sq.Ft.

18153 CIDER MILL LANE

Winter Garden, FL

Courtesy of JOHN SILVA REALTY & ASSOCIATES
View 13124 CALMING BREEZE WAY Winter Garden, FL MLS# O6376864
  • Recently Listed with Virtual Tour
1 of 38
$2,600
3

Beds

3.0

Baths

1,715

Sq.Ft.

13124 CALMING BREEZE WAY

Winter Garden, FL

Courtesy of DREAM FINDERS REALTY GROUP CORP
The time to sell is now! THE TIME TO SELL IS NOW!
View 1022 HUNTSPOINT STREET Winter Garden, FL MLS# O6378609
  • Recently Listed with Virtual Tour
1 of 43
$4,800
3

Beds

2.1

Baths

2,260

Sq.Ft.

1022 HUNTSPOINT STREET

Winter Garden, FL

Courtesy of TEAMCONNECT REALTY LLC
View 15274 GROVESIDE ROAD Winter Garden, FL MLS# S5142597
  • Recently Listed with Virtual Tour
1 of 11
$2,800
3

Beds

2.1

Baths

1,846

Sq.Ft.

15274 GROVESIDE ROAD

Winter Garden, FL

Courtesy of FRONTLINE FLORIDA REALTY, INC.
View 1244 PRIORY CIRCLE Winter Garden, FL MLS# O6378429
  • Recently Listed with Virtual Tour
1 of 43
$2,350
3

Beds

2.1

Baths

1,625

Sq.Ft.

1244 PRIORY CIRCLE

Winter Garden, FL

Courtesy of JOY ESTATE ENTERPRISE INC
View 3073 CHERRY ORCHARD LANE Winter Garden, FL MLS# O6378768
$2,745
3

Beds

2.0

Baths

2,115

Sq.Ft.

3073 CHERRY ORCHARD LANE

Winter Garden, FL

Courtesy of KHEMSON REALTY PA
View 233 WOODFALL LANE Winter Garden, FL MLS# O6378843
  • Recently Listed
1 of 42
$4,500
5

Beds

3.1

Baths

2,681

Sq.Ft.

233 WOODFALL LANE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 14531 CRESTED PLUME DRIVE Winter Garden, FL MLS# S5142754
  • Recently Listed with Virtual Tour
1 of 17
$2,900
4

Beds

2.1

Baths

1,868

Sq.Ft.

14531 CRESTED PLUME DRIVE

Winter Garden, FL

Courtesy of K REALTY
View 2262 ROMANUM DRIVE Winter Garden, FL MLS# O6378310
  • Recently Listed with Virtual Tour
1 of 49
$4,500
6

Beds

3.1

Baths

3,862

Sq.Ft.

2262 ROMANUM DRIVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 522 GRAND ROYAL CIRCLE Winter Garden, FL MLS# O6377478
  • Recently Listed with Virtual Tour
1 of 25
$2,595
4

Beds

2.0

Baths

1,874

Sq.Ft.

522 GRAND ROYAL CIRCLE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 1006 STUCKI TERRACE Winter Garden, FL MLS# O6377803
$1,506
2

Beds

2.0

Baths

814

Sq.Ft.

1006 STUCKI TERRACE

Winter Garden, FL

Courtesy of ANTICA DEVELOPMENT
View 7036 TWILIGHT BAY DRIVE Winter Garden, FL MLS# S5142666
  • Recently Listed with Virtual Tour
1 of 29
$3,000
4

Beds

3.1

Baths

1,914

Sq.Ft.

7036 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 16256 BRIGHT LEAF ROAD Winter Garden, FL MLS# O6377913
  • Recently Listed with Virtual Tour
1 of 33
$2,790
3

Beds

2.1

Baths

1,683

Sq.Ft.

16256 BRIGHT LEAF ROAD

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 11096 SILVER SURFER ALLEY Winter Garden, FL MLS# O6375509
  • Recently Listed with Virtual Tour
1 of 22
$3,200
4

Beds

3.0

Baths

2,042

Sq.Ft.

11096 SILVER SURFER ALLEY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 5014 RAILROAD VINE ALLEY Winter Garden, FL MLS# S5142689
  • Recently Listed with Virtual Tour
1 of 16
$3,000
4

Beds

2.1

Baths

2,011

Sq.Ft.

5014 RAILROAD VINE ALLEY

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 752 CITRUS COVE DRIVE Winter Garden, FL MLS# O6377190
  • Recently Listed with Virtual Tour
1 of 21
$2,995
4

Beds

3.0

Baths

1,800

Sq.Ft.

752 CITRUS COVE DRIVE

Winter Garden, FL

Courtesy of LEGENDS REALTY
View 1276 PRIORY CIRCLE Winter Garden, FL MLS# O6377534
  • Recently Listed with Virtual Tour
1 of 37
$2,600
3

Beds

2.1

Baths

1,793

Sq.Ft.

1276 PRIORY CIRCLE

Winter Garden, FL

Courtesy of BELLA VIEW REALTY LLC
View 4812 LIME RICKEY ALLEY Winter Garden, FL MLS# O6377477
  • Recently Listed with Virtual Tour
1 of 19
$3,500
4

Beds

2.1

Baths

2,084

Sq.Ft.

4812 LIME RICKEY ALLEY

Winter Garden, FL

Courtesy of ON ME REALTY
View 15523 BAY BRIDGE STREET Winter Garden, FL MLS# O6376958
  • Recently Listed with Virtual Tour
1 of 20
$3,100
3

Beds

2.1

Baths

1,691

Sq.Ft.

15523 BAY BRIDGE STREET

Winter Garden, FL

Courtesy of WEBB FLORIDA REALTY LLC

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

817

Estimated median home price

$590,000
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 - 100K7
$100K - 200K11
$200K - 300K78
$300K - 400K82
$400K - 500K137
$500K - 600K116
$600K - 700K101
$700K - 800K74
$800K - 900K67
$900K - 1M55
$1M - Max89

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family539
Townhouse120
Condo118
Commercial7
Rental237
Lots and Land31
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 2/2/2026)

Information deemed reliable but not guaranteed.

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 2/2/2026.