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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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
View 1182 ORANGE SEASON LANE Winter Garden, FL MLS# O6377033
  • Recently Listed with Virtual Tour
1 of 22
$3,000
3

Beds

2.1

Baths

2,444

Sq.Ft.

1182 ORANGE SEASON LANE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16147 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6376967
  • Recently Listed with Virtual Tour
1 of 18
$2,850
4

Beds

3.1

Baths

2,042

Sq.Ft.

16147 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of INTEREALTY SERVICE
View 9249 GRAN TEATRO DRIVE Winter Garden, FL MLS# S5142467
  • Recently Listed with Virtual Tour
1 of 19
$2,900
3

Beds

2.1

Baths

1,684

Sq.Ft.

9249 GRAN TEATRO DRIVE

Winter Garden, FL

Courtesy of PRIMUS CRE GROUP
View 9207 GRAN TEATRO DRIVE Winter Garden, FL MLS# O6376650
  • Recently Listed with Virtual Tour
1 of 32
$3,100
3

Beds

2.1

Baths

1,688

Sq.Ft.

9207 GRAN TEATRO DRIVE

Winter Garden, FL

Courtesy of MAINFRAME REAL ESTATE
View 14843 ASTROLYN STREET Winter Garden, FL MLS# O6374084
  • Recently Listed with Virtual Tour
1 of 16
$1,950
3

Beds

2.0

Baths

1,260

Sq.Ft.

14843 ASTROLYN STREET

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 15532 SWEET ORANGE AVENUE Winter Garden, FL MLS# O6376556
  • Recently Listed with Virtual Tour
1 of 50
$3,950
3

Beds

2.1

Baths

2,571

Sq.Ft.

15532 SWEET ORANGE AVENUE

Winter Garden, FL

Courtesy of BEST ORLANDO PROPERTY MANAGEMENT LLC
View 4306 OLD SYCAMORE LOOP Winter Garden, FL MLS# O6376530
  • Recently Listed with Virtual Tour
1 of 55
$6,600
5

Beds

3.1

Baths

4,050

Sq.Ft.

4306 OLD SYCAMORE LOOP

Winter Garden, FL

Courtesy of SELECTA REALTY LLC
View 14931 LEBEAU LOOP Winter Garden, FL MLS# O6376599
  • Recently Listed with Virtual Tour
1 of 57
$5,400
4

Beds

3.1

Baths

2,832

Sq.Ft.

14931 LEBEAU LOOP

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 139 E STORY ROAD A Winter Garden, FL MLS# O6376451
  • Recently Listed with Virtual Tour
1 of 12
$1,755
2

Beds

1.0

Baths

985

Sq.Ft.

139 E STORY ROAD A

Winter Garden, FL

Courtesy of FLAMINGO REALTY OF 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

825

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 - 300K77
$300K - 400K82
$400K - 500K139
$500K - 600K119
$600K - 700K103
$700K - 800K75
$800K - 900K67
$900K - 1M54
$1M - Max91

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family544
Townhouse123
Condo117
Commercial7
Rental238
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/30/2026)

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 1/30/2026.