View 502 VARSITY STREET Winter Garden, FL MLS# O6433127
  • Recently Listed with Virtual Tour
1 of 5
$1,675
2

Beds

1.0

Baths

780

Sq.Ft.

502 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 508 VARSITY STREET Winter Garden, FL MLS# O6433135
  • Recently Listed with Virtual Tour
1 of 10
$1,675
2

Beds

1.0

Baths

780

Sq.Ft.

508 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 9247 LEGADO DRIVE Winter Garden, FL MLS# O6433071
  • Recently Listed with Virtual Tour
1 of 100
$5,500
4

Beds

2.1

Baths

2,549

Sq.Ft.

9247 LEGADO DRIVE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 7078 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6432698
$2,850
3

Beds

3.0

Baths

2,032

Sq.Ft.

7078 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 14727 FIELD DAISY DRIVE Winter Garden, FL MLS# O6432781
  • New Construction with Virtual Tour
1 of 62
$3,800
5

Beds

4.1

Baths

2,841

Sq.Ft.

14727 FIELD DAISY DRIVE

Winter Garden, FL

View 15025 EVERGREEN OAK LOOP Winter Garden, FL MLS# O6433081
  • Recently Listed with Virtual Tour
1 of 13
$3,200
4

Beds

3.1

Baths

2,477

Sq.Ft.

15025 EVERGREEN OAK LOOP

Winter Garden, FL

View 14796 TULLAMORE LOOP Winter Garden, FL MLS# O6429064
  • Recently Listed with Virtual Tour
1 of 64
$3,500
4

Beds

2.1

Baths

2,974

Sq.Ft.

14796 TULLAMORE LOOP

Winter Garden, FL

View 10253 LOVE STORY STREET Winter Garden, FL MLS# O6432049
$3,050
4

Beds

3.0

Baths

2,042

Sq.Ft.

10253 LOVE STORY STREET

Winter Garden, FL

View 739 REFLECTIONS LANE Winter Garden, FL MLS# O6432109
  • Recently Listed with Virtual Tour
1 of 14
$3,400
4

Beds

2.1

Baths

4,046

Sq.Ft.

739 REFLECTIONS LANE

Winter Garden, FL

View 15153 SUMMER HARVEST STREET Winter Garden, FL MLS# O6424573
$3,050
3

Beds

3.1

Baths

2,332

Sq.Ft.

15153 SUMMER HARVEST STREET

Winter Garden, FL

View 13307 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# S5155235
  • New Construction with Virtual Tour
1 of 13
$2,700
3

Beds

2.1

Baths

1,644

Sq.Ft.

13307 PEACEFUL MELODY DRIVE

Winter Garden, FL

View Address not provided Winter Garden, FL MLS# S5155119
$1,595
1

Beds

1.0

Baths

738

Sq.Ft.

Address not provided

Winter Garden, FL

View 15555 GWINNETT DRIVE Winter Garden, FL MLS# O6426770
  • Recently Listed with Virtual Tour
1 of 26
$3,200
3

Beds

3.1

Baths

2,096

Sq.Ft.

15555 GWINNETT DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 16902 HAMLIN OASIS LOOP Winter Garden, FL MLS# O6431430
$3,250
3

Beds

2.1

Baths

2,096

Sq.Ft.

16902 HAMLIN OASIS LOOP

Winter Garden, FL

Courtesy of CASTRO REALTY GROUP
View 407 DOUGLAS WAY 66 Winter Garden, FL MLS# O6431468
$1,895
2

Beds

2.0

Baths

930

Sq.Ft.

407 DOUGLAS WAY 66

Winter Garden, FL

View 13075 SPRING GROVE WAY Winter Garden, FL MLS# TB8532749
$2,900
3

Beds

2.1

Baths

1,994

Sq.Ft.

13075 SPRING GROVE WAY

Winter Garden, FL

Courtesy of PREMIER FLAT FEE REALTY LLC
View 11165 GREEN CITRON ALLEY Winter Garden, FL MLS# O6432084
  • Recently Listed with Virtual Tour
1 of 49
$3,250
4

Beds

3.0

Baths

2,043

Sq.Ft.

11165 GREEN CITRON ALLEY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 17552 LAKE STAR ROAD Winter Garden, FL MLS# O6431054
$4,500
4

Beds

3.1

Baths

2,605

Sq.Ft.

17552 LAKE STAR ROAD

Winter Garden, FL

View 13882 TITLE WAY Winter Garden, FL MLS# S5155410
  • Recently Listed with Virtual Tour
1 of 23
$2,590
3

Beds

2.1

Baths

1,518

Sq.Ft.

13882 TITLE WAY

Winter Garden, FL

Courtesy of K REALTY
View 12946 GROVEHURST AVENUE Winter Garden, FL MLS# O6431241
  • Recently Listed with Virtual Tour
1 of 16
$3,100
4

Beds

2.1

Baths

2,529

Sq.Ft.

12946 GROVEHURST AVENUE

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

1,029

Estimated median home price

$608,000
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 - 100K1
$100K - 200K22
$200K - 300K89
$300K - 400K78
$400K - 500K153
$500K - 600K168
$600K - 700K112
$700K - 800K113
$800K - 900K112
$900K - 1M62
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family715
Townhouse145
Condo133
Commercial9
Rental188
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/29/2026)

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 8/30/2026.