View 445 SPRING LEAP CIRCLE Winter Garden, FL MLS# O6432875
  • Recently Listed with Virtual Tour
1 of 39
$419,900
4

Beds

2.0

Baths

1,695

Sq.Ft.

445 SPRING LEAP CIRCLE

Winter Garden, FL

View 242 WINTER NELLIS CIRCLE Winter Garden, FL MLS# O6434246
  • Recently Listed with Virtual Tour
1 of 31
$359,999
3

Beds

2.1

Baths

1,991

Sq.Ft.

242 WINTER NELLIS CIRCLE

Winter Garden, FL

View 16510 BARBOURS CREEK WAY Winter Garden, FL MLS# O6435580
  • Recently Listed with Virtual Tour
1 of 27
$447,500
3

Beds

2.1

Baths

1,567

Sq.Ft.

16510 BARBOURS CREEK WAY

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 16516 BARBOURS CREEK WAY Winter Garden, FL MLS# O6435583
  • Recently Listed with Virtual Tour
1 of 27
$424,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16516 BARBOURS CREEK WAY

Winter Garden, FL

View 208 3RD STREET Winter Garden, FL MLS# O6435218
  • Recently Listed
1 of 2
$435,000
Studio

Beds

0.0

Baths

1,750

Sq.Ft.

208 3RD STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 208 3RD STREET Winter Garden, FL MLS# O6435263
  • Recently Listed
1 of 2
$435,000
Studio

Beds

0.0

Baths

208 3RD STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 208 3RD STREET Winter Garden, FL MLS# O6435284
$435,000
8

Beds

3.0

Baths

1,750

Sq.Ft.

208 3RD STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 13855 GOLDEN RUSSET DRIVE Winter Garden, FL MLS# G5116589
  • Recently Listed with Virtual Tour
1 of 44
$365,000
2

Beds

2.1

Baths

1,652

Sq.Ft.

13855 GOLDEN RUSSET DRIVE

Winter Garden, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 15056 WINDFLOWER ALLEY Winter Garden, FL MLS# O6434353
  • Recently Listed with Virtual Tour
1 of 32
OPEN HOUSE: Sunday 8/23 12:00 PM - 2:00 PM
$398,000
3

Beds

2.1

Baths

1,536

Sq.Ft.

15056 WINDFLOWER ALLEY

Winter Garden, FL

View 11102 HANLON TERRACE ALLEY Winter Garden, FL MLS# S5155891
  • Recently Listed with Virtual Tour
1 of 25
$450,000
3

Beds

2.1

Baths

1,868

Sq.Ft.

11102 HANLON TERRACE ALLEY

Winter Garden, FL

Courtesy of PRIMUS CRE GROUP
View 15819 GEM VIEW STREET Winter Garden, FL MLS# O6434476
  • Adult Community with Virtual Tour
1 of 33
$400,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

15819 GEM VIEW STREET

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15038 WINDFLOWER ALLEY Winter Garden, FL MLS# O6434050
  • Recently Listed with Virtual Tour
1 of 29
$455,000
3

Beds

2.1

Baths

1,536

Sq.Ft.

15038 WINDFLOWER ALLEY

Winter Garden, FL

View 1221 PRIORY CIRCLE Winter Garden, FL MLS# S5155802
  • Recently Listed with Virtual Tour
1 of 42
$380,000
3

Beds

2.1

Baths

1,675

Sq.Ft.

1221 PRIORY CIRCLE

Winter Garden, FL

View 1312 CORSINO ST Winter Garden, FL MLS# O6433388
  • Recently Listed with Virtual Tour
1 of 29
$450,000
3

Beds

2.0

Baths

1,307

Sq.Ft.

1312 CORSINO ST

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 10648 WORDS DRIVE Winter Garden, FL MLS# O6433944
  • Recently Listed with Virtual Tour
1 of 45
$419,999
3

Beds

2.1

Baths

1,636

Sq.Ft.

10648 WORDS DRIVE

Winter Garden, FL

View 14448 PLEACH STREET Winter Garden, FL MLS# O6433986
  • Recently Listed with Virtual Tour
1 of 11
$350,000
2

Beds

2.1

Baths

1,345

Sq.Ft.

14448 PLEACH STREET

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 16306 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6433563
  • Recently Listed with Virtual Tour
1 of 29
$415,000
3

Beds

2.1

Baths

1,792

Sq.Ft.

16306 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

View 16546 BARBOURS CREEK WAY Winter Garden, FL MLS# O6433682
  • New Construction with Virtual Tour
1 of 27
OPEN HOUSE: Sunday 8/23 12:00 PM - 6:00 PM
$414,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16546 BARBOURS CREEK WAY

Winter Garden, FL

View 16534 BARBOURS CREEK WAY Winter Garden, FL MLS# O6433686
  • Recently Listed with Virtual Tour
1 of 18
$464,990
3

Beds

2.1

Baths

1,817

Sq.Ft.

16534 BARBOURS CREEK WAY

Winter Garden, FL

View 15014 WINDFLOWER ALLEY Winter Garden, FL MLS# O6433433
  • Recently Listed with Virtual Tour
1 of 22
$424,990
3

Beds

2.1

Baths

1,536

Sq.Ft.

15014 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES

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

1,017

Estimated median home price

$612,000
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 - 100K2
$100K - 200K21
$200K - 300K86
$300K - 400K77
$400K - 500K152
$500K - 600K162
$600K - 700K114
$700K - 800K112
$800K - 900K107
$900K - 1M64
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family701
Townhouse146
Condo132
Commercial9
Rental180
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/22/2026)

Information deemed reliable but not guaranteed.

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 8/23/2026.