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 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

The time to sell is now! THE TIME TO SELL IS NOW!
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 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 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 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 14501 GROVE RESORT AVENUE 2342 Winter Garden, FL MLS# O6432384
  • Recently Listed with Virtual Tour
1 of 55
$340,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 2342

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
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
View 1327 PRIORY CIRCLE 1327 Winter Garden, FL MLS# O6434028
  • Recently Listed with Virtual Tour
1 of 26
$369,500
3

Beds

2.1

Baths

1,650

Sq.Ft.

1327 PRIORY CIRCLE 1327

Winter Garden, FL

Courtesy of INNOVATIVE REALTY, LLC
View 14501 GROVE RESORT AVE Winter Garden, FL MLS# O6433198
  • Recently Listed with Virtual Tour
1 of 11
$335,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVE

Winter Garden, FL

Courtesy of MRI REALTY GROUP
View 8013 BASILICA LANE Winter Garden, FL MLS# O6432456
  • Recently Listed with Virtual Tour
1 of 32
$410,000
3

Beds

2.1

Baths

1,860

Sq.Ft.

8013 BASILICA LANE

Winter Garden, FL

View 17723 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6432610
  • Recently Listed with Virtual Tour
1 of 38
$399,999
3

Beds

2.1

Baths

1,584

Sq.Ft.

17723 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of Lake Mary - WEICHERT, REALTORS® - Hallmark 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

1,014

Estimated median home price

$613,495
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 - 300K86
$300K - 400K78
$400K - 500K151
$500K - 600K160
$600K - 700K114
$700K - 800K112
$800K - 900K107
$900K - 1M64
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family698
Townhouse146
Condo133
Commercial9
Rental178
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/23/2026)

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.