View 1366 PRIORY CIRCLE 8 Winter Garden, FL MLS# O6387059
  • Recently Listed with Virtual Tour
1 of 25
$2,400
3

Beds

2.1

Baths

1,633

Sq.Ft.

1366 PRIORY CIRCLE 8

Winter Garden, FL

Courtesy of 1 ELEVEN REALTY
View 15621 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6386720
  • Recently Listed with Virtual Tour
1 of 21
$2,700
3

Beds

2.1

Baths

1,636

Sq.Ft.

15621 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of JC FLORIDA REALTY LLC
View 1009 WESTSIDE DRIVE Winter Garden, FL MLS# O6386529
  • Recently Listed with Virtual Tour
1 of 17
$2,100
3

Beds

2.0

Baths

1,180

Sq.Ft.

1009 WESTSIDE DRIVE

Winter Garden, FL

Courtesy of INDEPENDENCE REALTY GROUP LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 6149 WATERSIDE ISLAND LANE Winter Garden, FL MLS# O6383500
  • Recently Listed with Virtual Tour
1 of 28
$3,300
4

Beds

3.1

Baths

2,725

Sq.Ft.

6149 WATERSIDE ISLAND LANE

Winter Garden, FL

Courtesy of TOPSKY REALTY INC
View 15116 WINDFLOWER ALY Winter Garden, FL MLS# O6386936
  • Recently Listed with Virtual Tour
1 of 20
$2,450
3

Beds

2.1

Baths

1,536

Sq.Ft.

15116 WINDFLOWER ALY

Winter Garden, FL

Courtesy of CELEBRITY GLOBAL REALTY LLC
View 17789 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6385892
  • Recently Listed with Virtual Tour
1 of 27
$2,750
3

Beds

2.1

Baths

1,668

Sq.Ft.

17789 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 911 COLIE ALLEY Winter Garden, FL MLS# O6379713
  • Recently Listed with Virtual Tour
1 of 23
$3,045
3

Beds

2.1

Baths

1,632

Sq.Ft.

911 COLIE ALLEY

Winter Garden, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 216 JEAN STREET Winter Garden, FL MLS# O6386307
  • Recently Listed with Virtual Tour
1 of 19
$2,500
3

Beds

2.1

Baths

1,026

Sq.Ft.

216 JEAN STREET

Winter Garden, FL

Courtesy of NEXTHOME NEIGHBORHOOD REALTY
View 304 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# O6383493
  • Recently Listed with Virtual Tour
1 of 46
$1,990
2

Beds

2.0

Baths

1,264

Sq.Ft.

304 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

Courtesy of AFT PROPERTY LLC
View 14996 WINDFLOWER ALLEY Winter Garden, FL MLS# O6386796
  • Recently Listed with Virtual Tour
1 of 26
$2,450
3

Beds

2.1

Baths

1,536

Sq.Ft.

14996 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15146 WINDFLOWER ALLEY Winter Garden, FL MLS# O6386816
  • Recently Listed with Virtual Tour
1 of 32
$2,450
3

Beds

2.1

Baths

1,536

Sq.Ft.

15146 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 12887 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# S5144652
  • Recently Listed with Virtual Tour
1 of 42
$3,600
5

Beds

4.0

Baths

2,700

Sq.Ft.

12887 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 3265 HIDDEN LAKE DRIVE Winter Garden, FL MLS# O6386112
  • Recently Listed with Virtual Tour
1 of 60
$6,995
5

Beds

4.0

Baths

3,694

Sq.Ft.

3265 HIDDEN LAKE DRIVE

Winter Garden, FL

Courtesy of BHHS FLORIDA REALTY
View 15887 GRAFTON WAY Winter Garden, FL MLS# O6385094
  • Recently Listed with Virtual Tour
1 of 18
$2,600
3

Beds

2.1

Baths

1,567

Sq.Ft.

15887 GRAFTON WAY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 1301 EASTERN PECAN PLACE 203 Winter Garden, FL MLS# O6385479
  • Recently Listed with Virtual Tour
1 of 49
$1,650
1

Beds

1.0

Baths

942

Sq.Ft.

1301 EASTERN PECAN PLACE 203

Winter Garden, FL

Courtesy of CLAIRE SCHWARTZ & ASSOCIATES
View 1323 DANIELS COVE DRIVE Winter Garden, FL MLS# O6385141
  • Recently Listed with Virtual Tour
1 of 27
$2,400
3

Beds

2.0

Baths

985

Sq.Ft.

1323 DANIELS COVE DRIVE

Winter Garden, FL

Courtesy of STOCKWORTH REALTY GROUP LLC
View 11422 GREAT ROCK STREET Winter Garden, FL MLS# S5144550
  • Recently Listed with Virtual Tour
1 of 24
$3,000
4

Beds

3.1

Baths

2,502

Sq.Ft.

11422 GREAT ROCK STREET

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 12736 BRODLOVE LANE Winter Garden, FL MLS# O6384962
  • Recently Listed with Virtual Tour
1 of 16
$3,400
4

Beds

3.1

Baths

2,800

Sq.Ft.

12736 BRODLOVE LANE

Winter Garden, FL

Courtesy of RIO HOMES AND INVESTMENTS LLC
View 16258 MERRY ALLEY Winter Garden, FL MLS# O6383652
  • Recently Listed with Virtual Tour
1 of 24
$2,650
3

Beds

2.1

Baths

1,683

Sq.Ft.

16258 MERRY ALLEY

Winter Garden, FL

Courtesy of POINTON REALTY INC
View 16264 MERRY ALLEY Winter Garden, FL MLS# O6385278
  • New Construction with Virtual Tour
1 of 19
$2,620
3

Beds

2.1

Baths

1,683

Sq.Ft.

16264 MERRY ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE

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

898

Estimated median home price

$594,995
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 - 200K13
$200K - 300K87
$300K - 400K76
$400K - 500K150
$500K - 600K136
$600K - 700K108
$700K - 800K90
$800K - 900K66
$900K - 1M63
$1M - Max102

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family604
Townhouse128
Condo126
Commercial9
Rental223
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 3/3/2026)

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 3/3/2026.