View 216 JEAN STREET Winter Garden, FL MLS# O6386307
$2,500
3

Beds

2.1

Baths

1,026

Sq.Ft.

216 JEAN STREET

Winter Garden, FL

Courtesy of NEXTHOME NEIGHBORHOOD REALTY
View 15146 WINDFLOWER ALLEY Winter Garden, FL MLS# O6386816
$2,450
3

Beds

2.1

Baths

1,536

Sq.Ft.

15146 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 1301 EASTERN PECAN PLACE 203 Winter Garden, FL MLS# O6385479
$1,550
1

Beds

1.0

Baths

942

Sq.Ft.

1301 EASTERN PECAN PLACE 203

Winter Garden, FL

Courtesy of CLAIRE SCHWARTZ & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 16258 MERRY ALLEY Winter Garden, FL MLS# O6383652
  • New Construction with Virtual Tour
1 of 24
$2,550
3

Beds

2.1

Baths

1,683

Sq.Ft.

16258 MERRY ALLEY

Winter Garden, FL

Courtesy of POINTON REALTY INC
View 13362 DANIELS LANDING CIRCLE 13362 Winter Garden, FL MLS# O6383822
$2,200
2

Beds

2.1

Baths

1,293

Sq.Ft.

13362 DANIELS LANDING CIRCLE 13362

Winter Garden, FL

Courtesy of LAIN REALTY & PROPERTY MANAGEMENT
View 12144 STONELEIGH ALLEY Winter Garden, FL MLS# O6384252
$2,600
3

Beds

2.0

Baths

1,588

Sq.Ft.

12144 STONELEIGH ALLEY

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 336 E PLANT STREET Winter Garden, FL MLS# O6381842
$784
1,232

Sq.Ft.

336 E PLANT STREET

Winter Garden, FL

Courtesy of WINTER GARDEN REAL ESTATE
View 1519 PRIORY CIRCLE Winter Garden, FL MLS# O6382465
$2,800
3

Beds

2.1

Baths

1,956

Sq.Ft.

1519 PRIORY CIRCLE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 10284 ATWATER BAY DRIVE Winter Garden, FL MLS# O6382148
$3,250
4

Beds

3.0

Baths

2,300

Sq.Ft.

10284 ATWATER BAY DRIVE

Winter Garden, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View 7000 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6381796
$2,900
4

Beds

3.1

Baths

1,914

Sq.Ft.

7000 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 15704 MARINA BAY DRIVE Winter Garden, FL MLS# O6380878
$11,500
5

Beds

5.1

Baths

5,005

Sq.Ft.

15704 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of DOUBLE M GROUP COMPANY
View 13344 HARBOR SHORE LANE Winter Garden, FL MLS# S5143640
$2,200
2

Beds

2.1

Baths

1,234

Sq.Ft.

13344 HARBOR SHORE LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15481 BAY BRIDGE STREET Winter Garden, FL MLS# O6380391
  • New Construction with Virtual Tour
1 of 30
$2,850
3

Beds

2.1

Baths

1,670

Sq.Ft.

15481 BAY BRIDGE STREET

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 15010 SUMMER HARVEST STREET Winter Garden, FL MLS# O6371081
  • New Construction with Virtual Tour
1 of 25
$3,400
4

Beds

3.1

Baths

2,322

Sq.Ft.

15010 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 7556 JOHN HANCOCK DRIVE Winter Garden, FL MLS# O6380128
  • New Construction with Virtual Tour
1 of 95
$18,000
5

Beds

6.1

Baths

5,108

Sq.Ft.

7556 JOHN HANCOCK DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 17609 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6380304
  • New Construction with Virtual Tour
1 of 16
$3,050
3

Beds

2.1

Baths

2,103

Sq.Ft.

17609 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of THE PROPERTY STOP LLC
View 8019 JEREMY JOSEPH ALLEY 8019 Winter Garden, FL MLS# O6379718
  • New Construction with Virtual Tour
1 of 23
$2,495
3

Beds

2.1

Baths

1,691

Sq.Ft.

8019 JEREMY JOSEPH ALLEY 8019

Winter Garden, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View 8125 GRAYCLIFF AVENUE Winter Garden, FL MLS# O6379515
$2,600
3

Beds

2.0

Baths

1,676

Sq.Ft.

8125 GRAYCLIFF AVENUE

Winter Garden, FL

Courtesy of SELECTA REALTY LLC
View 12012 HOLYSTONE STREET Winter Garden, FL MLS# O6379118
$2,495
3

Beds

2.1

Baths

1,451

Sq.Ft.

12012 HOLYSTONE STREET

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
View Address not provided Winter Garden, FL MLS# O6378945
$1,995
2

Beds

2.0

Baths

1,152

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of MARTI PURDY PROPERTIES INC

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

1,020

Estimated median home price

$612,250
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 - 200K20
$200K - 300K101
$300K - 400K78
$400K - 500K142
$500K - 600K155
$600K - 700K132
$700K - 800K117
$800K - 900K85
$900K - 1M79
$1M - Max110

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family696
Townhouse140
Condo140
Commercial11
Rental216
Lots and Land30
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/12/2026)

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 5/13/2026.