View 186 S MAIN STREET Winter Garden, FL MLS# O6359871
  • New Construction with Virtual Tour
1 of 7
$0
16,000

Sq.Ft.

186 S MAIN STREET

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 981 VINELAND ROAD Winter Garden, FL MLS# O6364366
  • New Construction with Virtual Tour
1 of 6
$0
8,700

Sq.Ft.

981 VINELAND ROAD

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 15267 HONEYBELL DRIVE Winter Garden, FL MLS# S5146372
$675
1

Beds

1.0

Baths

1,000

Sq.Ft.

15267 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of VESTI LLC
The time to sell is now! THE TIME TO SELL IS NOW!
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 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
View 314 DOUGLAS WAY 900 Winter Garden, FL MLS# O6393613
$1,570
2

Beds

2.0

Baths

930

Sq.Ft.

314 DOUGLAS WAY 900

Winter Garden, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 12506 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# S5148369
$1,600
1

Beds

1.0

Baths

2,900

Sq.Ft.

12506 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 80 WINDTREE LANE 203 Winter Garden, FL MLS# O6394220
$1,650
2

Beds

2.0

Baths

918

Sq.Ft.

80 WINDTREE LANE 203

Winter Garden, FL

Courtesy of ROMAN REALTY GROUP, LLC
View 508 VARSITY STREET Winter Garden, FL MLS# O6401722
$1,695
2

Beds

1.0

Baths

780

Sq.Ft.

508 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 165 WINDTREE LANE U Winter Garden, FL MLS# O6392506
$1,750
2

Beds

2.0

Baths

918

Sq.Ft.

165 WINDTREE LANE U

Winter Garden, FL

Courtesy of ZEAL REALTY
View 1066 DOLPHIN DRIVE Winter Garden, FL MLS# O6407929
  • Recently Listed with Virtual Tour
1 of 25
$1,750
3

Beds

2.0

Baths

1,440

Sq.Ft.

1066 DOLPHIN DRIVE

Winter Garden, FL

Courtesy of BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P
View 233 SOUTHERN PECAN CIRCLE 101 Winter Garden, FL MLS# S5142016
$1,795
2

Beds

1.0

Baths

966

Sq.Ft.

233 SOUTHERN PECAN CIRCLE 101

Winter Garden, FL

Courtesy of HOMESMART
View 7121 BLUE INDIGO CRESCENT Winter Garden, FL MLS# O6357690
$1,800
Studio

Beds

1.0

Baths

750

Sq.Ft.

7121 BLUE INDIGO CRESCENT

Winter Garden, FL

Courtesy of THE FLORIDA LOUNGE REALTY LLC
View 15000 STRATUS LOOP A2 Winter Garden, FL MLS# O6308729
$1,851
1

Beds

1.0

Baths

873

Sq.Ft.

15000 STRATUS LOOP A2

Winter Garden, FL

Courtesy of THE APARTMENT BROTHERS 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
View 417 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# O6403943
$1,995
2

Beds

2.0

Baths

1,264

Sq.Ft.

417 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

Courtesy of AFT PROPERTY LLC
View 430 SOUTHERN PECAN CIRCLE 101 Winter Garden, FL MLS# O6409326
  • Recently Listed with Virtual Tour
1 of 48
$1,995
2

Beds

2.0

Baths

1,152

Sq.Ft.

430 SOUTHERN PECAN CIRCLE 101

Winter Garden, FL

Courtesy of CANI PROPERTY MANAGEMENT
View 731 KLONDIKE STREET Winter Garden, FL MLS# TB8509410
  • Recently Listed with Virtual Tour
1 of 10
$2,000
3

Beds

1.0

Baths

958

Sq.Ft.

731 KLONDIKE STREET

Winter Garden, FL

Courtesy of ELITE KY HOMES, LLC
View 1009 WESTSIDE DRIVE Winter Garden, FL MLS# O6386529
$2,050
3

Beds

2.0

Baths

1,180

Sq.Ft.

1009 WESTSIDE DRIVE

Winter Garden, FL

Courtesy of INDEPENDENCE REALTY GROUP LLC
View 216 DEEPCOVE ROAD Winter Garden, FL MLS# O6399926
$2,100
2

Beds

2.1

Baths

1,236

Sq.Ft.

216 DEEPCOVE ROAD

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY

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

1,041

Estimated median home price

$609,900
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 - 200K22
$200K - 300K96
$300K - 400K83
$400K - 500K142
$500K - 600K168
$600K - 700K124
$700K - 800K119
$800K - 900K87
$900K - 1M73
$1M - Max125

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family715
Townhouse141
Condo143
Commercial10
Rental214
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/26/2026)

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 5/26/2026.