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 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 430 SOUTHERN PECAN CIRCLE 203 Winter Garden, FL MLS# TB8525187
$1,600
1

Beds

1.0

Baths

942

Sq.Ft.

430 SOUTHERN PECAN CIRCLE 203

Winter Garden, FL

View 14978 LEBEAU LOOP Winter Garden, FL MLS# S5150861
$1,690
1

Beds

1.0

Baths

700

Sq.Ft.

14978 LEBEAU LOOP

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
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
$1,700
2

Beds

2.0

Baths

918

Sq.Ft.

165 WINDTREE LANE U

Winter Garden, FL

Courtesy of ZEAL REALTY
View 1317 FETTLER WAY Winter Garden, FL MLS# S5153684
  • Recently Listed with Virtual Tour
1 of 11
$1,700
3

Beds

2.0

Baths

1,076

Sq.Ft.

1317 FETTLER WAY

Winter Garden, FL

View 417 SOUTHERN PECAN CIRCLE 207 Winter Garden, FL MLS# S5151779
$1,750
1

Beds

1.0

Baths

942

Sq.Ft.

417 SOUTHERN PECAN CIRCLE 207

Winter Garden, FL

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 1257 WINTER GREEN WAY Winter Garden, FL MLS# O6419882
$1,850
2

Beds

1.1

Baths

1,144

Sq.Ft.

1257 WINTER GREEN WAY

Winter Garden, FL

View 200 SOUTHERN PECAN CIRCLE 203 Winter Garden, FL MLS# S5152842
  • Recently Listed with Virtual Tour
1 of 22
$1,890
2

Beds

2.0

Baths

1,276

Sq.Ft.

200 SOUTHERN PECAN CIRCLE 203

Winter Garden, FL

View 53 WINDTREE LANE 102 Winter Garden, FL MLS# O6425367
  • Recently Listed with Virtual Tour
1 of 30
$1,895
2

Beds

2.0

Baths

918

Sq.Ft.

53 WINDTREE LANE 102

Winter Garden, FL

View 1432 BROKEN OAK DRIVE 31A Winter Garden, FL MLS# G5115164
  • Recently Listed with Virtual Tour
1 of 10
$1,900
2

Beds

2.0

Baths

1,216

Sq.Ft.

1432 BROKEN OAK DRIVE 31A

Winter Garden, FL

View 15000 STRATUS LOOP A2 Winter Garden, FL MLS# O6308743
$1,935
1

Beds

1.0

Baths

873

Sq.Ft.

15000 STRATUS LOOP A2

Winter Garden, FL

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 1000 DOLPHIN DRIVE Winter Garden, FL MLS# S5149912
$2,000
3

Beds

2.0

Baths

984

Sq.Ft.

1000 DOLPHIN DRIVE

Winter Garden, FL

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

942

Estimated median home price

$608,645
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 - 200K21
$200K - 300K91
$300K - 400K65
$400K - 500K135
$500K - 600K155
$600K - 700K102
$700K - 800K101
$800K - 900K89
$900K - 1M62
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family642
Townhouse132
Condo135
Commercial11
Rental203
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/16/2026)

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 7/17/2026.