View 15183 BRIDGEWATER CROSSINGS BOULEVARD Winter Garden, FL MLS# O6416462
  • Recently Listed with Virtual Tour
1 of 47
$520,000
3

Beds

2.1

Baths

1,998

Sq.Ft.

15183 BRIDGEWATER CROSSINGS BOULEVARD

Winter Garden, FL

View 15524 HONEYBELL DRIVE Winter Garden, FL MLS# O6416374
$419,000
4

Beds

3.0

Baths

1,902

Sq.Ft.

15524 HONEYBELL DRIVE

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 1726 Winter Garden, FL MLS# S5151998
$174,999
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1726

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 142 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# O6414551
$297,900
3

Beds

2.0

Baths

1,453

Sq.Ft.

142 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

View 9362 WOODCRANE DRIVE Winter Garden, FL MLS# O6417277
$459,300
3

Beds

2.1

Baths

2,058

Sq.Ft.

9362 WOODCRANE DRIVE

Winter Garden, FL

View 1645 E SPRING RIDGE CIRCLE Winter Garden, FL MLS# O6416732
$439,000
3

Beds

2.0

Baths

1,219

Sq.Ft.

1645 E SPRING RIDGE CIRCLE

Winter Garden, FL

Courtesy of PREFERRED RE BROKERS III
View 5754 SURPRISE LILY DRIVE Winter Garden, FL MLS# S5151845
$499,000
4

Beds

2.1

Baths

2,128

Sq.Ft.

5754 SURPRISE LILY DRIVE

Winter Garden, FL

View 13303 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5113612
  • New Construction with Virtual Tour
1 of 25
$424,990
3

Beds

2.1

Baths

1,715

Sq.Ft.

13303 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1343 CASTLEPORT ROAD Winter Garden, FL MLS# O6414756
$525,000
3

Beds

2.0

Baths

2,170

Sq.Ft.

1343 CASTLEPORT ROAD

Winter Garden, FL

View 110 WINDTREE LANE 202 Winter Garden, FL MLS# O6414527
$209,900
2

Beds

2.0

Baths

918

Sq.Ft.

110 WINDTREE LANE 202

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 12830 SUNSET WALK DRIVE Winter Garden, FL MLS# O6415339
  • New Construction with Virtual Tour
1 of 7
$471,000
3

Beds

2.1

Baths

1,857

Sq.Ft.

12830 SUNSET WALK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 1300 EASTERN PECAN PLACE 102 Winter Garden, FL MLS# S5151632
$275,000
2

Beds

2.0

Baths

1,152

Sq.Ft.

1300 EASTERN PECAN PLACE 102

Winter Garden, FL

Courtesy of KELLER WILLIAMS LEGACY REALTY
View 1008 STUCKI TERRACE Winter Garden, FL MLS# O6414791
$215,000
2

Beds

2.0

Baths

814

Sq.Ft.

1008 STUCKI TERRACE

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 3425 Winter Garden, FL MLS# O6414956
  • Adult Community with Virtual Tour
1 of 21
$480,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3425

Winter Garden, FL

Courtesy of MIAMI LIFE REALTY LLC
View 2227 OAKINGTON STREET Winter Garden, FL MLS# O6414707
$489,990
4

Beds

2.0

Baths

1,867

Sq.Ft.

2227 OAKINGTON STREET

Winter Garden, FL

Courtesy of REALTY ONE GROUP EVOLUTION
View 411 MILLWOOD PLACE Winter Garden, FL MLS# TB8518055
$459,000
3

Beds

2.0

Baths

1,696

Sq.Ft.

411 MILLWOOD PLACE

Winter Garden, FL

View 13011 TRANQUIL WATER ALLEY Winter Garden, FL MLS# O6414240
  • New Construction with Virtual Tour
1 of 33
$534,990
3

Beds

2.1

Baths

2,078

Sq.Ft.

13011 TRANQUIL WATER ALLEY

Winter Garden, FL

Courtesy of LPT REALTY LLC
View 1701 E BAY STREET Winter Garden, FL MLS# O6413973
$295,000
2

Beds

2.0

Baths

825

Sq.Ft.

1701 E BAY STREET

Winter Garden, FL

View 14903 DRIFTWATER DRIVE Winter Garden, FL MLS# S5151359
$380,000
3

Beds

2.1

Baths

1,745

Sq.Ft.

14903 DRIFTWATER DRIVE

Winter Garden, FL

View 12792 SUNSET WALK DRIVE Winter Garden, FL MLS# O6414001
$527,000
4

Beds

3.0

Baths

1,930

Sq.Ft.

12792 SUNSET WALK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC

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

937

Estimated median home price

$599,990
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 - 300K89
$300K - 400K64
$400K - 500K134
$500K - 600K163
$600K - 700K103
$700K - 800K94
$800K - 900K87
$900K - 1M63
$1M - Max118

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family638
Townhouse130
Condo135
Commercial11
Rental198
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/12/2026)

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

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties 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 7/12/2026.