View 2621 SHIREHALL LANE Winter Garden, FL MLS# O6386585
$475,000
3

Beds

2.0

Baths

1,960

Sq.Ft.

2621 SHIREHALL LANE

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 15182 SUNRISE GROVE COURT Winter Garden, FL MLS# O6382211
$394,900
3

Beds

2.1

Baths

1,844

Sq.Ft.

15182 SUNRISE GROVE COURT

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 838 BETHUNE AVENUE Winter Garden, FL MLS# O6388596
$275,000
3

Beds

2.0

Baths

985

Sq.Ft.

838 BETHUNE AVENUE

Winter Garden, FL

Courtesy of LIVE MVRK LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 7007 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6388545
$465,000
3

Beds

2.1

Baths

1,845

Sq.Ft.

7007 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 16856 HYPATIA ALLEY Winter Garden, FL MLS# O6387941
$459,999
3

Beds

2.0

Baths

1,705

Sq.Ft.

16856 HYPATIA ALLEY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 13350 W COLONIAL DRIVE C1 Winter Garden, FL MLS# V4947708
$399,000
1,152

Sq.Ft.

13350 W COLONIAL DRIVE C1

Winter Garden, FL

Courtesy of LPT REALTY LLC
View 1710 E BAY STREET Winter Garden, FL MLS# O6376343
  • Virtual Tour
1 of 43
$249,990
3

Beds

2.0

Baths

972

Sq.Ft.

1710 E BAY STREET

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 14095 TITLE WAY Winter Garden, FL MLS# O6382795
  • Virtual Tour
1 of 38
$440,000
3

Beds

2.1

Baths

1,628

Sq.Ft.

14095 TITLE WAY

Winter Garden, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 225 SOUTHERN PECAN CIRCLE 208 Winter Garden, FL MLS# O6383422
$289,900
2

Beds

2.0

Baths

1,264

Sq.Ft.

225 SOUTHERN PECAN CIRCLE 208

Winter Garden, FL

Courtesy of JOHN SILVA REALTY & ASSOCIATES
View 15140 SUNRISE GROVE COURT Winter Garden, FL MLS# O6388259
$390,987
3

Beds

2.1

Baths

2,012

Sq.Ft.

15140 SUNRISE GROVE COURT

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 14501 GROVE RESORT AVENUE 3109 Winter Garden, FL MLS# O6386655
$314,900
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 3109

Winter Garden, FL

Courtesy of MBI REALTY LLC
View 5706 CYPRESS HILL ROAD Winter Garden, FL MLS# O6386620
$460,000
3

Beds

2.1

Baths

1,712

Sq.Ft.

5706 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16563 BARBOURS CREEK WAY Winter Garden, FL MLS# O6386283
  • New Construction with Virtual Tour
1 of 14
$414,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16563 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 18167 CIDER MILL LANE Winter Garden, FL MLS# O6386278
  • New Construction with Virtual Tour
1 of 15
$469,990
3

Beds

2.1

Baths

1,817

Sq.Ft.

18167 CIDER MILL LANE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 13291 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5108893
  • New Construction with Virtual Tour
1 of 53
$428,405
3

Beds

2.1

Baths

1,644

Sq.Ft.

13291 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8113 RED STOPPER LANE Winter Garden, FL MLS# O6386525
  • Virtual Tour
1 of 62
OPEN HOUSE: Sunday 5/3 1:00 PM - 3:00 PM
$444,000
3

Beds

2.1

Baths

1,725

Sq.Ft.

8113 RED STOPPER LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 14447 PRUNNINGWOOD PLACE Winter Garden, FL MLS# O6385194
$340,000
2

Beds

2.1

Baths

1,250

Sq.Ft.

14447 PRUNNINGWOOD PLACE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 87 WINDTREE LANE K Winter Garden, FL MLS# G5108773
  • Virtual Tour
1 of 39
$205,000
2

Beds

2.0

Baths

918

Sq.Ft.

87 WINDTREE LANE K

Winter Garden, FL

Courtesy of BONJORN REAL ESTATE
View 15098 WINDFLOWER ALLEY Winter Garden, FL MLS# O6386823
$365,000
2

Beds

2.1

Baths

1,276

Sq.Ft.

15098 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 1401 N FULLERS CROSS ROAD Winter Garden, FL MLS# O6385497
$395,000
Studio

Beds

0.0

Baths

1401 N FULLERS CROSS ROAD

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES

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

997

Estimated median home price

$606,440
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

Price Count
$0 - 100K 1
$100K - 200K 18
$200K - 300K 101
$300K - 400K 81
$400K - 500K 140
$500K - 600K 155
$600K - 700K 128
$700K - 800K 111
$800K - 900K 87
$900K - 1M 68
$1M - Max 107

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 688
Townhouse 130
Condo 140
Commercial 11
Rental 219
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 5/1/2026)

Information deemed reliable but not guaranteed.

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.

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

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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.

Data is updated as of 5/1/2026.

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 5/1/2026.