View 5755 CYPRESS HILL ROAD Winter Garden, FL MLS# O6404161
$455,000
3

Beds

2.1

Baths

1,797

Sq.Ft.

5755 CYPRESS HILL ROAD

Winter Garden, FL

View 14014 SCARLET ASTER ALLEY Winter Garden, FL MLS# O6418814
$455,000
3

Beds

3.0

Baths

1,808

Sq.Ft.

14014 SCARLET ASTER ALLEY

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 15038 WINDFLOWER ALLEY Winter Garden, FL MLS# O6434050
  • Recently Listed with Virtual Tour
1 of 29
OPEN HOUSE: Sunday 8/30 12:00 PM - 3:00 PM
$455,000
3

Beds

2.1

Baths

1,536

Sq.Ft.

15038 WINDFLOWER ALLEY

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 16558 BARBOURS CREEK WAY Winter Garden, FL MLS# O6420061
  • New Construction with Virtual Tour
1 of 67
$454,990
3

Beds

2.1

Baths

1,817

Sq.Ft.

16558 BARBOURS CREEK WAY

Winter Garden, FL

View 17736 PORTER ROAD Winter Garden, FL MLS# G5112009
  • New Construction with Virtual Tour
1 of 25
$451,542
3

Beds

3.0

Baths

1,715

Sq.Ft.

17736 PORTER ROAD

Winter Garden, FL

View 14501 Grove Resort Avenue Winter Garden, FL MLS# R11079278
$450,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 Grove Resort Avenue

Winter Garden, FL

View 217 W STORY ROAD Winter Garden, FL MLS# O6417750
$450,000
3

Beds

2.0

Baths

1,120

Sq.Ft.

217 W STORY ROAD

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 11102 HANLON TERRACE ALLEY Winter Garden, FL MLS# S5155891
  • Recently Listed with Virtual Tour
1 of 25
$450,000
3

Beds

2.1

Baths

1,868

Sq.Ft.

11102 HANLON TERRACE ALLEY

Winter Garden, FL

Courtesy of PRIMUS CRE GROUP
View 16435 HAMLIN HILLS ROAD Winter Garden, FL MLS# O6420316
$449,999
3

Beds

2.1

Baths

1,736

Sq.Ft.

16435 HAMLIN HILLS ROAD

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
View 10294 MERRYMEETING BAY DRIVE Winter Garden, FL MLS# O6407798
$449,900
3

Beds

2.0

Baths

1,689

Sq.Ft.

10294 MERRYMEETING BAY DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 9362 WOODCRANE DRIVE Winter Garden, FL MLS# O6417277
$449,300
3

Beds

2.1

Baths

2,058

Sq.Ft.

9362 WOODCRANE DRIVE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 14501 GROVE RESORT AVE 1622 Winter Garden, FL MLS# O6367905
$449,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVE 1622

Winter Garden, FL

View 12050 BRACCO STREET Winter Garden, FL MLS# O6398494
$449,000
3

Beds

2.1

Baths

1,770

Sq.Ft.

12050 BRACCO STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 16510 BARBOURS CREEK WAY Winter Garden, FL MLS# O6435580
  • Recently Listed with Virtual Tour
1 of 27
$447,500
3

Beds

2.1

Baths

1,567

Sq.Ft.

16510 BARBOURS CREEK WAY

Winter Garden, FL

View 11162 HANLON TERRACE ALLEY Winter Garden, FL MLS# S5124930
$445,000
3

Beds

2.1

Baths

1,881

Sq.Ft.

11162 HANLON TERRACE ALLEY

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 10660 WORDS DRIVE Winter Garden, FL MLS# O6429603
$445,000
4

Beds

2.1

Baths

1,992

Sq.Ft.

10660 WORDS DRIVE

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 6262 SUNNY TIME AVENUE Winter Garden, FL MLS# O6427189
  • New Construction with Virtual Tour
1 of 26
$443,190
3

Beds

2.1

Baths

1,683

Sq.Ft.

6262 SUNNY TIME AVENUE

Winter Garden, FL

View 5545 BOWMAN DRIVE Winter Garden, FL MLS# O6407484
  • Virtual Tour
1 of 29
OPEN HOUSE: Sunday 8/30 9:00 AM - 7:00 PM
$440,000
2

Beds

2.1

Baths

1,998

Sq.Ft.

5545 BOWMAN DRIVE

Winter Garden, FL

View 721 S WOODLAND STREET Winter Garden, FL MLS# O6419636
$440,000
2

Beds

1.0

Baths

1,034

Sq.Ft.

721 S WOODLAND STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 721 SUNBURST COVE LANE Winter Garden, FL MLS# O6430259
$440,000
4

Beds

2.0

Baths

1,878

Sq.Ft.

721 SUNBURST COVE LANE

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

1,029

Estimated median home price

$608,000
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 - 200K22
$200K - 300K89
$300K - 400K78
$400K - 500K153
$500K - 600K168
$600K - 700K112
$700K - 800K113
$800K - 900K112
$900K - 1M62
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family715
Townhouse145
Condo133
Commercial9
Rental188
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/29/2026)

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

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 8/30/2026.