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 14645 TULLAMORE LOOP Winter Garden, FL MLS# O6409068
$455,000
3

Beds

2.0

Baths

1,703

Sq.Ft.

14645 TULLAMORE LOOP

Winter Garden, FL

Courtesy of LPT REALTY, LLC
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

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 14536 GOLDEN HARBOR LANE Winter Garden, FL MLS# O6320739
$450,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

14536 GOLDEN HARBOR LANE

Winter Garden, FL

Courtesy of PIXEL REALTY,PLLC
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 11072 SILVER SURFER ALLEY Winter Garden, FL MLS# O6406656
$450,000
3

Beds

2.1

Baths

1,770

Sq.Ft.

11072 SILVER SURFER ALLEY

Winter Garden, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 6131 ELFIN HERB WAY Winter Garden, FL MLS# O6414015
$450,000
3

Beds

2.1

Baths

1,714

Sq.Ft.

6131 ELFIN HERB WAY

Winter Garden, FL

View 1610 BEULAH ROAD Winter Garden, FL MLS# O6418153
  • Recently Listed with Virtual Tour
1 of 43
$450,000
4

Beds

2.0

Baths

2,210

Sq.Ft.

1610 BEULAH ROAD

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 217 W STORY ROAD Winter Garden, FL MLS# O6417750
  • Recently Listed
1 of 27
$450,000
3

Beds

2.0

Baths

1,120

Sq.Ft.

217 W STORY ROAD

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 721 S WOODLAND STREET Winter Garden, FL MLS# O6419636
  • Recently Listed with Virtual Tour
1 of 24
$450,000
2

Beds

1.0

Baths

1,034

Sq.Ft.

721 S WOODLAND STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 8150 RED STOPPER LANE Winter Garden, FL MLS# O6416867
  • Recently Listed with Virtual Tour
1 of 47
$450,000
3

Beds

2.1

Baths

1,738

Sq.Ft.

8150 RED STOPPER LANE

Winter Garden, FL

View 13299 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5112134
  • New Construction with Virtual Tour
1 of 26
$449,990
3

Beds

2.1

Baths

1,729

Sq.Ft.

13299 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
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

Courtesy of MBI REALTY LLC
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 8170 BLUEJACK OAK DRIVE Winter Garden, FL MLS# O6399484
$445,000
3

Beds

2.1

Baths

1,853

Sq.Ft.

8170 BLUEJACK OAK DRIVE

Winter Garden, FL

View 12003 HOLYSTONE STREET Winter Garden, FL MLS# L4961121
$445,000
3

Beds

2.1

Baths

1,814

Sq.Ft.

12003 HOLYSTONE STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY SMART
View 12103 EASTMOOR DRIVE Winter Garden, FL MLS# O6409071
  • Virtual Tour
1 of 24
OPEN HOUSE: Saturday 7/11 12:00 PM - 3:00 PM
$445,000
3

Beds

2.0

Baths

1,604

Sq.Ft.

12103 EASTMOOR DRIVE

Winter Garden, FL

View 16353 LAKELET ALLEY Winter Garden, FL MLS# O6316011
  • New Construction with Virtual Tour
1 of 32
$444,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16353 LAKELET ALLEY

Winter Garden, FL

View 8156 WOOD SAGE DRIVE Winter Garden, FL MLS# V4947783
  • Adult Community with Virtual Tour
1 of 42
OPEN HOUSE: Sunday 7/12 12:00 PM - 2:00 PM
$444,000
3

Beds

2.1

Baths

1,853

Sq.Ft.

8156 WOOD SAGE DRIVE

Winter Garden, FL

View 15907 MARINA BAY DRIVE Winter Garden, FL MLS# O6398406
$443,500
3

Beds

2.1

Baths

1,818

Sq.Ft.

15907 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of SIMPSON 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

1,058

Estimated median home price

$615,000
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 - 300K96
$300K - 400K71
$400K - 500K142
$500K - 600K186
$600K - 700K119
$700K - 800K115
$800K - 900K99
$900K - 1M70
$1M - Max137

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family746
Townhouse133
Condo143
Commercial11
Rental198
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/7/2026)

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 7/8/2026.