View 1433 PRIORY CIRCLE Winter Garden, FL MLS# O6364550
$385,000
3

Beds

2.1

Baths

1,840

Sq.Ft.

1433 PRIORY CIRCLE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 18219 OLIVER TWIST WAY Winter Garden, FL MLS# O6365155
$635,000
4

Beds

2.1

Baths

2,683

Sq.Ft.

18219 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of U S GLORY REALTY
View 16140 HARBOR MIST ALLEY Winter Garden, FL MLS# O6365057
$587,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

16140 HARBOR MIST ALLEY

Winter Garden, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15399 GILLIGAN COURT Winter Garden, FL MLS# O6365269
$699,000
4

Beds

3.1

Baths

2,758

Sq.Ft.

15399 GILLIGAN COURT

Winter Garden, FL

Courtesy of FCG REALTY
View 6152 MERIWETHER CRESCENT Winter Garden, FL MLS# O6365054
$814,900
5

Beds

3.1

Baths

3,367

Sq.Ft.

6152 MERIWETHER CRESCENT

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 17526 NORTHLAKE GROVE DRIVE Winter Garden, FL MLS# TB8454079
  • New Construction with Virtual Tour
1 of 40
$479,990
3

Beds

2.1

Baths

1,675

Sq.Ft.

17526 NORTHLAKE GROVE DRIVE

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 14931 LEBEAU LOOP Winter Garden, FL MLS# O6364989
$849,000
4

Beds

3.1

Baths

2,832

Sq.Ft.

14931 LEBEAU LOOP

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 13282 SERENE GLADE ROAD Winter Garden, FL MLS# G5105151
  • New Construction with Virtual Tour
1 of 53
$456,496
3

Beds

2.1

Baths

1,644

Sq.Ft.

13282 SERENE GLADE ROAD

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13270 SERENE GLADE ROAD Winter Garden, FL MLS# G5105152
  • New Construction with Virtual Tour
1 of 54
$456,940
3

Beds

2.1

Baths

1,644

Sq.Ft.

13270 SERENE GLADE ROAD

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13374 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105157
  • New Construction with Virtual Tour
1 of 28
$814,990
5

Beds

4.0

Baths

3,076

Sq.Ft.

13374 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15099 TEA TREE DRIVE Winter Garden, FL MLS# G5105171
$908,676
4

Beds

3.1

Baths

2,688

Sq.Ft.

15099 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6357 WILD PERSIMMON WAY Winter Garden, FL MLS# G5105172
$730,184
3

Beds

3.1

Baths

2,515

Sq.Ft.

6357 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13562 PEARL BEACH STREET Winter Garden, FL MLS# O6362827
  • Adult Community with Virtual Tour
1 of 40
$435,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

13562 PEARL BEACH STREET

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View Address not provided Winter Garden, FL MLS# TB8453450
  • New Construction with Virtual Tour
1 of 30
$524,990
3

Beds

3.1

Baths

2,072

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 15036 CHAPTER WAY Winter Garden, FL MLS# O6364954
$408,000
3

Beds

2.1

Baths

1,717

Sq.Ft.

15036 CHAPTER WAY

Winter Garden, FL

Courtesy of RC GROUP REALTY LLC
View 13848 PEACH ORCHARD WAY Winter Garden, FL MLS# O6365304
$800,000
5

Beds

4.0

Baths

3,598

Sq.Ft.

13848 PEACH ORCHARD WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View Address not provided Winter Garden, FL MLS# O6364817
$299,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of WELCOME HOME REALTY GROUP LLC
View 15216 CHAPTER WAY Winter Garden, FL MLS# S5139219
$515,000
4

Beds

3.0

Baths

2,042

Sq.Ft.

15216 CHAPTER WAY

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 14012 PEACH ORCHARD WAY Winter Garden, FL MLS# O6364564
$595,000
4

Beds

2.0

Baths

2,516

Sq.Ft.

14012 PEACH ORCHARD WAY

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 13398 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105139
  • New Construction with Virtual Tour
1 of 28
$723,990
4

Beds

2.1

Baths

2,235

Sq.Ft.

13398 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC

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

767

Estimated median home price

$587,000
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 - 100K7
$100K - 200K8
$200K - 300K64
$300K - 400K82
$400K - 500K131
$500K - 600K121
$600K - 700K85
$700K - 800K67
$800K - 900K61
$900K - 1M49
$1M - Max92

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family496
Townhouse117
Condo110
Commercial10
Rental223
Lots and Land30
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/2/2026)

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 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.

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 1/3/2026.

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 1/3/2026.