View 14542 BLACK CHERRY TRAIL Winter Garden, FL MLS# O6410574
$575,000
4

Beds

2.1

Baths

2,234

Sq.Ft.

14542 BLACK CHERRY TRAIL

Winter Garden, FL

View 1158 ORANGE SEASON LANE Winter Garden, FL MLS# O6402123
$525,000
3

Beds

2.1

Baths

2,444

Sq.Ft.

1158 ORANGE SEASON LANE

Winter Garden, FL

View 516 S HIGHLAND AVENUE Winter Garden, FL MLS# O6409675
$500,000
3

Beds

2.0

Baths

1,716

Sq.Ft.

516 S HIGHLAND AVENUE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 231 DOE RUN DRIVE Winter Garden, FL MLS# O6412284
$498,995
4

Beds

2.0

Baths

1,972

Sq.Ft.

231 DOE RUN DRIVE

Winter Garden, FL

View 1005 CHASE DRIVE Winter Garden, FL MLS# O6411451
$599,999
4

Beds

2.1

Baths

2,319

Sq.Ft.

1005 CHASE DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15806 GEM VIEW ST Winter Garden, FL MLS# A12029648
  • Adult Community with Virtual Tour
1 of 37
$495,000
2

Beds

2.0

Baths

15806 GEM VIEW ST

Winter Garden, FL

Courtesy of FAST ACTION REALTY INC
View 16130 WIND VIEW LANE Winter Garden, FL MLS# O6412051
  • Recently Listed with Virtual Tour
1 of 65
$550,000
4

Beds

3.0

Baths

2,031

Sq.Ft.

16130 WIND VIEW LANE

Winter Garden, FL

View 8016 SWEET ORANGE AVENUE Winter Garden, FL MLS# TB8511160
$537,900
4

Beds

2.1

Baths

2,084

Sq.Ft.

8016 SWEET ORANGE AVENUE

Winter Garden, FL

View 11036 ROBERT FROST DRIVE Winter Garden, FL MLS# O6410350
$634,990
4

Beds

3.0

Baths

2,136

Sq.Ft.

11036 ROBERT FROST DRIVE

Winter Garden, FL

View 33 TIMBERCREEK PINES CIRCLE Winter Garden, FL MLS# O6408941
$525,000
3

Beds

2.0

Baths

1,600

Sq.Ft.

33 TIMBERCREEK PINES CIRCLE

Winter Garden, FL

View 16186 HONEY HARVEST STREET Winter Garden, FL MLS# O6411495
$610,000
4

Beds

3.1

Baths

2,445

Sq.Ft.

16186 HONEY HARVEST STREET

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 5040 BREEZY ACRES STREET Winter Garden, FL MLS# O6409467
$670,000
4

Beds

3.1

Baths

2,724

Sq.Ft.

5040 BREEZY ACRES STREET

Winter Garden, FL

View 14246 CREEKBED CIRCLE Winter Garden, FL MLS# O6409378
$640,000
4

Beds

3.0

Baths

2,418

Sq.Ft.

14246 CREEKBED CIRCLE

Winter Garden, FL

View 9606 WOODCRANE DRIVE Winter Garden, FL MLS# O6410113
$525,000
3

Beds

2.1

Baths

2,101

Sq.Ft.

9606 WOODCRANE DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 46 W VINING STREET Winter Garden, FL MLS# O6408720
$544,900
3

Beds

2.0

Baths

1,273

Sq.Ft.

46 W VINING STREET

Winter Garden, FL

View 17124 BEACHGRASS ALLEY Winter Garden, FL MLS# O6408024
  • New Construction with Virtual Tour
1 of 4
$559,990
3

Beds

2.1

Baths

1,983

Sq.Ft.

17124 BEACHGRASS ALLEY

Winter Garden, FL

View 9360 MCLAREN ALLEY Winter Garden, FL MLS# O6408913
$575,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

9360 MCLAREN ALLEY

Winter Garden, FL

View 12410 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6409937
$639,990
3

Beds

2.0

Baths

1,860

Sq.Ft.

12410 ENCORE AT OVATION WAY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 15111 DRIFTWOOD BEND STREET Winter Garden, FL MLS# O6408574
$618,000
4

Beds

3.1

Baths

2,573

Sq.Ft.

15111 DRIFTWOOD BEND STREET

Winter Garden, FL

View 14784 FIELD DAISY DRIVE Winter Garden, FL MLS# O6408277
  • New Construction with Virtual Tour
1 of 45
$635,699
4

Beds

4.1

Baths

2,841

Sq.Ft.

14784 FIELD DAISY DRIVE

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

1,057

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 - 100K2
$100K - 200K24
$200K - 300K91
$300K - 400K67
$400K - 500K156
$500K - 600K179
$600K - 700K114
$700K - 800K127
$800K - 900K103
$900K - 1M63
$1M - Max131

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family742
Townhouse143
Condo137
Commercial9
Rental206
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 8/2/2026)

Information deemed reliable but not guaranteed.

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.

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 8/2/2026.