824 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 217 HARBOR DRIVE Winter Garden, FL MLS# O6437038
  • Recently Listed with Virtual Tour
1 of 45
$515,000
3

Beds

2.0

Baths

1,737

Sq.Ft.

217 HARBOR DRIVE

Winter Garden, FL

View 1424 SCARLET OAK LOOP Winter Garden, FL MLS# O6436325
  • Recently Listed with Virtual Tour
1 of 42
$379,000
3

Beds

2.1

Baths

1,737

Sq.Ft.

1424 SCARLET OAK LOOP

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 2542 Winter Garden, FL MLS# O6436045
$205,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 2542

Winter Garden, FL

Courtesy of REAL BROKER, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 14501 GROVE RESORT AVENUE 1420 Winter Garden, FL MLS# S5156458
  • Recently Listed with Virtual Tour
1 of 37
$249,000
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 1420

Winter Garden, FL

View 2017 PORTCASTLE CIRCLE Winter Garden, FL MLS# O6437283
$410,000
3

Beds

2.1

Baths

1,857

Sq.Ft.

2017 PORTCASTLE CIRCLE

Winter Garden, FL

View 2716 GORST RD Winter Garden, FL MLS# O6437314
  • Recently Listed with Virtual Tour
1 of 30
OPEN HOUSE: Sunday 9/6 1:00 PM - 3:00 PM
$859,000
5

Beds

5.0

Baths

3,935

Sq.Ft.

2716 GORST RD

Winter Garden, FL

View 9982 BEACH PORT DRIVE Winter Garden, FL MLS# O6437583
  • Recently Listed with Virtual Tour
1 of 43
OPEN HOUSE: Saturday 9/5 11:00 AM - 5:00 PM
$825,000
4

Beds

3.1

Baths

2,921

Sq.Ft.

9982 BEACH PORT DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16273 TALIESIN STREET Winter Garden, FL MLS# S5156149
  • Recently Listed with Virtual Tour
1 of 45
$565,000
3

Beds

2.1

Baths

1,836

Sq.Ft.

16273 TALIESIN STREET

Winter Garden, FL

View 427 REGAL DOWNS CIRCLE Winter Garden, FL MLS# O6433640
$475,000
5

Beds

2.1

Baths

2,135

Sq.Ft.

427 REGAL DOWNS CIRCLE

Winter Garden, FL

View 15873 GEM VIEW STREET Winter Garden, FL MLS# O6435893
  • Recently Listed with Virtual Tour
1 of 58
$419,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

15873 GEM VIEW STREET

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View 393 LAKE AMBERLEIGH DRIVE Winter Garden, FL MLS# O6436549
  • Recently Listed with Virtual Tour
1 of 29
$600,000
3

Beds

2.1

Baths

2,684

Sq.Ft.

393 LAKE AMBERLEIGH DRIVE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 16771 OAKBORO STREET STREET Winter Garden, FL MLS# O6436008
$787,000
5

Beds

4.0

Baths

2,840

Sq.Ft.

16771 OAKBORO STREET STREET

Winter Garden, FL

Courtesy of DOUGLAS ELLIMAN
View 16050 HONEY HARVEST STREET Winter Garden, FL MLS# O6436917
  • Recently Listed with Virtual Tour
1 of 32
$560,000
3

Beds

3.1

Baths

2,461

Sq.Ft.

16050 HONEY HARVEST STREET

Winter Garden, FL

View 14751 FIELD DAISY DRIVE Winter Garden, FL MLS# O6436927
  • Recently Listed with Virtual Tour
1 of 40
$560,000
3

Beds

2.1

Baths

2,461

Sq.Ft.

14751 FIELD DAISY DRIVE

Winter Garden, FL

View 7278 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6436600
  • Recently Listed with Virtual Tour
1 of 30
$599,000
4

Beds

2.0

Baths

2,014

Sq.Ft.

7278 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 12728 CHARMED DRIVE Winter Garden, FL MLS# O6437239
  • Recently Listed with Virtual Tour
1 of 51
$835,000
5

Beds

4.1

Baths

3,231

Sq.Ft.

12728 CHARMED DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13112 DENDY WAY Winter Garden, FL MLS# O6437516
  • Recently Listed with Virtual Tour
1 of 58
$825,000
5

Beds

4.0

Baths

3,285

Sq.Ft.

13112 DENDY WAY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 12349 SILK MIMOSA ALLEY Winter Garden, FL MLS# O6436494
$652,990
4

Beds

4.0

Baths

2,622

Sq.Ft.

12349 SILK MIMOSA ALLEY

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 17392 SWEET MORO DRIVE Winter Garden, FL MLS# TB8542299
  • New Construction with Virtual Tour
1 of 28
$459,922
3

Beds

2.1

Baths

1,577

Sq.Ft.

17392 SWEET MORO DRIVE

Winter Garden, FL

View 14200 AVALON ROAD 406 Winter Garden, FL MLS# O6433742
  • Recently Listed with Virtual Tour
1 of 31
$220,000
3

Beds

2.0

Baths

1,288

Sq.Ft.

14200 AVALON ROAD 406

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

998

Estimated median home price

$606,720
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 - 200K21
$200K - 300K90
$300K - 400K70
$400K - 500K147
$500K - 600K167
$600K - 700K104
$700K - 800K110
$800K - 900K112
$900K - 1M62
$1M - Max114

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family698
Townhouse136
Condo129
Commercial7
Rental183
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 9/5/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

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. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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 real estate for sale/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein or for their use or interpretation by the user. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

This data updated periodically, at an interval not to exceed 7 days.

IDX information 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

© Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

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 9/6/2026.