View 14838 DRIFTWATER DRIVE Winter Garden, FL MLS# O6454429
  • Recently Listed with Virtual Tour
1 of 48
$389,900
3

Beds

2.1

Baths

1,748

Sq.Ft.

14838 DRIFTWATER DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 17152 ARROWHEAD BOULEVARD Winter Garden, FL MLS# O6454938
  • Recently Listed with Virtual Tour
1 of 39
$449,000
4

Beds

2.0

Baths

1,458

Sq.Ft.

17152 ARROWHEAD BOULEVARD

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 331 BAYSIDE AVENUE Winter Garden, FL MLS# O6455899
$450,000
3

Beds

2.0

Baths

1,044

Sq.Ft.

331 BAYSIDE AVENUE

Winter Garden, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15032 LEBEAU LOOP Winter Garden, FL MLS# O6454792
  • Recently Listed with Virtual Tour
1 of 50
$499,000
3

Beds

2.1

Baths

1,945

Sq.Ft.

15032 LEBEAU LOOP

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 215 S WOODLAND STREET Winter Garden, FL MLS# O6455445
$425,000
4

Beds

2.0

Baths

1,685

Sq.Ft.

215 S WOODLAND STREET

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 13151 CALMING BREEZE WAY Winter Garden, FL MLS# O6455019
  • Recently Listed with Virtual Tour
1 of 28
OPEN HOUSE: Saturday 11/14 11:00 AM - 1:00 PM
$489,900
3

Beds

2.1

Baths

2,096

Sq.Ft.

13151 CALMING BREEZE WAY

Winter Garden, FL

Courtesy of REDFIN CORPORATION
View 226 CHARLOTTE STREET Winter Garden, FL MLS# O6455798
  • Recently Listed with Virtual Tour
1 of 45
$449,999
3

Beds

2.0

Baths

1,498

Sq.Ft.

226 CHARLOTTE STREET

Winter Garden, FL

Courtesy of INDEPENDENCE REALTY GROUP LLC
View 1388 WAVERUNNER LANE Winter Garden, FL MLS# O6455159
$515,000
4

Beds

3.0

Baths

2,030

Sq.Ft.

1388 WAVERUNNER LANE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 10503 SPRING ARBOR LANE Winter Garden, FL MLS# O6455202
$459,000
4

Beds

3.0

Baths

2,212

Sq.Ft.

10503 SPRING ARBOR LANE

Winter Garden, FL

Courtesy of UNIONE REALTY INC
View 6367 ARGENT WOOD DRIVE Winter Garden, FL MLS# O6454893
  • Recently Listed with Virtual Tour
1 of 30
$433,490
3

Beds

2.1

Baths

1,652

Sq.Ft.

6367 ARGENT WOOD DRIVE

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 6266 SUNNY TIME AVENUE Winter Garden, FL MLS# O6454896
  • Recently Listed with Virtual Tour
1 of 26
$429,890
3

Beds

2.1

Baths

1,683

Sq.Ft.

6266 SUNNY TIME AVENUE

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 14501 GROVE RESORT AVENUE 3618 Winter Garden, FL MLS# S5160518
  • Recently Listed with Virtual Tour
1 of 12
$430,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 3618

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
View 14347 S Braemar Street Winter Garden, FL MLS# B26094076
  • Recently Listed with Virtual Tour
1 of 33
$493,000
4

Beds

2.1

Baths

2,088

Sq.Ft.

14347 S Braemar Street

Winter Garden, FL

View 14347 BRAEMAR STREET Winter Garden, FL MLS# O6451972
  • Recently Listed with Virtual Tour
1 of 36
$493,000
4

Beds

2.1

Baths

2,088

Sq.Ft.

14347 BRAEMAR STREET

Winter Garden, FL

Courtesy of GARCIA REALTY GROUP
View 7183 SUMMERLAKE GROVES STREET Winter Garden, FL MLS# O6450879
$465,000
3

Beds

2.1

Baths

1,875

Sq.Ft.

7183 SUMMERLAKE GROVES STREET

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 5567 CYPRESS HILL ROAD Winter Garden, FL MLS# O6453267
$519,995
3

Beds

2.0

Baths

1,650

Sq.Ft.

5567 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of CT HOMES REALTY CORPORATION
View 14026 FRASIER STREET Winter Garden, FL MLS# O6451346
$464,900
3

Beds

2.1

Baths

1,985

Sq.Ft.

14026 FRASIER STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 15102 STUTTGART ALLEY Winter Garden, FL MLS# O6452362
  • Recently Listed with Virtual Tour
1 of 62
OPEN HOUSE: Thursday 11/12 12:00 PM - 4:00 PM
$515,000
4

Beds

2.1

Baths

2,204

Sq.Ft.

15102 STUTTGART ALLEY

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 13537 SPLASHING ISLA DRIVE Winter Garden, FL MLS# TB8560424
  • Recently Listed with Virtual Tour
1 of 66
$430,000
3

Beds

2.0

Baths

1,574

Sq.Ft.

13537 SPLASHING ISLA DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS-PLANT CITY
View 6707 MARMALADE ALLEY Winter Garden, FL MLS# O6452928
$480,000
4

Beds

3.1

Baths

1,902

Sq.Ft.

6707 MARMALADE ALLEY

Winter Garden, FL

Courtesy of HOMEVEST REALTY

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

947

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 - 200K37
$200K - 300K73
$300K - 400K67
$400K - 500K143
$500K - 600K146
$600K - 700K115
$700K - 800K102
$800K - 900K103
$900K - 1M54
$1M - Max106

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family648
Townhouse142
Condo116
Commercial5
Rental249
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home1
Farms0

(Data as of 11/12/2026)

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 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 11/13/2026.