View 13006 SERENE GLADE ROAD Winter Garden, FL MLS# S5152909
  • Recently Listed with Virtual Tour
1 of 36
$555,000
3

Beds

2.1

Baths

2,096

Sq.Ft.

13006 SERENE GLADE ROAD

Winter Garden, FL

View 14816 PORTER RD Winter Garden, FL MLS# O6423001
  • Recently Listed with Virtual Tour
1 of 61
$545,000
5

Beds

3.0

Baths

2,790

Sq.Ft.

14816 PORTER RD

Winter Garden, FL

View 2025 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# O6422627
  • Recently Listed with Virtual Tour
1 of 60
$715,000
5

Beds

4.0

Baths

2,655

Sq.Ft.

2025 WINTERMERE POINTE DRIVE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 16625 POINT ROCK DRIVE Winter Garden, FL MLS# O6423042
  • Recently Listed with Virtual Tour
1 of 53
$569,900
3

Beds

2.1

Baths

2,216

Sq.Ft.

16625 POINT ROCK DRIVE

Winter Garden, FL

View 16936 TRADEWIND POINT Winter Garden, FL MLS# O6424578
  • Recently Listed with Virtual Tour
1 of 54
OPEN HOUSE: Sunday 7/19 11:00 AM - 2:00 PM
$645,000
4

Beds

3.1

Baths

2,930

Sq.Ft.

16936 TRADEWIND POINT

Winter Garden, FL

View 15026 SUMMER HARVEST STREET Winter Garden, FL MLS# S5153036
  • Recently Listed with Virtual Tour
1 of 41
$669,990
5

Beds

4.1

Baths

2,930

Sq.Ft.

15026 SUMMER HARVEST STREET

Winter Garden, FL

View 16645 SILVER BROOK WAY Winter Garden, FL MLS# O6420565
$573,090
3

Beds

2.1

Baths

1,913

Sq.Ft.

16645 SILVER BROOK WAY

Winter Garden, FL

View 1808 WESTERN TRAILWAY DRIVE Winter Garden, FL MLS# S5152973
  • Recently Listed with Virtual Tour
1 of 34
OPEN HOUSE: Sunday 7/19 12:00 PM - 2:00 PM
$599,000
3

Beds

2.0

Baths

1,860

Sq.Ft.

1808 WESTERN TRAILWAY DRIVE

Winter Garden, FL

Courtesy of FLORIDA IN MOTION REALTY INC
View 1642 CHANDELLE LANE Winter Garden, FL MLS# G5114093
  • Recently Listed with Virtual Tour
1 of 46
$709,900
5

Beds

3.0

Baths

2,918

Sq.Ft.

1642 CHANDELLE LANE

Winter Garden, FL

View 8873 FOUNTAIN PALM ALLEY Winter Garden, FL MLS# O6423477
  • Recently Listed with Virtual Tour
1 of 45
$565,000
3

Beds

2.1

Baths

2,162

Sq.Ft.

8873 FOUNTAIN PALM ALLEY

Winter Garden, FL

View 6207 SUNNY TIME AVENUE Winter Garden, FL MLS# O6421162
  • New Construction with Virtual Tour
1 of 23
$547,190
3

Beds

2.1

Baths

1,628

Sq.Ft.

6207 SUNNY TIME AVENUE

Winter Garden, FL

View 6137 WATERSIDE ISLAND LANE Winter Garden, FL MLS# O6418786
  • Recently Listed with Virtual Tour
1 of 34
$599,900
4

Beds

3.1

Baths

2,607

Sq.Ft.

6137 WATERSIDE ISLAND LANE

Winter Garden, FL

View 12632 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# S5152652
  • Recently Listed with Virtual Tour
1 of 20
$575,000
4

Beds

2.1

Baths

2,148

Sq.Ft.

12632 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

View 502 PALM DRIVE Winter Garden, FL MLS# O6415316
  • Recently Listed with Virtual Tour
1 of 59
$710,000
4

Beds

2.1

Baths

3,009

Sq.Ft.

502 PALM DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 17059 HARBOR OAK PARKWAY Winter Garden, FL MLS# G5114379
  • Recently Listed with Virtual Tour
1 of 67
$620,000
4

Beds

3.0

Baths

2,692

Sq.Ft.

17059 HARBOR OAK PARKWAY

Winter Garden, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 8937 LAKESHORE POINTE DRIVE Winter Garden, FL MLS# O6420679
  • Recently Listed with Virtual Tour
1 of 39
$585,000
3

Beds

2.1

Baths

2,052

Sq.Ft.

8937 LAKESHORE POINTE DRIVE

Winter Garden, FL

View 15725 SWEET LIMETTA DRIVE Winter Garden, FL MLS# O6420557
  • Recently Listed with Virtual Tour
1 of 55
$704,900
3

Beds

2.1

Baths

2,571

Sq.Ft.

15725 SWEET LIMETTA DRIVE

Winter Garden, FL

View 9166 CUT SHOT DRIVE Winter Garden, FL MLS# O6417611
$568,000
5

Beds

3.0

Baths

2,638

Sq.Ft.

9166 CUT SHOT DRIVE

Winter Garden, FL

View 13155 SPRING GROVE WAY Winter Garden, FL MLS# O6421867
  • Recently Listed with Virtual Tour
1 of 50
$600,000
4

Beds

3.1

Baths

2,818

Sq.Ft.

13155 SPRING GROVE WAY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 6587 OLD CARRIAGE ROAD Winter Garden, FL MLS# O6421933
$645,000
3

Beds

2.0

Baths

2,224

Sq.Ft.

6587 OLD CARRIAGE ROAD

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

951

Estimated median home price

$611,610
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 - 300K93
$300K - 400K61
$400K - 500K129
$500K - 600K161
$600K - 700K99
$700K - 800K113
$800K - 900K92
$900K - 1M63
$1M - Max117

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family654
Townhouse126
Condo138
Commercial11
Rental210
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/19/2026)

Information deemed reliable but not guaranteed.

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 7/19/2026.