View 1646 HOLCOMB CREEK STREET Winter Garden, FL MLS# O6394506
  • Recently Listed with Virtual Tour
1 of 49
$949,900
4

Beds

4.1

Baths

3,841

Sq.Ft.

1646 HOLCOMB CREEK STREET

Winter Garden, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 15373 LAKE KILLARNEY COURT Winter Garden, FL MLS# O6394209
  • Recently Listed with Virtual Tour
1 of 53
$829,000
5

Beds

4.0

Baths

3,623

Sq.Ft.

15373 LAKE KILLARNEY COURT

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 15162 SPINNAKER COVE LANE Winter Garden, FL MLS# O6393190
$850,000
5

Beds

3.0

Baths

3,902

Sq.Ft.

15162 SPINNAKER COVE LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 12595 GOLD HONEYSUCKLE STREET 284 Winter Garden, FL MLS# O6393961
$859,990
4

Beds

3.1

Baths

3,338

Sq.Ft.

12595 GOLD HONEYSUCKLE STREET 284

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 15324 GILLIGAN COURT Winter Garden, FL MLS# O6393498
  • Recently Listed with Virtual Tour
1 of 74
$950,000
4

Beds

3.1

Baths

2,794

Sq.Ft.

15324 GILLIGAN COURT

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 17326 BAL HARBOUR DRIVE Winter Garden, FL MLS# O6393857
  • Recently Listed with Virtual Tour
1 of 71
$790,000
5

Beds

3.0

Baths

3,196

Sq.Ft.

17326 BAL HARBOUR DRIVE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 17549 SEIDNER ROAD Winter Garden, FL MLS# O6392430
  • Recently Listed with Virtual Tour
1 of 37
$950,000
3

Beds

2.1

Baths

2,130

Sq.Ft.

17549 SEIDNER ROAD

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 14187 JOMATT LOOP Winter Garden, FL MLS# O6393373
  • Recently Listed with Virtual Tour
1 of 28
$949,900
6

Beds

3.1

Baths

4,181

Sq.Ft.

14187 JOMATT LOOP

Winter Garden, FL

Courtesy of ELEVATE REAL ESTATE BROKERS
View 15558 SANDFIELD LOOP Winter Garden, FL MLS# O6393987
  • Recently Listed with Virtual Tour
1 of 20
$795,000
4

Beds

3.1

Baths

4,307

Sq.Ft.

15558 SANDFIELD LOOP

Winter Garden, FL

Courtesy of ORLANDO HIGHLAND REALTY LLC
View 14050 FAIRWAY WILLOW LANE Winter Garden, FL MLS# O6392994
  • Recently Listed with Virtual Tour
1 of 52
$795,000
3

Beds

2.0

Baths

2,027

Sq.Ft.

14050 FAIRWAY WILLOW LANE

Winter Garden, FL

Courtesy of LAKEFIELD REALTY GROUP LLC
View 6261 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5110034
$890,955
6

Beds

4.0

Baths

4,236

Sq.Ft.

6261 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13526 FOX GLOVE STREET Winter Garden, FL MLS# O6388630
  • Recently Listed with Virtual Tour
1 of 54
$845,000
5

Beds

3.0

Baths

3,866

Sq.Ft.

13526 FOX GLOVE STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 6155 HAMLIN RESERVE BOULEVARD Winter Garden, FL MLS# O6393297
$975,000
5

Beds

4.1

Baths

3,778

Sq.Ft.

6155 HAMLIN RESERVE BOULEVARD

Winter Garden, FL

Courtesy of DALTON WADE INC
View 11205 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6392839
  • Recently Listed with Virtual Tour
1 of 31
$969,091
4

Beds

3.1

Baths

3,327

Sq.Ft.

11205 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 12965 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6392975
  • Recently Listed with Virtual Tour
1 of 31
$882,932
5

Beds

4.1

Baths

3,101

Sq.Ft.

12965 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 14354 WABASSO LOOP Winter Garden, FL MLS# O6392378
  • Recently Listed with Virtual Tour
1 of 59
$939,000
4

Beds

4.0

Baths

2,881

Sq.Ft.

14354 WABASSO LOOP

Winter Garden, FL

Courtesy of HOUWZER INC
View 15432 GILLIGAN COURT Winter Garden, FL MLS# O6392254
$831,000
5

Beds

4.1

Baths

3,267

Sq.Ft.

15432 GILLIGAN COURT

Winter Garden, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 1001 VINSETTA CIRCLE Winter Garden, FL MLS# O6392172
  • Recently Listed
1 of 57
$870,000
6

Beds

4.0

Baths

3,988

Sq.Ft.

1001 VINSETTA CIRCLE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 17060 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5109737
  • Recently Listed with Virtual Tour
1 of 7
$819,391
6

Beds

4.1

Baths

3,117

Sq.Ft.

17060 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17416 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109744
$784,490
4

Beds

2.1

Baths

2,688

Sq.Ft.

17416 SUNSET PRAIRIE 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

953

Estimated median home price

$589,000
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

Price Count
$0 - 100K 4
$100K - 200K 15
$200K - 300K 96
$300K - 400K 81
$400K - 500K 155
$500K - 600K 155
$600K - 700K 112
$700K - 800K 92
$800K - 900K 79
$900K - 1M 62
$1M - Max 102

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 646
Townhouse 144
Condo 128
Commercial 11
Rental 221
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 3/27/2026)

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 3/30/2026.