View 2227 OAKINGTON STREET Winter Garden, FL MLS# O6414707
$489,990
4

Beds

2.0

Baths

1,867

Sq.Ft.

2227 OAKINGTON STREET

Winter Garden, FL

Courtesy of REALTY ONE GROUP EVOLUTION
View 13011 TRANQUIL WATER ALLEY Winter Garden, FL MLS# O6414240
  • New Construction with Virtual Tour
1 of 33
$534,990
3

Beds

2.1

Baths

2,078

Sq.Ft.

13011 TRANQUIL WATER ALLEY

Winter Garden, FL

Courtesy of LPT REALTY LLC
View 12391 SILK MIMOSA ALLEY Winter Garden, FL MLS# O6414276
$607,679
4

Beds

3.0

Baths

2,200

Sq.Ft.

12391 SILK MIMOSA ALLEY

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 8921 FOUNTAIN PALM ALLEY Winter Garden, FL MLS# O6415441
$559,000
3

Beds

2.1

Baths

2,134

Sq.Ft.

8921 FOUNTAIN PALM ALLEY

Winter Garden, FL

View 8220 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# O6412974
$539,900
4

Beds

3.1

Baths

2,477

Sq.Ft.

8220 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of SERHANT
View 12792 SUNSET WALK DRIVE Winter Garden, FL MLS# O6414001
$527,000
4

Beds

3.0

Baths

1,930

Sq.Ft.

12792 SUNSET WALK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 1061 PORTMOOR WAY Winter Garden, FL MLS# G5113349
$515,000
4

Beds

2.0

Baths

1,804

Sq.Ft.

1061 PORTMOOR WAY

Winter Garden, FL

Courtesy of ENGEL & VOLKERS CLERMONT
View 16466 OLIVE HILL DRIVE Winter Garden, FL MLS# O6409922
$640,000
3

Beds

2.1

Baths

2,020

Sq.Ft.

16466 OLIVE HILL DRIVE

Winter Garden, FL

View 12808 SUNSET WALK DRIVE Winter Garden, FL MLS# O6413517
  • New Construction with Virtual Tour
1 of 7
$495,000
4

Beds

3.0

Baths

1,897

Sq.Ft.

12808 SUNSET WALK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 13861 EASDALE ALLEY Winter Garden, FL MLS# O6413534
  • New Construction with Virtual Tour
1 of 15
$539,000
4

Beds

3.0

Baths

2,031

Sq.Ft.

13861 EASDALE ALLEY

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 7531 SILVER VALLEY STREET Winter Garden, FL MLS# G5113297
$552,275
4

Beds

3.0

Baths

2,102

Sq.Ft.

7531 SILVER VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13878 PEACH ORCHARD WAY Winter Garden, FL MLS# O6413152
$569,900
4

Beds

3.0

Baths

2,115

Sq.Ft.

13878 PEACH ORCHARD WAY

Winter Garden, FL

View 12427 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# O6413423
$499,990
4

Beds

3.0

Baths

2,200

Sq.Ft.

12427 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

View 636 SIGLER DRIVE Winter Garden, FL MLS# O6413662
  • New Construction with Virtual Tour
1 of 13
$611,610
3

Beds

2.1

Baths

1,634

Sq.Ft.

636 SIGLER DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 11165 GREEN CITRON ALLEY Winter Garden, FL MLS# O6413226
$648,000
4

Beds

3.0

Baths

2,043

Sq.Ft.

11165 GREEN CITRON ALLEY

Winter Garden, FL

View 17035 HARBOR OAK PARKWAY Winter Garden, FL MLS# O6411409
$499,999
3

Beds

2.0

Baths

1,692

Sq.Ft.

17035 HARBOR OAK PARKWAY

Winter Garden, FL

View 15806 GEM VIEW ST Winter Garden, FL MLS# C7526682
  • Adult Community with Virtual Tour
1 of 37
$495,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

15806 GEM VIEW ST

Winter Garden, FL

Courtesy of FAST ACTION REALTY INC
View 16596 POINT ROCK DRIVE Winter Garden, FL MLS# O6412721
  • Virtual Tour
1 of 54
OPEN HOUSE: Saturday 7/18 10:30 AM - 3:00 PM
$539,900
3

Beds

2.1

Baths

2,216

Sq.Ft.

16596 POINT ROCK DRIVE

Winter Garden, FL

View 181 ZACHARY WADE STREET Winter Garden, FL MLS# O6412174
$600,000
5

Beds

3.0

Baths

2,940

Sq.Ft.

181 ZACHARY WADE STREET

Winter Garden, FL

View 6279 SUNNY TIME AVENUE Winter Garden, FL MLS# O6412141
  • New Construction with Virtual Tour
1 of 28
$546,490
3

Beds

2.1

Baths

1,913

Sq.Ft.

6279 SUNNY TIME AVENUE

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC

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

918

Estimated median home price

$608,645
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 - 400K62
$400K - 500K130
$500K - 600K148
$600K - 700K97
$700K - 800K105
$800K - 900K86
$900K - 1M59
$1M - Max115

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family619
Townhouse127
Condo139
Commercial11
Rental209
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/18/2026)

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.

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 7/18/2026.