View 1996 N OLD KILLARNEY STREET Winter Garden, FL MLS# O6392668
  • Recently Listed with Virtual Tour
1 of 9
$1,600
1

Beds

1.0

Baths

1,100

Sq.Ft.

1996 N OLD KILLARNEY STREET

Winter Garden, FL

Courtesy of DALTON WADE INC
View 1604 SCARLET OAK LOOP 63B Winter Garden, FL MLS# O6391499
  • Recently Listed with Virtual Tour
1 of 30
$2,500
3

Beds

2.1

Baths

1,544

Sq.Ft.

1604 SCARLET OAK LOOP 63B

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 5374 LAKE VIRGINIA STREET Winter Garden, FL MLS# O6391529
  • Recently Listed with Virtual Tour
1 of 33
$3,650
4

Beds

3.0

Baths

2,038

Sq.Ft.

5374 LAKE VIRGINIA STREET

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 7091 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6391565
  • Recently Listed with Virtual Tour
1 of 25
$2,700
3

Beds

2.1

Baths

1,845

Sq.Ft.

7091 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View 1519 BROKEN OAK DRIVE B Winter Garden, FL MLS# O6391579
  • Recently Listed with Virtual Tour
1 of 34
$2,200
3

Beds

2.1

Baths

1,544

Sq.Ft.

1519 BROKEN OAK DRIVE B

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 16001 GRAFTON WAY Winter Garden, FL MLS# S5145973
  • Recently Listed with Virtual Tour
1 of 35
$2,850
3

Beds

2.1

Baths

1,850

Sq.Ft.

16001 GRAFTON WAY

Winter Garden, FL

Courtesy of AROD PARTNERS REALTY
View 918 WOODSON HAMMOCK CIR Winter Garden, FL MLS# O6391458
  • Recently Listed with Virtual Tour
1 of 34
$3,500
4

Beds

2.0

Baths

2,487

Sq.Ft.

918 WOODSON HAMMOCK CIR

Winter Garden, FL

Courtesy of SUNDIAL REAL ESTATE LLC
View 13605 DANIELS LANDING CIRCLE Winter Garden, FL MLS# O6391024
  • Recently Listed with Virtual Tour
1 of 15
$2,300
3

Beds

2.1

Baths

1,347

Sq.Ft.

13605 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of THE LISTING REAL ESTATE MANAGEMENT
View 15372 GILLIGAN COURT Winter Garden, FL MLS# O6391140
  • Recently Listed with Virtual Tour
1 of 33
$6,000
4

Beds

3.1

Baths

2,781

Sq.Ft.

15372 GILLIGAN COURT

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15501 HONEYBELL DRIVE Winter Garden, FL MLS# S5145302
  • Recently Listed with Virtual Tour
1 of 22
$2,900
3

Beds

2.1

Baths

1,611

Sq.Ft.

15501 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of MBT REALTY LLC
View 9133 MELLOW CORAL STREET Winter Garden, FL MLS# O6390848
  • Recently Listed with Virtual Tour
1 of 23
$2,550
3

Beds

2.1

Baths

1,451

Sq.Ft.

9133 MELLOW CORAL STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17651 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6390876
  • Recently Listed with Virtual Tour
1 of 23
$3,000
3

Beds

2.0

Baths

1,788

Sq.Ft.

17651 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 15915 MARINA BAY DRIVE Winter Garden, FL MLS# O6390934
  • Recently Listed with Virtual Tour
1 of 33
$2,700
3

Beds

2.1

Baths

1,804

Sq.Ft.

15915 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of JULIAN PROPERTIES, INC.
View 7711 TANGERINE KNOLL LOOP Winter Garden, FL MLS# O6390112
$3,385
4

Beds

3.1

Baths

2,697

Sq.Ft.

7711 TANGERINE KNOLL LOOP

Winter Garden, FL

Courtesy of TRUVISION REAL ESTATE LLC
View 8085 GLENLLOYD AVENUE Winter Garden, FL MLS# O6390827
  • Recently Listed with Virtual Tour
1 of 36
$2,700
3

Beds

2.1

Baths

1,599

Sq.Ft.

8085 GLENLLOYD AVENUE

Winter Garden, FL

Courtesy of JULIAN PROPERTIES, INC.
View 16917 TESLA ALLEY Winter Garden, FL MLS# O6392623
  • Recently Listed with Virtual Tour
1 of 35
$2,600
3

Beds

2.1

Baths

1,568

Sq.Ft.

16917 TESLA ALLEY

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View 705 HENNIS ROAD Winter Garden, FL MLS# O6390677
  • Recently Listed with Virtual Tour
1 of 18
$52,206
11,865

Sq.Ft.

705 HENNIS ROAD

Winter Garden, FL

Courtesy of ROI AVE LLC
View 12063 WALMSLEY ALY Winter Garden, FL MLS# O6390732
  • New Construction with Virtual Tour
1 of 34
$2,600
3

Beds

2.0

Baths

1,603

Sq.Ft.

12063 WALMSLEY ALY

Winter Garden, FL

Courtesy of DREAM FINDERS REALTY GROUP CORP
View 14366 ORCHARD HILLS BOULEVARD Winter Garden, FL MLS# S5145483
  • Recently Listed with Virtual Tour
1 of 32
$2,950
4

Beds

3.1

Baths

2,486

Sq.Ft.

14366 ORCHARD HILLS BOULEVARD

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 16662 WINGSPREAD LOOP Winter Garden, FL MLS# O6389787
  • Recently Listed
1 of 24
$3,200
3

Beds

2.1

Baths

2,372

Sq.Ft.

16662 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of PARK PLACE LENDING & INVESTMENTS 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

947

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 14
$200K - 300K 92
$300K - 400K 79
$400K - 500K 157
$500K - 600K 156
$600K - 700K 111
$700K - 800K 90
$800K - 900K 78
$900K - 1M 58
$1M - Max 108

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 641
Townhouse 143
Condo 126
Commercial 12
Rental 228
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 3/24/2026)

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 3/25/2026.