View 16292 BRIGHT LEAF ROAD Winter Garden, FL MLS# S5148798
$2,620
3

Beds

2.1

Baths

1,553

Sq.Ft.

16292 BRIGHT LEAF ROAD

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 12112 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6403110
$3,350
4

Beds

3.1

Baths

2,781

Sq.Ft.

12112 ENCORE AT OVATION WAY

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 9158 SONOMA COAST DRIVE Winter Garden, FL MLS# TB8502828
$3,495
4

Beds

3.0

Baths

2,117

Sq.Ft.

9158 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of 7 BLUE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 10013 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6402442
  • Recently Listed with Virtual Tour
1 of 34
$5,150
6

Beds

4.1

Baths

4,505

Sq.Ft.

10013 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of OKKLA REALTY
View 1570 SCARLET OAK LOOP C Winter Garden, FL MLS# O6402586
  • Recently Listed with Virtual Tour
1 of 41
$2,400
3

Beds

2.1

Baths

1,696

Sq.Ft.

1570 SCARLET OAK LOOP C

Winter Garden, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View 13071 INKWELL ALLEY Winter Garden, FL MLS# S5148709
  • Recently Listed with Virtual Tour
1 of 29
$2,750
4

Beds

3.0

Baths

2,042

Sq.Ft.

13071 INKWELL ALLEY

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 18386 OLIVER TWIST WAY Winter Garden, FL MLS# O6402380
  • Recently Listed with Virtual Tour
1 of 33
$4,300
4

Beds

3.0

Baths

2,674

Sq.Ft.

18386 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of REALTY HUB
View 6460 MAKRUT LIME DRIVE Winter Garden, FL MLS# O6402389
  • Recently Listed with Virtual Tour
1 of 48
$4,250
4

Beds

3.1

Baths

3,103

Sq.Ft.

6460 MAKRUT LIME DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 9131 CUT SHOT DRIVE Winter Garden, FL MLS# O6402316
  • Recently Listed with Virtual Tour
1 of 45
$3,150
5

Beds

3.0

Baths

2,638

Sq.Ft.

9131 CUT SHOT DRIVE

Winter Garden, FL

Courtesy of BLUE CHIP INTERNATIONAL REALTY LLC
View 15141 SUMMER HARVEST STREET Winter Garden, FL MLS# O6401976
  • Recently Listed with Virtual Tour
1 of 41
$3,500
4

Beds

3.1

Baths

2,278

Sq.Ft.

15141 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of GARCIA REALTY GROUP
View 17877 PHIL C PETERS RD Winter Garden, FL MLS# O6402176
  • Recently Listed with Virtual Tour
1 of 30
$4,299
3

Beds

2.0

Baths

2,501

Sq.Ft.

17877 PHIL C PETERS RD

Winter Garden, FL

Courtesy of REIS E SILVA REALTY GROUP LLC
View 143 SOUTHERN PECAN CIRCLE 201 Winter Garden, FL MLS# O6402229
  • Recently Listed with Virtual Tour
1 of 23
$2,400
3

Beds

2.0

Baths

1,453

Sq.Ft.

143 SOUTHERN PECAN CIRCLE 201

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 508 VARSITY STREET Winter Garden, FL MLS# O6401722
  • Recently Listed with Virtual Tour
1 of 10
$1,695
2

Beds

1.0

Baths

780

Sq.Ft.

508 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 9143 GRAND ISLAND WAY Winter Garden, FL MLS# S5148244
  • Recently Listed with Virtual Tour
1 of 14
$2,900
4

Beds

2.1

Baths

1,868

Sq.Ft.

9143 GRAND ISLAND WAY

Winter Garden, FL

Courtesy of K REALTY
View 11062 GREAT ROCK STREET Winter Garden, FL MLS# O6401925
  • Recently Listed with Virtual Tour
1 of 34
$2,650
3

Beds

2.1

Baths

1,888

Sq.Ft.

11062 GREAT ROCK STREET

Winter Garden, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 16593 BARBOURS CREEK WAY Winter Garden, FL MLS# O6400540
  • Recently Listed with Virtual Tour
1 of 28
$3,000
3

Beds

2.1

Baths

1,567

Sq.Ft.

16593 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of KAZA REAL ESTATE LLC
View 13527 DANIELS LANDING CIRCLE Winter Garden, FL MLS# S5148507
$2,300
3

Beds

2.1

Baths

1,365

Sq.Ft.

13527 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of Kissimmee - WEICHERT, REALTORS® - Hallmark Properties
View 16822 WINGSPREAD LOOP Winter Garden, FL MLS# O6402231
  • Recently Listed with Virtual Tour
1 of 31
$3,950
4

Beds

3.0

Baths

2,470

Sq.Ft.

16822 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of ASSURANCE FLORIDA REALTY
View 15030 SUMMER HARVEST STREET Winter Garden, FL MLS# O6400523
  • Recently Listed with Virtual Tour
1 of 17
$3,800
4

Beds

3.1

Baths

2,861

Sq.Ft.

15030 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of KICANTO REALTY
View 12032 HOLYSTONE STREET Winter Garden, FL MLS# O6401473
  • Recently Listed with Virtual Tour
1 of 47
$2,600
3

Beds

2.1

Baths

1,568

Sq.Ft.

12032 HOLYSTONE STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES

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

992

Estimated median home price

$605,948
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 - 200K18
$200K - 300K99
$300K - 400K80
$400K - 500K145
$500K - 600K151
$600K - 700K128
$700K - 800K109
$800K - 900K88
$900K - 1M67
$1M - Max106

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family680
Townhouse138
Condo136
Commercial11
Rental219
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 4/28/2026)

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 4/29/2026.