View 13891 TITLE WAY Winter Garden, FL MLS# S5150456
  • Recently Listed with Virtual Tour
1 of 25
$2,850
4

Beds

3.1

Baths

2,492

Sq.Ft.

13891 TITLE WAY

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 8325 TOPSAIL PLACE Winter Garden, FL MLS# O6409999
  • Recently Listed with Virtual Tour
1 of 74
$4,000
3

Beds

2.0

Baths

2,170

Sq.Ft.

8325 TOPSAIL PLACE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13340 PONTOON ROAD Winter Garden, FL MLS# S5150425
  • Recently Listed with Virtual Tour
1 of 15
$2,850
3

Beds

2.1

Baths

1,814

Sq.Ft.

13340 PONTOON ROAD

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 14387 BRAEMAR STREET Winter Garden, FL MLS# G5111869
  • Recently Listed with Virtual Tour
1 of 22
$2,950
4

Beds

2.1

Baths

2,094

Sq.Ft.

14387 BRAEMAR STREET

Winter Garden, FL

Courtesy of SCATES REALTY & INVESTMENT PRO
View 430 SOUTHERN PECAN CIRCLE 101 Winter Garden, FL MLS# O6409326
  • Recently Listed with Virtual Tour
1 of 48
$1,995
2

Beds

2.0

Baths

1,152

Sq.Ft.

430 SOUTHERN PECAN CIRCLE 101

Winter Garden, FL

Courtesy of CANI PROPERTY MANAGEMENT
View 12561 WESTFIELD LAKES CIRCLE Winter Garden, FL MLS# O6409526
  • Recently Listed with Virtual Tour
1 of 39
$3,950
4

Beds

3.0

Baths

2,935

Sq.Ft.

12561 WESTFIELD LAKES CIRCLE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 13007 TOLLCROSS WAY Winter Garden, FL MLS# O6410351
  • Recently Listed with Virtual Tour
1 of 46
$3,400
4

Beds

3.0

Baths

2,160

Sq.Ft.

13007 TOLLCROSS WAY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 13370 DANIELS LANDING CIRCLE Winter Garden, FL MLS# O6408989
  • Recently Listed with Virtual Tour
1 of 26
$2,275
2

Beds

2.1

Baths

1,236

Sq.Ft.

13370 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of EATON REALTY SERVICES
View 16031 SILVER BROOK WAY Winter Garden, FL MLS# O6409094
  • Recently Listed with Virtual Tour
1 of 37
$6,500
5

Beds

4.1

Baths

3,979

Sq.Ft.

16031 SILVER BROOK WAY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 16751 HAMLIN VISTA ALLEY Winter Garden, FL MLS# O6409863
  • Recently Listed with Virtual Tour
1 of 38
$3,150
4

Beds

3.1

Baths

2,088

Sq.Ft.

16751 HAMLIN VISTA ALLEY

Winter Garden, FL

Courtesy of TRUSTHOME PROPERTIES INC
View 15350 OAK APPLE COURT 17B Winter Garden, FL MLS# O6409283
  • Recently Listed with Virtual Tour
1 of 21
$2,250
3

Beds

2.1

Baths

1,544

Sq.Ft.

15350 OAK APPLE COURT 17B

Winter Garden, FL

Courtesy of FLORIDA RENTAL TEAM
View 9354 LAKE HICKORY NUT DRIVE Winter Garden, FL MLS# O6408572
$4,750
3

Beds

3.1

Baths

2,278

Sq.Ft.

9354 LAKE HICKORY NUT DRIVE

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 15064 GROVE LAKE DRIVE Winter Garden, FL MLS# O6408824
  • Recently Listed with Virtual Tour
1 of 12
$3,300
3

Beds

2.1

Baths

1,846

Sq.Ft.

15064 GROVE LAKE DRIVE

Winter Garden, FL

Courtesy of AMERILEAD REALTY LLC
View 15212 TRIBUTE OVATION WAY Winter Garden, FL MLS# O6408830
  • Recently Listed with Virtual Tour
1 of 9
$3,200
3

Beds

2.1

Baths

1,688

Sq.Ft.

15212 TRIBUTE OVATION WAY

Winter Garden, FL

Courtesy of RIGHTHOUSE REALTY LLC
View 15602 COMPASS ROSE STREET Winter Garden, FL MLS# O6408929
  • Recently Listed with Virtual Tour
1 of 69
$3,900
5

Beds

4.1

Baths

3,227

Sq.Ft.

15602 COMPASS ROSE STREET

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 15086 LEBEAU LOOP Winter Garden, FL MLS# O6408906
$3,275
4

Beds

4.0

Baths

2,688

Sq.Ft.

15086 LEBEAU LOOP

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 14286 BRAEMAR STREET Winter Garden, FL MLS# O6408832
$2,850
4

Beds

2.1

Baths

2,114

Sq.Ft.

14286 BRAEMAR STREET

Winter Garden, FL

Courtesy of POINTON REALTY INC
View 11965 BRACCO STREET Winter Garden, FL MLS# O6407048
  • Recently Listed with Virtual Tour
1 of 45
$3,600
4

Beds

3.0

Baths

2,424

Sq.Ft.

11965 BRACCO STREET

Winter Garden, FL

Courtesy of ALLUX REAL ESTATE LLC
View 10264 LOVE STORY STREET Winter Garden, FL MLS# O6409006
  • Recently Listed with Virtual Tour
1 of 33
$6,000
5

Beds

3.0

Baths

3,359

Sq.Ft.

10264 LOVE STORY STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 8119 LAUGHING GULL STREET Winter Garden, FL MLS# O6408656
  • Recently Listed with Virtual Tour
1 of 45
$3,400
4

Beds

2.0

Baths

2,043

Sq.Ft.

8119 LAUGHING GULL STREET

Winter Garden, FL

Courtesy of RC REALTY GROUP 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

1,041

Estimated median home price

$609,900
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 - 100K2
$100K - 200K21
$200K - 300K98
$300K - 400K83
$400K - 500K141
$500K - 600K168
$600K - 700K124
$700K - 800K118
$800K - 900K87
$900K - 1M74
$1M - Max125

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family713
Townhouse141
Condo145
Commercial10
Rental211
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/24/2026)

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 5/24/2026.