View 186 S MAIN STREET Winter Garden, FL MLS# O6359871
  • New Construction with Virtual Tour
1 of 7
$0
16,000

Sq.Ft.

186 S MAIN STREET

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 214 2ND STREET Winter Garden, FL MLS# O6449629
$1,100
1

Beds

1.0

Baths

300

Sq.Ft.

214 2ND STREET

Winter Garden, FL

Courtesy of ACTION PLUS REALTY SERVICES
View 1418 DANIELS COVE DRIVE Winter Garden, FL MLS# O6450341
$1,100
2

Beds

1.0

Baths

300

Sq.Ft.

1418 DANIELS COVE DRIVE

Winter Garden, FL

Courtesy of ACTION PLUS REALTY SERVICES
The time to sell is now! THE TIME TO SELL IS NOW!
View 502 DUNBAR AVENUE Winter Garden, FL MLS# O6438802
$1,399
2

Beds

1.0

Baths

816

Sq.Ft.

502 DUNBAR AVENUE

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 5966 FLOWERING CHERRY BEND B Winter Garden, FL MLS# O6454473
  • Recently Listed with Virtual Tour
1 of 12
$1,450
1

Beds

1.0

Baths

600

Sq.Ft.

5966 FLOWERING CHERRY BEND B

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 6393 WILD PERSIMMON WAY UNIT #B Winter Garden, FL MLS# O6450579
$1,500
1

Beds

1.1

Baths

600

Sq.Ft.

6393 WILD PERSIMMON WAY UNIT #B

Winter Garden, FL

Courtesy of MANAGER PROP
View 5972 FLOWERING CHERRY BEND UNIT #B Winter Garden, FL MLS# O6450562
$1,500
1

Beds

1.0

Baths

600

Sq.Ft.

5972 FLOWERING CHERRY BEND UNIT #B

Winter Garden, FL

Courtesy of MANAGER PROP
View 304 ERON WAY 2 Winter Garden, FL MLS# O6453109
  • Recently Listed with Virtual Tour
1 of 20
$1,500
2

Beds

2.0

Baths

840

Sq.Ft.

304 ERON WAY 2

Winter Garden, FL

Courtesy of LIBERTY HOME SALES INC
View 5350 LAKE VIRGINIA TRAIL B Winter Garden, FL MLS# O6452831
$1,575
1

Beds

1.0

Baths

624

Sq.Ft.

5350 LAKE VIRGINIA TRAIL B

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 430 SOUTHERN PECAN CIRCLE 106 Winter Garden, FL MLS# O6438120
$1,649
1

Beds

1.0

Baths

838

Sq.Ft.

430 SOUTHERN PECAN CIRCLE 106

Winter Garden, FL

Courtesy of AFT PROPERTY LLC
View 502 VARSITY STREET Winter Garden, FL MLS# O6433127
$1,675
2

Beds

1.0

Baths

780

Sq.Ft.

502 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 508 VARSITY STREET Winter Garden, FL MLS# O6433135
$1,675
2

Beds

1.0

Baths

780

Sq.Ft.

508 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 407 DOUGLAS WAY 66 Winter Garden, FL MLS# O6431468
$1,695
2

Beds

2.0

Baths

930

Sq.Ft.

407 DOUGLAS WAY 66

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 200 SOUTHERN PECAN CIRCLE 203 Winter Garden, FL MLS# S5152842
$1,750
2

Beds

2.0

Baths

1,276

Sq.Ft.

200 SOUTHERN PECAN CIRCLE 203

Winter Garden, FL

Courtesy of FLORIDA SCANDI REALTY LLC
View 509 VARSITY STREET Winter Garden, FL MLS# O6442711
$1,750
2

Beds

1.0

Baths

780

Sq.Ft.

509 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 170 WINDTREE LANE U Winter Garden, FL MLS# S5158953
$1,750
2

Beds

2.0

Baths

918

Sq.Ft.

170 WINDTREE LANE U

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View Address not provided Winter Garden, FL MLS# O6451141
  • Recently Listed with Virtual Tour
1 of 31
$1,750
3

Beds

2.0

Baths

1,156

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of THE EXPERTS TEAM REALTY INC
View 109 WINDTREE LANE N Winter Garden, FL MLS# G5119655
  • Recently Listed with Virtual Tour
1 of 14
$1,750
2

Beds

2.0

Baths

918

Sq.Ft.

109 WINDTREE LANE N

Winter Garden, FL

Courtesy of PROPERTY INVESTMENT SPECIALIST
View 433 SAND LIME ROAD Winter Garden, FL MLS# O6451945
$1,800
3

Beds

2.0

Baths

1,322

Sq.Ft.

433 SAND LIME ROAD

Winter Garden, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View 417 SOUTHERN PECAN CIRCLE 208 Winter Garden, FL MLS# O6448316
$1,825
2

Beds

2.0

Baths

1,264

Sq.Ft.

417 SOUTHERN PECAN CIRCLE 208

Winter Garden, FL

Courtesy of ALL COUNTY CFL PROPERTY MGMT

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

952

Estimated median home price

$607,468
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 - 200K35
$200K - 300K72
$300K - 400K67
$400K - 500K145
$500K - 600K152
$600K - 700K114
$700K - 800K105
$800K - 900K104
$900K - 1M53
$1M - Max103

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family652
Townhouse144
Condo117
Commercial5
Rental239
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home1
Farms0

(Data as of 11/8/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective 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 11/8/2026.