View 14366 ORCHARD HILLS BOULEVARD Winter Garden, FL MLS# S5145483
$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
$3,200
3

Beds

2.1

Baths

2,372

Sq.Ft.

16662 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of PARK PLACE LENDING & INVESTMENTS INC
View 15789 FOUNTAIN SPRINGS ROAD Winter Garden, FL MLS# O6389343
  • Recently Listed with Virtual Tour
1 of 32
$3,400
4

Beds

3.1

Baths

2,290

Sq.Ft.

15789 FOUNTAIN SPRINGS ROAD

Winter Garden, FL

Courtesy of JOHN SILVA REALTY & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 391 FLORAL DRIVE Winter Garden, FL MLS# O6389350
  • Recently Listed with Virtual Tour
1 of 38
$3,500
3

Beds

2.0

Baths

1,728

Sq.Ft.

391 FLORAL DRIVE

Winter Garden, FL

Courtesy of CANI PROPERTY MANAGEMENT
View 15537 MANGO ISLE STREET Winter Garden, FL MLS# S5145539
  • Recently Listed with Virtual Tour
1 of 52
$3,700
4

Beds

3.0

Baths

2,909

Sq.Ft.

15537 MANGO ISLE STREET

Winter Garden, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 16887 WINGSPREAD LOOP Winter Garden, FL MLS# O6389628
  • Recently Listed with Virtual Tour
1 of 38
$7,500
6

Beds

4.0

Baths

3,906

Sq.Ft.

16887 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 876 LANDRUM DRIVE Winter Garden, FL MLS# O6389043
  • Recently Listed with Virtual Tour
1 of 20
$5,500
3

Beds

3.1

Baths

2,289

Sq.Ft.

876 LANDRUM DRIVE

Winter Garden, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 15585 GENTLE RAIN DRIVE Winter Garden, FL MLS# O6389221
$3,500
4

Beds

3.0

Baths

2,200

Sq.Ft.

15585 GENTLE RAIN DRIVE

Winter Garden, FL

Courtesy of SELECTA REALTY LLC
View 15489 HAMLIN PARK DRIVE Winter Garden, FL MLS# O6390003
$3,150
3

Beds

3.1

Baths

2,072

Sq.Ft.

15489 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 7618 LOON AVENUE Winter Garden, FL MLS# O6388840
  • Recently Listed with Virtual Tour
1 of 19
$4,300
5

Beds

3.0

Baths

3,295

Sq.Ft.

7618 LOON AVENUE

Winter Garden, FL

Courtesy of REALTY ONE GROUP ESTATES
View 16719 HARPER COVE DRIVE Winter Garden, FL MLS# O6388856
$3,200
4

Beds

3.1

Baths

2,500

Sq.Ft.

16719 HARPER COVE DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17069 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6389218
  • Recently Listed with Virtual Tour
1 of 24
$2,700
3

Beds

2.1

Baths

1,654

Sq.Ft.

17069 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 15113 WHITE WAGTAIL LANE Winter Garden, FL MLS# O6388369
  • Recently Listed with Virtual Tour
1 of 29
$2,975
3

Beds

2.0

Baths

1,765

Sq.Ft.

15113 WHITE WAGTAIL LANE

Winter Garden, FL

Courtesy of MAINFRAME REAL ESTATE
View 16270 MERRY ALLEY Winter Garden, FL MLS# O6386423
  • Recently Listed with Virtual Tour
1 of 34
$2,650
3

Beds

2.1

Baths

1,683

Sq.Ft.

16270 MERRY ALLEY

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 16117 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6388700
  • Recently Listed with Virtual Tour
1 of 19
$2,950
4

Beds

3.1

Baths

2,560

Sq.Ft.

16117 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of U S GLORY REALTY
View 13346 DANIELS LANDING CIRCLE Winter Garden, FL MLS# O6388207
  • Recently Listed with Virtual Tour
1 of 22
$2,150
2

Beds

2.1

Baths

1,151

Sq.Ft.

13346 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 9404 BOLSHOI ALLEY Winter Garden, FL MLS# O6388458
$2,950
3

Beds

2.1

Baths

1,833

Sq.Ft.

9404 BOLSHOI ALLEY

Winter Garden, FL

Courtesy of MANAGER PROP
View 4851 LACEWING DRIVE Winter Garden, FL MLS# O6388491
  • Recently Listed with Virtual Tour
1 of 24
$3,150
4

Beds

2.1

Baths

2,090

Sq.Ft.

4851 LACEWING DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 6919 PASTURELANDS PLACE Winter Garden, FL MLS# O6387726
  • Recently Listed with Virtual Tour
1 of 22
$2,000
2

Beds

2.1

Baths

1,209

Sq.Ft.

6919 PASTURELANDS PLACE

Winter Garden, FL

Courtesy of RENT A FLORIDA HOME
View 16507 OUTTER GROVE ALLEY Winter Garden, FL MLS# O6385049
  • Recently Listed with Virtual Tour
1 of 40
$2,700
3

Beds

2.1

Baths

1,814

Sq.Ft.

16507 OUTTER GROVE ALLEY

Winter Garden, FL

Courtesy of MBR HOMES INTERNATIONAL REALTY 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

914

Estimated median home price

$590,245
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 - 100K4
$100K - 200K12
$200K - 300K87
$300K - 400K77
$400K - 500K149
$500K - 600K153
$600K - 700K108
$700K - 800K92
$800K - 900K69
$900K - 1M58
$1M - Max105

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family621
Townhouse132
Condo124
Commercial10
Rental221
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 3/11/2026)

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 3/12/2026.