View 18029 CIDER MILL LANE Winter Garden, FL MLS# O6412471
  • Recently Listed with Virtual Tour
1 of 11
$3,200
4

Beds

3.0

Baths

2,113

Sq.Ft.

18029 CIDER MILL LANE

Winter Garden, FL

Courtesy of INTERNATIONAL NETWORK REALTY
View 15549 GENTLE RAIN DRIVE Winter Garden, FL MLS# O6412697
  • Recently Listed with Virtual Tour
1 of 34
$3,400
4

Beds

3.1

Baths

2,700

Sq.Ft.

15549 GENTLE RAIN DRIVE

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 5917 GRASSY POINT ROAD Winter Garden, FL MLS# O6412321
$3,000
3

Beds

2.1

Baths

1,974

Sq.Ft.

5917 GRASSY POINT ROAD

Winter Garden, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 16414 Grey Pine Dr 0 Winter Garden, FL MLS# A12029172
$3,780
5

Beds

3.0

Baths

16414 Grey Pine Dr 0

Winter Garden, FL

Courtesy of AVANTI WAY REALTY LLC
View 8061 GLENLLOYD AVENUE Winter Garden, FL MLS# O6412372
  • Recently Listed with Virtual Tour
1 of 37
$2,800
3

Beds

2.1

Baths

1,768

Sq.Ft.

8061 GLENLLOYD AVENUE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 14978 LEBEAU LOOP Winter Garden, FL MLS# S5150861
  • Recently Listed with Virtual Tour
1 of 6
$1,800
1

Beds

1.0

Baths

700

Sq.Ft.

14978 LEBEAU LOOP

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 12851 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6412039
  • Recently Listed with Virtual Tour
1 of 32
$3,100
4

Beds

3.0

Baths

1,897

Sq.Ft.

12851 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 2228 GOPHER TORTOISE TERRACE Winter Garden, FL MLS# G5112979
  • Recently Listed with Virtual Tour
1 of 23
$2,450
3

Beds

2.1

Baths

1,620

Sq.Ft.

2228 GOPHER TORTOISE TERRACE

Winter Garden, FL

Courtesy of ASANO REAL ESTATE LLC
View 1954 PANTHEON DRIVE Winter Garden, FL MLS# O6411897
  • Recently Listed with Virtual Tour
1 of 30
$3,150
4

Beds

3.0

Baths

2,027

Sq.Ft.

1954 PANTHEON DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15336 FIRELIGHT DRIVE Winter Garden, FL MLS# G5113086
  • Recently Listed with Virtual Tour
1 of 27
$3,300
4

Beds

3.0

Baths

2,242

Sq.Ft.

15336 FIRELIGHT DRIVE

Winter Garden, FL

Courtesy of BRAZA HOMES
View 9728 NANCY DREW ALLEY Winter Garden, FL MLS# S5150816
  • Recently Listed with Virtual Tour
1 of 13
$3,000
4

Beds

3.1

Baths

2,475

Sq.Ft.

9728 NANCY DREW ALLEY

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 16461 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6412047
  • Recently Listed with Virtual Tour
1 of 58
$2,900
4

Beds

2.1

Baths

1,640

Sq.Ft.

16461 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 7759 GREEN MOUNTAIN WAY Winter Garden, FL MLS# O6411481
$8,000
6

Beds

6.1

Baths

5,174

Sq.Ft.

7759 GREEN MOUNTAIN WAY

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 13341 PONTOON ROAD Winter Garden, FL MLS# S5150810
  • Recently Listed
1 of 22
$2,650
3

Beds

2.1

Baths

1,814

Sq.Ft.

13341 PONTOON ROAD

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 224 FAULKNER STREET Winter Garden, FL MLS# O6411344
$2,865
3

Beds

2.0

Baths

1,591

Sq.Ft.

224 FAULKNER STREET

Winter Garden, FL

Courtesy of WINTER GARDEN REAL ESTATE
View 14156 TITLE WAY Winter Garden, FL MLS# O6403219
$2,850
4

Beds

3.1

Baths

2,475

Sq.Ft.

14156 TITLE WAY

Winter Garden, FL

Courtesy of INTEREALTY SERVICE
View 585 SETTING SUN DRIVE Winter Garden, FL MLS# O6410771
$3,095
4

Beds

3.0

Baths

2,719

Sq.Ft.

585 SETTING SUN DRIVE

Winter Garden, FL

Courtesy of VERANDAH PROPERTIES INC
View 11213 PIXIE MANDARIN CT Winter Garden, FL MLS# O6410949
$4,800
4

Beds

3.1

Baths

3,115

Sq.Ft.

11213 PIXIE MANDARIN CT

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 8115 SAYINGS DRIVE Winter Garden, FL MLS# O6411105
  • Recently Listed with Virtual Tour
1 of 20
$2,900
4

Beds

2.1

Baths

1,992

Sq.Ft.

8115 SAYINGS DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 15236 TRIBUTE OVATION WAY Winter Garden, FL MLS# O6411042
  • Recently Listed with Virtual Tour
1 of 28
$3,250
3

Beds

2.1

Baths

1,850

Sq.Ft.

15236 TRIBUTE OVATION WAY

Winter Garden, FL

Courtesy of DALTON WADE 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

1,037

Estimated median home price

$609,990
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 - 200K25
$200K - 300K92
$300K - 400K80
$400K - 500K140
$500K - 600K172
$600K - 700K129
$700K - 800K113
$800K - 900K89
$900K - 1M71
$1M - Max125

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family718
Townhouse135
Condo143
Commercial10
Rental213
Lots and Land27
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 6/1/2026)

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 6/2/2026.