View 12469 WESTFIELD LAKES CIRCLE Winter Garden, FL MLS# O6409038
  • Recently Listed with Virtual Tour
1 of 72
$1,039,000
5

Beds

4.0

Baths

3,451

Sq.Ft.

12469 WESTFIELD LAKES CIRCLE

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY
View 10264 LOVE STORY STREET Winter Garden, FL MLS# O6409005
$900,000
5

Beds

3.0

Baths

3,295

Sq.Ft.

10264 LOVE STORY STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 17100 BEACHGRASS Winter Garden, FL MLS# O6407707
  • Recently Listed with Virtual Tour
1 of 33
$834,990
4

Beds

3.1

Baths

2,781

Sq.Ft.

17100 BEACHGRASS

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 16323 BRIGHT LEAF ROAD Winter Garden, FL MLS# O6407909
  • Recently Listed with Virtual Tour
1 of 38
$998,000
5

Beds

4.1

Baths

3,676

Sq.Ft.

16323 BRIGHT LEAF ROAD

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 907 EASLEY AVENUE Winter Garden, FL MLS# O6406147
  • Recently Listed
1 of 67
$865,000
3

Beds

2.1

Baths

2,252

Sq.Ft.

907 EASLEY AVENUE

Winter Garden, FL

Courtesy of BHHS FLORIDA REALTY
View 14359 MAGNOLIA RIDGE LOOP Winter Garden, FL MLS# O6408165
  • Recently Listed with Virtual Tour
1 of 19
$1,018,000
5

Beds

3.1

Baths

3,881

Sq.Ft.

14359 MAGNOLIA RIDGE LOOP

Winter Garden, FL

Courtesy of BAMYOU REALTY
View 15130 TEA TREE DRIVE Winter Garden, FL MLS# G5112226
$926,582
4

Beds

3.0

Baths

2,740

Sq.Ft.

15130 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15136 TEA TREE DRIVE Winter Garden, FL MLS# G5112230
  • Recently Listed with Virtual Tour
1 of 58
$959,647
6

Beds

4.1

Baths

3,543

Sq.Ft.

15136 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8801 FOUNTAIN PALM ALLEY Winter Garden, FL MLS# O6406952
  • Recently Listed with Virtual Tour
1 of 69
$899,000
4

Beds

3.1

Baths

2,671

Sq.Ft.

8801 FOUNTAIN PALM ALLEY

Winter Garden, FL

Courtesy of LAKEFIELD REALTY GROUP LLC
View 10103 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6407394
  • Recently Listed with Virtual Tour
1 of 14
$970,000
5

Beds

3.1

Baths

4,305

Sq.Ft.

10103 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of AMERICA REAL ESTATE COMPANY LL
View 15232 FIRELIGHT DRIVE Winter Garden, FL MLS# O6408025
  • Recently Listed with Virtual Tour
1 of 64
$829,000
7

Beds

4.0

Baths

4,612

Sq.Ft.

15232 FIRELIGHT DRIVE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 897 LANDRUM DRIVE Winter Garden, FL MLS# O6404632
  • Recently Listed with Virtual Tour
1 of 33
$899,900
4

Beds

3.1

Baths

3,012

Sq.Ft.

897 LANDRUM DRIVE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 11265 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405351
  • New Construction with Virtual Tour
1 of 7
$870,331
5

Beds

4.1

Baths

3,225

Sq.Ft.

11265 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 12463 WESTFIELD LAKES CIRCLE Winter Garden, FL MLS# O6403631
$935,000
4

Beds

3.0

Baths

3,021

Sq.Ft.

12463 WESTFIELD LAKES CIRCLE

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY
View 11283 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405091
  • Recently Listed with Virtual Tour
1 of 7
$909,466
5

Beds

4.1

Baths

3,225

Sq.Ft.

11283 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 403 WINTER GROVE BOULEVARD Winter Garden, FL MLS# O6405130
  • Recently Listed with Virtual Tour
1 of 39
$999,961
5

Beds

3.1

Baths

2,681

Sq.Ft.

403 WINTER GROVE BOULEVARD

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 11253 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405126
  • Recently Listed with Virtual Tour
1 of 18
$819,106
4

Beds

3.0

Baths

2,113

Sq.Ft.

11253 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 13780 FRESH IVY STREET Winter Garden, FL MLS# O6403387
  • Recently Listed with Virtual Tour
1 of 50
$939,900
4

Beds

3.0

Baths

2,862

Sq.Ft.

13780 FRESH IVY STREET

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 15078 CANOPY COVER DRIVE Winter Garden, FL MLS# O6404208
  • Recently Listed with Virtual Tour
1 of 35
$975,000
3

Beds

2.1

Baths

2,270

Sq.Ft.

15078 CANOPY COVER DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 5150 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6404827
  • Recently Listed with Virtual Tour
1 of 42
$995,000
5

Beds

4.1

Baths

3,461

Sq.Ft.

5150 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MS LAND & BUILDING 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

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 - 200K22
$200K - 300K100
$300K - 400K80
$400K - 500K140
$500K - 600K165
$600K - 700K128
$700K - 800K120
$800K - 900K85
$900K - 1M76
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family712
Townhouse139
Condo144
Commercial10
Rental214
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/20/2026)

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 5/21/2026.