View 8801 FOUNTAIN PALM ALLEY Winter Garden, FL MLS# O6406952
$875,700
4

Beds

3.1

Baths

2,671

Sq.Ft.

8801 FOUNTAIN PALM ALLEY

Winter Garden, FL

View 7922 WINTER WREN STREET Winter Garden, FL MLS# O6406681
$765,900
4

Beds

3.1

Baths

3,391

Sq.Ft.

7922 WINTER WREN STREET

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View 10103 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6407394
$965,000
5

Beds

3.1

Baths

4,305

Sq.Ft.

10103 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of AMERICA REAL ESTATE COMPANY LL
The time to sell is now! THE TIME TO SELL IS NOW!
View 11265 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405351
  • New Construction with Virtual Tour
1 of 7
OPEN HOUSE: Sunday 7/26 12:00 PM - 6:00 PM
$871,831
5

Beds

4.1

Baths

3,225

Sq.Ft.

11265 HOLLOW BAY DRIVE

Winter Garden, FL

View 13410 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5112004
  • New Construction with Virtual Tour
1 of 26
$794,990
5

Beds

3.1

Baths

3,076

Sq.Ft.

13410 PEACEFUL MELODY DRIVE

Winter Garden, FL

View 11283 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405091
  • New Construction with Virtual Tour
1 of 7
$909,466
5

Beds

4.1

Baths

3,225

Sq.Ft.

11283 HOLLOW BAY DRIVE

Winter Garden, FL

View 403 WINTER GROVE BOULEVARD Winter Garden, FL MLS# O6405130
  • New Construction with Virtual Tour
1 of 39
$999,961
5

Beds

3.1

Baths

2,681

Sq.Ft.

403 WINTER GROVE BOULEVARD

Winter Garden, FL

View 11253 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405126
  • New Construction with Virtual Tour
1 of 18
$799,990
4

Beds

3.0

Baths

2,113

Sq.Ft.

11253 HOLLOW BAY DRIVE

Winter Garden, FL

View 13780 FRESH IVY STREET Winter Garden, FL MLS# O6403387
  • Adult Community with Virtual Tour
1 of 51
$849,000
4

Beds

3.0

Baths

2,862

Sq.Ft.

13780 FRESH IVY STREET

Winter Garden, FL

View 931 KYLEE ALLEY Winter Garden, FL MLS# O6404673
$766,000
4

Beds

4.0

Baths

2,831

Sq.Ft.

931 KYLEE ALLEY

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 15078 CANOPY COVER DRIVE Winter Garden, FL MLS# O6404208
  • Adult Community with Virtual Tour
1 of 35
$969,000
3

Beds

2.1

Baths

2,270

Sq.Ft.

15078 CANOPY COVER DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 8325 TOPSAIL PLACE Winter Garden, FL MLS# O6404553
$780,000
3

Beds

2.0

Baths

2,170

Sq.Ft.

8325 TOPSAIL PLACE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 5150 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6404827
$950,000
5

Beds

4.1

Baths

3,461

Sq.Ft.

5150 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 11271 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6403252
  • New Construction with Virtual Tour
1 of 7
$869,996
5

Beds

4.0

Baths

2,866

Sq.Ft.

11271 HOLLOW BAY DRIVE

Winter Garden, FL

View 17085 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5111738
$939,880
5

Beds

4.1

Baths

3,409

Sq.Ft.

17085 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

View 461 GERANIUM PARK WAY Winter Garden, FL MLS# O6403758
$875,000
3

Beds

3.1

Baths

2,432

Sq.Ft.

461 GERANIUM PARK WAY

Winter Garden, FL

View 10174 MERRYMEETING BAY DRIVE Winter Garden, FL MLS# O6402434
$974,000
4

Beds

3.1

Baths

2,758

Sq.Ft.

10174 MERRYMEETING BAY DRIVE

Winter Garden, FL

View 17406 HONEYBELL TANGELO COURT Winter Garden, FL MLS# O6402286
  • New Construction with Virtual Tour
1 of 71
OPEN HOUSE: Sunday 7/26 12:00 PM - 6:00 PM
$845,000
5

Beds

4.1

Baths

3,427

Sq.Ft.

17406 HONEYBELL TANGELO COURT

Winter Garden, FL

View 9942 SUMMERLAKE GROVES STREET Winter Garden, FL MLS# O6402319
$879,000
4

Beds

3.1

Baths

2,935

Sq.Ft.

9942 SUMMERLAKE GROVES STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 925 BAINBRIDGE LOOP Winter Garden, FL MLS# O6402075
$815,000
4

Beds

4.0

Baths

3,580

Sq.Ft.

925 BAINBRIDGE LOOP

Winter Garden, FL

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

1,075

Estimated median home price

$615,000
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 - 200K23
$200K - 300K95
$300K - 400K67
$400K - 500K156
$500K - 600K185
$600K - 700K114
$700K - 800K129
$800K - 900K104
$900K - 1M66
$1M - Max135

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family762
Townhouse141
Condo139
Commercial10
Rental226
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/26/2026)

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 7/26/2026.