View 14099 LOCHEND WAY Winter Garden, FL MLS# O6404015
$479,900
3

Beds

2.1

Baths

1,720

Sq.Ft.

14099 LOCHEND WAY

Winter Garden, FL

Courtesy of INTERNATIONAL REAL ESTATE LLC
View 12003 HOLYSTONE STREET Winter Garden, FL MLS# L4961121
$445,000
3

Beds

2.1

Baths

1,814

Sq.Ft.

12003 HOLYSTONE STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY SMART
View 16570 BARBOURS CREEK WAY Winter Garden, FL MLS# O6403257
  • New Construction with Virtual Tour
1 of 15
$419,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16570 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1670 E SPRING RIDGE CIRCLE Winter Garden, FL MLS# O6403033
$410,000
3

Beds

2.0

Baths

1,699

Sq.Ft.

1670 E SPRING RIDGE CIRCLE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 15684 ORANGE HARVEST LOOP Winter Garden, FL MLS# W7885221
$459,900
3

Beds

2.1

Baths

2,012

Sq.Ft.

15684 ORANGE HARVEST LOOP

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 837 GRANDE REGAL POINT Winter Garden, FL MLS# O6400571
$450,000
3

Beds

2.0

Baths

1,874

Sq.Ft.

837 GRANDE REGAL POINT

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 2281 OAKINGTON STREET Winter Garden, FL MLS# S5148475
$475,000
3

Beds

2.0

Baths

1,628

Sq.Ft.

2281 OAKINGTON STREET

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 7036 BOLANZO ALLEY Winter Garden, FL MLS# O6401429
$475,000
4

Beds

3.1

Baths

1,920

Sq.Ft.

7036 BOLANZO ALLEY

Winter Garden, FL

Courtesy of SERHANT
View 2478 PRAIRIE VIEW DRIVE Winter Garden, FL MLS# O6400594
$499,900
4

Beds

3.0

Baths

2,766

Sq.Ft.

2478 PRAIRIE VIEW DRIVE

Winter Garden, FL

Courtesy of ENTERA REALTY LLC
View 236 DONALD DRIVE Winter Garden, FL MLS# O6401940
$465,000
2

Beds

1.0

Baths

1,080

Sq.Ft.

236 DONALD DRIVE

Winter Garden, FL

Courtesy of GLOBAL FLORIDA REALTY
View 5618 WATER ROSE ROAD Winter Garden, FL MLS# O6400788
$395,000
3

Beds

2.1

Baths

1,755

Sq.Ft.

5618 WATER ROSE ROAD

Winter Garden, FL

Courtesy of SUNNY 365 REALTY GROUP
View 16749 HARPER COVE DRIVE Winter Garden, FL MLS# O6400511
$499,999
3

Beds

2.1

Baths

2,014

Sq.Ft.

16749 HARPER COVE DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 328 BAYSIDE AVENUE Winter Garden, FL MLS# O6396654
$445,000
3

Beds

2.0

Baths

1,235

Sq.Ft.

328 BAYSIDE AVENUE

Winter Garden, FL

Courtesy of SOUTHERN HERITAGE REALTY, INC
View 18191 CIDER MILL LANE Winter Garden, FL MLS# O6399312
  • New Construction with Virtual Tour
1 of 18
$464,990
3

Beds

2.1

Baths

1,817

Sq.Ft.

18191 CIDER MILL LANE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 8170 BLUEJACK OAK DRIVE Winter Garden, FL MLS# O6399484
  • Virtual Tour
1 of 44
OPEN HOUSE: Saturday 6/6 10:00 AM - 1:00 PM
$460,000
3

Beds

2.1

Baths

1,853

Sq.Ft.

8170 BLUEJACK OAK DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15187 HARROWGATE WAY Winter Garden, FL MLS# TB8497081
$435,000
3

Beds

2.0

Baths

1,296

Sq.Ft.

15187 HARROWGATE WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 15755 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6400420
$420,000
3

Beds

2.1

Baths

1,636

Sq.Ft.

15755 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of REVEL REALTY LLC
View 10031 MEMOIR AVENUE Winter Garden, FL MLS# O6399210
$400,000
3

Beds

2.1

Baths

1,636

Sq.Ft.

10031 MEMOIR AVENUE

Winter Garden, FL

Courtesy of BROKERS REAL ESTATE GROUP INC
View 15907 MARINA BAY DRIVE Winter Garden, FL MLS# O6398406
$443,500
3

Beds

2.1

Baths

1,818

Sq.Ft.

15907 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of SIMPSON REALTY LLC
View 15027 GROVESIDE ROAD Winter Garden, FL MLS# O6398345
  • New Construction with Virtual Tour
1 of 56
$494,630
3

Beds

2.1

Baths

1,846

Sq.Ft.

15027 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP 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

1,052

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 - 200K24
$200K - 300K87
$300K - 400K80
$400K - 500K145
$500K - 600K174
$600K - 700K130
$700K - 800K117
$800K - 900K91
$900K - 1M73
$1M - Max130

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family736
Townhouse138
Condo138
Commercial11
Rental199
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 6/6/2026)

Information deemed reliable but not guaranteed.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 6/6/2026.

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 6/6/2026.