View 15489 HAMLIN PARK DRIVE Winter Garden, FL MLS# O6390003
  • Recently Listed with Virtual Tour
1 of 30
$3,150
3

Beds

3.1

Baths

2,072

Sq.Ft.

15489 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 7738 SUMMERLAKE POINTE BOULEVARD Winter Garden, FL MLS# S5145754
$3,500
4

Beds

3.1

Baths

3,526

Sq.Ft.

7738 SUMMERLAKE POINTE BOULEVARD

Winter Garden, FL

Courtesy of LA ROSA REALTY KISSIMMEE
View 7618 LOON AVENUE Winter Garden, FL MLS# O6388840
$4,300
5

Beds

3.0

Baths

3,295

Sq.Ft.

7618 LOON AVENUE

Winter Garden, FL

Courtesy of REALTY ONE GROUP ESTATES
The time to sell is now! THE TIME TO SELL IS NOW!
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 5945 GLORY BOWER DRIVE Winter Garden, FL MLS# O6380920
  • Recently Listed with Virtual Tour
1 of 30
$2,999
3

Beds

2.1

Baths

2,128

Sq.Ft.

5945 GLORY BOWER DRIVE

Winter Garden, FL

Courtesy of 407 PROPERTIES
View 15113 WHITE WAGTAIL LANE Winter Garden, FL MLS# O6388369
$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
  • New Construction 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
$2,850
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
$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
  • New Construction
1 of 29
$2,950
3

Beds

2.1

Baths

1,833

Sq.Ft.

9404 BOLSHOI ALLEY

Winter Garden, FL

Courtesy of MANAGER PROP
View 6919 PASTURELANDS PLACE Winter Garden, FL MLS# O6387726
$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
$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
View 5106 RAILROAD VINE ALLEY Winter Garden, FL MLS# O6388112
  • New Construction with Virtual Tour
1 of 27
$3,000
4

Beds

2.1

Baths

2,011

Sq.Ft.

5106 RAILROAD VINE ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 11949 BRACCO STREET Winter Garden, FL MLS# O6387696
$2,800
4

Beds

2.1

Baths

2,082

Sq.Ft.

11949 BRACCO STREET

Winter Garden, FL

Courtesy of INTEREALTY SERVICE
View 1021 TEMPLE GROVE PLACE Winter Garden, FL MLS# O6386985
$8,500
4

Beds

4.1

Baths

3,185

Sq.Ft.

1021 TEMPLE GROVE PLACE

Winter Garden, FL

Courtesy of MAINFRAME REAL ESTATE
View 15192 CHAPTER WAY Winter Garden, FL MLS# O6387353
$2,949
4

Beds

3.1

Baths

2,486

Sq.Ft.

15192 CHAPTER WAY

Winter Garden, FL

Courtesy of INTOP PROPERTY MANAGEMENT
View 57 WINDTREE LANE G Winter Garden, FL MLS# O6387462
$1,600
2

Beds

2.0

Baths

918

Sq.Ft.

57 WINDTREE LANE G

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 13157 BOUNTY AVENUE Winter Garden, FL MLS# O6387963
$2,950
3

Beds

2.1

Baths

1,814

Sq.Ft.

13157 BOUNTY AVENUE

Winter Garden, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY
View 15369 HAMLIN PARK DRIVE Winter Garden, FL MLS# O6386622
  • New Construction with Virtual Tour
1 of 26
$3,200
3

Beds

3.1

Baths

2,072

Sq.Ft.

15369 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of PAK HOME REALTY
View 11043 BOOKMARK LANE Winter Garden, FL MLS# O6387242
$2,900
4

Beds

2.1

Baths

1,992

Sq.Ft.

11043 BOOKMARK LANE

Winter Garden, FL

Courtesy of SUNNY 365 REALTY GROUP

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

953

Estimated median home price

$589,000
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 - 100K4
$100K - 200K15
$200K - 300K96
$300K - 400K81
$400K - 500K155
$500K - 600K155
$600K - 700K112
$700K - 800K92
$800K - 900K79
$900K - 1M62
$1M - Max102

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family646
Townhouse144
Condo128
Commercial11
Rental221
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 3/27/2026)

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 3/30/2026.