View 1112 JUNIPER HAMMOCK COURT Winter Garden, FL MLS# O6388013
$505,000
4

Beds

2.0

Baths

2,545

Sq.Ft.

1112 JUNIPER HAMMOCK COURT

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 12995 Reaves Road Winter Garden, FL MLS# R10962350
$500,000
Studio

Beds

0.0

Baths

12995 Reaves Road

Winter Garden, FL

View 516 S HIGHLAND AVENUE Winter Garden, FL MLS# O6409675
$500,000
3

Beds

2.0

Baths

1,716

Sq.Ft.

516 S HIGHLAND AVENUE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 14543 GOLDEN HARBOR LANE Winter Garden, FL MLS# O6433451
  • Recently Listed with Virtual Tour
1 of 75
$499,999
3

Beds

2.1

Baths

2,039

Sq.Ft.

14543 GOLDEN HARBOR LANE

Winter Garden, FL

View 12427 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# O6413423
$499,990
4

Beds

3.0

Baths

2,200

Sq.Ft.

12427 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

View 1431 VISCAYA COVE BOULEVARD Winter Garden, FL MLS# O6407306
$499,900
4

Beds

3.0

Baths

2,030

Sq.Ft.

1431 VISCAYA COVE BOULEVARD

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 16161 MANGROVE ROAD Winter Garden, FL MLS# O6420311
$499,900
3

Beds

2.1

Baths

2,200

Sq.Ft.

16161 MANGROVE ROAD

Winter Garden, FL

View 2766 BOBCAT CHASE BOULEVARD Winter Garden, FL MLS# O6427751
$499,900
3

Beds

2.1

Baths

1,811

Sq.Ft.

2766 BOBCAT CHASE BOULEVARD

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 6355 ARGENT WOOD DRIVE Winter Garden, FL MLS# O6427512
  • New Construction with Virtual Tour
1 of 27
$499,690
3

Beds

2.1

Baths

1,652

Sq.Ft.

6355 ARGENT WOOD DRIVE

Winter Garden, FL

View 15027 GROVESIDE ROAD Winter Garden, FL MLS# O6398345
  • New Construction with Virtual Tour
1 of 56
$499,630
3

Beds

2.1

Baths

1,846

Sq.Ft.

15027 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 14257 LAGOON COVE LANE Winter Garden, FL MLS# O6375296
$499,000
3

Beds

2.0

Baths

2,365

Sq.Ft.

14257 LAGOON COVE LANE

Winter Garden, FL

View 16613 POINT ROCK DRIVE Winter Garden, FL MLS# R4910718
$499,000
3

Beds

2.0

Baths

1,689

Sq.Ft.

16613 POINT ROCK DRIVE

Winter Garden, FL

View 8012 BLUEJACK OAK DRIVE Winter Garden, FL MLS# FC317938
$499,000
4

Beds

3.1

Baths

2,222

Sq.Ft.

8012 BLUEJACK OAK DRIVE

Winter Garden, FL

Courtesy of Palm Coast - WEICHERT, REALTORS® - Hallmark Properties
View 14280 BRAEMAR STREET Winter Garden, FL MLS# TB8500322
1 of 33
OPEN HOUSE: Saturday 8/22 12:00 PM - 3:00 PM
$499,000
3

Beds

2.1

Baths

1,964

Sq.Ft.

14280 BRAEMAR STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 12253 S BRACCO STREET Winter Garden, FL MLS# S5150840
$499,000
3

Beds

2.1

Baths

1,788

Sq.Ft.

12253 S BRACCO STREET

Winter Garden, FL

View 15039 GROVESIDE ROAD Winter Garden, FL MLS# O6398354
  • New Construction with Virtual Tour
1 of 52
$497,380
3

Beds

2.1

Baths

1,846

Sq.Ft.

15039 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 16105 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6348822
$497,000
4

Beds

3.0

Baths

2,042

Sq.Ft.

16105 WATER SPRING BOULEVARD

Winter Garden, FL

View 15111 GROVESIDE ROAD Winter Garden, FL MLS# O6423268
  • New Construction with Virtual Tour
1 of 5
$495,935
3

Beds

2.1

Baths

1,846

Sq.Ft.

15111 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 9231 GRAND ISLAND WAY Winter Garden, FL MLS# O6405710
$495,000
4

Beds

2.1

Baths

2,060

Sq.Ft.

9231 GRAND ISLAND WAY

Winter Garden, FL

Courtesy of ELITE INTERNATIONAL REALTY INC
View 15806 GEM VIEW ST Winter Garden, FL MLS# C7526682
  • Adult Community with Virtual Tour
1 of 37
$495,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

15806 GEM VIEW ST

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

1,018

Estimated median home price

$611,805
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

Price Count
$0 - 100K 2
$100K - 200K 21
$200K - 300K 89
$300K - 400K 78
$400K - 500K 147
$500K - 600K 164
$600K - 700K 110
$700K - 800K 117
$800K - 900K 108
$900K - 1M 63
$1M - Max 119

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 702
Townhouse 144
Condo 136
Commercial 9
Rental 177
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 8/19/2026)

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 8/19/2026.