View 16587 BARBOURS CREEK WAY Winter Garden, FL MLS# O6371746
  • Recently Listed with Virtual Tour
1 of 14
OPEN HOUSE: Saturday 1/10 10:00 AM - 5:00 PM
$416,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16587 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 17082 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6371175
$618,999
4

Beds

3.1

Baths

2,298

Sq.Ft.

17082 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 15497 W STONEYBROOK W PARKWAY Winter Garden, FL MLS# S5141114
$275,000

15497 W STONEYBROOK W PARKWAY

Winter Garden, FL

Courtesy of HOLDING GOLDEN REAL ESTATE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15105 TEA TREE DRIVE Winter Garden, FL MLS# G5106227
  • New Construction
1 of 2
$665,585
4

Beds

2.1

Baths

2,235

Sq.Ft.

15105 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 4360 OLD SYCAMORE Winter Garden, FL MLS# O6370948
  • Recently Listed with Virtual Tour
1 of 66
OPEN HOUSE: Sunday 1/11 12:00 PM - 4:00 PM
$625,000
4

Beds

3.0

Baths

2,548

Sq.Ft.

4360 OLD SYCAMORE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 92 WINDTREE LANE 201 Winter Garden, FL MLS# O6371247
  • Recently Listed with Virtual Tour
1 of 8
$218,000
2

Beds

2.0

Baths

918

Sq.Ft.

92 WINDTREE LANE 201

Winter Garden, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 15345 HAMLIN PARK DRIVE Winter Garden, FL MLS# TB8461483
  • Recently Listed with Virtual Tour
1 of 49
OPEN HOUSE: Saturday 1/10 1:00 PM - 4:00 PM
$529,990
3

Beds

3.1

Baths

2,072

Sq.Ft.

15345 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View Address not provided Winter Garden, FL MLS# G5106258
  • Recently Listed
1 of 28
$599,990
3

Beds

3.0

Baths

2,083

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1329 BROKEN OAK DRIVE 51A Winter Garden, FL MLS# O6370498
  • Recently Listed with Virtual Tour
1 of 32
$300,000
2

Beds

2.0

Baths

1,216

Sq.Ft.

1329 BROKEN OAK DRIVE 51A

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 16276 MERRY ALLEY Winter Garden, FL MLS# O6371565
  • Recently Listed with Virtual Tour
1 of 28
$491,490
4

Beds

2.1

Baths

1,770

Sq.Ft.

16276 MERRY ALLEY

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 16300 MERRY ALLEY Winter Garden, FL MLS# O6371576
  • Recently Listed with Virtual Tour
1 of 28
$546,390
3

Beds

2.1

Baths

1,770

Sq.Ft.

16300 MERRY ALLEY

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 16304 BRIGHT LEAF ROAD Winter Garden, FL MLS# O6371581
  • Recently Listed with Virtual Tour
1 of 28
$521,490
4

Beds

2.1

Baths

1,770

Sq.Ft.

16304 BRIGHT LEAF ROAD

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 16294 MERRY ALLEY Winter Garden, FL MLS# O6371592
  • Recently Listed with Virtual Tour
1 of 22
$492,090
3

Beds

2.1

Baths

1,553

Sq.Ft.

16294 MERRY ALLEY

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 16288 MERRY ALLEY Winter Garden, FL MLS# O6371596
  • Recently Listed with Virtual Tour
1 of 22
$488,590
3

Beds

2.1

Baths

1,553

Sq.Ft.

16288 MERRY ALLEY

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 634 BURCH AVENUE Winter Garden, FL MLS# O6371342
  • Recently Listed
1 of 43
OPEN HOUSE: Saturday 1/10 11:00 AM - 1:00 PM
$650,000
4

Beds

3.1

Baths

2,351

Sq.Ft.

634 BURCH AVENUE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 1474 JUNIPER HAMMOCK STREET Winter Garden, FL MLS# O6369501
  • Recently Listed with Virtual Tour
1 of 50
$675,000
5

Beds

4.0

Baths

3,141

Sq.Ft.

1474 JUNIPER HAMMOCK STREET

Winter Garden, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 14501 GROVE RESORT AVENUE 1727 Winter Garden, FL MLS# O6370138
  • Recently Listed with Virtual Tour
1 of 27
$299,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1727

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 14501 GROVE RESORT AVENUE 3228 Winter Garden, FL MLS# O6370847
  • Recently Listed with Virtual Tour
1 of 27
$240,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 3228

Winter Garden, FL

Courtesy of REAL TERRA GROUP, LLC
View 1362 AVALON ROAD Winter Garden, FL MLS# O6368800
  • Recently Listed with Virtual Tour
1 of 18
$165,000
Studio

Beds

0.0

Baths

1362 AVALON ROAD

Winter Garden, FL

Courtesy of YASMINE KHRINO
View 10624 WORDS DRIVE Winter Garden, FL MLS# O6370851
  • Recently Listed with Virtual Tour
1 of 8
$460,000
4

Beds

2.1

Baths

1,992

Sq.Ft.

10624 WORDS DRIVE

Winter Garden, FL

Courtesy of SALVAMERICA, 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

763

Estimated median home price

$585,000
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

Price Count
$0 - 100K 6
$100K - 200K 10
$200K - 300K 64
$300K - 400K 80
$400K - 500K 135
$500K - 600K 115
$600K - 700K 82
$700K - 800K 70
$800K - 900K 62
$900K - 1M 48
$1M - Max 91

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 491
Townhouse 119
Condo 107
Commercial 9
Rental 223
Lots and Land 33
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 1
Farms 0

(Data as of 1/6/2026)

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 information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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 1/7/2026.

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 1/7/2026.