View 5513 THOMAS SQUARE DRIVE Winter Garden, FL MLS# O6428640
$1,250,000
4

Beds

3.1

Baths

3,941

Sq.Ft.

5513 THOMAS SQUARE DRIVE

Winter Garden, FL

Courtesy of SERHANT
View 16795 TURTLE HATCH DRIVE Winter Garden, FL MLS# O6438512
  • Recently Listed with Virtual Tour
1 of 90
$1,249,990
5

Beds

5.0

Baths

3,615

Sq.Ft.

16795 TURTLE HATCH DRIVE

Winter Garden, FL

Courtesy of LIVE MVRK LLC
View 13217 TOLLCROSS WAY Winter Garden, FL MLS# O6285385
  • New Construction
1 of 78
$1,249,000
6

Beds

5.0

Baths

4,152

Sq.Ft.

13217 TOLLCROSS WAY

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 706 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6394059
$1,225,000
5

Beds

5.2

Baths

4,019

Sq.Ft.

706 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 15594 SHOREBIRD LANE Winter Garden, FL MLS# S5147208
$1,219,000
4

Beds

3.1

Baths

3,022

Sq.Ft.

15594 SHOREBIRD LANE

Winter Garden, FL

View 205 SURPRISE DRIVE Winter Garden, FL MLS# O6365188
  • Virtual Tour
1 of 32
$1,200,000
4

Beds

2.1

Baths

2,171

Sq.Ft.

205 SURPRISE DRIVE

Winter Garden, FL

View 1812 LAKE ROBERTS LANDING DRIVE Winter Garden, FL MLS# O6415935
$1,200,000
6

Beds

4.0

Baths

4,247

Sq.Ft.

1812 LAKE ROBERTS LANDING DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 9969 LOST CREEK DRIVE Winter Garden, FL MLS# O6419414
$1,199,000
5

Beds

3.1

Baths

3,910

Sq.Ft.

9969 LOST CREEK DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 14567 CEDAR HILL DRIVE Winter Garden, FL MLS# O6430207
  • Recently Listed with Virtual Tour
1 of 73
OPEN HOUSE: Sunday 9/6 12:00 PM - 4:00 PM
$1,199,000
5

Beds

3.1

Baths

4,909

Sq.Ft.

14567 CEDAR HILL DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 9189 BUSACO PARK WAY Winter Garden, FL MLS# O6410698
$1,198,000
4

Beds

4.0

Baths

3,424

Sq.Ft.

9189 BUSACO PARK WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 844 OAKLAND PARK BOULEVARD Winter Garden, FL MLS# O6419976
$1,195,000
5

Beds

4.0

Baths

3,525

Sq.Ft.

844 OAKLAND PARK BOULEVARD

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 15686 PANTHER LAKE DRIVE Winter Garden, FL MLS# O6390015
$1,190,000
4

Beds

3.2

Baths

3,094

Sq.Ft.

15686 PANTHER LAKE DRIVE

Winter Garden, FL

View 17588 LAKE STAR ROAD Winter Garden, FL MLS# O6387269
$1,185,000
5

Beds

4.0

Baths

4,026

Sq.Ft.

17588 LAKE STAR ROAD

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 8222 TOPSAIL PLACE Winter Garden, FL MLS# O6430527
  • Virtual Tour
1 of 52
$1,170,000
5

Beds

4.1

Baths

4,199

Sq.Ft.

8222 TOPSAIL PLACE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 10198 MERRYMEETING BAY DRIVE Winter Garden, FL MLS# O6421817
$1,160,000
5

Beds

3.1

Baths

3,911

Sq.Ft.

10198 MERRYMEETING BAY DRIVE

Winter Garden, FL

View 16753 TURTLE HATCH DRIVE Winter Garden, FL MLS# O6438081
  • Recently Listed with Virtual Tour
1 of 49
$1,159,000
4

Beds

3.1

Baths

2,954

Sq.Ft.

16753 TURTLE HATCH DRIVE

Winter Garden, FL

View 650 MEDORA WAY Winter Garden, FL MLS# O6431624
  • New Construction with Virtual Tour
1 of 12
$1,157,190
4

Beds

3.0

Baths

2,902

Sq.Ft.

650 MEDORA WAY

Winter Garden, FL

Courtesy of DAVILA HOMES
View 16071 BARKLY RIDGE COURT Winter Garden, FL MLS# O6390569
$1,150,000
4

Beds

3.0

Baths

2,986

Sq.Ft.

16071 BARKLY RIDGE COURT

Winter Garden, FL

View 9225 HOLLISTON CREEK PLACE Winter Garden, FL MLS# O6427589
$1,150,000
5

Beds

4.0

Baths

3,897

Sq.Ft.

9225 HOLLISTON CREEK PLACE

Winter Garden, FL

View 17425 LAKE INGRAM ROAD Winter Garden, FL MLS# O6397109
$1,149,000
4

Beds

1.1

Baths

2,246

Sq.Ft.

17425 LAKE INGRAM ROAD

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

998

Estimated median home price

$608,500
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 1
$100K - 200K 21
$200K - 300K 89
$300K - 400K 70
$400K - 500K 147
$500K - 600K 167
$600K - 700K 105
$700K - 800K 110
$800K - 900K 112
$900K - 1M 62
$1M - Max 114

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 699
Townhouse 136
Condo 128
Commercial 7
Rental 184
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 1
Farms 0

(Data as of 9/6/2026)

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 9/6/2026.