View 16175 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5104189
$920,308
4

Beds

3.0

Baths

3,108

Sq.Ft.

16175 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1004 VINSETTA CIRCLE Winter Garden, FL MLS# O6359139
  • Virtual Tour
1 of 64
OPEN HOUSE: Sunday 1/11 11:00 AM - 2:00 PM
$918,000
5

Beds

3.2

Baths

4,898

Sq.Ft.

1004 VINSETTA CIRCLE

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 7578 PURPLE FINCH STREET Winter Garden, FL MLS# O6359699
$915,000
5

Beds

4.0

Baths

3,975

Sq.Ft.

7578 PURPLE FINCH STREET

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 11145 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6367437
  • New Construction with Virtual Tour
1 of 31
$914,271
4

Beds

3.2

Baths

3,327

Sq.Ft.

11145 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 11129 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6349552
  • New Construction with Virtual Tour
1 of 31
$914,236
4

Beds

3.1

Baths

3,327

Sq.Ft.

11129 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 13214 DENDY WAY Winter Garden, FL MLS# O6366658
  • New Construction with Virtual Tour
1 of 71
$910,000
5

Beds

4.1

Baths

3,719

Sq.Ft.

13214 DENDY WAY

Winter Garden, FL

Courtesy of KICANTO REALTY
View 16394 TALIESIN STREET Winter Garden, FL MLS# O6371718
  • Recently Listed with Virtual Tour
1 of 53
$910,000
5

Beds

4.1

Baths

3,093

Sq.Ft.

16394 TALIESIN STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15506 HONEY MANDARIN WAY Winter Garden, FL MLS# O6343579
$909,000
5

Beds

4.1

Baths

3,408

Sq.Ft.

15506 HONEY MANDARIN WAY

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
View 15099 TEA TREE DRIVE Winter Garden, FL MLS# G5105171
$908,676
4

Beds

3.1

Baths

2,688

Sq.Ft.

15099 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 515 N BOYD STREET Winter Garden, FL MLS# O6222919
$900,000
5

Beds

4.0

Baths

3,152

Sq.Ft.

515 N BOYD STREET

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 17561 SEIDNER ROAD Winter Garden, FL MLS# G5105438
$900,000
4

Beds

4.0

Baths

2,850

Sq.Ft.

17561 SEIDNER ROAD

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 5074 BREEZY ACRES STREET Winter Garden, FL MLS# O6369788
  • Recently Listed with Virtual Tour
1 of 59
$900,000
7

Beds

4.1

Baths

4,720

Sq.Ft.

5074 BREEZY ACRES STREET

Winter Garden, FL

Courtesy of NEW HEIGHTS REALTY GROUP
View 15213 MARITIME PINE DRIVE Winter Garden, FL MLS# G5102285
$899,360
4

Beds

3.0

Baths

2,879

Sq.Ft.

15213 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 10699 PETRILLO WAY Winter Garden, FL MLS# O6301935
$899,000
5

Beds

4.1

Baths

3,670

Sq.Ft.

10699 PETRILLO WAY

Winter Garden, FL

Courtesy of DOUGLAS ELLIMAN
View 15916 CITRUS KNOLL DRIVE Winter Garden, FL MLS# O6341843
$899,000
5

Beds

3.1

Baths

2,843

Sq.Ft.

15916 CITRUS KNOLL DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 15669 CITRUS HARVEST ROAD Winter Garden, FL MLS# O6346904
  • Virtual Tour
1 of 97
OPEN HOUSE: Saturday 1/10 2:30 PM - 4:30 PM
$899,000
4

Beds

3.1

Baths

3,407

Sq.Ft.

15669 CITRUS HARVEST ROAD

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 13147 FARO COURT Winter Garden, FL MLS# O6360828
$899,000
5

Beds

4.1

Baths

3,719

Sq.Ft.

13147 FARO COURT

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View 5217 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6363382
$899,000
4

Beds

3.1

Baths

3,144

Sq.Ft.

5217 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 16137 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5102317
$895,620
4

Beds

3.0

Baths

2,726

Sq.Ft.

16137 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 4940 PALMETTO PARK DRIVE Winter Garden, FL MLS# O6356578
$895,000
5

Beds

3.1

Baths

4,497

Sq.Ft.

4940 PALMETTO PARK DRIVE

Winter Garden, FL

Courtesy of BHHS FLORIDA REALTY

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

783

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 - 100K6
$100K - 200K11
$200K - 300K67
$300K - 400K78
$400K - 500K138
$500K - 600K117
$600K - 700K89
$700K - 800K71
$800K - 900K68
$900K - 1M48
$1M - Max90

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family504
Townhouse123
Condo111
Commercial9
Rental236
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/9/2026)

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 1/10/2026.