View 16143 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5107301
$875,595
4

Beds

3.0

Baths

2,740

Sq.Ft.

16143 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17231 MELOGOLD WAY Winter Garden, FL MLS# O6377688
  • Virtual Tour
1 of 50
$969,000
5

Beds

4.1

Baths

3,787

Sq.Ft.

17231 MELOGOLD WAY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 13665 KILLEBREW WAY Winter Garden, FL MLS# O6376754
$935,000
4

Beds

3.1

Baths

3,909

Sq.Ft.

13665 KILLEBREW WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 15391 LEBEAU LOOP Winter Garden, FL MLS# O6375228
  • Virtual Tour
1 of 35
$949,000
4

Beds

3.1

Baths

3,042

Sq.Ft.

15391 LEBEAU LOOP

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14645 SCOTT KEY DRIVE Winter Garden, FL MLS# G5106818
$890,000
4

Beds

3.1

Baths

3,427

Sq.Ft.

14645 SCOTT KEY DRIVE

Winter Garden, FL

Courtesy of RIVA REALTY GROUP LLC
View 17952 LOOKOUT HILL ROAD Winter Garden, FL MLS# O6373477
$899,999
Studio

Beds

0.0

Baths

17952 LOOKOUT HILL ROAD

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 5074 BREEZY ACRES STREET Winter Garden, FL MLS# O6369788
$969,900
7

Beds

4.1

Baths

4,720

Sq.Ft.

5074 BREEZY ACRES STREET

Winter Garden, FL

Courtesy of NEW HEIGHTS REALTY GROUP
View 9207 BUSACO PARK WAY Winter Garden, FL MLS# O6366636
$1,000,000
5

Beds

4.0

Baths

3,291

Sq.Ft.

9207 BUSACO PARK WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 8759 SONOMA COAST DRIVE Winter Garden, FL MLS# S5139789
$1,080,000
5

Beds

5.0

Baths

3,416

Sq.Ft.

8759 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of MBT REALTY LLC
View 14282 CREEKBED CIRCLE Winter Garden, FL MLS# O6365928
$899,900
4

Beds

4.0

Baths

3,479

Sq.Ft.

14282 CREEKBED CIRCLE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 15162 CANOPY COVER DRIVE Winter Garden, FL MLS# S5139203
  • Adult Community with Virtual Tour
1 of 69
$880,000
2

Beds

2.0

Baths

2,049

Sq.Ft.

15162 CANOPY COVER DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 17401 HONEYBELL TANGELO COURT Winter Garden, FL MLS# TB8451532
  • New Construction with Virtual Tour
1 of 57
$954,990
5

Beds

4.1

Baths

3,542

Sq.Ft.

17401 HONEYBELL TANGELO COURT

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 9319 BRADLEIGH DRIVE Winter Garden, FL MLS# O6362694
$995,000
5

Beds

4.1

Baths

3,602

Sq.Ft.

9319 BRADLEIGH DRIVE

Winter Garden, FL

Courtesy of THE PROPERTY STOP LLC
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 15292 MARITIME PINE DRIVE Winter Garden, FL MLS# G5104771
$971,815
4

Beds

3.0

Baths

3,108

Sq.Ft.

15292 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 10067 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6361968
$1,170,000
6

Beds

5.0

Baths

4,305

Sq.Ft.

10067 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 16149 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5104655
$1,005,995
5

Beds

3.1

Baths

3,764

Sq.Ft.

16149 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6529 SHORE JUNIPER STREET Winter Garden, FL MLS# G5104187
$970,460
4

Beds

3.0

Baths

3,108

Sq.Ft.

6529 SHORE JUNIPER STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
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 15166 TEA TREE DRIVE Winter Garden, FL MLS# G5104190
$943,160
4

Beds

3.0

Baths

3,108

Sq.Ft.

15166 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC

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

1,047

Estimated median home price

$615,000
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 1
$100K - 200K 24
$200K - 300K 88
$300K - 400K 80
$400K - 500K 145
$500K - 600K 170
$600K - 700K 129
$700K - 800K 117
$800K - 900K 92
$900K - 1M 72
$1M - Max 129

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 731
Townhouse 139
Condo 137
Commercial 11
Rental 197
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 6/7/2026)

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 6/8/2026.