View 8289 TOPSAIL PLACE Winter Garden, FL MLS# S5151179
$890,000
4

Beds

4.0

Baths

2,755

Sq.Ft.

8289 TOPSAIL PLACE

Winter Garden, FL

View 6100 CYPRESS HILL ROAD Winter Garden, FL MLS# O6412033
$875,000
5

Beds

3.0

Baths

3,777

Sq.Ft.

6100 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of DALTON WADE INC
View 13822 JOMATT LOOP Winter Garden, FL MLS# O6411926
$975,000
4

Beds

3.1

Baths

3,828

Sq.Ft.

13822 JOMATT LOOP

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 16379 SILVER GROVE BOULEVARD Winter Garden, FL MLS# O6411552
$924,900
5

Beds

4.1

Baths

3,823

Sq.Ft.

16379 SILVER GROVE BOULEVARD

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 16104 SANDHILL ROAD Winter Garden, FL MLS# O6411589
$1,020,000
3

Beds

2.0

Baths

1,364

Sq.Ft.

16104 SANDHILL ROAD

Winter Garden, FL

View 13978 LANYARD WAY Winter Garden, FL MLS# O6411513
$879,900
5

Beds

4.0

Baths

3,687

Sq.Ft.

13978 LANYARD WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 13181 TOOLCROSS WAY Winter Garden, FL MLS# O6410984
$999,000
5

Beds

4.0

Baths

3,894

Sq.Ft.

13181 TOOLCROSS WAY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 15652 GENTLE RAIN DRIVE Winter Garden, FL MLS# O6412120
$849,000
5

Beds

4.1

Baths

3,657

Sq.Ft.

15652 GENTLE RAIN DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 10264 LOVE STORY STREET Winter Garden, FL MLS# O6409005
$875,000
5

Beds

3.0

Baths

3,295

Sq.Ft.

10264 LOVE STORY STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 13613 LARSEN LANE Winter Garden, FL MLS# O6410121
$825,000
5

Beds

4.0

Baths

3,812

Sq.Ft.

13613 LARSEN LANE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 907 EASLEY AVENUE Winter Garden, FL MLS# O6406147
$859,000
3

Beds

2.1

Baths

2,252

Sq.Ft.

907 EASLEY AVENUE

Winter Garden, FL

View 15136 TEA TREE DRIVE Winter Garden, FL MLS# G5112230
  • New Construction with Virtual Tour
1 of 58
OPEN HOUSE: Sunday 8/23 1:00 PM - 5:00 PM
$949,990
5

Beds

4.1

Baths

3,692

Sq.Ft.

15136 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8801 FOUNTAIN PALM ALLEY Winter Garden, FL MLS# O6406952
$875,700
4

Beds

3.1

Baths

2,671

Sq.Ft.

8801 FOUNTAIN PALM ALLEY

Winter Garden, FL

View 10103 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6407394
$965,000
5

Beds

3.1

Baths

4,305

Sq.Ft.

10103 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of AMERICA REAL ESTATE COMPANY LL
View 11265 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405351
  • New Construction with Virtual Tour
1 of 7
$850,000
5

Beds

4.1

Baths

3,225

Sq.Ft.

11265 HOLLOW BAY DRIVE

Winter Garden, FL

View 403 WINTER GROVE BOULEVARD Winter Garden, FL MLS# O6405130
  • New Construction with Virtual Tour
1 of 39
$989,961
5

Beds

3.1

Baths

2,681

Sq.Ft.

403 WINTER GROVE BOULEVARD

Winter Garden, FL

View 13780 FRESH IVY STREET Winter Garden, FL MLS# O6403387
  • Adult Community with Virtual Tour
1 of 51
$849,000
4

Beds

3.0

Baths

2,862

Sq.Ft.

13780 FRESH IVY STREET

Winter Garden, FL

View 15078 CANOPY COVER DRIVE Winter Garden, FL MLS# O6404208
  • Adult Community with Virtual Tour
1 of 35
$969,000
3

Beds

2.1

Baths

2,270

Sq.Ft.

15078 CANOPY COVER DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 5150 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6404827
$950,000
5

Beds

4.1

Baths

3,461

Sq.Ft.

5150 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 17085 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5111738
$939,880
5

Beds

4.1

Baths

3,409

Sq.Ft.

17085 HAGGERTY HOLLOW DRIVE

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

1,017

Estimated median home price

$612,000
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 - 100K2
$100K - 200K21
$200K - 300K86
$300K - 400K77
$400K - 500K152
$500K - 600K162
$600K - 700K114
$700K - 800K112
$800K - 900K107
$900K - 1M64
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family701
Townhouse146
Condo132
Commercial9
Rental180
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/22/2026)

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 8/23/2026.