View 9240 BRADLEIGH DRIVE Winter Garden, FL MLS# O6421967
$1,025,000
6

Beds

5.1

Baths

4,124

Sq.Ft.

9240 BRADLEIGH DRIVE

Winter Garden, FL

View 1711 AMSEL FALLS PARK TERRACE Winter Garden, FL MLS# G5114517
$1,046,000
5

Beds

4.0

Baths

3,863

Sq.Ft.

1711 AMSEL FALLS PARK TERRACE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 13361 SUNNY RETREAT LANE Winter Garden, FL MLS# O6419110
  • Adult Community with Virtual Tour
1 of 74
$859,900
4

Beds

3.0

Baths

3,172

Sq.Ft.

13361 SUNNY RETREAT LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 14301 WHITE MOSS WAY Winter Garden, FL MLS# G5114391
$934,999
5

Beds

3.1

Baths

4,053

Sq.Ft.

14301 WHITE MOSS WAY

Winter Garden, FL

View 129 S PARK AVENUE 8E Winter Garden, FL MLS# O6420596
$889,000
3

Beds

3.1

Baths

2,030

Sq.Ft.

129 S PARK AVENUE 8E

Winter Garden, FL

Courtesy of BOARDWALK REALTY, LLC
View 15709 SHOREBIRD LANE Winter Garden, FL MLS# O6420325
$849,900
4

Beds

4.0

Baths

2,768

Sq.Ft.

15709 SHOREBIRD LANE

Winter Garden, FL

Courtesy of REALTY ONE GROUP INSPIRATION
View 11277 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6419923
  • New Construction with Virtual Tour
1 of 31
$899,990
4

Beds

3.1

Baths

3,327

Sq.Ft.

11277 HOLLOW BAY DRIVE

Winter Garden, FL

View 11259 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6419946
  • New Construction with Virtual Tour
1 of 68
OPEN HOUSE: Saturday 8/22 10:00 AM - 6:00 PM
$865,000
4

Beds

3.1

Baths

3,327

Sq.Ft.

11259 HOLLOW BAY DRIVE

Winter Garden, FL

View 11827 SHINE VIEW LANE Winter Garden, FL MLS# O6419995
  • New Construction with Virtual Tour
1 of 63
$863,626
5

Beds

4.1

Baths

3,225

Sq.Ft.

11827 SHINE VIEW LANE

Winter Garden, FL

View 11821 SHINE VIEW LANE Winter Garden, FL MLS# O6420002
  • New Construction with Virtual Tour
1 of 77
$840,000
5

Beds

4.0

Baths

2,866

Sq.Ft.

11821 SHINE VIEW LANE

Winter Garden, FL

View 2496 BARONSMEDE COURT Winter Garden, FL MLS# G5114233
$875,000
4

Beds

4.1

Baths

4,184

Sq.Ft.

2496 BARONSMEDE COURT

Winter Garden, FL

View 14711 WINTER STAY DRIVE Winter Garden, FL MLS# O6419471
$850,000
4

Beds

3.0

Baths

2,662

Sq.Ft.

14711 WINTER STAY DRIVE

Winter Garden, FL

View 15031 GUAVA BAY DRIVE Winter Garden, FL MLS# O6421934
$905,000
5

Beds

4.1

Baths

3,958

Sq.Ft.

15031 GUAVA BAY DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 15878 CITRUS GROVE LOOP Winter Garden, FL MLS# O6418239
$910,000
5

Beds

4.0

Baths

3,505

Sq.Ft.

15878 CITRUS GROVE LOOP

Winter Garden, FL

View 14312 SUNBRIDGE CIRCLE Winter Garden, FL MLS# O6414430
$1,060,000
5

Beds

4.0

Baths

4,225

Sq.Ft.

14312 SUNBRIDGE CIRCLE

Winter Garden, FL

View 806 JOHNS POINT DRIVE Winter Garden, FL MLS# O6418276
$1,075,000
4

Beds

4.1

Baths

3,552

Sq.Ft.

806 JOHNS POINT DRIVE

Winter Garden, FL

View 13092 SUNRISE HARVEST DRIVE Winter Garden, FL MLS# O6417386
$850,000
4

Beds

3.1

Baths

2,993

Sq.Ft.

13092 SUNRISE HARVEST DRIVE

Winter Garden, FL

View 15037 LAKE BESSIE LOOP Winter Garden, FL MLS# O6418541
$1,045,000
7

Beds

4.0

Baths

3,938

Sq.Ft.

15037 LAKE BESSIE LOOP

Winter Garden, FL

View 17242 LAKE STAR ROAD Winter Garden, FL MLS# O6419512
$975,000
4

Beds

3.1

Baths

3,101

Sq.Ft.

17242 LAKE STAR ROAD

Winter Garden, FL

View 17139 INGRAM BLUFF DRIVE Winter Garden, FL MLS# G5113974
$823,309
6

Beds

4.1

Baths

3,412

Sq.Ft.

17139 INGRAM BLUFF 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 8/22/2026.