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 17667 LAKE STAR ROAD Winter Garden, FL MLS# TB8521869
  • New Construction with Virtual Tour
1 of 9
$899,741
5

Beds

4.1

Baths

3,545

Sq.Ft.

17667 LAKE STAR ROAD

Winter Garden, FL

View 15031 GUAVA BAY DRIVE Winter Garden, FL MLS# O6421934
  • Recently Listed with Virtual Tour
1 of 36
$905,000
5

Beds

4.1

Baths

3,958

Sq.Ft.

15031 GUAVA BAY DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 17350 WILD DAISY DRIVE Winter Garden, FL MLS# G5113976
$910,510
6

Beds

4.0

Baths

4,236

Sq.Ft.

17350 WILD DAISY DRIVE

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

View 6225 FLOWERING CHERRY BEND DRIVE Winter Garden, FL MLS# G5113896
$846,095
6

Beds

4.1

Baths

3,412

Sq.Ft.

6225 FLOWERING CHERRY BEND DRIVE

Winter Garden, FL

View 12959 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6417449
  • New Construction with Virtual Tour
1 of 13
$750,000
4

Beds

3.1

Baths

2,858

Sq.Ft.

12959 HARVEST RAIN AVENUE

Winter Garden, FL

View 15154 TEA TREE DRIVE Winter Garden, FL MLS# G5113803
$994,733
5

Beds

4.1

Baths

3,839

Sq.Ft.

15154 TEA TREE DRIVE

Winter Garden, FL

View 519 TEAGARDEN COURT Winter Garden, FL MLS# O6416709
$878,000
4

Beds

3.0

Baths

3,061

Sq.Ft.

519 TEAGARDEN COURT

Winter Garden, FL

View 6334 WILD PERSIMMON WAY Winter Garden, FL MLS# G5113852
  • New Construction with Virtual Tour
1 of 49
$913,313
6

Beds

4.1

Baths

3,543

Sq.Ft.

6334 WILD PERSIMMON WAY

Winter Garden, FL

View 13856 GLYNSHEL DRIVE Winter Garden, FL MLS# O6416757
$850,000
5

Beds

4.0

Baths

3,538

Sq.Ft.

13856 GLYNSHEL DRIVE

Winter Garden, FL

View 13404 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5113736
  • New Construction with Virtual Tour
1 of 19
$769,990
4

Beds

3.1

Baths

2,689

Sq.Ft.

13404 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13392 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5113739
  • New Construction with Virtual Tour
1 of 26
$764,990
5

Beds

4.0

Baths

3,076

Sq.Ft.

13392 PEACEFUL MELODY DRIVE

Winter Garden, FL

View 15160 TEA TREE DRIVE Winter Garden, FL MLS# G5113740
  • New Construction with Virtual Tour
1 of 39
$879,806
4

Beds

3.0

Baths

2,740

Sq.Ft.

15160 TEA TREE DRIVE

Winter Garden, FL

View 13086 SUNRISE HARVEST DRIVE Winter Garden, FL MLS# O6415942
  • Virtual Tour
1 of 57
OPEN HOUSE: Sunday 7/19 1:00 PM - 3:00 PM
$849,000
5

Beds

3.1

Baths

2,835

Sq.Ft.

13086 SUNRISE HARVEST DRIVE

Winter Garden, FL

View 6171 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5113609
$792,805
4

Beds

3.1

Baths

2,688

Sq.Ft.

6171 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 402 E MAPLE STREET Winter Garden, FL MLS# O6412747
$900,000
6

Beds

4.2

Baths

2,876

Sq.Ft.

402 E MAPLE STREET

Winter Garden, FL

View 13129 FARO COURT Winter Garden, FL MLS# O6415958
$828,500
5

Beds

4.1

Baths

3,664

Sq.Ft.

13129 FARO COURT

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

918

Estimated median home price

$608,645
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 - 100K1
$100K - 200K22
$200K - 300K93
$300K - 400K62
$400K - 500K130
$500K - 600K148
$600K - 700K97
$700K - 800K105
$800K - 900K86
$900K - 1M59
$1M - Max115

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family619
Townhouse127
Condo139
Commercial11
Rental209
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/18/2026)

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 7/19/2026.