View 14115 FRASIER STREET Winter Garden, FL MLS# O6384087
$3,100
4

Beds

2.1

Baths

2,114

Sq.Ft.

14115 FRASIER STREET

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 9743 AMBER CHESTNUT WAY Winter Garden, FL MLS# S5144307
$2,880
4

Beds

2.1

Baths

1,948

Sq.Ft.

9743 AMBER CHESTNUT WAY

Winter Garden, FL

Courtesy of SIGNATURE INTERNATIONAL REAL E
View 12144 STONELEIGH ALLEY Winter Garden, FL MLS# O6384252
$2,600
3

Beds

2.0

Baths

1,588

Sq.Ft.

12144 STONELEIGH ALLEY

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
The time to sell is now! THE TIME TO SELL IS NOW!
View 1018 SPRING LANDING DRIVE Winter Garden, FL MLS# O6383916
$2,700
3

Beds

2.0

Baths

1,538

Sq.Ft.

1018 SPRING LANDING DRIVE

Winter Garden, FL

Courtesy of BLUE CANVAS REALTY LLC
View 15517 BAY BRIDGE STREET Winter Garden, FL MLS# O6384051
  • New Construction with Virtual Tour
1 of 27
$2,900
3

Beds

2.1

Baths

1,691

Sq.Ft.

15517 BAY BRIDGE STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 336 E PLANT STREET Winter Garden, FL MLS# O6381842
$784
1,232

Sq.Ft.

336 E PLANT STREET

Winter Garden, FL

Courtesy of WINTER GARDEN REAL ESTATE
View 10360 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6383063
$2,800
3

Beds

2.1

Baths

2,204

Sq.Ft.

10360 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 9014 SONOMA COAST DRIVE Winter Garden, FL MLS# O6383077
$4,200
4

Beds

4.1

Baths

3,426

Sq.Ft.

9014 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P
View 9377 MEADOW HUNT WAY Winter Garden, FL MLS# O6382869
$2,850
4

Beds

2.1

Baths

2,072

Sq.Ft.

9377 MEADOW HUNT WAY

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 16348 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# S5143913
$2,560
3

Beds

2.1

Baths

1,626

Sq.Ft.

16348 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of ACKLEY FLORIDA PROPERTY MANAGEMENT INC
View 9588 JACQUES ALLEY Winter Garden, FL MLS# O6382573
  • New Construction with Virtual Tour
1 of 17
$3,050
3

Beds

2.1

Baths

2,014

Sq.Ft.

9588 JACQUES ALLEY

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
View 1519 PRIORY CIRCLE Winter Garden, FL MLS# O6382465
$2,950
3

Beds

2.1

Baths

1,956

Sq.Ft.

1519 PRIORY CIRCLE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 10284 ATWATER BAY DRIVE Winter Garden, FL MLS# O6382148
$3,250
4

Beds

3.0

Baths

2,300

Sq.Ft.

10284 ATWATER BAY DRIVE

Winter Garden, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View Address not provided Winter Garden, FL MLS# O6382298
$2,900
3

Beds

2.1

Baths

1,848

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of CONDOMINIUM MARKETING LLC
View 14311 BRAEMAR STREET Winter Garden, FL MLS# O6382360
$3,000
4

Beds

2.1

Baths

2,011

Sq.Ft.

14311 BRAEMAR STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 11876 SHINE VIEW LANE Winter Garden, FL MLS# O6381325
  • New Construction with Virtual Tour
1 of 51
$3,600
4

Beds

3.1

Baths

2,496

Sq.Ft.

11876 SHINE VIEW LANE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 7000 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6381796
$2,900
4

Beds

3.1

Baths

1,914

Sq.Ft.

7000 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 15704 MARINA BAY DRIVE Winter Garden, FL MLS# O6380878
$11,500
5

Beds

5.1

Baths

5,005

Sq.Ft.

15704 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of DOUBLE M GROUP COMPANY
View 12893 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6381091
  • New Construction with Virtual Tour
1 of 57
$4,400
5

Beds

4.1

Baths

3,165

Sq.Ft.

12893 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of JC FLORIDA REALTY LLC
View 16246 MERRY ALLEY Winter Garden, FL MLS# O6381155
  • New Construction with Virtual Tour
1 of 41
$2,650
3

Beds

2.1

Baths

1,683

Sq.Ft.

16246 MERRY ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III

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

941

Estimated median home price

$588,900
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 - 100K4
$100K - 200K12
$200K - 300K92
$300K - 400K79
$400K - 500K153
$500K - 600K160
$600K - 700K111
$700K - 800K91
$800K - 900K74
$900K - 1M60
$1M - Max105

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family644
Townhouse135
Condo126
Commercial11
Rental229
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 3/18/2026)

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 3/19/2026.