View 203 S MAIN STREET Winter Garden, FL MLS# O6406066
$2,750
2

Beds

2.0

Baths

1,753

Sq.Ft.

203 S MAIN STREET

Winter Garden, FL

View 6385 BREEZE FILLED LANE Winter Garden, FL MLS# O6405945
$2,800
4

Beds

2.1

Baths

1,770

Sq.Ft.

6385 BREEZE FILLED LANE

Winter Garden, FL

View 6678 JUNEBERRY WAY Winter Garden, FL MLS# O6401971
  • New Construction with Virtual Tour
1 of 22
$3,049
3

Beds

3.1

Baths

2,072

Sq.Ft.

6678 JUNEBERRY WAY

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 12899 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6405439
$3,249
3

Beds

2.1

Baths

1,908

Sq.Ft.

12899 WESTHAVEN OAK DRIVE

Winter Garden, FL

View 15205 SHONAN GOLD DRIVE Winter Garden, FL MLS# O6404928
$3,400
3

Beds

3.1

Baths

2,228

Sq.Ft.

15205 SHONAN GOLD DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17741 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6404413
$2,650
3

Beds

2.1

Baths

1,466

Sq.Ft.

17741 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY
View 16236 CARRAWAY BAY ALLEY Winter Garden, FL MLS# S5149719
$3,000
3

Beds

2.0

Baths

1,689

Sq.Ft.

16236 CARRAWAY BAY ALLEY

Winter Garden, FL

Courtesy of MELIN REALTY LLC
View 14488 WHITTRIDGE DRIVE Winter Garden, FL MLS# O6404890
$3,000
4

Beds

3.0

Baths

2,328

Sq.Ft.

14488 WHITTRIDGE DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 14384 BRAEMAR STREET Winter Garden, FL MLS# O6400691
$2,800
3

Beds

2.1

Baths

2,000

Sq.Ft.

14384 BRAEMAR STREET

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 16347 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# S5149540
$2,600
3

Beds

2.1

Baths

1,793

Sq.Ft.

16347 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of DEFINITIVE GROUP LLC
View 2827 SANCTUARY LANE Winter Garden, FL MLS# O6403747
$4,500
3

Beds

2.1

Baths

2,178

Sq.Ft.

2827 SANCTUARY LANE

Winter Garden, FL

Courtesy of GARCIA REALTY GROUP
View 5417 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6403708
$2,600
3

Beds

2.1

Baths

1,506

Sq.Ft.

5417 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 502 S HIGHLAND AVENUE Winter Garden, FL MLS# O6403053
$2,800
3

Beds

1.0

Baths

2,102

Sq.Ft.

502 S HIGHLAND AVENUE

Winter Garden, FL

Courtesy of NEW SOLUTIONS REALTY INC
View 13071 INKWELL ALLEY Winter Garden, FL MLS# S5148709
$2,650
4

Beds

3.0

Baths

2,042

Sq.Ft.

13071 INKWELL ALLEY

Winter Garden, FL

View 17877 PHIL C PETERS RD Winter Garden, FL MLS# O6402176
$4,299
3

Beds

2.0

Baths

2,501

Sq.Ft.

17877 PHIL C PETERS RD

Winter Garden, FL

Courtesy of REIS E SILVA REALTY GROUP LLC
View 143 SOUTHERN PECAN CIRCLE 201 Winter Garden, FL MLS# O6402229
$2,350
3

Beds

2.0

Baths

1,453

Sq.Ft.

143 SOUTHERN PECAN CIRCLE 201

Winter Garden, FL

View 508 VARSITY STREET Winter Garden, FL MLS# O6401722
$1,695
2

Beds

1.0

Baths

780

Sq.Ft.

508 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 13527 DANIELS LANDING CIRCLE Winter Garden, FL MLS# S5148507
$2,300
3

Beds

2.1

Baths

1,365

Sq.Ft.

13527 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of Kissimmee - WEICHERT, REALTORS® - Hallmark Properties
View 16350 HAMLIN VIEW STREET Winter Garden, FL MLS# O6400898
  • New Construction with Virtual Tour
1 of 67
$2,950
3

Beds

2.1

Baths

1,644

Sq.Ft.

16350 HAMLIN VIEW STREET

Winter Garden, FL

Courtesy of WEBB FLORIDA REALTY LLC
View 12506 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# S5148369
$1,600
1

Beds

1.0

Baths

2,900

Sq.Ft.

12506 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC

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

1,065

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

PriceCount
$0 - 100K1
$100K - 200K24
$200K - 300K95
$300K - 400K76
$400K - 500K140
$500K - 600K185
$600K - 700K122
$700K - 800K115
$800K - 900K101
$900K - 1M71
$1M - Max135

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family751
Townhouse132
Condo145
Commercial11
Rental204
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/2/2026)

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 7/3/2026.