View 14612 GLADE HILL PARK WAY Winter Garden, FL MLS# S5151295
$5,900
5

Beds

4.1

Baths

3,892

Sq.Ft.

14612 GLADE HILL PARK WAY

Winter Garden, FL

View 14582 OLD THICKET TRACE Winter Garden, FL MLS# O6413688
$4,500
5

Beds

4.0

Baths

3,175

Sq.Ft.

14582 OLD THICKET TRACE

Winter Garden, FL

View 14978 LEBEAU LOOP Winter Garden, FL MLS# S5150861
$1,690
1

Beds

1.0

Baths

700

Sq.Ft.

14978 LEBEAU LOOP

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
The time to sell is now! THE TIME TO SELL IS NOW!
View 7759 GREEN MOUNTAIN WAY Winter Garden, FL MLS# O6411481
$7,500
6

Beds

6.1

Baths

5,174

Sq.Ft.

7759 GREEN MOUNTAIN WAY

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 13341 PONTOON ROAD Winter Garden, FL MLS# S5150810
$2,650
3

Beds

2.1

Baths

1,814

Sq.Ft.

13341 PONTOON ROAD

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15236 TRIBUTE OVATION WAY Winter Garden, FL MLS# O6411042
$3,150
3

Beds

2.1

Baths

1,850

Sq.Ft.

15236 TRIBUTE OVATION WAY

Winter Garden, FL

Courtesy of DALTON WADE INC
View 11056 GREAT ROCK STREET Winter Garden, FL MLS# S5150368
$2,550
3

Beds

2.1

Baths

1,817

Sq.Ft.

11056 GREAT ROCK STREET

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 15212 TRIBUTE OVATION WAY Winter Garden, FL MLS# O6408830
$2,875
3

Beds

2.1

Baths

1,688

Sq.Ft.

15212 TRIBUTE OVATION WAY

Winter Garden, FL

View 8119 LAUGHING GULL STREET Winter Garden, FL MLS# O6408656
$3,300
4

Beds

2.0

Baths

2,043

Sq.Ft.

8119 LAUGHING GULL STREET

Winter Garden, FL

View 18001 PHIL C PETERS ROAD Winter Garden, FL MLS# O6407385
$3,200
3

Beds

2.0

Baths

936

Sq.Ft.

18001 PHIL C PETERS ROAD

Winter Garden, FL

Courtesy of AAA GLOBAL VENTURES PA
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

Courtesy of AGENT TRUST REALTY CORPORATION
View 16347 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# S5149540
$2,550
3

Beds

2.1

Baths

1,793

Sq.Ft.

16347 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

View 143 SOUTHERN PECAN CIRCLE 201 Winter Garden, FL MLS# O6402229
$2,300
3

Beds

2.0

Baths

1,453

Sq.Ft.

143 SOUTHERN PECAN CIRCLE 201

Winter Garden, FL

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 595 9TH STREET Winter Garden, FL MLS# O6398340
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1 of 17
$34,800
1,204

Sq.Ft.

595 9TH STREET

Winter Garden, FL

View 1221 PRIORY CIRCLE Winter Garden, FL MLS# O6397929
$2,600
3

Beds

2.1

Baths

1,675

Sq.Ft.

1221 PRIORY CIRCLE

Winter Garden, FL

View 595 9TH STREET 115 Winter Garden, FL MLS# O6398346
$42,000
1,204

Sq.Ft.

595 9TH STREET 115

Winter Garden, FL

View 16743 HERONGATE DRIVE Winter Garden, FL MLS# O6397844
$2,800
3

Beds

2.0

Baths

1,705

Sq.Ft.

16743 HERONGATE DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 15367 GILLIGAN COURT Winter Garden, FL MLS# O6397119
$3,500
4

Beds

2.1

Baths

2,156

Sq.Ft.

15367 GILLIGAN COURT

Winter Garden, FL

View 9240 WOODCRANE DRIVE Winter Garden, FL MLS# O6396748
$4,799
5

Beds

4.0

Baths

3,760

Sq.Ft.

9240 WOODCRANE 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

1,016

Estimated median home price

$614,995
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 - 300K86
$300K - 400K78
$400K - 500K151
$500K - 600K160
$600K - 700K113
$700K - 800K112
$800K - 900K109
$900K - 1M65
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family700
Townhouse146
Condo133
Commercial9
Rental179
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/24/2026)

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 8/24/2026.