View 9368 BOLSHOI ALLEY Winter Garden, FL MLS# O6376868
  • New Construction with Virtual Tour
1 of 28
$2,700
3

Beds

2.1

Baths

1,833

Sq.Ft.

9368 BOLSHOI ALLEY

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 13931 DANIELS LANDING CIRCLE Winter Garden, FL MLS# O6375806
$2,000
2

Beds

2.1

Baths

1,385

Sq.Ft.

13931 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of WENDY MORRIS REALTY
View 10696 WORDS DRIVE Winter Garden, FL MLS# O6375703
$2,890
4

Beds

2.1

Baths

2,000

Sq.Ft.

10696 WORDS DRIVE

Winter Garden, FL

Courtesy of JC FLORIDA REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 14835 OLD THICKET TRACE Winter Garden, FL MLS# O6375317
$3,700
4

Beds

3.1

Baths

2,630

Sq.Ft.

14835 OLD THICKET TRACE

Winter Garden, FL

Courtesy of THE AGENCY FL
View 418 CHARLES STREET Winter Garden, FL MLS# O6375338
$2,600
5

Beds

3.0

Baths

1,584

Sq.Ft.

418 CHARLES STREET

Winter Garden, FL

Courtesy of CANI PROPERTY MANAGEMENT
View 16560 WINGSPREAD LOOP Winter Garden, FL MLS# O6375137
$2,800
3

Beds

2.0

Baths

1,676

Sq.Ft.

16560 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 13890 TITLE WAY Winter Garden, FL MLS# O6372589
$2,950
3

Beds

2.1

Baths

1,717

Sq.Ft.

13890 TITLE WAY

Winter Garden, FL

Courtesy of PRISTINE INTERNATIONAL REALTY LLC
View 11425 PIXIE MANDARIN CT Winter Garden, FL MLS# S5142077
$3,100
3

Beds

2.0

Baths

1,791

Sq.Ft.

11425 PIXIE MANDARIN CT

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 233 SOUTHERN PECAN CIRCLE 101 Winter Garden, FL MLS# S5142016
$1,795
2

Beds

1.0

Baths

966

Sq.Ft.

233 SOUTHERN PECAN CIRCLE 101

Winter Garden, FL

Courtesy of HOMESMART
View 11007 BOOKMARK LANE Winter Garden, FL MLS# O6375276
$2,550
3

Beds

2.1

Baths

1,599

Sq.Ft.

11007 BOOKMARK LANE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 16430 TANGERINE MESA DRIVE Winter Garden, FL MLS# O6374204
$2,700
4

Beds

3.0

Baths

1,715

Sq.Ft.

16430 TANGERINE MESA DRIVE

Winter Garden, FL

Courtesy of KARDOSH REALTY
View 12063 HOLYSTONE STREET Winter Garden, FL MLS# O6374014
$2,490
3

Beds

2.1

Baths

1,451

Sq.Ft.

12063 HOLYSTONE STREET

Winter Garden, FL

Courtesy of ALLUX REAL ESTATE LLC
View 15663 PELICAN CAY DRIVE Winter Garden, FL MLS# O6374627
$3,750
4

Beds

3.1

Baths

2,489

Sq.Ft.

15663 PELICAN CAY DRIVE

Winter Garden, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 5755 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6374324
$2,850
4

Beds

2.1

Baths

2,061

Sq.Ft.

5755 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of THE C SMITH REAL ESTATE GROUP LLC
View 16053 MICELLI DRIVE Winter Garden, FL MLS# O6373074
$3,000
4

Beds

3.0

Baths

2,258

Sq.Ft.

16053 MICELLI DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 934 MCKINNON SQUARE Winter Garden, FL MLS# O6373203
$4,500
3

Beds

2.1

Baths

2,536

Sq.Ft.

934 MCKINNON SQUARE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 15537 HONEYBELL DRIVE Winter Garden, FL MLS# S5141523
$2,700
3

Beds

2.1

Baths

1,584

Sq.Ft.

15537 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of NAIM REAL ESTATE LLC
View 6373 BREEZE FILLED LANE Winter Garden, FL MLS# O6373104
  • New Construction with Virtual Tour
1 of 37
$2,650
3

Beds

2.1

Baths

1,683

Sq.Ft.

6373 BREEZE FILLED LANE

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 5301 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6372658
$6,000
5

Beds

4.1

Baths

3,871

Sq.Ft.

5301 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of CELEBRITY GLOBAL REALTY LLC
View 17670 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6372002
  • New Construction with Virtual Tour
1 of 80
$4,650
5

Beds

4.1

Baths

3,542

Sq.Ft.

17670 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE

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 3/20/2026.