View 14843 ASTROLYN STREET Winter Garden, FL MLS# O6374084
  • Recently Listed with Virtual Tour
1 of 16
$1,950
3

Beds

2.0

Baths

1,260

Sq.Ft.

14843 ASTROLYN STREET

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 15049 SPINNAKER COVE LANE Winter Garden, FL MLS# O6376471
$4,250
4

Beds

3.0

Baths

2,700

Sq.Ft.

15049 SPINNAKER COVE LANE

Winter Garden, FL

Courtesy of RATIO REAL ESTATE, LLC
View 15532 SWEET ORANGE AVENUE Winter Garden, FL MLS# O6376556
  • Recently Listed with Virtual Tour
1 of 50
$3,950
3

Beds

2.1

Baths

2,571

Sq.Ft.

15532 SWEET ORANGE AVENUE

Winter Garden, FL

Courtesy of BEST ORLANDO PROPERTY MANAGEMENT LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 4306 OLD SYCAMORE LOOP Winter Garden, FL MLS# O6376530
  • Recently Listed with Virtual Tour
1 of 55
$6,600
5

Beds

3.1

Baths

4,050

Sq.Ft.

4306 OLD SYCAMORE LOOP

Winter Garden, FL

Courtesy of SELECTA REALTY LLC
View 14931 LEBEAU LOOP Winter Garden, FL MLS# O6376599
  • Recently Listed with Virtual Tour
1 of 57
OPEN HOUSE: Sunday 1/25 10:00 AM - 2:00 PM
$5,400
4

Beds

3.1

Baths

2,832

Sq.Ft.

14931 LEBEAU LOOP

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 139 E STORY ROAD A Winter Garden, FL MLS# O6376451
  • Recently Listed with Virtual Tour
1 of 12
$1,755
2

Beds

1.0

Baths

985

Sq.Ft.

139 E STORY ROAD A

Winter Garden, FL

Courtesy of FLAMINGO REALTY OF ORLANDO
View 14464 WHITTRIDGE DRIVE Winter Garden, FL MLS# G5106944
  • Recently Listed with Virtual Tour
1 of 36
$3,400
5

Beds

3.1

Baths

2,835

Sq.Ft.

14464 WHITTRIDGE DRIVE

Winter Garden, FL

Courtesy of OPTIMA ONE REALTY, INC.
View 17326 SWEET MORO DRIVE Winter Garden, FL MLS# O6376194
  • Recently Listed with Virtual Tour
1 of 23
$2,600
3

Beds

2.1

Baths

1,584

Sq.Ft.

17326 SWEET MORO DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 39 WINDTREE LANE 104 Winter Garden, FL MLS# O6375753
  • Recently Listed with Virtual Tour
1 of 22
$1,750
2

Beds

2.0

Baths

918

Sq.Ft.

39 WINDTREE LANE 104

Winter Garden, FL

Courtesy of INDEPENDENCE REALTY GROUP LLC
View 16599 BARBOURS WAY Winter Garden, FL MLS# O6375758
  • Recently Listed with Virtual Tour
1 of 39
$2,600
3

Beds

2.1

Baths

1,567

Sq.Ft.

16599 BARBOURS WAY

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 15633 WATER SPRING BOULEVARD Winter Garden, FL MLS# S5142204
  • Recently Listed with Virtual Tour
1 of 81
$2,800
4

Beds

2.1

Baths

1,992

Sq.Ft.

15633 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 13931 DANIELS LANDING CIRCLE Winter Garden, FL MLS# O6375806
  • Recently Listed with Virtual Tour
1 of 17
$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
  • Recently Listed with Virtual Tour
1 of 27
$2,990
4

Beds

2.1

Baths

2,000

Sq.Ft.

10696 WORDS DRIVE

Winter Garden, FL

Courtesy of JC FLORIDA REALTY LLC
View 16218 CASTELO LIME ALLEY Winter Garden, FL MLS# O6371472
  • Recently Listed with Virtual Tour
1 of 34
$2,550
3

Beds

2.1

Baths

1,736

Sq.Ft.

16218 CASTELO LIME ALLEY

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 14835 OLD THICKET TRACE Winter Garden, FL MLS# O6375317
  • Recently Listed with Virtual Tour
1 of 32
$3,800
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
  • Recently Listed with Virtual Tour
1 of 27
$2,600
3

Beds

2.0

Baths

1,439

Sq.Ft.

418 CHARLES STREET

Winter Garden, FL

Courtesy of CANI PROPERTY MANAGEMENT
View 9129 PINCH SHOT DRIVE Winter Garden, FL MLS# O6374872
  • Recently Listed with Virtual Tour
1 of 21
$3,150
5

Beds

3.0

Baths

2,638

Sq.Ft.

9129 PINCH SHOT DRIVE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 13890 TITLE WAY Winter Garden, FL MLS# O6372589
  • Recently Listed with Virtual Tour
1 of 31
$2,950
3

Beds

2.1

Baths

1,717

Sq.Ft.

13890 TITLE WAY

Winter Garden, FL

Courtesy of PRISTINE INTERNATIONAL REALTY LLC
View 319 GRAND ROYAL CIRCLE Winter Garden, FL MLS# G5106960
$2,600
3

Beds

2.0

Baths

1,612

Sq.Ft.

319 GRAND ROYAL CIRCLE

Winter Garden, FL

Courtesy of ENGEL & VOLKERS CLERMONT
View 11425 PIXIE MANDARIN CT Winter Garden, FL MLS# S5142077
$3,200
3

Beds

2.0

Baths

1,791

Sq.Ft.

11425 PIXIE MANDARIN CT

Winter Garden, FL

Courtesy of LPT 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

814

Estimated median home price

$589,945
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 - 100K7
$100K - 200K12
$200K - 300K72
$300K - 400K83
$400K - 500K142
$500K - 600K118
$600K - 700K97
$700K - 800K76
$800K - 900K67
$900K - 1M49
$1M - Max91

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family526
Townhouse129
Condo117
Commercial7
Rental239
Lots and Land33
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/22/2026)

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 1/25/2026.