View 1433 PRIORY CIRCLE Winter Garden, FL MLS# O6364550
$385,000
3

Beds

2.1

Baths

1,840

Sq.Ft.

1433 PRIORY CIRCLE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 13562 PEARL BEACH STREET Winter Garden, FL MLS# O6362827
  • Adult Community with Virtual Tour
1 of 36
$435,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

13562 PEARL BEACH STREET

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 15036 CHAPTER WAY Winter Garden, FL MLS# O6364954
$408,000
3

Beds

2.1

Baths

1,717

Sq.Ft.

15036 CHAPTER WAY

Winter Garden, FL

Courtesy of RC GROUP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 12036 HOLYSTONE STREET Winter Garden, FL MLS# S5139531
$455,000
3

Beds

2.1

Baths

1,817

Sq.Ft.

12036 HOLYSTONE STREET

Winter Garden, FL

Courtesy of NAIM REAL ESTATE LLC
View 13545 PEARL BEACH STREET Winter Garden, FL MLS# S5139428
  • Adult Community with Virtual Tour
1 of 40
$428,375
2

Beds

2.0

Baths

1,579

Sq.Ft.

13545 PEARL BEACH STREET

Winter Garden, FL

Courtesy of IMAGINATION REALTY, INC
View 14227 AVENUE OF THE GROVES RUN Winter Garden, FL MLS# O6339064
$359,000
2

Beds

2.1

Baths

1,266

Sq.Ft.

14227 AVENUE OF THE GROVES RUN

Winter Garden, FL

Courtesy of CT HOMES REALTY CORPORATION
View 16180 ARBOR CREST ALLEY Winter Garden, FL MLS# A4673607
$409,000
3

Beds

2.1

Baths

1,996

Sq.Ft.

16180 ARBOR CREST ALLEY

Winter Garden, FL

Courtesy of SAVVY AVENUE, LLC
View 15663 KINNOW MANDARIN LANE Winter Garden, FL MLS# O6363767
  • Virtual Tour
1 of 21
OPEN HOUSE: Saturday 1/10 12:00 PM - 3:00 PM
$426,000
3

Beds

2.1

Baths

1,868

Sq.Ft.

15663 KINNOW MANDARIN LANE

Winter Garden, FL

Courtesy of REAL LIVING R E SOLUTIONS
View 16154 TREADWELL STREET Winter Garden, FL MLS# G5104842
$439,900
3

Beds

2.1

Baths

1,829

Sq.Ft.

16154 TREADWELL STREET

Winter Garden, FL

Courtesy of TOUCHSTONE REAL ESTATE
View 15262 GROVESIDE ROAD Winter Garden, FL MLS# O6361868
  • New Construction with Virtual Tour
1 of 18
$449,990
3

Beds

2.1

Baths

1,846

Sq.Ft.

15262 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 403 LAKE AMBERLEIGH DRIVE Winter Garden, FL MLS# O6361839
  • Adult Community with Virtual Tour
1 of 18
$455,000
3

Beds

2.0

Baths

1,713

Sq.Ft.

403 LAKE AMBERLEIGH DRIVE

Winter Garden, FL

Courtesy of PINNACLE SIGNATURE REALTY LLC
View 15523 BAY BRIDGE STREET Winter Garden, FL MLS# O6361419
$439,990
3

Beds

2.1

Baths

1,691

Sq.Ft.

15523 BAY BRIDGE STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 9410 BOLSHOI ALLEY Winter Garden, FL MLS# O6361431
  • New Construction
1 of 61
$429,990
3

Beds

2.1

Baths

1,691

Sq.Ft.

9410 BOLSHOI ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 14501 GROVE RESORT AVENUE 3535 Winter Garden, FL MLS# S5138632
$389,990
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 3535

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
View 15537 HONEYBELL DRIVE Winter Garden, FL MLS# G5104542
  • Adult Community with Virtual Tour
1 of 25
$379,800
3

Beds

2.1

Baths

1,584

Sq.Ft.

15537 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of LUXE PROPERTIES
View 14801 EVERGREEN OAK LOOP Winter Garden, FL MLS# O6360967
  • Virtual Tour
1 of 37
OPEN HOUSE: Sunday 1/11 2:30 PM - 4:30 PM
$415,000
3

Beds

2.1

Baths

1,741

Sq.Ft.

14801 EVERGREEN OAK LOOP

Winter Garden, FL

Courtesy of VYLLA HOME
View 14501 GROVE RESORT AVENUE 1535 Winter Garden, FL MLS# TB8447837
$435,999
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 1535

Winter Garden, FL

Courtesy of BY OWNER.COM
View 8105 RED STOPPER LANE Winter Garden, FL MLS# O6360454
$425,000
3

Beds

2.1

Baths

1,725

Sq.Ft.

8105 RED STOPPER LANE

Winter Garden, FL

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
View 15693 KINNOW MANDARIN LANE Winter Garden, FL MLS# O6357939
  • Virtual Tour
1 of 59
OPEN HOUSE: Sunday 1/11 2:00 PM - 4:00 PM
$440,000
4

Beds

3.0

Baths

2,033

Sq.Ft.

15693 KINNOW MANDARIN LANE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14501 GROVE RESORT AVENUE 3716 Winter Garden, FL MLS# O6360135
$399,900
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3716

Winter Garden, FL

Courtesy of MBI 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

783

Estimated median home price

$589,000
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 - 100K6
$100K - 200K11
$200K - 300K67
$300K - 400K78
$400K - 500K138
$500K - 600K117
$600K - 700K89
$700K - 800K71
$800K - 900K68
$900K - 1M48
$1M - Max90

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family504
Townhouse123
Condo111
Commercial9
Rental236
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/9/2026)

Information deemed reliable but not guaranteed.

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 1/10/2026.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 1/10/2026.