View 227 TRADITIONS DRIVE Winter Garden, FL MLS# O6372388
  • Recently Listed with Virtual Tour
1 of 30
$2,900
3

Beds

2.0

Baths

1,498

Sq.Ft.

227 TRADITIONS DRIVE

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 934 MCKINNON SQUARE Winter Garden, FL MLS# O6373203
  • Recently Listed with Virtual Tour
1 of 34
$4,500
3

Beds

2.1

Baths

2,536

Sq.Ft.

934 MCKINNON SQUARE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 1016 HUNTSPOINT STREET Winter Garden, FL MLS# O6373540
$5,250
3

Beds

2.1

Baths

2,421

Sq.Ft.

1016 HUNTSPOINT STREET

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 15537 HONEYBELL DRIVE Winter Garden, FL MLS# S5141523
  • Recently Listed with Virtual Tour
1 of 29
$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
  • Recently Listed 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 16311 LAKELET ALLEY Winter Garden, FL MLS# O6372766
  • New Construction with Virtual Tour
1 of 37
$2,500
3

Beds

2.1

Baths

1,560

Sq.Ft.

16311 LAKELET ALLEY

Winter Garden, FL

Courtesy of EAST PEARL REALTY
View 5301 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6372658
  • Recently Listed with Virtual Tour
1 of 51
$6,500
5

Beds

4.1

Baths

3,871

Sq.Ft.

5301 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of ON ME REALTY
View 15244 GROVESIDE ROAD Winter Garden, FL MLS# O6369366
  • New Construction with Virtual Tour
1 of 27
$3,100
3

Beds

2.1

Baths

1,881

Sq.Ft.

15244 GROVESIDE ROAD

Winter Garden, FL

Courtesy of MANAGER PROP
View 357 LAKE AMBERLEIGH DRIVE Winter Garden, FL MLS# O6372126
$2,500
4

Beds

2.1

Baths

2,963

Sq.Ft.

357 LAKE AMBERLEIGH DRIVE

Winter Garden, FL

Courtesy of VYLLA HOME
View 11144 SUSPENSE DRIVE Winter Garden, FL MLS# O6370514
  • Recently Listed with Virtual Tour
1 of 34
$2,650
3

Beds

2.1

Baths

1,717

Sq.Ft.

11144 SUSPENSE DRIVE

Winter Garden, FL

Courtesy of DREAM FINDERS REALTY GROUP CORP
View 15187 CHAPTER WAY Winter Garden, FL MLS# O6371761
  • Virtual Tour
1 of 17
$2,900
4

Beds

3.1

Baths

2,486

Sq.Ft.

15187 CHAPTER WAY

Winter Garden, FL

Courtesy of INTEREALTY SERVICE
View 12662 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# O6371868
  • New Construction with Virtual Tour
1 of 13
$2,900
4

Beds

3.0

Baths

2,148

Sq.Ft.

12662 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17670 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6372002
  • New Construction with Virtual Tour
1 of 80
$5,200
5

Beds

4.1

Baths

3,542

Sq.Ft.

17670 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 4648 PRAIRIE CREEK STREET Winter Garden, FL MLS# O6372258
  • Recently Listed with Virtual Tour
1 of 29
$3,350
3

Beds

3.1

Baths

2,408

Sq.Ft.

4648 PRAIRIE CREEK STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 5133 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6370982
$6,400
4

Beds

3.1

Baths

2,943

Sq.Ft.

5133 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 15050 LAKE BESSIE LOOP Winter Garden, FL MLS# G5106240
$4,000
4

Beds

3.1

Baths

2,633

Sq.Ft.

15050 LAKE BESSIE LOOP

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16067 SCARPETTA STREET Winter Garden, FL MLS# S5141102
$3,400
4

Beds

3.1

Baths

2,494

Sq.Ft.

16067 SCARPETTA STREET

Winter Garden, FL

Courtesy of REMAX PREMIER PROPERTIES
View 301 S BOYD STREET 14 Winter Garden, FL MLS# O6371445
$1,800
2

Beds

1.0

Baths

750

Sq.Ft.

301 S BOYD STREET 14

Winter Garden, FL

Courtesy of REAL PROPERTY INTERNATIONAL
View 2069 NERVA ROAD Winter Garden, FL MLS# O6370605
  • Virtual Tour
1 of 33
$5,000
6

Beds

4.0

Baths

4,280

Sq.Ft.

2069 NERVA ROAD

Winter Garden, FL

Courtesy of CASTRO REALTY GROUP
View 15024 STUTTGART ALLEY Winter Garden, FL MLS# S5141142
$2,995
3

Beds

2.1

Baths

2,079

Sq.Ft.

15024 STUTTGART ALLEY

Winter Garden, FL

Courtesy of NAIM REAL ESTATE 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

818

Estimated median home price

$590,000
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

Price Count
$0 - 100K 7
$100K - 200K 11
$200K - 300K 78
$300K - 400K 82
$400K - 500K 138
$500K - 600K 116
$600K - 700K 103
$700K - 800K 73
$800K - 900K 66
$900K - 1M 55
$1M - Max 89

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 540
Townhouse 120
Condo 118
Commercial 7
Rental 241
Lots and Land 31
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 1
Farms 0

(Data as of 2/1/2026)

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 2/1/2026.