View 7192 WILD STRAWBERRY RUN Winter Garden, FL MLS# O6369278
  • Recently Listed with Virtual Tour
1 of 15
$2,850
3

Beds

2.0

Baths

2,094

Sq.Ft.

7192 WILD STRAWBERRY RUN

Winter Garden, FL

Courtesy of SUNNY 365 REALTY GROUP
View 9640 AMBER CHESTNUT WAY Winter Garden, FL MLS# O6368978
  • Recently Listed with Virtual Tour
1 of 32
$2,950
4

Beds

3.1

Baths

2,303

Sq.Ft.

9640 AMBER CHESTNUT WAY

Winter Garden, FL

Courtesy of PREMIER CAPITAL REALTY LLC
View 14250 BRAEMAR STREET Winter Garden, FL MLS# O6368884
  • Recently Listed with Virtual Tour
1 of 21
$2,875
3

Beds

2.1

Baths

1,788

Sq.Ft.

14250 BRAEMAR STREET

Winter Garden, FL

Courtesy of RIO HOMES AND INVESTMENTS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15129 SUMMER HARVEST STREET Winter Garden, FL MLS# O6369574
  • Recently Listed with Virtual Tour
1 of 45
$3,400
4

Beds

3.1

Baths

2,338

Sq.Ft.

15129 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 13896 LANYARD WAY Winter Garden, FL MLS# O6368885
  • Recently Listed with Virtual Tour
1 of 25
$4,800
5

Beds

4.0

Baths

3,611

Sq.Ft.

13896 LANYARD WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 13111 FARO COURT Winter Garden, FL MLS# O6368873
  • Recently Listed with Virtual Tour
1 of 29
$4,400
5

Beds

4.0

Baths

3,243

Sq.Ft.

13111 FARO COURT

Winter Garden, FL

Courtesy of JC FLORIDA REALTY LLC
View 1021 TEMPLE GROVE PLACE Winter Garden, FL MLS# TB8458129
  • Recently Listed with Virtual Tour
1 of 17
$9,500
4

Beds

4.1

Baths

3,185

Sq.Ft.

1021 TEMPLE GROVE PLACE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 14765 SETON CREEK BOULEVARD Winter Garden, FL MLS# O6368569
  • Recently Listed with Virtual Tour
1 of 19
$3,500
4

Beds

3.1

Baths

3,000

Sq.Ft.

14765 SETON CREEK BOULEVARD

Winter Garden, FL

Courtesy of US RELIANCE SOLUTIONS INC
View 13352 HARBOR SHORE LANE 13352 Winter Garden, FL MLS# O6368717
  • Recently Listed with Virtual Tour
1 of 18
$2,400
2

Beds

2.1

Baths

1,234

Sq.Ft.

13352 HARBOR SHORE LANE 13352

Winter Garden, FL

Courtesy of FLORIDA PRESTIGIOUS HOMES INC
View 10774 RHETT BUTLER ALLEY Winter Garden, FL MLS# O6368725
  • Recently Listed with Virtual Tour
1 of 28
$2,750
3

Beds

2.1

Baths

1,618

Sq.Ft.

10774 RHETT BUTLER ALLEY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 15609 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6368574
  • Recently Listed with Virtual Tour
1 of 25
$2,850
3

Beds

2.1

Baths

1,755

Sq.Ft.

15609 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of JC FLORIDA REALTY LLC
View 1532 BROKEN OAK DRIVE B Winter Garden, FL MLS# O6368561
  • Recently Listed with Virtual Tour
1 of 29
$2,150
3

Beds

2.1

Baths

1,544

Sq.Ft.

1532 BROKEN OAK DRIVE B

Winter Garden, FL

Courtesy of BLUE MAGNOLIA REALTY LLC
View 16862 HYPATIA ALLEY Winter Garden, FL MLS# O6369426
  • Recently Listed with Virtual Tour
1 of 45
$3,300
4

Beds

3.1

Baths

2,489

Sq.Ft.

16862 HYPATIA ALLEY

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View Address not provided Winter Garden, FL MLS# TB8457506
  • Recently Listed with Virtual Tour
1 of 18
$2,549
4

Beds

2.1

Baths

2,013

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of TAH FLORIDA LLC
View 15910 MARINA BAY DRIVE Winter Garden, FL MLS# G5105704
  • Recently Listed with Virtual Tour
1 of 39
$2,900
3

Beds

2.1

Baths

1,505

Sq.Ft.

15910 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17592 NORTHLAKE GROVE DRIVE Winter Garden, FL MLS# S5140376
$2,500
3

Beds

3.0

Baths

1,577

Sq.Ft.

17592 NORTHLAKE GROVE DRIVE

Winter Garden, FL

Courtesy of CELEBRATION RENTAL GROUP
View 14537 CRESTED PLUME DRIVE Winter Garden, FL MLS# O6362594
$2,800
4

Beds

2.1

Baths

2,047

Sq.Ft.

14537 CRESTED PLUME DRIVE

Winter Garden, FL

Courtesy of POINTON REALTY INC
View 16025 SILVER BROOK WAY Winter Garden, FL MLS# O6368179
  • Recently Listed
1 of 72
$4,650
4

Beds

3.0

Baths

2,082

Sq.Ft.

16025 SILVER BROOK WAY

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 927 SHADOWMOSS DRIVE Winter Garden, FL MLS# S5140417
  • Recently Listed with Virtual Tour
1 of 28
$3,200
5

Beds

3.0

Baths

2,544

Sq.Ft.

927 SHADOWMOSS DRIVE

Winter Garden, FL

Courtesy of TOPSKY REALTY INC
View 15056 WINDFLOWER ALLEY Winter Garden, FL MLS# O6368600
  • Recently Listed
1 of 26
$2,600
3

Beds

2.1

Baths

1,536

Sq.Ft.

15056 WINDFLOWER ALLEY

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

767

Estimated median home price

$587,000
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 8
$200K - 300K 64
$300K - 400K 82
$400K - 500K 131
$500K - 600K 121
$600K - 700K 85
$700K - 800K 67
$800K - 900K 61
$900K - 1M 49
$1M - Max 92

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 496
Townhouse 117
Condo 110
Commercial 10
Rental 223
Lots and Land 30
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 1
Farms 0

(Data as of 1/2/2026)

Information deemed reliable but not guaranteed.

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 1/3/2026.