View 417 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# O6403943
  • Recently Listed with Virtual Tour
1 of 19
$2,095
2

Beds

2.0

Baths

1,264

Sq.Ft.

417 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

Courtesy of AFT PROPERTY LLC
View 7699 TANGERINE KNOLL LOOP Winter Garden, FL MLS# O6404238
$3,350
4

Beds

3.1

Baths

2,697

Sq.Ft.

7699 TANGERINE KNOLL LOOP

Winter Garden, FL

Courtesy of TRUVISION REAL ESTATE LLC
View 17007 SEVILLE ORANGE ROAD Winter Garden, FL MLS# O6404250
$2,850
3

Beds

2.0

Baths

1,798

Sq.Ft.

17007 SEVILLE ORANGE ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 16276 MERRY ALLEY Winter Garden, FL MLS# O6404597
  • Recently Listed
1 of 22
$3,000
4

Beds

2.1

Baths

1,770

Sq.Ft.

16276 MERRY ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16440 HAMLIN HILLS ROAD Winter Garden, FL MLS# O6404052
  • Recently Listed with Virtual Tour
1 of 12
$2,850
3

Beds

2.1

Baths

1,624

Sq.Ft.

16440 HAMLIN HILLS ROAD

Winter Garden, FL

Courtesy of KICANTO REALTY
View 14384 BRAEMAR STREET Winter Garden, FL MLS# O6400691
  • Recently Listed with Virtual Tour
1 of 15
$2,850
3

Beds

2.1

Baths

2,000

Sq.Ft.

14384 BRAEMAR STREET

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 12626 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# O6404139
  • Recently Listed with Virtual Tour
1 of 34
$3,500
4

Beds

3.0

Baths

2,500

Sq.Ft.

12626 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

Courtesy of REMI EMERSON RESIDENTIAL
View 709 GARDEN WEST TERRACE Winter Garden, FL MLS# O6404301
  • Recently Listed with Virtual Tour
1 of 45
$5,500
3

Beds

3.1

Baths

2,591

Sq.Ft.

709 GARDEN WEST TERRACE

Winter Garden, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 6224 ARALIA IVY LANE Winter Garden, FL MLS# O6404181
$2,900
3

Beds

2.1

Baths

1,560

Sq.Ft.

6224 ARALIA IVY LANE

Winter Garden, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 5654 WESTVIEW PARK DRIVE Winter Garden, FL MLS# S5148611
  • Recently Listed with Virtual Tour
1 of 20
$2,800
3

Beds

2.1

Baths

1,846

Sq.Ft.

5654 WESTVIEW PARK DRIVE

Winter Garden, FL

Courtesy of FRONTLINE FLORIDA REALTY, INC.
View 2827 SANCTUARY LANE Winter Garden, FL MLS# O6403747
  • Recently Listed with Virtual Tour
1 of 58
$4,500
3

Beds

2.1

Baths

2,178

Sq.Ft.

2827 SANCTUARY LANE

Winter Garden, FL

Courtesy of GARCIA REALTY GROUP
View 14443 PRUNNINGWOOD PLACE Winter Garden, FL MLS# A4692044
  • Recently Listed with Virtual Tour
1 of 13
$2,200
2

Beds

2.1

Baths

1,228

Sq.Ft.

14443 PRUNNINGWOOD PLACE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 2227 OAKINGTON STREET Winter Garden, FL MLS# O6403884
  • Recently Listed with Virtual Tour
1 of 43
$2,995
3

Beds

2.0

Baths

1,867

Sq.Ft.

2227 OAKINGTON STREET

Winter Garden, FL

Courtesy of REALTY ONE GROUP EVOLUTION
View 12067 HOLYSTONE STREET Winter Garden, FL MLS# O6403881
  • Recently Listed with Virtual Tour
1 of 14
$2,650
3

Beds

2.1

Baths

1,654

Sq.Ft.

12067 HOLYSTONE STREET

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 15190 GROVESIDE ROAD Winter Garden, FL MLS# O6404084
  • Recently Listed with Virtual Tour
1 of 23
$3,150
4

Beds

3.1

Baths

1,881

Sq.Ft.

15190 GROVESIDE ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16292 BRIGHT LEAF ROAD Winter Garden, FL MLS# S5148798
  • Recently Listed with Virtual Tour
1 of 44
$2,620
3

Beds

2.1

Baths

1,553

Sq.Ft.

16292 BRIGHT LEAF ROAD

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 12112 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6403110
  • Recently Listed with Virtual Tour
1 of 42
$3,350
4

Beds

3.1

Baths

2,781

Sq.Ft.

12112 ENCORE AT OVATION WAY

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 9158 SONOMA COAST DRIVE Winter Garden, FL MLS# TB8502828
$3,495
4

Beds

3.0

Baths

2,117

Sq.Ft.

9158 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of 7 BLUE LLC
View 502 S HIGHLAND AVENUE Winter Garden, FL MLS# O6403053
  • Recently Listed with Virtual Tour
1 of 17
$2,800
3

Beds

1.0

Baths

2,102

Sq.Ft.

502 S HIGHLAND AVENUE

Winter Garden, FL

Courtesy of NEW SOLUTIONS REALTY INC
View 10013 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6402442
  • Recently Listed with Virtual Tour
1 of 34
$5,150
6

Beds

4.1

Baths

4,505

Sq.Ft.

10013 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of OKKLA REALTY

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

995

Estimated median home price

$609,850
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 - 100K1
$100K - 200K18
$200K - 300K99
$300K - 400K80
$400K - 500K140
$500K - 600K153
$600K - 700K129
$700K - 800K113
$800K - 900K85
$900K - 1M70
$1M - Max107

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family684
Townhouse133
Condo138
Commercial11
Rental214
Lots and Land27
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 5/4/2026)

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 5/4/2026.