240 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 7000 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6381796
  • Recently Listed with Virtual Tour
1 of 29
$2,900
4

Beds

3.1

Baths

1,914

Sq.Ft.

7000 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 17320 SWEET MORO DRIVE Winter Garden, FL MLS# O6380499
  • Recently Listed with Virtual Tour
1 of 57
$2,850
3

Beds

2.1

Baths

1,668

Sq.Ft.

17320 SWEET MORO DRIVE

Winter Garden, FL

Courtesy of ALLUX REAL ESTATE LLC
View 15262 GROVESIDE ROAD Winter Garden, FL MLS# O6381286
  • Recently Listed with Virtual Tour
1 of 26
$2,750
3

Beds

2.1

Baths

1,830

Sq.Ft.

15262 GROVESIDE ROAD

Winter Garden, FL

Courtesy of C BRENNER INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 16856 HYPATIA ALLEY Winter Garden, FL MLS# O6381467
  • Recently Listed with Virtual Tour
1 of 27
$2,750
3

Beds

2.0

Baths

1,705

Sq.Ft.

16856 HYPATIA ALLEY

Winter Garden, FL

Courtesy of SUNNY 365 REALTY GROUP
View 15704 MARINA BAY DRIVE Winter Garden, FL MLS# O6380878
$11,500
5

Beds

5.1

Baths

5,005

Sq.Ft.

15704 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of DOUBLE M GROUP COMPANY
View 15627 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6381086
  • Recently Listed with Virtual Tour
1 of 45
$2,700
3

Beds

2.1

Baths

1,518

Sq.Ft.

15627 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of GARCIA REALTY GROUP
View 12893 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6381091
  • Recently Listed with Virtual Tour
1 of 46
$4,700
5

Beds

4.1

Baths

3,165

Sq.Ft.

12893 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of JC FLORIDA REALTY LLC
View 16007 MICELLI DRIVE Winter Garden, FL MLS# O6381108
  • Recently Listed with Virtual Tour
1 of 58
$3,100
4

Beds

3.1

Baths

2,749

Sq.Ft.

16007 MICELLI DRIVE

Winter Garden, FL

Courtesy of U KEY REALTY
View 16246 MERRY ALLEY Winter Garden, FL MLS# O6381155
  • Recently Listed with Virtual Tour
1 of 41
$2,650
3

Beds

2.1

Baths

1,683

Sq.Ft.

16246 MERRY ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 13344 HARBOR SHORE LANE Winter Garden, FL MLS# S5143640
  • Recently Listed with Virtual Tour
1 of 18
$2,250
2

Beds

2.1

Baths

1,234

Sq.Ft.

13344 HARBOR SHORE LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 11150 SOUND SHORE DRIVE Winter Garden, FL MLS# O6380804
  • Recently Listed with Virtual Tour
1 of 43
$2,700
3

Beds

2.0

Baths

1,689

Sq.Ft.

11150 SOUND SHORE DRIVE

Winter Garden, FL

Courtesy of US SQUARE REAL ESTATE
View 17834 ADRIFT ROAD Winter Garden, FL MLS# O6380850
  • Recently Listed with Virtual Tour
1 of 36
$4,500
4

Beds

3.1

Baths

2,674

Sq.Ft.

17834 ADRIFT ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 431 SOUTHERN PECAN CIRCLE 201 Winter Garden, FL MLS# S5142462
  • Recently Listed with Virtual Tour
1 of 17
$2,550
3

Beds

2.0

Baths

1,499

Sq.Ft.

431 SOUTHERN PECAN CIRCLE 201

Winter Garden, FL

Courtesy of HOMESMART
View 15481 BAY BRIDGE STREET Winter Garden, FL MLS# O6380391
  • Recently Listed with Virtual Tour
1 of 30
$2,900
3

Beds

2.1

Baths

1,670

Sq.Ft.

15481 BAY BRIDGE STREET

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 15010 SUMMER HARVEST STREET Winter Garden, FL MLS# O6371081
  • Recently Listed with Virtual Tour
1 of 25
$3,400
4

Beds

3.1

Baths

2,322

Sq.Ft.

15010 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 6340 TABEBUIA PARKWAY Winter Garden, FL MLS# O6380528
  • Recently Listed with Virtual Tour
1 of 32
$2,600
3

Beds

2.1

Baths

1,501

Sq.Ft.

6340 TABEBUIA PARKWAY

Winter Garden, FL

Courtesy of THE CARDENAS GROUP REALTY
View 1220 PRIORY CIRCLE Winter Garden, FL MLS# O6380944
  • Recently Listed with Virtual Tour
1 of 42
$3,000
3

Beds

2.1

Baths

1,971

Sq.Ft.

1220 PRIORY CIRCLE

Winter Garden, FL

Courtesy of REAL ESTATE FIRM OF ORLANDO
View 1646 SCARLET OAK LOOP 58C Winter Garden, FL MLS# O6380082
  • Recently Listed with Virtual Tour
1 of 37
$2,250
3

Beds

2.1

Baths

1,699

Sq.Ft.

1646 SCARLET OAK LOOP 58C

Winter Garden, FL

Courtesy of JAMIESON PROPERTIES, INC.
View 5519 MYRTLE PINE LANE Winter Garden, FL MLS# O6380094
  • Recently Listed with Virtual Tour
1 of 11
$2,700
4

Beds

2.0

Baths

1,851

Sq.Ft.

5519 MYRTLE PINE LANE

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 7556 JOHN HANCOCK DRIVE Winter Garden, FL MLS# O6380128
  • Recently Listed with Virtual Tour
1 of 95
$18,000
5

Beds

6.1

Baths

5,108

Sq.Ft.

7556 JOHN HANCOCK DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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

864

Estimated median home price

$590,350
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 - 200K13
$200K - 300K86
$300K - 400K77
$400K - 500K141
$500K - 600K134
$600K - 700K105
$700K - 800K79
$800K - 900K68
$900K - 1M57
$1M - Max98

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family574
Townhouse128
Condo123
Commercial9
Rental243
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 2/19/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein or for their use or interpretation by the user. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

This data updated periodically, at an interval not to exceed 7 days.

IDX information 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

© Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

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 2/20/2026.