240 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 1165 E PLANT STREET Winter Garden, FL MLS# O6384089
  • Recently Listed with Virtual Tour
1 of 9
$27,480
1,200

Sq.Ft.

1165 E PLANT STREET

Winter Garden, FL

Courtesy of LOKATION
View 15342 OAK APPLE COURT Winter Garden, FL MLS# S5144129
  • Recently Listed with Virtual Tour
1 of 25
$2,195
3

Beds

2.1

Baths

1,699

Sq.Ft.

15342 OAK APPLE COURT

Winter Garden, FL

Courtesy of YELLOW MOUNTAIN REALTY, LLC
View 17082 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6383549
  • Recently Listed with Virtual Tour
1 of 47
$3,300
4

Beds

3.1

Baths

2,298

Sq.Ft.

17082 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
The time to sell is now! THE TIME TO SELL IS NOW!
View 336 E PLANT STREET Winter Garden, FL MLS# O6381842
  • Recently Listed with Virtual Tour
1 of 18
$784
1,232

Sq.Ft.

336 E PLANT STREET

Winter Garden, FL

Courtesy of WINTER GARDEN REAL ESTATE
View 5395 BOWMAN DRIVE Winter Garden, FL MLS# S5143992
  • Recently Listed with Virtual Tour
1 of 42
$3,350
4

Beds

3.0

Baths

2,768

Sq.Ft.

5395 BOWMAN DRIVE

Winter Garden, FL

Courtesy of TRANSCEND REALTY
View 10360 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6383063
  • Recently Listed with Virtual Tour
1 of 51
$2,800
3

Beds

2.1

Baths

2,204

Sq.Ft.

10360 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 9014 SONOMA COAST DRIVE Winter Garden, FL MLS# O6383077
  • Recently Listed with Virtual Tour
1 of 40
$4,200
4

Beds

4.1

Baths

3,426

Sq.Ft.

9014 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P
View 9014 PINCH SHOT DRIVE Winter Garden, FL MLS# O6382871
$3,500
3

Beds

2.0

Baths

2,089

Sq.Ft.

9014 PINCH SHOT DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16236 OUTLOOK SHORE Winter Garden, FL MLS# S5144009
  • Recently Listed with Virtual Tour
1 of 21
$3,300
4

Beds

3.1

Baths

2,489

Sq.Ft.

16236 OUTLOOK SHORE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 9377 MEADOW HUNT WAY Winter Garden, FL MLS# O6382869
  • Recently Listed with Virtual Tour
1 of 16
$2,850
4

Beds

2.1

Baths

2,072

Sq.Ft.

9377 MEADOW HUNT WAY

Winter Garden, FL

Courtesy of GLASSTONE GROUP INC
View 16375 HAMLIN HILLS ROAD Winter Garden, FL MLS# O6383286
  • Recently Listed with Virtual Tour
1 of 13
$3,075
4

Beds

3.0

Baths

1,715

Sq.Ft.

16375 HAMLIN HILLS ROAD

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16348 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# S5143913
  • Recently Listed with Virtual Tour
1 of 12
$2,560
3

Beds

2.1

Baths

1,626

Sq.Ft.

16348 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of ACKLEY FLORIDA PROPERTY MANAGEMENT INC
View 9588 JACQUES ALLEY Winter Garden, FL MLS# O6382573
  • Recently Listed with Virtual Tour
1 of 17
$3,050
3

Beds

2.1

Baths

2,014

Sq.Ft.

9588 JACQUES ALLEY

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
View 1519 PRIORY CIRCLE Winter Garden, FL MLS# O6382465
  • Recently Listed with Virtual Tour
1 of 27
$2,995
3

Beds

2.1

Baths

1,956

Sq.Ft.

1519 PRIORY CIRCLE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 5612 WATER PIER LANE Winter Garden, FL MLS# O6381878
$3,500
4

Beds

3.1

Baths

2,860

Sq.Ft.

5612 WATER PIER LANE

Winter Garden, FL

Courtesy of SHINING OAK REALTY
View 5977 PAINTED LEAF DRIVE Winter Garden, FL MLS# O6382042
  • Recently Listed with Virtual Tour
1 of 25
$3,000
3

Beds

2.1

Baths

2,128

Sq.Ft.

5977 PAINTED LEAF DRIVE

Winter Garden, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 10284 ATWATER BAY DRIVE Winter Garden, FL MLS# O6382148
  • Recently Listed with Virtual Tour
1 of 23
$3,250
4

Beds

3.0

Baths

2,300

Sq.Ft.

10284 ATWATER BAY DRIVE

Winter Garden, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View Address not provided Winter Garden, FL MLS# O6382298
  • Recently Listed with Virtual Tour
1 of 67
$3,000
3

Beds

2.1

Baths

1,848

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of CONDOMINIUM MARKETING LLC
View 14311 BRAEMAR STREET Winter Garden, FL MLS# O6382360
  • Recently Listed with Virtual Tour
1 of 24
$3,000
4

Beds

2.1

Baths

2,011

Sq.Ft.

14311 BRAEMAR STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 11876 SHINE VIEW LANE Winter Garden, FL MLS# O6381325
  • Recently Listed with Virtual Tour
1 of 51
$3,600
4

Beds

3.1

Baths

2,496

Sq.Ft.

11876 SHINE VIEW LANE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES

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.