236 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 17108 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5117579
$712,735
4

Beds

3.0

Baths

3,038

Sq.Ft.

17108 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 809 BURCH AVENUE Winter Garden, FL MLS# O6440306
$649,999
4

Beds

4.1

Baths

3,543

Sq.Ft.

809 BURCH AVENUE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 502 PALM DRIVE Winter Garden, FL MLS# O6436846
  • Virtual Tour
1 of 37
$699,700
4

Beds

2.1

Baths

3,009

Sq.Ft.

502 PALM DRIVE

Winter Garden, FL

Courtesy of WINDSOR REALTY GROUP INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 17425 WATER HEMLOCK ROAD Winter Garden, FL MLS# O6438971
  • New Construction with Virtual Tour
1 of 21
OPEN HOUSE: Saturday 11/14 12:00 PM - 4:00 PM
$769,990
4

Beds

3.0

Baths

2,869

Sq.Ft.

17425 WATER HEMLOCK ROAD

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 15526 MANGO ISLE STREET Winter Garden, FL MLS# O6437872
$749,700
4

Beds

3.0

Baths

2,117

Sq.Ft.

15526 MANGO ISLE STREET

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 2039 HARBOR COVE WAY Winter Garden, FL MLS# O6435631
$710,000
4

Beds

3.0

Baths

2,643

Sq.Ft.

2039 HARBOR COVE WAY

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 7608 SUMMERLAKE GROVES ST Winter Garden, FL MLS# O6438685
$583,000
5

Beds

3.0

Baths

2,461

Sq.Ft.

7608 SUMMERLAKE GROVES ST

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 17322 BEACHGRASS ALLEY Winter Garden, FL MLS# O6438247
  • New Construction with Virtual Tour
1 of 20
$669,990
4

Beds

3.1

Baths

2,791

Sq.Ft.

17322 BEACHGRASS ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 17431 WATER HEMLOCK ROAD Winter Garden, FL MLS# O6439017
  • New Construction with Virtual Tour
1 of 24
OPEN HOUSE: Saturday 11/14 12:00 PM - 4:00 PM
$749,990
4

Beds

3.0

Baths

2,908

Sq.Ft.

17431 WATER HEMLOCK ROAD

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 8001 POND APPLE DRIVE Winter Garden, FL MLS# O6437864
$688,800
5

Beds

3.0

Baths

3,289

Sq.Ft.

8001 POND APPLE DRIVE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 6135 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5117323
$765,490
4

Beds

3.1

Baths

2,688

Sq.Ft.

6135 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 2420 BALFORN TOWER WAY Winter Garden, FL MLS# O6438016
$599,900
3

Beds

2.0

Baths

1,572

Sq.Ft.

2420 BALFORN TOWER WAY

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 13235 SPRING GROVE WAY Winter Garden, FL MLS# O6437214
$595,000
3

Beds

2.0

Baths

1,916

Sq.Ft.

13235 SPRING GROVE WAY

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 301 VALENCIA COURT Winter Garden, FL MLS# NS1089084
$649,000
4

Beds

2.1

Baths

2,029

Sq.Ft.

301 VALENCIA COURT

Winter Garden, FL

View 301 VALENCIA COURT Winter Garden, FL MLS# NS1089084
$649,000
4

Beds

2.1

Baths

2,029

Sq.Ft.

301 VALENCIA COURT

Winter Garden, FL

Courtesy of WHITE WHALE REAL ESTATE
View 1750 STANDING ROCK CIRCLE Winter Garden, FL MLS# S5156172
$640,000
4

Beds

2.1

Baths

2,614

Sq.Ft.

1750 STANDING ROCK CIRCLE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 7278 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6436600
$599,000
4

Beds

2.0

Baths

2,014

Sq.Ft.

7278 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 17307 BAL HARBOUR DRIVE Winter Garden, FL MLS# O6436527
$624,900
3

Beds

2.0

Baths

2,123

Sq.Ft.

17307 BAL HARBOUR DRIVE

Winter Garden, FL

Courtesy of LOVELAND PROPERTIES
View 368 N BOYD STREET Winter Garden, FL MLS# O6430188
  • Virtual Tour
1 of 54
OPEN HOUSE: Saturday 11/14 10:30 AM - 1:30 PM
$774,900
4

Beds

2.1

Baths

2,331

Sq.Ft.

368 N BOYD STREET

Winter Garden, FL

Courtesy of FATHOM REALTY FL LLC
View 2027 RICKOVER PLACE Winter Garden, FL MLS# O6434615
$699,000
5

Beds

4.0

Baths

3,078

Sq.Ft.

2027 RICKOVER PLACE

Winter Garden, FL

Courtesy of CREEGAN GROUP

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

948

Estimated median home price

$615,033
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 - 200K36
$200K - 300K76
$300K - 400K68
$400K - 500K140
$500K - 600K144
$600K - 700K118
$700K - 800K104
$800K - 900K103
$900K - 1M52
$1M - Max106

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family649
Townhouse140
Condo117
Commercial5
Rental244
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home1
Farms0

(Data as of 11/14/2026)

Information deemed reliable but not guaranteed.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being 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.

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.

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 11/14/2026.