974 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View Address not provided Winter Garden, FL MLS# G5110454
$955,893
6

Beds

4.0

Baths

4,236

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View Address not provided Winter Garden, FL MLS# G5110456
  • New Construction
1 of 2
$510,880
3

Beds

2.0

Baths

1,772

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14680 BLACK CHERRY TRAIL Winter Garden, FL MLS# O6394614
  • Recently Listed with Virtual Tour
1 of 42
$629,000
3

Beds

2.1

Baths

2,233

Sq.Ft.

14680 BLACK CHERRY TRAIL

Winter Garden, FL

Courtesy of REVEL REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 419 WINTER GROVE BOULEVARD Winter Garden, FL MLS# O6395693
  • Recently Listed with Virtual Tour
1 of 35
$874,990
5

Beds

3.1

Baths

2,650

Sq.Ft.

419 WINTER GROVE BOULEVARD

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 408 S BOYD STREET Winter Garden, FL MLS# O6394810
  • Recently Listed with Virtual Tour
1 of 40
$815,000
3

Beds

3.0

Baths

2,295

Sq.Ft.

408 S BOYD STREET

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 14542 GOLDEN HARBOR LANE Winter Garden, FL MLS# O6395116
  • Recently Listed with Virtual Tour
1 of 33
$500,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

14542 GOLDEN HARBOR LANE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 15501 HAMLIN PARK DRIVE Winter Garden, FL MLS# TB8492519
  • Recently Listed with Virtual Tour
1 of 17
$609,990
3

Beds

3.1

Baths

2,072

Sq.Ft.

15501 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 13335 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5110385
  • New Construction with Virtual Tour
1 of 25
$428,000
3

Beds

3.0

Baths

1,715

Sq.Ft.

13335 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6020 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5110387
$573,990
4

Beds

3.0

Baths

2,102

Sq.Ft.

6020 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15070 SUMMER HARVEST STREET Winter Garden, FL MLS# S5146881
  • Recently Listed with Virtual Tour
1 of 38
$729,900
5

Beds

4.1

Baths

2,931

Sq.Ft.

15070 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of 365 REALTY, INC.
View 514 DUNBAR AVENUE Winter Garden, FL MLS# O6394414
  • Virtual Tour
1 of 18
$295,000
3

Beds

2.0

Baths

1,162

Sq.Ft.

514 DUNBAR AVENUE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 14501 GROVE RESORT AVENUE 1110 Winter Garden, FL MLS# A4688528
  • Recently Listed with Virtual Tour
1 of 35
$185,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1110

Winter Garden, FL

Courtesy of DALTON WADE INC
View 5413 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# S5146601
  • Recently Listed with Virtual Tour
1 of 57
$488,000
4

Beds

2.1

Baths

2,131

Sq.Ft.

5413 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of MD3 HOMES LLC
View 242 BLACK SPRINGS LANE Winter Garden, FL MLS# O6395221
$509,000
3

Beds

2.0

Baths

1,909

Sq.Ft.

242 BLACK SPRINGS LANE

Winter Garden, FL

Courtesy of LIBERTY HOME SALES INC
View 327 S LAKEVIEW AVENUE Winter Garden, FL MLS# O6394438
$849,000
3

Beds

3.0

Baths

2,225

Sq.Ft.

327 S LAKEVIEW AVENUE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 15393 SANDFIELD LOOP Winter Garden, FL MLS# O6391325
  • Recently Listed with Virtual Tour
1 of 60
OPEN HOUSE: Saturday 4/18 12:00 PM - 3:00 PM
$935,000
4

Beds

3.1

Baths

4,303

Sq.Ft.

15393 SANDFIELD LOOP

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 12390 CLEAR SAPPHIRE 260 Winter Garden, FL MLS# O6394850
  • Recently Listed
1 of 1
OPEN HOUSE: Sunday 4/19 12:00 PM - 2:00 PM
$849,990
4

Beds

3.0

Baths

2,552

Sq.Ft.

12390 CLEAR SAPPHIRE 260

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 10768 RHETT BUTLER ALLEY Winter Garden, FL MLS# O6396023
  • Recently Listed with Virtual Tour
1 of 48
$424,000
3

Beds

2.1

Baths

1,636

Sq.Ft.

10768 RHETT BUTLER ALLEY

Winter Garden, FL

Courtesy of KARDOSH REALTY
View 706 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6394059
  • Recently Listed with Virtual Tour
1 of 49
OPEN HOUSE: Saturday 4/18 12:00 PM - 3:00 PM
$1,337,000
5

Beds

5.2

Baths

4,019

Sq.Ft.

706 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 11045 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6394192
  • Recently Listed with Virtual Tour
1 of 43
$749,900
4

Beds

3.0

Baths

2,113

Sq.Ft.

11045 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of VOSS REALTY INC

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

974

Estimated median home price

$599,900
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 1
$100K - 200K 19
$200K - 300K 95
$300K - 400K 80
$400K - 500K 148
$500K - 600K 152
$600K - 700K 119
$700K - 800K 100
$800K - 900K 88
$900K - 1M 65
$1M - Max 107

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 673
Townhouse 134
Condo 129
Commercial 12
Rental 231
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 4/16/2026)

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.

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© Copyright 2026 New Smyrna Beach Board 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 on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

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.

Data is updated as of 4/17/2026.

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

Copyright 2026 BeachesMLS, Inc. All rights reserved.

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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.

Data is updated as of 4/17/2026.

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.

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 4/17/2026.