275 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 14542 BLACK CHERRY TRAIL Winter Garden, FL MLS# O6410574
  • Recently Listed with Virtual Tour
1 of 36
$600,000
4

Beds

2.1

Baths

2,234

Sq.Ft.

14542 BLACK CHERRY TRAIL

Winter Garden, FL

Courtesy of DALTON WADE INC
View 12444 WESTFIELD LAKES CIRCLE Winter Garden, FL MLS# O6399607
$599,900
4

Beds

3.0

Baths

2,180

Sq.Ft.

12444 WESTFIELD LAKES CIRCLE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 1158 ORANGE SEASON LANE Winter Garden, FL MLS# O6402123
  • Recently Listed with Virtual Tour
1 of 44
$525,000
3

Beds

2.1

Baths

2,444

Sq.Ft.

1158 ORANGE SEASON LANE

Winter Garden, FL

Courtesy of OAK AVENUE REAL ESTATE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 516 S HIGHLAND AVENUE Winter Garden, FL MLS# O6409675
$500,000
3

Beds

2.0

Baths

1,716

Sq.Ft.

516 S HIGHLAND AVENUE

Winter Garden, FL

Courtesy of WINDSOR REALTY GROUP INC
View 231 DOE RUN DRIVE Winter Garden, FL MLS# O6412284
  • Recently Listed with Virtual Tour
1 of 47
$500,000
4

Beds

2.0

Baths

1,972

Sq.Ft.

231 DOE RUN DRIVE

Winter Garden, FL

Courtesy of THE C SMITH REAL ESTATE GROUP LLC
View 1005 CHASE DRIVE Winter Garden, FL MLS# O6411451
  • Recently Listed with Virtual Tour
1 of 39
OPEN HOUSE: Sunday 6/7 1:00 PM - 3:00 PM
$615,000
4

Beds

2.1

Baths

2,319

Sq.Ft.

1005 CHASE DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 8266 PURPLE SANDPIPER AVENUE Winter Garden, FL MLS# O6411387
  • Recently Listed with Virtual Tour
1 of 57
$639,000
4

Beds

3.0

Baths

2,274

Sq.Ft.

8266 PURPLE SANDPIPER AVENUE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 15806 GEM VIEW ST Winter Garden, FL MLS# A12029648
  • Recently Listed with Virtual Tour
1 of 37
$495,000
2

Beds

2.0

Baths

15806 GEM VIEW ST

Winter Garden, FL

Courtesy of FAST ACTION REALTY INC
View 8016 SWEET ORANGE AVENUE Winter Garden, FL MLS# TB8511160
$549,900
4

Beds

2.1

Baths

2,084

Sq.Ft.

8016 SWEET ORANGE AVENUE

Winter Garden, FL

Courtesy of HOME SOLD REALTY LLC
View 15025 EVERGREEN OAK LOOP Winter Garden, FL MLS# O6410108
  • Recently Listed with Virtual Tour
1 of 44
$510,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

15025 EVERGREEN OAK LOOP

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 11036 ROBERT FROST DRIVE Winter Garden, FL MLS# O6410350
  • Recently Listed with Virtual Tour
1 of 34
$649,990
4

Beds

3.0

Baths

2,136

Sq.Ft.

11036 ROBERT FROST DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 33 TIMBERCREEK PINES CIRCLE Winter Garden, FL MLS# O6408941
  • Recently Listed with Virtual Tour
1 of 29
$562,000
3

Beds

2.0

Baths

1,584

Sq.Ft.

33 TIMBERCREEK PINES CIRCLE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 16186 HONEY HARVEST STREET Winter Garden, FL MLS# O6411495
  • Recently Listed with Virtual Tour
1 of 57
$630,000
4

Beds

3.1

Baths

2,445

Sq.Ft.

16186 HONEY HARVEST STREET

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 17126 ARROWHEAD BOULEVARD Winter Garden, FL MLS# O6409499
$565,000
3

Beds

2.0

Baths

2,114

Sq.Ft.

17126 ARROWHEAD BOULEVARD

Winter Garden, FL

Courtesy of Orlando - WEICHERT, REALTORS® - Hallmark Properties
View 9606 WOODCRANE DRIVE Winter Garden, FL MLS# O6410113
  • Recently Listed with Virtual Tour
1 of 36
$525,000
3

Beds

2.1

Baths

2,101

Sq.Ft.

9606 WOODCRANE DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 46 W VINING STREET Winter Garden, FL MLS# O6408720
  • Recently Listed with Virtual Tour
1 of 40
$549,900
3

Beds

2.0

Baths

1,273

Sq.Ft.

46 W VINING STREET

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 17124 BEACHGRASS ALLEY Winter Garden, FL MLS# O6408024
  • New Construction with Virtual Tour
1 of 4
$559,990
3

Beds

2.1

Baths

1,983

Sq.Ft.

17124 BEACHGRASS ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 14451 WINDSOR HALL WAY Winter Garden, FL MLS# O6408731
$510,000
3

Beds

2.0

Baths

1,814

Sq.Ft.

14451 WINDSOR HALL WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 5443 BOWMAN DRIVE Winter Garden, FL MLS# O6408812
  • Virtual Tour
1 of 73
$649,000
4

Beds

4.1

Baths

2,656

Sq.Ft.

5443 BOWMAN DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 13023 INKWELL ALLEY Winter Garden, FL MLS# O6409443
$515,000
4

Beds

3.0

Baths

2,042

Sq.Ft.

13023 INKWELL ALLEY

Winter Garden, FL

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS 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

1,047

Estimated median home price

$615,000
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 24
$200K - 300K 88
$300K - 400K 80
$400K - 500K 145
$500K - 600K 170
$600K - 700K 129
$700K - 800K 117
$800K - 900K 92
$900K - 1M 72
$1M - Max 129

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 731
Townhouse 139
Condo 137
Commercial 11
Rental 197
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 6/7/2026)

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.

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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 6/7/2026.

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 6/7/2026.

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

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 6/7/2026.