870 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 205 SURPRISE DRIVE Winter Garden, FL MLS# O6365188
$1,200,000
4

Beds

2.1

Baths

2,171

Sq.Ft.

205 SURPRISE DRIVE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 7389 JOHN HANCOCK DRIVE Winter Garden, FL MLS# O6379851
$1,200,000
5

Beds

3.1

Baths

4,006

Sq.Ft.

7389 JOHN HANCOCK DRIVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 9312 HOLLISTON CREEK PLACE Winter Garden, FL MLS# S5143665
$1,200,000
4

Beds

3.1

Baths

3,077

Sq.Ft.

9312 HOLLISTON CREEK PLACE

Winter Garden, FL

Courtesy of K REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 156 STANTON ESTATES CIRCLE Winter Garden, FL MLS# O6384801
  • Recently Listed with Virtual Tour
1 of 62
$1,200,000
4

Beds

4.0

Baths

3,170

Sq.Ft.

156 STANTON ESTATES CIRCLE

Winter Garden, FL

Courtesy of FATHOM REALTY FL LLC
View 617 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6389100
$1,200,000
4

Beds

4.1

Baths

3,624

Sq.Ft.

617 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 17588 LAKE STAR ROAD Winter Garden, FL MLS# O6387269
  • Recently Listed with Virtual Tour
1 of 57
$1,195,000
5

Beds

4.0

Baths

4,026

Sq.Ft.

17588 LAKE STAR ROAD

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 14355 BLACK LAKE PRESERVE STREET Winter Garden, FL MLS# O6368562
$1,190,000
6

Beds

5.0

Baths

5,296

Sq.Ft.

14355 BLACK LAKE PRESERVE STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 430 COURTLEA OAKS BOULEVARD Winter Garden, FL MLS# O6385851
  • Recently Listed with Virtual Tour
1 of 54
OPEN HOUSE: Saturday 3/14 12:00 PM - 2:00 PM
$1,190,000
3

Beds

2.1

Baths

2,163

Sq.Ft.

430 COURTLEA OAKS BOULEVARD

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 17335 GLOSSY POMELO WAY Winter Garden, FL MLS# O6365223
  • New Construction with Virtual Tour
1 of 16
$1,189,990
5

Beds

4.1

Baths

4,780

Sq.Ft.

17335 GLOSSY POMELO WAY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 16611 TOCCOA ROW Winter Garden, FL MLS# O6314995
$1,180,000
5

Beds

4.2

Baths

4,685

Sq.Ft.

16611 TOCCOA ROW

Winter Garden, FL

Courtesy of A2Z GLOBAL REALTY LLC
View 308 FOREST HAVEN DRIVE Winter Garden, FL MLS# O6376492
$1,180,000
4

Beds

2.1

Baths

3,534

Sq.Ft.

308 FOREST HAVEN DRIVE

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 64 N PARK AVENUE Winter Garden, FL MLS# O6385285
  • Recently Listed
1 of 38
$1,179,000
4

Beds

4.0

Baths

2,225

Sq.Ft.

64 N PARK AVENUE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 15312 GILLIGAN COURT Winter Garden, FL MLS# O6372954
$1,175,000
5

Beds

4.1

Baths

3,652

Sq.Ft.

15312 GILLIGAN COURT

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 10067 AUSTRINA OAK LOOP Winter Garden, FL MLS# O6361968
$1,170,000
6

Beds

5.0

Baths

4,305

Sq.Ft.

10067 AUSTRINA OAK LOOP

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 5365 BOWMAN DRIVE Winter Garden, FL MLS# O6383338
$1,150,000
4

Beds

3.1

Baths

4,000

Sq.Ft.

5365 BOWMAN DRIVE

Winter Garden, FL

Courtesy of FORTERA REALTY LLC
View 16071 BARKLY RIDGE COURT Winter Garden, FL MLS# O6390569
  • Recently Listed with Virtual Tour
1 of 14
$1,150,000
4

Beds

3.0

Baths

2,986

Sq.Ft.

16071 BARKLY RIDGE COURT

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15267 MARITIME PINE DRIVE Winter Garden, FL MLS# G5103775
$1,149,565
6

Beds

4.0

Baths

3,907

Sq.Ft.

15267 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17661 DAVENPORT ROAD Winter Garden, FL MLS# O6350509
$1,149,000
3

Beds

3.0

Baths

2,400

Sq.Ft.

17661 DAVENPORT ROAD

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY
View 15625 SYLVESTER PALM DRIVE Winter Garden, FL MLS# O6379346
$1,120,000
5

Beds

4.1

Baths

3,886

Sq.Ft.

15625 SYLVESTER PALM DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 7832 FREESTYLE LANE Winter Garden, FL MLS# G5107680
$1,100,000
4

Beds

3.0

Baths

2,650

Sq.Ft.

7832 FREESTYLE LANE

Winter Garden, FL

Courtesy of DENIZ REALTY PARTNERS LLC

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

935

Estimated median home price

$590,000
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

PriceCount
$0 - 100K4
$100K - 200K11
$200K - 300K91
$300K - 400K79
$400K - 500K152
$500K - 600K158
$600K - 700K108
$700K - 800K94
$800K - 900K72
$900K - 1M59
$1M - Max107

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family639
Townhouse134
Condo125
Commercial11
Rental221
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 3/14/2026)

Information deemed reliable but not guaranteed.

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 3/14/2026.

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

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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 3/14/2026.

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 3/14/2026.