945 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 14501 GROVE RESORT AVE 3621 Winter Garden, FL MLS# O6388749
  • Recently Listed with Virtual Tour
1 of 30
$224,900
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVE 3621

Winter Garden, FL

Courtesy of GENSTONE REALTY
View 14501 GROVE RESORT AVENUE 1732 Winter Garden, FL MLS# O6388585
$199,900
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1732

Winter Garden, FL

Courtesy of GENSTONE REALTY
View 17090 HAGGERTY HOLLOW ESTATE Winter Garden, FL MLS# G5109783
$1,130,987
6

Beds

4.1

Baths

3,412

Sq.Ft.

17090 HAGGERTY HOLLOW ESTATE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 17446 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109788
$723,200
4

Beds

2.1

Baths

2,688

Sq.Ft.

17446 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7532 SPRING VALLEY STREET Winter Garden, FL MLS# G5109790
$615,990
4

Beds

3.1

Baths

2,520

Sq.Ft.

7532 SPRING VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17156 INGRAM BLUFF DRIVE Winter Garden, FL MLS# G5109791
$606,440
4

Beds

3.0

Baths

2,102

Sq.Ft.

17156 INGRAM BLUFF DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13331 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5109796
  • New Construction with Virtual Tour
1 of 53
$428,405
3

Beds

2.1

Baths

1,644

Sq.Ft.

13331 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 243 ZACHARY WADE STREET Winter Garden, FL MLS# O6391909
  • Recently Listed
1 of 54
$1,398,500
5

Beds

3.1

Baths

3,097

Sq.Ft.

243 ZACHARY WADE STREET

Winter Garden, FL

Courtesy of REGENCY REAL ESTATE LLC
View 8122 RED STOPPER LANE Winter Garden, FL MLS# O6391514
  • Recently Listed with Virtual Tour
1 of 59
OPEN HOUSE: Sunday 3/22 12:00 PM - 2:00 PM
$435,000
3

Beds

2.1

Baths

1,784

Sq.Ft.

8122 RED STOPPER LANE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 7701 SUMMERLAKE POINTE BOULEVARD Winter Garden, FL MLS# O6391690
  • Recently Listed with Virtual Tour
1 of 63
$2,350,000
5

Beds

5.0

Baths

4,072

Sq.Ft.

7701 SUMMERLAKE POINTE BOULEVARD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 503 FIRST CAPE CORAL DRIVE Winter Garden, FL MLS# O6381166
$564,000
4

Beds

2.0

Baths

2,365

Sq.Ft.

503 FIRST CAPE CORAL DRIVE

Winter Garden, FL

Courtesy of REGENCY REAL ESTATE LLC
View 15528 BLACKBEAD STREET Winter Garden, FL MLS# O6390461
  • Recently Listed with Virtual Tour
1 of 63
$465,000
3

Beds

2.1

Baths

1,861

Sq.Ft.

15528 BLACKBEAD STREET

Winter Garden, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 9972 PALLIDA HICKORY WAY Winter Garden, FL MLS# O6391384
  • Recently Listed with Virtual Tour
1 of 42
$559,900
3

Beds

2.1

Baths

2,082

Sq.Ft.

9972 PALLIDA HICKORY WAY

Winter Garden, FL

Courtesy of VESTI LLC
View 13001 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6391387
  • Recently Listed with Virtual Tour
1 of 55
$750,000
4

Beds

3.1

Baths

2,858

Sq.Ft.

13001 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 14748 FIELD DAISY DRIVE Winter Garden, FL MLS# O6391410
  • Recently Listed with Virtual Tour
1 of 44
$614,000
4

Beds

4.1

Baths

2,149

Sq.Ft.

14748 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 14736 FIELD DAISY DRIVE Winter Garden, FL MLS# O6391435
  • Recently Listed with Virtual Tour
1 of 43
$596,832
3

Beds

3.1

Baths

2,149

Sq.Ft.

14736 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 14780 FIELD DAISY DRIVE Winter Garden, FL MLS# O6391463
  • Recently Listed with Virtual Tour
1 of 46
$704,118
4

Beds

4.1

Baths

2,441

Sq.Ft.

14780 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 17060 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5109737
  • Recently Listed with Virtual Tour
1 of 7
OPEN HOUSE: Sunday 3/22 1:00 PM - 4:00 PM
$819,391
6

Beds

4.1

Baths

3,117

Sq.Ft.

17060 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17066 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5109739
  • Recently Listed
1 of 1
OPEN HOUSE: Sunday 3/22 1:00 PM - 4:00 PM
$765,377
4

Beds

3.0

Baths

3,038

Sq.Ft.

17066 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17416 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109744
$784,490
4

Beds

2.1

Baths

2,688

Sq.Ft.

17416 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE 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

941

Estimated median home price

$588,900
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 4
$100K - 200K 12
$200K - 300K 92
$300K - 400K 79
$400K - 500K 153
$500K - 600K 160
$600K - 700K 111
$700K - 800K 91
$800K - 900K 74
$900K - 1M 60
$1M - Max 105

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 644
Townhouse 135
Condo 126
Commercial 11
Rental 229
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 3/18/2026)

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 3/22/2026.

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 3/22/2026.

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 3/22/2026.