247 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
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
View 15527 SWEET ORANGE AVENUE Winter Garden, FL MLS# O6394429
  • Recently Listed with Virtual Tour
1 of 38
$700,000
3

Beds

3.1

Baths

2,383

Sq.Ft.

15527 SWEET ORANGE AVENUE

Winter Garden, FL

Courtesy of BUYER REBATES REALTY
View 12438 CLEAR SAPPHIRE DRIVE 223 Winter Garden, FL MLS# O6393877
$689,990
4

Beds

4.0

Baths

3,460

Sq.Ft.

12438 CLEAR SAPPHIRE DRIVE 223

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 936 KYLEE ALY Winter Garden, FL MLS# O6393910
  • Recently Listed with Virtual Tour
1 of 60
$675,000
3

Beds

2.1

Baths

1,772

Sq.Ft.

936 KYLEE ALY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 12410 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6393606
  • Recently Listed with Virtual Tour
1 of 54
$639,900
3

Beds

2.0

Baths

1,860

Sq.Ft.

12410 ENCORE AT OVATION WAY

Winter Garden, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 17308 WILD DAISY DRIVE Winter Garden, FL MLS# G5110060
$740,205
6

Beds

4.1

Baths

3,412

Sq.Ft.

17308 WILD DAISY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5948 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5110067
$680,435
3

Beds

3.1

Baths

2,515

Sq.Ft.

5948 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14568 SPOTTED SANDPIPER BOULEVARD Winter Garden, FL MLS# O6392928
  • Recently Listed with Virtual Tour
1 of 37
$599,900
3

Beds

2.0

Baths

1,997

Sq.Ft.

14568 SPOTTED SANDPIPER BOULEVARD

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 16933 OAKBORO STREET Winter Garden, FL MLS# R4910916
  • Recently Listed with Virtual Tour
1 of 32
$560,000
3

Beds

2.1

Baths

2,014

Sq.Ft.

16933 OAKBORO STREET

Winter Garden, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 16277 HONEY HARVEST STREET Winter Garden, FL MLS# O6392350
  • Recently Listed with Virtual Tour
1 of 41
$698,000
4

Beds

4.1

Baths

2,930

Sq.Ft.

16277 HONEY HARVEST STREET

Winter Garden, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 15442 ENCHANTED MELODY WAY Winter Garden, FL MLS# S5146095
  • Recently Listed with Virtual Tour
1 of 37
$629,900
4

Beds

3.0

Baths

2,420

Sq.Ft.

15442 ENCHANTED MELODY WAY

Winter Garden, FL

Courtesy of A & V FLORIDA REALTY GROUP LLC
View 14735 SETON CREEK BOULEVARD Winter Garden, FL MLS# O6392489
$719,900
4

Beds

3.1

Baths

2,665

Sq.Ft.

14735 SETON CREEK BOULEVARD

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 337 SUNSET OAKS RD Winter Garden, FL MLS# O6391526
  • Virtual Tour
1 of 45
$599,900
4

Beds

3.0

Baths

2,186

Sq.Ft.

337 SUNSET OAKS RD

Winter Garden, FL

Courtesy of REAL LIVING R E SOLUTIONS
View 16736 OAKBORO STREET Winter Garden, FL MLS# O6388784
  • Recently Listed with Virtual Tour
1 of 65
$585,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

16736 OAKBORO STREET

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 650 SETTING SUN DRIVE Winter Garden, FL MLS# O6390644
  • Recently Listed with Virtual Tour
1 of 60
$740,000
5

Beds

3.0

Baths

3,605

Sq.Ft.

650 SETTING SUN DRIVE

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 17440 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109764
$688,324
4

Beds

2.1

Baths

2,235

Sq.Ft.

17440 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
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 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

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

953

Estimated median home price

$589,000
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 4
$100K - 200K 15
$200K - 300K 96
$300K - 400K 81
$400K - 500K 155
$500K - 600K 155
$600K - 700K 112
$700K - 800K 92
$800K - 900K 79
$900K - 1M 62
$1M - Max 102

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 646
Townhouse 144
Condo 128
Commercial 11
Rental 221
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 3/27/2026)

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 3/29/2026.

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.

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 3/29/2026.