View 16933 OAKBORO STREET Winter Garden, FL MLS# R4910916
$560,000
3

Beds

2.1

Baths

2,027

Sq.Ft.

16933 OAKBORO STREET

Winter Garden, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 15442 ENCHANTED MELODY WAY Winter Garden, FL MLS# S5146095
$609,850
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 16736 OAKBORO STREET Winter Garden, FL MLS# O6388784
$563,900
4

Beds

3.1

Baths

2,477

Sq.Ft.

16736 OAKBORO STREET

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
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 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
$556,000
4

Beds

2.0

Baths

2,365

Sq.Ft.

503 FIRST CAPE CORAL DRIVE

Winter Garden, FL

Courtesy of REGENCY REAL ESTATE LLC
View 9972 PALLIDA HICKORY WAY Winter Garden, FL MLS# O6391384
$559,900
3

Beds

2.1

Baths

2,082

Sq.Ft.

9972 PALLIDA HICKORY WAY

Winter Garden, FL

Courtesy of VESTI LLC
View 14748 FIELD DAISY DRIVE Winter Garden, FL MLS# O6391410
  • New Construction with Virtual Tour
1 of 44
$600,000
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
  • New Construction with Virtual Tour
1 of 43
$550,000
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
  • New Construction with Virtual Tour
1 of 46
$700,000
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 15197 BLUE PEACOCK LANE Winter Garden, FL MLS# O6390611
$704,900
3

Beds

2.1

Baths

2,440

Sq.Ft.

15197 BLUE PEACOCK LANE

Winter Garden, FL

Courtesy of KICANTO REALTY
View 17054 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5109477
$688,324
4

Beds

2.1

Baths

2,235

Sq.Ft.

17054 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17055 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5109480
$580,682
4

Beds

3.0

Baths

2,102

Sq.Ft.

17055 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17144 INGRAM BLUFF DRIVE Winter Garden, FL MLS# G5109520
$605,455
4

Beds

3.1

Baths

2,520

Sq.Ft.

17144 INGRAM BLUFF DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1209 CASTLEPORT ROAD Winter Garden, FL MLS# O6390760
$659,000
5

Beds

3.0

Baths

2,812

Sq.Ft.

1209 CASTLEPORT ROAD

Winter Garden, FL

Courtesy of THE PROPERTY STOP LLC
View 16126 PARKWYN STREET Winter Garden, FL MLS# O6389811
$609,000
4

Beds

3.0

Baths

2,372

Sq.Ft.

16126 PARKWYN STREET

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 2230 ROMANUM DRIVE Winter Garden, FL MLS# O6389947
$565,000
4

Beds

4.0

Baths

2,562

Sq.Ft.

2230 ROMANUM DRIVE

Winter Garden, FL

Courtesy of SELECTA REALTY LLC
View 12566 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6389532
$609,900
4

Beds

3.0

Baths

2,420

Sq.Ft.

12566 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 4624 PRAIRIE CREEK STREET Winter Garden, FL MLS# S5145370
$614,900
4

Beds

3.1

Baths

2,459

Sq.Ft.

4624 PRAIRIE CREEK STREET

Winter Garden, FL

Courtesy of FLORIDA SPIRIT HOMES

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

PriceCount
$0 - 100K1
$100K - 200K24
$200K - 300K88
$300K - 400K80
$400K - 500K145
$500K - 600K170
$600K - 700K129
$700K - 800K117
$800K - 900K92
$900K - 1M72
$1M - Max129

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family731
Townhouse139
Condo137
Commercial11
Rental197
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 6/7/2026)

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 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.