Overview
$711,285
Average Sales Price
$607,550
Median Sales Price
57,340
Population
935
Total Listings
Discover Life in Winter Garden with Lyndin Wasson
Local Perspective
If I were walking a client through Winter Garden, I’d point out right away how this area has managed to keep its historic charm while embracing the conveniences of modern living. From my experience as a local broker, Winter Garden stands out for buyers who want that classic Florida small-town feel but don’t want to be too far from the pulse of Orlando’s growth. I often recommend Winter Garden to clients seeking a true sense of community—where neighbors know each other, local businesses thrive, and the pace feels just right. It’s an area that attracts those who value character, walkability, and a vibrant downtown, but also appreciate the stability and steady appreciation of a well-established market.
Neighborhood Highlights
Winter Garden’s atmosphere is a blend of historic charm and contemporary energy. The heart of the area, with its brick-lined streets and lovingly restored buildings, gives off a welcoming, almost storybook feel—especially on weekends when the farmer’s market is buzzing. What sets Winter Garden apart from nearby neighborhoods is its commitment to preserving its heritage while supporting new shops, eateries, and cultural events. The West Orange Trail weaves through the area, encouraging an active, outdoor lifestyle, while the downtown district is lively but never overwhelming. It’s a place where families, young professionals, and retirees all find their rhythm—whether that’s catching a show at the Garden Theatre or enjoying a sunset stroll by Lake Apopka.
Homes & Architecture
Winter Garden offers a refreshing mix of home styles. You’ll find everything from lovingly restored early-20th-century bungalows and craftsman cottages near downtown, to newer, master-planned communities with spacious single-family homes and townhouses on the outskirts. Many properties feature inviting front porches, mature trees, and layouts designed for both entertaining and everyday comfort. It’s common to see open-concept living spaces, updated kitchens, and flexible rooms that can serve as home offices or playrooms. The architectural character varies, but there’s a consistent sense of pride in ownership and attention to detail that’s hard to miss as you drive or walk through the neighborhoods.
Featured Listings
For Sale (895)
For Sold (16023)
Open Sat 11AM-1PM4 Beds3 Baths2,274 SqFt8154 COMMON TEAL CT, Winter Garden, FL 34787
Listed by Suad Hai LUXE HUNTER REAL ESTATE
Open Sat 12AM-3PM3 Beds3 Baths1,875 SqFt7183 SUMMERLAKE GROVES ST, Winter Garden, FL 34787
Listed by Ken Pozek REAL BROKER, LLC
Open Sat 1PM-4PM4 Beds3 Baths2,717 SqFt11390 BOURBON ROSE CIR, Winter Garden, FL 34787
Listed by Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC
Open Sat 11AM-2PM3 Beds3 Baths1,908 SqFt9279 GRAND ISLAND WAY, Winter Garden, FL 34787
Listed by Marlene De Cespedes DOUGLAS ELLIMAN
Open Sat 10AM-1PM5 Beds5 Baths3,555 SqFt728 GARDEN WEST TER, Winter Garden, FL 34787
Listed by Danielle Norvell REGENCY REAL ESTATE LLC
Open Tue 10AM-6PM4 Beds4 Baths3,077 SqFt17590 JAPONICA BLOOM DR, Winter Garden, FL 34787
Listed by Abigail Belchick OLYMPUS EXECUTIVE REALTY INC
Amenities & Attractions
Educational Environment
Elementary Schools (16)Middle Schools (10)High Schools (7)
Name
Category
Grades
Library
Ratio
9/10
Maxey Elementary School
1100 E Maple St, Winter Garden, FL 34787
Public
PK - 5
No
14:1 STUDENTS/TEACHERS
9/10
Hope Charter
1550 E Crown Point Rd, Ocoee, FL 34761
Public
KG - 8
No
14:1 STUDENTS/TEACHERS
9/10
Whispering Oak Elementary School
15300 Stoneybrook West Pkwy, Winter Garden, FL 34787
Public
PK - 5
No
15:1 STUDENTS/TEACHERS
8/10
Tildenville Elementary School
1221 Brick Rd, Winter Garden, FL 34787
Public
PK - 5
No
16:1 STUDENTS/TEACHERS
5/10
Montessori of Winter Garden Charter
855 E Plant St, Winter Garden, FL 34787
Public
KG - 8
No
15:1 STUDENTS/TEACHERS
Show More
Demographics
Data provided by Attom Data
Population
Employment
Population
57.3K
57.3K in 2020
Density
636.8
per square mile
Households
20.4K
Total households
Gender
48% / 52%
Men Vs Women
Occupancy
74% / 26%
Owned Vs Rented
Age Median: Years
Education Level
Winter Garden Living: Your Top Local Questions Answered
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
What Home Styles Are Common in Winter Garden?
Winter Garden features a mix of single-family homes, townhomes, and some condos. You’ll find both newer developments and established neighborhoods, with a variety of architectural styles to suit different preferences.
How Convenient Is the Commute From Winter Garden?
Is Winter Garden Walkable and What’s the Lifestyle Like?
How Fast Do Homes Sell in Winter Garden?
What Should I Know About Winter Garden Schools?
Are There HOA Fees or Community Guidelines?
