Former citrus farming town transformed into bustling suburban city
As late as the 1990s, the city of Winter Garden was mainly citrus groves and winding roads. "When you drove with your windows down, you'd smell all the orange blossoms. It was wonderful," says Jamie Ampel, a Winter Garden native and owner of All Sellers & Buyers Realty, which sells throughout the Orlando area. Today, housing developments have replaced the citrus groves and its 47,000 residents work in industries unrelated to agriculture. AdventHealth, one of Central Florida's largest hospitals, has a location in Winter Garden, and the city is less than miles from Walt Disney World's theme parks—close enough that the city is home to many Disney cast members. Three major highways run through the city, allowing easy commutes to downtown Orlando, about 15 miles away, and the rest of the metro area.
Winter Garden has expanded its downtown with more shopping and dining, and it's become a popular area for local events. Other draws to the city include a robust trail system and well-rated schools. "Winter Garden offers a lot to people of all demographics: single people, families, older folks. There really is something for everybody," Ampel says.
As of 2025, Winter Garden has 47,000 residents in non-agricultural jobs.
AdventHealth, one of Central Florida's largest hospitals, has a Winter Garden location.
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Housing ranges from 1920s bungalows to modern lakefront estates
Winter Garden is overwhelmingly suburban, with homes on landscaped lawns set along quiet streets. Most neighborhoods feature sidewalks, making them highly walkable, and those living close to downtown can easily stroll to shops and restaurants. Homes near downtown are primarily bungalows and ranch-style homes from the first half of the 20th century. New Traditional homes built in the 1990s and 2000s are scattered throughout the city but are concentrated south of Florida's Turnpike in gated communities like Stoneybook West. Homes along Lake Apopka and Johns Lake boast water views and can cost $1 million or more, much higher than the city's median price of $576,000. There are also a number of townhouses in the city, which have a median price of around $450,000. Condos are also available in complexes on the city's north side.
Winter Garden is a suburban area, with homes on landscaped lawns along quiet streets.
Homes near downtown Winter Garden are primarily bungalows.
Homes along Lake Apopka and John's Lake in Winter Garden may cost $1 million or more.
Townhouses are found throughout Winter Garden, with a median price of $450,000.
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Well-rated Orange County Public School District
The city is served by the Orange County Public School District, which gets an A-minus on Niche and spans much of the greater Orlando area. It offers school choice and includes just over 200 schools. Of the schools in Winter Garden, A-rated West Orange High provides dual enrollment opportunities at one of the county's Tech Centers, where students earn college credits or industry certification in fields like photography, game design, cosmetology or welding.
West Orange High School offers dual enrollment for students in Winter Garden.
Winter Garden is served by Orange County Public Schools, rated A- on Niche.
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Hiking and biking through the West Orange Trail
Winter Garden has several parks, seasonal outdoor pools and recreation centers, and it also offers opportunities to get out into nature. The 22-mile paved West Orange Trail threads through downtown Winter Garden along old railroad alignments and runs into nearby Apopka. Newton Park features a tranquil boardwalk along the banks of Lake Apopka, near playgrounds and boat launch points. Veterans Memorial Park has baseball and pickleball facilities where adult and youth leagues practice. The West Orange Country Club is in the city's south end and offers its members an 18-hole golf course and tennis courts.
Winter Garden offers parks, seasonal pools, and nature opportunities.
The 22-mile paved West Orange Trail runs through downtown Winter Garden.
Newton Park features a tranquil boardwalk along Lake Apopka in Winter Garden.
Winter Garden residents enjoy walking the tranquil boardwalk at Newton Park.
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Shopping and dining downtown;15 miles from Orlando and Disney World
Downtown Winter Garden has grown from a few local stores to a popular destination for dining out, grabbing coffee and shopping at local boutiques. The walkable stretch of Plant Street includes city hall, the police department and the post office. There's also the SOBO Gallery, run by the Winter Garden Art Association, which offers art classes. State Road 50, also known as West Colonial Drive, is lined with national retailers, including grocery stores, chain restaurants, gas stations and banks. Nearby Orlando offers more shopping, dining, culture and entertainment options. Disney's theme parks and Universal Studios Florida are similarly close.
AdventHealth Winter Garden Hospital sits near Route 429, and other medical and dental offices are scattered throughout the city. Nearby Ocoee has more medical centers, including Orlando Health Hospital.
Downtown Winter Garden has grown from a few local stores to a popular destination for shopping.
The Winter Garden Art Association operates the SOBO Gallery, offering art classes.
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Farmers market and festivals in Winter Garden
Downtown Winter Garden draws locals with its many year-round events. Over 100 vendors gather every Saturday to sell locally grown produce and homemade goods at the Winter Garden Farmers Market. As a part of the annual Arts in April celebration held by the Winter Garden Art Association, attendees visit free art exhibitions, contests and workshops all month. In February, the Winter Garden Music Festival offers free outdoor concerts all day on multiple stages and outdoor dining at downtown restaurants. December is full of Christmas events, including Light Up Winter Garden, when the lights on the tree at City Hall are illuminated, and the Winter Garden Christmas Golf Cart Parade, where residents drive their elaborately decorated carts down West Plant Street.
The Winter Garden Farmers Market is held Saturdays, 8AM-1 PM, year round.
Winter Garden residents enjoy shopping locally at the weekly farmers market.
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Residents close to many highways, including Florida's Turnpike
West Colonial Drive, Route 429, Florida's Turnpike and Route 408 run through or near the city. "All these new highways have made it easy to get around," Ampel says. "Say you live in Winter Garden but work in Sanford; it's not a crazy commute anymore. You can just hop on 429, and you'll be there in like 20 minutes." For public transportation, the Lynx bus line has stops along West Colonial Drive and connects to Downtown Orlando. Orlando International Airport is about 25 miles via Florida's Turnpike; Orlando Sanford International Airport is about 40 miles via Route 429.
A look at Winter Garden's crime and weather
According to the most recent FBI data, in 2020, the Winter Garden Police Department reported 572 incidents of violent crime and 815 incidents of property crime, significantly lower than the state averages for both. The city's police department offers vacation house checks for out-of-town residents and a citizens' police academy, a free, nine-week course that gives residents a look into how the department is run.
As seen with Hurricane Helene and Hurricane Milton in 2024, storms can bring flooding and high winds despite Winter Garden's location inland.
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
