Bulls don’t typically like to be ridden — but, legend says, that’s how Smithtown came to be. As the story goes, in the mid-1600s, an English settler named Richard Smith rescued the kidnapped daughter of a local Native American chief, possibly part of the Wyandanch tribe. The chief granted Smith as much land as he could encircle in a single day while riding a bull. Smith chose the summer solstice — the longest day of the year — for his ride, and Smithtown was born. It’s a fun story, and even if historians say Smith likely simply bought the land, it’s tinted the lives of residents for centuries. Today, there’s a statue of Smith’s bull, Whisper, at the fork where St. Johnland Road and West Jericho Turnpike meet Main Street. The statue is a beloved member of the community, and locals even decorate it for holidays. “As a child, we always remember that statue,” says Jennifer Nyx, a licensed real estate salesperson at Keller Williams with six years of experience.
Located in a township of the same name, today’s Smithtown has parks and river access for tons of outdoor recreation alongside shopping, restaurants and the infrastructure necessary for an easy commute. “If you want that perfect mix of suburban peace and having fun, that’s definitely the place because it’s really known for its laid-back vibe and charm and there’s so many restaurants and coffee shops and parks,” Nyx says.
It’s these features that draw many homebuyers to the area, including Craig Perry and his wife, Elizabeth. “We explored around several different towns in Suffolk, and we kind of just fell in love with the vibe that Smithtown had in terms of the layout, the school district and the parks,” he says. When they outgrew their house, they found another right in Smithtown. “Right from the get-go, everyone was very warm and welcoming. That’s something that we weren’t expecting, but we were extremely grateful for," Perry says. “It’s hands-down one of the best decisions we made, to move to Smithtown. I couldn’t imagine living anywhere else.”
A statue of Whisper the Bull greets visitors as they enter Smithtown.
Smithtown's gorgeous Town Hall wast built in 1912.
Smithtown features quiet suburbs and a sprawling downtown.
The Smithtown Long Island Rail Road station is convenient option for local commuters.
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Suburban homes and large houses with acreage
Fittingly for an area with so many parks, trees often line Smithtown’s wide residential streets and shade front yards. The homes here range from quaint Cape Cods and more mid-sized ranch-style or split-level homes to sprawling new traditionals. Small fixer-uppers on suburban lots can start in the $500,000 to $600,000 range, but large, updated homes with acreage can soar to $1.5 million. The handful of homes on the river near the coast sell for even more — up to $2.2 million for an updated house with several acres of land. Not every home in Smithtown has extensive acreage, but it’s certainly easy to find. “We’re also kind of noted as horse country,” says Adelle Longo, a licensed real estate salesperson, GRI at Laffey Real Estate who has sold homes here for 25 years. Homes with properties that allow horses can approach waterfront prices, nearing $2 million.
Cozy single family homes are replete throughout Smithtown.
Medium sized ranch inspired homes are quite common in Smithtown.
Newly renovated colonial style homes are one of the many home styles throughout Smithtown.
There are many gorgeous homes sitting on large acreage in Smithtown.
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Miles of hiking trails, kayaking on the Nissequogue River
According to Nyx, the Town of Smithtown has 25 town parks, four state parks and four beaches — a ratio strongly represented in the smaller community of Smithtown. Nature preserves sprawl across Smithtown, following the Nissequogue River as it stretches all the way to the coast, providing miles of hiking and biking trails. “Which is cool, because there’s always places to hike, picnic and also just chill out,” Nyx says. Caleb Smith State Park Preserve is one of the most well-known parks in the entire township, offering 543 acres full of trails and a nature museum. The Nissequogue River is another huge source of outdoor recreation, dotted with spots to launch kayaks and canoes. There’s a golf club and even a vineyard. Less than 6 miles from the center of Smithtown, Short Beach is the closest spot to relax on the sand or cool off in the Sound.
Kayak and fish along the beautiful Nissequogue River in Smithtown.
Take a hike along the many serene paths of Caleb Smith State Park in Smithtown.
Walk the trails of Sweetbriar Park in Smithtown.
Enjoy the peace and quiet of Forestwood Park in Smithtown.
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A growing downtown full of restaurants
West Main Street is lined with businesses, restaurants and bars. Katie’s of Smithtown is one of the most well-known bars in the downtown area — and not just because of its frequent live music performances and karaoke nights. “They’ll claim it’s haunted,” Longo says. “They’ll swear to you it is.”
As much as locals love the little downtown now, Smithtown has plans to improve it. With the help of Tritec — the same company that helmed downtown revitalizations in Patchogue, Lindenhurst and Bay Shore — the plan is to add sewage infrastructure, update storefronts and increase walkability, all while drawing in new shops and restaurants. “The idea is basically to build up around the train station, akin to what was done for Farmingdale and Patchogue,” Perry says. “So I daresay within the next 10 years, it’s going to become an even better place to live, just based off of what it’s going to be for the community and the local businesses.”
Grab a bite to eat at the many restaurants in downtown Smithtown.
Enjoy the day in downtown Smithtown.
Catch a show at the Smithtown Performing Arts Center.
Shop and dine around downtown Smithtown.
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School districts rated among Suffolk County’s best
Most children in Smithtown attend the Smithtown Central School District, which Niche gives an A. Very tiny portions of the city are instead served by the Hauppauge Union Free School District, which has an A, and Kings Park Central School District, which also has an A.
Smithtown High School is ranked 165th within New York State.
Parkview Elementary School has 405 students enrolled.
Accompsett Middle School has a great curriculum for students in Smithtown.
Nesaquake Middle School a student-teacher ratio of 9 to 1.
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Gathering for Smithtown Festival Day
During the summer, Smithtown’s downtown floods with people celebrating Smithtown Festival Day. “They have food trucks, local vendors, plenty of family fun activities. And they close down the main road, and it’s a big deal,” Nyx says, adding that it draws thousands of people.
Commuting by car or LIRR
State Routes 25A, 25 and 111, also called Hauppauge Road, run right through Smithtown, connecting residents to other major roads and highways. For those who work in Manhattan, Smithtown has a Long Island Rail Road Station, but there are no express trains. It takes about an hour and 40 minutes to travel from Smithtown to Penn Station. “You can take also the train to JFK Airport to get you anywhere — to get you anywhere in the world, and you don’t have to drive,” says Jean Gillin, a licensed associate real estate broker at Integrity Core Realty who has lived in Smithtown for 38 years and has been selling homes here for 19 years. “I just got back from California, and it was a piece of cake.” John F. Kennedy International Airport is 44.6 miles away, offering flights to over 195 destinations on six continents. For domestic flights or international flights with connections in larger airports, residents can head to Long Island MacArthur Airport under 10 miles away.
St. Catherine of Siena Hospital is located in Smithtown and Gillin says it serves as a major employer. According to the USCB, 30.5% of residents work in educational services, health care or social assistance. That’s significantly more than retail, which is the next most common job at 12.2%.
Route 25A spans throughout many Long Island neighborhoods and becomes Smithtown's Main Street.
Route 25 is a quick and easy connection from Smithtown to many major highways.
Travel through Long Island quickly and easily via Route 111.
Smithtown's train station is on the Port Jefferson Branch of the Long Island Rail Road.
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Decreasing crime rates, hurricane season
Most crime in Suffolk County’s 4th Precinct, which covers Smithtown, is on a downward trend. Between 2020 and 2021, violent crime dropped by 26.1% and property crime dropped by 8.4%. New York’s GIVE initiative, or Gun Involved Violence Elimination initiative, gave Suffolk County over $1.3 million. Between the first seven months of 2023 and the same period in 2024, the initiative has been credited with bringing shootings in the county down by 50%.
Smithtown experiences all four seasons, often getting snow during the winter. Hurricane season also has the potential to impact the city, often bringing cloudy skies and bouts of rain from June to November even when a storm mostly peters out before reaching the area. Hurricanes themselves only bring a minor risk of flooding to Smithtown, but there is a severe wind factor risk.
Written By
Christina Norwood
Photography Contributed By
Anthony Costa
Video By
Adam Lapallo
Interested in learning more about homes in this area?
Reach out to
Donna Manning Catapano,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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Avalon Commons in Smithtown, NY offers 1, 2, and 3 bedroom apartment homes that include the ultimate in comfort and convenience. These magnificent, newly renovated apartment homes, located in one of Long Island’s most prestigious communities, will entice you in every way. Apartments at Avalon Commons are equipped with a wide range of high quality amenities such as spacious walk-in closets, lofts
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
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