$544,380Average Value$267Average Price per Sq Ft32Homes For Sale
The rural town of Chester birthed Philadelphia cream cheese
The town of Chester began as a dairy farming village in the early 19th century and is now known as an expansive, park-heavy rural community just minutes away from Hudson Valley attractions and retail centers in neighboring Woodbury. There are options for small-town single-family homes, as well as larger farmhouses on multi-acre lots. “People like the location on Route 17, a major artery, and home prices are a little lower compared to towns like Monroe and other places in the county,” says Chris Staritz, an associate broker with Howard Hanna Rand Realty with 13 years of experience. Chester’s history in the dairy industry has left a global impact, as the town is also known as the birthplace of world-famous Philadelphia-style cream cheese.
Originally a dairy farming village in the early 19th century, Chester has evolved into a scenic, park-filled rural town with convenient access to Hudson Valley attractions.
Chester’s dairy legacy has made it recognized as the birthplace of the world-famous Philadelphia-style cream cheese and the town still hosts a variety of farms.
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Diverse options for recreation in Chester
The family-friendly Castle Fun Center is an amusement park within Chester. It features carnival rides, a mini golf course, a go-kart track, an indoor roller-skating rink and an arcade. Carpenter Community Park is the town’s central green space, with a playground, picnic pavilion, basketball and bocce courts, and a baseball field that regularly hosts Chester Little League tournaments. Carpenter Park is steps away from the Jarvis Boone Memorial Amphitheater, where locals can bring chairs and watch live outdoor performances. Goosepond Mountain State Park stretches 1,500 acres in Chester and has three miles of trails for hiking or horseback riding across mountainsides and wetlands. The paved Orange Heritage Trail runs almost 20 miles through the county and is accessible from Chester’s Erie Depot, a historic train station that is now a museum.
Chester offers a variety of recreational attractions for families, such as the Castle Fun Center and its popular go-kart track.
At the heart of town, Carpenter Community Park serves as Chester’s central green space and regularly hosts Chester Little League games.
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Hudson Valley attractions close to home
Legoland is five miles west of Chester in the neighboring town of Goshen. This regional attraction hosts seven theme parks and an immersive resort-style hotel. Capelli Sports Complex is a new athletic center in town, with soccer fields, baseball and softball diamonds, and indoor courts for volleyball, pickleball or basketball. The Chester Erie Depot is a museum and historic landmark in town. In the early 1840s, it served as a commercial station where dairy farmers would ship their fresh milk to New York City. Today, the rail bed has been converted into the Orange Heritage Trail.
Just five miles west of Chester, Legoland New York is a major regional attraction featuring seven themed lands and an immersive resort-style hotel.
The Chester Erie Depot, originally a bustling commercial station in the 1840s, is now a museum and historic landmark.
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Local Chester markets and outlet shopping in Woodbury
At Chester Mall, locals can head to ShopRite for groceries or catch the latest hit movies at Flagship Premium Cinemas. There’s also the Chester Agricultural Center, providing farm-fresh produce from a network of regional farms. Rustic Wheelhouse Restaurant is a popular local spot for Italian food, from brick-oven margarita pizzas to parmesan-crusted cod and homemade pasta dishes. A 9-mile drive east leads to Woodbury Common Premium Outlets, with 250 name-brand retailers, including Old Navy, Nike and Calvin Klein.
For locally sourced food, the Chester Agricultural Center offers farm-fresh produce from a collective of regional farms, supporting sustainable agriculture and healthy living.
Woodbury Common Premium Outlets is just a 9-mile drive east, featuring 250 name-brand retailers, including Old Navy, Nike, and Calvin Klein.
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Small-town homes and a significant land market
Most homes were built from the 1960s through the early 2000s, ranging from $400,000 to $1 million, varying by age, square footage and lot size. “There are a lot of older homes, [usually] on the small side, not big homes like in Goshen and Warwick,” says Staritz. “There’s also a substantial condo complex, and a lot of the commuters around town live there. Within the village of Chester are brick ranch-style homes and midcentury split-levels and bilevels along organized, suburban streets with moderate tree cover. Larger contemporary and Craftsman-style homes and Colonial Revivals sit on 1-acre lots or more outside the town. Undeveloped multi-acre lots are available from $50,000 to $500,000. The Windridge Mews condo subdivision is in the southeast corner of Chester. The condos often have two to three bedrooms.
Large contemporary homes are often found on spacious one-acre lots amid rolling farmland in Chester.
Anyone looking for a midcentury split-level home will find plenty of options in Chester.
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After school activities for Chester schoolchildren
The Chester Union Free School District serves the town for education. Students can attend Chester Elementary, rated a B on Niche, and Chester Academy, rated a B-minus, which teaches grades 6 through 12. Chester Elementary offers the Healthy Kids Before and After School Program, engaging students with activities such as social games, yoga, reading and STEM workshops.
Chester Elementary School holds a B rating on Niche.
Students from Chester finish their education at Chester Academy, which serves grades 6–12 and is rated B-minus by Niche.
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Newark and New York City are an hour and a half away
Commuters can take Interstate 87 just 62 miles south to reach New York City or Newark in an hour and a half. Coach USA buses stop along Brookside Avenue for commuter access around the Hudson Valley.
Written By
Maxwell Olarinde
Photography Contributed By
Jerome Strauss
Video By
Christian Gortler
Interested in learning more about homes in this area?
Reach out to
Joan Wortmann,
an experienced agent in this area.
On average, homes in Chester, NY sell after 69 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, NY over the last 12 months is $526,000, up 12% from the median home sale price over the previous 12 months.
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