$547,391Average Value$274Average Price per Sq Ft59Homes 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
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On average, homes in Chester, NY sell after 60 days on the market compared to the national average of 56 days. The median sale price for homes in Chester, NY over the last 12 months is $498,500, down 5% from the median home sale price over the previous 12 months.
Rare opportunity in Chester! This 4-bedroom, 3-bath raised ranch sits on a private 2.5-acre lot and features a true 6-car garage — an uncommon and highly desirable feature that sets this home apart. The oversized garage offers exceptional flexibility: perfect for the car enthusiast, contractor, large family, or anyone who needs serious storage, a workshop, or space for boats, RVs, or equipment.
New Pics!Welcome to easy, low-maintenance living in this beautifully maintained 3-bedroom, 2.5-bath condo townhouse offering 1,585 square feet of comfortable living space in a peaceful community. Wake up to tranquil views overlooking a picturesque lake and enjoy the perfect blend of privacy, convenience, and amenities. The bright and spacious layout features central air conditioning, generous
Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests. The generous interior features multiple living
Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the
Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene
Impeccably maintained contemporary raised ranch in Lake Region Estates on prime corner lot, featuring an open floor plan ideal for everyday living and entertaining. Updated kitchen with center island, stainless steel appliances, and a bright garden window perfect for herbs and plants. Spacious living room offers a cathedral ceiling and oversized windows for abundant natural light. Dining area
Beautifully maintained two bedroom condo with a two car garage in an excellent location within the highly desirable Whispering Hills community. Updated kitchen and newer flooring on the main level. Wood burning fireplace in the spacious living room. Sliding door from the dining area to the patio. The primary bedroom with tall vaulted ceilings has a large walk-in closet with custom
Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship.Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming
Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.
Opportunity awaits on this 1.76-acre building lot in the heart of the Adirondacks, just minutes from Gore Mountain. Whether you're dreaming of an affordable year-round home or the perfect basecamp for skiing, hiking, mountain biking, snowmobiling, and everything the Adirondacks have to offer, this property provides an excellent starting point. Existing improvements include electric service, as
North Gore Lot - Come build your dream on home this 3.6 acre wooded lot with power available roadside and perc test completed. Secluded location, yet only 15 minutes to Gore Mountain and 10 minutes to Minerva Beach with abundant outdoor recreation opportunities.
Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of
Rare opportunity to own approximately 46 acres in the desirable Black Meadow Road area of Chester, New York. Tucked privately behind a subdivision entrance at the end of a cul-de-sac, this parcel offers a peaceful natural setting surrounded by mature woods, wetlands, scenic surroundings, and abundant wildlife. Ideal for recreational use including hiking, hunting, nature walks, bird watching,
Escape to the mountains with this beautiful 20-acre property in Chester, NY, ideally situated along a year-round maintained town road. The terrain gently climbs from the road, leading to multiple APA-approved building sites for an off-grid cabin or hunting camp offering excellent privacy in a quiet woodland setting. The property features a healthy forest of Northern hardwoods including maple,
Come see this mixed use residential and commercial property for rent. Enjoy the benefits of working from home as you can have your business in the same home. 3 bed 3 bath home in Chester. Enjoy the ample amount of parking available, fitting well over 10 cars on your lot. Call today for a showing
Welcome to the desirable Pine Hollow Complex in Chester! This spacious one-bedroom, one-bath residence offers a bright, open-concept floor plan filled with natural light, creating a warm and inviting atmosphere. The open living area features a gas fireplace and central air conditioning, providing comfort throughout every season. The generously sized bedroom offers generous closet space, while a
The advertised rate of $16,528/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 11, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
Rare rental opportunity to occupy a premier estate in Chester. This property is perfectly suited for those seeking a self-sufficient lifestyle without sacrificing modern luxury. The 4-bedroom, 3-bath custom home is complemented by expansive grounds crisscrossed with miles of private horse trails and a thriving, mature fruit orchard. Practicality meets scale with an infrastructure designed for
Welcome to this well-maintained 2-bedroom, 1 bath townhouse located in Whispering Hills. This unit features an open layout with laminate flooring throughout the main living areas. The living room includes a fireplace and a slider to your own private deck. Enjoy a functional kitchen and dining room that makes everyday living and hosting a breeze. Down the hallway an updated bathroom and two
Monroe, NY - Spacious, two-level townhouse end unit. First floor features living room/dining area, kitchen with dinette area, half bath, laundry room & garage. Top level contains master bedroom suite with full bath & walk-in closet, second bedroom, third bedroom, second full bathroom and hallway walk-in closet. Additional features: Young carpeting, entry way flooring, butcher block counter top &
CURRENT TENANTE IS SEEKING A ROOMMATE. Looking to rent a fully furnished 1 bedroom 1 bath. This is within the 3 bedroom unit and common area/kitchen will be shared with the owner. This is a fully air conditioned unit. This would be a month-to-month tenancy and owner is very flexible. Assigned parking spot is available with access to the swimming pool, common area and gym. Located in Chester, NY
Welcome to Kings Estates! This updated end-unit townhome offers the perfect combination of comfort, style, and convenience. Featuring 3 bedrooms and 2.5 bathrooms, this move-in-ready home showcases an updated kitchen with newer appliances, hardwood floors throughout, and a thoughtfully finished basement that provides additional living and entertaining space. The spacious backyard is a true
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