$539,139Average Value$271Average Price per Sq Ft34Homes 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
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On average, homes in Chester, NY sell after 59 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 $500,000, up 3% from the median home sale price over the previous 12 months.
Welcome to 4508 Whispering Hills, a well-maintained and thoughtfully updated 2-bedroom, 1.5-bath home offering comfort and convenience. Recent upgrades include an updated kitchen and bathrooms, hardwood floors, a newer sliding glass door, garage door with opener, and an upgraded furnace, providing peace of mind for the next owner. The home features a one-car garage and a practical layout that
Welcome to 4508 Whispering Hills, a well-maintained and thoughtfully updated 2-bedroom, 1.5-bath home offering comfort and convenience. Recent upgrades include an updated kitchen and bathrooms, hardwood floors, a newer sliding glass door, garage door with opener, and an upgraded furnace, providing peace of mind for the next owner. The home features a one-car garage and a practical layout that
Motivated Seller!! Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular
Welcome to 65 Oxford Springs Road, Chester, NY a custom-built Country Contemporary set on a private, 2.3-acre hilltop. This property offers the perfect mix of privacy, space, and convenience, all just minutes from the NYS Thruway, local state parks, and about 50 minutes from NYC. Inside, the home features a bright, open floor plan with plenty of natural light. You’ll find rich hardwood floors,
Exquisite 4 bedroom 3 bath colonial , timeless grandeur meets modern luxury nestled gracefully on a private cul de sac. Amidst meticulously manicured grounds, this colonial style home offers an unparalleled blend of classic elegance and contemporary comfort, from the moment you approach the stately wrought iron fenced property and are greeted by a wrap around porch, you are welcomed by a grand
MONROE WOODBURY SCHOOLS! BRAND NEW KITCHEN! ABSOLUTE MUST SEE!Welcome to your dream home in the highly sought-after Monroe Woodbury School District. Privately set at the end of a long driveway on just under one acre, this beautifully renovated Colonial offers an incredible balance of peace, privacy, and recent upgrades.From the moment you step inside, you are greeted by a stunning foyer that
ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC
Welcome to your dream home at 108 Pine Hill Rd, Chester, NY, where comfort meets elegance in a spacious single-family abode. This charming home offers a thoughtfully designed layout, featuring a welcoming kitchen with direct outdoor access, perfect for morning coffees or entertaining. The first floor also hosts a cozy living room and a bright family room, both filled with natural light. Upstairs,
Discover refined living at 3 Grand View Terrace, a beautiful 6-bedroom, 3-bath Colonial in Chester's sought-after Valley View Phase II subdivision. This impressive home boasts 3,066 sq ft of living space, with a full walkout basement and an attached 2-car garage. Built in 2003, it features central air and forced air heat. Relax by the fireplace or enjoy the outdoor space on the 0.55-acre lot.
10+ Acre recreational vacation location in the Town of Chester. Private maintained road with nice camps and homes. The lot feels as if its set in the heart of a wildlife preserve. Small non salvageable cabin on the property that had electric to the site. 6 miles to North Creek the home of Gore Mountain Ski Center. Build your vacation home here in the Adirondacks.
Set on 10 private acres with sweeping mountain views from nearly every room, 69 Cedar Pond is a five-bedroom, eight-bath estate that exemplifies expansive design and contemporary style. The striking A-frame architecture, double-height windows, and soaring ceilings create dramatic, light-filled interiors where every angle frames the surrounding landscape and sunsets. A three-story entry sets the
Welcome to your 2 bedroom, 1.5 bathroom town house condo with a one car garage in the highly desirable Whispering Hills Community in Chester, NY. Well maintained and cared for by its original owner, this unit is located in a nice private section along a green space. The second floor features two spacious bedrooms and one full bathroom. The primary bedroom has cathedral ceilings and a sizable
Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of
Escape to this luxurious 7-bedroom retreat in the heart of Chester, NY! Designed for ultimate relaxation, the home boasts upscale outdoor spaces with a sparkling pool, porch lounge, and covered dining area. Inside, enjoy stylish furnishings, a chic home office, and elegant touches throughout. A game room with a pool table adds a fun element, making this the perfect mix of comfort and
Experience the charm of downtown Chester in this warm and welcoming 1 bed, 1 bath apartment. Just a short stroll to the Heritage Trail, local eateries, and cozy cafés, this location puts you right at the heart of village living. This unit includes private off-street parking and a small patio area—perfect for enjoying your morning coffee or some fresh air. This unit is situated on quiet Jackson
Well-maintained 3-bed Chester, NY....This home is meticulous and move-in ready! Rent this home and be close to everything! Just a few minutes to the highway, close to commuter bus train, and less than an hour to GWB! Popular heritage trails are 100 yards away for biking, walking, and running. Additional Information: Heating Fuel Oil Below Ground,
Newly renovated 3 bedroom unit located in the heart of Sugar Loaf and within the Warwick School District. This second-floor walkup features a bright white kitchen with stainless steel appliances, including an in-unit washer/drier, and offers a large private balcony with scenic views of Sugar Loaf Mountain. The unit is situated above a restaurant; music may be audible as late as 11 PM on Friday
Move-in ready rental in beautiful Warwick, NY. This spacious apartment-style home is nestled in a peaceful countryside setting and is available for a full-time tenant. Enjoy comfortable one-level living with scenic nature views in every direction.Upon entry, you are welcomed by a large foyer that leads into a sun-soaked living room, perfect for relaxing or entertaining. Just off the living
THE RENTAL YOU HAVE BEEN LOOKING FOR! Beautiful, well-kept fabulous home in beautiful neighborhood Monroe Woodbury School district. Completely renovated and freshly painted, All New Hardwood floors, Bathrooms, Boiler, Hot water, Ductless AC, Gorges new kitchen with appliances, spacious rooms, ample living space, and expansive backyard to enjoy all year round, Great location! Close too many major
Great 2bd 1.5ba Townhouse style unit in Whispering Hills. Living room w/ fireplace open to the dining room. Laminate floors throughout. We’ll appointed kitchen with newer cabinets and SS appliances. Vaulted Ceilings in the Master Bedroom with walk-in closet and organizer. Central air, TWO car garage, Washer/Dryer! This complex offers 2 community pools, clubhouse, tennis/basketball courts and gym.
Experience peaceful country living at 408 Bull Mill Rd, Unit 2, a Victorian-style retreat set on sprawling acreage and surrounded by nature. This 1,800 sq. ft. home offers exceptional privacy, quiet, and seclusion while providing the space and charm of a classic design. Inside, you’ll find three spacious bedrooms and two full bathrooms, thoughtfully laid out to maximize comfort and natural light.
Is there a 2-bed apartment in Chester Village with parking, outdoor space, and walkable access to downtown? This newly refreshed second floor rental offers approximately 1,000 square feet, a private covered deck, garage parking, and an updated kitchen, all set in Historic Downtown Chester near dining, shops, and the Heritage Trail. This spacious apartment at 12 Railroad Avenue, Unit Floor 2
Welcome to 98 Main St: a gracious Colonial in the center of the village of Chester!A huge "wrap-around" front porch greets you when you arrive. Once inside, you will be impressed with the "old world" charm of the stained-glass windows, dark wood trim, Hardwood floors and the pocket doors in the Living Room. Many large windows downstairs let in plenty of sunlight! Upstairs there are 4 nice
This is a beautiful rental, If you are looking to rent, here it is!! plenty of room,3 bedrooms 2.5 baths, 2 car garage, close to amenities, new bathrooms, close to shopping, close to major highways and rail for commuters. Freshly painted, new carpets, hardwood floors redone. Must see if you are looking to rent!!! Additional Information: ParkingFeatures:1 Car Attached.
Amazingly beautiful 1850's renovated home and horse property. Over 11 acres of land with approx. 3.5 acres of 4-board fenced-in pasture including 2 run-in sheds with access to water. The house is in excellent condition with high-efficiency radiant heated floors, central a/c and natural gas! There is also a stand-by generator. Enjoy beautiful wide-plank wood floors, meticulously maintained and
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