$548,352Average Value$271Average Price per Sq Ft69Homes 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 66 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, NY over the last 12 months is $515,000, down 2% from the median home sale price over the previous 12 months.
From the covered front porch to the spacious backyard, this four-bedroom, two-and-a-half-bath home offers plenty of room to live, gather and enjoy. Inside, hardwood floors flow through the bright living and dining rooms, while the kitchen features ample cabinetry, generous counter space and a center island. The vaulted family room with fireplace is the heart of the home, creating a warm and
Built for easy, manageable living. Set on a corner lot, this 3-bed, 1-bath ranch has a welcoming presence from the moment you approach, complemented by an oversized driveway and front deck. Inside, the main living spaces feel open and connected while maintaining a sense of distinction, offering a comfortable layout with functionality in mind. A nicely-sized entrance foyer invites you in before
Welcome to stress-free Hudson Valley living in the desirable Whispering Hills community! This end unit, bright and airy 2-bedroom, 1-bathroom condo features soaring cathedral ceilings, a cozy fireplace, and an updated kitchen complete with sleek stainless steel appliances. Enjoy fantastic turn-key amenities right outside your door, including two community pools, a clubhouse, gym, tennis,
Welcome to this well-maintained raised ranch in Chester, NY, offering 4 bedrooms and 1.5 bathrooms with plenty of space and flexibility. The home features hardwood floors, a bright and inviting layout, and comfortable living spaces throughout. Step outside onto the large deck overlooking a spacious backyard, perfect for outdoor entertaining, recreation, or simply enjoying the outdoors.
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
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
Gracious Colonial home features the best of the traditional style with the appeal of a contemporary open floor plan in the kitchen - family room area. Meticulously maintenance and stylish updates create easy living spaces that are great for daily relaxation as well as entertainment. The full-length deck, large seating area around the fire pit and expansive yard provide outdoor areas to relax,
20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange
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
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
From the covered front porch to the spacious backyard, this four-bedroom, two-and-a-half-bath home offers plenty of room to live, gather and enjoy. Inside, hardwood floors flow through the bright living and dining rooms, while the kitchen features ample cabinetry, generous counter space and a center island. The vaulted family room with fireplace is the heart of the home, creating a warm and
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,
Welcome to this charming ranch style home set on 4 picturesque acres, featuring beautiful flowing hardwood floors and a peaceful, private setting. The inviting kitchen offers gorgeous marble countertops, an abundance of cabinetry, a sink positioned beneath the windows, and stainless-steel appliances. From the living room, double sliding doors open onto the expansive wraparound porch, creating an
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
Property Id: 2842725 Piso/nivel superior en alquiler: 3 habitaciones 1 baño completo 1 cocina completa acceso al deck acceso a lavandería estacionamiento para 2 vehículos Precio: $3,000.00 con bills incluido Price: 3,000.00 with bills included top floor/level for rent: 3 bedrooms 1 full bathroom 1 full kitchen
Fresh carpet has just been laid throughout this luminous top-floor penthouse, where an open layout and abundant sunshine create an inviting canvas for daily life. At 900 square feet, this 2-bedroom, 1-bath home balances spaciousness with a cozy, lived-in warmth. Cooks will appreciate the updated kitchen, outfitted with a new stainless steel refrigerator and dishwasher that bring both style and
Property Id: 2791335 Welcome to your new home at 53 Main St in Chester, NY! This single unit offers modern amenities including oven, microwave, washer, dryer, and more. Enjoy the convenience. building. No pets allowed. Rent for $2100/month starting 09/01/2026. Don't miss out on this fantastic opportunity! No Smoking ,credit and reference checked .proof of income. Heat and
The advertised rate of $16,238/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 be
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
Charming. Updated. Affordable.Welcome to this beautifully updated 2-bedroom, 1-full bath trailer, offering comfortable living with modern finishes throughout. Step inside to a bright, open living area designed for both relaxing and entertaining.The stunning white kitchen features elegant quartz countertops with quartz backsplash, beautiful cabinetry, and plenty of workspace, creating
Waterfront living at its finest! HEAT and HOT WATER Included. Welcome to this beautifully maintained center-unit townhome in one of Monroe's most sought-after communities. Offering over 1,800 square feet of living space, this home features 3 bedrooms, 2 full bathrooms, 1 half bath, and breathtaking lake views right from your backyard. The updated eat-in kitchen is the heart of the home,
Welcome to your spacious new home at 7 Ruscitti Drive in charming Chester, NY! This bright and airy single-family home features 4 generous bedrooms, a full bath, and a large basement with plenty of extra storage space, giving everyone room to relax, work, or stay organized. Best of all, pets are warmly welcomed! Located in a quiet, friendly neighborhood in the heart of the Hudson Valley, you’ll
THE VIEWS, THE LIFESTYLE, THE SPACE all in one beautiful townhouse located in an award winning school district. Just five minutes to the Village of Warwick and easy access to major highway, this surprising end-unit townhome offers exceptional outdoor space with expansive decking and private large back and side yard with jaw dropping mountain views. A sunny open floor plan with a contemporary
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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