$537,327Average Value$272Average Price per Sq Ft44Homes 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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/2
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
Kathy White,
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.
View GreatSchools Rating Methodology
On average, homes in Chester, NY sell after 55 days on the market compared to the national average of 57 days. The median sale price for homes in Chester, NY over the last 12 months is $500,750, down 5% from the median home sale price over the previous 12 months.
Welcome to 82 Southside Dr in Monroe — a beautifully renovated ranch-style home offering effortless one-level living in the highly sought-after Monroe-Woodbury School District. This 4-bedroom, 2-bath home features a versatile layout with an additional home office or den, ideal for remote work, a playroom, or guest space. Fully renovated from top to bottom, the home showcases brand-new flooring
Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates Community, this expansive Colonial-style estate delivers classic elegance with modern comfort. Built in 1993 and thoughtfully designed for multi-generational living and refined entertaining, this home offers generous spaces, lush
Set gracefully on 3.8 private acres within the highly coveted Warwick School District, this exceptional custom home offers a rare blend of architectural elegance and refined living. Surrounded by a collection of equally distinguished residences, the property provides an expansive, park-like sanctuary while remaining nestled in the heart of one of the region’s most sought-after communities.
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
Welcome to 3910 Whispering Hills — a refined, turnkey townhome in one of Chester’s most desirable residential enclaves. This thoughtfully appointed 3-bed, 2.5-bath home blends classic suburban elegance with low-maintenance living. Set within a mature, amenity-rich community, you’ll enjoy direct access to commuter transit, shops, and parks while savoring the quiet privacy prized by Hudson Valley
Welcome to this spacious and versatile home nestled at a dead end st. in the desirable town of Chester. Offering an abundance of living space, this property is ideal for those seeking privacy, comfort, flexibility, and room to grow. The home features a functional layout with generously sized bedrooms, a bright and inviting living area, and a well-appointed kitchen designed for everyday living and
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 your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional
Rare Opportunity in Whispering Hills! Discover this uniquely reimagined end-unit condo, expertly converted from a three-bedroom layout into a sprawling, sun-drenched two-bedroom retreat. This home is a masterclass in modern comfort, featuring eight brand-new Andersen windows and a matching Andersen door (2025) that perfectly frames spectacular, far-reaching horizon views. Much of the interior has
Welcome to 82 Southside Dr in Monroe — a beautifully renovated ranch-style home offering effortless one-level living in the highly sought-after Monroe-Woodbury School District. This 4-bedroom, 2-bath home features a versatile layout with an additional home office or den, ideal for remote work, a playroom, or guest space. Fully renovated from top to bottom, the home showcases brand-new flooring
Exceptional value in Monroe Woodbury! Well 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
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.
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.
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
Beautiful and spacious 4 Bedroom, 2.5 Bath Colonial set on park-like property in a lovely neighborhood with a serene backdrop of mature trees, offering both privacy and a peaceful setting. This home features a large eat-in kitchen with abundant cabinetry, tremendous counter space, and a sliding glass door leading to a newer rear deck—perfect for relaxing or entertaining outdoors.The oversized
Property Id: 2505575Welcome to this well-kept 1 bedroom + extra bonus room apartment located at — perfect for anyone needing a little extra space for a home office, guest room, or creative setup.•1 large bedroom + versatile bonus room•Private front & back entrances•Covered patio + backyard access•Small private yard space•Metal shed for extra storage•Off-street
Super Clean & Bright Rental in Whispering Hills. 2 Bedrooms, 1.5 Baths, 1 Car Garage with Central Air, Young Kitchen and Appliances, Laminate Flooring on 1st Floor with Laundry and updated Half Bath. Freshly Painted in 2022. Upstairs you will find Primary Bedroom with Vaulted Ceilings, Walk in Closet w/Organizers, Updated Full Bath, Skylight and Spacious Guest Room. Upstairs offers Carpeting.
Property Id: 1802590Stunning Home with Expansive Yard and Abundant Storage!Welcome to this incredible property, boasting a massive backyard perfect for outdoor entertaining! Enjoy warm weather gatherings on the spacious deck, and make the most of the two sheds for storing tools, equipment, and more.This fantastic home also features:- 1 garage for secure vehicle
Welcome to 4 Ayr Court in Chester, NY — a spacious and beautifully maintained 6-bedroom, 4-bathroom home available for rent! Nestled on a quiet street, this impressive property offers the perfect blend of space, comfort, and convenience. Step inside to find a bright and inviting interior featuring generous living areas, ideal for both everyday living and entertaining. The expansive layout
A charming country cottage is available for rent and is situated on a picturesque country road. The main level features an eat-in kitchen, dining room, and two bedrooms, while the upper level has three bedrooms. The cottage boasts updated flooring, windows, kitchen, and heating. The interior has been freshly painted, and new appliances and flooring have been added in 2021. The older "Hamptons"
Please check this well maintained, clean and great size townhouse! It is nestled in the heart of Orange County with Warwick school district. This beautiful home is offering 3 bedrooms, 2 1/2 bathrooms, one car garage and a partial finished basement great for your additional room or for storage. It is an easy commute to major highways, shopping and restaurants. You will enjoy the spacious living
Welcome to Refined Living — A Contemporary Ranch renovated for Elevated Year-Round Living with ease, entertainment and privacy! Perfectly set on 1.2 acres with Mountain views just one hour from New York City, this FULLY FURNISHED and fully equipped 3,412 square-foot home provides the convenience of one level living blended with the luxury of upscale design features. The bright and open Foyer
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
***Rare opportunity***Available April 1st for occupancy! 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,
Very bright and spacious top-floor Penthouse apartment! Come see this open layout floorplan. The updated kitchen has a new stainless steel refrigerator and dishwasher. The Primary bedroom has large double closets and can accommodate a king-size bed. The living room/dining room combination is bright and sun-filled, with plenty of windows and an outside deck. You’ll appreciate the convenience of
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
Great spacious end unit townhouse in Kings Estates ! Freshly painted with professionally cleaned carpets makes this townhouse move in ready! This unit has been renovated within the last few years and includes newer stainless steel appliances and hardwood floors throughout the living and dining room. Back deck off of the dining room and kitchen area offers a GREAT view. Must see to appreciate !
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
