The well-established small town of Chester, New York is a great place to live in Orange County. Chester has a rich heritage and long history and is home to the historic village of the same name, around which most real estate in Chester is located. Along the Village of Chester’s Main Street, there are many lovely restored buildings, and the community is also home to a museum that was originally a train station. Historically, Chester has been a hub for the dairy industry, and it is the proud birthplace of Philadelphia-style cream cheese.
In addition to its history and heritage, Chester is a naturally beautiful place with quick and easy access to a long list of exciting recreation opportunities. For example, not far from Chester real estate, you’ll find Goosepond Mountain State Park, which offers ball fields and tennis courts, as well as trails for cycling, hiking, and horseback riding. Speaking of trails, the Orange County Heritage Trail passes through the community following the old Erie Railway line. Recreation isn’t the only activity easily accessed, but Chester homes are also near great options for entertainment, shopping, and dining, too. In fact, the community is home to a six-screen movie theatre, a ShopRite, and several other small retailers.
This family-friendly community also has a respected school district, the Chester Union Free School District. All three schools run by the district are conveniently located in Chester and bear the community’s name. And all of these desirable features contribute to the appeal of real estate in Chester. Homes for sale in Chester are primarily mid-range single-family homes, though there are outliers. For example, there are older homes, as well as new construction in Chester, and homes with lots larger than a quarter acre, as well as acreage. You’ll also find a handful of lower-maintenance attached properties in Chester, such as townhomes and condos. Regardless of the kind of Chester properties that most interest you, we would be delighted to assist you, so please connect with us at your earliest convenience and we will happily answer all of your questions regarding available real estate in Chester, New York.
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Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgett...
Perched beautifully atop a scenic hill, this lovingly maintained home has been cherished by its original owners and offers a rare combination of privacy, space, and timel...
9.6 ACRES OF OPEN LAND & DEVELOPMENT POTENTIAL IN BLOOMING GROVE! This expansive property offers a rare opportunity to own nearly 10 acres in a beautiful Orange County se...
Discover a compelling combination of space, convenience and Chester accessibility at 3706 Whispering Hills. This 2-bedroom, 2-bath, approximately 1,086-sq-ft townhome-sty...
Welcome to 2107 Whispering Hills, a comfortable 2-bedroom, 1-bath condo offering 1,086 square feet of living space in a convenient Chester location. This home offers an e...
Welcome to 94 Booth Road! Set on a beautiful, level 1.8-acre lot, this home offers a peaceful setting with plenty of space to enjoy both indoors and out. Head upstairs t...
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 cathe...
PRICED TO SELL! Bright and spacious 3-bedroom, 2-bath end-unit townhouse in Whispering Hills, offered at an attractive price compared with other condos in the community. ...
Discover the charm of 18 Schueler Road, an inviting 2-bedroom, 1-bath home in the Monroe-Woodbury School District. Tucked along a private road with a road maintenance agr...
*MOTIVATED SELLER* PRIVATE WOODED COLONIAL!! 4 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen with Granite Counter Tops, Stainless Steel Appliances & Pantry! Mas...
Welcome to Chester, NY!! Come see this spacious home featuring 2 bedrooms and 2 full baths, with a bonus room. This home has plenty of possibilities and includes a finish...
Welcome to 101 Beverly Road, a beautifully renovated 4-bedroom, 2 full and 2 half bath home offering approximately 3,764 square feet of total finished living space on 1.9...
Welcome to this charming 4-bedroom, 2-bath bilevel, ideally situated on a quiet dead-end street. The inviting open floor plan offers a seamless flow for everyday living a...
Custom-built by renowned builder Lou Tedaldi, this one-owner Center Hall Colonial offers nearly 3,000 sq. ft. of exceptionally crafted living space nestled on 6.2 pristin...
Welcome home to your beautiful, quiet and peaceful oasis. This 3 bed/3bath unit with a spacious 2-car garage has many new recent updates including new flooring, updated k...
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