About Chester

Homes For Sale In Chester, NY

Chester is a community in Orange County, New York. Most of the homes for sale in Chester are clustered around the town's main settlement, the historic village of Chester. The village is home to a number of lovingly restored heritage properties along Main Street and there is a museum in the old train station. The area has historically been a center of the dairy industry and Chester is proud to be known as the birthplace of Philadelphia-style cream cheese (and I bet you thought it came from Philadelphia!).

Read More About Chester

Chester, NY Real Estate Listings

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000

Chester, NY Real Estate Listings

99 Properties Found. Page 1 of 17.
Photo of Listing #H6115155

7 Black Meadow Road, Chester


MLS® # H6115155

Keller Williams Realty Status: ActiveHGMLS
Photo of Listing #H6205599

1253 Kings Highway, Chester

$2,000,000 - 102 Acres

MLS® # H6205599

Key Properties of Hudson Vly Status: ActiveHGMLS
Photo of Listing #H6230037

151 Kings Highway Bypass, Chester

$1,900,000 - 4 Beds, 5 Baths, 5,539 Sf

MLS® # H6230037

Keller Williams Realty Status: ActiveHGMLS
Photo of Listing #H6235859

8 Kings Highway, Chester


MLS® # H6235859

BHHS Hudson Valley Properties Status: ActiveHGMLS
Photo of Listing #H6204289

42 Brookside Avenue, Chester


MLS® # H6204289

Keller Williams Realty Status: ActiveHGMLS
Photo of Listing #H6232065

10 Silvertail Road, Chester

$1,299,000 - 4 Beds, 5 Baths, 5,007 Sf

MLS® # H6232065

Exp Realty Status: PendingHGMLS

Chester Real Estate

At the top end of the Chester real estate market, you find a mix of properties. As well as land and farms, you'll find some single-family homes on acreage. However, the majority of homes in Chester are in the mid-range price bracket and even in that price range, you can expect to find a home with a big yard. With older homes, lots of several acres are common and even with newer and new construction homes, lot sizes over a quarter acre are common. At the lower end of the Chester market, you'll find small parcels of development land and as well as condos and older single-family homes.

Amenities Close To Chester Real Estate

Chester real estate enjoys close proximity to numerous local and state parks. There are several community parks with ball field and tennis courts and just down the road is Goosepond Mountain State Park, which is a great location for hiking and horseback riding. The Orange County Heritage Trail, which follows the old Erie Railway line, also passes through Chester. There is local shopping at Chester Mall in the village, where you'll find a ShopRite and numerous other stores, as well as a 6-screen movie theatre. Most homes in the community are served by the Chester Union Free School District, which operates Chester Elementary and Chester Middle and High School in the community.

Monroe Realty will be happy to help you buying or selling your Chester home, so please don't hesitate to contact us today! Call Us: 845-781-8100

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