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Chester Real Estate Search

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Chester Homes for Sale

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.

Our website features the best Chester real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in the Chester real estate market? Sign up for a Chester Real Estate Market Report to see what’s active, under contract, and sold!

Contact us today to find out how we can be of assistance to you!

Newest Chester Homes for Sale

985 Craigville Road, Chester image
985 Craigville Road, Chester $750,000

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...

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  • 4 Beds
  • 4 Baths
  • 1057348 MLS
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111 Ayr Road, Chester image
111 Ayr Road, Chester $599,000

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...

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  • 4 Beds
  • 5 Baths
  • 1049653 MLS
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7 Greycourt Road, Chester image
7 Greycourt Road, Chester $1,850,000

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...

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  • 3 Beds
  • 3 Baths
  • 1054698 MLS
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3706 Whispering Hills, Chester image
3706 Whispering Hills, Chester $339,900

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...

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  • 2 Beds
  • 2 Baths
  • 1039289 MLS
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2107 Whispering Hills, Chester image
2107 Whispering Hills, Chester $309,000 ▼

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...

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  • 2 Beds
  • 2 Baths
  • 1050213 MLS
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94 Booth Road, Chester image
94 Booth Road, Chester $525,000

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...

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  • 3 Beds
  • 3 Baths
  • 1050173 MLS
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1212 Whispering Hills, Chester image
1212 Whispering Hills, Chester $269,000

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...

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  • 2 Beds
  • 1 Baths
  • 1048656 MLS
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1223 Whispering Hills, Chester image
1223 Whispering Hills, Chester $299,900

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. ...

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  • 3 Beds
  • 2 Baths
  • 1051585 MLS
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18 Schueler Road, Chester image
18 Schueler Road, Chester $339,900

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...

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  • 2 Beds
  • 1 Baths
  • 1046033 MLS
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1168 Craigville Road, Chester image
1168 Craigville Road, Chester $779,900

*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...

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  • 4 Beds
  • 3 Baths
  • 1050193 MLS
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19 Meadow Avenue, Chester image
19 Meadow Avenue, Chester $525,000

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...

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  • 2 Beds
  • 2 Baths
  • 1050131 MLS
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101 Beverly Road, Chester image
101 Beverly Road, Chester $879,000

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...

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  • 4 Beds
  • 4 Baths
  • 1048079 MLS
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8 Townsend Place, Chester image
8 Townsend Place, Chester $459,000

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...

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  • 4 Beds
  • 2 Baths
  • 1047996 MLS
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5 Red Fox Run, Chester image
5 Red Fox Run, Chester $679,000

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...

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  • 4 Beds
  • 4 Baths
  • 1046418 MLS
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4704 Whispering Hills, Chester image
4704 Whispering Hills, Chester $370,000 ▼

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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  • 3 Beds
  • 3 Baths
  • 1038636 MLS
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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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Keller Williams Valley Realty
123 Tice Blvd. Woodcliff Lake, NJ 07677


Office: (917) 612-5682
Email: Deborah@Warner.me

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