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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

70 Main Street, Chester image
70 Main Street, Chester $469,000

Welcome to 70 Main Street, a village gem situated right in the heart of historic Chester! This versatile 4-bedroom, 2.5-bathroom home combines classic architectural chara...

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  • 3 Beds
  • 3 Baths
  • 1034449 MLS
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176 Beverly Road, Chester image
176 Beverly Road, Chester $777,000

Motivated Seller. Highly sought-after Warwick Schools, this Colonial offers curb appeal with custom stone entrance pillars featuring illuminated house numbers, an inlaid ...

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  • 4 Beds
  • 3 Baths
  • 1034535 MLS
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3 Grand View Terrace, Chester image
3 Grand View Terrace, Chester $749,000

Discover refined living at 3 Grand View Terrace, a beautiful 6-bedroom, 3-bath Colonial in Chester's sought-after Valley View Phase II subdivision. This impressive home b...

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  • 6 Beds
  • 3 Baths
  • 1034157 MLS
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2522 Whispering Hills, Chester image
2522 Whispering Hills, Chester $369,000

Welcome to Whispering Hills! Discover easy living, comfort and privacy while living within a neighborhood community. Perfect for first time home buyers or if you're dow...

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  • 3 Beds
  • 3 Baths
  • 1027103 MLS
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66 Whitetail Run, Chester image
66 Whitetail Run, Chester $449,000

Welcome to 66 Whitetail Run – Chester, NY. Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy...

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  • 3 Beds
  • 2 Baths
  • 1033721 MLS
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33 Meadow Avenue, Chester image
33 Meadow Avenue, Chester $370,000

One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ra...

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  • 3 Beds
  • 1 Baths
  • 1033159 MLS
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3 Hilltop Lane, Chester image
3 Hilltop Lane, Chester $750,000

Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 brigh...

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  • 5 Beds
  • 3 Baths
  • 1031147 MLS
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2007 Whispering Hills, Chester image
2007 Whispering Hills, Chester $279,999

Welcome to 2007 Whispering Hills Drive! This 2-bedroom, 1.5-bath condo offers comfortable living in one of Chester’s most desirable communities. The main level features ...

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  • 2 Beds
  • 2 Baths
  • 1030827 MLS
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151 Main Street, Chester image
151 Main Street, Chester $350,000

A Diamond in the Rough! Calling all handymen to bring this Village Charmer back to its' original glory. This home has a large Living Room with a cozy alcove, spacious...

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  • 4 Beds
  • 1 Baths
  • 1031155 MLS
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1 Hilltop Lane, Chester image
1 Hilltop Lane, Chester $750,000

Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 brigh...

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  • 5 Beds
  • 3 Baths
  • 1031045 MLS
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4008 Whispering Hills Drive, Chester image
4008 Whispering Hills Drive, Chester $315,000

Move in ready townhome with a NYC bus stop within the community!! Whispering Hills in Chester is perfectly positioned for commuters being 2 miles to Route 17. Enjoy a ...

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  • 2 Beds
  • 2 Baths
  • 1027838 MLS
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7 Lakeview Drive, Chester image
7 Lakeview Drive, Chester $549,999

This charming updated 4-bedroom beauty in the Warwick School district offers a private and quiet setting featuring an above ground pool surrounded by a freshly painted de...

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  • 4 Beds
  • 3 Baths
  • 1028872 MLS
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50 Hambletonian Avenue, Chester image
50 Hambletonian Avenue, Chester $599,900 ▼

Located in the heart of the Village of Chester, this beautifully updated home offers the rare combination of modern comfort, privacy, and convenience. Just steps from Che...

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  • 3 Beds
  • 2 Baths
  • 1029645 MLS
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197 Oxford Road, Chester image
197 Oxford Road, Chester $799,000

Welcome to this beautifully charming Center Hall Colonial, privately set back from the road on a picturesque property with a tranquil man-made pond, fountain, and invitin...

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  • 4 Beds
  • 3 Baths
  • 1012284 MLS
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29 Murray Drive, Chester image
29 Murray Drive, Chester $650,000

Welcome to a contemporary retreat where refined design, exceptional craftsmanship, and a seamless connection to nature come together in one of Chester’s most desirable se...

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  • 3 Beds
  • 4 Baths
  • 1027353 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: debwarner@kw.com

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