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Chester Real Estate Search

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Chester Homes for Sale

In the County of Orange, the small town of Chester, New York, is a well-established community with a long history and rich heritage. This delightful town encompasses the village of Chester, a historic settlement around which most of Chester’s real estate is found. The village of Chester encompasses an old train station that is now home to a museum, and along Main Street, you’ll find many beautifully restored heritage structures. The town is the proud birthplace of Philadelphia-style cream cheese and historically has been one of the dairy industry’s centers. 

Further contributing to the appeal of Chester homes, in proximity, you’ll find several state parks and smaller local parks. Many of these recreation destinations offer tennis courts and ball fields, like those found at Goosepond Mountain State Park. The area is also rich with trails for horseback riding and hiking. Following the old Erie Railway line, the Orange County Heritage Trail is an excellent example and passes right through Chester. Beyond recreation, shopping and dining opportunities are also easily accessible. Specifically, there is a ShopRite, several other retailers, and a six-screen movie theatre in the Chester Mall.

Furthermore, this family-friendly community is served by the Chester Union Free School District which oversees the operation of Chester High School, Chester Middle School, and Chester Elementary School, all located within the community. Homes for sale in Chester are diverse, but many fall within the mid-range and are standard single-family properties. That said, there is new construction in Chester, as well as older homes, too. It is not uncommon to find acreage in Chester either, and lots larger than one-quarter acre are also common. For buyers seeking a lower maintenance option, there are a handful of Chester condos from which to choose as well. Please, as soon as it is convenient for you, connect with us and we will happily answer all of your questions about the currently available properties 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 and Condos for Sale

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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3211 Whispering Hills, Chester image
3211 Whispering Hills, Chester $370,000

Move right in! This beautifully maintained and thoughtfully updated 3-bedroom, 2-full-bath END-UNIT condo offers almost 1,400 square feet of comfortable, easy one-level l...

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  • 3 Beds
  • 2 Baths
  • 1046996 MLS
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19 Meadow, Chester image
19 Meadow, Chester $495,000

Welcome to 19 Meadow Avenue in Chester! This spacious 3-bedroom home offers approximately 1,910 square feet of living space with an open-concept layout connecting the liv...

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  • 3 Beds
  • 2 Baths
  • 1046778 MLS
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4704 Whispering Hills, Chester image
4704 Whispering Hills, Chester $380,000

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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260 Gibson Hill Road, Chester image
260 Gibson Hill Road, Chester $374,900

UNLOCK UNLIMITED POTENTIAL IN WARWICK VALLEY SCHOOLS! Are you ready to stop renting, build instant equity, and design your dream home from the ground up? This hidden gem ...

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  • 3 Beds
  • 2 Baths
  • 1044316 MLS
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69 Cedar Pond Lane, Chester image
69 Cedar Pond Lane, Chester $1,685,000

Welcome to 69 Cedar Pond Lane. Perched to capture panoramic mountain views, this expansive Chester estate offers an extraordinary combination of multi generational living...

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  • 6 Beds
  • 8 Baths
  • 1043860 MLS
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2921 Whispering Hills, Chester image
2921 Whispering Hills, Chester $374,900

WHISPERING HILLS! PRIME LOCATION! Largest Unit! Two Story Living! End Unit! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Dining/ Living Room with Fireplace!...

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  • 3 Beds
  • 3 Baths
  • 1043986 MLS
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1005 Whispering Hills, Chester image
1005 Whispering Hills, Chester $290,000

Welcome to Whispering Hills! This spacious two-level, 2-bedroom, 1.5-bath condo with a 1-car garage features a great combination of updates and an ideal commuter location...

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  • 2 Beds
  • 2 Baths
  • 1043197 MLS
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121 Conklingtown Road, Chester image
121 Conklingtown Road, Chester $749,000

Imagine coming home to a beautifully maintained and upgraded property designed for comfort, entertaining, and enjoying the outdoors. This home features a high-ceiling foy...

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  • 4 Beds
  • 3 Baths
  • 1042913 MLS
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50 Hambletonian Avenue, Chester image
50 Hambletonian Avenue, Chester $550,000

Welcome to this charming ranch style home set on 4 picturesque acres, featuring beautiful flowing hardwood floors and a peaceful, private setting. The inviting kitchen of...

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  • 3 Beds
  • 2 Baths
  • 1042882 MLS
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2124 Whispering Hills, Chester image
2124 Whispering Hills, Chester $299,000

Welcome to Whispering Hills! This inviting end-unit home offers a comfortable blend of everyday living, privacy, and convenience. Enjoy easy access to major commuter rout...

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  • 2 Beds
  • 1 Baths
  • 1042658 MLS
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3561 Rte 94, Chester image
3561 Rte 94, Chester $649,999

If open concept and bountiful space is what you are looking for, STOP right here—you have found it! Spectacular contemporary-designed ranch with nearly 3,000 sq ft of fin...

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  • 3 Beds
  • 3 Baths
  • 1041906 MLS
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65 Oxford Springs Road, Chester image
65 Oxford Springs Road, Chester $699,000

Welcome to 65 Oxford Springs Road! This stunning 5-bedroom, 3.5-bath Colonial offering approximately 3,400 square feet of thoughtfully designed living space in a peaceful...

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  • 5 Beds
  • 4 Baths
  • 1041722 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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