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Houses for Sale in Chester, NY

We’ll help you discover the wonderful homes for sale in Chester, NY and find the perfect fit for your needs, desires and lifestyle.

Chester, New York is a bedroom community located in southeast New York approximately 50 miles north of New York City. The Town of Chester was formed in 1845 from parts of the Towns of Blooming Grove, Goshen, Monroe and Warwick. The Village of Chester was incorporated in 1892.

Why Choose a Home in Chester, New York?

It has wonderful restaurants, parks including Goosepond Mountain State Park, and a wonderful school system. It is a great place to live and bring up a family.

The Castle Fun Center in Chester has fun for the whole family. Mini golf, go karts, batting cages, an arcade, a roller rink, rock climbing wall, and Jester’s Restaurant & Pub are just a few of the things to keep you entertained at The Castle Fun Center.

Linda Ross Realty has been helping clients find, tour, and purchase houses for sale in Chester, NY for over 20 years. Contact us for more information on homes for sale in the Chester, NY area.

Chester Real Estate Listings

Active Listings in Chester

197 Hulsetown Road Chester, NY 10918
Photo of 197 Hulsetown Road, Chester, NY 10918 (MLS # 4823931)
3 beds 2 baths 1,946 sqft $2,300
4207 Summerville Way Chester, NY 10918
Photo of 4207 Summerville Way, Chester, NY 10918 (MLS # 4822880)
3 beds 2 baths 1,274 sqft $315,000
244 Bull Mill Road Chester, NY 10918
Photo of 244 Bull Mill Road, Chester, NY 10918 (MLS # 4823684)
4 beds 2 baths 1,650 sqft $210,000
22 Walnut Street Chester, NY 10918
Photo of 22 Walnut Street, Chester, NY 10918 (MLS # 4823412)
3 beds 2 baths 1,369 sqft $249,000
26 Creamery Pond Road Chester, NY 10918
Photo of 26 Creamery Pond Road, Chester, NY 10918 (MLS # 4823354)
3 beds 3 baths 3,258 sqft $439,900
143 Conklingtown Road Chester, NY 10918
Photo of 143 Conklingtown Road, Chester, NY 10918 (MLS # 4803356)
4 beds 4 baths 2,852 sqft $559,000
4606 Whispering Hills Chester, NY 10918
Photo of 4606 Whispering Hills, Chester, NY 10918 (MLS # 4822948)
2 beds 2 baths 1,086 sqft $184,900
133 Creamery Pond Road Chester, NY 10918
Photo of 133 Creamery Pond Road, Chester, NY 10918 (MLS # 4821329)
4 beds 3 baths 3,442 sqft $535,000
441 Black Meadow Road Chester, NY 10918
Photo of 441 Black Meadow Road, Chester, NY 10918 (MLS # 4822807)
4 beds 4 baths 5,865 sqft $1,500,000
2718 Whispering Chester, NY 10918
Photo of 2718 Whispering, Chester, NY 10918 (MLS # 4822743)
2 beds 2 baths 1,086 sqft $1,690
3 Stacey Lane Chester, NY 10918
Photo of 3 Stacey Lane, Chester, NY 10918 (MLS # 4817196)
3 beds 3 baths 2,904 sqft $475,000
2608 Whispering Hills Chester, NY 10918
Photo of 2608 Whispering Hills, Chester, NY 10918 (MLS # 4822316)
2 beds 2 baths 1,072 sqft $155,000
9 Fields Lane Chester, NY 10918
Photo of 9 Fields Lane, Chester, NY 10918 (MLS # 4822010)
2 beds 2 baths 2,216 sqft $378,500
3124 Whispering Hills, Unit 3124 Chester, NY 10918
Photo of 3124 Whispering Hills, Unit 3124, Chester, NY 10918 (MLS # 4821790)
2 beds 1 bath 1,084 sqft $179,000
Odyssey Drive Chester, NY 10918
Photo of Odyssey Drive, Chester, NY 10918 (MLS # 4822130)
0 beds 0 baths $145,000

Sold Listings in Chester

145 Hulsetown Road Chester, NY 10918
Photo of 145 Hulsetown Road, Chester, NY 10918 (MLS # 4737126)
4 beds 4 baths 5,470 sqft $565,000
2004 Whispering Hills, Unit 23 Chester, NY 10918
Photo of 2004 Whispering Hills, Unit 23, Chester, NY 10918 (MLS # 4812088)
3 beds 3 baths 1,331 sqft $200,000
10 Oak Street Chester, NY 10918
Photo of 10 Oak Street, Chester, NY 10918 (MLS # 4753559)
4 beds 2 baths 1,666 sqft $157,500
19 Chester Acres Boulevard Chester, NY 10918
Photo of 19 Chester Acres Boulevard, Chester, NY 10918 (MLS # 4811499)
3 beds 3 baths 1,876 sqft $300,000
2117 Whispering Hills Chester, NY 10918
Photo of 2117 Whispering Hills, Chester, NY 10918 (MLS # 4808889)
2 beds 2 baths 1,053 sqft $142,000
440 Black Meadow Road Chester, NY 10918
Photo of 440 Black Meadow Road, Chester, NY 10918 (MLS # 4751362)
3 beds 3 baths 3,250 sqft $250,000
158 Hambletonian Avenue Chester, NY 10918
Photo of 158 Hambletonian Avenue, Chester, NY 10918 (MLS # 4807816)
4 beds 2 baths 1,800 sqft $305,000
4011 Whispering Hills Chester, NY 10918
Photo of 4011 Whispering Hills, Chester, NY 10918 (MLS # 4807750)
3 beds 2 baths 1,316 sqft $185,000
187 Pine Hill Road Chester, NY 10918
Photo of 187 Pine Hill Road, Chester, NY 10918 (MLS # 4807159)
4 beds 3 baths 3,274 sqft $462,000
61 Pewter Circle Chester, NY 10918
Photo of 61 Pewter Circle, Chester, NY 10918 (MLS # 4806275)
3 beds 3 baths 2,210 sqft $300,000
61 Nancy Chester, NY 10918
Photo of 61 Nancy, Chester, NY 10918 (MLS # 4637776)
4 beds 3 baths 2,700 sqft $180,000
1819 Whispering Hills Chester, NY 10918
Photo of 1819 Whispering Hills, Chester, NY 10918 (MLS # 4805583)
2 beds 2 baths 1,086 sqft $121,000
1366 Kings Highway Chester, NY 10918
Photo of 1366 Kings Highway, Chester, NY 10918 (MLS # 4705082)
2 beds 3 baths 1,736 sqft $300,000
1104 Whispering Hills Chester, NY 10918
Photo of 1104 Whispering Hills, Chester, NY 10918 (MLS # 4804053)
3 beds 3 baths 1,331 sqft $220,000
20 Trotting Drive Chester, NY 10918
Photo of 20 Trotting Drive, Chester, NY 10918 (MLS # 4803096)
3 beds 1 bath 1,574 sqft $228,000

Chester School Data

Chester School Districts

Chester Union Free School District
K-12

Chester Schools

Chester Elementary School
K-5, public
Chester Academy Middle High School
6-12, public
Ohel Torah
10, private
Bellvale School
K-8, private