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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

505 Bull Mill Road Chester, NY 10918
Photo of 505 Bull Mill Road, Chester, NY 10918 (MLS # 4983741)
4 beds 3 baths 2,905 sqft $489,999
64 Brookside Avenue Chester, NY 10918
Photo of 64 Brookside Avenue, Chester, NY 10918 (MLS # 4990677)
0 beds 0 baths 2,184 sqft $375,000
1302 Whispering Hills Chester, NY 10918
Photo of 1302 Whispering Hills, Chester, NY 10918 (MLS # 4989274)
3 beds 2 baths 1,316 sqft $1,950
10 Gumwood Drive Chester, NY 10924
Photo of 10 Gumwood Drive, Chester, NY 10924 (MLS # 4910820)
0 beds 0 baths $7,500
8 Gumwood Drive Chester, NY 10924
Photo of 8 Gumwood Drive, Chester, NY 10924 (MLS # 4910815)
0 beds 0 baths $65,000
6 Gumwood Drive Chester, NY 10924
Photo of 6 Gumwood Drive, Chester, NY 10924 (MLS # 4734736)
0 beds 0 baths $65,000
131 Laroe Road Chester, NY 10918
Photo of 131 Laroe Road, Chester, NY 10918 (MLS # 4987223)
4 beds 4 baths 2,496 sqft $389,000
3824 Whispering Hills Chester, NY 10918
Photo of 3824 Whispering Hills, Chester, NY 10918 (MLS # 4985299)
2 beds 1 bath 1,084 sqft $1,650
124 Dug Road Chester, NY 10918
Photo of 124 Dug Road, Chester, NY 10918 (MLS # 4986113)
4 beds 3 baths 2,572 sqft $339,900
3819 Whispering Hills Chester, NY 10918
Photo of 3819 Whispering Hills, Chester, NY 10918 (MLS # 4985603)
2 beds 2 baths 1,081 sqft $195,000
Bellvale Road Chester, NY 10918
Photo of Bellvale Road, Chester, NY 10918 (MLS # 4838030)
0 beds 0 baths $110,000
487 Black Meadow Road Chester, NY 10918
Photo of 487 Black Meadow Road, Chester, NY 10918 (MLS # 4900708)
5 beds 4 baths 4,204 sqft $344,000
1005 Whispering Hills Chester, NY 10918
Photo of 1005 Whispering Hills, Chester, NY 10918 (MLS # 4983458)
2 beds 2 baths 1,053 sqft $1,800
60 Pewter Circle Chester, NY 10918
Photo of 60 Pewter Circle, Chester, NY 10918 (MLS # 4983806)
3 beds 3 baths 2,210 sqft $319,000
2503 Whispering Hills Chester, NY 10918
Photo of 2503 Whispering Hills, Chester, NY 10918 (MLS # 4982202)
3 beds 3 baths 1,331 sqft $235,000

Sold Listings in Chester

21 Meadow Avenue Chester, NY 10918
Photo of 21 Meadow Avenue, Chester, NY 10918 (MLS # 4918202)
4 beds 4 baths 2,444 sqft $237,000
6 Townsend Place Chester, NY 10918
Photo of 6 Townsend Place, Chester, NY 10918 (MLS # 4850837)
2 beds 2 baths 1,216 sqft $134,900
2611 Whispering Hills Chester, NY 10918
Photo of 2611 Whispering Hills, Chester, NY 10918 (MLS # 4936592)
3 beds 2 baths 1,316 sqft $198,900
1052 Craigville Road Chester, NY 10918
Photo of 1052 Craigville Road, Chester, NY 10918 (MLS # 4935363)
3 beds 4 baths 3,240 sqft $635,000
24 Lakeview Drive Chester, NY 10918
Photo of 24 Lakeview Drive, Chester, NY 10918 (MLS # 4930699)
3 beds 3 baths 1,848 sqft $329,000
3824 Whispering Hills Drive Chester, NY 10918
Photo of 3824 Whispering Hills Drive, Chester, NY 10918 (MLS # 4928779)
2 beds 1 bath 1,084 sqft $160,000
66 Dug Road Chester, NY 10918
Photo of 66 Dug Road, Chester, NY 10918 (MLS # 4927569)
3 beds 2 baths 1,992 sqft $189,900
4309 whispering hls Chester, NY 10918
Photo of 4309 whispering hls, Chester, NY 10918 (MLS # 4926207)
3 beds 3 baths 1,355 sqft $180,075
116 Gibson Hill Road Chester, NY 10918
Photo of 116 Gibson Hill Road, Chester, NY 10918 (MLS # 4801259)
0 beds 0 baths $26,000
18 Bridle Lane Chester, NY 10918
Photo of 18 Bridle Lane, Chester, NY 10918 (MLS # 4919923)
4 beds 3 baths 1,750 sqft $325,000
3621 Whispering Hills Chester, NY 10918
Photo of 3621 Whispering Hills, Chester, NY 10918 (MLS # 4920760)
3 beds 3 baths 1,331 sqft $230,000
2907 Whispering Hills Chester, NY 10918
Photo of 2907 Whispering Hills, Chester, NY 10918 (MLS # 4919672)
2 beds 2 baths 1,086 sqft $190,000
3104 Whispering Hills Chester, NY 10918
Photo of 3104 Whispering Hills, Chester, NY 10918 (MLS # 4840988)
3 beds 3 baths 1,331 sqft $210,000
61 Whitetail Run Chester, NY 10918
Photo of 61 Whitetail Run, Chester, NY 10918 (MLS # 4918061)
3 beds 3 baths 2,164 sqft $310,000
146 Rock Ridge Road Chester, NY 10918
Photo of 146 Rock Ridge Road, Chester, NY 10918 (MLS # 4913883)
4 beds 3 baths 2,793 sqft $475,000

Chester School Data

Chester School Districts

Chester Union Free School District
K-12

Chester Schools

Chester Elementary School
K-5, public
http://www.chesterufsd.org/elementary.cfm
Chester Academy Middle High School
6-12, public
Ohel Torah
10, private
Bellvale School
K-8, private