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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

112 Green Meadows Way Chester, NY 10918
Photo of 112 Green Meadows Way, Chester, NY 10918 (MLS # 6006490)
1 bed 2 baths 717 sqft $124,900
1408 Whispering Hills Chester, NY 10918
Photo of 1408 Whispering Hills, Chester, NY 10918 (MLS # 6006078)
2 beds 2 baths 1,072 sqft $185,000
468 Bellvale Road Chester, NY 10918
Photo of 468 Bellvale Road, Chester, NY 10918 (MLS # 6005419)
3 beds 1 bath 1,324 sqft $315,900
16 Silvertail Road Chester, NY 10918
Photo of 16 Silvertail Road, Chester, NY 10918 (MLS # 4551897)
0 beds 0 baths $45,000
1460 St Hwy 17m Chester, NY 10918
Photo of 1460 St Hwy 17m, Chester, NY 10918 (MLS # 6002346)
0 beds 0 baths 9,536 sqft $2,700
6 Howland Street Chester, NY 10918
Photo of 6 Howland Street, Chester, NY 10918 (MLS # 6004444)
0 beds 0 baths 13,500 sqft $8
4017 Whispering Hills Road Chester, NY 10918
Photo of 4017 Whispering Hills Road, Chester, NY 10918 (MLS # 6001157)
2 beds 2 baths 1,072 sqft $1,650
1310 Whispering Hills Chester, NY 10918
Photo of 1310 Whispering Hills, Chester, NY 10918 (MLS # 6001681)
3 beds 3 baths 1,331 sqft $219,900
1107 Whispering Hills Chester, NY 10918
Photo of 1107 Whispering Hills, Chester, NY 10918 (MLS # 5124836)
2 beds 2 baths 1,086 sqft $174,900
40 Greycourt Avenue Chester, NY 10918
Photo of 40 Greycourt Avenue, Chester, NY 10918 (MLS # 6003013)
3 beds 3 baths 2,150 sqft $379,999
18 Silvertail Road Chester, NY 10918
Photo of 18 Silvertail Road, Chester, NY 10918 (MLS # 6002311)
4 beds 5 baths 5,063 sqft $845,000
15 Derose Lane Chester, NY 10918
Photo of 15 Derose Lane, Chester, NY 10918 (MLS # 5064409)
3 beds 3 baths 2,100 sqft $3,000
64 Goshen Road, Unit B Chester, NY 10918
Photo of 64 Goshen Road, Unit B, Chester, NY 10918 (MLS # 5123669)
2 beds 1 bath 1,200 sqft $1,600
6 Reputation Drive Chester, NY 10918
Photo of 6 Reputation Drive, Chester, NY 10918 (MLS # 4937734)
4 beds 3 baths 2,376 sqft $390,000
3177 State Route 94 Chester, NY 10918
Photo of 3177 State Route 94, Chester, NY 10918 (MLS # 5130357)
2 beds 1 bath 1,479 sqft $350,000

Sold Listings in Chester

17 Greycourt Road Chester, NY 10918
Photo of 17 Greycourt Road, Chester, NY 10918 (MLS # 5118513)
5 beds 2 baths 2,322 sqft $394,000
1406 Whispering Hills Chester, NY 10918
Photo of 1406 Whispering Hills, Chester, NY 10918 (MLS # 5118958)
2 beds 2 baths 1,086 sqft $189,900
4206 Whispering Hills Chester, NY 10918
Photo of 4206 Whispering Hills, Chester, NY 10918 (MLS # 4973330)
2 beds 2 baths 1,086 sqft $165,000
Brennan Court Chester, NY 10918
Photo of Brennan Court, Chester, NY 10918 (MLS # 4950800)
0 beds 0 baths $72,500
19 Reilly Road Chester, NY 10918
Photo of 19 Reilly Road, Chester, NY 10918 (MLS # 4961018)
4 beds 3 baths 1,936 sqft $299,000
14 Greycourt Road Chester, NY 10918
Photo of 14 Greycourt Road, Chester, NY 10918 (MLS # 5079141)
3 beds 2 baths 1,472 sqft $310,000
139 Odyssey Drive Chester, NY 10918
Photo of 139 Odyssey Drive, Chester, NY 10918 (MLS # 4938323)
4 beds 3 baths 3,216 sqft $305,000
3 Moffatt Lane Chester, NY 10918
Photo of 3 Moffatt Lane, Chester, NY 10918 (MLS # 5054806)
4 beds 2 baths 1,806 sqft $282,500
2210 Whispering Hills Chester, NY 10918
Photo of 2210 Whispering Hills, Chester, NY 10918 (MLS # 5061677)
3 beds 3 baths 1,331 sqft $190,000
35 Hudson Street Chester, NY 10918
Photo of 35 Hudson Street, Chester, NY 10918 (MLS # 5050375)
3 beds 3 baths 1,908 sqft $320,000
218 Hulsetown Road Chester, NY 10918
Photo of 218 Hulsetown Road, Chester, NY 10918 (MLS # 5042905)
3 beds 4 baths 4,066 sqft $375,000
14 Lori Lane Chester, NY 10918
Photo of 14 Lori Lane, Chester, NY 10918 (MLS # 5040154)
4 beds 3 baths 2,166 sqft $378,800
78 Surrey Road Chester, NY 10918
Photo of 78 Surrey Road, Chester, NY 10918 (MLS # 5033962)
4 beds 2 baths 1,820 sqft $285,000
142 Ridge Road Chester, NY 10918
Photo of 142 Ridge Road, Chester, NY 10918 (MLS # 5031594)
0 beds 0 baths 392 sqft $117,500
1705 Whispering Hills Avenue Chester, NY 10918
Photo of 1705 Whispering Hills Avenue, Chester, NY 10918 (MLS # 5030338)
2 beds 2 baths 1,072 sqft $180,000

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