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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

69 Brookside (3016) Avenue Chester, NY 10918
Photo of 69 Brookside (3016) Avenue, Chester, NY 10918 (MLS # 4832888)
0 beds 0 baths 43,952 sqft $12
69 Brookside (1580) Avenue Chester, NY 10918
Photo of 69 Brookside (1580) Avenue, Chester, NY 10918 (MLS # 4832886)
0 beds 0 baths 43,952 sqft $10
69 Brookside (1310) Avenue Chester, NY 10918
Photo of 69 Brookside (1310) Avenue, Chester, NY 10918 (MLS # 4832879)
0 beds 0 baths 43,952 sqft $12
20 Bianca Boulevard Chester, NY 10918
Photo of 20 Bianca Boulevard, Chester, NY 10918 (MLS # 4902026)
3 beds 3 baths 2,260 sqft $275,000
2920 Whispering Hills Chester, NY 10918
Photo of 2920 Whispering Hills, Chester, NY 10918 (MLS # 4901815)
2 beds 2 baths 1,072 sqft $167,900
208 Green Meadows Way Chester, NY 10918
Photo of 208 Green Meadows Way, Chester, NY 10918 (MLS # 4901574)
1 bed 2 baths 717 sqft $1,200
241 Meadow Avenue Chester, NY 10918
Photo of 241 Meadow Avenue, Chester, NY 10918 (MLS # 4901808)
4 beds 2 baths 1,560 sqft $279,000
9 Stargate Lane Chester, NY 10918
Photo of 9 Stargate Lane, Chester, NY 10918 (MLS # 4901599)
4 beds 3 baths 2,830 sqft $399,900
3 Stewart Lane Chester, NY 10918
Photo of 3 Stewart Lane, Chester, NY 10918 (MLS # 4901334)
2 beds 1 bath 810 sqft $139,900
7 Murray Drive Chester, NY 10918
Photo of 7 Murray Drive, Chester, NY 10918 (MLS # 4900577)
4 beds 3 baths 3,035 sqft $394,900
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 $385,000
66 Pewter Circle Chester, NY 10918
Photo of 66 Pewter Circle, Chester, NY 10918 (MLS # 4841866)
3 beds 3 baths 1,880 sqft $259,000
55 Brookside Avenue Chester, NY 10918
Photo of 55 Brookside Avenue, Chester, NY 10918 (MLS # 4900536)
0 beds 0 baths 2,394 sqft $1,800
11 Booth Road Chester, NY 10918
Photo of 11 Booth Road, Chester, NY 10918 (MLS # 4837009)
4 beds 3 baths 3,160 sqft $224,900
7 Oxford Depot Road Chester, NY 10918
Photo of 7 Oxford Depot Road, Chester, NY 10918 (MLS # 4802362)
0 beds 0 baths 3,480 sqft $399,900

Sold Listings in Chester

27 Park Drive Chester, NY 10918
Photo of 27 Park Drive, Chester, NY 10918 (MLS # 4846223)
5 beds 2 baths 2,000 sqft $295,000
17 Wood Road Chester, NY 10918
Photo of 17 Wood Road, Chester, NY 10918 (MLS # 4850723)
3 beds 2 baths 1,644 sqft $225,000
186 Greycourt Road Chester, NY 10918
Photo of 186 Greycourt Road, Chester, NY 10918 (MLS # 4846106)
3 beds 2 baths 1,913 sqft $299,000
3106 Whispering Hills Chester, NY 10918
Photo of 3106 Whispering Hills, Chester, NY 10918 (MLS # 4847695)
2 beds 2 baths 1,090 sqft $149,216
11 Townsend Place Chester, NY 10918
Photo of 11 Townsend Place, Chester, NY 10918 (MLS # 4847376)
3 beds 2 baths 1,788 sqft $265,000
61 Nancy Lane Chester, NY 10918
Photo of 61 Nancy Lane, Chester, NY 10918 (MLS # 4833572)
3 beds 3 baths 2,700 sqft $395,000
1916 Whispering Hills Drive Chester, NY 10918
Photo of 1916 Whispering Hills Drive, Chester, NY 10918 (MLS # 4847198)
3 beds 3 baths 1,331 sqft $185,000
1707 Whispering Hills Drive Chester, NY 10918
Photo of 1707 Whispering Hills Drive, Chester, NY 10918 (MLS # 4845675)
2 beds 2 baths 1,086 sqft $157,000
2204 Whispering Hills Chester, NY 10918
Photo of 2204 Whispering Hills, Chester, NY 10918 (MLS # 4845030)
3 beds 3 baths 1,331 sqft $196,000
1913 Whispering Hills Chester, NY 10918
Photo of 1913 Whispering Hills, Chester, NY 10918 (MLS # 4845024)
2 beds 1 bath 1,084 sqft $150,000
19 Carpenter Road Chester, NY 10918
Photo of 19 Carpenter Road, Chester, NY 10918 (MLS # 4817780)
4 beds 2 baths 1,344 sqft $157,106
316 Sugarloaf Mountain Road Chester, NY 10918
Photo of 316 Sugarloaf Mountain Road, Chester, NY 10918 (MLS # 4842154)
2 beds 2 baths 1,885 sqft $395,000
23 Farmers Lane Chester, NY 10990
Photo of 23 Farmers Lane, Chester, NY 10990 (MLS # 4841935)
3 beds 3 baths 2,000 sqft $415,000
375 Bellvale Road Chester, NY 10918
Photo of 375 Bellvale Road, Chester, NY 10918 (MLS # 4842216)
0 beds 0 baths 2,816 sqft $430,000
4113 Whispering Hills Chester, NY 10918
Photo of 4113 Whispering Hills, Chester, NY 10918 (MLS # 4841949)
2 beds 1 bath 1,118 sqft $172,500

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