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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

21 Rachel Drive Chester, NY 10918
Photo of 21 Rachel Drive, Chester, NY 10918 (MLS # 4916248)
3 beds 3 baths 2,528 sqft $379,900
16 Primrose Lane Chester, NY 10918
Photo of 16 Primrose Lane, Chester, NY 10918 (MLS # 4909978)
4 beds 3 baths 2,466 sqft $500,000
25 Goshen Road Chester, NY 10918
Photo of 25 Goshen Road, Chester, NY 10918 (MLS # 4910247)
4 beds 4 baths 3,218 sqft $495,000
106 Long Vista Lane Chester, NY 10918
Photo of 106 Long Vista Lane, Chester, NY 10918 (MLS # 4911246)
4 beds 4 baths 4,550 sqft $645,000
3 Jackson Street, Unit 1 Chester, NY 10918
Photo of 3 Jackson Street, Unit 1, Chester, NY 10918 (MLS # 4913782)
2 beds 1 bath 700 sqft $1,000
1816 Whispering Hills Chester, NY 10918
Photo of 1816 Whispering Hills, Chester, NY 10918 (MLS # 4914960)
3 beds 3 baths 1,331 sqft $237,500
109 Hambletonian Road Chester, NY 10918
Photo of 109 Hambletonian Road, Chester, NY 10918 (MLS # 4915202)
0 beds 0 baths $245,000
1351 Kings Highway Chester, NY 10918
Photo of 1351 Kings Highway, Chester, NY 10918 (MLS # 4914856)
0 beds 0 baths $79,950
7 Park Place Chester, NY 10918
Photo of 7 Park Place, Chester, NY 10918 (MLS # 4915265)
4 beds 4 baths 2,780 sqft $450,000
26 Neal Drive Chester, NY 10918
Photo of 26 Neal Drive, Chester, NY 10918 (MLS # 4913736)
4 beds 3 baths 2,612 sqft $485,000
234 Glenmere Road Chester, NY 10918
Photo of 234 Glenmere Road, Chester, NY 10918 (MLS # 4912021)
3 beds 3 baths 2,435 sqft $2,400
1 Primrose Lane Chester, NY 10918
Photo of 1 Primrose Lane, Chester, NY 10918 (MLS # 4914635)
4 beds 5 baths 3,731 sqft $729,000
358 Bull Mill Road Chester, NY 10918
Photo of 358 Bull Mill Road, Chester, NY 10918 (MLS # 4914471)
5 beds 3 baths 3,120 sqft $375,000
322 Black Meadow Road Chester, NY 10918
Photo of 322 Black Meadow Road, Chester, NY 10918 (MLS # 4914132)
4 beds 3 baths 2,394 sqft $399,900
66 Murray Drive Chester, NY 10918
Photo of 66 Murray Drive, Chester, NY 10918 (MLS # 4913919)
4 beds 4 baths 3,084 sqft $349,000

Sold Listings in Chester

2508 Whispering Hills Chester, NY 10918
Photo of 2508 Whispering Hills, Chester, NY 10918 (MLS # 4839606)
2 beds 2 baths 1,072 sqft $155,000
14 Speranza Court Chester, NY 10918
Photo of 14 Speranza Court, Chester, NY 10918 (MLS # 4742958)
3 beds 3 baths 2,130 sqft $351,718
2920 Whispering Hills Chester, NY 10918
Photo of 2920 Whispering Hills, Chester, NY 10918 (MLS # 4901815)
2 beds 2 baths 1,072 sqft $165,000
19 Carpenter Road Chester, NY 10918
Photo of 19 Carpenter Road, Chester, NY 10918 (MLS # 4856847)
4 beds 2 baths 1,744 sqft $255,000
4009 Whispering Hills Chester, NY 10918
Photo of 4009 Whispering Hills, Chester, NY 10918 (MLS # 4856522)
3 beds 3 baths 1,331 sqft $230,000
2 Vivian Lane Chester, NY 10918
Photo of 2 Vivian Lane, Chester, NY 10918 (MLS # 4855724)
4 beds 2 baths 1,788 sqft $235,000
22 Greycourt Road Chester, NY 10918
Photo of 22 Greycourt Road, Chester, NY 10918 (MLS # 4855239)
3 beds 4 baths 1,949 sqft $358,500
107 Creamery Pond Road Chester, NY 10918
Photo of 107 Creamery Pond Road, Chester, NY 10918 (MLS # 4839057)
3 beds 3 baths 2,712 sqft $366,000
26 Elm Street Chester, NY 10918
Photo of 26 Elm Street, Chester, NY 10918 (MLS # 4854003)
4 beds 3 baths 2,310 sqft $339,000
2907 Whispering Hills Chester, NY 10918
Photo of 2907 Whispering Hills, Chester, NY 10918 (MLS # 4853927)
2 beds 2 baths 1,086 sqft $121,000
12 Surrey Road Chester, NY 10918
Photo of 12 Surrey Road, Chester, NY 10918 (MLS # 4852970)
4 beds 2 baths 2,020 sqft $329,900
4103 Whispering Hills Chester, NY 10918
Photo of 4103 Whispering Hills, Chester, NY 10918 (MLS # 4853120)
3 beds 3 baths 1,331 sqft $225,000
188 Farmingdale Road Chester, NY 10918
Photo of 188 Farmingdale Road, Chester, NY 10918 (MLS # 4851656)
3 beds 2 baths 2,444 sqft $429,900
3504 Whispering Hills Chester, NY 10918
Photo of 3504 Whispering Hills, Chester, NY 10918 (MLS # 4851802)
3 beds 3 baths 1,331 sqft $220,000
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

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