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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 (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
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
2 Wood Road Chester, NY 10918
Photo of 2 Wood Road, Chester, NY 10918 (MLS # 4826123)
3 beds 2 baths 1,366 sqft $289,900
7 Murray Drive Chester, NY 10918
Photo of 7 Murray Drive, Chester, NY 10918 (MLS # 4747119)
4 beds 3 baths 3,035 sqft $399,999
7 Country Woods Drive Chester, NY 10918
Photo of 7 Country Woods Drive, Chester, NY 10918 (MLS # 4832709)
4 beds 3 baths 4,542 sqft $548,000
17 Vivian Lane Chester, NY 10918
Photo of 17 Vivian Lane, Chester, NY 10918 (MLS # 4832770)
4 beds 2 baths 1,780 sqft $200,000
86 Beverly Road Chester, NY 10918
Photo of 86 Beverly Road, Chester, NY 10918 (MLS # 4831449)
4 beds 3 baths 4,004 sqft $529,900
141 Creamery Pond Road Chester, NY 10918
Photo of 141 Creamery Pond Road, Chester, NY 10918 (MLS # 4832526)
4 beds 3 baths 2,830 sqft $464,900
2512 Whispering Hills Chester, NY 10918
Photo of 2512 Whispering Hills, Chester, NY 10918 (MLS # 4830769)
2 beds 1 bath 1,084 sqft $175,000
11 MAIN Street Chester, NY 10918
Photo of 11 MAIN Street, Chester, NY 10918 (MLS # 4832197)
0 beds 0 baths 1,932 sqft $209,900
16 Lori Lane Chester, NY 10918
Photo of 16 Lori Lane, Chester, NY 10918 (MLS # 4831538)
4 beds 5 baths 5,225 sqft $759,900
65 Main Street Chester, NY 10918
Photo of 65 Main Street, Chester, NY 10918 (MLS # 4830812)
4 beds 3 baths 2,390 sqft $319,900
143 Conklingtown Road Chester, NY 10918
Photo of 143 Conklingtown Road, Chester, NY 10918 (MLS # 4803356)
4 beds 4 baths 2,852 sqft $605,000
139 Odyssey Drive Chester, NY 10918
Photo of 139 Odyssey Drive, Chester, NY 10918 (MLS # 4827272)
4 beds 3 baths 3,216 sqft $475,000

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
256 Sugarloaf Mountain Road Chester, NY 10918
Photo of 256 Sugarloaf Mountain Road, Chester, NY 10918 (MLS # 4820671)
2 beds 2 baths 1,208 sqft $275,000
20 Split Rock Road Chester, NY 10918
Photo of 20 Split Rock Road, Chester, NY 10918 (MLS # 4819593)
4 beds 3 baths 2,706 sqft $500,000
40 Maple Avenue Chester, NY 10918
Photo of 40 Maple Avenue, Chester, NY 10918 (MLS # 4819708)
3 beds 1 bath 1,132 sqft $172,371
126 Pine Hill Road Chester, NY 10918
Photo of 126 Pine Hill Road, Chester, NY 10918 (MLS # 4814869)
3 beds 3 baths 2,562 sqft $430,000
4018 Whispering Hills Chester, NY 10918
Photo of 4018 Whispering Hills, Chester, NY 10918 (MLS # 4814046)
2 beds 2 baths 1,086 sqft $165,000
11 Stone Mountain Trail Chester, NY 10918
Photo of 11 Stone Mountain Trail, Chester, NY 10918 (MLS # 4813207)
3 beds 3 baths 2,499 sqft $550,000
2704 Whispering Hills Chester, NY 10918
Photo of 2704 Whispering Hills, Chester, NY 10918 (MLS # 4812554)
3 beds 3 baths 1,331 sqft $212,450
23 Mari Road Chester, NY 10918
Photo of 23 Mari Road, Chester, NY 10918 (MLS # 4812207)
4 beds 2 baths 2,098 sqft $165,000
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
62 Pewter Circle Chester, NY 10918
Photo of 62 Pewter Circle, Chester, NY 10918 (MLS # 4810787)
3 beds 3 baths 1,902 sqft $292,500
209 Oxford Road Chester, NY 10918
Photo of 209 Oxford Road, Chester, NY 10918 (MLS # 4809929)
3 beds 3 baths 2,737 sqft $309,000
103 Greycourt Road Chester, NY 10918
Photo of 103 Greycourt Road, Chester, NY 10918 (MLS # 4809684)
4 beds 3 baths 1,900 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