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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

4103 Whispering Hills Chester, NY 10918
Photo of 4103 Whispering Hills, Chester, NY 10918 (MLS # 4853120)
3 beds 3 baths 1,331 sqft $229,000
161 Main Street Chester, NY 10918
Photo of 161 Main Street, Chester, NY 10918 (MLS # 4853003)
2 beds 2 baths 1,152 sqft $129,900
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
143 Main Street, Unit 8 Chester, NY 10918
Photo of 143 Main Street, Unit 8, Chester, NY 10918 (MLS # 4852203)
0 beds 1 bath 250 sqft $950
54 Lehigh Avenue, Unit 1 Chester, NY 10918
Photo of 54 Lehigh Avenue, Unit 1, Chester, NY 10918 (MLS # 4850178)
2 beds 1 bath 1,064 sqft $1,375
22 Maple Avenue Chester, NY 10918
Photo of 22 Maple Avenue, Chester, NY 10918 (MLS # 4852049)
2 beds 2 baths 1,248 sqft $239,900
3504 Whispering Hills Chester, NY 10918
Photo of 3504 Whispering Hills, Chester, NY 10918 (MLS # 4851802)
3 beds 3 baths 1,331 sqft $224,999
11 Cherry Lane Chester, NY 10918
Photo of 11 Cherry Lane, Chester, NY 10918 (MLS # 4851526)
3 beds 3 baths 2,792 sqft $449,000
2 El Dorado Trail Chester, NY 10918
Photo of 2 El Dorado Trail, Chester, NY 10918 (MLS # 4851568)
0 beds 0 baths $149,900
39 Hambletonian Road Chester, NY 10918
Photo of 39 Hambletonian Road, Chester, NY 10918 (MLS # 4851637)
4 beds 4 baths 2,960 sqft $450,000
20 Grand View Terrace Chester, NY 10918
Photo of 20 Grand View Terrace, Chester, NY 10918 (MLS # 4851150)
4 beds 3 baths 3,072 sqft $469,900
24 Fields Lane Chester, NY 10918
Photo of 24 Fields Lane, Chester, NY 10918 (MLS # 4841440)
5 beds 3 baths 4,687 sqft $449,000
1217 Whispering Hills Chester, NY 10918
Photo of 1217 Whispering Hills, Chester, NY 10918 (MLS # 4850018)
2 beds 2 baths 1,053 sqft $169,900
6 Townsend Place Chester, NY 10918
Photo of 6 Townsend Place, Chester, NY 10918 (MLS # 4850837)
2 beds 2 baths 1,216 sqft $175,000
46 Greycourt Avenue Chester, NY 10918
Photo of 46 Greycourt Avenue, Chester, NY 10918 (MLS # 4849956)
3 beds 3 baths 1,655 sqft $239,900

Sold Listings in Chester

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
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
94 Whitetail Run Chester, NY 10918
Photo of 94 Whitetail Run, Chester, NY 10918 (MLS # 4824205)
4 beds 3 baths 3,958 sqft $600,000
646 Craigville Road Chester, NY 10918
Photo of 646 Craigville Road, Chester, NY 10918 (MLS # 4728389)
0 beds 0 baths $40,000
20 Oxford Depot Chester, NY 10918
Photo of 20 Oxford Depot, Chester, NY 10918 (MLS # 4838074)
4 beds 2 baths 1,500 sqft $167,000
14 June Road Chester, NY 10918
Photo of 14 June Road, Chester, NY 10918 (MLS # 4837067)
4 beds 3 baths 2,108 sqft $390,000
1302 Whispering Hills Chester, NY 10918
Photo of 1302 Whispering Hills, Chester, NY 10918 (MLS # 4836912)
3 beds 2 baths 1,316 sqft $135,000
595 Bull Mill Road Chester, NY 10918
Photo of 595 Bull Mill Road, Chester, NY 10918 (MLS # 4836605)
3 beds 2 baths 2,084 sqft $340,000
22 Lakeview Drive Chester, NY 10918
Photo of 22 Lakeview Drive, Chester, NY 10918 (MLS # 4836508)
3 beds 3 baths 1,848 sqft $279,000
5 Third Court Chester, NY 10918
Photo of 5 Third Court, Chester, NY 10918 (MLS # 4836468)
4 beds 2 baths 1,760 sqft $280,000
4318 Whispering Hills Chester, NY 10918
Photo of 4318 Whispering Hills, Chester, NY 10918 (MLS # 4836401)
2 beds 2 baths 1,086 sqft $165,000
55 Maple Avenue Chester, NY 10918
Photo of 55 Maple Avenue, Chester, NY 10918 (MLS # 4835312)
3 beds 2 baths 1,950 sqft $329,600
3404 Whispering Hills Chester, NY 10918
Photo of 3404 Whispering Hills, Chester, NY 10918 (MLS # 4835089)
3 beds 3 baths 1,331 sqft $200,500
1411 Kings Highway Chester, NY 10918
Photo of 1411 Kings Highway, Chester, NY 10918 (MLS # 4834974)
0 beds 0 baths $175,000
1601 Whispering Hills Drive Chester, NY 10918
Photo of 1601 Whispering Hills Drive, Chester, NY 10918 (MLS # 4834209)
2 beds 1 bath 1,084 sqft $149,760

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