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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

1216 whispering Hills Chester, NY 10918
Photo of 1216 whispering Hills, Chester, NY 10918 (MLS # 5024830)
3 beds 3 baths 1,331 sqft $219,900
26 High Street, Unit A Chester, NY 10918
Photo of 26 High Street, Unit A, Chester, NY 10918 (MLS # 5020101)
1 bed 2 baths 850 sqft $1,200
13 Primrose Lane Chester, NY 10918
Photo of 13 Primrose Lane, Chester, NY 10918 (MLS # 5022482)
4 beds 3 baths 2,742 sqft $675,000
18 High Street Chester, NY 10918
Photo of 18 High Street, Chester, NY 10918 (MLS # 5023591)
1 bed 1 bath 550 sqft $750
26 Park Drive Chester, NY 10918
Photo of 26 Park Drive, Chester, NY 10918 (MLS # 5021337)
3 beds 1 bath 1,624 sqft $299,900
4309 Whispering Hills, Unit 377 Chester, NY 10918
Photo of 4309 Whispering Hills, Unit 377, Chester, NY 10918 (MLS # 5012631)
3 beds 3 baths 1,355 sqft $2,150
1418 Whispering Hills Chester, NY 10918
Photo of 1418 Whispering Hills, Chester, NY 10918 (MLS # 5022478)
2 beds 3 baths 1,086 sqft $1,675
28 Hubshop Road Chester, NY 10918
Photo of 28 Hubshop Road, Chester, NY 10918 (MLS # 5015247)
3 beds 2 baths 1,880 sqft $350,000
21 Gailie Drive Chester, NY 10918
Photo of 21 Gailie Drive, Chester, NY 10918 (MLS # 5016225)
0 beds 0 baths 800 sqft $78,900
526 Bull Mill Road Chester, NY 10918
Photo of 526 Bull Mill Road, Chester, NY 10918 (MLS # 5018161)
5 beds 6 baths 4,622 sqft $654,000
16 Primrose Lane Chester, NY 10918
Photo of 16 Primrose Lane, Chester, NY 10918 (MLS # 5009879)
4 beds 3 baths 2,466 sqft $3,200
64 Goshen Road, Unit A Chester, NY 10918
Photo of 64 Goshen Road, Unit A, Chester, NY 10918 (MLS # 5009770)
3 beds 1 bath 1,400 sqft $1,900
3803 whispering hills Place Chester, NY 10918
Photo of 3803 whispering hills Place, Chester, NY 10918 (MLS # 5003514)
3 beds 3 baths 1,331 sqft $225,900
15 Twin Brooks Drive Chester, NY 10918
Photo of 15 Twin Brooks Drive, Chester, NY 10918 (MLS # 5012331)
4 beds 3 baths 2,092 sqft $329,900
1708 Whispering Hills Chester, NY 10918
Photo of 1708 Whispering Hills, Chester, NY 10918 (MLS # 5015808)
2 beds 2 baths 1,053 sqft $1,850

Sold Listings in Chester

21 Meadow Avenue Chester, NY 10918
Photo of 21 Meadow Avenue, Chester, NY 10918 (MLS # 4918202)
4 beds 4 baths 2,444 sqft $237,000
18 High Street Chester, NY 10918
Photo of 18 High Street, Chester, NY 10918 (MLS # 4916966)
4 beds 4 baths 2,274 sqft $165,087
6 Townsend Place Chester, NY 10918
Photo of 6 Townsend Place, Chester, NY 10918 (MLS # 4850837)
2 beds 2 baths 1,216 sqft $134,900
1813 Whispering Hills Chester, NY 10918
Photo of 1813 Whispering Hills, Chester, NY 10918 (MLS # 4940382)
2 beds 1 bath 1,084 sqft $167,750
2716 Whispering Hills Chester, NY 10918
Photo of 2716 Whispering Hills, Chester, NY 10918 (MLS # 4938716)
3 beds 3 baths 1,331 sqft $212,000
114 Old Mansion Road Chester, NY 10918
Photo of 114 Old Mansion Road, Chester, NY 10918 (MLS # 4922521)
4 beds 2 baths 3,330 sqft $400,000
2611 Whispering Hills Chester, NY 10918
Photo of 2611 Whispering Hills, Chester, NY 10918 (MLS # 4936592)
3 beds 2 baths 1,316 sqft $198,900
1052 Craigville Road Chester, NY 10918
Photo of 1052 Craigville Road, Chester, NY 10918 (MLS # 4935363)
3 beds 4 baths 3,240 sqft $635,000
12 Green Drive Chester, NY 10918
Photo of 12 Green Drive, Chester, NY 10918 (MLS # 4922689)
3 beds 3 baths 2,042 sqft $360,000
24 Lakeview Drive Chester, NY 10918
Photo of 24 Lakeview Drive, Chester, NY 10918 (MLS # 4930699)
3 beds 3 baths 1,848 sqft $329,000
7 Damian Court Chester, NY 10918
Photo of 7 Damian Court, Chester, NY 10918 (MLS # 4926358)
4 beds 3 baths 3,308 sqft $550,000
3824 Whispering Hills Drive Chester, NY 10918
Photo of 3824 Whispering Hills Drive, Chester, NY 10918 (MLS # 4928779)
2 beds 1 bath 1,084 sqft $160,000
39 Boville Court Chester, NY 10918
Photo of 39 Boville Court, Chester, NY 10918 (MLS # 4748360)
4 beds 3 baths 3,207 sqft $449,900
4 King Street Chester, NY 10918
Photo of 4 King Street, Chester, NY 10918 (MLS # 4927245)
3 beds 2 baths 2,012 sqft $250,000
66 Dug Road Chester, NY 10918
Photo of 66 Dug Road, Chester, NY 10918 (MLS # 4927569)
3 beds 2 baths 1,992 sqft $189,900

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