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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

2716 Whispering Hills Chester, NY 10918
Photo of 2716 Whispering Hills, Chester, NY 10918 (MLS # 4938716)
3 beds 3 baths 1,331 sqft $224,900
38 Rebecca Road Chester, NY 10918
Photo of 38 Rebecca Road, Chester, NY 10918 (MLS # 4935983)
4 beds 3 baths 1,910 sqft $378,000
118 Green Meadows Way Chester, NY 10918
Photo of 118 Green Meadows Way, Chester, NY 10918 (MLS # 4938435)
1 bed 2 baths 717 sqft $1,300
25 Natures Trail Chester, NY 10918
Photo of 25 Natures Trail, Chester, NY 10918 (MLS # 4931813)
4 beds 3 baths 2,346 sqft $925,000
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 $499,900
6 Reputation Drive Chester, NY 10918
Photo of 6 Reputation Drive, Chester, NY 10918 (MLS # 4937734)
4 beds 3 baths 2,376 sqft $424,900
48 Beverly Road Chester, NY 10918
Photo of 48 Beverly Road, Chester, NY 10918 (MLS # 4937966)
4 beds 4 baths 2,292 sqft $529,000
26 Hulsetown Road, Unit 26D Chester, NY 10918
Photo of 26 Hulsetown Road, Unit 26D, Chester, NY 10918 (MLS # 4936673)
1 bed 1 bath 650 sqft $1,500
3118 Whispering Hills Chester, NY 10918
Photo of 3118 Whispering Hills, Chester, NY 10918 (MLS # 4932951)
2 beds 2 baths 1,086 sqft $1,800
1820 Whispering Hills Chester, NY 10918
Photo of 1820 Whispering Hills, Chester, NY 10918 (MLS # 4937399)
2 beds 2 baths 1,072 sqft $1,600
2611 Whispering Hills Chester, NY 10918
Photo of 2611 Whispering Hills, Chester, NY 10918 (MLS # 4936592)
3 beds 2 baths 1,316 sqft $199,900
14 Red Fox Run Chester, NY 10918
Photo of 14 Red Fox Run, Chester, NY 10918 (MLS # 4934756)
4 beds 3 baths 3,308 sqft $499,900
4316 Whispering Hills Chester, NY 10918
Photo of 4316 Whispering Hills, Chester, NY 10918 (MLS # 4935712)
3 beds 3 baths 1,331 sqft $179,000
1052 Craigville Road Chester, NY 10918
Photo of 1052 Craigville Road, Chester, NY 10918 (MLS # 4935363)
3 beds 4 baths 3,240 sqft $659,999
88 Murray Drive Chester, NY 10918
Photo of 88 Murray Drive, Chester, NY 10918 (MLS # 4934432)
3 beds 3 baths 2,418 sqft $389,900

Sold Listings in Chester

116 Gibson Hill Road Chester, NY 10918
Photo of 116 Gibson Hill Road, Chester, NY 10918 (MLS # 4801259)
0 beds 0 baths $26,000
3104 Whispering Hills Chester, NY 10918
Photo of 3104 Whispering Hills, Chester, NY 10918 (MLS # 4840988)
3 beds 3 baths 1,331 sqft $210,000
2911 Whispering Hills Chester, NY 10918
Photo of 2911 Whispering Hills, Chester, NY 10918 (MLS # 4913963)
3 beds 2 baths 1,316 sqft $195,100
54 Main Street Chester, NY 10918
Photo of 54 Main Street, Chester, NY 10918 (MLS # 4913507)
4 beds 3 baths 2,320 sqft $271,950
105 Main Street Chester, NY 10918
Photo of 105 Main Street, Chester, NY 10918 (MLS # 4908560)
3 beds 3 baths 2,264 sqft $257,500
3118 Whispering Hills Chester, NY 10918
Photo of 3118 Whispering Hills, Chester, NY 10918 (MLS # 4906259)
2 beds 2 baths 1,086 sqft $179,000
16 Carpenter Road Chester, NY 10918
Photo of 16 Carpenter Road, Chester, NY 10918 (MLS # 4906244)
3 beds 2 baths 1,075 sqft $235,000
221 OXFORD Road Chester, NY 10918
Photo of 221 OXFORD Road, Chester, NY 10918 (MLS # 4905839)
4 beds 4 baths 4,600 sqft $710,000
14 Goshen Road Chester, NY 10918
Photo of 14 Goshen Road, Chester, NY 10918 (MLS # 4905415)
4 beds 3 baths 2,743 sqft $419,000
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
388 Bull Mill Road Chester, NY 10918
Photo of 388 Bull Mill Road, Chester, NY 10918 (MLS # 4905434)
4 beds 3 baths 2,888 sqft $329,000
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
2706 Whispering Hills Chester, NY 10918
Photo of 2706 Whispering Hills, Chester, NY 10918 (MLS # 4904725)
2 beds 2 baths 1,086 sqft $174,000
58 Maple Avenue Chester, NY 10918
Photo of 58 Maple Avenue, Chester, NY 10918 (MLS # 4904258)
4 beds 3 baths 2,640 sqft $358,000
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

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