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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

9 El Dorado Trail Chester, NY 10918
Photo of 9 El Dorado Trail, Chester, NY 10918 (MLS # 5095435)
0 beds 0 baths $169,000
15 Pewter Circle Chester, NY 10918
Photo of 15 Pewter Circle, Chester, NY 10918 (MLS # 5101925)
5 beds 3 baths 3,223 sqft $439,000
71 Greycourt Road Chester, NY 10918
Photo of 71 Greycourt Road, Chester, NY 10918 (MLS # 5098393)
3 beds 2 baths 1,056 sqft $180,000
19 Reilly Road Chester, NY 10918
Photo of 19 Reilly Road, Chester, NY 10918 (MLS # 4961018)
4 beds 2 baths 1,936 sqft $299,000
54 Main Street Chester, NY 10918
Photo of 54 Main Street, Chester, NY 10918 (MLS # 5099397)
4 beds 3 baths 2,230 sqft $399,999
25 Saddle Hill Road Chester, NY 10918
Photo of 25 Saddle Hill Road, Chester, NY 10918 (MLS # 5098463)
4 beds 4 baths 3,777 sqft $549,900
26 A Hulsetown Road Chester, NY 10918
Photo of 26 A Hulsetown Road, Chester, NY 10918 (MLS # 5096636)
4 beds 3 baths 2,500 sqft $3,000
4022 Whispering Hills Chester, NY 10918
Photo of 4022 Whispering Hills, Chester, NY 10918 (MLS # 5090395)
3 beds 3 baths 1,331 sqft $2,150
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
355 Bellvale Road Chester, NY 10918
Photo of 355 Bellvale Road, Chester, NY 10918 (MLS # 5093997)
1 bed 1 bath 900 sqft $1,100
1406 Whispering Hills Chester, NY 10918
Photo of 1406 Whispering Hills, Chester, NY 10918 (MLS # 5094407)
2 beds 2 baths 1,086 sqft $189,900
208 Farmingdale Road Chester, NY 10918
Photo of 208 Farmingdale Road, Chester, NY 10918 (MLS # 4915954)
3 beds 3 baths 2,116 sqft $365,000
159 Pine Hill Road Chester, NY 10918
Photo of 159 Pine Hill Road, Chester, NY 10918 (MLS # 5090759)
4 beds 4 baths 2,700 sqft $420,000
476 Bellvale Road Chester, NY 10918
Photo of 476 Bellvale Road, Chester, NY 10918 (MLS # 5090695)
4 beds 3 baths 2,934 sqft $464,900
131 Laroe Road Chester, NY 10918
Photo of 131 Laroe Road, Chester, NY 10918 (MLS # 5090719)
4 beds 3 baths 2,496 sqft $389,000

Sold Listings in Chester

3423 Whispering Hills Chester, NY 10918
Photo of 3423 Whispering Hills, Chester, NY 10918 (MLS # 5011336)
3 beds 2 baths 1,316 sqft $211,000
1912 Whispering Hills Chester, NY 10918
Photo of 1912 Whispering Hills, Chester, NY 10918 (MLS # 5002535)
2 beds 1 bath 1,084 sqft $110,000
18 Butler Terrace Chester, NY 10918
Photo of 18 Butler Terrace, Chester, NY 10918 (MLS # 5000117)
4 beds 2 baths 1,629 sqft $270,000
3 Stacey Lane Chester, NY 10918
Photo of 3 Stacey Lane, Chester, NY 10918 (MLS # 4817196)
3 beds 3 baths 2,904 sqft $448,200
2503 Whispering Hills Chester, NY 10918
Photo of 2503 Whispering Hills, Chester, NY 10918 (MLS # 4982202)
3 beds 3 baths 1,331 sqft $220,000
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
3314 Whispering Hills Chester, NY 10918
Photo of 3314 Whispering Hills, Chester, NY 10918 (MLS # 4974789)
3 beds 2 baths 1,316 sqft $226,500
8 Damian Court Chester, NY 10918
Photo of 8 Damian Court, Chester, NY 10918 (MLS # 4973545)
5 beds 4 baths 3,588 sqft $550,000
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
2008 Whispering Hills Chester, NY 10918
Photo of 2008 Whispering Hills, Chester, NY 10918 (MLS # 4947788)
2 beds 2 baths 1,050 sqft $175,000
4022 Whispering Hills Chester, NY 10918
Photo of 4022 Whispering Hills, Chester, NY 10918 (MLS # 4951610)
3 beds 3 baths 1,331 sqft $209,250
7 Camelback Road Chester, NY 10918
Photo of 7 Camelback Road, Chester, NY 10918 (MLS # 4950926)
5 beds 5 baths 4,025 sqft $660,000
3151 Route 94 Chester, NY 10918
Photo of 3151 Route 94, Chester, NY 10918 (MLS # 4933959)
4 beds 4 baths 2,450 sqft $433,540
84 Fox Hill Road Chester, NY 10918
Photo of 84 Fox Hill Road, Chester, NY 10918 (MLS # 4916773)
4 beds 3 baths 2,392 sqft $465,000
87 Whitetail Run Chester, NY 10918
Photo of 87 Whitetail Run, Chester, NY 10918 (MLS # 4944831)
3 beds 3 baths 2,340 sqft $350,000

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