Jump To:

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

7 Marion Street Chester, NY 10918
Photo of 7 Marion Street, Chester, NY 10918 (MLS # 4842023)
4 beds 3 baths 2,744 sqft $340,000
19 Carpenter Road Chester, NY 10918
Photo of 19 Carpenter Road, Chester, NY 10918 (MLS # 4817780)
4 beds 2 baths 1,344 sqft $178,000
1213 Whispering Hills Chester, NY 10918
Photo of 1213 Whispering Hills, Chester, NY 10918 (MLS # 4843130)
2 beds 1 bath 1,084 sqft $165,000
316 Sugarloaf Mountain Road Chester, NY 10918
Photo of 316 Sugarloaf Mountain Road, Chester, NY 10918 (MLS # 4842154)
2 beds 2 baths 1,885 sqft $389,000
210 Green Meadows Way Chester, NY 10918
Photo of 210 Green Meadows Way, Chester, NY 10918 (MLS # 4842145)
1 bed 2 baths 747 sqft $1,250
166 Bull Mill Road Chester, NY 10918
Photo of 166 Bull Mill Road, Chester, NY 10918 (MLS # 4812937)
3 beds 1 bath 1,004 sqft $189,000
78 High Street, Unit 6 Chester, NY 10918
Photo of 78 High Street, Unit 6, Chester, NY 10918 (MLS # 4840279)
2 beds 1 bath 900 sqft $1,450
375 Bellvale Road Chester, NY 10918
Photo of 375 Bellvale Road, Chester, NY 10918 (MLS # 4842216)
0 beds 0 baths 2,816 sqft $524,900
4113 Whispering Hills Chester, NY 10918
Photo of 4113 Whispering Hills, Chester, NY 10918 (MLS # 4841949)
2 beds 1 bath 1,118 sqft $174,900
240 Sugarloaf Mountain Road Chester, NY 10918
Photo of 240 Sugarloaf Mountain Road, Chester, NY 10918 (MLS # 4841951)
4 beds 3 baths 3,416 sqft $374,900
70 Conklingtown Road Chester, NY 10918
Photo of 70 Conklingtown Road, Chester, NY 10918 (MLS # 4816774)
3 beds 1 bath 835 sqft $149,000
66 Pewter Circle Chester, NY 10918
Photo of 66 Pewter Circle, Chester, NY 10918 (MLS # 4841866)
3 beds 3 baths 1,880 sqft $279,000
10 Wood Road Chester, NY 10918
Photo of 10 Wood Road, Chester, NY 10918 (MLS # 4841759)
3 beds 2 baths 1,746 sqft $319,900
285 Bull Mill Road Chester, NY 10918
Photo of 285 Bull Mill Road, Chester, NY 10918 (MLS # 4840199)
3 beds 3 baths 2,729 sqft $435,000
3 Heidi Lane Chester, NY 10918
Photo of 3 Heidi Lane, Chester, NY 10918 (MLS # 4840490)
6 beds 6 baths 6,152 sqft $929,900

Sold Listings in Chester

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
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
86 Beverly Road Chester, NY 10918
Photo of 86 Beverly Road, Chester, NY 10918 (MLS # 4831449)
4 beds 3 baths 4,004 sqft $535,000
16 Lori Lane Chester, NY 10918
Photo of 16 Lori Lane, Chester, NY 10918 (MLS # 4831538)
4 beds 5 baths 4,624 sqft $735,000
4 Bridle Lane Chester, NY 10918
Photo of 4 Bridle Lane, Chester, NY 10918 (MLS # 4829256)
4 beds 2 baths 1,872 sqft $293,000
4103 Whispering Hills Chester, NY 10918
Photo of 4103 Whispering Hills, Chester, NY 10918 (MLS # 4829198)
3 beds 3 baths 1,331 sqft $140,000
202 Green Meadows Way Chester, NY 10918
Photo of 202 Green Meadows Way, Chester, NY 10918 (MLS # 4826758)
1 bed 2 baths 747 sqft $119,900
3124 Whispering Hills, Unit 3124 Chester, NY 10918
Photo of 3124 Whispering Hills, Unit 3124, Chester, NY 10918 (MLS # 4821790)
2 beds 1 bath 1,084 sqft $154,000
985 Craigville Road Chester, NY 10918
Photo of 985 Craigville Road, Chester, NY 10918 (MLS # 4737862)
4 beds 4 baths 3,100 sqft $485,000
37 Eagle Crest Way Chester, NY 10918
Photo of 37 Eagle Crest Way, Chester, NY 10918 (MLS # 4819676)
4 beds 3 baths 3,250 sqft $545,000
3208 Whispering Hills Chester, NY 10918
Photo of 3208 Whispering Hills, Chester, NY 10918 (MLS # 4825722)
2 beds 2 baths 1,072 sqft $165,000
17 Farmers Lane Chester, NY 10918
Photo of 17 Farmers Lane, Chester, NY 10918 (MLS # 4825532)
4 beds 3 baths 4,096 sqft $528,500
6 White Horse Lane Chester, NY 10918
Photo of 6 White Horse Lane, Chester, NY 10918 (MLS # 4825394)
4 beds 3 baths 2,312 sqft $430,000
4108 Whispering Hills Chester, NY 10918
Photo of 4108 Whispering Hills, Chester, NY 10918 (MLS # 4819251)
2 beds 2 baths 1,072 sqft $170,000

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