Recently Sold Homes in Chester, NY

74 homes

Use arrow keys to navigate
SOLD
AUG 14, 2026
$685,000
4 Beds
2.5 Baths
3,100 sqft
9 Derose Lane,
Chester, NY 10918
Howard Hanna Rand Realty
Use arrow keys to navigate
SOLD
AUG 12, 2026
$500,000
3 Beds
2 Baths
1,778 sqft
1 N Hudson Street,
Chester, NY 10918
KW Hudson Valley United
Use arrow keys to navigate
SOLD
AUG 6, 2026
$107,500
2 Imperial Park,
Chester, NY 10918
HomeSmart Homes & Estates
Use arrow keys to navigate
SOLD
AUG 4, 2026
$450,000
3 Beds
2 Baths
1,882 sqft
5 Roggia Road,
Chester, NY 10918
Nazma Real Estate LLC
Use arrow keys to navigate
SOLD
AUG 3, 2026
$998,999
4 Beds
3.5 Baths
4,467 sqft
53 Odyssey Drive,
Chester, NY 10918
Howard Hanna Rand Realty
Use arrow keys to navigate
SOLD
JUL 17, 2026
$369,900
3 Beds
2.5 Baths
1,331 sqft
3910 Whispering Hills,
Chester, NY 10918
eXp Realty
Use arrow keys to navigate
SOLD
JUL 14, 2026
$742,500
4 Beds
3.5 Baths
3,356 sqft
55 Beverly Road,
Chester, NY 10918
Howard Hanna Rand Realty
SOLD
JUL 13, 2026
$589,000
3 Beds
2.5 Baths
1,854 sqft
101 Whitetail Run,
Chester, NY 10918
Cronin & Company Real Estate
SOLD
JUL 8, 2026
$340,000
2 Beds
2 Baths
1,316 sqft
2323 Whispering Hills,
Chester, NY 10918
Century 21 Full Service Realty
SOLD
JUL 8, 2026
$700,000
4 Beds
3.5 Baths
2,780 sqft
7 Park Place,
Chester, NY 10918
Century 21 Full Service Realty
SOLD
JUL 7, 2026
$830,000
4 Beds
2.5 Baths
2,722 sqft
5 Gabriels Drive,
Chester, NY 10918
Q Home Sales
SOLD
JUL 6, 2026
$385,000
3 Beds
2.5 Baths
1,355 sqft
4116 Whispering Hills,
Chester, NY 10918
William Raveis-New York, LLC
SOLD
JUL 1, 2026
$370,000
1 Bed
1 Bath
783 sqft
58 Oxford Springs Road,
Chester, NY 10918
Keller Williams Realty
SOLD
JUL 1, 2026
$525,000
3 Beds
2.5 Baths
1,888 sqft
4 Oak Street,
Chester, NY 10918
Cronin & Company Real Estate
SOLD
JUN 25, 2026
$770,000
4 Beds
3 Baths
2,780 sqft
1071 Craigville Rd,
Chester, NY 10918
MS Realty Group USA, Inc
SOLD
JUN 22, 2026
$635,000
3 Beds
2.5 Baths
1,954 sqft
25 Sugarloaf Mountain Road,
Chester, NY 10918
Cronin & Company Real Estate
SOLD
JUN 18, 2026
$905,000
5 Beds
3.5 Baths
3,680 sqft
21 Bull Mine Road,
Chester, NY 10918
Howard Hanna Rand Realty
SOLD
JUN 16, 2026
$295,000
3 Beds
2.5 Baths
1,331 sqft
1503 Whispering Hills,
Chester, NY 10918
Century 21 E & M Williams Rlty
SOLD
JUN 16, 2026
$717,000
4 Beds
2.5 Baths
3,020 sqft
278 Gibson Hill Rd,
Chester, NY 10918
SOLD
JUN 14, 2026
$437,000
3 Beds
1.5 Baths
1,056 sqft
71 Greycourt Road,
Chester, NY 10918
Blooming Realty
SOLD
JUN 14, 2026
$720,000
4 Beds
2.5 Baths
3,112 sqft
15 Old Dominion Road,
Blooming Grove, NY 10914
Blooming Realty
SOLD
JUN 11, 2026
$348,000
3 Beds
2.5 Baths
1,331 sqft
2203 Whispering Hills,
Chester, NY 10918
Howard Hanna Rand Realty
SOLD
JUN 8, 2026
$690,000
5 Beds
2.5 Baths
3,124 sqft
9 Country Woods Drive,
Chester, NY 10918
Howard Hanna Rand Realty
SOLD
JUN 5, 2026
$305,000
2 Beds
1.5 Baths
1,072 sqft
3917 Whispering Hills,
Chester, NY 10918
Keller Williams Hudson Valley
SOLD
JUN 5, 2026
$296,000
2 Beds
1 Bath
1,084 sqft
3601 Whispering Hills #3601,
Chester, NY 10918
Weichert Realtors
SOLD
JUN 1, 2026
$660,000
4 Beds
2.5 Baths
2,506 sqft
34 Booth Road,
Chester, NY 10918
Century 21 Full Service Realty
SOLD
MAY 29, 2026
$315,000
2 Beds
1 Bath
1,272 sqft
307 Gibson Hill Road,
Chester, NY 10918
Howard Hanna Rand Realty
SOLD
MAY 27, 2026
$725,000
3 Beds
3 Baths
2,870 sqft
16 Oxford Springs Road,
Chester, NY 10918
RE/MAX Benchmark Realty Group
SOLD
MAY 21, 2026
$445,000
2 Beds
2 Baths
1,998 sqft
31 Hudson Street,
Chester, NY 10918
BHG Real Estate Green Team
SOLD
APR 20, 2026
$300,000
2 Beds
1.5 Baths
1,072 sqft
4508 Whispering Hills,
Chester, NY 10918
eXp Realty
SOLD
APR 17, 2026
$288,000
2 Beds
1 Bath
1,084 sqft
2913 Whispering Hills,
Chester, NY 10918
HomeSmart Homes & Estates
SOLD
APR 17, 2026
$1,225,000
11 Beds
6.5 Baths
4,327 sqft
10 Damian Court,
Chester, NY 10918
MS Realty Group USA, Inc
SOLD
APR 9, 2026
$290,000
2 Beds
1.5 Baths
1,072 sqft
3308 Whispering Hills Drive,
Chester, NY 10918
Howard Hanna Rand Realty
SOLD
APR 7, 2026
$299,000
2 Beds
1.5 Baths
1,072 sqft
3120 Whispering Hills,
Chester, NY 10918
John J Lease REALTORS Inc
SOLD
APR 1, 2026
$460,000
2 Beds
2 Baths
1,714 sqft
391 Bull Mill Road,
Chester, NY 10918
Century 21 Realty Center
SOLD
MAR 27, 2026
$385,000
4 Beds
2 Baths
1,364 sqft
13 Carpenter Rd,
Chester, NY 10918
SOLD
MAR 27, 2026
$610,000
3 Beds
2 Baths
1,876 sqft
44 Cedar Pond Ln,
Chester, NY 10918
SOLD
MAR 25, 2026
$382,000
3 Beds
2.5 Baths
1,331 sqft
2915 Whispering Hills,
Chester, NY 10918
Century 21 Full Service Realty
SOLD
MAR 12, 2026
$610,000
3 Beds
2 Baths
1,876 sqft
44 Cedar Pond Lane,
Chester, NY 10918
eXp Realty
SOLD
MAR 11, 2026
$260,000
3 Beds
2.5 Baths
1,331 sqft
2104 Whispering Hills,
Chester, NY 10918
ARC Realty 1 in Sales

Based on information submitted to the MLS GRID as of 2026-08-14 10:48:11 PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information