Chester
Orange County, New York
6 Single Homes offered from $800,000+

Photo of 558 Pine Hill Road
$820,000
50
558 Pine Hill Road
Chester
 
4 Beds, 2 Full Bath, 1 Half Bath
78,408 sqft, 1.8 Acres
Age 36, Listed on Feb 26, 2026
schedule a tour
 
request info
Photo of * Lot #4 Wells Sweep Lane
$869,900
8
* Lot #4 Wells Sweep Lane
Chester
 
4 Beds, 2 Full Bath, 1 Half Bath
69,522 sqft, 1.6 Acres, 2 Garage
No Age, Listed on Mar 01, 2026
schedule a tour
 
request info
Photo of 12 Damian Court
$999,000
34
12 Damian Court
Chester
 
5 Beds, 4 Full Bath
130,680 sqft, 3 Acres, 3 Garage
Age 21, Listed on Jan 16, 2026
schedule a tour
 
request info
Photo of 53 Gibson Hill Road
$999,999
45
53 Gibson Hill Road
Chester
 
5 Beds, 4 Full Bath
135,036 sqft, 3.1 Acres, 3 Garage
Age 16,
schedule a tour
 
request info
Photo of 151 Kings Highway Bypass
$1,588,000
36
151 Kings Highway Bypass
Sugar Loaf
 
4 Beds, 5 Full Bath
630,662 sqft, 14.48 Acres
Age 4, Listed on May 31, 2024
schedule a tour
 
request info
Photo of 20 Goshen Road
$1,725,000
50
20 Goshen Road
Chester
 
4 Beds, 2 Full Bath, 1 Half Bath
2,308,680 sqft, 53 Acres, 3 Garage
Age 24, Listed on Feb 13, 2026
schedule a tour
 
request info