New Listing - 04/20/2026
269 Watson Hollow Road, Olive, (West Shokan), NY, 12494
12 rooms
4 beds
1 Full / 2 Half baths
1910
Other
2,955 sqft
Set in the quiet, storied hills of West Shokan, 269 Watson Hollow Road offers a rare blend of historic character and natural beauty. Originally constructed in the 1800s as a barn, this distinctive home was thoughtfully relocated across the stream approximately 40 years ago, where it now rests gracefully against the mountain backdrop.16.5 acres extend to the top of the ridge behind the house. Beyond that is NYC property. Inside, the home showcases its heritage with stunning original chestnut beams--many of which remain structural and weight-bearing--bringing warmth, authenticity, and architectural significance to the living space. A striking chimney, masterfully crafted both inside and out by a local mason, serves as a centerpiece, anchoring the home with timeless craftsmanship. The setting is equally compelling. A pristine, swimmable spring-fed pond invites peaceful afternoons and reflects the surrounding mountain landscape, creating a private retreat-like atmosphere. The property is accessed by a DOT-approved bridge, accommodating oil and propane deliveries with ease--an important and valuable feature for year-round living. This is a truly special offering where history, craftsmanship, and nature converge--ideal for those seeking a one-of-a-kind Catskills escape or full-time residence steeped in charm and character.
Status:
Active
Town:
Olive
Type:
Single-family residential
Laundry Remarks:
In Bathroom
Heating:
Forced Air, Oil
Cooling:
Central Air
Basement:
Full, Unfinished
Parking:
Driveway
Acreage:
16.5
Est. Taxes:
$12,902
Assessment
$701,000
Construction
Vinyl Siding
Utilities
See Remarks
Lot Description:
Back Yard, Landscaped
Elementary School:
Reginald Bennett Elementary School
Middle School:
Onteora Middle School
High School:
Onteora High School
School District:
Onteora
Days on Market:
1
Appliances:
Dishwasher, Dryer, Electric Cooktop, Electric Range, Freezer, Microwave, Refrigerator, Washer
MLS #:
985068
Community Info
School Info
Walk Score
Mass Transit
Yelp
Listing courtesy of HOWARD HANNA RAND REALTY 845-338-5252