269 Watson Hollow Road, Olive, NY 12494

← Back to search

$965,000

bedrooms

bathrooms

square feet

2,955

Acreage

Open Houses

year built

1910

Full Baths

Half Baths

Find out more

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.

Location
Subdivision	-
County	Ulster
Elementary School	Reginald Bennett
Middle School	Onteora
High School	Onteora

Driving directions

Open houses

None scheduled.

Find out more

Tell us who you are, and we will have someone reach out to you.

Name*

Email*

Phone*

Message

I have a house to sell

By proceeding, you consent to receive calls, texts and voicemails at the number you provided (may be recorded and may be autodialed and use pre-recorded and artificial voices), and email, from Kotohomes and their network of service providers about your inquiry and other home-related matters.

Msg/data rates may apply. This consent applies even if you are on a do not call list and is not a condition of any purchase.

MLS number: 985068

Listing agent: listing agent

Listing broker: Howard Hanna Kingston (845) 338-5252

Last update: Tuesday, June 9 2026 at 8:15 p.m. EDT

randrealty howardhanna