269 Watson Hollow Road, West Shokan

$1,295,000

4 Beds
2 Baths
2,955 Sqft
16½ Acres
0 Garage

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.

Essential Information
MLS® #20261714
Price$1,295,000
Bedrooms4
Bathrooms2.00
Full Baths1
Half Baths2
Square Footage2,955
Acres16.50
Year Built1920
TypeResidential
Sub-TypeSingle Family Residence
StyleArts & Crafts
StatusActive
Community Information
Address269 Watson Hollow Road
AreaOlive
CityWest Shokan
CountyUlster
StateNY
Zip Code12494
View

Creek/Stream, Garden, Mountain(s), Pond

Interior
HeatingForced Air, Oil
CoolingCentral Air
FireplaceYes
# of Fireplaces1
FireplacesLiving Room, Propane
Interior Features

3 Seasons Room, Beamed Ceilings, Bookcases, Built-in Features, Ceiling Fan(s), Eat-in Kitchen, Entrance Foyer, Granite Counters

Appliances

Washer, Refrigerator, Microwave, Freezer, Electric Range, Electric Oven, Dryer, Dishwasher

Exterior
ExteriorVinyl Siding
RoofAsbestos Shingle
ConstructionVinyl Siding
Lot Description

Pond on Lot, Back Yard, Front Yard, Landscaped, Native Plants

School Information
ElementaryBennett 4-6
District

Onteora Central School District

Additional Information
Zoning03
Listing Details
AgentJeanne Boice
Listing Courtesy of Howard Hanna Rand Realty
LISTING MAP

Get directions to this property:

Ulster County Board of Realtors Logo The data relating to real estate on this website comes in part from the IDX of the Multiple Listing Service of Ulster County, Inc. Real estate listings held by brokerage firms other than Flemming Realty are marked with IDX logo and the detailed information about them includes the name of the listing broker.

Copyright © 2026 by the Multiple Listing Service of Ulster County, Inc. All Rights Reserved.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.