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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.
Property Type(s):
Single Family
| Last Updated | 5/11/2026 | Year Built | 1920 |
|---|---|---|---|
| Community | Olive | County | Ulster |
SCHOOLS
| Elementary School | Bennett 4-6 |
|---|
Price History
| Prior to May 11, '26 | $1,295,000 |
|---|---|
| May 11, '26 - Today | $1,200,000 |
Additional Details
| AIR | Ceiling Fan(s), CENTRAL AIR |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | DISHWASHER, DRYER, Electric Oven, Electric Range, FREEZER, MICROWAVE, REFRIGERATOR, WASHER |
| AREA | Olive |
| BASEMENT | FULL, UNFINISHED, Yes |
| CONSTRUCTION | Vinyl Siding |
| FIREPLACE | Yes |
| HEAT | FORCED AIR, Oil |
| INTERIOR | Beamed Ceilings, Bookcases, Built-in Features, Ceiling Fan(s), Eat-in Kitchen, Entrance Foyer, Granite Counters |
| LOT | 16.5 acre(s) |
| LOT DESCRIPTION | Back Yard, Front Yard, LANDSCAPED, Native Plants |
| LOT DIMENSIONS | 16.5 |
| SEWER | Septic Tank |
| STYLE | Arts & Crafts |
| TAXES | 14510 |
| VIEW | Yes |
| VIEW DESCRIPTION | Creek/Stream, Garden, Mountain(s), Pond |
| WATER | Private, Well |
Location
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Listed with Howard Hanna Rand Realty
IDX information © 2026 by the Hudson Valley Catskills Region Multiple List Service. All Rights Reserved.
The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskills Region Multiple List Service.
Information is deemed reliable but is not guaranteed accurate by the MLS. 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.
This IDX solution is (c) Diverse Solutions 2026.
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