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ActivePrice cut: $49K (9/29)
$750,000
4beds
2,955sqft

269 Watson Hollow Road, West Shokan, NY 12494

4beds
2,955sqft
Single family residence
Built in 1920
16.50 Acres
No data
$254 price/sqft

What's special

Dot-approved bridgeOriginal chestnut beamsPrivate retreat-like atmospherePristine swimmable spring-fed pond

Set in the quiet, storied hills of West Shokan, 269 Watson Hollow Road offers a rare blend of historic character and natural beauty Move right into this gorgeous Historic 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.

167 days
|
1,194
|
100
|
Source: HVCRMLS,MLS#: 20261714MLS Logo
Travel times

Living Room

Kitchen

Dining Room

Zillow last checked:

Listing updated:

Listed by:

Howard Hanna Rand Realty 845-338-5252,

Jeanne Boice 914-388-7405

Source: HVCRMLS,MLS#: 20261714MLS Logo

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 4
  • Bathrooms: 3
  • Full bathrooms: 1
  • 1/2 bathrooms: 2
Primary bedroom
  • Level: Second
  • Area: 304
  • Dimensions: 16 x 19
Bedroom
  • Level: Second
  • Area: 90
  • Dimensions: 9 x 10
Bedroom
  • Level: Second
  • Area: 150
  • Dimensions: 10 x 15
Bedroom
  • Level: Second
  • Area: 117
  • Dimensions: 13 x 9
Dining room
  • Level: First
  • Area: 168
  • Dimensions: 12 x 14
Kitchen
  • Level: First
  • Area: 220
  • Dimensions: 10 x 22
Living room
  • Level: First
  • Area: 459
  • Dimensions: 17 x 27
Other
  • Description: Bluestone porch
  • Level: First
  • Area: 260
  • Dimensions: 13 x 20
Heating
  • Forced Air, Oil
Cooling
  • Central Air
Appliances
  • Included: Washer, Refrigerator, Microwave, Freezer, Electric Range, Electric Oven, Dryer, Dishwasher
  • Laundry: In Bathroom, Main Level
Features
  • 3 Seasons Room, Beamed Ceilings, Bookcases, Built-in Features, Ceiling Fan(s), Eat-in Kitchen, Entrance Foyer, Granite Counters
  • Flooring: Ceramic Tile, Hardwood, Stone
  • Basement: Partial,Unfinished
  • Number of fireplaces: 1
  • Fireplace features: Living Room, Propane
Interior area
  • Total structure area: 2,955
  • Total interior livable area: 2,955 sqft
  • Finished area above ground: 2,955
  • Finished area below ground: 0

Property

Features
  • Patio & porch: Enclosed, Patio, Porch
  • Fencing: Back Yard,Fenced
  • Has view: Yes
  • View description: Creek/Stream, Garden, Mountain(s), Pond
  • Has water view: Yes
  • Water view: Creek/Stream,Pond
Lot
  • Size: 16.5 Acres
  • Features: Pond on Lot, Back Yard, Front Yard, Landscaped, Native Plants
Details
  • Additional structures: Shed(s)
  • Parcel number: 400004500100010421000000
  • Zoning: 03

Construction

Type & style
  • Home type: SingleFamily
  • Architectural style: Arts & Crafts
  • Property subtype: Single Family Residence
Materials
  • Vinyl Siding
  • Roof: Asphalt
Condition
  • New construction: No
  • Year built: 1920

Utilities & green energy

  • Electric: 200+ Amp Service, Generator
  • Sewer: Septic Tank
  • Water: Well

Community & HOA

Location
  • Region: West Shokan

Financial & listing details

  • Price per square foot: $254/sqft
  • Tax assessed value: $1,175,000
  • Annual tax amount: $14,510
  • Date on market: 4/20/2026

Price history

DateEventPrice
9/29/2026Price change$750,000-6.1%$254/sqft
Source: HVCRMLS #20261714
9/17/2026Price change$799,000-5.9%$270/sqft
Source: HVCRMLS #20261714
8/21/2026Price change$849,000-5.6%$287/sqft
Source: HVCRMLS #20261714
7/20/2026Price change$899,000-2.8%$304/sqft
Source: HVCRMLS #20261714
7/1/2026Price change$925,000-4.1%$313/sqft
Source: HVCRMLS #20261714
6/9/2026Price change$965,000-12.3%$327/sqft
Source: HVCRMLS #20261714
5/27/2026Price change$1,100,000-8.3%$372/sqft
Source: HVCRMLS #20261714
5/11/2026Price change$1,200,000-7.3%$406/sqft
Source: HVCRMLS #20261714
4/20/2026Listed for sale$1,295,000$438/sqft
Source: HVCRMLS #20261714

Public tax history

YearProperty taxesTax assessment
2025-- $1,175,000 +67.6%
2024-- $701,000
2023-- $701,000
2022-- $701,000 +19.9%
2021-- $584,700 +8.9%
2020-- $536,700
2019-- $536,700
2018-- $536,700
2017$10,063 $536,700
2016-- $536,700
2015-- $536,700
2014-- $536,700
2013-- $536,700
2011-- $536,700
2010-- $536,700
2009-- $536,700
2008-- $536,700
2007-- $536,700
2006-- $536,700 +29389%
2005-- $1,820
2004-- $1,820
2003-- $1,820
2002-- $1,820
2001-- $1,820
2000-- $1,820

Find assessor info on the county website

Monthly payment

Estimated monthly payment$1,822
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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Estimated market value

$772,200

$734,000 - $811,000

$4,726/mo

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: 12494

Nearby schools

Reginald Bennett Elementary School
Grades K-5 • 3.6 miles
8/10
GreatSchools® Rating
Test Score Rating
8/10
Student Progress Rating
8/10
Onteora Middle School
Grades 6-8 • 3.6 miles
9/10
GreatSchools® Rating
Test Score Rating
8/10
Student Progress Rating
10/10
Onteora High School
Grades 9-12 • 3.6 miles
7/10
GreatSchools® Rating
Test Score Rating
7/10
College Readiness Rating
6/10