Skip to main content

MLS ID KEY985068Last updated Oct 21, 2026

Single Family

269 Watson Hollow Road

Active · Olive · Ulster County, NY 12494

Bedrooms
4 Beds
Bathrooms
3 Baths
Year built
1910
Est. monthly taxes
$1,075.21
Property gallery0 / 50
Loading photo…Photo unavailable

About this home

" MOVE IN CONDITION " 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.

Listing snapshot

Days on site
59 days
Listed on MLS
Apr 20, 2026
Full baths
1
Half baths
2
Annual property tax (MLS)
$12,902.46
Tax year
2025
Area source (MLS)
Public Records
Listing brokerage
Howard Hanna Rand Realty
MLS ID
KEY985068
Last updated
Oct 21, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1910
Garage
No
Parking
Driveway
Water source
Well
Sewer
Septic Tank
Utilities
See Remarks

Interior features

Basement
Full, Unfinished
Heating
Forced Air, Oil
Cooling
Central Air
Interior
Beamed Ceilings, Built-in Features, Ceiling Fan(s), Eat-in Kitchen, Entrance Foyer, Granite Counters
Appliances
Dishwasher, Dryer, Electric Cooktop, Electric Range, Freezer, Microwave, Refrigerator, Washer
Flooring
Ceramic Tile, Hardwood, Other
Fireplace
Yes
Fireplaces
1

Exterior features

Architectural style
Other
Construction materials
Vinyl Siding
Private pool
No

Schools (MLS)

Elementary school
Reginald Bennett Elementary School
Elementary school district
Onteora
Middle school
Onteora Middle School
Middle school district
Onteora
High school
Onteora High School
High school district
Onteora

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. Price changed to $750,000
  3. Price changed to $799,000
  4. First seen on this site
  5. MLS status changed

Location

Olive · Ulster County, NY 12494Show interactive map
269 Watson Hollow Road

Olive · Ulster County, NY 12494

Google Maps directions

Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.