Perched on top of a mountain with expansive views of the Catskills and stunning sunsets you find this exceptional Arts and Crafts home steeped in history. Standing in the middle of its' 32-acre lot, its location and position provide unmatched privacy and extensive outdoor space while being within 5 minutes of the lovely town of Catskill and 15 minutes from the city of Hudson, New York. Perfectly located in the middle of a booming Upstate NY scene, you are just 2 hours from New York City by car or by train. The residence, built in 1920, is a single-story home with three bedrooms and three bathrooms. It blends historical character with modern luxury. The spacious kitchen is a culinary haven, accommodating a 10-person dining table as well as two large window seats that offer stunning views west of the surrounding mountains. The chef's kitchen features a Wolf range, two ovens, a paneled refrigerator, a dishwasher, and an elegant wood-burning fireplace that sets the atmosphere for cozy dinners with family and friends. The home features a spacious living room with a second wood-burning fireplace and a primary bedroom suite with an en-suite bathroom. The third bedroom with ensuite bath is found in a separate structure perched on a hill above the main home accessed by a meandering stone staircase surrounded by lush mossy grounds and an original planter with a picturesque Japanese Maple tree. Outside, there is a heated, gunite saltwater pool surrounded by landscaped gardens and an open view of the mountains. There is also a whole-house generator and a water filtration system. The property has a rich historical background. It was originally built for British traveler and author Alleyne Ireland, known for his writings on British tropical colonies and his role as private secretary to Joseph Pulitzer. Alleyne's extensive travels in Asia and his close relationship with architect Frank Lloyd Wright inspired the style of the house. The land was painted by Thomas Cole, founder of the Hudson River School of landscape painting. 70 years later, the house was discovered in ruins by renowned NYC-based designer Stephen Shadley, who meticulously restored it. In a labor of love, Shadley took the structure down to its stone walls and fireplaces and built it again from the ground up in 2005. The roof, made of zinc tiles shipped specifically for the project from France, is only one of the touches of historic elegance that Shadley added to accentuate its unique character.
Single-familyProperty Type
1920Year Built
33.12 acresLot Size
$580Est. Price/Sq.Ft.
2 car garageParking
Listing by Marina T. Schindler Tatistcheff• Compass Greater NY LLC
Bought with Marina T. Schindler Tatistcheff• Compass Greater NY LLC
Forever views, high style and 1920's glamour will transport you to a time of grace, elegance and intrigue. This stunning stone cliffside retreat was conceived by writer of the day, Pulitzer protege, Alleyne Ireland, created through memories of his days in Darjeeling India, and affectionately named the property 'Little Darjeeling'. Here he frequently entertained intellects, politicians and the likes of Leggs Diamond and once you arrive you will understand why so many came and stayed endlessly at this hidden retreat. The interiors were brilliantly restored and renovated by renowned designer, Stephen Shadley (designer to Jen Aniston & Diane Keaton), creating a perfect mood. Gracious rooms flow and all access the front courtyard and lead to enclosed rear porches, taking in the incredible views. The expansive living room with grand fireplace open to the courtyard and lead to one phenomenal kitchen with its fireplace, where you will entertain in high style!
HVCRMLS #103104
May 18, 2015
Listed
$870,000
$322/sq ft
Public Records
Jan 11, 2002
Sold
$65,000
$24/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$17,464 (+8.7%)
$29,200 + $305,800
$335,000
2024
$16,073 (+1.3%)
$29,200 + $289,500
$318,700
2023
$15,873 (+0.4%)
$29,200 + $289,500
$318,700
2022
$15,807 (+1.4%)
$29,200 + $289,500
$318,700
2021
$15,590 (+1.5%)
$29,200 + $289,500
$318,700
2020
$15,356 (+3.8%)
$29,200 + $289,500
$318,700
2019
$14,789 (+3.2%)
$29,200 + $289,500
$318,700
2018
$14,336 (+5.9%)
$29,200 + $289,500
$318,700
2017
$13,539 (+0.7%)
$29,200 + $289,500
$318,700
2016
$13,449 (+0.2%)
$29,200 + $280,800
$310,000
2015
$13,417 (+2.6%)
$29,200 + $280,800
$310,000
2014
$13,072
$29,200 + $280,800
$310,000
Tax history for 5280 Cauterskill Rd
Year
Property tax
Land + Additions
Assessment*
2025
$17,464 (+8.7%)
$29,200 + $305,800
$335,000
2024
$16,073 (+1.3%)
$29,200 + $289,500
$318,700
2023
$15,873 (+0.4%)
$29,200 + $289,500
$318,700
2022
$15,807 (+1.4%)
$29,200 + $289,500
$318,700
2021
$15,590 (+1.5%)
$29,200 + $289,500
$318,700
2020
$15,356 (+3.8%)
$29,200 + $289,500
$318,700
2019
$14,789 (+3.2%)
$29,200 + $289,500
$318,700
2018
$14,336 (+5.9%)
$29,200 + $289,500
$318,700
2017
$13,539 (+0.7%)
$29,200 + $289,500
$318,700
2016
$13,449 (+0.2%)
$29,200 + $280,800
$310,000
2015
$13,417 (+2.6%)
$29,200 + $280,800
$310,000
2014
$13,072
$29,200 + $280,800
$310,000
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Beds
2
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
13 Acres
Year renovated
2006
Sq. Ft.
2,442
Year built
1925
Style
Vacant Land
County
Greene County
APN
192689A17100000010050000000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 22, 2026.
RA
Rural Residential/Agriculture District
These areas have soil conditions which generally are not conducive to intense development. They are located in the more rural areas of the Town and development which has already occurred here has taken place on large lots providing a low intensity of development. While the principal type of development should be residential, agriculture should continue in most areas and open-space types of commercial uses are allowed if properly located and designed.
Permitted uses
Include but are not limited to:
Agriculture
Equestrian facility
Housing-Single unit
Housing-Other
Lodging & hospitality
Housing-Mobile home park
Property details
Parking
Parking/Garage Information
Has Garage
# of Garage Spaces: 2
Interior
Bathroom Information
# of Full Bathrooms: 3
Heating & Cooling
Has Cooling
Cooling: Ceiling Fan(s), Central Air
Has Heating
Heating: Propane, Radiant
Interior Features
Interior Features: Beamed Ceilings, Ceiling Fan(s), High Speed Internet, Soaking Tub
Appliances: Dryer, Dishwasher, Gas Water Heater, Range, Refrigerator, Washer, Water Heater
Flooring: Wood
Has Fireplace
# of Fireplaces: 2
Fireplace Features: Kitchen, Living Room, Wood Burning
Room Information
# of Rooms Total: 6
Laundry Features: In Basement
Has Basement
Basement Details: Full
Exterior
Exterior Features
Exterior Features: Garden
Patio And Porch Features: Deck, Patio, Porch
Roof: Metal
Pool Information
Pool Features: Gunite, Heated
Building Information
Sq. Ft.: 2700.0
Construction Materials: Other, Stone
Foundation Details: Block
Property Features
Has View
Security Features: Security System
Other Equipment: Generator
Property Information
Property Type: Residential
Lot Information
Lot Features: Garden, Private, Views, Wooded
Road Surface Type: Paved
Road Responsibility: Private Maintained Road
Lot Size : 33.12
Lot Size Area: 33.12
Lot Size Units: Acres
Lot Size Acres: 33.12
Utilities
Utility Information
Water Source: Private, Well
Electric: Circuit Breakers
Sewer: Septic Tank
Location
Schools Information
High School District: Catskill School District
Location Information
Directions: Directions will be given at time of viewing
Public facts
Beds: 2
Baths: 2.0
Sq. Ft.: 2,442
Stories: 1.0
Lot Size: 13 acres
Style: Vacant Land
Year Built: 1925
Year Renovated: 2006
County: Greene County
APN: 192689A17100000010050000000
Home facts updated by county records on Jul 22, 2026
Around this home
Schools
Catskill Elementary School
Public PreK-5 • Assigned • 1.9mi
6/10
Catskill Middle School
Public 6-8 • Assigned • 2.0mi
5/10
Catskill Senior High School
Public 9-12 • Assigned • 1.9mi
4/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
3/10 Fire Factor
0.15% chance of being in a wildfire in next 30 years
3/10 Heat Factor
7 days above 99° expected this year, 16 days in 30 years
3/10 Wind Factor
7% chance of strong winds in next 30 years
2/10 Air Factor
0 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Catskill, NY • 12414
Average low and high temperatures (°F)
32
18
35
20
52
32
62
42
69
51
81
61
86
67
80
61
76
55
64
45
51
35
36
22
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 8.7 hours in
June and 3.6 hours in December, placing it below the
U.S. average for solar exposure.
8.7 hrs
3.6 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.49M – $1.80M
Sell confidently with a local market expert in Catskill. 3 minutes to get started.