5280 Cauterskill Road
Catskill, NY 12414
- 3 Beds
- 3 Baths
- 2,700 sqft (on 33.12 acres)
3 Beds
3 Baths
2,700 sqft
(on 33.12 acres)
Local Information
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Description
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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from May 12, 2025
Home Highlights
Parking
Garage
Outdoor
Porch, Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 5280 Cauterskill Road
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MLS Status: Closed |
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Interior Details Basement: FullNumber of Rooms: 6 |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3 |
Dimensions and Layout Living Area: 2700 Square Feet |
Appliances & Utilities Appliances: Water Heater, Washer, Refrigerator, Range, Gas Water Heater, Dryer, DishwasherDishwasherDryerLaundry: In BasementRefrigeratorWasher |
Heating & Cooling Heating: Propane,RadiantHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Propane |
Fireplace & Spa Number of Fireplaces: 2Fireplace: Kitchen, Living Room, Wood BurningHas a Fireplace |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Flooring: Wood |
Levels, Entrance, & Accessibility Floors: Wood |
View Has a ViewView: Rural, Valley |
Security Security: Security System |
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Exterior Home Features Roof: MetalPatio / Porch: Deck, Patio, PorchExterior: GardenFoundation: BlockGarden |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Garage |
Pool Pool: Gunite, Heated |
Frontage Road Surface Type: PavedNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
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Year Built Year Built: 1920 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Arts & Crafts,Cottage |
Building Construction Materials: Stone, OtherNot a New ConstructionNot Attached Property |
Property Information Parcel Number: 171.0015 |
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Price List Price: $1,825,000 |
Status Change & Dates Off Market Date: Fri Mar 28 2025 |
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Direction & Address City: Catskill |
School Information High School District: Catskill School District |
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Building Area Building Area: 2700 Square Feet |
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No HOA |
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Lot Area: 33.12 Acres |
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Listing Terms: If And When (IAW) |
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BasementMls Number: 153877Showing Advance Notice: 24 |
Last check for updates: about 3 hours ago
Listed by Marina Tatistcheff, (917) 319-7570
Compass Greater NY LLC
Bought with: Marina Tatistcheff, (917) 319-7570, Compass Greater NY LLC
Source: HVCRMLS, MLS#153877

Price History for 5280 Cauterskill Road
| Date | Price | Event | Source |
|---|---|---|---|
| 05/10/2025 | $1,825,000 | Pending | HVCRMLS #153877 |
| 05/05/2025 | $1,800,000 | Sold | HVCRMLS #153877 |
| 11/26/2024 | $1,825,000 | ListingRemoved | Columbia Greene Northern Dutchess MLS #153877 |
| 10/11/2024 | $1,825,000 | PriceChange | Columbia Greene Northern Dutchess MLS #153877 |
| 08/11/2024 | $1,975,000 | Listed For Sale | Columbia Greene Northern Dutchess MLS #153877 |
| 09/30/2016 | $660,000 | Sold | HVCRMLS #110523 |
| 01/11/2002 | $65,000 | Sold | N/A |
Market trends in Catskill
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
33
2MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $1,196,429 |
Home facts updated by county records
Homeowner tools
Estimated monthly rent$4,180/mo
Homes for rent near 5280 Cauterskill Road
See what comparable homes in the neighborhood are renting for.Comparable Sales for 5280 Cauterskill Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.24 | Single-Family Home | $175,000 | 03/30/26 | 4 | 1 | 1,440 | |
0.90 | Single-Family Home | $580,000 | 04/24/26 | 5 | 2 | 2,016 | |
1.38 | Single-Family Home | $950,000 | 06/25/25 | 3 | 2.5 | 2,551 | |
0.53 | Single-Family Home | $45,000 | 01/12/26 | 3 | 1 | 1,032 | |
1.45 | Single-Family Home | $543,200 | 06/05/26 | 3 | 3 | 2,837 | |
1.02 | Single-Family Home | $455,000 | 01/22/26 | 2 | 2 | 1,192 | |
1.37 | Single-Family Home | $495,000 | 09/19/25 | 3 | 2 | 1,708 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 5280 Cauterskill Road.
What Locals Say about Catskill
At least 78 Trulia users voted on each feature.
88 % Say car is needed
85 % Say it's dog friendly
79 % Say yards are well-kept
79 % Say parking is easy
75 % Say people would walk alone at night
67 % Say there's wildlife
66 % Say there's holiday spirit
65 % Say there are sidewalks
64 % Say kids play outside
60 % Say it's walkable to restaurants
58 % Say neighbors are friendly
55 % Say they plan to stay for at least 5 years
54 % Say streets are well-lit
53 % Say it's quiet
48 % Say it's walkable to grocery stores
37 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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IDX information © 2026 by the Hudson Valley Catskill Region MLS. All Rights Reserved.
The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS.
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.
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.
5280 Cauterskill Road, Catskill, NY 12414 is a 3 bedroom, 3 bathroom, 2,700 sqft single-family home built in 1920. This property is not currently available for sale. 5280 Cauterskill Road was last sold on May 5, 2025 for $1,800,000 (1% lower than the asking price of $1,825,000). The current Trulia Estimate for 5280 Cauterskill Road is $1,886,000.

