5280 Cauterskill Road, Catskill, NY 12414
OFF MARKET

5280 Cauterskill Road
Catskill, NY 12414

  • 3 Beds
  • 3 Baths
  • 2,700 sqft (on 33.12 acres)

$1,886,000

Trulia Estimate
as of Jun 16, 2026
Est. Refi. Payment $11,974/mo*

$1,886,000

Trulia Estimate
as of Jun 16, 2026
Est. Refi. Payment $11,974/mo*
3 Beds
3 Baths
2,700 sqft
(on 33.12 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

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

Active Status

MLS Status: Closed

Interior Features

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

Exterior Features

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

Property Information

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

Price & Status

Price
List Price: $1,825,000
Status Change & Dates
Off Market Date: Fri Mar 28 2025

Location

Direction & Address
City: Catskill
School Information
High School District: Catskill School District

Building

Building Area
Building Area: 2700 Square Feet

HOA

No HOA

Lot Information

Lot Area: 33.12 Acres

Offer

Listing Terms: If And When (IAW)

Miscellaneous

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

DatePriceEventSource
05/10/2025$1,825,000PendingHVCRMLS #153877
05/05/2025$1,800,000Sold
HVCRMLS #153877
11/26/2024$1,825,000ListingRemovedColumbia Greene Northern Dutchess MLS #153877
10/11/2024$1,825,000PriceChange
Columbia Greene Northern Dutchess MLS #153877
08/11/2024$1,975,000Listed For SaleColumbia Greene Northern Dutchess MLS #153877
09/30/2016$660,000Sold
HVCRMLS #110523
01/11/2002$65,000Sold
N/A

Market trends in Catskill

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
33
2
MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
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.
Skip to last item
Skip to first item

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.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 5280 Cauterskill Road.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • Bing Bin
    "Catskill is a lovely town. Friendly neighborhood. Safe and quiet. Great place for living. We all love here. "
  • Bing Bin
    "It’s safe for kids to live here. They can bicycle and play in the neighborhood. Pets friendly. Neighbors are friendly. "
  • Lionel O.
    "We don’t commute here. It’s a two hour commute to the city. So if you live here you are either nearby or not working "
  • Trulia User
    "It is a nice neighborhood to walk dogs. People clean up after their pets and are respectful of their neighbors and each other. "
  • Eureka W.
    "It’s nice Very quiet neighbors are very friendlyNice area for trick-or-treating and all holidays very festive great restaurants. Need a car though"
  • R.
    "Beautiful and idyllic. Really feels like one of the most specials places in the Catskills. There are farmers, people from the city with 2nd homes, hunters, and multigenerational families all living in harmony. "
  • Raybu1960
    "I enjoy taking my grandson to the park occassionally. being down by the River is beautiful . I grew within one mile of the River as a child and am comforted by its constancy and tidal nature. and I have seen very large channel catfish caught out of that River . the River of Washington Irving and RIP Van Winkle. I also like the connecting trails to the Monastery and the Cohatr Preserve. I also appreciate the Rams Horn Sanctuary with its small feeder creeks and large tower. Catskill in both rich in history and nature . I will miss it but not NY overall with its exorbitant taxes and rank liberal freedom robbing politics. I cant wait to sell my house and get the heck moving south and west."
  • Trulia User
    "GREAT PLACE TO LIVE and have kid. Great place to go if u retired and love the country and animals and small town "
  • Frank C.
    "Catskill is great but it’s a dying town.. there’s buildings falling apart and stores are closed all over the place and there’s a massive drug problem! It’s great if you like living in a depressed dying town..."
  • Gaby B
    "it's a small town which provides a level of intimacy in the community that makes it feel like home. "
  • homeowner
    "Plenty of snakes for dogs to eat. Lots of shouting at night and fist fights between college students. Dog's poop shows up well on snow and icy sheets that line our unshovelled sidewalks. A dog park by the river is shady. Plenty of fast food litter in the streets for dogs to eat."
  • Michelle R.
    "I’ve lived in this part of Catskill for 1 1/2 years and in the community for 7 1/2 years. It is a good community."
  • Ehd247
    "none. we have no neighborhood events. Most of the neighbors are latch. key. Ther er is nothing more to say about our neighborhood. The river I'd near by and also a park."
  • Eureka W.
    "there's a doggy park for doggies it's really nice to have a lot of Open Spaces a lot of trees play things for them to play with check it out"
  • Chucknrenaye
    "Neighborhood is great. I love Catskill. The schooling needs improvement but is ok. Neighbors stay to themselves. Sometimes noisy. "
  • Ehd247
    "I've lived in this neighborhood for 48 years. I also grew up in this neighborhood for 19 years before that. my neighborhood is unique because many of the houses on my street were designed by the same architect "
  • Chucknrenaye
    "It’s a friendly neighborhood I own horses and love the country I would love to hear nothing but the crickets chirping "
  • Shameeka
    "some of the people here are friendly but The neighborhood is great. And I would love to live here but the rent is to high for me"

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

Explore by feature - Air Conditioning

Explore by feature - Washer/dryer

Homes for sale near 5280 Cauterskill Road

Skip to last item
Skip to first item

Off Market Homes Near 5280 Cauterskill Road

Skip to last item
Skip to first item
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.
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.