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$4,999,000

Sale Pending
18 Striebel Rd, Woodstock, NY 12498
4 Beds
4 Baths
3,899 Square Feet
58.87 Acres Lot
Built in 1914
Sale Pending
Units n/a
Checked: 1 day ago
Updated: Aug 14, 2025 at 04:54AM

Investment Summary


Monthly Cash Flow
-$26,225
Cap Rate
-0.2%
Cash-on-Cash Return
-27.4%
Debt Coverage Ratio
-0.04
Internal Rate of Return (5 years)
-22.4%

Property Description


58.87 Acres Lot
Built in 1914
Sale Pending
Units n/a

Nestled in the heart of Woodstock, this extraordinary 70+ acre estate is a rare offering of artistic heritage, architectural beauty, and serene natural surroundings. Known as The Stone House on Striebel Road, this iconic bluestone compound has stood at the crossroads of music, literature, and counterculture for over a century. Built in 1914 as a country retreat, the main Stone House features 4 bedrooms, 2 full baths, and 2 half baths, with rich period details throughout—including original carved woodwork, wide-plank floors, historic fireplaces, and Dutch doors that enhance both charm and function. One of the home's standout features is the spacious and inviting living area with brick flooring, original bluestone walls, and a dramatic wood-burning fireplace—perfect for cozy evenings or sophisticated entertaining. A gracious covered front porch offers a peaceful place to take in the natural landscape, while a deep soaking tub and light-filled meditation/yoga room provide quiet spaces for rest and renewal. In the 1920s and '30s, the home was owned by famed cartoonist John Striebel, creator of the Dixie Dugan comic strip. Over the years, its walls have echoed with the voices of Bob Dylan, Janis Joplin, Allen Ginsberg, George Harrison, and many other cultural legends. A true cornerstone of Woodstock's creative legacy, the estate was once owned by Albert Grossman, legendary music manager and founder of Bearsville Records and Studios. It was here, in 1965, that the iconic album cover for Bringing It All Back Home was photographed, capturing Bob Dylan and Sally Grossman in the home's elegant living room. Later, the home welcomed talents ranging from Johnny Cash and William Kennedy to Bjork and the Dave Matthews Band. Viking Hall, next door to the main house, offers an exceptional space designed to inspire. This stunning building features a bright and open studio area, ideal for artists, musicians, wellness practitioners, or remote work. With hand-hewn beams, loft space, French doors, and spa-like amenities—including a sauna, steam shower, and soaking tub—the space combines rustic elegance with modern comfort, perfect for creative retreats, workshops, or wellness sessions. Beyond Viking Hall, a private apartment with a stone fireplace, bedroom, and full bath once served as Albert Grossman's personal retreat, where he ran Bearsville Records. His legendary vinyl collection remains, and the lower level offers a gym area with ample storage. The estate includes the Farmhouse at Speare Road, a recently updated 4-bedroom, 2-bathroom residence. With its own private setting, this charming home is well-suited for guests, caretakers, or multi-generational living—offering flexibility for a variety of lifestyle needs. In the surrounding woods, discover a charming cabin complete with a bedroom, bathroom, and cozy kitchen. This private hideaway is ideal for long-term guests, studio rentals, or a secluded creative workspace. Both ready for a variety of uses, a spacious workshop building offers room for artistic or hands-on pursuits, while a classic barn adds rustic charm and versatile storage or studio space. Gardening enthusiasts will appreciate the sun-filled greenhouse, designed for year-round cultivation. A meditation gazebo—ideal for yoga, writing, or reflection in nature and an amphitheater complete with electricity, seating, and platform are among the estate's many distinctive features. Outdoor amenities include a heated, saline gunite pool, garden areas, spring-fed pond, seasonal mountain views, and woodland trails that offer total immersion in the natural beauty of the Catskills. This iconic Woodstock estate is two hours from NYC and in close proximity to the area's most beloved destinations. Whether inspired by its profound cultural roots or artisanal architecture, this property is a once-in-a-generation opportunity. This property is co-listed with Michelle Bergkamp, Corcoran Country Living.

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Location


Property Details


Parking

  • Description: Carport
  • Garage Spaces: 1
  • Spaces Total: 0

Bedroom Information

  • # of Bedrooms: 4

Bathroom Information

  • # of Baths (Full): 2
  • # of Baths (Partial): 2
  • # of Baths (Total): 4.0

Interior Features

  • # of Rooms: 12
  • # of Stories: 1
  • Basement: Yes
  • Basement Description: Full
  • Fireplace: Yes

Exterior Features

  • Exterior Walls Materials: Rock, Stone
  • Pool: Yes

Land Information

  • Land Use: Residential
  • Land Use Subtype: Rural/Agricultural

Lot Information

  • Parcel ID: 51580026.2104.110
  • Lot Size: 2564377 sqft

Property Information

  • Property Type: Single Family Residence
  • Style: Estate
  • Year Built: 1914

Tax Information

  • Annual Tax: $52,767

Utilities

  • Water & Sewer: Private, Well
  • Heating: Baseboard, Electric, Oil, Propane, Steam
  • Cooling: Ductless

Location

  • County: Ulster

Listing Details


Listed by:
Kathryn M. Johnson
William Pitt Sothebys Int Rlty
(917) 826-7050

Source:
OneKey MLS
MLS#: 849335
OneKey MLS

Investment Summary


Monthly Cash Flow
-$26,225
Cap Rate
-0.2%
Cash-on-Cash Return
-27.4%
Debt Coverage Ratio
-0.04
Internal Rate of Return (5 years)
-22.4%

Purchase Details

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Purchase price:
$4,999,000
Amount financed:
-$3,999,200
Down payment:
$999,800
Closing costs:
$149,970
Rehab costs:
$0
Initial cash invested:
$1,149,770
Square feet:
3,899
Cost per square foot:
$1,282
Monthly rent per square foot:
$1.28

Financing Details

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Loan amount:
$3,999,200
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
6.500%
Principal & interest:
$25,278
Property tax:
$4,397
Insurance:
$350
Private mortgage insurance (PMI):
$0
Monthly payment:
$30,025

Operating Income

Find a Property Manager

% Rent Monthly Yearly
Gross rent:
$5,000 $60,000
Vacancy loss: (6%)
6% -$300 -$3,600
Operating income:
$4,700 $56,400

Operating Expenses


% Rent Monthly Yearly
Property taxes: (88%)
88%-$4,397-$52,767
Insurance: (7%)
7%-$350-$4,200
Property management: (8%)
8%-$400-$4,800
Repairs & maintenance: (5%)
5%-$250-$3,000
Capital expenditures: (5%)
5%-$250-$3,000
HOA fees: (n/a)
n/an/an/a
Total operating expenses: (113%)
113%-$5,647-$67,767

Cash Flow


Monthly Yearly
Net operating income:
-$947 -$11,364
Mortgage payments:
-$25,278 -$303,336
Cash flow:
$26,225 $314,700