18 Striebel Road, Woodstock

$4,999,000

4 Beds
3 Baths
3,899 Sqft
71.69 Acres
0 Garage

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 Kathryn Johnson, William Pitt Sotheby's International Realty.

Essential Information
MLS® #20251208
Price$4,999,000
Bedrooms4
Bathrooms3.00
Full Baths2
Half Baths2
Square Footage3,899
Acres71.69
Year Built1914
TypeResidential
Sub-TypeSingle Family Residence
StatusActive
Community Information
Address18 Striebel Road
AreaWoodstock
CityWoodstock
CountyUlster
StateNY
Zip Code12498
Amenities
Has PoolYes
Parking

Circular Driveway, Drive Through, Gravel, Driveway, Carport

View

Forest, Pond, Pool, Trees/Woods

Pool

Fenced, Gas Heat, Gunite, Heated, In Ground, Outdoor Pool, Pool Cover, Salt Water, See Remarks

Interior
CoolingDuctless, Multi Units, Zoned
FireplaceYes
# of Fireplaces3
StoriesTwo
Interior Features

Bookcases, Built-in Features, Cathedral Ceiling(s), Cedar Closet(s), Chandelier, Crown Molding, Eat-in Kitchen, Entrance Foyer, High Ceilings, High Speed Internet, Natural Woodwork, Pantry, Sauna, Smart Thermostat, Soaking Tub, See Remarks

Appliances

Water Purifier, Washer, Tankless Water Heater, Refrigerator, Range Hood, Gas Range, Gas Oven, Freezer, Exhaust Fan, ENERGY STAR Qualified Appliances, Electric Water Heater, Dryer

Heating

Electric, Fireplace(s), Oil, Propane, Steam, Zoned

Fireplaces

Bedroom, Dining Room, Library, Living Room, Wood Burning

Exterior
ExteriorCedar, Stone, See Remarks
RoofAsphalt, Metal, Shake
ConstructionCedar, Stone, See Remarks
FoundationStone
Exterior Features

Balcony, Courtyard, Garden, Lighting, Playground, Private Entrance, Private Yard, Storage

Lot Description

Pond on Lot, Back Yard, Front Yard, Garden, Gentle Sloping, Private, Secluded, Views, Wooded, See Remarks

School Information
DistrictOnteora Central
Additional Information
ZoningR3
Listing Details
AgentMichelle Bergkamp
Listing Courtesy of Corcoran Country Living
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