• UNDER CONTRACT

9 Black Bear Road

Bearsville, NY 12409

  • $2,250,000
  • 4 Beds
  • 3 Baths
  • 3,539 Sqft
  • 4.14 Acres
  • 1960 Built

Tucked just beyond the heart of Woodstock, down a private road off a quiet dead-end street, this completely renovated home feels like a secret you're lucky to have discovered. Just 2.5 miles from town and moments from the Bearsville Theatre, the setting is both deeply private and wonderfully connected. While the exterior presents a discreet, understated presence, the interior unfolds into a surprisingly expansive, multi-level layout that lives far larger than it appears. Expansive mountain views enhance the home's calm, elevated retreat-like setting, yet you remain close to all the energy and culture Woodstock has to offer. Inside, the home opens easily into a bright main level with an open, flowing plan anchored by a beautifully designed cook's kitchen with a generous island, hardwood floors, and seamless connections to the living and dining spaces. Two steps down, the bluestone-clad dining room, wrapped in windows, opens directly to a multi-level bluestone patio, ideal for al fresco meals overlooking the pool and mountains beyond. Beamed ceilings and a fireplace bring warmth and presence to the living room, which opens to a deck offering another elevated view. An office, a large bedroom, and a full bath complete this level. Upstairs, two vaulted-ceiling bedrooms with oversized picture windows create peaceful, light-filled retreats. Generous room proportions and thoughtful separation of spaces throughout the home create a sense of volume and ease that allows it to live comfortably and flexibly. The garden level offers a spacious, highly adaptable layout with its own bedroom and private en suite bathroom, as well as a separate entrance, making it ideal for a relative, guest, or long-term visitor. This level also includes additional space for laundry, storage, or a home gym. With usable living space across three distinct levels, the home offers exceptional flexibility for a variety of needs. Outside, the property truly shines. A flat, landscaped yard leads to a heated saltwater pool set in bluestone and framed by wood fencing and mature trees for privacy. Nearby, a natural clearing among the trees offers an ideal setting for a future firepit, and a separate 24x24 insulated studio extends the property's usefulness for creative work, hobbies, or quiet focus. The renovation goes far beyond the surface, with major systems, mechanics, fixtures, and finishes extensively updated throughout, including a whole-house backup generator and new pool mechanics. Deceptively spacious and thoughtfully laid out, this is a home where every room has a view and every space feels purposeful. Whether enjoyed year-round or as a weekend escape, it is a rare blend of sanctuary, style, and location, quietly extraordinary from the moment you arrive.

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Property Highlights
  • ELEMENTARY : Woodstock
  • MID. SCHOOL : Onteora Middle School
  • HIGH SCHOOL : Onteora High School
  • VIEW : Mountain(s), Trees/Woods
  • PRICE/SQFT : $636
  • DAYS ON MARKET : 38
  • MLS : 955449

Additional Information

ADDITIONAL INFORMATION
  • BASEMENT DESCRIPTION: Partially Finished
  • DAYS ON MARKET: 38
  • ELEMENTARY SCHOOL: Woodstock Elementary School
  • ELEMENTARY SCHOOL DISTRICT: Onteora
  • HIGH SCHOOL: Onteora High School
  • LIVING AREA SQFT: 3539
  • MIDDLE SCHOOL: Onteora Middle School
  • ON MARKET DATE: 2026-04-18
  • PARKING: Off Street
  • ROAD TYPE: Private Road
  • SEWER: Septic Tank
  • STYLE: Cape Cod
  • TAX AMOUNT: $17,474
  • TYPE: Residential
  • UTILITIES: Electricity Connected, Sewer Connected, Water Connected
  • VIEW: Mountain(s), Trees/Woods
  • YEAR BUILT: 1960
INTERIOR/EXTERIOR FEATURES
  • APPLIANCES INCLUDED: Dishwasher, Dryer, Exhaust Fan, Gas Range, Microwave, Refrigerator, Tankless Water Heater, Washer, Water Purifier Owned
  • BEDS: 4
  • CONSTRUCTION MATERIALS: Other
  • COOLING: Central Air
  • EXTERIOR FEATURES: Deck, Patio, Terrace, Pool (Outdoor Pool, Salt Water, Private)
  • FLOORING: Hardwood
  • FULL BATHS: 3
  • HEAT: Forced Air, Propane
  • INTERIOR FEATURES: Cathedral Ceiling(s), Eat-in Kitchen
  • ROOMS: 9

Listing Courtesy of Alexis Li of Corcoran Country Living (845.876.6676).

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Location for 9 Black Bear Road, Bearsville, NY

Schools for 9 Black Bear Road, Bearsville, NY

Our community offers residents access to a number of fine private and public schools for all grade levels. Please read below for information on each of the schools in our area.

Private Schools
SCHOOL LOCATION GRADE
Zena Democratic School 84 Zena Road Kingston, NY 12401 UG
GreatSchools

*UG = ungraded.
Detailed school information provided by GreatSchools.org © . All rights reserved.

Public and private school information is provided by sources including GreatSchools.org and various MLS services including the One Key, SMARTMLS, NCMLS, DARMLS and Greenwich MLS, and is subject to the terms of use on those sites. William Pitt and Julia B. Fee Sotheby’s International Realty believes the information provided by these sources to be accurate but will not be held responsible if any data as well as information such as school districts for listings is inaccurate.

Community

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Hudson Valley

, New York

Amid the picturesque landscapes of New York State, the Hudson Valley captivates with its natural beauty and historic charm. This region, just north of New York City, is renowned for its picturesque river...

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  • Julia B. Fee Sotheby's International Realty