9 Black Bear Road, Bearsville, NY 12409

$2,250,000

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… Read More 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. Read Less

Listing Courtesy of Corcoran Country Living.

Listing Snapshot

Days Online

Last Updated

Apr 15, 2026

Property Type

Single Family Residence

Beds

Full Baths

Square Ft.

3,539

Year Built

1960

Property Tax

$17,475

MLS Number

955449

Additional Details

Appliances & Equipment

Description: "Dishwasher", "Dryer", "Exhaust Fan", "Gas Range", "Microwave", "Refrigerator", "Tankless Water Heater", "Washer", "Water Purifier Owned"

Basement

Description: "Partially Finished"

Building

Area: 3539, Architecture: "Cape Cod", Construction Materials: "Other", Year Built: 1960

Cooling

Details: "Central Air"

Exterior Features

Patio Features: "Deck", "Patio", "Terrace"

Fence

Description: "Wood"

Fireplaces

Total Fireplaces: 1

Floors

Flooring: "Hardwood"

Heating

Heating: "Forced Air", "Propane"

Laundry

Description: "Laundry Room"

Lot

Acres: 4.14

Property

Description: "Fuel Tank(s)", "Generator"

Pool

Features: "Outdoor Pool", "Salt Water", Private Pool

Utilities

Sewer: "Septic Tank", Water Source: "Well", Utilities: "Electricity Connected", "Sewer Connected", "Water Connected"

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