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Christine C. O'Shaughnessy
Licensed Real Estate Salesperson
(607) 287-0424 Cell
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43-45 Mill Hill Road, Woodstock, NY 12498

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Property Description

Some addresses simply exist within a town. Others become part of its identity. 43-45 Mill Hill Road, located in the heart of Woodstock, presents a rare opportunity to own a piece of one of the Hudson Valleys most iconic and enduring destinations. Positioned along one of the villages most visible commercial corridors, the property sits at the center of the energy that has drawn generations to Woodstock. Artists, musicians, makers, restaurateurs, weekenders and longtime residents have shaped a community known far beyond the Catskills, creating a year-round destination where independent businesses, food, art and creative culture continue to thrive. Positioned on .37 acres, the property comprises two distinct commercial buildings, currently home to The Penny Cafe & Tavern. Each offers its own character and function, together creating a versatile commercial footprint in the heart of the village. The Tavern occupies the propertys charming single-story building, where a covered deck extends the space outdoors and creates an inviting setting for dining, gathering and entertaining. Surrounded by established landscaping, the building has an intimate character that feels naturally at home within Woodstocks village landscape. The neighboring two-story building is home to The Penny Cafe on its first floor. Above, a separate entrance provides independent access to the second level, which features a prep kitchen and a powder room, adding another layer of flexibility to the property and its existing commercial use. Together, the two buildings create something more distinctive than a conventional commercial offering, with multiple spaces, indoor and outdoor experiences, and an established presence along one of Woodstocks primary commercial thoroughfares. Beyond the buildings themselves, the significance of this offering is its location. Hamlet Commercial zoning places the property within Woodstocks established commercial district, surrounded by the restaurants, shops, galleries and gathering places that make the village one of the Hudson Valleys most recognizable destinations. Its prominent position along Mill Hill Road provides the kind of visibility and connection to the village that simply cannot be recreated. The property is offered with an existing triple-net lease, presenting an opportunity to acquire an established income-producing asset in an exceptionally limited market. Under the current lease structure, the tenant is responsible for utilities, taxes, insurance, management, exterior maintenance, and grounds care. More than a commercial investment, 43-45 Mill Hill Road represents an opportunity to hold a lasting presence in a place whose influence extends far beyond the Catskills. Commercial properties in the heart of Woodstock are inherently finite, and offerings combining visibility, character, multiple structures, outdoor space, and an established tenant are particularly rare. This is not simply an opportunity to acquire commercial real estate. It is an opportunity to own a piece of Woodstock.

43-45 Mill Hill Road | MLS# 20265315

This commercial property located at 43-45 Mill Hill Road, Woodstock, NY 12498 is currently listed for sale with an asking price of $4,000,000. Search Woodstock real estate on christine-oshaughnessy.timberlandproperties.com today.

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Property Features

Property Type: Commercial - Business
Basement: Yes
Cooling: Ductless, Electric
Lot Size: 0.37 Acres
Roof Type: Asphalt, Metal, Shingle, Wood
Taxes: $14,189
Year Built: 1972

Amenities

Awning(s)
Fire Pit
Garden
Lighting
Storage

Feature Descriptions

Business Type: Restaurant
Days on Site: 5
Exterior: Wood Siding
Flooring: Hardwood
Lot: Garden, Gentle Sloping, Landscaped
Parcel #: 27.55-1-40
Road Frontage: Town
Sewer: Public Sewer
SQFT Total: 1742
Tenant Pays: All Utilities, Exterior Maintenance, Insurance, Management, Taxes, See Remarks
Water: Public

Demographics

Listed By / Shown By

Listing By

Agency Name: Corcoran Country Living

Shown By

Agent Name: Christine C. O'Shaughnessy
Agent Phone: (607) 287-0424 Cell
Agency Title: Timberland Properties

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All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 09/17/2026. The listing information on this page last changed on 09/17/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 09/17/2026 12:00:03 AM EST) or Global MLS (last updated Wed 09/16/2026 11:52:32 PM EST) or New York State Alliance MLS (last updated Wed 09/16/2026 11:59:05 PM EST) or Hudson Valley Catskill Region MLS (last updated Wed 09/16/2026 11:51:19 PM EST) or OneKey MLS (last updated Wed 09/16/2026 11:53:26 PM EST). Real estate listings held by brokerage firms other than Timberland Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless.

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