100 Fenn St

About this home

Iconic Berkshire County Property for Sale. Former home to the renowned Highland Restaurant, this landmark property presents a rare opportunity in the heart of downtown Pittsfield. Located at 100 Fenn Street and adjacent to City Hall, the building is situated within the City of Pittsfield's Downtown Creative District and Housing Development Incentive Program (HDIP) Overlay. With a distinguished history as a longtime gathering place for the community, this prominent property offers exceptional potential for restaurant, hospitality, retail, residential, or mixed-use redevelopment. Opportunities of this caliber are rarely available in Berkshire County.

Listing last checked: November 6, 2026 at 6:36 PM ESTListing updated: November 5, 2026 at 7:04 PM EST

Listed by Christopher Moon · Lamacchia Realty, Inc. · MLS #73599523

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Details at a glance

Interior1 property facts

Basement: Not reported

Building2 property facts

Style: Other
Year built: 1900

Land & utilities3 property facts

Lot size: 0.17 acres
Pool: Not reported
Zoning: DCD

Financial2 property facts

Annual taxes: $13,424
Assessment year: 2026

Location

Estimated monthly cost

Explore costs at the $975,000 asking price. Adjust the assumptions to your situation.

Known monthly costs$6,049 / monthAdjust

Down payment (%)Interest rate (%)Loan termMonthly property tax ($)Monthly insurance ($)Monthly HOA ($)

Principal & interest: $4,930
Property tax: $1,119
Insurance: Not entered
HOA: Not entered

Listing annual taxes: $13,424. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

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About 100 Fenn St

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Request a tour of 100 Fenn St and a Bean Group agent will help coordinate an available time with the listing side.

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Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

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Bean Group · eXp Realty

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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