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$975,000 Just Listed

  • For Sale
  • Active
  • Commercial Service
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Iconic Berkshire County Property for Sale Formerly 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.

Full Property Details for 100 Fenn St

General

  • Price: $975,000
  • Taxes: $13,202 (2025)
  • Status: Active
  • Type: Commercial Service
  • Source: 1109
  • MLS ID: 251061
  • Updated: 10/7/2026
  • Added to Site: 5 day(s) ago

Business

  • Business Type: Restaurant, Retail, Professional/Office

Interior

  • Interior Features: Air Cond

Parking

  • Parking Features: On-Street

Location

  • Area: Middle Registry

Heating & Cooling

  • Heating Type: Nat Gas, Forced Air, Hot Water

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Foundation: Slab
  • Roof: Asphalt
  • Square Feet: 12,786
  • Year Built: 1900
  • Year Built Source: Assessor

Lot Features

  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,405
  • Zoning: Business

Financial Considerations

  • Tax Amount: $13,202
  • Tax Year: 2025

Disclosures and Reports

  • Property ID: PITT M:H09 B:0008 L:004

Listed by Lamacchia Realty, Inc. - Dalton, Jim Thurston and Lamacchia Realty, Inc. - Dalton, Christopher Moon

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Listing agents

— 100 Fenn St —

  • Jim Thurston

    Lamacchia Realty, Inc. - Dalton

  • Christopher Moon

    Lamacchia Realty, Inc. - Dalton

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 100 Fenn St

School District:Pittsfield School District, Pittsfield, MA
NameGradesDistance
Morningside Community School
100 Burbank Street, Pittsfield, MA 01201
PK-50.6 mi
Theodore Herberg Middle School
501 Pomeroy Avenue, Pittsfield, MA 01201
6-81.2 mi
Pittsfield High School, Pittsfield, MA
300 East Street, Pittsfield, MA 01201
9-120.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 100 Fenn St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/05/2026
Listed
$975,000
473.53%
MLS
8/03/1992
Sold
$170,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 100 Fenn St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$13,202
3%
$347,800
7%
2024
$12,838
1%
$324,100
—
2023
$12,708
8%
$324,100
10%
2022
$11,774
—
$295,100
—
2021
$11,801
-1%
$295,100
—
2020
$11,910
1%
$295,100
—
2019
$11,786
—
$295,100
—
2018
$11,798
1%
$295,100
—
2017
$11,739
5%
$295,100
—
2016
$11,232
4%
$295,100
—
2015
$10,810
4%
$295,100
—
2014
$10,379
—
$295,100
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 100 Fenn St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Lamacchia Realty, Inc. - Dalton, Jim Thurston and Lamacchia Realty, Inc. - Dalton, Christopher Moon

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100 Fenn St, Pittsfield, MA 01201 (MLS# 251061) is a Commercial Service property. 100 Fenn St is currently listed for $975,000 and was received on October 05, 2026. Want to learn more about 100 Fenn St? Do you have questions about finding other Commercial Service real estate for sale in Pittsfield? You can browse all Pittsfield real estate or contact a Coldwell Banker agent to request more information.

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