100 Fenn St, Pittsfield MA 01201
Pittsfield, MA 01201 • West Pittsfield
$975,000
Est. $6,249/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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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.
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Price & Status History
Property Timeline
Listed for Sale
Nov 6, 2026
$975,000
Original listing
Office: Lamacchia Realty, Inc.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 11/06/2026 | 🏠 Listed for Sale | $975,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $13,424 | — |
Financial Details
Annual Property Tax
$13,424
Tax Year 2026
Facts & Features
Home Facts
Type
Commercial Sale
Year Built
1900
Living Area
13,414 sq ft
Lot Size
0.17 acres
Interior
Heating
None
Cooling
None
Flooring
None
Appliances
None
Fireplace
None
Basement
None
Laundry
None
Features
None
Exterior
Construction
None
Architecture
None
Roof
None
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Features
None
Utilities
Electric
None
Water
None
Sewer
None
Gas
None
Other
Public Water, Public Sewer, Natural Gas Available
Financial
Annual Tax
$13,424
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Documents
None
County
Berkshire
Property Overview
Listing Type
For Sale
Year Built
1900
Living Area
13,414 sq ft
Floor Layout
Interior Features
Flooring:
Appliances:
Interior Features:
Windows:
Basement:
Laundry:
Security:
Construction & Materials
Year Built:
1900
Structure Type:
Exterior Materials:
Roof:
Foundation:
Utilities & Systems
Heating:
Cooling:
Hot Water:
Water Source:
Sewer:
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Road Surface:
Parking & Garage
Parking Features:
Nearby Schools
School District
Pittsfield School District local
C-
Where Graduates Go
Class of 2021
54%
attend college
32%
4-Year
22%
2-Year
16%
Out of State
2%
Working
School Safety
2024-25
9.6%
Above Average
7.9%
Suspensions
9.8%
In-School
1.7%
Emergency
4.1% above state avg
Elementary Schools
10 schools
Hillcrest Educational Centers School
2.3 mi
Grades K-12
D
Morningside Community School
0.6 mi
|
#749 of 825
|
Score: 32.6
Improved 24 spots from last year
-25.6 below state avg
374 students
Very Diverse
Rising School
Diverse Student Body
Grades PK-05
F
Silvio O Conte Community School
1.0 mi
|
#802 of 825
|
Score: 28.1
Improved 13 spots from last year
-30.1 below state avg
380 students
Very Diverse
Diverse Student Body
Grades PK-05
D
Crosby School
1.1 mi
|
#763 of 825
|
Score: 31.4
Dropped 16 spots from last year
-26.8 below state avg
245 students
Very Diverse
Diverse Student Body
Grades PK-05
Crosby Educational Academy
1.1 mi
19 students
Diverse
Grades K-05
A-
Egremont School
1.4 mi
|
#215 of 825
|
Score: 53.9
Improved 168 spots from last year
-4.3 below state avg
382 students
Diverse
Rising School
Diverse Student Body
Grades PK-05
B-
Allendale School
1.7 mi
|
#497 of 825
|
Score: 44.9
Improved 35 spots from last year
-13.4 below state avg
226 students
Diverse
Rising School
Diverse Student Body
Grades PK-05
C
Robert T. Capeless Elementary School
2.2 mi
|
#642 of 825
|
Score: 38.6
Dropped 313 spots from last year
-19.6 below state avg
182 students
Diverse
Grades PK-05
B-
Williams School
2.4 mi
|
#453 of 825
|
Score: 46.0
Dropped 415 spots from last year
-12.2 below state avg
235 students
Diverse
Grades PK-05
C
Stearns School
2.6 mi
|
#602 of 825
|
Score: 40.7
Improved 33 spots from last year
-17.6 below state avg
191 students
Diverse
Rising School
Grades PK-05
Middle Schools
2 schools
C-
Theodore Herberg Middle School
1.1 mi
|
#298 of 352
|
Score: 31.8
Improved 16 spots from last year
-26.4 below state avg
558 students
Diverse
Diverse Student Body
Grades 06-08
F
John T Reid Middle School
1.2 mi
|
#343 of 352
|
Score: 25.1
Improved 11 spots from last year
-33.1 below state avg
382 students
Diverse
Diverse Student Body
Grades 06-08
High Schools
6 schools
Eagle Education Academy
0.1 mi
20 students
Diverse
Diverse Student Body
Grades 06-12
Brookside School
2.3 mi
Grades 06-12
High Point School
2.3 mi
Grades 07-12
B-
Pittsfield High School
0.3 mi
|
#201 of 346
|
Score: 52.2
Improved 56 spots from last year
-6 below state avg
699 students
Diverse
19 sports
• 856 athletes
Rising School
Strong Athletics
Diverse Student Body
Grades 09-12
C-
Taconic High School
1.3 mi
|
#298 of 346
|
Score: 39.1
Improved 19 spots from last year
-19.1 below state avg
789 students
Diverse
19 sports
• 784 athletes
Career Tech Programs
Strong Athletics
Diverse Student Body
Grades 09-12
Miss Hall's School
1.7 mi
Grades 09-12
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Over life of loan
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Including down payment
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Down: $0
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Monthly Payment Breakdown
Principal & Interest
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Property Tax
$1,119
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
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Rate Impact
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location
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Neighborhood
West Pittsfield
100 Fenn St, Pittsfield MA 01201
Pittsfield, MA 01201
Listing Information
Listing Agent
Christopher Moon
Listing Office
Lamacchia Realty, Inc.
Office Phone
413-443-7274
Agent MLS ID
CN263692
Office MLS ID
AN8599
Listing Data Updated
Nov 5, 2026 7:04 PM EST
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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