LevelSecond
158 Skyline Trl, Middlefield MA 01243
Middlefield, MA 01243
$269,900
Est. $2,009/month
Track this home for price, status, and open-house alerts.
About this home
Attention investors, cash buyers, and those ready to bring their vision to life—this charming 1837 Colonial-style farmhouse offers a unique opportunity in the heart of beautiful Middlefield. With approximately 3,576 square feet of bright, sun-filled living space, the home features generously sized rooms, a flexible floor plan, up to 5+ possible bedrooms, and 3 full bathrooms. The attached red carriage barn/workshop adds valuable versatility, providing ample space for hobbies, storage, a workshop, or creative pursuits. Set on a full acre, the property features mature landscaping, pear trees, blueberry bushes, and a spacious lawn that creates a peaceful country retreat.Enjoy the best of small-town living with the Middlefield Fairgrounds just a short walk away, plus easy access to area trails for hiking, snow sports, and exploring the outdoors. For those seeking recreational or investment potential, this Berkshire location is ideally situated near Jacob’s Pillow Dance Festival, Otis Reservoir, Otis Ridge Ski Area, Butternut, Stockbridge, Northampton, Pittsfield, Lee, Lenox, and many other popular cultural and recreational destinations.With its character, generous living space, acreage, carriage barn, and desirable Berkshire location, this property offers exciting possibilities as a primary residence, vacation getaway, or investment property, including potential Airbnb/vacation rental use. Property is being sold as-is. Buyers are responsible for their own due diligence. Shared well serves 6 homes and has a semi-annual water system maintenance fee of $168.
View in the App
Save this property, schedule tours instantly, and get alerts when the price drops
Scan with phone
Public Records & Permits
Log in to view assessor & tax records, ownership history, and recent building permits for this property.
BMN Estimate
Get the number an algorithm can't give you
A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.
Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Aug 24, 2026
$269,900
Original listing
Agent: Dennis LeClair
Office: RE/MAX Compass
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/24/2026 | 🏠 Listed for Sale | $269,900 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $5,326 | $292,000 |
Financial Details
Annual Property Tax
$5,326
Tax Year 2025
Assessed Value
$292,000
Facts & Features
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1837
Living Area
3,576 sq ft
Lot Size
1.00 acres
Bedrooms
3
Full Baths
3
Total Rooms
8
Interior
Heating
Forced Air, Electric Baseboard, Oil, Electric, Wood
Cooling
None
Flooring
None
Appliances
Electric Water Heater, Refrigerator, Washer
Fireplace
None
Basement
Full, Crawl Space, Sump Pump, Dirt Floor, Concrete
Laundry
In Basement, Washer Hookup
Features
None
Exterior
Construction
Frame, Brick, Stone
Architecture
Colonial, Farmhouse
Roof
Shingle
Features
Porch, Rain Gutters, Barn/stable
Pool
None
Spa
None
Fencing
Fenced/enclosed
Patio/Porch
Porch
Parking
Has Garage
Yes
Features
Storage, Workshop In Garage, Barn, Off Street
Total Spaces
4
Utilities
Electric
Circuit Breakers
Water
Shared Well
Sewer
Private Sewer
Gas
None
Other
Washer Hookup
Financial
Annual Tax
$5,326
Assessed Value
$292,000
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
Down Payment Resource
Eligible
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
Shared Well-6 Houses $168 Semiannually For System Maintenance, 2nd Floor Electric Baseboard Heat & Upstairs 3rd Bathrooms Are Not Functional. Kitchen Does Not Have A Stove.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
House Color
White
Sq Ft Source
Public Record
Documents
None
County
Hampshire
Total market time (incl. prior listings)
1 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1837
Bedrooms
3
Full Bathrooms
3
Living Area
3,576 sq ft
Total Rooms
8
Floor Layout
Interactive room guide
Floor Layout
Finished Area
3,576 sq ft above grade
LevelSecond
LevelSecond
LevelSecond
LevelSecond
LevelSecond
LevelSecond
LevelFirst
Display Options
Outdoor Areas
Patio & porchPorch
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Appliances:
Electric Water Heater, Refrigerator, Washer
Interior Features:
Windows:
Basement:
Full, Crawl Space, Sump Pump, Dirt Floor, Concrete
Laundry:
In Basement, Washer Hookup
Security:
Construction & Materials
Style:
Colonial, Farmhouse
Year Built:
1837
Structure Type:
Exterior Materials:
Frame, Brick, Stone
Roof:
Shingle
Foundation:
Stone, Brick/Mortar
Heating, Cooling & Utilities
Heating:
Forced Air, Electric Baseboard, Oil, Electric, Wood
Cooling:
None
Hot Water:
Water Source:
Shared Well
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Porch, Rain Gutters, Barn/Stable
Patio & Porch:
Porch
Fencing:
Fenced/Enclosed
Other Structures:
Barn/Stable
Lot Features:
Level
Road Surface:
Parking & Garage
Total Parking Spaces:
4
Parking Features:
Storage, Workshop in Garage, Barn, Off Street
Nearby Schools
School District
Gateway School District local
Where Graduates Go
Class of 2021
61%
attend college
41%
4-Year
20%
2-Year
11%
Out of State
0%
Working
School Safety
2024-25
4.2%
Above Average
4.2%
Suspensions
3.3%
In-School
1.3% below state avg
Elementary Schools
2 schools
C
Becket Washington School
3.7 mi
|
#631 of 824
|
Score: 39.2
Dropped 543 spots from last year
-19 below state avg
91 students
Less Diverse
Grades PK-05
B-
Chester Elementary School
3.9 mi
|
#498 of 824
|
Score: 44.7
Dropped 463 spots from last year
-13.5 below state avg
114 students
Less Diverse
Grades PK-05
Learn about these ratings
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$444
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
Loading map...
Neighborhood
158 Skyline Trl, Middlefield MA 01243
Middlefield, MA 01243
Listing Information
Listing Agent
Dennis LeClair
Listing Office
RE/MAX Compass
Office Phone
413-568-0040
Agent MLS ID
CT007448
Office MLS ID
AN1149
Listing Data Updated
Aug 25, 2026 3:30 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
Contact Us
Ask about this property — free, no obligation.
Similar Homes for Sale
Comparable Properties
Customize Comparable Search
Finding comparable properties...
Loading market insights for Middlefield.