Active Under Contract
16 Days on market
158 Skyline Trl Middlefield — Photo 1 of 40

158 Skyline Trl Middlefield — Photo 1 of 40

$269,900

158 Skyline Trl, Middlefield, MA 01243

Middlefield, MA 01243

Beds

3

Baths

3

SqFt

3,576

Style

Single Family

Built

1837

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.

Market Value Analysis

Not enough listings in Middlefield for a city-only view.
This Property$75/sqft
Nearby Avg (5 mi)$214/sqft
65% BelowMarket Average

* Analysis is based on 2 actively listed and recently sold comparable properties within ~5 miles of this property.

Property Details

Financials

Original Price$269,900
Annual Taxes$5,326

Parking

Garage0
Off-Street4

Interior Specifications

Total Rooms8
FireplacesNone
Flooring--
BasementFull, Crawl Space, Sump Pump, Dirt Floor, Concrete

Climate & Utilities

HeatingForced Air, Electric Baseboard, Oil, Electric, Wood
CoolingNone
WaterShared Well
SewerPrivate Sewer

Building & Exterior

ConstructionFrame, Brick, Stone
RoofShingle
FoundationStone, Brick/Mortar
ZoningR1

Property & Lot

Acres1
SqFt Lot43,560
Lot FeaturesLevel

Amenities & Appliances

Electric Water Heater • Refrigerator • Washer

Neighborhood

Walk/Jog Trails • Bike Path • Public School

Geography

Floorplan Breakdown

Structural Layout

Second
Master BedroomBedroom 2Bedroom 3Bedroom 4Bedroom 5Bathroom 2Bathroom 3
First
Bathroom 1
Master Bedroom
Lvl Second
Bedroom 2
Lvl Second
Bedroom 3
Lvl Second
Bedroom 4
Lvl Second
Bedroom 5
Lvl Second
Bathroom 1
Lvl First
Bathroom 2
Lvl Second
Bathroom 3
Lvl Second

Population

173

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$91K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

2.6%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Hampshire County

384 housing units permitted in the last 12 months (+45% vs the prior 12 months) — 272 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,576 sq ft principal dwelling). Lot size: 43,560 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Listing Provided By

Listing Agent: Dennis Leclair

Listing Office: RE/MAX Compass

MLS® Number: 73567550

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