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158 Skyline Trl, Middlefield MA 01243

$269,900

Estimated $2,107/month Calculator

Single Family

3 Bedrooms

Baths

3576

Total Parking: 4

43,560 (1.00)

Built in 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.

This home has been viewed 2 times

Last Checked: September 17th, 2026 at 5:48am (Source: MLS PIN #73567550)

Air Conditioning

Lead Paint Free

General Information for 158 Skyline Trl, Middlefield MA 01243

Listing ID73567550

Property TypeSingle Family / Detached

Price$269,900 ($75.48/SqFt)

StyleColonial

CityMiddlefield

CountyHampshire

Neighborhood(s)

Garage Parking0

ZoningR1

Year Built1837

Year Built SourcePublic Records

Year Built DetailsActual

Interior Features for 158 Skyline Trl, Middlefield MA 01243

Approximate Living Area Total3576

Living Area Includes BasementNo

Rooms8

Bedrooms3

Primary En Suite BathroomYes

BasementFull

CoolingSplit

Fireplaces

AppliancesRange

Flooring

Electric220 Volts

Exterior Features for 158 Skyline Trl, Middlefield MA 01243

Approximate Lot Size (Acres)1

Approximate Lot Size (Square Feet)43560

Total Parking4

Garage Parking0

WaterShared Well

SewerPrivate Sewer

Lot FeaturesGentle Sloping

Parking Features1

Exterior FeaturesPorch

Foundation Materials

Construction MaterialsFrame

Road Frontage Type

Patio & PorchCovered

Roof MaterialAsphalt/fiberglass Shingles

Utility Connections110 Volts

Water Views

Water Views Features

Waterfront0

Waterfront Features

Pool Features

Horse Permitted0

Horse Amenities

Disclosures for 158 Skyline Trl, Middlefield MA 01243

Lead PaintNone

UFFI

Living Area Includes BasementNo

Living Area Disclosure

Building Area SourcePublic Records

Special Listing Conditions

ExclusionsExcluded: Washer And Dryer Excluded.

Title 5A

Compensation Based On

Financial Information for 158 Skyline Trl, Middlefield MA 01243

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax5326

Tax Year2025

Assessed Value$292,000

Location Information for 158 Skyline Trl, Middlefield MA 01243

Elementary SchoolChester Elementary/Littleville

Middle SchoolGateway Regional School

High SchoolGateway Regional School

Neighborhood(s)

Area AmenitiesWalk/jog Trails

Contact Information for 158 Skyline Trl, Middlefield MA 01243

Agent

Name: Dennis LeClair

Office

Name: RE/MAX Compass

Phone: 413-568-0040

Payment Calculator

, Interest

Property Taxes 443.83

Principal & Interest 1663.04

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

RE/MAX Compass

Dennis LeClair

Agent Phone

Office Phone

(413) 568-0040

Text Agent Call Agent Call Office

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EXIT

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