158 Skyline Trail

Hampshire County MA 01243

3576 sq. ft.

43560 sq. ft.

Single-Family

Last sold for $275,000

Dennis LeClair, last sold this property on 29 October 2026 after 65 days on market.

Overview

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.

Features

3 bedrooms

3 bathrooms

4 carspaces

4 open car spaces

1 garage space

3576 sq. ft. floor area

43560 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Hampshire County over the last 12 months, the estimated median property value of 158 Skyline Trail is $320k.

Median value

$320k

Estimated value range

$275k - $435k

Median days on market

Estimated value trend

-22%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Hampshire County. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 158 Skyline Trail

2026

Sold

$275,000

29 Oct 2026 by Dennis LeClair, of REMAX Compass | Westfield

2007

Sold

$140,000

12 Jan 2007 by Daniel Suriner, of Wolcott Realty

Happy sellers in Hampshire County

We have insufficient information to provide an overview of customer satisfaction for Hampshire County. Viewing the agent profiles, reviews and sales for Hampshire County can provide insights for this location.