Active Under Contract
158 Skyline Trl
Middlefield, MA 01243
Residential · Active Under Contract · MLS #73567550
Listing Courtesy of RE/MAX Compass | Dennis Leclair
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MLS PIN data
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.
Property information
Details at a glance
Interior
- Rooms
- 8
- Heating
- Forced Air, Electric Baseboard, Oil, Electric, Wood
- Cooling
- None
Building
- Style
- Single Family Residence
- Year built
- 1837
- Parking
- 4
- Foundation
- Stone, Brick/Mortar
- Roof
- Shingle
Land & utilities
- Lot size
- 1 acres
- Water
- Shared Well
- Sewer
- Private Sewer
- Zoning
- R1
Financial
- Annual taxes
- $5,326
- Assessment year
- 2025
Listing history
Price and status timeline
No additional public listing history was supplied for this property.
Property value estimate
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Comparable sales
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Recent comparable sales are not available for this property.
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Local market context
How this home compares in Middlefield
Active city listing statistics from MLS PIN as of September 5, 2026. Asking prices are not completed-sale values.
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Common questions
About 158 Skyline Trl
Can I schedule a private showing?
Yes. Request a tour of 158 Skyline Trl and a Bean Group agent will help coordinate an available time with the listing side.
Can you help me evaluate this property?
Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
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