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Bean Group
Offered at $269,900Pending
beds
3
baths
3
sq ft
3,576
Built
1837

158 Skyline Trl

Middlefield, MA 01243

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.

Listing last checked: Listing updated:

Listed by Dennis Leclair · RE/MAX Compass · MLS #73567550

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Details at a glance

Interior4 property facts
Rooms
8
Heating
Forced Air, Electric Baseboard, Oil, Electric, Wood
Cooling
None
Basement
Yes · Full, Crawl Space, Sump Pump, Dirt Floor, Concrete
Building5 property facts
Style
Single Family Residence
Year built
1837
Parking
4
Foundation
Stone, Brick/Mortar
Roof
Shingle
Land & utilities5 property facts
Lot size
1 acres
Water
Shared Well
Sewer
Private Sewer
Pool
Not reported
Zoning
R1
Financial2 property facts
Annual taxes
$5,326
Assessment year
2025

Location

Estimated monthly cost

Explore costs at the $269,900 asking price. Adjust the assumptions to your situation.

Known monthly costs$1,809 / monthAdjust
Principal & interest
$1,365
Property tax
$444
Insurance
Not entered
HOA
Not entered

Listing annual taxes: $5,326. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

More property insights

Automated value estimate $281,227

Estimated range $256,524–$305,930.

Automated estimates are not appraisals or guarantees of market value.

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Photo-based condition insights

Overall presentation: average

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About 158 Skyline Trl

Can I request a private showing?

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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Availability varies by property and source. Request the documents you need and we will help obtain what is available.