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Darren McGovern
REALTOR®
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158 Skyline Trl, Middlefield, MA 01243

$269,900
  • Main Photo

40 Photos

Active Under Contract
BEDS3 BATHS3 full SQUARE FEET3,576 MLS#73567550
STATUSActive Under Contract PROPERTY TYPEResidential - Single Family

Property Description

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 Jacobs 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.

158 Skyline Trl | MLS# 73567550

This single family home located at 158 Skyline Trl, Middlefield, MA 01243 is currently listed for sale with an asking price of $269,900. This property was built in 1837 and has 3 bedrooms and 3 full baths with 3576 sq. ft. Search Middlefield real estate on darrenmcgovern.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Full, Crawl Space, Sump Pump, Dirt Floor, Concrete
Basement: Yes
Cooling: None
Fenced: Yes
Heating: Forced Air, Electric Baseboard, Oil, Electric, Wood
Home Style: Colonial, Farmhouse
Lot Size: 1.00 Acres
Roof Type: Shingle
Taxes: $5,326
Year Built: 1837

Amenities

Porch
Rain Gutters
Barn/Stable

Feature Descriptions

Appliances: Electric Water Heater, Refrigerator, Washer
Building Area Total: 3576
Community Features: Walk/Jog Trails, Bike Path, Public School
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 19
Electric: Circuit Breakers
Exterior: Frame, Brick, Stone
Fencing: Fenced/Enclosed
GarageY/N: Yes
HeatingY/N: 1
Laundry: In Basement, Washer Hookup
Lot Features: Level
Other Structures: Barn/Stable
Parcel Number: M:406.0 B:0013 L:0000.0,4082131
Parking Features: Storage, Workshop in Garage, Barn, Off Street
Parking Total: 4
Patio And Porch: Porch
Rooms Total: 8
Sewer: Private Sewer
Utilities: Washer Hookup
Water: Shared Well

Local Schools

High School: Gateway Regional School
Middle School: Gateway Regional School
Elementary School: Chester Elementary/Littleville

Listed By / Shown By

Listed By

Agency Name: RE/MAX Compass
Agent Name: Dennis LeClair
Agency Phone: 413-568-0040

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Estimated Payment

$ 1,123.23 per month $600.68 Principal & Interest $443.83 Property Tax $78.72 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 09/13/2026. The listing information on this page last changed on 09/13/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sun 09/13/2026 12:00:14 AM EST) or MLSPIN MLS (last updated Sat 09/12/2026 11:38:36 PM EST) or Prime MLS (last updated Sat 09/12/2026 11:33:34 PM EST) or MREIS (last updated Sat 09/12/2026 11:55:16 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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