$269,900
158 Skyline Trl
Middlefield, MA, 01243
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 Details
Price:
$269,900
MLS #:
73567550
Status:
Pending
Beds:
3
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Aug 24, 2026
Finished Sq Ft:
3,576
Total Sq Ft:
3,576
Lot Size:
43,560 sqft / 1.00 acres (approx)
Year Built:
1837
Schools
Elementary School:
Chester Elementary/Littleville
Middle School:
Gateway Regional School
High School:
Gateway Regional School
Interior
Above Grade Finished Area
3576
Appliances
Electric Water Heater, Refrigerator, Washer
Bathrooms
3 Full Bathrooms
Cooling
None
Heating
Forced Air, Electric Baseboard, Oil, Electric, Wood
Laundry Features
In Basement, Washer Hookup
Exterior
Architectural Style
Colonial, Farmhouse
Community Features
Walk/Jog Trails, Bike Path, Public School
Construction Materials
Frame, Brick, Stone
Exterior Features
Porch, Rain Gutters, Barn/Stable
Fencing
Fenced/Enclosed
Lot Features
Level
Open Parking Spaces
4
Other Structures
Barn/Stable
Parking Features
Storage, Workshop in Garage, Barn, Off Street
Parking Spots
4
Parking Total
4
Patio And Porch Features
Porch
Roof
Shingle
Financial
Tax Year
2025
Taxes
$5,326
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
More About MarieMortgage Calculator
Map
Current real estate data for Single Family in Middlefield as of Sep 18, 2026
9
Single Family Listed
1,049
Avg DOM
184
Avg $ / SqFt
$387,411
Avg List Price
Community
- Address158 Skyline Trl Middlefield MA
- CityMiddlefield
- CountyHampshire
- Zip Code01243
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Property Summary
- 158 Skyline Trl Middlefield MA is a Single Family for sale in Middlefield, MA, 01243. It is listed for $269,900 and features 3 beds, 3 baths, and has approximately 3,576 square feet of living space, and was originally constructed in 1837. The current price per square foot is $75. The average price per square foot for Single Family listings in Middlefield is $184. The average listing price for Single Family in Middlefield is $387,411. To schedule a showing of MLS#73567550 at 158 Skyline Trl in Middlefield, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of RE/MAX Compass. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
158 Skyline Trl
Middlefield, MA










































