# 158 Skyline Trl, Middlefield, MA 01243 > **TL;DR:** 3bd/3ba single family, $269,900 ($75/sqft), built 1837, 3,576 sqft. Est. $1,444/mo. Listed 69 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $269,900 | | Price/sqft | $75 | | Bedrooms | 3 | | Bathrooms | 3 full | | Square Feet | 3,576 | | Year Built | 1837 | | Lot Size | 43,560 sqft (1.00 acres) | | Property Type | Single Family (Single Family Residence) | | Status | Pending | | Days on Market | 69 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $1,365 | | Estimated Insurance | $79 | | **Total** | **$1,444** | ## Nearby Schools - **Elementary:** Chester Elementary/Littleville - **Middle:** Gateway Regional School - **High:** Gateway Regional School ## Property Highlights - Built in 1837 - 1.00 acre lot - 4 parking spaces ## Description ### Agent 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 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. ## Location - **Address:** 158 Skyline Trl, Middlefield, MA 01243 - **County:** Hampshire - **Coordinates:** 42.349625, -73.015599 - **Google Maps:** https://www.google.com/maps?q=42.349625,-73.015599 ## Listing Agent - **Name:** William Miner - **Brokerage:** RE/MAX COMPASS - **Broker Phone:** (413) 568-0040 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/158-Skyline-Trl_Middlefield_MA_01243_M38386-14646?f=listhub&s=MLSPIN&m=73567550&c=propsimple) ## Photos ![158 Skyline Trl - Photo 1](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3729692986r.jpg) ![158 Skyline Trl - Photo 2](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f4281192630r.jpg) ![158 Skyline Trl - Photo 3](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3553821334r.jpg) ![158 Skyline Trl - Photo 4](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f438867555r.jpg) ![158 Skyline Trl - Photo 5](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3883802401r.jpg) ![158 Skyline Trl - Photo 6](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3390019927r.jpg) ![158 Skyline Trl - Photo 7](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f1629453655r.jpg) ![158 Skyline Trl - Photo 8](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f1216503928r.jpg) ![158 Skyline Trl - Photo 9](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3699124250r.jpg) ![158 Skyline Trl - Photo 10](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f477079181r.jpg) ![158 Skyline Trl - Photo 11](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f1100059385r.jpg) ![158 Skyline Trl - Photo 12](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f247626563r.jpg) ![158 Skyline Trl - Photo 13](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f1377979634r.jpg) ![158 Skyline Trl - Photo 14](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f660155353r.jpg) ![158 Skyline Trl - Photo 15](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f404142567r.jpg) ![158 Skyline Trl - Photo 16](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f614007589r.jpg) ![158 Skyline Trl - Photo 17](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f1376781904r.jpg) ![158 Skyline Trl - Photo 18](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f336988025r.jpg) ![158 Skyline Trl - Photo 19](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f2733293952r.jpg) ![158 Skyline Trl - Photo 20](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f415543989r.jpg) ![158 Skyline Trl - Photo 21](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3526181544r.jpg) ![158 Skyline Trl - Photo 22](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f4106794558r.jpg) ![158 Skyline Trl - Photo 23](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f1150794906r.jpg) ![158 Skyline Trl - Photo 24](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f2312793532r.jpg) ![158 Skyline Trl - Photo 25](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f385769242r.jpg) ![158 Skyline Trl - Photo 26](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3149844303r.jpg) ![158 Skyline Trl - Photo 27](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3134440775r.jpg) ![158 Skyline Trl - Photo 28](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f4040343913r.jpg) ![158 Skyline Trl - Photo 29](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f950792075r.jpg) ![158 Skyline Trl - Photo 30](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f2039187352r.jpg) ![158 Skyline Trl - Photo 31](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f2425471117r.jpg) ![158 Skyline Trl - Photo 32](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f635611043r.jpg) ![158 Skyline Trl - Photo 33](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f1387455610r.jpg) ![158 Skyline Trl - Photo 34](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f1965850337r.jpg) ![158 Skyline Trl - Photo 35](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f2531366289r.jpg) ![158 Skyline Trl - Photo 36](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3738363968r.jpg) ![158 Skyline Trl - Photo 37](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f560801125r.jpg) ![158 Skyline Trl - Photo 38](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3275564445r.jpg) ![158 Skyline Trl - Photo 39](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f3244363141r.jpg) ![158 Skyline Trl - Photo 40](http://lh.rdcpix.com/b74239d2bacb570aec302ce0c78be3e9l-f197932506r.jpg) --- **MLS#:** 73567550 | **Updated:** 2026-10-26 **Source:** listhub *Copyright © 2026 MLS Property Information Network Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/158-skyline-trl-middlefield-ma-01243-d53460604dfb49e9a9000fc1fd80f958) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/158-skyline-trl-middlefield-ma-01243-d53460604dfb49e9a9000fc1fd80f958#listing", "url": "https://www.propertysimple.ai/listing/158-skyline-trl-middlefield-ma-01243-d53460604dfb49e9a9000fc1fd80f958", "name": "158 Skyline Trl, Middlefield, MA 01243", "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. 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