LRG: Luxury Residential Group
  • Login  /
  • 355 Boylston St
  • (617) 233-5800
Redefining Boston Real Estate

158 Skyline Trl, Middlefield, MA

Middlefield Single Family Get directions

Click for Search Results
158 Skyline Trl, Middlefield, MA Photo #1
158 Skyline Trl, Middlefield, MA Photo #2
158 Skyline Trl, Middlefield, MA Photo #3
158 Skyline Trl, Middlefield, MA Photo #4
158 Skyline Trl, Middlefield, MA Photo #5
158 Skyline Trl, Middlefield, MA Photo #6
158 Skyline Trl, Middlefield, MA Photo #7
158 Skyline Trl, Middlefield, MA Photo #8
158 Skyline Trl, Middlefield, MA Photo #9
158 Skyline Trl, Middlefield, MA Photo #10
158 Skyline Trl, Middlefield, MA Photo #11
158 Skyline Trl, Middlefield, MA Photo #12
158 Skyline Trl, Middlefield, MA Photo #13
158 Skyline Trl, Middlefield, MA Photo #14
158 Skyline Trl, Middlefield, MA Photo #15
158 Skyline Trl, Middlefield, MA Photo #16
158 Skyline Trl, Middlefield, MA Photo #17
158 Skyline Trl, Middlefield, MA Photo #18
158 Skyline Trl, Middlefield, MA Photo #19
158 Skyline Trl, Middlefield, MA Photo #20
158 Skyline Trl, Middlefield, MA Photo #21
158 Skyline Trl, Middlefield, MA Photo #22
158 Skyline Trl, Middlefield, MA Photo #23
158 Skyline Trl, Middlefield, MA Photo #24
158 Skyline Trl, Middlefield, MA Photo #25
158 Skyline Trl, Middlefield, MA Photo #26
158 Skyline Trl, Middlefield, MA Photo #27
158 Skyline Trl, Middlefield, MA Photo #28
158 Skyline Trl, Middlefield, MA Photo #29
158 Skyline Trl, Middlefield, MA Photo #30
158 Skyline Trl, Middlefield, MA Photo #31
158 Skyline Trl, Middlefield, MA Photo #32
158 Skyline Trl, Middlefield, MA Photo #33
158 Skyline Trl, Middlefield, MA Photo #34
158 Skyline Trl, Middlefield, MA Photo #35
158 Skyline Trl, Middlefield, MA Photo #36
158 Skyline Trl, Middlefield, MA Photo #37
158 Skyline Trl, Middlefield, MA Photo #38
158 Skyline Trl, Middlefield, MA Photo #39
158 Skyline Trl, Middlefield, MA Photo #40
Previous Photo Next Photo

Image 1 of 40

previous
  • Photo #1
  • Photo #2
  • Photo #3
  • Photo #4
  • Photo #5
  • Photo #6
  • Photo #7
  • Photo #8
  • Photo #9
  • Photo #10
  • Photo #11
  • Photo #12
  • Photo #13
  • Photo #14
  • Photo #15
  • Photo #16
  • Photo #17
  • Photo #18
  • Photo #19
  • Photo #20
  • Photo #21
  • Photo #22
  • Photo #23
  • Photo #24
  • Photo #25
  • Photo #26
  • Photo #27
  • Photo #28
  • Photo #29
  • Photo #30
  • Photo #31
  • Photo #32
  • Photo #33
  • Photo #34
  • Photo #35
  • Photo #36
  • Photo #37
  • Photo #38
  • Photo #39
  • Photo #40
next

Unit Information

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.

Additional Details
Status: ACT
Type: Single Family, Single Family Residence
Zip Code: 01243
Parking
Garage Capacity: 4
Parking: Storage,Workshop in Garage,Off Street
Parking Spaces: 4
Rooms and Dimensions
Total Rooms: 8
Has Basement: Yes
Login to view all MLS information
 

Loading...

$269,900

  • Listing ID: 73567550
  • Bedrooms: 3
  • Full Baths: 3
  • Living Area: 3,576 sqft Convert
  • Lot Size: 43,560 sqft Convert
  • Acres: 1

  • View description
Inquire About This Listing
Luxury Residential Group

Luxury Residential Group

(617) 233-5800

Receive more info or arrange a tour

When you are ready, please contact us and we will put our unrivaled knowledge of the Boston real estate market to work for you. Whether you are buying a luxury condo or renting a luxury apartment, we pledge to make your experience as stress free and enjoyable as possible.

Please call, email, or send us a message through the web form below. An LRG Real Estate agent will contact you promptly.

  • reset
 
Content © 2026 MLS Property Information Network, Inc. The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Dennis LeClair of RE/MAX Compass. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.

close x
Forgot password?