Berkshire County Homes with Guest Houses

MA Homes For Sale with a Guest HouseFind all Berkshire County homes for sale with guest houses below. Browse a variety of listings that provide the privacy you need for your family while being able to spend quality time with your extended family or close friends visit. Learn about life in the Berkshires!

Western MA Homes with a Guest House for Sale

Contact the Alton & Westall Real Estate Agency online or call 413-458-8366 for more information or to set up a showing for any property below. 

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24 & 30 Berkshire Heights Great Barrington MA 01230

MLS Number 232672

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 6,240
  • Year Built 1918

A rare estate offering in the berkshires. Breathtaking southern and western views from this historically important great barrington estate. Designed by charles platt for charles freer of the renowned freer gallery in dc, and constructed of stone quarried from the property, this one floor layout was well ahead of its time. The main house has a large, comfortable living room with views from massive windows, a library, a gracious dining room, all with fireplaces. The property encompasses a stable and riding ring, pool, orchard, vineyard and two fully equipped guest houses and a caretaker's home. This is a rare opportunity to own a unique nearly 50 acre estate with magnificent views - all close to great barrington.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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12 Red Rock West Stockbridge MA 01266

West Stockbridge, MA12 Red Rock Rd

Price$1,950,000

Est. Mortgage: $/month

MLS Number 229485

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 5,824
  • Year Built 1986

Magical, secluded compound set oh-so-privately amongst birch groves down a winding country lane ... Simply stunning views surround this impressive contemporary home, thoughtfully designed to welcome natural light into every restful room. The main residence is graciously open, with many fireplaces & a view in every direction. Clay-bottomed swimming pond, two-bedroom studio/guest house, all on 22+ acres. Tucked away, yet only minutes to the charming and artistic village of west stockbridge. Just a short drive to tanglewood, lenox, and the best of the berkshires!

Listed by Nancy K. Kalodner and Brandon White of COHEN & WHITE ASSOCIATES

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Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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55 Old Stockbridge Lenox MA 01240

Lenox, MA55 Old Stockbridge Rd

Price$895,000

Est. Mortgage: $/month

MLS Number 234026

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,235
  • Year Built 1985

Just a short stroll from the center of lenox you will come to this private, quiet, enchanting retreat on over an acre of bucolic, landscaped land. An existing sweet ranch home can be expanded or used as a guest house for a family/friend compound. The southeast boundary is a brook and most of the surrounding property is protected land. The oversized garage/outbuilding can be utilized as a home office or studio. Let your imagination be your guide for this unique setting.

Listed by Allen Bassen of BERKSHIRE HOMES AND CONDOS

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Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Navin Lee MA 01238

Lee, MA2 Navin Heights

Price$695,000

Est. Mortgage: $/month

Pending

MLS Number 236120

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,848
  • Year Built 1962

Gorgeous mid-century modern 3bd/3ba home overlooking conservation land with distant southwestern views. Light filled open space with both inside and outside fireplaces. One minute to lee or only four to downtown lenox, tanglewood in ten, and i-90 in three. The property comes with an additional buildable lot with town water, sewer, and gas-- perfect for a full-sized guest house or pool house. Two car garage, high speed internet, and brand-new central air conditioning. Extremely convenient and special location. A rare gem!

Listed by Jason Saphire of WWW.ENTRYONLY.COM

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1250 Simonds Williamstown MA 01267

Williamstown, MA1250 Simonds Rd

Price$325,000

Est. Mortgage: $/month

MLS Number 235816

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,584
  • Year Built 1780

1780 colonial on the williamstown -pownal line. First floor offers; open flow eat in kitchen, formal dining area, living room, full bath and a large sitting den. Second floor offers 3 bedrooms and 2 full baths. Third floor is a walk up attic with multiple rooms. Wood floors throughout with charm of the 1700's paired with today's function. Updates include; insulation, newer oil fired heating system (2014) installed in 2015, most vinyl windows and siding, 100 amp circuit breaker panels. Large yard and mountain views! Guest house out back is a single wide trailer, could stay or could be removed, your choice. The location allows school choice for either williamstown or southwestern vt schools

Listed by Jason Nocher of NOCHER REALTY

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Based on information submitted to BCMLS  as of December 1, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.