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 238862

  • 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: 6.7% last updated on Sep 29, 2022
* 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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14 Easland West Stockbridge MA 01266

West Stockbridge, MA14 Easland Rd

Price$4,850,000

Est. Mortgage: $/month

MLS Number 238758

  • Residential
  • Bathroom 8
  • Bedrooms 8
  • Square Feet 5,728
  • Year Built 1794

Blueberry hill is an historic legacy property enjoyed by four generations and available for the first time since 1938, a secluded retreat yet proximate to popular berkshires attractions. Surrounded by 95 acres of land, its sprawling private footprint makes this estate a coveted berkshires gem. The compound includes four residences that offer space for family, friends, and support staff - a 5 bedroom, 4.5 bath gracious main house, a converted barn 3 bedroom, 3 bath guest house, a 3 bedroom, 2 bath caretakers house with multiple garages for both cars and equipment, and a destination 2 bedroom, 1 bath coveted guest house at the top of the pasture. There are facilities for outdoor activities like tennis, swimming, hiking, a greenhouse and more. (see supplement)

Listed by Timothy Lovett and Fintan T Hanley of BERKSHIRE PROPERTY AGENTS,LLC

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Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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1 Lahey Cross Stockbridge MA 01262

Stockbridge, MA1 Lahey Cross Rd

Price$2,595,000

Est. Mortgage: $/month

Pending

MLS Number 237363

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,847
  • Year Built 1992

Custom built estate on a 22+ acre picturesque lot. Thoughtfully designed with exceptional detail and quality. Enjoy a winding tree-lined driveway, seasonally blooming landscape, renowned goshen stonework, in-ground pool, & guest house w/ private deck. In the main house, a 2-story foyer leads you to a grand living room w/ superb views, & a library perfect for book lovers. Farmhouse kitchen, dining room w/ fireplace, & sweeping windows lead you to a screened porch. A 2nd-floor primary suite includes walk-in closets, european style bath & dual pedestal sinks. Perfect for entertaining w/ 5 total bedrooms, butlers pantry, wine cellar, & plenty of outdoor space overlooking the manicured landscape. Nearby attractions: norman rockwell museum, berkshire botanical garden, tanglewood, & chesterwood.

Listed by Joshua Stephens of NON-MEMBER: Reciprocal

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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185-0-183 Pine Otis MA 01253

Otis, MA185-0-183 Pine Rd

Price$1,925,000

Est. Mortgage: $/month

MLS Number 237749

  • Residential
  • Bathroom 3
  • Bedrooms 6
  • Square Feet 3,416
  • Year Built 1111

Welcome to the berkshires & otis reservoir -the largest recreational lake in ma at 1085 acres.This listing is all about the land,the location & 150 ft of beautiful waterfront.The property consists of 3 parcels making up a unique, conforming 1.39 acre compound,with 4 well maintained docks, lakeside patio,2 homes and additional lot. Right on the lake is a 4 bedroom seasonal cottage with a new roof,wrap around porch & big water views. Build your dream home or use as is for a summer of family fun.The 2nd waterfront has a small, quaint,4 season home.A large front deck offers quieter,private lake views.Great for guests,winter getaways or summer rentals.The 3rd parcel is a .47acre lot with potential use as a garage or guest house site. Please enjoy the aerial photos to get a sense of the property

Listed by Kim Bergland of RED HORSE REAL ESTATE

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Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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797 State Richmond MA 01254

Richmond, MA797 State Rd

Price$1,650,000

Est. Mortgage: $/month

MLS Number 238105

  • Residential
  • Bathroom 12
  • Bedrooms 6
  • Square Feet 3,094
  • Year Built 2010

Welcome home to braemar an exquisite property featuring a main house, a guest house, barn and workshop on 13.6 pristine acres with glorious views. The main house with its open concept kitchen, custom cabinets and large island, plus dining and living rooms creates a great entertaining space. The pub/game room (adjacent to dining area) has everything you need to host your favorite sporting events and features a wall of sliding glass doors leading to a brand new deck where you can take in the views of the berkshire hills. 3 bedroom suites including a first floor primary suite. 4 full luxurious baths plus a half bath/laundry room on first floor. Radiant heat, mahogany and tile floors throughout, a home office, and finished walkout lower just perfect as a family room or for overflow guests.

Listed by Victoria A Standring and Melissa DiMassimo of STONE HOUSE PROPERTIES,LLC

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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390 Housatonic Lenox MA 01240

Lenox, MA390 Housatonic St

Price$527,000

Est. Mortgage: $/month

MLS Number 238804

  • Residential
  • Bathroom 1
  • Bedrooms 2
  • Square Feet 1,296
  • Year Built 1930

Ideally located 3 minutes from the center of lenox on 2+ acres of mature woodlands at the end of a long shared driveway, this special home and land exudes the beauty of living in new england. Whether you wish to make it your primary home, or possibly convert it to a guest house after building a new home on the property, you will enjoy the charm of an older home with lots of upgrades that include mini-split ac, efficient on-demand hot water, and new trex decks. The detached two car garage includes a separate home office/studio.

Listed by Jason Saphire of www.HomeZu.com

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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 Wilson West Stockbridge MA 01266

West Stockbridge, MA2 Wilson Rd

Price$495,000

Est. Mortgage: $/month

MLS Number 238585

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,040
  • Year Built 1987

A fantastic opportunity in one of the most sought after areas of west stockbridge. On the corner of wilson and west center this 7+ acre parcel is fully subdividable - creating a new building lot or the option for a full guest house on it's own parcel. Long gravel driveway leads to a completely private home site.

Listed by Cameron Volastro and Suzanne Crerar of STONE HOUSE PROPERTIES,LLC

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%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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 September 30, 2022 . 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.