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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$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 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: 5.3% last updated on May 12, 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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4 & 8 Boice Egremont MA 01252

Egremont, MA4 & 8 Boice Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 237556

  • Residential
  • Village North Egremont
  • Bathroom 8
  • Bedrooms 6
  • Square Feet 6,337

Nine glorious park-like acres set on a broad expanse of the pristine green river. Tastefully renovated in 2020 and impeccably maintained since, the main house (4bd, 5ba) and the guest house (2bd, 2ba) offer a variety of living and outdoor spaces to suit all moods and seasons. The main house with a southeast orientation has a contemporary open plan which flows out to the lawn and gardens and down to the river past mature apple trees, berry bushes and a gated flower and vegetable garden. The second floor primary suite with bountiful light includes a fabulous private roof deck, and a home office, both with views to the river and hills beyond. Three additional bedrooms and baths, and two dens in the main house offer plenty of space for friends and family.

Listed by Claudia Crane of BERKSHIRE PROPERTY AGENTS,LLC

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$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 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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12 Red Rock West Stockbridge MA 01266

West Stockbridge, MA12 Red Rock Rd

Price$1,950,000

Est. Mortgage: $/month

Pending

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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$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 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 Eaton Pittsfield MA 01201

Pittsfield, MA1 Eaton Ln

Price$589,500

Est. Mortgage: $/month

Pending

MLS Number 236993

  • Residential
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 5,023
  • Year Built 1913

Hidden gem with attached guest house! One eaton lane, centrally located near downtown pittsfield yet tucked away on a quiet side street with only five homes. The property boasts a spacious main house with 4 bedrooms & 2 full baths. The attached guest home has kitchen, full bath, living room, & bedroom. Relax & sip your morning coffee on your spacious and inviting front porch, & then enjoy easy access to theatres, restaurants & shops downtown. One of a kind opportunity not to be missed!

Listed by Barbara K. Greenfeld,Broker Associate of ROBERTS & ASSOC. REALTY,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of May 16, 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.