Berkshire, MA Homes

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  /44

  $685,000

  • 3 Beds
  • 3 Baths
  • 2,395 Sq Ft

  649 Hewins St, Sheffield, MA 01257

  Located on a pastoral country road in Sheffield, this thoughtfully updated early 1900s farmhouse with carriage house sits on 1 open acre with sweeping views to the west of conservation land. The home blends original character withmodern touches--vaulted ceilings, exposed beams, hard wood floors, and high-end finishes throughout. In the main house a sunlit kitchen anchors the home featuring custom

  Lauren Molk ELYSE HARNEY REAL ESTATE

  649 Hewins St, Sheffield, MA 01257
• 

  $68,000 Sold May 23, 2025

  • Land
  • 1.20 Acres
  • $56,667 per Acre

  • 326 Days On Market

  305 Ashley Falls Rd, Canaan, CT 06018

  Engineered open level lot in Prime area of the North West Corner of Connecticut. Perfect for retail or commercial business right on major Route 7 with GREAT exposure. Engineered for a 1,500 sq ft building with 10-12 car parking area. GREAT EXPOSURE!!! JUST BEFORE STATE LINE!!! Excellent property for the new or up and coming business owner or investor.

  Susan Belmonte Coldwell Banker Realty

  305 Ashley Falls Rd, Canaan, CT 06018
• 

  

  

  /11

  Est $199,343 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 875 Sq Ft

  704 S Main St, Sheffield, MA 01257

  704 S Main St, Sheffield, MA 01257
• 

  

  

  /26

  $749,000

  • 4 Beds
  • 3 Baths
  • 2,750 Sq Ft

  26 Granite Ave, Canaan, CT 06018

  Welcome to a circa 1882 Victorian home nestled on a picturesque street in the heart of Canaan, CT. This exceptional property set on 1.32 acres, offers a rare blend of historic elegance and contemporary living. The main residence boasts 4 bedrooms and 3 full baths. Step inside to discover three gracious first-floor parlors, adorned with original architectural details. These versatile spaces can

  Christopher Virtuoso KW Legacy Partners

  26 Granite Ave, Canaan, CT 06018
• 

  $700,000 Sold May 07, 2025

  • 700 Sq Ft
  • $1000/SF
  • 40 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1964

  62 Rocky Ln, Salisbury, CT 06068

  Discover the allure of lakeside living with this expansive 4-acre property in Salisbury, offering coveted water access rights to the East Twin Lake (Washining). Embrace the rustic charm of the existing three-season cottage nestled amidst a blend of woodland and open space, only a few hundred feet from shimmering water across the road. Envision your future as you plan the construction of your

  David Mallison William Pitt Sotheby's Int'l

  62 Rocky Ln, Salisbury, CT 06068
• 

  

  /33

  Est $542,529 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,415 Sq Ft

  45 Root Ln, Sheffield, MA 01257

  45 Root Ln, Sheffield, MA 01257
• 

  

  /28

  $1,145,000

  • 3 Beds
  • 4 Baths
  • 3,472 Sq Ft

  36 Old Turnpike Rd N, Canaan, CT 06018

  Modern New Construction on 8 Acres: Contemporary North Canaan Home - Discover refined modern elegance in this exceptional new construction home spanning 3,472 sq ft of thoughtfully designed living space on 8.34 private acres in North Canaan, Connecticut. This contemporary Litchfield County residence exemplifies luxury living with meticulous attention to detail, featuring energy-efficient heat

  Elyse Morris Elyse Harney Real Estate

  36 Old Turnpike Rd N, Canaan, CT 06018
• 

  

  /28

  $530,000 Sold May 01, 2025

  • 3,280 Sq Ft
  • $162/SF
  • 231 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1790

  690 N Main St, Sheffield, MA 01257

  Upgrade this property for residential use. This stunning building boasts a perfect blend of modern features and preserved post and beam architecture to maintain its timeless historic charm. Meticulously renovated and used by a master craftsman, it boasts a host of eco-friendly features ranging from owned solar panels, to offset electricity usage to radiant heating in the ground floor concrete. In

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  690 N Main St, Sheffield, MA 01257
• 

  

  /19

  Est $510,766 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,220 Sq Ft

  285 Salisbury Rd, Sheffield, MA 01257

  285 Salisbury Rd, Sheffield, MA 01257
• 

  

  /33

  $1,385,000

  • 3 Beds
  • 3 Baths
  • 2,460 Sq Ft

  35 Emmons Ln, Canaan, CT 06018

  CANAAN VALLEY LUXURY - The total renovation of this beautifully located single level home, rebuilt from the foundation up in 2024, has been done with unparalleled taste and style. Set just above the Whiting River and overlooking preserved land in an area of estate level properties, the serenity and timeless appeal of Canaan Valley surround you. The result is a virtually new home that is offered

  David Taylor Elyse Harney Real Estate

  35 Emmons Ln, Canaan, CT 06018
• 

  

  /41

  $250,000 Sold Apr 30, 2025

  • 1,765 Sq Ft
  • $142/SF
  • 169 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1793

  107 S Main St, Sheffield, MA 01257

  Step into a piece of history with this iconic property known as ''The Hatfield's,'' a beloved antique landmark in Sheffield. Built in 1793, the original home exudes historic charm with timeless architecture, in the late 1990s a separate wing was added, creating a flexible two-family configuration. Alternatively, it can easily be used as a spacious single-family residence. The home's basement has

  Mary Naylor LANCE VERMEULEN RE, INC

  107 S Main St, Sheffield, MA 01257
• 

  

  /51

  Est $487,646 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,866 Sq Ft

  259 Salisbury Rd, Sheffield, MA 01257

  259 Salisbury Rd, Sheffield, MA 01257
• 

  

  /34

  $775,000

  • 4 Beds
  • 2 Baths
  • 2,310 Sq Ft

  662 Foley Rd, Sheffield, MA 01257

  Nature-Lover's Retreat Enjoy the best of country living on 4.55 acres in Sheffield. Tucked away, this sunlit Cape offers privacy, and timeless charm. A wooded drive leads to a 4-bed, 2-bath home with 2,300 sq ft of living space and a warm, open-concept layout featuring wood-beamed ceilings and a spacious great room addition. The second-floor primary suite offers a peaceful escape, while the

  Claire Pollart LANCE VERMEULEN RE, INC

  662 Foley Rd, Sheffield, MA 01257
• 

  $5,250,000 Sold Apr 30, 2025

  • 2,300 Sq Ft
  • $2283/SF
  • 267 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1920

  29 Morgan Ln, Salisbury, CT 06068

  Welcome to: Heron Cove. For the first time on the market in over 60 years, one of the most coveted properties is nothing short of spectacular. At the very end of an unsuspecting private dirt road this home sits proudly overlooking the serene Washining Lake one of the Twin Lakes. The property boasts a 180+ degree, truly one-in-a-life-time-view with 497 feet of water frontage. Walk through the

  Lenore Mallett William Pitt Sotheby's Int'l

  29 Morgan Ln, Salisbury, CT 06068
• 

  

  /47

  Est $752,377 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  170 Oak St, Sheffield, MA 01257

  170 Oak St, Sheffield, MA 01257
• 

  

  /40

  $920,000

  • 5 Beds
  • 3.5 Baths
  • 3,752 Sq Ft

  11 College Hill Rd, Canaan, CT 06018

  Welcome to Owls Nest - a peaceful and private retreat tucked away on over 5 acres in the hills of Canaan in the foothills of the Berkshires. This beautifully maintained colonial offers 4 bedrooms, 3.5 bathrooms, and timeless charm throughout. Upstairs, all bedrooms feature hardwood floors, while the main level boasts 2 wood-burning fireplaces, a spacious living room, a formal dining room, and a

  Dave Jones Dave Jones Realty, LLC

  11 College Hill Rd, Canaan, CT 06018
• 

  $413,400 Sold Apr 28, 2025

  • 2,686 Sq Ft
  • $154/SF
  • 13 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1991

  68 Allyndale Rd, Canaan, CT 06018

  Welcome to this Colonial nestled on a tranquil and scenic lot, perfect for creating lasting memories. From the moment you arrive, the charm of this property is unmistakable. The main level greets you with a versatile open floor plan adorned with hardwood floors, seamlessly connecting the dining and living rooms-ideal for both everyday living and entertaining. At the heart of the home is the

  Jonathan Gineo Silver and Oak Realty

  68 Allyndale Rd, Canaan, CT 06018
• 

  

  /40

  Est $716,129 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,792 Sq Ft

  647 Silver St, Sheffield, MA 01257

  647 Silver St, Sheffield, MA 01257
• 

  

  /40

  $1,240,000

  • 5 Beds
  • 4.5 Baths
  • 3,100 Sq Ft

  60 Parsley Ln, Sheffield, MA 01257

  Nestled at the end of a quiet country cul-de-sac, this newly built 5-bedroom, 4.5-bath home embodies refined country living. A dramatic primary suite offers dual walk-in closets and a spa-inspired bath with soaking tub, while a first-floor ensuite bedroom enhances comfort and flexibility. The gas fireplace living room and chef's kitchen create a seamless flow for entertaining, extending to a

  Vashti Poor LANCE VERMEULEN RE, INC

  60 Parsley Ln, Sheffield, MA 01257
• 

  $250,000 Sold Mar 31, 2025

  • Land
  • 1.84 Acres
  • $135,870 per Acre

  • 34 Days On Market

  46 Rocky Ln, Salisbury, CT 06068

  A wonderful opportunity to build your lake getaway. This 1.84 acre lot has deeded access to Lake Washining, the larger of the Twin Lakes in northern Salisbury. The building lot had engineering done some years back, but should be reverified by a buyer, A short walk takes you to the "park reserve", a shared lakefront parcel where owners may access the lake and keep their boats. Twin Lakes are

  Mimi Harson William Pitt Sotheby's Int'l

  46 Rocky Ln, Salisbury, CT 06068
• 

  

  /3

  Est $529,134 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,592 Sq Ft

  283 Silver St, Sheffield, MA 01257

  283 Silver St, Sheffield, MA 01257
• 

  

  /75

  $895,000

  • 9 Beds
  • 7 Baths
  • 5,267 Sq Ft

  567 S Main St, Sheffield, MA 01257

  Charming Multi-Home Property in Sheffield. Welcome to a rare homestead tucked away on 11 acres of peace and privacy in Sheffield. This inviting property offers an ideal setup for multi-generational living or families seeking extra space and privacy. Main House with (4) 1BR and (1) 2BR apartments, a second 3 BR home, and a three-bay garage. A short drive to Great Barrington (15 mins) and North

  Claire Pollart LANCE VERMEULEN RE, INC

  567 S Main St, Sheffield, MA 01257
• 

  $975,000 Sold Mar 28, 2025

  • 1,916 Sq Ft
  • $509/SF
  • 25 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1960

  442 Twin Lakes Rd, Salisbury, CT 06068

  This well-kept home on over 4 acres in the scenic Twin Lakes area of Salisbury is complete with deeded water rights on Lake Washining. This home features a renovated kitchen, alongside a welcoming Living Room, Dining Room, and cozy Sitting Room equipped with a wood-burning fireplace. Each main living area has easy access to an expansive deck, where you can enjoy the serene surroundings. The

  Holly Leibrock Elyse Harney Real Estate

  442 Twin Lakes Rd, Salisbury, CT 06068
• 

  

  /23

  Est $623,204 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  233 Hulett Hill Rd, Sheffield, MA 01257

  233 Hulett Hill Rd, Sheffield, MA 01257
• 

  

  /33

  $798,000

  • 3 Beds
  • 2.5 Baths
  • 3,082 Sq Ft

  86 Main St, Sheffield, MA 01257

  This gracious vintage home has been thoughtfully renovated and lovingly maintained by the current owners for over 20 years. High ceilings, wonderful light, spacious rooms, a ''walk to everything'' in town location, and residential/commercial zoning provide comfort and unlimited possibilities. A 1,000 sq. ft. outbuilding with water & electric service adds more potential. Beautiful period

  David Taylor ELYSE HARNEY REAL ESTATE

  86 Main St, Sheffield, MA 01257
• 

  $155,000 Sold Mar 24, 2025

  • 1,872 Sq Ft
  • $83/SF
  • 1 Day On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1777

  271 E Canaan Rd, East Canaan, CT 06024

  Located in the heart of farm country in North Canaan, 1777 farmhouse 3 bedrooms, 2 baths, attached barn/storage area. Conveniently located on Rt 44 short trip to shopping/golf/restaurants. Needs some renovations/interior and exterior paint. Fireplace is not in working order. Sold "as is" By appointment only.

  Nadia Corvo Northwest CT Realty

  271 E Canaan Rd, East Canaan, CT 06024
• 

  

  /71

  Est $642,000 Not Listed For Sale

  • 9 Beds
  • 12 Baths
  • 8,623 Sq Ft

  2128 Canaan Southfield Rd, Southfield, MA 01259

  2128 Canaan Southfield Rd, Southfield, MA 01259
• 

  

  /49

  $798,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,128 Sq Ft

  18 Cross To Canaan Valley Rd, New Marlborough, MA 01259

  Set in a small country neighborhood, this stunning 4 Bedroom is perfect for entertaining friends and family. The 1st floor includes an open kitchen and dining area with granite countertops and high ceilings, a cozy sunken living room with propane fireplace, and a spacious first floor bedroom suite. Sliding French doors throughout the 1st floor bring in plenty of light and lead onto a 50' mahogany

  Vashti Poor LANCE VERMEULEN RE, INC

  18 Cross To Canaan Valley Rd, New Marlborough, MA 01259
• 

  

  /14

  $210,000 Sold Mar 18, 2025

  • 2,258 Sq Ft
  • $93/SF
  • 92 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1957

  689 N Main St, Sheffield, MA 01257

  4-bedroom, 2-family house on a main road, offering great potential with some TLC. This duplex includes a very spacious backyard as well as a detached garage. Just north of Sheffield Center. Fantastic opportunity for a buyer who is looking to offset the mortgage with rental income or a potential investment. This property is commercially zoned making it a a fantastic location for Sheffields

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  689 N Main St, Sheffield, MA 01257
• 

  

  /46

  Est $649,838 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 4,232 Sq Ft

  2383 Canaan Southfield Rd, Southfield, MA 01259

  2383 Canaan Southfield Rd, Southfield, MA 01259
• 

  

  /36

  $680,000 Pending

  • 1 Bed
  • 1.5 Baths
  • 1,080 Sq Ft

  28 Rocky Ln, Salisbury, CT 06068

  A rare opportunity awaits on Rocky Lane. This beautifully renovated, energy-efficient one-bedroom cottage offers a serene retreat with deeded Right of Way access to East Twin Lakes. Perfect for swimming, boating, kayaking, or fishing on one of Connecticut's finest managed trout and salmon lakes. The home has been fully updated with newer mechanicals, central air, whole-house generator, and

  Julie Einhorn Compass Connecticut, LLC

  28 Rocky Ln, Salisbury, CT 06068
• 

  $650,000 Sold Mar 10, 2025

  • 1,396 Sq Ft
  • $466/SF
  • 34 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1910

  5 Prospect St, Canaan, CT 06018

  Meet: Isabella. Wrapped in white and perched on a small hill. She stands proudly with a view of the charming village of Falls Village. The front of the house adorns a lovely small porch with just enough room for a rocking chair or swing. The landscape is thoughtfully peppered with stone walls, hydrangea, boxwoods and a pea stone patio. A barn flanks the backside of the property which would make

  Elvia Gignoux William Pitt Sotheby's Int'l

  5 Prospect St, Canaan, CT 06018
• 

  

  /20

  Est $346,717 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  34 Clark Way, Southfield, MA 01259

  34 Clark Way, Southfield, MA 01259
• 

  

  /9

  $89,000

  • Land
  • 3.82 Acres
  • $23,298 per Acre

  62 Hadsell St, New Marlborough, MA 01230

  Wonderful opportunity to build your dream Berkshire home or getaway. This picturesque property is situated on just under 4 acres off a quiet paved country road. The winding Umpachenee River backs up to the land and it's modest building envelope. Quiet and serene country living yet not far from the bustling towns of Great Barrington and Sheffield. Quick access to the Mill River general store and

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  62 Hadsell St, New Marlborough, MA 01230
• 

  

  /27

  $419,000 Sold Feb 28, 2025

  • 1,603 Sq Ft
  • $261/SF
  • 19 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1987

  487 Polikoff Rd, Ashley Falls, MA 01222

  Move in ready, younger cape home. New kitchen, hickory flooring and interior paint. Nicely updated bathrooms. Composite deck overlooking a private yard with woods behind. The smaller of the 4 bedrooms does not have a closet.

  Tim Hart HART REALTY

  487 Polikoff Rd, Ashley Falls, MA 01222
• 

  

  /78

  Est $1,295,920 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,005 Sq Ft

  128 Konkapot Rd, Southfield, MA 01259

  128 Konkapot Rd, Southfield, MA 01259
• 

  

  /13

  $350,000

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  412 Berkshire School Rd, Sheffield, MA 01257

  1995 split level home on .50 acres walking distance to the village of Sheffield. 3 bedrooms 1 full bath....eat in kitchen, living room....unfinished lower level....electric and forced hot air propane fired heat, vinal siding......septic.(Title 5 completed)....private water company

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  412 Berkshire School Rd, Sheffield, MA 01257
• 

  

  /31

  $735,000 Sold Feb 28, 2025

  • 2,113 Sq Ft
  • $348/SF
  • 98 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  571 Hayes Hill Rd, New Marlborough, MA 01230

  With amazing views from every room, this single level home offers many possibilities for its next Steward. Currently a two bedroom two bath home, this property has lots of possible options for change over the 2100 Sq Ft. An over sized basement with high ceilings has more space and storage than you could wish for. With mature landscaping, an outbuilding and fruit trees galore, this is the country

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  571 Hayes Hill Rd, New Marlborough, MA 01230
• 

  

  /54

  Est $1,156,637 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,164 Sq Ft

  227 Konkapot Rd, Southfield, MA 01259

  227 Konkapot Rd, Southfield, MA 01259
• 

  

  /43

  $475,000

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  127 Old Joe Rd, Great Barrington, MA 01230

  Nestled on a quiet country road, this well-kept ranch offers the ease of single-level living with ample space to relax, entertain, and make your own. The home features an inviting floor plan with plenty of natural light and room for upgrades, allowing you to personalize each space to your taste.Enjoy seamless indoor-outdoor living with a large back deck--perfect for gatherings or quiet mornings

  Tony Segalla LANCE VERMEULEN RE, INC

  127 Old Joe Rd, Great Barrington, MA 01230

Showing Results 41 - 80, Page 2 of 18