Ashley Falls, MA Homes for Sale

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  /53

  $695,000

  • 4 Beds
  • 4 Baths
  • 3,455 Sq Ft

  64 Hewins St, Sheffield, MA 01257

  A rare & authentic 1842 post & beam farmhouse w/ many original details. This one-of-a-kind antique home awaits the reinvention & stewardship of it's next owners. In the same family for the last 125 years, and with just two prior owners since being built, the structure features post & beam construction, two original fireplaces, antique hardware, woodwork and doors that exemplify early American

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 296-3500

  64 Hewins St, Sheffield, MA 01257
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  /40

  $499,000

  • 6 Beds
  • 2.5 Baths
  • 3,184 Sq Ft

  119 S Main St, Sheffield, MA 01257

  A unique opportunity to make this terrific property your own, with a separate bungalow apartment for income or other home business uses. Property features a 6 bedroom, 2 bath 1880's Victorian with a classic yet casual style. First floor features a sunny living room, large country kitchen, formal dining room w/ built-ins, and front parlor/bedroom. Second floor offers 5 bedrooms, 2 full baths, and

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 481-1637

  119 S Main St, Sheffield, MA 01257
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  /10

  $345,000

  • Land
  • 37 Acres
  • $9,215 per Acre

  0 Old Turnpike Rd N, Canaan, CT 06018

  37.437 acres bordering the Konkapot River. A small portion of this land on the back side is in Massachusetts. New survey is complete. Nice location with great possibilities!

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  (860) 609-6471

  0 Old Turnpike Rd N, Canaan, CT 06018
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  /36

  $950,000

  • 2 Beds
  • 2.5 Baths
  • 1,508 Sq Ft

  48 Preston Ln, Salisbury, CT 06068

  Tucked away on a private road with shared lake access to the serene waters of Lake Washinee, this custom one-level home offers the perfect blend of natural beauty, thoughtful design, and modern comfort. Set on just over three wooded acres with a tranquil stream, the property offers privacy and peaceful surroundings in every direction. The original home was built in 1950. There was a complete

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  (860) 792-5920

  48 Preston Ln, Salisbury, CT 06068
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  /25

  $335,000

  • 3 Beds
  • 1.5 Baths
  • 1,232 Sq Ft

  182 Church St, Canaan, CT 06018

  Welcome to this classic 3-bedroom Colonial, ideally situated on the outskirts of town yet just a short stroll to the sidewalk district. This home blends timeless charm with functional living spaces, perfect for families or anyone looking for a comfortable setting with easy access to town amenities. Step inside to discover hardwood floors that flow throughout the home, adding warmth and character

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  (860) 295-3073

  182 Church St, Canaan, CT 06018
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  /9

  $379,500

  • Land
  • 6 Acres
  • $60,720 per Acre

  0 S Main St, Sheffield, MA 01257

  Mountain views with Rt 7 access. Whether you are interested in a private residence to farm, raise horses, or escape the city life or if you are looking for a business opportunity with amazing Rt 7 exposure this land is the perfect opportunity. Totaling 6.25 acres of completely usable, flat, dry land. Currently the fields are hayed and have an approximate 1 acre vineyard. The 6.25 acres is made up

  Grace Golden Equine Homes Real Estate, LLC

  0 S Main St, Sheffield, MA 01257
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  /40

  $999,000

  • 3 Beds
  • 3 Baths
  • 2,878 Sq Ft

  1166 Rannapo Rd, Sheffield, MA 01257

  It's no wonder why this property is the home of Berkshire county's oldest elm tree! The abundant sunshine, quietude and peace would make anybody want to set down roots and stay a while. This light filled home has refinished wood floors throughout the main level. Kitchen has granite counters, ample cabinet space, pantry and large island. As part of the open floor plan there is a bright dining room

  Grace Golden Equine Homes Real Estate, LLC

  1166 Rannapo Rd, Sheffield, MA 01257
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  /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
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  /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
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  /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
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  /31

  $1,350,000

  • 3 Beds
  • 2.5 Baths
  • 3,038 Sq Ft

  52 Cooper Hill Rd, Salisbury, CT 06068

  This is a unique chance to enjoy stunning views of Bear Mountain from a contemporary home featuring expansive windows that showcase the scenery, set on nearly 20 acres that stretch across Salisbury, CT, and Sheffield, MA. The bright sunshine and lofty ceilings, along with a screened porch and two upper-level decks, seamlessly blend indoor and outdoor living in this lovely residence. The

  Holly Leibrock Elyse Harney Real Estate

  52 Cooper Hill Rd, Salisbury, CT 06068
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  /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
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  /47

  $895,000

  • 3 Beds
  • 2 Baths
  • 2,057 Sq Ft

  20 Hillside Ln, Sheffield, MA 01222

  Beautiful, light and bright open concept chalet style home with floor to ceiling windows, cathedral ceilings, woodstove, renovated kitchen with new energy efficient appliances and adjacent dining area. Main floor has 2 bedrooms and a lovely renovated full bath with a walk-in shower, and a large mudroom to store all your outdoor gear. Second floor has the primary suite with vaulted ceilings,

  Sarah Dixon LANCE VERMEULEN RE, INC

  20 Hillside Ln, Sheffield, MA 01222
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  /40

  $1,240,000

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

  60 Parsley Ln, Sheffield, MA 01257

  This newly constructed 5-bedroom farmhouse is priced well below the current cost to build per square foot--truly an exceptional value! Tucked away in a well-established neighborhood convenient to both the Berkshires and Litchfield Connecticut, this energy-efficient home features spray foam insulation and a ductless AC/heat pump system. The open kitchen/dining area is filled with natural light,

  Vashti Poor LANCE VERMEULEN RE, INC

  60 Parsley Ln, Sheffield, MA 01257
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  /75

  $895,000 Open Sun 12:30PM - 2PM

  • 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
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  /17

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  1786 S Undermountain Rd, Sheffield, MA 01257

  Classic 3-Bedroom Cape with Pool - Perfectly positioned between NW Connecticut and Sheffield, MA in the Berkshires. Sheffield is the oldest Town in Berkshire County - the township was purchased in 1724 from Chief Konkapot and other Stockbridge Native Americans. This bright, lovely 3-Bedroom Cape features a beautiful, heated pool, a Bedroom and Full Bath on the Main Floor, 2 Bedrooms and another

  Juliet Moore ELYSE HARNEY REAL ESTATE

  1786 S Undermountain Rd, Sheffield, MA 01257
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  /54

  $1,190,000

  • 4 Beds
  • 2.5 Baths
  • 3,155 Sq Ft

  405 S Undermountain Rd, Sheffield, MA 01257

  Idyllic Contemporary Cape on Sprawling 13 Acres in Sheffield - Welcome to 405 South Undermountain Road, where the charm of a classic cape meets the allure of modern living on 13 private acres in Sheffield. Built in 1955 and beautifully updated, this home strikes a harmonious balance between comfort and elegance. Offering an open floor plan with 2 full baths, one 1/2 bath and a functional tiled

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  405 S Undermountain Rd, Sheffield, MA 01257
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  /42

  $995,000

  • 3 Beds
  • 3.5 Baths
  • 2,600 Sq Ft

  594 Shunpike Rd, Sheffield, MA 01257

  Beautifully renovated 2600 sq. ft. Gambrel-style home offering the perfect balance of privacy, comfort, and modern convenience. Step into a welcoming, open foyer that leads to an expansive living space with all-new features, including wood flooring, central air/heat, a full house generator, & updated plumbing/electrical systems. The heart of the home is a brand-new kitchen, complete with sleek

  Claire Pollart LANCE VERMEULEN RE, INC

  594 Shunpike Rd, Sheffield, MA 01257
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  /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
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  /60

  $998,000

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  856 Barnum St, Sheffield, MA 01257

  Modernist delight in a Berkshire pastoral setting. A refined retreat where every detail reflects quality and style. Designed by acclaimed architect Deby Reiser, this light-filled three-bedroom, three-bath home blends the sophistication of urban design with the calm of Berkshire countryside living. Tucked away on a quiet country road beside Moon In the Pond Farm an eco-friendly farm with peaceful

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  856 Barnum St, Sheffield, MA 01257
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  /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
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  /43

  $475,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,152 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
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  /21

  $110,000

  • Land
  • 7 Acres
  • $15,559 per Acre

  730 Clayton Rd, Sheffield, MA 01222

  BOG LOVERS, come look. Officially designated to be a Bog, this property could be a great one to own, for observing its nature views that change the year around. Whether you would want to build a home, or build a viewing platform for regular visits, it has 7+ acres with roughly 60-70% in a bog like status, the remainder being usable for building and walking along the bog's boundaries. All earlier

  Robin Leech Robinson Leech Real Estate

  730 Clayton Rd, Sheffield, MA 01222
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  /53

  $695,000

  • 6 Beds
  • 5 Baths
  • 4,572 Sq Ft

  604 Sheffield Plain, Sheffield, MA 01257

  A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and

  Tony Segalla LANCE VERMEULEN RE, INC

  604 Sheffield Plain, Sheffield, MA 01257
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  /54

  $649,000

  • 5 Beds
  • 2.5 Baths
  • 2,750 Sq Ft

  168 Main St, Sheffield, MA 01257

  Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra

  Tony Segalla LANCE VERMEULEN RE, INC

  168 Main St, Sheffield, MA 01257
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  /44

  $1,600,000

  • 9 Beds
  • 4.5 Baths
  • 8,406 Sq Ft

  2049 S Undermountain Rd, Sheffield, MA 01257

  An exceptional opportunity awaits on 11 private acres in Sheffield. This unique property, currently utilized as a functional therapy facility, offers a massive footprint and a flexible canvas for your next venture. The centerpiece is an 8,000+ sq. ft. building comprised of over 10 offices, multiple conference rooms, common areas, and three residential apartments, creating an ideal setup for a

  Tony Segalla LANCE VERMEULEN RE, INC

  2049 S Undermountain Rd, Sheffield, MA 01257
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  /30

  $695,000

  • 3 Beds
  • 6 Baths
  • 4,044 Sq Ft

  1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222

  Old Historic Village downtown location! The centrally located Post Office building constructed in 1860, presents a unique opportunity for both residential and commercial use. Its strategic location ensures consistent foot traffic, making it an invaluable cornerstone of village life. With no mail delivery service in Ashley Falls, the Post Office attracts local residents daily. This building is

  Tony Segalla LANCE VERMEULEN RE, INC

  1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
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  /38

  $399,999

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft

  123 Lower Rd, East Canaan, CT 06024

  This is an amazing opportunity to own a completely renovated home offering a private yard and a fabulous location! Step inside to a spacious living room that flows seamlessly into the dining area, creating the perfect space for entertaining. Just off the main living area is a versatile bonus room-ideal for a home office, playroom, or first-floor guest bedroom. The first floor also features a

  Lauren Freedman Coldwell Banker Realty

  123 Lower Rd, East Canaan, CT 06024
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  /30

  $1,200,000

  • Land
  • 13 Acres
  • $91,954 per Acre

  215 Taconic Rd, Salisbury, CT 06068

  It's rare to find property on a lake that is secluded and private and still be five minutes away from the local village with all the conveniences you want. It's extremely rare to find such a property that's also 13 acres. Lastly, to find such a property with the house site cleared and all engineering completed, well, that's not just rare - it's next to impossible. This parcel is on Lake Washinee,

  David Mallison William Pitt Sotheby's Int'l

  215 Taconic Rd, Salisbury, CT 06068
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  /53

  $3,250,000

  • 4 Beds
  • 3.5 Baths
  • 3,459 Sq Ft

  232 Giberson Rd, Sheffield, MA 01257

  The Quarry - A One-of-a-Kind Berkshire Estate on 60 Private Acres!Singular, stunning, and secluded--the quarry pool at the heart of this 60-acre Berkshire estate is truly one of its kind: the culmination of geology, industry, and artistry. Carved into a reclaimed limestone quarry and framed by towering stone walls and a 16-foot waterfall, the quarry pool is a marvel in and of itself--equal parts

  Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  232 Giberson Rd, Sheffield, MA 01257
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  /9

  $139,000

  • Land
  • 6 Acres
  • $22,720 per Acre

  0 Amory Ln, Southfield, MA 01259

  Discover the perfect setting for your custom retreat on this expansive 6+ acre lot nestled on a tranquil cul-de-sac off a scenic Berkshire country road. Located in New Marlborough, with a small portion extending into Sheffield, this beautiful parcel offers endless possibilities for your vision. Enjoy the serenity of nature, the charm of rural living, and the potential for lovely views. Whether

  Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  0 Amory Ln, Southfield, MA 01259
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  /39

  $4,321,000

  • 5 Beds
  • 8 Baths
  • 5,005 Sq Ft

  65 Hammertown Rd, Salisbury, CT 06068

  The post-and-beam residence showcases soaring ceilings and expansive windows that frame the spectacular landscape while highlighting the architectural character throughout. Natural materials-including local woods, native stone, and artisanal steel elements-create a sophisticated dialogue between interior spaces and the surrounding countryside. The heart of the main level features a grand Great

  Elyse Morris Elyse Harney Real Estate

  65 Hammertown Rd, Salisbury, CT 06068
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  /10

  $119,000

  • Land
  • 1.45 Acres
  • $82,069 per Acre

  0 Bunce Rd Unit 245787, Sheffield, MA 01257

  Situated in a peaceful well-established neighborhood, and surrounded by a natural buffer of mature trees, this beautiful 1.45 acre lot is cleared and ready for construction. Underground phone, cable, and electric utilities are conveniently located right at the end of the roughed-in driveway. Percolation test was completed in 2023. This charming parcel is the last available building lot on this

  Vashti Poor LANCE VERMEULEN RE, INC

  0 Bunce Rd Unit 245787, Sheffield, MA 01257
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  /40

  $5,875,000

  • 4 Beds
  • 6.5 Baths
  • 6,100 Sq Ft

  102 S Shore Rd, Salisbury, CT 06068

  Seize the best value on Twin Lakes! Compare this stunning Salisbury estate to the recently sold 29 Morgan Lane and discover unparalleled luxury at an extraordinary price. Nestled on the tranquil shores of East Twin Lake, this masterpiece blends Adirondack charm with modern elegance, offering breathtaking views, grand living spaces, and exquisite craftsmanship. This home is a testament to

  David Mallison William Pitt Sotheby's Int'l

  102 S Shore Rd, Salisbury, CT 06068
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  /38

  $279,000

  • 2 Beds
  • 2 Baths
  • 1,659 Sq Ft

  52 Shunpike Rd, Southfield, MA 01259

  Attention investors!! Nestled on a peaceful 1-acre lot, this 2-bedroom, 2-bath Cape offers warmth, character, and SO MUCH OPPORTUNITY! A spacious kitchen with adjoining pantry and dining area provides plenty of room for gathering. The inviting living room features a chunky staircase, exposed beams and a brick hearth, perfect for a wood or pellet stove. The first floor includes a bedroom, laundry

  Chris LaPatin LAMACCHIA REALTY, INC

  52 Shunpike Rd, Southfield, MA 01259
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  /20

  $449,000

  • 3 Beds
  • 3 Baths
  • 6,420 Sq Ft

  355 Clayton Rd, Sheffield, MA 01222

  Opportunities and Potential abound. Set back on 6+- acres in Rural Ashley Falls. Presently Greenwoods Church, can now be yours to live and work from. The large bright and open main room is 42' x 70' with a concrete floor and forced air heat. Create the space you've envisioned for yourself and your business, the ideas are endless from continuing a place of worship, a grand home, a car collectors

  Mark Rosengren LANCE VERMEULEN RE, INC

  355 Clayton Rd, Sheffield, MA 01222
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  /11

  $795,000

  • Land
  • 18 Acres
  • $44,167 per Acre

  0 Bull Hill Rd, Sheffield, MA 01257

  OWNER FINANCING AVAILABLE! Eighteen acres on the quietest dirt road with its own exceptional landscape feature: a boulder-strewn, mossy-rocked cobble. The cobble bisects a flat three acre cleared field to the east, and a wooded forest with old stone wall remnants to the west. Live amongst the ancient spirits in whatever beautiful house you build. Fifteen wooded acres in Chapter 61A. Buyer to

  Kristin Clayborne WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  0 Bull Hill Rd, Sheffield, MA 01257
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  /30

  $345,000

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  179 S Main St, Sheffield, MA 01257

  Step back in time with this charming 1826 gem, nestled in the quiet village of Sheffield on Main Street. Featuring 3 bedrooms, 3 bathrooms, and a first-floor ensuite, this home offers classic simplicity and historical integrity. The screened-in porch is perfect for enjoying the peaceful surroundings, while the 1-car garage adds convenience. Untouched by modern trends, this property is a blank

  Tony Segalla LANCE VERMEULEN RE, INC

  179 S Main St, Sheffield, MA 01257
• 

  

  /43

  $414,900

  • 3 Beds
  • 1.5 Baths
  • 1,617 Sq Ft

  454 Sheffield Plain, Sheffield, MA 01257

  Beautifully restored New England Farmhouse located in the quaint town of Sheffield. Exterior features fresh paint, new vinyl windows, and a new roof. Stepping inside this home has retained most of the original wide-plank hardwood flooring that has been restored on the first and second levels. Throughout the first floor there are custom updates in the half bathroom with new ceramic tiles, a new

  Cory Evangelisto NOCHER REALTY

  454 Sheffield Plain, Sheffield, MA 01257
• 

  

  /25

  $478,900

  • 5 Beds
  • 2 Baths
  • 2,494 Sq Ft

  33 Granite Ave, Canaan, CT 06018

  Charming 5-Bedroom Village Colonial in the Heart of North Canaan Located in a desirable sidewalk neighborhood, this beautifully renovated Village Colonial combines classic charm with modern updates. The home features newly updated electrical and plumbing systems, replastered and lathed walls, freshly refinished main-level floors, all-new bathrooms, and a fully remodeled kitchen. Freshly painted

  Daniel Smith Raynard & Peirce Realty,LLC

  33 Granite Ave, Canaan, CT 06018

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