35

Ashley Falls, MA Houses 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

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 296-3500

    64 Hewins St, Sheffield, MA 01257
  • /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

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 481-1637

    119 S Main St, Sheffield, MA 01257
  • /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

    Agent Photo

    Wendy Eichman

    Raynard & Peirce Realty,LLC

    (860) 295-3073

    182 Church St, Canaan, CT 06018
  • /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

    Agent Photo

    Wendy Eichman

    Raynard & Peirce Realty,LLC

    (860) 792-5920

    48 Preston Ln, Salisbury, CT 06068
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /82

    $1,750,000

    • 4 Beds
    • 5 Baths
    • 5,000 Sq Ft

    978 Clayton Mill River Rd, New Marlborough, MA 01259

    The Ephraim Chapin House, a.k.a the ''Landlord Abel House'' was built in Chicopee c. 1725. In 1979 this handsome home & tavern was dismantled and relocated to Southfield. There it was re-erected upon a new foundation atop a hill, where it now resides on a 51-acre estate straddling the banks of Konkapot River. Once the beloved retreat of an artist and a serious collector of early American art and

    Vashti Poor LANCE VERMEULEN RE, INC

    978 Clayton Mill River Rd, New Marlborough, MA 01259
  • /37

    $1,475,000

    • 1 Bed
    • 2 Baths
    • 1,296 Sq Ft

    481 Shunpike Rd, Sheffield, MA 01257

    A total 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own home with mountain views. A 36x52 work shop. One full time residence and a separate summer studio. Some land does go into New Marlborough. Surrounded by conservation land. Passive solar views facing South and West. Property has been a sculpture park for many years. Trails throughout. Views to Connecticut.

    Suzann Ward HOUSATONIC REAL ESTATE

    481 Shunpike Rd, Sheffield, MA 01257
  • /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
  • /39

    $1,275,000

    • 4 Beds
    • 5 Baths
    • 3,528 Sq Ft

    1669 Silver St, Sheffield, MA 01257

    Experience breathtaking panoramic vistas over protected land from every angle in this renovated Classic American Farmhouse. Nestled on two parcels, this residence boasts a pool, a detached garage, and gracious proportions throughout. Relax in the majestic long-range mountain vistas. The house is perfectly positioned to experience both sunrise and sunset views.Step inside to discover an

    Elyse Morris ELYSE HARNEY REAL ESTATE

    1669 Silver St, Sheffield, MA 01257
  • /17

    $364,900

    • 2 Beds
    • 2 Baths
    • 2,127 Sq Ft

    277 Ashley Falls Rd, Canaan, CT 06018

    A remarkable opportunity to combine residencial on the second floor with commercial on the main floor in an excellent location with plenty of private parking. The kitchen is set up for the discerning chef , a large dining room, a bedroom/office and living room with a propane fireplace completes the first floor. The gorgeous hardwood floors throughout the house have just been finished and the

    John Harney William Pitt Sotheby's Int'l

    277 Ashley Falls Rd, Canaan, CT 06018
  • /24

    $339,000

    • 6 Beds
    • 5.5 Baths
    • 3,683 Sq Ft

    175 Main St, Sheffield, MA 01257

    Come this charming 1820 colonial located in Downtown Sheffield! This unique property features 6 bedrooms and 5 and half bathrooms. Lovely hardwood showcasing wide plank and parquet style floors encompass 3,683 square feet of living space. Plenty of off street parking due to the oversized driveway and 2 car attached garage with loft space. Full, unfinished basement can provide additional storage

    Nicholas Decaro Property Works New England

    175 Main St, Sheffield, MA 01257
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