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Ashley Falls, MA Homes for Sale with Acreage

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  • /36

    $850,000

    • 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 with room for expansion, 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.

    Agent Photo

    Wendy Eichman

    Raynard & Peirce Realty,LLC

    (860) 792-5920

    48 Preston Ln, Salisbury, CT 06068
  • /35

    $495,000

    • 3 Beds
    • 2.5 Baths
    • 3,217 Sq Ft

    2105 S Undermountain Rd, Sheffield, MA 01257

    If you've been looking for a grand fixer-upper, this might be the property for you! Situated on the MA/CT line (house & 4.79 acres in MA, with 3.1 acres in CT bordering Sage's Ravine), the 1790's home has been partially updated and awaits the inspiration & vision of it's next owners. The first floor offers a large living room, parlor, dining room, semi-updated kitchen & modern full bath, large

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 393-2038

    2105 S Undermountain Rd, Sheffield, MA 01257
  • /53

    $645,000

    • 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
  • /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!

    Agent Photo

    Wendy Eichman

    Raynard & Peirce Realty,LLC

    (860) 609-6471

    0 Old Turnpike Rd N, Canaan, CT 06018
  • /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
  • /45

    $999,000

    • Land
    • 17 Acres
    • $57,779 per Acre

    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

    Grace Golden Equine Homes Real Estate, LLC

    1166 Rannapo Rd, Sheffield, MA 01257
  • /39

    $889,000

    • 3 Beds
    • 2.5 Baths
    • 1,866 Sq Ft

    1460 Ashley Falls Rd, Sheffield, MA 01257

    Immaculate contemporary home in Ashley Falls offering a perfect blend of modern design & natural surroundings. The 3-bedroom, 2.5-bath residence is bathed in natural light, creating an inviting & airy atmosphere.The heart of the home features a striking marble-faced fireplace, an elegant focal point for entertaining & relaxation. The thoughtfully designed floor plan flows seamlessly to outdoor

    Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    1460 Ashley Falls Rd, Sheffield, MA 01257
  • /40

    $895,000

    • 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
  • /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
  • /82

    $1,750,000

    • 4 Beds
    • 5 Baths
    • 4,492 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
  • /91

    $3,995,000

    • 5 Beds
    • 6.5 Baths
    • 6,915 Sq Ft

    662 Brewer Hill Rd, New Marlborough, MA 01230

    Iconic only begins to describe this rare union of sophistication & natural splendor. Spanning 40+ secluded acres of rolling meadows, forested trails, & sweeping mountain views, this remarkable estate has welcomed world-renowned artists & hosted unforgettable gatherings, from summer soirees to intimate retreats.At its heart is the Great House--a 6,000 sq. ft. architectural masterpiece by renowned

    Claire Pollart LANCE VERMEULEN RE, INC

    662 Brewer Hill Rd, New Marlborough, MA 01230
  • /52

    $1,900,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,976 Sq Ft

    1269 Clayton Mill River Rd, New Marlborough, MA 01259

    Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign--an escape where silence is broken only by the wind in the fields and the song of birds.The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of

    Lisa Hoe THE KINDERHOOK GROUP - PITTSFIELD

    1269 Clayton Mill River Rd, New Marlborough, MA 01259
  • /53

    $875,000

    • 4 Beds
    • 2.5 Baths
    • 2,452 Sq Ft

    1872 S Undermountain Rd, Sheffield, MA 01257

    This 4 Bedroom, 2.5 Bath streamside retreat is tucked perfectly into an idyllic private setting, just the spot to let those cares go. Thoughtfully updated in 2022, with nature out every window, the comfortable blend of public and private spaces is convenient for any use.. With exposed beams, walls of windows, a spiral staircase, main floor bedrooms and baths, mini split a/c units, garden doors

    David Taylor ELYSE HARNEY REAL ESTATE

    1872 S Undermountain Rd, Sheffield, MA 01257
  • /40

    $2,400,000

    • 3 Beds
    • 2.5 Baths
    • 3,552 Sq Ft

    26 Preston Ln, Salisbury, CT 06068

    Shangra-Lodge, part of the allure where days spent approaches perfection. This newly constructed modern farmhouse in the Twin Lakes community enjoys shared access on Lake Washinee. The home's minimalist design melds simplicity with sophistication. Rooms are light filled and have seamless vantage points to take in the natural beauty of the out-of-doors. Fresh timbered beams, two story windows,

    Brenda McLean William Pitt Sotheby's Int'l

    26 Preston Ln, Salisbury, CT 06068
  • /4

    $325,000

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft

    1089 Canaan Southfield Rd, Southfield, MA 01259

    An enchanting parcel of land with a 2 Bedroom Ranch, in need of significant updates and cosmetics. The land is beautiful, 5.59 acres, with the house nicely sited up on the knoll. So much potential! There is an attached garage and full basement.The septic design is available and estimate is in hand. Being sold ''as is'', will escrow funds for the septic. A worthwhile project in a private, natural

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    1089 Canaan Southfield Rd, Southfield, MA 01259
  • /63

    $730,000

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    461 Hulett Hill Rd, Sheffield, MA 01257

    Views galore define this Sheffield gem, situated on 1.4 acres overlooking rolling pastures, hills, and a winding stream. Built in 1990, the home exudes Shaker charm with wide plank wood floors and special touches throughout. First floor features sunny living room with wood burning fireplace and peek-a-boo TV cabinet, farm kitchen/dining area off expansive deck, powder room, boot room entry, and

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    461 Hulett Hill Rd, Sheffield, MA 01257
  • /15

    $599,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    2170 Canaan Southfield Rd, Southfield, MA 01259

    Located in the desirable Clayton section of New Marlborough, this 3-bedroom, 2-bath home offers a rare opportunity to own 7.2 acres with 383 feet of frontage on the Konkapot River. The property features a natural setting with direct river access and plenty of room to make it your own.The home has a functional layout with three bedrooms and two full baths. While move-in ready, it would benefit

    Freddy Friedman BIRCH PROPERTIES

    2170 Canaan Southfield Rd, Southfield, MA 01259
  • /2

    $63,900

    • Land
    • 3.00 Acres
    • $21,300 per Acre

    0 Alum Hill Unit 73415610, Sheffield, MA 01257

    OWNER FINANCING AVAILABLE! This 3.00-acre wooded parcel in peaceful Sheffield, MA offers the perfect setting for your Berkshires retreat or year-round home. Surrounded by natural beauty, you'll enjoy nearby attractions like Bartholomew’s Cobble, the Appalachian Trail, and the cultural gems of Great Barrington just minutes away. Sheffield is known for its small-town charm, farm-to-table dining,

    Derek Greene The Greene Realty Group

    0 Alum Hill Unit 73415610, Sheffield, MA 01257
  • /34

    $795,000 Open Sat 12:30PM - 2:30PM

    • 3 Beds
    • 3 Baths
    • 1,991 Sq Ft

    483 Home Rd, Great Barrington, MA 01230

    A Berkshire dream home! Nestled in a quiet private setting to enjoy the outdoors. This 3 bedroom 3 full bath home is empty and ready to go. Great lighting nice open kitchen dining/living area. Additional room can be used as a den or 1st floor bedroom. Wood stove insert for chilly fall nights while enjoying your 3 seasoned screened porch. Oversized 2 car garage. Full basement could be completed as

    Suzann Ward HOUSATONIC REAL ESTATE

    483 Home Rd, Great Barrington, MA 01230
  • /25

    $795,000

    • 3 Beds
    • 2 Baths
    • 1,730 Sq Ft

    1427 Hewins St, Sheffield, MA 01257

    Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a local custom builder, this 3-bedroom, 2-bath home sits on 1.64 private acres. The open-concept living, dining, and kitchen area flows seamlessly to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful

    Claire Pollart LANCE VERMEULEN RE, INC

    1427 Hewins St, Sheffield, MA 01257
  • /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
  • /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
  • /26

    $699,000

    • 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
  • /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
  • /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
  • /44

    $1,200,000

    • 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
  • /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
  • /70

    $895,000

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

    567 S Main St, Sheffield, MA 01257

    Investment opportunity in Sheffield. Versatile investment opportunity set on 11 private acres. This multi-building property, held by the same family for four decades, offers strong income potential with flexible configurations across three separate structures. Main House with (4) 1BR and (1) 2BR apartment, a second 3 BR home, and a three-bay garage. Just 15 minutes from GB and 10 minutes to

    Claire Pollart LANCE VERMEULEN RE, INC

    567 S Main St, Sheffield, MA 01257
  • /17

    $845,000

    • 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
  • /39

    $3,680,000

    • 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
  • /10

    $114,900

    • Land
    • 1.45 Acres
    • $79,241 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
  • /11

    $695,000

    • Land
    • 18 Acres
    • $38,611 per Acre

    0 Bull Hill Rd, Sheffield, MA 01257

    SIGNIFICANT PRICE REDUCTION! 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

    Kristin Clayborne WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    0 Bull Hill Rd, Sheffield, MA 01257
  • /17

    $359,900

    • 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
  • /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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