Berkshire, MA Homes

$295,000 Sold Feb 28, 2025
- 1,900 Sq Ft
- $155/SF
- 97 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1845
10 Railroad St, Canaan, CT 06018

Updated North Canaan Investment - This charming two-unit building on Railroad Street in North Canaan has been fully updated and is currently rented and income-generating. The main level features large windows overlooking the sidewalk district allowing for excellent visibility and easy access for pedestrians. Sunlight fills the main floor from both the front and back of the building offering a

Liza Reiss Elyse Harney Real Estate

10 Railroad St, Canaan, CT 06018

/19
Est $345,713 Not Listed For Sale
- 2 Beds
- 1 Bath
- 700 Sq Ft
358 Mill River Southfield Rd, New Marlborough, MA 01230

358 Mill River Southfield Rd, New Marlborough, 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
/19
$385,000 Sold Feb 28, 2025
- 1,600 Sq Ft
- $241/SF
- 122 Days On Market
- 3 Beds
- 2 Baths
- Built 1977
350 S Undermountain Rd, Sheffield, MA 01257

This 3 bedroom 2 bath home tucked away in the peaceful woods of Berkshire County is perfect for someone who is looking to be close to town, but also looking for privacy. A screened in porch alongside the spacious deck allows for maximum opportunity to engage with nature. Located minutes to both the Appalachian Trail and Great Barrington.

Adam Dingman BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

350 S Undermountain Rd, Sheffield, MA 01257

/25
Est $363,331 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,256 Sq Ft
162 Hadsell St, New Marlborough, MA 01230

162 Hadsell St, New Marlborough, MA 01230

/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
$475,000 Sold Feb 28, 2025
- 2,162 Sq Ft
- $220/SF
- 195 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1986
15 Marilyn Dr, Canaan, CT 06018

A Charming Colonial with Scenic Views Welcome to this beautifully maintained 8-room colonial, a perfect blend of comfort and convenience, nestled on a picturesque corner lot. This inviting home offers a spectacular newly renovated kitchen, 4 bedrooms and 2.5 baths. a spacious living room that opens to a generous deck perfect for enjoying the quiet surroundings and open views.

John Harney William Pitt Sotheby's Int'l

15 Marilyn Dr, Canaan, CT 06018

/27
Est $262,589 Not Listed For Sale
- 3 Beds
- 1 Bath
- 988 Sq Ft
205 Lumbert Cross Rd, Southfield, MA 01259

205 Lumbert Cross Rd, Southfield, MA 01259

/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
$240,000 Sold Feb 12, 2025
- 1,888 Sq Ft
- $127/SF
- 93 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1968
4 Highland Ln, Canaan, CT 06018

Built in 1968, this house boasts a timeless charm with its original wood trim and detailing. The eat-in kitchen is perfect for whipping up family meals, while the dining room provides more space for those special occasions. Cozy up in the family room, complete with a raised hearth brick fireplace and eye-catching beamed ceiling - it's like a warm hug on a chilly evening! Flexibility is the name

Roberta Green Elyse Harney Real Estate

4 Highland Ln, Canaan, CT 06018

/43
Est $659,930 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,988 Sq Ft
422 Clayton Mill River Rd, New Marlborough, MA 01230

422 Clayton Mill River Rd, New Marlborough, MA 01230

/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
/25
$565,000 Sold Jan 24, 2025
- 1,850 Sq Ft
- $305/SF
- 0 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1928
210 Ashley Falls Rd, Sheffield, MA 01222

Renovated country home with distant mountain views.

Comparable Listing COMPARABLE LISTING ONLY

210 Ashley Falls Rd, Sheffield, MA 01222

/16
Est $365,124 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,172 Sq Ft
77 Clayton Mill River Rd, New Marlborough, MA 01230

77 Clayton Mill River Rd, New Marlborough, MA 01230

/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
$3,300,000 Sold Jan 23, 2025
- 5,116 Sq Ft
- $645/SF
- 98 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2022
88 Hammertown Rd, Salisbury, CT 06068

Rare New Construction with Major Western & Big Sky Views. 4 Bedrooms, 4.5 Baths with an Open Floor-plan & Modern Edge, this Property is Unmatched. Main Level Primary Bedroom with Large Closet & Full Bath. 3 En-Suite Bedrooms Up Share Family Room with Gas Fireplace & Monster Views. Large Refined Eat-in Kitchen. Screened Porch. Private Office. 6.28 +/- Pastoral Acres in the Coveted Taconic Area

Graham Klemm Klemm Real Estate Inc

88 Hammertown Rd, Salisbury, CT 06068

Est $270,509 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,506 Sq Ft
59 Foote Ave, Canaan, CT 06018

59 Foote Ave, Canaan, CT 06018

/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
$340,000 Sold Jan 22, 2025
- 1,452 Sq Ft
- $234/SF
- 67 Days On Market
- 3 Beds
- 1 Bath
- Built 1959
241 E Canaan Rd, East Canaan, CT 06024

First Time on the Market- Custom Ranch built by a well known builder. It has bold built-ins surrounding the beautiful fieldstone fireplace in the living room. This Turnkey, 3 Bedroom, 1 Bath ranch has character and is loaded with charm and craftmanship. The quality of this home is amazing. Beautiful views of Canaan Mountain and East Canaan Church. Located in the sought after Northwest Corner of

Chris KELL W. Raveis Lifestyles Realty

241 E Canaan Rd, East Canaan, CT 06024

Est $371,209 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,659 Sq Ft
72 Old Turnpike Rd, Canaan, CT 06018

72 Old Turnpike Rd, Canaan, CT 06018

/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
$258,000 Sold Jan 21, 2025
- 1,532 Sq Ft
- $168/SF
- 111 Days On Market
- 3 Beds
- 1 Bath
- Built 1877
16 Barlow St, Canaan, CT 06018

Welcome to 16 Barlow St, a delightful 3-bedroom, 1-bath colonial home nestled in the heart of picturesque Canaan. Built in 1877, this vintage gem exudes timeless charm while offering modern comforts for today's living. Outside, the charming front porch is ideal for watching the world go by, while the backyard provides a peaceful haven for gardening, playing, or simply enjoying the beauty of

Lisa McCarthy Coldwell Banker Realty

16 Barlow St, Canaan, CT 06018

Est $1,375,541 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,665 Sq Ft
293 Twin Lakes Rd, Salisbury, CT 06068

293 Twin Lakes Rd, Salisbury, CT 06068

/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
/3
$121,000 Sold Jan 17, 2025
- Land
- 20 Acres
- $6,148 per Acre
- 1620 Days On Market
Unlisted Address

COUNTRY LIVING. Nearly 20 wooded acres with 600' frontage on rural Water Farm Road. Also has frontage on East Road. Town water likely accessible. Electricity accessible on road. Property perced by White Engineering.

Tom Lynch COMPASS MASSACHUSETTS , LLC GB

Unlisted Address

Est $179,379 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 890 Sq Ft
70 Church St Unit D6, Canaan, CT 06018

70 Church St Unit D6, Canaan, CT 06018

/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
/72
$330,650 Sold Jan 17, 2025
- 1,770 Sq Ft
- $187/SF
- 122 Days On Market
- 4 Beds
- 2 Baths
- Built 1955
136 Clayton Rd, Ashley Falls, MA 01222

Enjoy life in the Southern Berkshires with everything it has to offer, only minutes to the CT/NY Borders. Located in the Village of Ashley Falls, this lovely Cape features four Bedrooms, two full Baths, fireplaced living room, a large four season sunroom that opens to an oversized patio style deck.In addition an attached garage with tiled breezeway and a large private yard.Only a short drive to

Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

136 Clayton Rd, Ashley Falls, MA 01222

Est $268,359 Not Listed For Sale
- 2 Beds
- 1 Bath
- 864 Sq Ft
4 Terry Ln, Canaan, CT 06018

4 Terry Ln, Canaan, CT 06018

/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
/36
$559,000 Sold Jan 16, 2025
- 1,400 Sq Ft
- $399/SF
- 144 Days On Market
- 3 Beds
- 2 Baths
- Built 2002
78 Ashley Falls Rd, Sheffield, MA 01257

Move right into this perfectly kept ranch-style home in picturesque Ashley Falls village. This inviting property sits on 2.5 flat acres and is conveniently located near most local amenities. Inside you will find an open floor plan flooded with natural sunlight featuring an en-suite primary with 2 additional bedrooms and laundry on the main floor - perfect for easy living. The large finished

Tony Segalla LANCE VERMEULEN RE, INC

78 Ashley Falls Rd, Sheffield, MA 01257

Not Listed For Sale
- 1 Bed
- 1 Bath
- 614 Sq Ft
5 Bloomer Ln, Salisbury, CT 06068

5 Bloomer Ln, Salisbury, CT 06068

/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
$560,000 Sold Jan 15, 2025
- 742 Sq Ft
- $755/SF
- 173 Days On Market
- 1 Bed
- 1 Bath
- Built 1984
1 Elman Dr, Salisbury, CT 06068

Discover the epitome of tranquility and charm with this cozy one bedroom one bath cottage, nestled on a sprawling 15.6-acre lightly wooded estate in the Twin Lakes area. The perfect retreat for those seeking simplicity and connection with the outdoors. Relax in front of the fireplace, or be enveloped by nature from the raised deck. As you meander through and explore the serene landscape, you'll

MICHAEL CONLOGUE William Pitt Sotheby's Int'l

1 Elman Dr, Salisbury, CT 06068

Est $250,280 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,109 Sq Ft
9 Lawrence Ave, Canaan, CT 06018

9 Lawrence Ave, Canaan, CT 06018

/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
$334,000 Sold Jan 10, 2025
- 1,092 Sq Ft
- $306/SF
- 34 Days On Market
- 3 Beds
- 1 Bath
- Built 1965
6 Housatonic Ave, Canaan, CT 06018

Mid Century mint ranch house within a bucolic North Canaan, CT neighborhood very close to Salisbury, CT, Falls Village, Great Barrington, MA and every regional amenity that this part of the CT Berkshires is celebrated for. Within the Litchfield County market here is an exceptional value as a starter home, downsizer, or co - primary residence for the busy digital nomad.

Andrew Gates Houlihan Lawrence

6 Housatonic Ave, Canaan, CT 06018

Est $294,169 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,320 Sq Ft
157 Church St, Canaan, CT 06018

157 Church St, Canaan, CT 06018

/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
$385,000 Sold Jan 06, 2025
- Land
- 3.79 Acres
- $101,583 per Acre
- 60 Days On Market
00 Taconic Rd, Salisbury, CT 06068

Embrace the Countryside on Taconic Rd: A Premier 3.78 Acre Estate Lot . Part of the esteemed Grassland Farm, this open and flat parcel boasts views to the Northwest, offering a picturesque backdrop for your future residence. Taconic Rd is synonymous with prestige and tranquility. Surrounded by high-caliber homes, your investment here is not just in land, but in a lifestyle of elegance and peace

John Harney William Pitt Sotheby's Int'l

00 Taconic Rd, Salisbury, CT 06068

Showing Results 81 - 120, Page 3 of 18

Massachusetts Berkshire County Ashley Falls

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