Ashley Falls, MA Homes for Sale

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  /36

  $699,000

  $100K PRICE DROP

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

  48 Preston Ln, Salisbury, CT 06068

  Seller says BRING OFFERS! You can't beat this new low price! Enjoy a private setting with lake access to beautiful Lake Washinee and the opportunity to customize this home to fit your vision. The current layout features a spacious first-floor primary suite, plus a second bedroom on the lower level with its own exterior access. The expansive lower level offers tremendous potential and can be

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  48 Preston Ln, Salisbury, CT 06068
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  /24

  $540,000

  Open Sat 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft

  125 Lumbert Cross Rd, Southfield, MA 01259

  Enjoy the peace and privacy of country living on this spacious 1.75-acre property, beautifully set back from a quiet country road. The level backyard offers plenty of room to relax, entertain, and enjoy the outdoors, with established fruit trees, blueberry and raspberry bushes, a fire pit, and a deck overlooking the expansive yard. A hot tub adds the perfect touch for unwinding at the end of the

  

  Wendy Eichman

  RAYNARD AND PEIRCE REALTY LLC

  125 Lumbert Cross Rd, Southfield, MA 01259
• 

  

  

  /23

  $279,000

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  335 Norfolk Rd, East Canaan, CT 06024

  Built in 1910, this charming Colonial is currently configured as a two-family home, featuring a 2-bedroom apartment on the first floor and a 1-bedroom apartment on the second floor. With its flexible layout, the property could easily be converted back into a spacious single-family residence. The first floor offers a large country-style eat-in kitchen with a fireplace and pantry, a generous living

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  335 Norfolk Rd, East Canaan, CT 06024
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  /29

  $475,000

  Open Fri 3PM - 5PM

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  125 S Canaan Rd, Canaan, CT 06018

  Back on the market due to previous buyer being unable to move forward with the purchase. Perched above the main road for added privacy, this newly remodeled home combines timeless charm with modern updates throughout. Beautiful engineered hardwood floors flow seamlessly through the living spaces, creating a warm and inviting atmosphere. The spacious living and dining room features a striking

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  125 S Canaan Rd, Canaan, CT 06018
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  /10

  $345,000

  • Land
  • 37.44 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

  0 Old Turnpike Rd N, Canaan, CT 06018
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  /6

  $325,000

  • Land
  • 21.7 Acres
  • $14,977 per Acre

  0 Sisson Hill Rd Unit 248042, New Marlborough, MA 01230

  21.7 wooded acres on one of South County's ''best-kept-secret'' back country roads, yet just minutes away from Great Barrington, Sheffield and the bucolic villages of New Marlborough. Discover nature, privacy & a unique sense of peace on this rare piece of land. The land has been perc tested, seller will provide final survey prior to closing. Map in documents shows proposed new boundaries for

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  0 Sisson Hill Rd Unit 248042, New Marlborough, MA 01230
• 

  

  /19

  $299,000

  $50K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,637 Sq Ft

  1427 Canaan Southfield Rd, Southfield, MA 01259

  Charming cottage-style home that offers far more space than meets the eye! The first floor features a spacious kitchen with abundant cabinet storage, pantry space, and a newer gas range, along with a cozy office nook, dining room, living room, full bath, two bedrooms, laundry room, and an inviting den. Upstairs offers three additional rooms, including two bedrooms, providing flexible space for

  

  Wendy Eichman

  RAYNARD AND PEIRCE REALTY LLC

  1427 Canaan Southfield Rd, Southfield, MA 01259
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  /43

  $1,125,000

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  701 Rhoades & Bailey, New Marlborough, MA 01230

  Hidden at the end of a long winding drive, this wonderful three-story Greek Revival home was built in 2001 and sits on over 34 private acres. The main level offers a living room, dining room, kitchen, half bath and a screened porch. Upstairs are two bedrooms and a full bath - all with hardwood floors, while the walkout lower level serves as either a third bedroom or a den, along with the laundry

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  701 Rhoades & Bailey, New Marlborough, MA 01230
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  /32

  $915,000

  $14K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,875 Sq Ft

  1289 Canaan Southfield Rd, Southfield, MA 01259

  Situated on just over 1.6 acres in Southfield, this charming property offers access to a private tennis court, and pool through the homeowners'' association. It has been meticulously updated and is ready for immediate occupancy. The beautiful screened porch and newly constructed terraced stonework establish the home as a genuine indoor/outdoor Berkshire retreat. Enjoy views of a striking gully

  Holly Leibrock ELYSE HARNEY REAL ESTATE

  1289 Canaan Southfield Rd, Southfield, MA 01259
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  /68

  $949,000

  • 5 Beds
  • 5 Baths
  • 5,466 Sq Ft

  130 S Main St, Sheffield, MA 01257

  A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently located on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth and craftsmanship of another era. 16 rooms, 5 bedrooms, multiple baths and 4 fireplaces, the home features beautiful wide-board floors, period details,

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  130 S Main St, Sheffield, MA 01257
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  /39

  $274,999

  • 2 Beds
  • 1 Bath
  • 1,616 Sq Ft

  65 E Main St, Canaan, CT 06018

  Charming, stylish, and completely move-in ready! This beautifully remodeled 2-bedroom home in North Canaan offers 1,616 sq ft of bright, inviting living space filled with character and modern updates. Step inside to discover fresh finishes, contemporary touches, and a cozy fireplace that creates the perfect place to relax and unwind. Outside, enjoy a spacious 0.33-acre lot with a fenced

  Alex King Lock and Key Realty, Inc

  65 E Main St, Canaan, CT 06018
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  /40

  $1,050,000

  • 3 Beds
  • 2 Baths
  • 2,800 Sq Ft

  128 Rannapo Rd, Sheffield, MA 01257

  Privately set on just under 7 acres, this beautifully renovated home offers the perfect combination of tranquility, privacy, and convenience. A meticulously paved circular driveway leads through elegant, iron fencing to the level, beautifully landscaped property. The home offers approximately 2,800 square feet of thoughtfully updated living space, with 3 to 4 bedrooms and 2 full baths across two

  Suzann Ward HOUSATONIC REAL ESTATE

  128 Rannapo Rd, Sheffield, MA 01257
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  /65

  $1,595,000

  $355K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,404 Sq Ft

  415 Brewer Branch Rd, New Marlborough, MA 01259

  Set on 21.5 acres at the end of a long, winding private drive, this extraordinary residence is a true architectural gem--where art, landscape, and modern living converge. Originally designed by Robert McMahon and built by Lou Boxer and later reimagined through a contemporary project by Deborah Reiser of the award-winning RUR Architecture with Hird Design and Construction as the builder, the home

  Sheila Thunfors STONE HOUSE PROPERTIES, LLC

  415 Brewer Branch Rd, New Marlborough, MA 01259
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  /23

  $4,750

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

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

  Built in 2023, this beautifully appointed contemporary Colonial offers a fresh take on country living in a peaceful Southern Berkshire setting. Available unfurnished for a one-year lease, the home features four bedrooms and three-and-a-half baths, including a spacious first-floor primary suite. The light-filled, open floor plan is designed for comfortable everyday living and entertaining, with

  Allison Rada STONE HOUSE PROPERTIES, LLC

  18 Cross To Canaan Valley Rd, New Marlborough, MA 01259
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  /10

  $310,000

  • Land
  • 3.43 Acres
  • $90,379 per Acre

  471(3) Undermountain Rd, Salisbury, CT 06068

  This affordable lot is just under 3.5 acres in Salisbury. The only clearing that's needed is for a driveway off the main road and to open up a potential view to the Taconic Range to the west if desired. Otherwise this lot is wide open and flat. There are a few possibilities here for a homesite, so the prospects are wide open. There's plenty of room for a pool, a garage, a guest house - whatever

  Karen Grimaldi William Pitt Sotheby's Int'l

  471(3) Undermountain Rd, Salisbury, CT 06068
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  /27

  $449,000

  $30K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,765 Sq Ft

  107 S Main St, Sheffield, MA 01257

  The Hatfield House : A rare 1793 Sheffield antique offering a unique renovated live/work opportunity, move-in ready; the main residence blends historic character including a sealed basement, new 3 bedroom Septic.. A separate one-bedroom apartment with its own entrance provides income or guest flexibility.Set on 1.5 acres with protected wetland views, commercial/residential zoning allows

  Judi Panzano HOUSATONIC REAL ESTATE

  107 S Main St, Sheffield, MA 01257
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  /40

  $320,000

  $49K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,784 Sq Ft

  287 W Main St, Canaan, CT 06018

  Nestled on a level in-town lot, this classic Colonial offers timeless charm, solid construction, and endless potential. Featuring three bedrooms and beautiful hardwood flooring, the home provides a warm and inviting layout ready for your personal touch. The front porch is THE perfect seasonal place to unwind after a long day or start your day with coffee! The adorable galley kitchen with

  Suzie Larson Turning Point Realty, LLC

  287 W Main St, Canaan, CT 06018
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  /21

  $110,000

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

  730 Clayton Rd, Sheffield, MA 01222

  Set along A rural country Town road, this parcel is a mixture of lightly wooded flat ground adjacent to/with a bog which is home to a mixture of frogs, a heron or two and other 'seasonal' visitors. Of the 7.2+- acres (the parcels total size) approximately 2.5 acres is a mostly flat zone in within which a home could be located. While approved for same back around the turn of tis century, all

  Robin Leech Robinson Leech Real Estate

  730 Clayton Rd, Sheffield, MA 01222
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  /7

  $195,000

  • Land
  • 14.89 Acres
  • $13,096 per Acre

  0 Trescott Hill Rd, North Canaan, CT 06018

  Located along a serene country road, this 14.89-acre plot of undeveloped land in East Canaan offers both seclusion and convenient proximity to town. The property abuts other expansive tracts of land and features diverse topography, including a readily accessible open field, wooded areas for privacy, and picturesque wetlands. An existing access road facilitates navigation and exploration of this

  Holly Leibrock Elyse Harney Real Estate

  0 Trescott Hill Rd, North Canaan, CT 06018
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  /6

  $1,750

  • 1 Bed
  • 1 Bath

  150 Water Farm Rd, Sheffield, MA 01257

  Terrific One Bedroom Garage Apartment in Sheffield. Nice neighborhood. You pick it; furnished or unfurnished. Minimum Lease Period is six (6) months.

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  150 Water Farm Rd, Sheffield, MA 01257
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  /30

  $649,000

  • 5 Beds
  • 3 Baths
  • 2,710 Sq Ft

  6 Redwood Ln, Sheffield, MA 01257

  A compelling multi-family opportunity in move-in condition, offering comfortable living space with the added flexibility of rental income or accommodations for extended family. The property also features a barn and access to a nearby pond for fishing and kayaking. Sheffield Center is approximately two miles away, offering local restaurants, the Bushnell-Sage Library, the Sheffield Historical

  Timothy Wighton STONE HOUSE PROPERTIES, LLC

  6 Redwood Ln, Sheffield, MA 01257
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  /22

  $595,000

  • 2 Beds
  • 2 Baths
  • 1,362 Sq Ft

  149 Rocky Ln, Salisbury, CT 06068

  The Cub House Located in the coveted Twin Lakes area of Salisbury, The Cub House is all about possibility. Set on nearly six acres along a quiet gravel road, this property offers an ideal address, beautiful natural surroundings, and the chance to either improve the existing It features a functional layout with a comfortable kitchen that opens into a large living and dining room with a fireplace.

  Elvia Gignoux William Pitt Sotheby's Int'l

  149 Rocky Ln, Salisbury, CT 06068
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  /7

  $299,000

  $50K PRICE DROP

  • Land
  • 19.73 Acres
  • $15,155 per Acre

  0 Hayes Hill Rd Unit 247870, New Marlborough, MA 01244

  Just shy of 20 acres. Make your way to the top for views, you won't be disappointed. An abundance of wildlife, and not a building in sight. Come take a look and make this your Berkshire retreat!

  Lawrence Reilly THE KINDERHOOK GROUP

  0 Hayes Hill Rd Unit 247870, New Marlborough, MA 01244
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  /30

  $673,000

  $22K PRICE DROP

  • 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

  Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

  1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
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  /72

  $1,185,000

  Open Sat 11AM - 1PM $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  249 Boardman St, Sheffield, MA 01257

  Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the

  Claudia Laslie WILLIAM RAVEIS - BERKSHIRE

  249 Boardman St, Sheffield, MA 01257
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  /55

  $549,000

  $100K PRICE DROP

  • 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

  Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

  168 Main St, Sheffield, MA 01257
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  /17

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft

  1415 Canaan Southfield Rd, Southfield, MA 01259

  3 BR 2 Bath Home with tons of storage and lots of space. Great opportunity for a small homestead or someone looking for a home with shope space and outbuilding. BEING SOLD AS IS

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  1415 Canaan Southfield Rd, Southfield, MA 01259
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  /26

  $429,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,258 Sq Ft

  689 N Main St, Sheffield, MA 01257

  Completely renovated and exceptionally versatile, this spacious 3-bedroom ranch is located in desirable Sheffield, MA. Set on a .50-acre commercially zoned lot just a 5 minute drive to downtown GB, the property offers outstanding live/work, investment, or business potential.The 2,258 sq. ft. main residence features 3 spacious bedrooms, a large new kitchen, full bath, washer/dryer, and

  Judi Panzano HOUSATONIC REAL ESTATE

  689 N Main St, Sheffield, MA 01257
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  /15

  $875,000

  • Land
  • 9.77 Acres
  • $89,560 per Acre

  471(2) Undermountain Rd, Salisbury, CT 06068

  This is one of the most stunning medium-sized land parcels in NW Connecticut. It's primarily an open field, part of a horse farm, with a tree lined entrance and a 180 degree view of the Taconic mountain range from south to north. Set well off the main road, the building site is relatively flat, with an attractive fence at the perimeters. It's a blank canvas waiting for the right buyer with vision

  Karen Grimaldi William Pitt Sotheby's Int'l

  471(2) Undermountain Rd, Salisbury, CT 06068
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  /40

  $1,700,000

  New Construction $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,480 Sq Ft

  26 Preston Ln, Salisbury, CT 06068

  This newly constructed 4 bedroom 3.5 bath 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 with seamless vantage points to take in the natural beauty of the out-of-doors. Fresh timbered beams, two story windows, solid white oak floors, solid hemlock & mahogany doors,

  Brenda McLean William Pitt Sotheby's Int'l

  26 Preston Ln, Salisbury, CT 06068
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  /36

  $1,995,000

  $280K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,933 Sq Ft

  7 Cooper Hill Rd, Salisbury, CT 06068

  The Ultimate Entertainer's Estate! If your life centers around fine food, close friends, and effortless hosting, this custom country estate is your dream destination. The true heart of this expanded 3,933 sq. ft. home is a jaw-dropping chef's kitchen featuring double islands, premium stainless-steel appliances, a dry double-fridge bar, and a hidden walk-in pantry. This culinary masterpiece

  Elyse Morris Elyse Harney Real Estate

  7 Cooper Hill Rd, Salisbury, CT 06068
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  /75

  $2,875,000

  $375K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 3,416 Sq Ft

  651 Hayes Hill Rd, New Marlborough, MA 01230

  OFFERED FULLY FURNISHED AND TURNKEY. Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  651 Hayes Hill Rd, New Marlborough, MA 01230
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  /40

  $799,000

  $90K PRICE DROP

  • 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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  /30

  $1,135,000

  • 4 Beds
  • 3.5 Baths
  • 2,460 Sq Ft

  35 Emmons Ln, Canaan, CT 06018

  CANAAN VALLEY HOME WITH POOL & STUDIO Indulge in Litchfield County luxury at this homestead, proudly situated in Canaan Valley, offering picturesque views of fields from both the front and back of this 4-Bedroom, 3-Bath residence, plus a Studio with its own Half Bath. This property features a spacious single-level living home, a separate studio, and an inground pool. The home has undergone

  Holly Leibrock Elyse Harney Real Estate

  35 Emmons Ln, Canaan, CT 06018
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  /9

  $650,000

  • Land
  • 7.25 Acres
  • $89,655 per Acre

  471(4) Undermountain Rd, Salisbury, CT 06068

  Imagine building your new home on a 7 acre lot in the very northwest corner of CT with a mountain view. It's less than 10 minutes to the town center of Salisbury, and less than half a mile to the Massachusetts border, which means that you're only a little more than 15 minutes to the happening town of Great Barrington. The lot features a picturesque rock outcrop in the middle (some clearing

  Karen Grimaldi William Pitt Sotheby's Int'l

  471(4) Undermountain Rd, Salisbury, CT 06068
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  /39

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  136 Lower Rd, East Canaan, CT 06024

  Blackberry River Oasis! With 1,100 feet of frontage on the Blackberry River and thousands of acres of protected state land as its backdrop, Stirling Farm offers a rare sense of privacy and tranquility. Cross a charming bridge with views of historic Beckley Furnace and its rushing spillway, then follow a private drive to a circa 1890 farmhouse nestled in a sunlit meadow. The home offers 3

  Elisa Waysenson Elyse Harney Real Estate

  136 Lower Rd, East Canaan, CT 06024
• 

  

  /26

  $649,000

  • 4 Beds
  • 1.5 Baths
  • 3,708 Sq Ft

  76 S Canaan Rd, Canaan, CT 06018

  Historic 1762 Farmhouse - Rare Restoration Opportunity Bring your vision to life with this authentic 1762 New England farmhouse, rich in history and full of untapped potential. This 4-bedroom home offers a unique opportunity for restoration, blending original character with the chance to create something truly your own. Featuring classic colonial architecture, the home showcases solid structural

  Arlene Gonzalez The Gonzalez Property Group

  76 S Canaan Rd, Canaan, CT 06018
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  /70

  $3,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,413 Sq Ft

  1015 Sisson Hill Rd, New Marlborough, MA 01230

  As seen in Architectural Digest, this meticulously reimagined 1875 farmhouse compound unfolds across 11.5 lush acres on a quiet, bucolic dead-end country road, with protected views. Brought to life in collaboration with AD100 design firm Sachs Lindores and landscape design by Judy Murphy, the property is full of historic character with refined modern comfort. The compound includes a four-bedroom,

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  1015 Sisson Hill Rd, New Marlborough, MA 01230
• 

  

  /65

  $2,095,000

  $55K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,461 Sq Ft

  304 Hickey Hill Rd, Sheffield, MA 01257

  This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added.Step inside to find timeless Colonial charm--exposed beams, three original fireplaces, and

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  304 Hickey Hill Rd, Sheffield, MA 01257
• 

  

  /52

  $1,900,000

  • 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

  1269 Clayton Mill River Rd, New Marlborough, MA 01259

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