Homes for Sale near Undermountain Elementary School

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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

  Grace Golden EQUINE HOMES REAL ESTATE, LLC

  0 S Main St, Sheffield, MA 01257
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  /40

  $1,275,000

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

  1166 Rannapo Rd, Sheffield, MA 01257

  It's no wonder this property is the home of Berkshire county's oldest elm tree! The abundant sunshine & quietude would make anybody want to set down roots. This light filled home has wood floors throughout the main level. Kitchen has granite counters, pantry & large island. As part of the open floor plan there is a dining room and living room that opens to an expansive deck. The great room

  Grace Golden Equine Homes Real Estate, LLC

  1166 Rannapo Rd, Sheffield, MA 01257
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  /53

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 4,853 Sq Ft

  360 Brush Hill Rd, Sheffield, MA 01257

  Tucked away in the woods with access to Three Mile Pond, this contemporary home will leave you longing to return. With views from most rooms, the thoughtfully designed floor plan leaves little to be desired. The main living spaces include an inviting living room with a stone fireplace that opens to a screened porch, a cozy den/library, and a spacious great room with soaring ceilings, a grand

  Tony Segalla LANCE VERMEULEN RE, INC

  360 Brush Hill Rd, Sheffield, MA 01257
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  /59

  $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

  $1,095,000

  • 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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  /20

  $1,229,000

  • 4 Beds
  • 4 Baths
  • 2,322 Sq Ft

  97 Brush Hill Rd, Great Barrington, MA 01230

  Berkshires Sanctuary - A Fully Renovated Retreat with Appalachian Trail Access & Nearby Three Mile Pond.Tucked away in a landscape of towering trees and rolling hills, this exquisite four-bedroom and three-bathroom, retreat has been reimagined with over $650,000 in premium renovations, offering the perfect balance of luxury and nature. With direct access to Appalachian trail and Three Mile Pond,

  Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  97 Brush Hill Rd, Great Barrington, MA 01230
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  /61

  $2,500,000

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

  1373 Boardman St, Sheffield, MA 01257

  The ULTIMATE LIVE-WORK-PLAY RETREATStep onto a property as striking as the Berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''The Factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1373 Boardman St, Sheffield, MA 01257
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  /52

  $998,000

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

  856 Barnum St, Sheffield, MA 01257

  Welcome to 856 Barnum, a stunning residence born from the creative vision of a talented photographer and acclaimed New York architect, Debora K. Reiser. What was once a modest Cape Cod has been transformed into a sophisticated modern masterpiece.The exterior showcases sleek lines and elegant copper details, with a striking turret adding depth to its profile. Upon entering, you are greeted by a

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  856 Barnum St, Sheffield, MA 01257
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  /39

  $695,000

  • 3 Beds
  • 1.5 Baths
  • 2,802 Sq Ft

  40 Main St, Egremont, MA 01258

  This colonial is the perfect representation of New England charm, offering a unique opportunity to experience the character of yesteryears while enjoying modern living in the heart of historic South Egremont. The inviting layout of the first floor features a spacious, open living area that seamlessly flows into a well-appointed kitchen, perfect for entertaining. A designated office space, half

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  40 Main St, Egremont, MA 01258
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  /33

  $595,000

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft

  115 Brush Hill Rd, Great Barrington, MA 01230

  Contemporary Design on Six Private Acres in Great Barrington!115 Brush Hill Road - a design-forward turnkey retreat in one of the Berkshires' most coveted areas.This post-mid-century contemporary blends natural materials, clean lines, and a light-filled layout with its serene, wooded surroundings.At the heart of the home is a soaring vaulted living room with exposed wood, skylights, and

  Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  115 Brush Hill Rd, Great Barrington, MA 01230
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  /31

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 2,008 Sq Ft

  95 Main St, Sheffield, MA 01257

  Beautiful Colonial right in the Village Center with acircular driveway and ample parking. Enter to an open kitchen and dining area with exposed beams, gracious living room with walls of windows and a family room with bar, custom stone flooring and fireplace. Convenient access from the family room to the back patio for grilling and entertaining with an exterior fireplace! The 2nd level features

  Cortney Dupont COHEN & WHITE ASSOCIATES

  95 Main St, Sheffield, MA 01257
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  /62

  $715,000

  • 3 Beds
  • 3 Baths
  • 2,395 Sq Ft

  649 Hewins St, Sheffield, MA 01257

  This special property has been thoughtfully renovated to preserve its antique farmhouse charm. Set on an open 1-acre lot along a pastural country road and shaded by a stately maple tree, this home exudes that timeless vintage character that is so rare to find. Step through the rustic pine door onto the brick floor of the white washed pine-paneled mudroom. Upon entering the bright kitchen, you may

  Vashti Poor LANCE VERMEULEN RE, INC

  649 Hewins St, Sheffield, MA 01257
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  /40

  $400,000

  • 5 Beds
  • 2 Baths
  • 2,485 Sq Ft

  254 Main St, Sheffield, MA 01257

  Welcome the historic Foxdale and the opportunity to own a piece of history that begins before the declaration of independence. This property originally was built in the 1750s. If a house with character is what you're looking for, look no further! In the heart of the village of Sheffield, you will find this property unlike any other. After its complete restoration by its visionary new owner this

  Cortney Dupont COHEN & WHITE ASSOCIATES

  254 Main St, Sheffield, MA 01257
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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

  $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

  119 S Main St, Sheffield, MA 01257
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  /33

  $495,000

  • 2 Beds
  • 1 Bath
  • 1,700 Sq Ft

  1291 Ashley Falls Rd, Sheffield, MA 01222

  Nestled in the charming village of Ashley Falls, this cozy single-level home offers a perfect blend of comfort and scenic beauty. The open floor plan includes 2 bedrooms, 1 bath, an eat-in kitchen, and a spacious living room with a wood-burning fireplace, large picture windows, and direct access to a screened porch overlooking acres of picturesque farmland. Additional features include a slab

  Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  1291 Ashley Falls Rd, Sheffield, MA 01222
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  /68

  $4,290,000

  • 4 Beds
  • 4.5 Baths
  • 5,800 Sq Ft

  113 Brush Hill Rd, Great Barrington, MA 01230

  THE GOAT......This exceptional Berkshire minimalistic sensation has been architecturally designed to maximize the open floor plan concept while being mindful of private work/play spaces. A showpiece with 12+ acres of privacy surrounds you while the panoramic western views in every season bring you peace and calmness. The walls of glass integrate nature and the tranquil spellbinding views with

  Mary Jane White COHEN & WHITE ASSOCIATES

  113 Brush Hill Rd, Great Barrington, MA 01230
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  /45

  $299,000

  • 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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  /5

  $1,500,000

  • Land
  • 123 Acres
  • $12,234 per Acre

  685B S Egremont Rd, Great Barrington, MA 01230

  122+ Acres of Land in Egremont & Sheffield Only. Over 700 feet of frontage on Sheffield-Egremont Rd on the Egremont / Sheffield Border. Former use as Golf Course for the Egremont Country Club. *Does not include any acreage in Great Barrington. See MLS # 241894 for the full parcel of 225 Acres.

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  685B S Egremont Rd, Great Barrington, MA 01230
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  /20

  $549,000

  • 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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  /4

  $69,000

  • Land
  • 3.72 Acres
  • $18,548 per Acre

  0 Greenwood Cir, Egremont, MA 01230

  Bring your creativity to build a sweet home with views of Smiley's Pond in this lovely quiet neighborhood. 3.72 acres on private drive close to the village center of South Egremont. Frontage on both Greenwood Circle and North Undermountain Road.

  Lance Vermeulen LANCE VERMEULEN RE, INC

  0 Greenwood Cir, Egremont, MA 01230
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  /21

  $325,000

  • 4 Beds
  • 1 Bath
  • 1,704 Sq Ft

  1114 County Rd, Great Barrington, MA 01230

  1950's Cape on 7.5 acres along a country road. This 4 bedroom home has a main floor with nice size kitchen, dining room, living room with fireplace, 2 bedrooms and a full bath. Upstairs there are two more bedrooms and a small office and good attic storage. Screened in porch off the living room, wood floors and beautiful yard. Roof is old (estimate attached in docs), Title V failed and seller is

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  1114 County Rd, Great Barrington, MA 01230
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  /11

  $795,000

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

  0 Bull Hill Rd, Sheffield, MA 01257

  Eighteen acres on the quitest 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.

  Martha Piper WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  0 Bull Hill Rd, Sheffield, MA 01257
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  /6

  $175,000

  • Land
  • 2.50 Acres
  • $70,000 per Acre

  0 The Ave, Egremont, MA 01230

  Terrific low real estate tax Egremont location. Close to the center of town, the Catamount Ski Area, and very nice restaurants and shopping. Great land value.

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  0 The Ave, Egremont, MA 01230
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  /93

  $4,200,000

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

  662 Brewer Hill Rd, New Marlborough, MA 01230

  Discover unparalleled luxury and serenity in this extraordinary 5-BR, 7-BA estate nestled in the heart of New Marlborough. Spanning over 6,000 square feet, this stunning residence is set on expansive grounds, 70+ acres, featuring a harmonious blend of wooded areas, open fields & distant mountain views. Designed by renowned architect Allan Shope, this architectural masterpiece is an uplifting

  Claire Pollart LANCE VERMEULEN RE, INC

  662 Brewer Hill Rd, New Marlborough, MA 01230
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  /12

  $299,000

  • Land
  • 4.10 Acres
  • $72,927 per Acre

  0 Pinecrest Hill Rd, Egremont, MA 01230

  Precious 4 acre parcel along Pine Crest Hill Rd with due diligence in place for a curb cut off of Undermountain Rd (Rte 41) a short distance from So. Egremont, with its quaint New England village charm. Potential for open and elevated views; (thinkglorious sunsets!) overlooking Smiley's (Mill) Pond. Perfect for walking and enjoying nature on Pine Crest Hill. This surveyed parcel is not part of

  Thomas Doyle, Sr. BISHOP WEST REAL ESTATE

  0 Pinecrest Hill Rd, Egremont, MA 01230
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  /9

  $199,000

  • Land
  • 1.30 Acres
  • $153,077 per Acre

  1699 N Main St, Sheffield, MA 01257

  COMMERCIAL AREA ON THE SHEFFIELD/GREAT BARRINGTON LINE OFF OF BUSY ROUTE 7. SOME WETLANDS BUT A WORTHY LOCATION. NICE WITH LEVEL LAWN. THERE ARE NOT MANY LOTS LEFT ALONG THIS POPULAR COMMERCIAL CORRIDOR.

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  1699 N Main St, Sheffield, MA 01257
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  /53

  $725,000

  • 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

  64 Hewins St, Sheffield, MA 01257
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  /30

  $369,000

  • 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
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  /43

  $430,000

  • 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
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  /21

  $220,000

  • 2 Beds
  • 1 Bath
  • 1,096 Sq Ft

  339 Clayton Rd, Sheffield, MA 01222

  Fantastic Opportunity to own in well established South Berkshire neighborhood. This homes good bones and newer roof make it a perfect candidate for a fresh makeover. Level 1 acre lot and oversized 2 car garage !

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  339 Clayton Rd, Sheffield, MA 01222
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  /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
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  /10

  $329,000

  • Land
  • 9 Acres
  • $37,860 per Acre

  10 Mountain Rd, Mount Washington, MA 01258

  RARE OPPORTUNITY. Private parcel with open views potential, atarting from the idyllic cul-de-sac, on Mountain Rd. in Mt. Washington, MA. This exclusive, private land parcel has 8.69 level and gently rolling acres.: Septic Field has been partially installed, Well has been drilled , and rough driveway installed. Fiber Optic is available. The plans for 4BR+4BA house with an in-law suite have been

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  10 Mountain Rd, Mount Washington, MA 01258
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  /41

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,152 Sq Ft

  163 Main St, Sheffield, MA 01257

  Built in 1802, this delightful 3-bedroom home is full of original details and charm. The 1st floor features two parlors with a double-sided fireplace, built-in bookcases, and a bay window with window seat perfect for curling up with a good book by the fire. French doors lead to a large open dining room and kitchen with granite countertops and cherry cabinets. Just off the kitchen is a cozy den

  Vashti Poor LANCE VERMEULEN RE, INC

  163 Main St, Sheffield, MA 01257
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  /32

  $499,000

  • 4 Beds
  • 2 Baths
  • 1,152 Sq Ft

  127 Old Joe Rd, Great Barrington, MA 01230

  PERFECT ONE LEVEL LIVING! Great location, 4 Bedrooms & Two Full Baths! This well maintained Ranch is a compact and efficient layout. A large sunny Living Room with corner gas fireplace, and an open Kitchen/ Dining area that expands out to a private deck for your Summer entertaining and relaxing. Ample closets throughout, a Mud room entry, attached Garage, convenient 1st floor laundry. The

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  127 Old Joe Rd, Great Barrington, MA 01230
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  /5

  $297,000

  • Land
  • 36 Acres
  • $8,303 per Acre

  0 County Rd, Sheffield, MA 01257

  Sheffield Woodland with Potential Views - Located off Bucolic County Road, just minutes from Sheffield Center this lovely 35.77-acre wooded parcel has a substantial elevation of over 1000 ft. The property is currently wooded with multiple hardwoods perfect for timbering to clear a home site. The property with clearing has south and western exposure. The well-drained soil has been perc'd and will

  Elyse Morris ELYSE HARNEY REAL ESTATE

  0 County Rd, Sheffield, MA 01257
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  /63

  $5,900,000

  • 11 Beds
  • 10 Baths
  • 9,748 Sq Ft

  25 W Sheffield Rd, Great Barrington, MA 01230

  Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations

  Elyse Morris ELYSE HARNEY REAL ESTATE

  25 W Sheffield Rd, Great Barrington, MA 01230
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  /47

  $1,980,000

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

  1269 Clayton Mill River Rd, New Marlborough, MA 01259

  Escape to the serene countryside, where this stunning New England farmhouse beckons with its picturesque setting on 10 acres. This property boasts a pool, pool house, garage and barn, offering endless possibilities for enjoyment and relaxation. Step inside this beautifully renovated home(2017), where modern amenities blend seamlessly with classic charm. The 4 bedrooms and 3.5 baths provide ample

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1269 Clayton Mill River Rd, New Marlborough, MA 01259

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