Homes for Sale near Undermountain Elementary School

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  /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

  

  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

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 481-1637

  119 S Main St, Sheffield, MA 01257
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  /69

  $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

  Lauren Molk ELYSE HARNEY REAL ESTATE

  25 W Sheffield Rd, Great Barrington, MA 01230
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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 made up

  Grace Golden Equine Homes Real Estate, LLC

  0 S Main St, Sheffield, MA 01257
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  /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
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  /52

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 2,742 Sq Ft

  22 Sheffield Rd, Great Barrington, MA 01230

  Discover this enchanting 1900s Town Colonial, where historic charm meets modern sophistication. Nestled in a tranquil neighborhood, this home offers four spacious bedrooms, two updated full baths, and a stunning chef's kitchen, blending comfort with style. From the moment you enter through the newly renovated mudroom, you'll appreciate the original wood floors and built-in shelving that preserve

  Suzann Ward HOUSATONIC REAL ESTATE

  22 Sheffield Rd, Great Barrington, MA 01230
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  /31

  $995,000

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft

  18 Creamery Rd, Great Barrington, MA 01230

  Nestled on 6.6 peaceful acres, this beautifully renovated country Cape offers exceptional privacy just minutes from town. Set well back from the road, the home enjoys a quiet, convenient location surrounded by mature trees and gardens.Inside, a spacious dining room features a striking stone fireplace, while the large living room showcases wood floors that extend throughout. Every detail has been

  Allison Rada STONE HOUSE PROPERTIES, LLC

  18 Creamery Rd, Great Barrington, MA 01230
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  /20

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft

  114 Brush Hill Rd, Great Barrington, MA 01230

  New Build Contemporary. Timbercraft Homes & Rosengren Architects collaborated to create this Contemporary 1584 square foot 2 bedroom home. Clean lines and simple one level living. Energy efficient Home with beautiful oak floors, custom kitchen open to dining and living room. Primary bedroom spacious and bright with well appointed bathroom and walk-in closet. Fireplace, dual fuel heating and AC. 1

  Mark Rosengren LANCE VERMEULEN RE, INC

  114 Brush Hill Rd, Great Barrington, MA 01230
• 

  

  /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
• 

  

  /20

  $1,162,000

  • 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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  /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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  /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
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  /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
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  /62

  $2,495,000

  • 5 Beds
  • 3.5 Baths
  • 6,254 Sq Ft

  84 Undermountain Rd, Egremont, MA 01230

  Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it

  Tony Segalla LANCE VERMEULEN RE, INC

  84 Undermountain Rd, Egremont, MA 01230
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  /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
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  /34

  $795,000

  • 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
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  /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 with a lovely backyard patio--perfect for indoor-outdoor living. Ideal for both outdoor enthusiasts, with hiking, biking, and skiing nearby or one could just enjoy

  Claire Pollart LANCE VERMEULEN RE, INC

  1427 Hewins St, Sheffield, MA 01257
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  /54

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 1,822 Sq Ft

  1862 Home Rd, Great Barrington, MA 01230

  Bordering large parcels of protected land, including the Appalachian Trail, this super-easy-to-maintain contemporary/split-level is in move-in condition. Nicely sited on one acre of land, offering a quiet location with privacy. The interior is light and bright, and the floor plan provides an efficient use of space with distinct gathering areas. The vaulted ceiling living room has a gas

  Lori Rose STONE HOUSE PROPERTIES, LLC

  1862 Home Rd, Great Barrington, MA 01230
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  /13

  $325,000

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  412 Berkshire School Rd, Sheffield, MA 01257

  1995 split level home on .50 acres walking distance to the village of Sheffield. 3 bedrooms 1 full bath....eat in kitchen, living room....unfinished lower level....electric and forced hot air propane fired heat, vinal siding......septic.(Title 5 completed)....private water company

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  412 Berkshire School Rd, Sheffield, MA 01257
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  /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
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  /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
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  /78

  $4,500,000

  • 4 Beds
  • 3 Baths
  • 5,256 Sq Ft

  381 Sheffield-Egremont Rd, Sheffield, MA 01257

  SPECTACULAR ONE OF A KIND BERKSHIRE PROPERTY! This compound includes an elegant and updated 4 bedroom 1759 Colonial home and fabulous RED BARN with 2 separate guest spaces. Mill pond for fishing, heated pool, patios and screen porch, 66 protected SUBDIVIDABLE ACRES...with views of Mount Washington. The perfect place to entertain friends and family. An incredible opportunity for additional

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  381 Sheffield-Egremont Rd, Sheffield, MA 01257
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  /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
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  /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
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  /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
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  /34

  $739,000

  • 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
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  /53

  $2,690,000

  • 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
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  /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
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  /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
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  /48

  $3,750,000

  • 4 Beds
  • 4.5 Baths
  • 5,300 Sq Ft

  116 Brush Hill Rd, Great Barrington, MA 01230

  Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout

  Mark Rosengren LANCE VERMEULEN RE, INC

  116 Brush Hill Rd, Great Barrington, MA 01230
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  /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
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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

  $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
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  /34

  $773,000

  • 3 Beds
  • 2.5 Baths
  • 3,082 Sq Ft

  86 Main St, Sheffield, MA 01257

  GRACIOUS IN-TOWN LIVING IN THE SOUTHERN BERKSHIRES 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

  David Taylor Elyse Harney Real Estate

  86 Main St, Sheffield, MA 01257
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  /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
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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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  /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
• 

  

  /11

  $795,000

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

  0 Bull Hill Rd, Sheffield, MA 01257

  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 acres in Chapter 61A. Buyer to

  Kristin Clayborne WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  0 Bull Hill Rd, Sheffield, MA 01257
• 

  

  /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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