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Homes for Sale near Berkshire School

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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

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 481-1637

    119 S Main St, Sheffield, MA 01257
  • /69

    $5,650,000

    • 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
  • /8

    $2,150,000

    • 4 Beds
    • 2 Baths
    • 1,200 Sq Ft

    199 West St, South Egremont, MA 01258

    Rare Opportunity: 185 Acres of Natural Beauty in the Southern BerkshiresWe are offering one of the largest remaining privately owned parcels of natural acreage in the Southern Berkshires 185 private acres atop a mountain in Mount Washington, Massachusetts.Surrounded by protected forestland, this extraordinary property features over 10,000 feet of road frontage in a 3-acre zoning

    David Singer Mohonk Educational and Neuropsychological Foundation

    199 West St, South Egremont, MA 01258
  • /66

    $1,395,000

    • 4 Beds
    • 4.5 Baths
    • 3,185 Sq Ft

    124 Egremont Plain Rd, Great Barrington, MA 01230

    This beautiful home was built in 2006, and updated in 2022. The house is situated on just shy of 5 Acres in the town of Egremont. The home is flooded with sun all day, rarely needing a light on in the house. Direct access to the Green River at the edge of property to cool off on those hot summer days. A new central AC system was installed throughout home and apt A New backup generator, rain

    Lawrence Reilly THE KINDERHOOK GROUP

    124 Egremont Plain Rd, Great Barrington, MA 01230
  • /60

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft

    905 West Rd, Great Barrington, MA 01230

    Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road.

    William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    905 West Rd, Great Barrington, MA 01230
  • /37

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,256 Sq Ft

    414 S Undermountain Rd, Sheffield, MA 01257

    Custom modern home with open plan living area, high ceilings and oversized windows everywhere bringing in tremendous natural light. One level living with large gorgeous marble kitchen, great working island and wall pantry. Guest wing off entry with two bedrooms and a hall bath. Entry hall has a powder room, hooks for coats and closet. The primary suite, on the south side, has french doors to

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    414 S Undermountain Rd, Sheffield, MA 01257
  • /52

    $1,149,000

    • 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
  • /47

    $1,685,000

    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    9 Bott Hill Rd, Egremont, MA 01230

    Stunning Post and Beam Home with Log Facade. Nestled in a park-like setting with views of Mount Washington. Outdoor Amenities Galore. Extensive patios and wraparound decks provide the perfect venues for outdoor gatherings including a private bocce ball court, outdoor hot tub, and private dog park. The first floor offers generous entertaining spaces, including two to three bedrooms that provide

    Suzann Ward HOUSATONIC REAL ESTATE

    9 Bott Hill Rd, Egremont, MA 01230
  • /47

    $1,795,000

    • 4 Beds
    • 3 Baths
    • 2,686 Sq Ft

    24 Baldwin Hill Rd E, Egremont, MA 01230

    Located on one of Egremont's most picturesque roads, this beautifully designed contemporary home offers panoramic views from nearly every room. Set in a low-tax town just minutes from Great Barrington, this home is private, comfortable and versatile. The main house has perfect flow, great scale rooms, tons of light, a beautiful stone fireplace, custom Kitchen, and the prettiest of outdoor spaces.

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    24 Baldwin Hill Rd E, Egremont, MA 01230
  • /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
  • /29

    $965,000

    • 3 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    188 Hillsdale Rd, Egremont, MA 01230

    GORGEOUS LOW MAINTENANCE HOME IN LOW TAX EGREMONT. A move-in ready opportunity, just minutes to the NY & CT borders AND Great Barrington. This home is ready for occupancy just in time for Ski Season. Wonderful chef's kitchen with open plan Living/Dining. The upper level hosts a grand primary en- suite, with a dedicated office space and seating area, AND its own screened porch. Two additional

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    188 Hillsdale Rd, Egremont, MA 01230
  • /40

    $995,000

    • 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

    $1,049,000

    • 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
  • /41

    $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
  • /11

    $999,000 New Construction

    • 3 Beds
    • 4.5 Baths
    • 6,762 Sq Ft

    67 Blunt Rd, Egremont, MA 01230

    Unbelievable opportunity! The real hard work has been done for this six thousand square foot Timber frame home with three levels on over sixteen acres of land. Lots of the finishing materials are on site and ready to be installed. Architectural plans are available. Wonderful local mountain views and a stream with pond site make this the perfect setting. Why settle for someone else's vision when

    Ryan Lane GILCREST PROPERTIES

    67 Blunt Rd, Egremont, MA 01230
  • /14

    $119,000

    • Land
    • 1.17 Acres
    • $101,710 per Acre

    2 Terra Ferma Dr, Egremont, MA 01230

    Build your dream home on Terra Ferma Drive--arguably the best dead-end road in the Berkshires. Located just minutes from South Egremont, Great Barrington, and Catamount Ski Area, this is the ideal location to stake your ground. The road hosts a quiet neighborhood that leads directly to state hiking trails, putting the outdoors just steps from your door. This lot is perced and ready to build.

    Tony Segalla LANCE VERMEULEN RE, INC

    2 Terra Ferma Dr, Egremont, MA 01230
  • /23

    $495,000

    • 4 Beds
    • 2 Baths
    • 1,531 Sq Ft

    95 Water Farm Rd, Sheffield, MA 01257

    Open House 10-11-25, 11:00-1:00. Inside pictures to follow soon. Experience the perfect blend of modern comfort and historical charm in this beautifully maintained home. Featuring 4 spacious bedrooms and 2 baths, this home offers over 1,500 sq. ft. of living space. Enjoy the character of the 1850s with updates, including new mechanicals. Freshly painted inside and out, this home is truly move-in

    Suzann Ward HOUSATONIC REAL ESTATE

    95 Water Farm Rd, Sheffield, MA 01257
  • /43

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft

    166 Berkshire School Rd, Sheffield, MA 01257

    Nestled in Sheffield Village on 8+ acres, this charming New England farmhouse blends rustic character with modern comfort. Featuring 3 bedrooms, 2 baths, wood floors, beams, Great Room with a gas stove offers a warm inviting space Enjoy a country kitchen with a pantry. Screened in porch with outdoor patio, gardens, and two sheds for storage or hobbies. Perfect as a private sanctuary or Airbnb,

    Suzann Ward HOUSATONIC REAL ESTATE

    166 Berkshire School Rd, Sheffield, MA 01257
  • /20

    $389,000

    • 2 Beds
    • 1 Bath
    • 1,048 Sq Ft

    68 Creamery Rd, Great Barrington, MA 01230

    Sweet ranch in an unbeatable location. Located in lovely, low tax Egremont, this turn key property is minutes away from Great Barrington, New York state, and all that Berkshire County has to offer.One level living, this home includes two bedrooms, one full bath, hardwood floors and tons of light. A spacious kitchen opens into the living room, which centers around a cozy fireplace.A large,

    Lauren Rosen LANCE VERMEULEN RE, INC

    68 Creamery Rd, Great Barrington, MA 01230
  • /6

    $265,000

    • Land
    • 1.97 Acres
    • $134,518 per Acre

    14 McGee Rd, Egremont, MA 01230

    Lovely building lot on a quiet road in bucolic Egremont. Well has been drilled, septic design done for two structures and power is brought to site. Truly ready for your design/build.

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    14 McGee Rd, Egremont, MA 01230
  • /31

    $945,000

    • 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
  • /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
  • /17

    $795,000

    • 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
  • /48

    $2,995,000

    • 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
  • /23

    $149,000

    • Land
    • 1.11 Acres
    • $134,233 per Acre

    10 Miller View Rd, Egremont, MA 01230

    Tucked away on a quiet cul-de-sac in the desirable Baldwin Hill area of North Egremont, this 1.1 acre building lot offers seasonal mountain views and a serene setting. Partially cleared with easy access to an electrical transformer at the property's edge, this property is an ideal site for your future home. Conveniently situated just minutes from great Barrington, and all the Berkshire's has to

    Vashti Poor LANCE VERMEULEN RE, INC

    10 Miller View Rd, Egremont, MA 01230
  • /86

    $2,150,000

    • 5 Beds
    • 4.5 Baths
    • 4,842 Sq Ft

    173 Hillsdale Rd, Egremont, MA 01230

    Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlife and Nature Conservancy on 3 sides, custom-built home offers extraordinary privacy and tranquility. Crafted using wood milled directly from the property, this rustic yet contemporary home boasts a wealth of unique details that highlight exceptional craftsmanship. Moose, deer, bear, turtles, fox and more

    Robert Cohen eXp REALTY

    173 Hillsdale Rd, Egremont, MA 01230
  • /40

    $340,000

    • 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
  • /36

    $499,000

    • 4 Beds
    • 2 Baths
    • 2,076 Sq Ft

    36 Egremont Plain Rd, Great Barrington, MA 01230

    Don't miss this charming 4-bed, 2-bath home with 2 first-floor bedrooms and a full bath! Offering nearly 2,100 sq. ft. of living space and almost 1 acre of flat, dry land, this home provides plenty of room to grow. The breezeway connects the 2-car garage with newer doors and electric openers. Outside, enjoy a private patio, stone wall, and a shed for extra storage. The home has also just had the

    William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    36 Egremont Plain Rd, Great Barrington, MA 01230
  • /26

    $609,000

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    54 Egremont Plain Rd, Great Barrington, MA 01230

    New England farmhouse with distant views. Large common rooms & kitchen great room are bathed in sunlight. Beautiful pine floors & exposed beams throughout the 1st floor. Extra room on the first floor can be used as a bedroom or an office (not pictured.) Many structural renovations in 2004, central air, in line generator, in ground pool, screened porch & so much charm. The flat 3.89 acres allows

    Katie Williams STONE HOUSE PROPERTIES, LLC

    54 Egremont Plain Rd, Great Barrington, MA 01230
  • /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
  • /5

    $1,500,000

    • Land
    • 122.61 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
  • /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
  • /10

    $329,000

    • Land
    • 8.69 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
  • /20

    $3,495,000

    • Land
    • 225 Acres
    • $15,533 per Acre

    685 S Egremont Rd, Great Barrington, MA 01230

    *NEW PRICE* 225 Acre 18 hole Golf Course / Horse Ranch in the heart of the Berkshires. Former Egremont Country Club. Endless possibilities for the entrepreneur, builder or dreamer. Located a little over 2 hours from NY City, Greenwich & Boston.

    Steven Weisz William Pitt Sothebys Intn'l

    685 S Egremont Rd, Great Barrington, MA 01230
  • /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
  • /4

    $425,000

    • Land
    • 17.93 Acres
    • $23,701 per Acre

    99 Creamery Rd, Egremont, MA 01230

    NORTH EGREMONT - Almost 18 elevated acres with sweeping views of the Berkshire Hills that has been surveyed, flagged with enough road frontage to subdivide once. An open meadow with woodlands as a backdrop make this parcel most desirable....a must see!

    Cortney Dupont COHEN & WHITE ASSOCIATES

    99 Creamery Rd, Egremont, MA 01230
  • /2

    $2,400,000

    • Land
    • 38.2 Acres
    • $62,827 per Acre

    3 Jenssen Rd, Egremont, MA 01230

    3 lots available to develop in EgremontParcels, 008.0-0000-0123.0, 008.0-0000-0283.0, 008.0-0000-0048.0

    Jeremy Casey SR Commercial Realty

    3 Jenssen Rd, Egremont, MA 01230
  • /24

    $299,900

    • 6 Beds
    • 5.5 Baths
    • 3,683 Sq Ft

    175 Main St, Sheffield, MA 01257

    Come this charming 1820 colonial located in Downtown Sheffield! This unique property features 6 bedrooms and 5 and half bathrooms. Lovely hardwood showcasing wide plank and parquet style floors encompass 3,683 square feet of living space. Plenty of off street parking due to the oversized driveway and 2 car attached garage with loft space. Full, unfinished basement can provide additional storage

    Nicholas Decaro Property Works New England

    175 Main St, Sheffield, MA 01257
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