88 properties for sale in East Sheffield, Sheffield town Berkshire County Massachusetts

Sweet farmhouse on over 4 acres in Ashley Falls! Enjoy many original details, wide plank floors and newer additions of a mudroom entry and roomy screened porch! First floor bedroom with half bath could serve as an office while two bedrooms and a laundry/closet area complete second floor. The barn has a new metal roof and space for your workshop or studio. Wonderful gardens all around property. Many opportunities for this home's next chapter!

Nestled on a quiet cul-de-sac, this beautifully maintained Cape-style home offers privacy, character, and exceptional outdoor space on a level 2.37-acre lot. Featuring an attractive chateau-inspired exterior with a combination of stucco and wood siding, this home blends timeless charm with modern updates. Inside, you'll find four bedrooms, including a convenient first-floor bedroom and three additional bedrooms on the second level. The spacious primary bedroom features a private balcony overlooking the beautiful grounds. A full bath on both the first and second floors provides added convenience for family and guests. The home offers a large combination living and dining room, an inviting eat-in kitchen, and a cozy den warmed by a propane stove-perfect for relaxing on cool evenings. The finished lower level expands the living space with a generous family room, dedicated office area, workshop, and abundant storage. Additional highlights include a detached two-car garage with pull-down at

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 and stream from your farmhouse sink and natural soapstone countertops, complemented by oak flooring throughout. During the cooler months, relax by the fireplace in the living room, which has been modernized to enhance the flow between the kitchen and porch, thereby maximizing the sense of space and expanding the home's footprint. This layout supports four bedrooms and three fully renovated bathrooms, all featuring contemporary tile work. Additionally, there is a full basement that includes separate storage and bonus room. Minutes from the CT state line and 20 minutes from Great Barrington, MA

PRISTINE LAKEFRONT SANCTUARY: Perfectly sited with generous frontage on the shores of Lake Windemere, this sprawling post and beam residence offers lakefront views from every room, with four bedrooms and three and a half baths, blending rustic elegance with timeless comfort. Windmere Lake is a privately owned lake flanked by homes tucked away along the waterfront. Designed for gathering and gracious living, the home provides expansive spaces for family and friends to come together while embracing the natural beauty that surrounds it. Whether enjoying peaceful mornings by the water or hosting memorable evenings in the warm, inviting interiors, this is country living at Enjoy four of the best restaurants the Berkshires has to offer just minutes away. Only 3 miles from the Southfield store which offers delicious coffee and sandwiches. Down by the water, there is a beautiful landing with electricity for a fridge so you can enjoy a beverage while taking in the amazing sunset over the lake.

Marcel Breuer partner Tician Papachristou designed this home as a private paradise for his three-generation family: a long driveway leads past a tennis court, guest house, swimming pool, gazebo, and gym shed to a three-level modern house evoking the New England barn. From the third-floor master loft suite with private terrace and kitchenette, a skylit central stair leads to the mid-level kitchen/dining room with fireplace nook, between stone patio and screened porch. An atrium living room includes cozy coffered-ceiling seating by a fireplace. A cherry-walled study with private porch, pass-through full bathroom, and family room complete the floor. Family or guests on the lower floor enjoy four bedrooms and three bathrooms, as well as laundry room and two-car internal garage. The 72 acres The 72 acres surrounding the house include a screened hut overlooking a private beaver pond, a stream, and paths through the woods

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 integrity and striking original details that highlight its historic charm. While the property is ready for extensive updates, its strong bones and preserved features provide an exceptional foundation for a transformative renovation. Ideally situated in North Canaan, the property abuts a popular golf course, offering scenic surroundings and added appeal for future value. The peaceful setting provides both privacy and a connection to nature, making it an excellent candidate for a full-time residence, weekend retreat, or investment project. Whether you're an investor, renovator, or a lover of hist

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, this property combines timeless charm, tranquil surroundings, and great potential

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 Great Barrington, 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 garage. A brand-new adjoining apartment includes a beautifully finished kitchen with granite countertops, full bath, washer/dryer, and private backyard access deal for rental income, extended family, Airbnb, or professional office use. Additional updates include a new 3-bedroom septic system and new roof

RARE MULTI FAMILY OPPORTUNITY - Side by side duplex with 3 bedrooms in each unit. All individual utilities including separate oil baseboard heat. One unit has had an extensive renovation just completed, the other needs updating. Detached two car garage, and both units have an enclosed rear porch. Convenient in town location is walking distance from dining, pharmacy, post office, library, elementary school, pool and more. Ideal for owner occupancy in one unit while the other is brought up to date

A remarkable opportunity to combine residencial on the second floor with commercial on the main floor in an excellent location with plenty of private parking. The kitchen is set up for the discerning chef, a large dining room, a bedroom/office and living room with a propane fireplace completes the first floor. The gorgeous hardwood floors throughout the house have just been finished and the house is in pristine shape for the next owner. Finally, there is central air on the second floor to complete the full package!

Discover quintessential Berkshire charm and modern elegance in this Sheffield retreat. Sitting on 2+ level acres, this 3BR, 3.5BA residence offers 2,748 sq ft of pristine living space across 3 independent levels. The sun-drenched open main floor features wide-plank oak floors, a cozy gas fireplace, a convenient half bath, and a chef's kitchen of your dreams flowing to a wrap-around deck. With 3 private suites-including a primary oasis, a secluded loft, and a walk-out lower level with a wet bar-this property is a perfect vacation rental or private escape. Enjoy peace of mind with new multi-zone HVAC, spray foam insulation, UV water filtration, and a whole-home generator, all high efficiency systems. Located 15 minutes to Great Barrington and 45 minutes to the Wassaic NYC train. Come see!

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 cozy study with a stunning stone hearth. The kitchen includes an informal dining area and plenty of storage, making it perfect for both everyday meals and entertaining. It is a chef's delight. Dual ovens w air fryer, induction cook top, stainless hood and a natural live edge wood top. Step outside to enjoy your screened-in porch with ceiling fans, a large private deck w a hot tub, and a tranquil backyard surrounded by nature. The walkout lower level is finished with a full bath, an extra kitchen, and a bonus storage room ideal for a wine cellar. Additional features include a walk-up attic, centr

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 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26

Historic Norfolk Village Home on 3.4 Acres Classic Litchfield County setting defines this 3.4-acre property at the edge of Norfolk village. Lovingly held within the same family for generations, this captivating 1907 antique home sits on flat, open land with a classic large country barn, hay fields, and a spring-fed seasonal brook. The charming five-bedroom, two-bath residence retains its finest period details: welcoming front and side porches, original wood trim, stained glass windows, and hardwood floors. The full two-story layout features 9.5-foot ceilings and generous room proportions on the first floor, various sized bedrooms on the second, a walk-up attic above, and a full basement below. Sun-filled and tranquil, this home awaits your vision - whether renovation or preservation, the bones are excellent. Nestled in a lovely neighborhood and only minutes away from Norfolk's coveted amenities, this offering is a rare opportunity

The Hatfield House: A rare 1793 Sheffield antique offering a unique renovated live/work opportunity, move-in ready; the main residence blends historic character with modern systems; including a new sealed basement. 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 for gallery, studio, office, or home business use inside the adjacent 1,200 sq ft three-bay barn with electricity. Unusual space and privacy adds versatility for a Main Street location. Formerly a famous antiques destination, this property combines history, functionality, and long-term value just a quick drive from downtown Great Barrington

SOUTH BERKSHIRE COUNTY, UPDATED VILLAGE CENTER HOME and OFFICE This graciously restored vintage house has all the benefits of an ideal Sheffield setting with walkability to restaurants, Bushnell-Sage Library, Dewey Hall, post office, bank, and churches. With residential/commercial zoning, the house features an above-garage private large office/studio, a 1,000 sq. ft. outbuilding with plumbing and electric service, 4 auto car-bay doors, and a separate parking area. There are several possible uses for the property, including a business and/or accessory dwelling unit for possible rental income. The home itself is spacious and bright, combining period detail with updates. High ceilings, wonderful light, crown molding, soapstone counters, farmer's sink, cherry cabinets, and built in hutch. French doors, a large 1st floor Laundry Room, radiant heat in both upstairs bathrooms, and walk-in closets add to the appeal. The oversized garage, new septic system, new water heater, water softener, att

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 options. There are 4 fireplaces at the home including an oversized hearth on the first floor. The home also showcases a wood deck and covered porch. Located in close proximity to local restaurants and public transportation. Schedule you showing today!

Set on four private acres along a quiet stretch of road by the Housatonic, this is the kind of place that reveals itself slowly. The driveway is lined with rhododendrons that light up every spring, and the rest of the landscape is paced to bloom straight through summer - fruit trees, azaleas, perennials, blueberries, raspberries, all of it planted by someone who clearly knew what they were doing. Out back, a brook babbles through the yard. The Sheffield covered bridge, about as scenic as New England gets, is an easy walk away. Inside, the first floor opens up and flows - wood floors throughout, and a wood-burning fireplace that anchors the whole space. There's a full bath on the main level. Upstairs, the primary has its own en suite, and the other two bedrooms share a half bath. The detached three-car garage is a real bonus. Room for bikes, kayaks, and whatever your adventures call for - or a modest car collection. And the unfinished second floor is a blank slate, ready to become an AD

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 storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep

Step into a canvas of timeless character in this Historic Colonial, originally built and occupied by Nathaniel Austin,a surveyor who was instrumental in mapping and settling Berkshire County, situated in the town of Sheffield. This 5-bedroom, 2-bathroom residence offers a rare opportunity to restore a piece of Berkshire County history while imprinting your own vision on its enduring architecture. Location and Lifestyle* Tree-lined driveway, a short stroll to the village green, markets, dining, and outdoor recreation. Proximity to the Housatonic River, lakes, and scenic trails, inviting year-round strolling, hiking, and local exploration. Easy access to regional attractions, farms, and cultural events that define the area's heritage. Exterior and Structural Potential* Traditional Colonial silhouette with original exterior detail awaiting revival. clapboard siding offers excellent restoration potential. Generous lot space with room for landscaping, a garden, or outdoor living areas once

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and restaurants. Nestled amidst beautiful, well-maintained grounds, this residence exudes curb appeal. The apartments have all been thoughtfully updated and come equipped with outdoor space, access to laundry facilities, and exceptional parking

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 gorgeous antique floors-seamlessly paired with an expansion which added a large family room with a fourth fireplace, finished basement storage, mudroom, and partially screened wraparound porch. Sun-filled living spaces feature vaulted ceilings and exposed beams. The chef's kitchen boasts premium appliances and a walk-in pantry. A versatile ground floor offers guest quarters or a private suite with full bath and separate entry. Upstairs, retreat to a luxurious master suite with spa-like bath, cedar walk-in closet, and beamed ceilings, plus two additional bedrooms and a spacious landing perfect for a hom

Attention investors! This property features a primary bedroom with a half bath, along with three additional bedrooms, offering plenty of living space. The combined two lots total 7.99 acres, providing ample room for expansion. Having been vacant for several years, this property presents a blank canvas, ready for someone with a vision to restore it to its former glory. Potential buyers should be aware that the property does not qualify for FHA, CHFA, or government financing, so alternative funding will be necessary. Additionally, the buyer will be responsible for removing all items from the property. The property at 321 Salisbury Road spans 6.99 acres, and the adjoining lot at 313 Salisbury Road is 1 acre, which will be included in the transaction. Please note that the 313 Salisbury property has a vacant trailer on the lot, which the buyer will also need to manage. The property is being sold As Is. It has been inspected, and the septic system has failed the Title 5 inspection

Charming 1900s stucco farmhouse with antique details such as maple floors, plaster walls, and silver-painted radiators are met with modern upgrades including thermal windows throughout and 2006 Buderus boiler, Viessman Vitrocell hot water heater, newer roof and oil tank. Enter through the heated mudroom past a full bath into the spacious kitchen with double drainboard farmhouse sink and sunset views over Canaan valley. Two front rooms and a three-season porch round out the first floor. Upstairs there are 4 nice-sized bedrooms, one on each corner, with knotty pine floors, ceiling fans, and plaster walls. The upstairs full bath is located over the mudroom on the northeast corner overlooking the barn. There is a full attic accessed with pull-down stairs and a large walk-out basement with multiple windows. Of note, both bathrooms need renovation and kitchen likely does too. Half acre fenced, corner lot. Lush landscaping frame flagstone walkways and landings. There are two matching red-pain

Down a long private drive, this light-filled, artisan-built Cape blends over 5 acres of meadow and woods with Haystack Mountain views into a rare setting-complete privacy and close to town, summer music concerts, and the local swimming hole. Native cherry hardwood floors, solid wood doors, and wood trim run throughout. A central chimney anchors two fireplaces, while the main-floor primary suite allows for easy one-level living. Efficient mini-split heating and cooling provide year-round comfort, with a furnace for the coldest winter days. The upper level offers two bedrooms, a full bath, abundant storage, and an unfinished skylit room with potential for a studio, office, or additional living space. A mostly finished, dry walkout basement adds valuable living space with a recreation room, full bath, and French doors leading outdoors. Another room offers numerous possibilities. Featuring a 2021 roof and an oversized Western red cedar deck completed in 2024, this well-maintained home is m