669 properties for sale in Sheffield town

Set on four private acres along a quiet stretch of road near the Housatonic, this is a property that keeps to itself. No sightlines from the neighbors, no road noise to speak of, just the sound of the brook that runs through the back of the yard. This is a place built for quiet enjoyment, and the land delivers it in full. The gardens are the kind that take decades to get right, and someone got them right. The driveway is lined with rhododendrons that light up every spring, and from there the whole landscape is paced to bloom straight through summer. Fruit trees, azaleas, perennials, blueberries, raspberries. Walk it in July and you understand: this wasn't landscaping, it was devotion. And for all that's established, there's still room to put your own touch. Inside, the first floor opens up and flows, with wood floors throughout and a wood-burning fireplace that anchors the whole space. A full bath sits on the main level. Upstairs, the primary has its own en suite, and the other two bed

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

Privately set on just under 7 acres, this beautifully renovated home offers the perfect combination of tranquility, privacy, and convenience. A meticulously paved circular driveway leads through elegant, iron fencing to the level, beautifully landscaped property. The home offers approximately 2,800 square feet of thoughtfully updated living space, with 3 to 4 bedrooms and 2 full baths across two spacious levels. Natural light fills the interior, highlighting beautiful wood floors throughout and adding to the warm, inviting atmosphere. Skylights bring even more light into the home, while the oversized deck provides an ideal setting for outdoor entertaining, relaxing, and enjoying the peaceful surroundings. An oversized two-car garage offers generous parking and storage. Tucked away in a completely private setting yet just minutes from town, this exceptional property is approximately two minutes from Sheffield's Cobble and the Appalachian Trail, offering easy access to hiking, nature, an

JUST REDUCED TO $429,000! 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, backyard fence and new grass

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 offered with 3 business rentals and 2 apartments creating a living and income opportunity

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. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires. Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind. The vaulted ceiling in the kitchen adds a sense of light and openness, while seamless transitions between the kitchen, dining area, and living room create a space that feels both cohesive and welcoming. A cozy wood-burning fireplace anchors the living room, adding

Views, privacy, and frontage on Mill Pond. This custom built classic Gilligan house is the perfect home for hosting family and friends with plenty of space both inside, and out. There are 4 plus bedrooms and 5 baths, including a generous primary suite on the first floor, a large den, and a bonus room above the 2 car garage. The property includes a fenced, in- ground pool, extensive flat lawn, perfect for soccer or croquet, and a private dock for paddle boats, fishing and watching out for the resident Bald Eagle! The house sits on 4.49 acres and also includes 4 additional lots for a total of almost 13 acres

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

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. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires. Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind. The vaulted ceiling in the kitchen adds a sense of light and openness, while seamless transitions between the kitchen, dining area, and living room create a space that feels both cohesive and welcoming. A cozy wood-burning fireplace anchors the living room, adding

Spacious 4-bedroom 1+1/2 bath Cape with several useful storage buildings and a convenient 2 car attached garage. Heated sunroom with sliding windows, Eat in kitchen with access to back patio, Livingroom with knotty pine paneling and wood burning stove. FIRST FLOOR has 2 bedrooms, full bathroom with walk in shower, LR, kitchen and sunroom. UPSTAIRS has two bedrooms and a half bath. Large wood stove in the basement. Oil furnace for entire house. Passing Title V

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

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

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

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. Plans for new 2nd floor bathroom! 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

Enjoy comfortable, move-in-ready living at this inviting Sheffield property, complete with a barn and access to a nearby pond for fishing and kayaking. The versatile layout is ideal for extended family, guests, a home office, or supplemental rental income. Sheffield Center is approximately two miles away, offering restaurants, the Bushnell-Sage Library, the Sheffield Historical Society, and the welcoming character of this historic Berkshire village. Great Barrington's restaurants, shopping, and everyday conveniences are just 15 minutes away, while Canaan, Connecticut, is approximately 10 minutes away. Modern construction completed in 2021 Excellent overall condition with minimal anticipated deferred maintenance Desirable two-family configuration Separate electric utilities for each apartment Strong appeal to both owner-occupants and investors Both units currently vacant, allowing immediate occupancy or rental opportunities Convenient Sheffield location with access to Great Barrington,

A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently located on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth and craftsmanship of another era. 16 rooms, 5 bedrooms, multiple baths and 4 fireplaces, the home features beautiful wide-board floors, period details, sun-filled rooms and gracious proportions. A large three-season porch and welcoming front deck extend the living spaces and add to the home's timeless village appeal. With its rich history, wonderful scale and multipurpose zoning offering intriguing possibilities, this is a property ready for its next chapter-an opportunity to preserve its past while creating a home for generations to come. There is something truly special about a home that has been part of a village for more than two centuries. Built in 1819, this iconic Sheffield antique stands near the historic town center and predates the

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

Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access to a wrap-around deck. Upstairs, a treehouse-like loft adds charm, while the primary suite delivers a spa-like experience. The three suites were designed for intimacy and privacy. The walk-out lower level houses a guest suite and fantastic game room. Renovated top-to-bottom with no expense spared, central A/C, and new mechanicals-just bring your suitcase. 15 mins to Guido's and 45 mins to the Wassaic NYC train

Set on four private acres along a quiet stretch of road near the Housatonic, this is a property that keeps to itself. No sightlines from the neighbors, no road noise to speak of, just the sound of the brook that runs through the back of the yard. This is a place built for quiet enjoyment, and the land delivers it in full. The gardens are the kind that take decades to get right, and someone got them right. The driveway is lined with rhododendrons that light up every spring, and from there the whole landscape is paced to bloom straight through summer. Fruit trees, azaleas, perennials, blueberries, raspberries. Walk it in July and you understand: this wasn't landscaping, it was devotion. And for all that's established, there's still room to put your own touch. Inside, the first floor opens up and flows, with wood floors throughout and a wood-burning fireplace that anchors the whole space. A full bath sits on the main level. Upstairs, the primary has its own en suite, and the other two bed

Perched on a hill overlooking a scenic valley road, this 4-bedroom Dutch Gambrell offers a secluded country setting just a few minutes from town. This vibrantly-designed home opens into a handsome petrol-green kitchen with polished concrete floors and an ample dining area framed by French doors. The kitchen/dining area flows into an inviting living room anchored by a herringbone tile propane fireplace, a warm gathering space for family and friends. Just off the living room the 1st floor primary suite is a cheerful retreat with it's own striking classic black-and-white tiled bath with glass shower surround. Upstairs 3 guest bedrooms, a full bath and an upstairs playroom/lounge offer plenty of room for guests to relax. On the basement level there are two unheated semi-finished spaces for exercise and Media viewing. The lush back yard features a beautiful stone patio and hot tub. An attached 2-car garage with EV charging completes the package. Easy access to hiking, swimming, and everythi

Privately set on just under 7 acres, this beautifully renovated home offers the perfect combination of tranquility, privacy, and convenience. A meticulously paved circular driveway leads through elegant, iron fencing to the level, beautifully landscaped property. The home offers approximately 2,800 square feet of thoughtfully updated living space, with 3 to 4 bedrooms and 2 full baths across two spacious levels. Natural light fills the interior, highlighting beautiful wood floors throughout and adding to the warm, inviting atmosphere. Skylights bring even more light into the home, while the oversized deck provides an ideal setting for outdoor entertaining, relaxing, and enjoying the peaceful surroundings. An oversized two-car garage offers generous parking and storage. Tucked away in a completely private setting yet just minutes from town, this exceptional property is approximately two minutes from Sheffield's Cobble and the Appalachian Trail, offering easy access to hiking, nature, an

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

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

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

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 surrounding the house include a screened hut overlooking a private beaver pond, a stream, and paths through the woods

JUST REDUCED TO $429,000! 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, backyard fence and new grass

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. Plans for new 2nd floor bathroom! 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

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

This well-loved antique home offers a rare combination of history, thoughtful updates, and natural beauty. Set on 14+ acres with sweeping westerly mountain views, Carefully maintained over the years, the property has benefited from significant improvements, including an updated foundation, electrical and plumbing systems, heating system, windows, and roof. The home offers four bedrooms, two full baths, and a full basement, providing comfortable living space with the character and charm of an earlier era. Outside, the property unfolds across fields, gardens, mature fruit trees, and open land, with direct abutting state land and access to the Appalachian Trail nearby. An oversized detached garage with a second floor offers ample room for vehicles, equipment, storage, or a workshop. With its peaceful setting, mountain views, and connection to the surrounding landscape, this is a special property for someone who will appreciate its history and become its next steward

Enjoy comfortable, move-in-ready living at this inviting Sheffield property, complete with a barn and access to a nearby pond for fishing and kayaking. The versatile layout is ideal for extended family, guests, a home office, or supplemental rental income. Sheffield Center is approximately two miles away, offering restaurants, the Bushnell-Sage Library, the Sheffield Historical Society, and the welcoming character of this historic Berkshire village. Great Barrington's restaurants, shopping, and everyday conveniences are just 15 minutes away, while Canaan, Connecticut, is approximately 10 minutes away. Modern construction completed in 2021 Excellent overall condition with minimal anticipated deferred maintenance Desirable two-family configuration Separate electric utilities for each apartment Strong appeal to both owner-occupants and investors Both units currently vacant, allowing immediate occupancy or rental opportunities Convenient Sheffield location with access to Great Barrington,