99 houses for sale in 01244

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

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 ULTIMATE FOUR SEASON BERKSHIRE RETREAT- Tucked away on 3.6 serene acres, this bright and airy single-level home is the perfect year-round escape. This completely renovated home offers an open concept main living area including the dining room, efficient eat-in kitchen with stainless steel appliances and family room with wood stove, perfect for relaxation and entertaining. Two additional guest rooms and a den. The newly completed primary suite boasts a beautiful bathroom and an oversized walk-in closet versatile enough for a home office. Outside, the private grounds feature a dining patio, fire pit, gazebo and shed. Located just minutes from the slopes of Ski Butternut and downtown Great Barrington, this turnkey property also features a proven track record as a short and long term rental MORE Propane has been added with additional plumbing to set up gas powered cooking if desired and possibility to convert wood stove to a gas option. House plumbed for forced air system. The Master S

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

Welcome home to NEWGRANGE. 1920's era Manor House with lake frontage on Lake Garfield. Over 10,000 square feet of living on 7.7 Acres. Complete the restoration and enjoy original Stone Fireplaces, comfortable Living spaces, formal Dining and 10 Bedrooms. Write that novel in the paneled Office, Library or Sunroom, create delicacies in the Country Kitchen, or shoot a round of pool in the Billiard Room. When you are done, meander to your private Dock on 165 feet of glorious private lakefront. Guest House, Pond, and Gardens originally designed by Frederick Law Olmstead. Close to town, Skiing, Shopping, Dining and Tanglewood. Low, low Monterey taxes. This one-of-a-kind property is meant for enjoying all that the Berkshires has to offer

OUTSTANDING COUNTY LIVING in idyllic Monterey with its low real estate taxes and easy access to Lake Garfield and Lake Buel. Butternut Ski Area is only 5 minutes away. 8 minutes to downtown Great Barrington. This Timber Fame (open floor plan) contemporary home features beautiful (wide-plank) pinewood floors, a cathedral ceiling Great Room, and a bonus sleeping loft area. A fireplace on the main level, and a wood stove on the lower level, add warmth and charm. Ready to move right in' With relatively low inventory level, particularly in Monterey, this listing is a lucky strike extra. Schedule your showing today

Loads of room for family and friends in this semi-private country home near The Old Inn on the Green and The Southfield Store Cafe. The first floor features spacious living areas, including a living room with a wood-burning fireplace, a large eat-in kitchen and dining area, and a paneled den, along with an attached two-car garage. Two of the six bedrooms are on this level, including the primary and an adjacent bedroom currently used as a home office. The adjoining room offers the potential to create an expansive en-suite bath and walk-in closet. Upstairs are four generously sized bedrooms, a full bath, and a large laundry room. A full basement provides ample storage and houses a new Buderus boiler. Set well back from the road, the property enjoys a large, private backyard

Loads of room for family and friends in this semi-private country home near The Old Inn on the Green and The Southfield Store Cafe. The first floor features spacious living areas, including a living room with a wood-burning fireplace, a large eat-in kitchen and dining area, and a paneled den, along with an attached two-car garage. Two of the six bedrooms are on this level, including the primary and an adjacent bedroom currently used as a home office. The adjoining room offers the potential to create an expansive en-suite bath and walk-in closet. Upstairs are four generously sized bedrooms, a full bath, and a large laundry room. A full basement provides ample storage and houses a new Buderus boiler. Set well back from the road, the property enjoys a large, private backyard

Step into history at 1001 Canaan Southfield Rd, a rare 1797 Colonial estate set on over 23 breathtaking acres of mature, landscaped grounds. This extraordinary property features two serene ponds with fountains, over 300 feet of classic stone walls, and the scenic Umpachene River winding through the land. Extensive landscaping, stone patios, and picturesque outdoor spaces create a private retreat unlike any other. The home offers 4 bedrooms, including a spacious primary suite, blending timeless character with natural beauty. Included are three separate parcels, with an additional lot located across the street, offering endless possibilities for expansion, recreation, or investment. A truly one-of-a-kind Berkshire property rich in history, charm, and unmatched natural surroundings

This Southfield home has been thoughtfully renovated and expanded, blending timeless New England charm with exceptional modern comfort. The stunning kitchen - featured in Bon Appetit - just received new stone countertops and sink. A gorgeous, wrap-around screened porch overlooks the entire backyard and stream. A renovated full bath creates the option of a primary suite on the first floor. A third-floor conversion (not included in the square footage) creates a magical hideaway for an office, fitness room or bonus guest space. Among the updates: all-new, multi-zone heating and cooling system, whole-house back-up generator, EV charger, and radiant heat in the kitchen floor. All that and you can roll out of bed for a short stroll to your morning coffee at the beloved Southfield Store

Step into history at 1001 Canaan Southfield Rd, a rare 1797 Colonial estate set on over 23 breathtaking acres of mature, landscaped grounds. This extraordinary property features two serene ponds with fountains, over 300 feet of classic stone walls, and the scenic Umpachene River winding through the land. Extensive landscaping, stone patios, and picturesque outdoor spaces create a private retreat unlike any other. The home offers 4 bedrooms, including a spacious primary suite, blending timeless character with natural beauty. Included are three separate parcels, with an additional lot located across the street, offering endless possibilities for expansion, recreation, or investment. A truly one-of-a-kind Berkshire property rich in history, charm, and unmatched natural surroundings

This Southfield home has been thoughtfully renovated and expanded, blending timeless New England charm with exceptional modern comfort. The stunning kitchen - featured in Bon Appetit - just received new stone countertops and sink. A gorgeous, wrap-around screened porch overlooks the entire backyard and stream. A renovated full bath creates the option of a primary suite on the first floor. A third-floor conversion (not included in the square footage) creates a magical hideaway for an office, fitness room or bonus guest space. Among the updates: all-new, multi-zone heating and cooling system, whole-house back-up generator, EV charger, and radiant heat in the kitchen floor. All that and you can roll out of bed for a short stroll to your morning coffee at the beloved Southfield Store

This recently renovated cottage, set on 4 woodland acres in beautiful Monterey enjoys close proximity to Lake Garfield, for boating and swimming, and plentiful hiking trails throughout the town. With 750 square feet of bright, clean, efficient living space, and a large detached garage, the cottage is the perfect Berkshires getaway. Recent upgrades include a spacious deck, interior painting, a refurbished bath and partially fenced back yard. Truly a little gem in the woods! Offered fully furnished. Move in for the Summer!

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.

NODIN FARM. A spectacular 130 acre property, rich in history, and lovingly maintained by only four owners during the past 225 years. Perhaps the word 'Farm' understates the true magnificent character and charm of this outstanding home that has been carefully expanded and preserved and updated with premium appliances, the highest quality cabinetry, and with state-of-the art heating and AC equipment. True to its history the 'farm' encompasses a large barn complex with one wooden and one main gambrel roof brick barn. There is a separate brick 'bull barn' with architectural plans for a guest house. Did I mention the 7 bay brick car garage with an office and a gym' The entire barn complex was repaired and shingled with premium asphalt shingles in 2024! This is a must see property

NODIN FARM. A spectacular 130 acre property, rich in history, and lovingly maintained by only four owners during the past 225 years. Perhaps the word 'Farm' understates the true magnificent character and charm of this outstanding home that has been carefully expanded and preserved and updated with premium appliances, the highest quality cabinetry, and with state-of-the art heating and AC equipment. True to its history the 'farm' encompasses a large barn complex with one wooden and one main gambrel roof brick barn. There is a separate brick 'bull barn' with architectural plans for a guest house. Did I mention the 7 bay brick car garage with an office and a gym' The entire barn complex was repaired and shingled with premium asphalt shingles in 2024! This is a must see property

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.

Charming rustic 3-bedroom, 1.5-bath home located on a picturesque country road in the Village of Southfield. Full of character and warmth, this inviting property offers a peaceful setting just minutes from the Southfield Store. With both residential and commercial zoning, it presents a unique opportunity for a primary residence, home-based business, or investment. Enjoy the charm of country living with the flexibility to suit a variety of needs in one of the area's most desirable village locations. There is also a huge garage on the property

Charming cottage-style home that offers far more space than meets the eye! The first floor features a spacious kitchen with abundant cabinet storage, pantry space, and a newer gas range, along with a cozy office nook, dining room, living room, full bath, two bedrooms, laundry room, and an inviting den. Upstairs offers three additional rooms, including two bedrooms, providing flexible space for guests, hobbies, or a home office. This home has seen many updates since 2019, including a new furnace, oil tank, front siding, and all new windows on the front of the house. Beautiful hardwood floors were added in the living room, dining room, and first-floor bedrooms, while the kitchen, laundry room, and den feature durable new laminate flooring. Additional highlights include a walk-out basement. With some updating, this home has tremendous charm and potential - a wonderful opportunity to create your dream space while enjoying the character and generous layout this property already offers. All

Charming cottage-style home that offers far more space than meets the eye! The first floor features a spacious kitchen with abundant cabinet storage, pantry space, and a newer gas range, along with a cozy office nook, dining room, living room, full bath, two bedrooms, laundry room, and an inviting den. Upstairs offers three additional rooms, including two bedrooms, providing flexible space for guests, hobbies, or a home office. This home has seen many updates since 2019, including a new furnace, oil tank, front siding, and all new windows on the front of the house. Beautiful hardwood floors were added in the living room, dining room, and first-floor bedrooms, while the kitchen, laundry room, and den feature durable new laminate flooring. Additional highlights include a walk-out basement. With some updating, this home has tremendous charm and potential - a wonderful opportunity to create your dream space while enjoying the character and generous layout this property already offers. All

Step into history at 1001 Canaan Southfield Rd, a rare 1797 Colonial estate set on over 23 breathtaking acres of mature, landscaped grounds. This extraordinary property features two serene ponds with fountains, over 300 feet of classic stone walls, and the scenic Umpachene River winding through the land. Extensive landscaping, stone patios, and picturesque outdoor spaces create a private retreat unlike any other. The home offers 4 bedrooms, including a spacious primary suite, blending timeless character with natural beauty. Included are three separate parcels, with an additional lot located across the street, offering endless possibilities for expansion, recreation, or investment. A truly one-of-a-kind Berkshire property rich in history, charm, and unmatched natural surroundings

This Southfield home has been thoughtfully renovated and expanded, blending timeless New England charm with exceptional modern comfort. The stunning kitchen - featured in Bon Appetit - just received new stone countertops and sink. A gorgeous, wrap-around screened porch overlooks the entire backyard and stream. A renovated full bath creates the option of a primary suite on the first floor. A third-floor conversion (not included in the square footage) creates a magical hideaway for an office, fitness room or bonus guest space. Among the updates: all-new, multi-zone heating and cooling system, whole-house back-up generator, EV charger, and radiant heat in the kitchen floor. All that and you can roll out of bed for a short stroll to your morning coffee at the beloved Southfield Store

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 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 new finished kitchen with granite countertops, washer/dryer, and private backyard access deal for rental income, or professional office use. Updates include a new 3-bedroom septic system and new roof, backyard fence and new grass. Some images have been digitally altered to include virtual staging

Charming cottage-style home that offers far more space than meets the eye! The first floor features a spacious kitchen with abundant cabinet storage, pantry space, and a newer gas range, along with a cozy office nook, dining room, living room, full bath, two bedrooms, laundry room, and an inviting den. Upstairs offers three additional rooms, including two bedrooms, providing flexible space for guests, hobbies, or a home office. This home has seen many updates since 2019, including a new furnace, oil tank, front siding, and all new windows on the front of the house. Beautiful hardwood floors were added in the living room, dining room, and first-floor bedrooms, while the kitchen, laundry room, and den feature durable new laminate flooring. Additional highlights include a walk-out basement. With some updating, this home has tremendous charm and potential - a wonderful opportunity to create your dream space while enjoying the character and generous layout this property already offers. All

3 BR 2 Bath Home with tons of storage and lots of space. Great opportunity for a small homestead or someone looking for a home with shope space and outbuilding. BEING SOLD AS IS