A rare opportunity to own 5.2 acres in Pittsfield for under $400,000! Set in the scenic countryside of West Pittsfield, this spacious 1820s farmhouse offers nearly 2,000 sq. ft. of living space, historic character, and room to make it your own. Inside, you'll find hardwood floors, a fireplace, beautiful central staircase, oversized bedrooms, enclosed porch, and walk-up attic. Updates include a hot water heater (approx. 3 years), boiler and replacement windows (approx. 5 years), carpeting (approx. 1 year), and rebuilt front and side porches. Enjoy the space and privacy of country living while remaining just minutes from the conveniences of Pittsfield.

Welcome to 41 Pearl Street- a 1900s two-family residence nestled on a quiet street just moments from downtown Great Barrington. This spacious 4-bedroom, 2-bathroom (both sides are 2 BR/1 BA) home offers 1,964 square feet of living space on a generous 0.25-acre lot, containing that classic period charm. Step inside to discover a welcoming floor plan with ample natural light, hardwood floors, and period details. The kitchen and living areas are perfect for entertaining or relaxing with family. Upstairs, the bedrooms offer privacy and comfort, with plenty of storage throughout. Warm and efficient forced hot water heating.

This charming and move-in ready home invites you to settle into an easy Berkshire lifestyle. The first floor offers the comfort of one-level living, with a bedroom, full bath, laundry, and welcoming living spaces, while the second floor provides additional bedrooms and room for guests. Recent updates include an updated electrical service, refreshed interiors, and a beautiful enclosed porch made for slow mornings and quiet evenings. Just moments from shopping and dining, with downtown Lenox minutes away, Bousquet Mountain Ski Resort & Sports Center 4 minutes away, and Tanglewood about 10 minutes away. Spend your days exploring scenic trails, discovering local favorites, or enjoying the beauty of the Berkshires in every season.

Flexible In-Town Home with Business and investment Potential A rare in-town opportunity offering both comfortable living and adaptable space. This three-bedroom, two-bath home features a spacious eat-in kitchen, large dining/family room, and a flexible living room that can double as an office or additional bedroom. With a history as a combined home and professional office, the property is well-suited for a small home-based business, complete with ample parking and easy client access. Recent upgrades include a new boiler, hot water heater, and 2026 appliances, plus a brand-new roof on the rear portion of the home. First-floor laundry adds convenience. Live, work, or both--right in the heart of town. OPEN HOUSE - FRIDAY JUNE 26 4:00 p.m. - 5:30 p.m.

Beach days, porch evenings and Tanglewood concerts make this the perfect three-season Berkshire cottage. Vaulted ceilings and a fieldstone fireplace anchor the living room, while two bedrooms and a versatile loft provide comfortable space for family and friends. The screened in-porch extends the living space for long summer afternoons and evenings, while the dining room is filled with windows that bring nature inside. Set in the welcoming community of Mahkeenac Heights, this cottage is just a short walk to the town beach at Stockbridge Bowl and close to the Berkshires' many cultural attractions. A wonderful retreat for enjoying all the Berkshires have to offer!

Discover the perfect blend of timeless farmhouse charm and modern updates in this beautifully maintained home, ideally located just a short walk from the town center and the newly developed Mohican Trail System on Syndicate Road. Whether you're looking for convenient access to local shops, restaurants, outdoor recreation, or a peaceful place to call home, this property offers the best of both worlds. Set along the scenic Hoosic River, the property enjoys picturesque water views and a tranquil setting that creates a relaxing backdrop throughout the seasons. The classic farmhouse character is complemented by thoughtful updates, providing comfortable living while preserving the home's warmth and appeal.

Meticulously cared for by its original owner, this bright and welcoming 2 bedroom, 2.5 bathroom home offers the ease and comfort of true one level living in the highly desirable Walden Village community. The thoughtfully designed main floor features everything you need on one level, including a dedicated main floor laundry area with no need to carry baskets up and down stairs. Step out onto your private deck to enjoy a quiet cup of coffee in the morning sun. Downstairs, the walkout lower level offers fantastic additional living space, an updated bathroom, and direct access to a private patio, which is also perfectly situated to catch the morning light.

Get ready to relax in the Berkshires in your own condo with big windows, high ceilings, plus brand new boiler & A/C! Owner retiring and moving down south, giving up his beloved in town Great Barrington location. You'll love being close to stores and provisions for your various adventures, while being close to all the attractions that the Berkshires have to offer. Come experience worry free living while the condo cuts your grass in the summer, or plows your driveway while you ski. 9 Stanley is simply country living at it's best. Come experience it today!

Open house cancelled! Charming Cape Living on 1.16 Acres with Beautiful Views Welcome to 27 Madden Road! This inviting 3-bedroom, 2-bath Cape offers comfortable living and a versatile layout. The main level features an open floor plan with a spacious living room and fireplace, eat-in kitchen, full bathroom, and first-floor primary bedroom. Upstairs are two additional bedrooms and a second full bath. The finished lower level adds extra living area with a walkout, perfect for an office, gym, or hobby space. Set on 1.16 acres, there is plenty of room to relax, garden, entertain, and enjoy the surrounding views. Enjoy EZ Solar and property taxes under $800 per year, making this a great Berkshire getaway or year-round home!

Historic character meets modern updates in this beautifully renovated 1880s home! Thoughtfully updated while preserving its original charm and integrity, the home underwent an extensive renovation in 2016, including new electrical, plumbing, insulation, and much more. Beautiful wood floors flow throughout, adding warmth and character. The first floor offers flexible living with a bedroom or home office and a full bathroom. Upstairs, you'll find three additional bedrooms, another full bath, and the convenience of second-floor laundry. There is also potential to expand the primary suite with space for an additional bathroom that has already been roughed in.

This spacious in-town single family home offers a flexible five bedroom, 2.5 bath layout with generous living space throughout. Thoughtfully designed for comfort and versatility, it's well suited for a large household, multi-use living needs, or anyone seeking extra room to spread out. The second floor hosts 2 full bathrooms, ensuring convenience for all, while the first floor boasts a half bathroom and a huge laundry room for added practicality. The home showcases stunning wood floors throughout most of the home, adding warmth and character to the living spaces. Enjoy your morning coffee or evening relaxation on the inviting front porch, or take advantage of the large back deck and gazebo, offering a private and peaceful setting overlooking the lush property.

Bright, fresh and fabulous, this hip, rustic getaway is perched on a hill with forest and pond views. Open living-dining-kitchen, wonderful screened porch, two bedrooms and a bath on the first floor. Upstairs, an airy loft features plenty of windows and cathedral ceiling. Many improvements include updated electric & roof. Enjoy this lovely spot, with hiking trails to a fire pit for star-gazing. Peaceful location on quiet country road near York Lake(5min), Sandisfield State Forest (13 min), Riiska Brook Orchards(3min) for apple & blueberry picking. Inn on the Green and Gedney Farm(8 min),New Marlborough Reserve for hiking (7min,),Southfield Store for Coffee,Breakfast or Lunch (10 min) Butternut Ski Area (20 min) are just down the road. Escape to this terrific property!

Unique Opportunity! Lakefront on Center Pond. Original lake cabin built circa 1950 set on .79 acres with 100 feet of lake frontage. Located within 25 feet of the lake the structure will require extensive renovations. The cabin does have electricity and will need well and septic. Great spot and well worth the effort!

Welcome to the heart of Stamford, Vermont, where small-town charm meets endless opportunity. Set on 3.99 level acres with beautiful mountain views, this former historic general store has been transformed into a spacious 3,096 sq. ft. residence designed for today's flexible lifestyle. The main home offers 3 bedrooms, open living spaces, and room for everyone, while the separate second-floor apartment is perfect for extended family, Airbnb guests, a home business, or rental income. Spend summer days by the 28-foot inground pool, entertain under the picnic pavilion, relax on the deck, and enjoy parking for up to 8 vehicles. Just minutes from the Massachusetts border and downtown North Adams, you'll enjoy the best of Vermont living with easy access to everything you want!

Two property's for one Price, This rare Adams opportunity offers a beautifully updated two family and a single-family property next door--all on one purchase and move into ready The immaculate main home features a spacious bedroom, open living and dining areas, updated kitchen, laundry room, enclosed porch, 1.5 baths, vinyl windows, dry basement storage, and a one-car garage. Every major update has been completed, including roof, heating system, and mechanicals. The neighboring duplex offers two one-bedroom apartments with reliable long-term tenants, creating immediate income. It, too, has been meticulously maintained with updated systems and its own garage. Enjoy yards, ample parking, peaceful river views, and stunning views of Mount Greylock, all within walking distance to downtown Adam

Discover a rare New England Farmhouse located in the center of town built in 1890 and set on 4.06 acres. This character-filled Farmhouse offers 5 bedrooms and flexible living spaces, currently enjoyed as one home while retaining its two-family configuration. Spread out, welcome extended family, or create private guest space. Step outside to nearly 2 cleared acres with level pasture, electric service, a fenced garden with 6 raised beds, 10'x20' greenhouse, fruit trees and Concord grapes. Enjoy multiple covered porches plus a detached 2-car garage with unfinished loft and workshop or studio potential. Set back from Route 8 yet walkable to downtown and MASS MoCA, with a public park just across the way. Garden, gather, create and explore--bring your vision and make this unique property your ow

Discover a rare North Adams Multifamily homestead! Built in 1890 and set on 4.06 acres, this character-filled Farmhouse offers 5 bedrooms and flexible living spaces, currently enjoyed as one home while retaining its two-family configuration. Spread out, welcome extended family, or create private guest space. Step outside to nearly 2 cleared acres with level pasture, electric service, a fenced garden with 6 raised beds, 10'x20' greenhouse, fruit trees and Concord grapes. Enjoy multiple covered porches plus a detached 2-car garage with unfinished loft and workshop or studio potential. Set back from Route 8 yet walkable to downtown and MASS MoCA, with a public park just across the way. Garden, gather, create and explore--bring your vision and make this unique property your own!

Fabulous Indian Lakes Property.; Only about 8 homes down from the Lake. Fireplace for cozy nights. This 3 Bedroom 2 bath home has been completely remodeled. From new energy replacement windows, granite counter tops and stainless-steel appliances. Making it feel NEW. Wonderful large deck and a small screened in porch. The lay-out is perfect 2 BR and bath upstairs and 1 Br a bath and a nice family room downstairs walking out to a Berkshire back yard. The lower level has big windows a glass slider and nice big wood stove for extra warm heat in the winter. high speed fiber optics Easy to work from home.

Featuring a slate roof, classic architectural details, and modern interior updates, this versatile property is perfect for an owner-occupant looking for rental income or an investor seeking a turnkey Berkshire property. Sprawling Main Unit: Step into an extraordinarily spacious 4-bedroom, 2.5-bathroom primary residence featuring beautiful hardwood floors throughout. Enjoy the character of vintage interior details paired seamlessly with a completely updated kitchen and modernized bathrooms.Upstairs Unit: A bright and efficient 2-bedroom, 1-bathroom apartment complete with its own dedicated laundry--ideal for long-term tenants, a guest suite.

Welcome to this stunning two-family Victorian residence offering an exceptional blend of historical character and contemporary living. Featuring a slate roof, classic architectural details, and modern interior updates, this versatile property is perfect for an owner-occupant looking for rental income or an investor seeking a turnkey Berkshire property. Sprawling Main Unit: Step into an extraordinarily spacious 4-bedroom, 2.5-bathroom primary residence featuring beautiful hardwood floors throughout. Enjoy the character of vintage interior details paired seamlessly with a completely updated kitchen and modernized bathrooms.