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26 Photos
ROBERTS & ASSOC. REALTY, INC
$299,900
2 BD | 1 BA
Residential - Single Family

Stunning, completely renovated single-level home--just steps from Pontoosuc Lake--nestled on a private, dead-end street surrounded by woods. Perfectly located between Williamstown and Tanglewood, with Mount Greylock just minutes away. Move-in ready with updated roof, electrical, and plumbing; a high-end kitchen featuring stainless appliances and quartz countertops. Thoughtful one-floor layout includes two bedrooms, full bath, and convenient in-home laundry.


9 Photos
HOUSATONIC REAL ESTATE
$460,000
2 BD | 2 BA
Residential - Single Family

Nestled on a quiet setback lot in the desirable Housatonic Village of Great Barrington, this beautifully renovated home (2021) offers a perfect blend of charm, comfort, and flexibility. The property features 2 bedrooms, a bonus room, and 1.5 baths.Recent upgrades include a new roof, new windows, beautiful wood floors throughout the first and second levels. The thoughtfully updated kitchen boasts modern appliances, while the renovated full bath upstairs and newly added first-floor half bath provide everyday convenience.A finished third-floor space adds valuable extra living area and may serve as a third bedroom, home office, or studio. Enjoy scenic Berkshire views, a fenced front and side yard, and a welcoming front porch. More pictures to follow!


54 Photos
NOCHER REALTY
$469,900
4 BD | 3 BA
Residential - Single Family

Discover the perfect blend of modern style and effortless living in this stunning contemporary-style Ranch. Nestled on an expansive lot within one of Pittsfield's most sought-after neighborhoods, this home offers a rare combination of space, light, and a sophisticated layout. Sun-Drenched Interiors: light inviting windows throughout the home allow an abundance of natural light, creating a warm and vibrant atmosphere in every room. Spacious Living Features four generous bedrooms and two and a half baths, there is plenty of room for family, guests, or a dedicated home office. Closing credit allowance for refinishing the wood floors under carpeting.


15 Photos
STONE HOUSE PROPERTIES, LLC
$285,000
3 BD | 1 BA
Residential - Single Family

Charming Southeast ranch located on a quiet street in one of Pittsfield's most desirable neighborhoods. This well-maintained 3-bedroom, 1-bath home was completely rebuilt from the studs in 2004, offering peace of mind with updated systems throughout. Enjoy easy one-level living with a comfortable layout and abundant natural light. Step outside to a nicely fenced backyard featuring a newer deck, perfect for relaxing or entertaining. A wonderful opportunity for first-time buyers, downsizers, or anyone seeking a move-in-ready home in a sought after Southeast location


33 Photos
RE/MAX COMPASS
$329,900
1 BD | 1 BA
Residential - Single Family

Welcome to your Berkshires escape in desirable East Otis! Built in 2012, this well-maintained Cape offers comfort, efficiency, and low-maintenance living--ideal as a weekend retreat, year-round home, or investment opportunity--with deeded Otis Reservoir access. Inside, enjoy a bright open-concept layout that lives larger than its ~864 sq ft, featuring a spacious 1-bedroom, 1-bath design supported by a 2-bedroom septic. Modern touches and cozy charm throughout. Set on a private, easy-care quarter-acre lot with a peaceful wooded backdrop--perfect for relaxing after a day outdoors. Just a short walk to Otis Reservoir for boating, fishing, and kayaking, plus year-round recreation across the Berkshires.


37 Photos
LAMACCHIA REALTY, INC
$348,000
3 BD | 1 BA
Residential - Single Family

Move in ready! This is a well-cared-for property offering lake rights and a long list of meaningful improvements spanning nearly two decades. Inside, you'll find a home that's been continuously upgraded with a remodeled kitchen and bathroom, updated windows, including a bright bay window in the living room. Both the boiler and roof have been replaced. The three-season room adds flexible living space and connects seamlessly to the back porch--perfect for relaxing or use as a home office. The entry ramp leads into a mud room that connects the house, garage and back porch.


47 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$650,000
5 BD | 4 BA
Residential - Single Family

Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an open concept kitchen and family room with cathedral ceilings, where sliders lead seamlessly to a large rear deck overlooking a spacious, flat, and fenced backyard; ideal for gatherings, play, or quiet relaxation amid mature landscaping and beautiful gardens.


14 Photos
DWYER AGENCY
$390,000
2 BD | 2 BA
Residential - Single Family

Beautifully maintained 2 bedroom brick ranch featuring gorgeous wood floors throughout. The inviting living room showcases a cozy fireplace & flows seamlessly into the formal dining room. The remodeled kitchen offers many cabinets & counter space.A bright & sunny room overlooks the fully fenced rear yard & provides direct access to the deck - ideal for relaxing or outdoor gatherings.The finished lower level adds even more living space with a fireplace, spacious family room & bar area. Perfect for entertaining or cozy nights at home.


44 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$2,250,000
3 BD | 3 BA
Residential - Single Family

Set just off the shoreline of Onota Lake and accessed by a private bridge, this approximately 1.25-acre island offers a kind of ownership that is seldom available in the Berkshires.Surrounded by water, the property creates a natural sense of separation and calm, with broad lake views and a level of privacy that is difficult to replicate without sacrificing accessibility. Here, the experience is distinctly your own, yet the mainland is always within easy reach.The existing residence is positioned to take full advantage of the setting. A vaulted living space with a loft above, two fireplaces, and expansive windows and sliders bring in light and water views throughout the day. A covered porch extends directly toward the lake, offering a simple, immediate connection to the outdoors.


25 Photos
BISHOP WEST REAL ESTATE
$175,000
3 BD | 2 BA
Residential - Single Family

Welcome to 26 Crosier Ave--charming character meets creative opportunity!Nestled in the heart of Pittsfield, this delightful colonial-style home offers a bright, spacious layout with classic charm! With 3 bedrooms and 2 baths, cozy living room, a functional kitchen, and generously sized rooms filled with natural light. The unfinished third-level space whispers ''potential,'' while the off-street parking and sunny porch add convenience and curb appeal. While this home has been lovingly maintained, it does need some cosmetic refresh--think fresh paint, updated fixtures, and modern touches to let its personality truly shine.


60 Photos
PAULA MCLEAN REALTORS INC.
$1,350,000
4 BD | 5 BA
Residential - Condo/Townhouse

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite--pool, fitness center, clubhouse, and tennis--all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.


56 Photos
PAULA MCLEAN REALTORS INC.
$1,350,000
4 BD | 5 BA
Residential - Single Family

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite--pool, fitness center, clubhouse, and tennis--all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.


26 Photos
NOCHER REALTY
$229,000
2 BD | 2 BA
Residential - Single Family

Exceptional Investment Opportunity: Versatility & Prime LocationDiscover a property that offers unparalleled flexibility in one of Pittsfield's most active commercial corridors. Situated on a sprawling 0.92-acre lot directly across from Berkshire Crossing, this unique property presents a rare ''blank canvas'' for homeowners and investors alike. Currently configured for mixed-use with a professional office space on the main level and a spacious 2-bedroom apartment on the second floor. Easily convertible back into a large Single-Family home for those seeking significant acreage and convenience in the heart of town.


43 Photos
PAULA MCLEAN REALTORS INC.
$425,000
2 BD | 3 BA
Residential - Single Family

Classic New England farmhouse featuring a charming kitchen with beautiful Berkshire views and an open, inviting layout perfect for entertaining. The 1st floor offers, full bath and convenient laundry hookups, along with 2 living rooms. One ideal for relaxation and the other a perfect home office, playroom, game room. Upstairs, you'll find 2 good sized bedrooms each with their own full bathroom for ultimate comfort and privacy. Outside a 2 car garage great for snow days or storing an old vintage car! Ideally located close to Tanglewood, Ventfort Hall, Bousquet Mountain & Sport, The Colonial Theatre as well as wonderful restaurants, cafes, and shopping. A little something for everyone.


27 Photos
WILLIAM RAVEIS - BERKSHIRE
$445,000
3 BD | 1 BA
Residential - Single Family

Enjoy one-level living in downtown Great Barrington! This charming 3-bed, 1-bath mid-century ranch is your perfect Berkshire retreat, featuring a cozy wood stove in the living room for those crisp mountain evenings. Nestled on a quiet cul-de-sac, the home sits on a spacious 0.41-acre lot with mature trees. Features include an attached 2-car garage/workshop, large private yard, original wood floors, and an updated heating system. The real gem? Unique B2 zoning allows for a home business, studio, or office! Enjoy an unbeatable location--walk to shops and dining, with downtown and attractions like Tanglewood and Butternut just minutes away. This versatile property is a rare find offering both a peaceful home and a prime business opportunity.