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38 Photos
Lamacchia Realty, Inc. - Dalton
$284,900
3 BD | 1 BA
Residential - Single Family

Welcome home to 68 Doreen Street! This inviting 3-bedroom, 1-bath ranch offers comfortable one-level living in one of Pittsfield's most desirable neighborhoods. The spacious eat in kitchen features granite counter tops and stainless steel appliances and opens nicely into the living room. Step outside to discover a truly special private backyard, beautifully enclosed with a full fence and designed for relaxing and entertaining. Enjoy two spacious decks, unwind in the hot tub, or take advantage of the shed for extra storage. A one-car detached garage adds convenience and functionality. With its welcoming feel, fantastic outdoor space, and desirable location, this home is ready to create years of wonderful memories!


14 Photos
WILLIAM RAVEIS - BERKSHIRE
$285,000
5 BD | 3 BA
Multi-Family

Opportunity awaits! This three-unit property is situated on a large lot and offers excellent potential for an owner-occupant or investor. Two of the three units are currently rented, providing immediate rental income, while the additional unit offers flexibility for occupancy or future rental. A detached two-car garage provides valuable parking and storage space, and the generous yard adds to the property's appeal. Conveniently located near shopping, dining, schools, and other Pittsfield amenities. A great opportunity to add a multi-family property with income potential to your portfolio!


64 Photos
Lamacchia Realty, Inc. - Dalton
$287,000
5 BD | 3 BA
Multi-Family

Offered for the first time in 67 years! Lovingly cared for by the same family since 1959, this well-maintained two-family home is filled with history and potential. Originally built as a single-family residence and later converted into two separate living spaces, the property offers a spacious two bedroom unit on the first floor and a three bedroom unit upstairs. Pride of ownership shines throughout this exceptionally clean and well-kept home. Enjoy the beautiful rear deck with seasonal awning, along with the convenience of off-street parking and a two-car garage. The first-floor unit will be delivered vacant at closing, while the second-floor unit is currently occupied, with vacancy anticipated on or about 12/1/26. An excellent opportunity for owner-occupants and investors alike!


17 Photos
Lamacchia Realty, Inc. - Dalton
$289,000
3 BD | 1 BA
Residential - Single Family

Welcome to this 3-bedroom, 1-bath Cape located in Southeast Pittsfield. The home features a spacious kitchen with wood cabinetry, gas heat and hot water, and a new roof installed in 2023. Conveniently located on Williams Street, just minutes from shopping, dining, recreation, and many of the cultural and outdoor attractions the Berkshires has to offer. A great opportunity to enjoy comfortable living while being close to all that Pittsfield and Berkshire County have to offer.


36 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$289,900
3 BD | 1 BA
Residential - Single Family

Easy living, smart updates, and the feeling that you can simply move in and enjoy. This one-level ranch delivers where it matters most with a new roof, new heating system, beautiful wood floors, updated cabinetry and gorgeous solid-stone countertops. An attached garage and screened room add to the everyday appeal, while the level, manageable backyard offers just the right amount of outdoor space without the upkeep. The basement provides plenty of storage and additional usable space for whatever life calls for next. A stand-out in this price point, with the big-ticket improvements already completed-offering the kind of value, comfort, and peace of mind to be appreciated for years to come!


32 Photos
ROBERTS & ASSOC. REALTY, INC
$295,000
3 BD | 1 BA
Residential - Single Family

Welcome to this charming, updated ranch tucked into a quiet neighborhood and conveniently located near shopping and restaurants. Enjoy the ease of single-level living with thoughtful updates throughout. Recent improvements include an updated bathroom, new driveway (2026), siding and Trex deck (2025), and furnace (2018), with the roof replaced in 2011. Move right in and enjoy a comfortable home with a great combination of updates, convenience, and low-maintenance living.


40 Photos
WILLIAM RAVEIS - BERKSHIRE
$299,900
3 BD | 1 BA
Residential - Single Family

Full of charm and potential, this 3-bedroom, 1-bath home is ready for its next chapter! Clean and well maintained with many updates, the home offers an easy-flowing living space, while the sun-filled porch is a welcoming spot to relax and enjoy your morning coffee. Step outside to the small deck, perfect for grilling or unwinding at the end of the day. The finished lower level provides flexible bonus space, and the two-car garage offers plenty of room for storage and a workshop. A brand-new sewer line adds even more peace of mind. Comfortable and inviting as it is, with just a few personal touches this charming home could truly shine!


59 Photos
CENTURY 21 NORTHEAST
$299,900
3 BD | 2 BA
Residential - Single Family

OPEN HOUSE CANCELLED 9/19 Well maintained and cared for over the years, this home offers plenty of character and space. Step through the beautifully refreshed front entry into a spacious living room or parlor and a kitchen with doors leading to the wrap around rear deck. The downstairs features beautiful hardwood floors and a full first floor bathroom with washer and dryer. Upstairs are three carpeted bedrooms, including a spacious primary, along with a second full bathroom. Outside, enjoy the deck with a well maintained yard and fenced in in-ground pool. A brand new roof in place, a one car garage and a full basement for storage. Located on a dead end street, you'll feel tucked away while still being close to downtown!


67 Photos
Lamacchia Realty, Inc. - Dalton
$299,900
4 BD | 3 BA
Residential - Single Family

OPEN HOUSE Sat 10/31 10:30a-12:00p. Enjoy the perfect blend of convenience, privacy, and versatility in this spacious Pittsfield home! Ideally located close to town yet tucked away in a peaceful, private setting, this property features a generous yard with mature, manicured landscaping and a spacious deck perfect for outdoor entertaining or simply relaxing. Originally built as a two-family residence and thoughtfully converted into a single-family home, the property remains listed as a two-family in city records, offering exciting possibilities for future use. With 3+ bedrooms, 4 bathrooms, two staircases, and beautiful original yellow pine floors, this home provides an abundance of space and flexibility for extended or multigenerational living.


32 Photos
Lamacchia Realty, Inc. - Dalton
$309,000
3 BD | 1 BA
Residential - Single Family

Welcome to this bright and inviting 3-bedroom, 1-bath ranch, ideally located just moments from beautiful Pontoosuc Lake on a spacious double lot. This home features a generous living room with oak hardwood floors, a formal dining room, and an updated kitchen with newer countertops. Additional highlights include a spacious basement with abundant storage, an oversized one-car garage, and an enclosed seasonal porch-the perfect place to relax. The fully fenced backyard offers plenty of space for gardening, entertaining, pets, or simply unwinding. Conveniently located near the lake, shopping, dining, and local amenities, this home offers the perfect blend of comfort, convenience, and outdoor living. Enjoy the convenience of living just moments from Pontoosuc Lake Park, where boating,


28 Photos
Lamacchia Realty, Inc. - Dalton
$309,900
3 BD | 1 BA
Residential - Single Family

Fall in love with this beautifully renovated Ranch offering easy, one-level living in a lovely neighborhood. The gleaming hardwood floors throughout, a spacious and sleek new kitchen with quartz counters, a stylishly renovated bath, three comfortable bedrooms, and a bright welcoming layout. The unfinished walkout basement offers excellent potential for additional living space, home office, gym, or recreation room. Enjoy the ultra private location at the end of the street, and the beautiful private retreat that is your dreamy backyard. Updated electric heat and new on demand hot water provides efficient and comfortable warmth throughout the home. Conveniently located near Berkshire Hills Country Club, Allendale and Berkshire Crossings shopping centers. Move right in and enjoy!


44 Photos
Lamacchia Realty, Inc. - Dalton
$314,900
3 BD | 2 BA
Residential - Single Family

Welcome home to this well-maintained ranch offering the ease & convenience of one-level living! Inside, you'll find beautiful hardwood floors & a large dining room that's perfect for entertaining. The kitchen & two of the 3 bedrooms are enhanced by skylights, which fill the spaces with abundant natural light. The first floor also features a stackable washer & dryer & cedar-lined closets. The finished basement provides valuable additional living space, ideal for a family room, home office, or gym. Outside, enjoy the fully fenced backyard, dedicated workshop, two storage sheds, a deck & two awnings for shade. Additional highlights include efficient natural gas heat & a solar hot water system to help reduce energy costs. Enjoy the perfect blend of neighborhood living just minutes from Lenox.


20 Photos
Lamacchia Realty, Inc. - Dalton
$315,000
3 BD | 2 BA
Residential - Single Family

Welcome to 84 Lillian St., a charming 3-bedroom, 2-bath home situated on a corner lot in Southeast Pittsfield. Warm wood floors add character throughout the comfortable and inviting living spaces. The home offers three bedrooms, a garage, and a full basement with a bathroom, providing excellent potential for additional living, recreation, workshop, or storage space. The corner lot offers a nice sense of openness and outdoor space. Conveniently located near shopping, dining, schools, and all that the Berkshires have to offer. A solid home with plenty of opportunity--come see the possibilities and make it your own!


42 Photos
Lamacchia Realty, Inc. - Dalton
$320,000
3 BD | 2 BA
Residential - Single Family

Charming brick Cape offering the convenience of first-floor living! The main level features two bedrooms and a full bathroom, for comfortable everyday living. Upstairs you'll find an additional bedroom, full bathroom, and a spacious open concept-area offering endless possibilities. With a flexible floor plan, there is also potential for a fourth bedroom. Additional highlights include beautiful hardwood floors, a cozy wood-burning fireplace, a sunroom leading to a rear deck, and a one-car garage underneath. This home offers endless possibilities for its next owner!


55 Photos
NOCHER REALTY
$325,000
5 BD | 3 BA
Residential - Single Family

Discover urban living at its finest in the heart of Pittsfield with this striking, one-of-a-kind Mansard-style brownstone. Spanning three levels, this 5-bedroom, 2.5-bathroom townhouse seamlessly blends historic architectural character with modern convenience. Soaring 11-foot ceilings, striking exposed brick accent walls, vintage hardwood floors running throughout, and a classic fireplace (decorative) anchor the main living spaces with warmth and distinction. A stunning, curved original staircase serves as a dramatic architectural centerpiece, winding gracefully upward from the main level to both the second and third floors.The main level features a convenient half bathroom, while the upper levels house 5 generously proportioned bedrooms,


52 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$329,900
3 BD | 1 BA
Residential - Single Family

A Little Whimsy, A Lot of Wow! Step into a bungalow bursting with personality, where timeless Craftsman charm meets thoughtfully curated updates, playful color, and extraordinary style! Beautifully reimagined while preserving its solid bones and original character, this home is anything but ordinary. A gorgeous new kitchen with stainless steel appliances and an island flows into a darling butler's pantry and beautiful dining room. The inviting living room steals the show with its oversized fireplace and rich Craftsman woodwork. Generously sized bedrooms offer incredible closet storage, while an updated bathroom and convenient mudroom add everyday practicality. The enchanting front porch is made for reading, writing, dreaming, and watching the world go by.


43 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$339,900
2 BD | 1 BA
Residential - Single Family

Enjoy easy one level easy living in this sought after southeast tree-lined street with homes built of brick or stone creating a New England picture perfect neighborhood. See the updated kitchen, and bath, manageable two bedrooms with unfinished attic space for more in the future. Outfitted with central air conditioning for cooling comfort at your pleasure. A surprisingly large back yard all fenced in for privacy, shade trees, stone patio and firepit for fun fall nights with marshmallow roasting. Enter first onto the covered front porch where you sit and either enjoy a coffee or visit with passer bys hearing church bells in the distance. Enter an inviting dedicated entryway with a unique opening to peer into the fireplaced living room. The stone fireplace achors the room


10 Photos
NOCHER REALTY

Create your Berkshire home at 1 Thrushwood Lane in Great Barrington. Located within a development, this ready-to-build lot offers access to utilities and the opportunity to bring your vision to life. Whether you imagine a year-round residence or a Berkshire getaway, bring your plans and create a home that reflects your style in this Great Barrington setting.


40 Photos
Lamacchia Realty, Inc. - Dalton
$349,000
3 BD | 2 BA
Residential - Single Family

Motivated Seller! 1121 North St is a well-cared for home offering comfort, convenience with classic style and some modern updates. Fully fenced backyard. Perfect for pets, gardening, entertaining or relaxing in your own private retreat. Unwind in the bright sunroom with its own gas fireplace for chilly evenings and winter days. The oversized garage opens to a mudroom. Updated kitchen and a half bath on the first floor. Wood floors in dining and living area. Walk in closets. Easy access to routes in and out of the Berkshires. Just outside of downtown, yet close to medical facilities, shopping, dining, Pontoosuc Lake, outdoor recreation, cultural activities as well as local ski areas. Come experience the warmth, charm and lifestyle that make this a wonderful place to call home.


39 Photos
ROBERTS & ASSOC. REALTY, INC
$349,900
3 BD | 2 BA
Residential - Single Family

Enjoy the best of Berkshire living in this beautifully updated 3-bedroom, 2-bath home, tucked away in a private setting at the top of a hill near Pontoosuc Lake. The stunning kitchen features a farmhouse sink, granite countertops, and an island perfect for entertaining. An open floor plan and new engineered hardwood floors throughout create a fresh, inviting feel. Sliders lead to a deck overlooking the spacious yard, offering room to relax, entertain, and enjoy the outdoors. Take in the beauty of the Berkshires while enjoying a sense of privacy, all in a convenient location close to Pontoosuc Lake and the outdoor recreation the area has to offer.

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