Pittsfield, MA Homes for Sale under $300,000

Welcome to 27 Morgan Street, a bright and inviting home tucked away on a quiet dead-end street in Pittsfield.Natural light fills the main living spaces, highlighting gleaming wood floors and creating a warm, easy feel. The first floor offers a circular layout with a spacious, light-filled living room.Upstairs features three well-sized bedrooms and a full bath.Enjoy a charming front porch and a

Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

Some homes just feel right the moment you arrive. Sitting at the end of a dead-end street, 96 Boylston offers the kind of quiet and privacy that's hard to find this close to downtown Pittsfield. No through traffic, no neighbors driving past, just a peaceful street that's yours to enjoy.Step inside and you'll find a clean, modern interior that's been thoughtfully updated throughout. The kitchen is

Kyle Crocker eXp REALTY

Set at the end of a quiet dead-end street in the desirable north side, this home offers classic bungalow charm with the kind of layout that makes everyday living easy. Featuring a fireplace in the living room, a convenient first-floor bedroom and bath.Tucked away with added privacy, the driveway is accessed from Overfield--last home on the right--giving the property a unique and secluded feel.

Michele Purcell LAMACCHIA REALTY, INC

Enjoy this charming three-bedroom Cape-style home located in desirable Southeast Pittsfield. Gleaming hardwood floors run throughout most of the home. The first floor features a comfortable living room filled with natural light and a fireplace, a dining room, and a kitchen, along with a first-floor bedroom and full bathroom. Upstairs, you'll find two additional bedrooms, along with extra space

Jose Larios LAMACCHIA REALTY, INC

Location is a must! Spring cleanup is about to happen.Many improvements by current owners. Roof replaced in past 10 years. Orangeburg pipe replaced from house to street. Furnace replaced. Kitchen redone. Chimney pipe replaced.Just a few updates.

Deborah Dwyer DWYER AGENCY

Spacious and freshly updated West Side single-family offering 4 bedrooms and 2 full baths across 1,408 sq ft. Bright, functional layout with generous room sizes, fresh interior paint, and new laminate flooring throughout. Modern kitchen features brand-new appliances and clean, updated finishes. Enjoy a charming wraparound porch with dual entry, ideal for relaxing or entertaining, plus a level

Samantha Homeyer BIRCH PROPERTIES

Charming and affordable 2-story home near Pontoosuc Lake on the Pittsfield/Lanesborough line! This 2-bedroom, 1-bath home is ideal for a first-time buyer or weekend getaway in the Berkshires. Set on nearly an acre, it offers great outdoor space for relaxing, gardening, or future expansion. A flexible first-floor bonus room can serve as a guest room, den, or home office. Enjoy solar efficiency and

Holly Stracuzzi BISHOP WEST REAL ESTATE

Conveniently located just moments from downtown Pittsfield, this 3-bedroom, 1-bath home offers a straightforward, well-designed layout that works for everyday living. The open kitchen and dining area act as the center of the home, with plenty of space to gather, entertain, or simply move through your day with ease.An enclosed front porch creates a welcoming entry and adds flexible living space.

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

Welcome to 9 Lincoln Street, featuring white interior, hardwood floors throughout, large sun-filled rooms, and an open, flowing layout. The main level features a spacious living room, a bonus room that could serve as a first-floor bedroom, a dining room, and kitchen with direct access to a fully fenced backyard. Double doors open to an outdoor space ideal for relaxing or entertaining. Upstairs

Jessica Rizzo LAMACCHIA REALTY, INC

2 bedroom end unit condo offering the rare ease of true one level living, tucked in Churchill Crest's most private and peaceful building. This special home feels like a quiet Berkshire sanctuary, with a thoughtful layout that flows comfortably and welcomes you the moment you arrive. It's ready for your vision, character allows you to shape the space to your own style. Outside, enjoy a sparkling

Keyla Girard LAMACCHIA REALTY, INC

Absolutely beautiful double wide manufactured home situated on the south end corner of Allendale Pines North. 3 bedroom/2 bath home overlooking the woods with direct access to the Ashuwillticook Rail Trail! Sliding glass door of kitchen leads to private deck with no neighbors behind you!!

Val Whaling

This 3-bedroom, 2-bath home is a great starter opportunity. The flexible layout includes a convenient first-floor bedroom with two additional bedrooms upstairs. The living room and dining room have been freshly painted and feature new vinyl flooring. A spacious kitchen offers plenty of room for cooking and gathering. Outside, enjoy a fenced-in backyard and a detached one-car garage for added

Jim Thurston LAMACCHIA REALTY, INC

Two Family Flat fully rented in the Morningside Neighborhood! Each unit has three bedrooms and one bathroom. Updated kitchens and hardwood floors. Heat and hot water included. Washer and dryer hookups in the basement. Fully fenced in yard on a corner lot. Well maintained and ready for its new owner!

Derek Strzepa NOCHER REALTY

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

Timothy Johnson NOCHER REALTY

This lovingly lived-in home was once the heart of a bustling family of seven, where the conversations likely revolved around school schedules, family dinners, and plenty of sports. Filled with warmth, memories, and years of love, this 4-bedroom home is now ready for its next chapter. Recent updates include a brand new roof installed in 2026, fresh interior painting & wood floors . There is also a

Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

Conveniently located home offering more space than expected, with 4 bedrooms and 1.5 bathrooms. The main level features a bright living room, dining area, and kitchen, along with a full bath and bedroom or office option. Upstairs includes 3 additional bedrooms with great natural light. Mini split systems provide efficient heating and cooling, and solar helps offset electric costs. The lower level

THE KAHN TEAM BISHOP WEST REAL ESTATE

If you are looking for easy one-level living - don't miss this opportunity! The Maplewood is an elegant condo conversion consisting of eighteen units centrally located in downtown Pittsfield. You'll enjoy this light-filled corner/end unit on the first floor. High ceilings and an open-living plan give a very spacious feel to this two-bedroom unit. Kitchen with granite and stainless, hardwood

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

Welcome to 156 Chapel Street, a cozy & charming country retreat that instantly feels like home. This well-loved property offers 2 bedrooms and 1 full bath, with a warm living room centered around a pellet stove-perfect for crisp Berkshire evenings. The dining room serves as the heart of the home, ideal for gathering.The country kitchen is full of character, with a heated sunroom just off the

Jessie Downer LAMACCHIA REALTY, INC

Welcome to 9 Leslie Ave in Lanesborough, MA! This charming 2-bed, 1-bath bungalow offers easy single-level living with recent updates including new siding and gutters. The home features a comfortable layout with bright living spaces with a cozy, efficient footprint. Enjoy the added benefit of deeded lake rights, giving you convenient access to beautiful local recreation. Whether you're looking

Marci Levesque BISHOP WEST REAL ESTATE

Two-family home set on just under 1.5 acres offering the perfect blend of country living and city convenience. Each unit features decks overlooking a spacious backyard, ideal for relaxing or entertaining. Enjoy the privacy and open space while still being just minutes from city amenities, shopping, and dining. A great opportunity for owner-occupants or investors--live in one unit and rent the

Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

Absolutely beautiful double wide manufactured home situated on the south end corner of Allendale Pines North. 3 bedroom/2 bath home overlooking the woods with direct access to the Ashuwillticook Rail Trail! Sliding glass door of kitchen leads to private deck with no neighbors behind you!!

Val Whaling

This charming 3 bedroom and 2.5 bathroom condo is a must see! Offering fantastic location with scenic views of the swimming pool from your private deck. The bright and sunny kitchen seamlessly connect to the dining room making it perfect for entertaining. A Spacious living room features a wood burning fireplace. Additional features include one-car garage, storage closest and in-unit laundry for

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

Two family duplex just outside of downtown. Featuring two bedrooms and one bathroom in each unit with hardwood floors. Off Street parking and separate utilities.

Cory Evangelisto NOCHER REALTY

Perfectly situated on a spacious corner lot in a highly desirable neighborhood. This colonial style home is defined by its bright, airy atmosphere, featuring expansive windows that invite abundant natural sunlight into every room.The main level offers a seamless flow between the inviting living spaces and a convenient half-bath, while the second floor hosts three generous bedrooms and a full

Jason Nocher NOCHER REALTY

Welcome to easy, in-town living at sought-after One Colt Road in a charming neighborhood. This first-floor condominium offers the perfect blend of convenience and comfort, just a short stroll to Berkshire Museum, Colonial Theatre, local restaurants, and boutique shops. Featuring 2 bedrooms and 1 bath, the layout is both functional and inviting. A rare screened porch extends your living space,

Victoria Standring LAMACCHIA REALTY, INC

This two-family home was renovated in the last two years! Improvements include roof, windows, flooring, painting, and more! The home offers an enclosed front porch to access both units, and a side porch for each apartment independently. Each unit features living room, dining room, kitchen, 2 bedrooms and 1 bath. There is separate heat, hot water and electric: Unit 52 has natural gas heat while

Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.