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31 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$145,900
4 BD | 2 BA
Residential - Single Family

This cherished home has 4 bedrooms, 1.5 bathrooms. Features hardwood floors and luxury vinyl flooring, with plenty of sunlight streaming through, adding a touch of comfort. On the first floor, you'll find a warm living room, a cozy dining area, updated kitchen, full bathroom with laundry, and a flexible first floor bedroom or home office to suit your needs. Upstairs, there are three bedrooms and a half bath, providing plenty of space. Enjoy peaceful moments on the spacious deck overlooking your private backyard. Newer roof, water heater, and replacement windows throughout. Prime downtown Pittsfield location, near restaurants, museums, hospitals, and more Berkshire attractions. This charming home is the opportunity you've been waiting for!


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Discover the perfect blend of tranquility and convenience with this exceptional cleared building lot in a picturesque country setting. Boasting seasonal views and situated within a peaceful association of beautiful homes, this property is an ideal getaway spot for your dream country home.With a drilled well and a leach field for a 3-bedroom septic system installed within the last three years, you can build with confidence knowing the essential infrastructure is already in place. Stay connected with high-speed internet available through fiber optics, ensuring modern convenience in your serene retreat.Just a 20-minute drive from the vibrant town of Great Barrington, you'll have easy access to shopping, dining, & cultural attractions while enjoying the peace and quiet of the countryside.


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NON-MEMBER / RECIPROCAL
$179,900
3 BD | 1 BA
Residential - Single Family

Step into this delightful home, where classic charm meets modern convenience! Newly uncovered hardwood floors and original wood beams infuse warmth into the living and dining areas. Upstairs, tandem bedrooms create flexible living options, potentially transforming this into a three-bedroom retreat or offering private work-from-home space. A newly renovated bathroom, new windows (2022), and updated appliances ensure comfort and efficiency. Looking for extra space? The area above the garage is an opportunity waiting to unfold--ideal for an artist's studio, loft, or workspace. Located in the breathtaking Berkshires, you're surrounded by mountain scenes that change with each season. Just 2 minutes to Mass MoCA and North Adams Regional Hospital, 5 minutes to MCLA, and 10 minutes to Williams.


33 Photos
NOCHER REALTY
$229,000
6 BD | 2 BA
Multi-Family

Centrally located 2 family, side by side duplex! This 6 Bed / 2 Bath property offers spacious rooms throughout, replacement windows, off street parking, newer boilers & water heaters and 1st floor laundry rooms. Walking distance to downtown Pittsfield and Berkshire Medical Center makes this a great investment property.Along with the possibility to owner occupy with the existing vacant unit.


41 Photos
LAMACCHIA REALTY, INC
$239,900
3 BD | 1 BA
Residential - Single Family

Better than renting, a chance to own an affordable home in a central location. Motivated sellers! Charming and light-filled Colonial in a highly desirable Southeast Pittsfield neighborhood. This inviting home offers 3 bedrooms and 1 full bath, a welcoming layout, and an abundance of natural light. Recent updates include a brand-new sewer line, brand new living room carpet, a newer roof and boiler, adding comfort and peace of mind. Enjoy the convenience of a rear deck perfect for relaxing or entertaining, an easy-to-maintain yard, and a shared driveway. Ideally situated with sidewalks leading to parks, restaurants, salons, hardware, pharmacy and convenience stores. A wonderful home in a prime location, ready for its next chapter and just in time for the New Year!


19 Photos
LAMACCHIA REALTY, INC
$249,900
2 BD | 1 BA
Residential - Single Family

Don't miss this charming 984 sq. ft. ranch, lovingly maintained by the same owners for over 20 years! Featuring 2 bedrooms and 1 full bath, this home offers the ease of single-level living with a bright, open layout perfect for relaxing or entertaining. The cozy kitchen flows into dining and living areas, while the attached garage provides convenience and extra storage. Step outside to a manageable yard that's just right for gardening, gatherings, or enjoying the seasons. Whether you're a first-time buyer, looking to downsize, or ready for a low-maintenance lifestyle, this move-in ready home combines comfort, charm, and practicality--all in one inviting package!


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BISHOP WEST REAL ESTATE
$250,000
3 BD | 1 BA
Residential - Single Family

Welcome home to this move-in ready Cape-style gem offering comfort, convenience, and classic New England charm. This well-maintained home features 3 bedrooms--including two on the first floor for easy living--and one full bath.Step inside to find a warm and inviting layout with plenty of natural light throughout. The spacious backyard is perfect for gardening, entertaining, or simply relaxing outdoors.Located in a convenient area close to Berkshire Medical Center, Pontoosuc Lake, local shops, and restaurants, this home offers the perfect blend of suburban tranquility and easy access to all the essentials.Don't miss your chance to own this delightful property--move right in and make it your own!


14 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Lots of preparation work went into this building lot with a handsome meadow and dramatic ledge formations with large pockets of cool ferns. Some western views and a north east field stone wall. Almost 2 acres. Old well in place. Excellent percolation test results with 1 inch per min. Curb cut. Ready to build.


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RE/MAX COMPASS
$259,500
2 BD | 1 BA
Residential - Single Family

Cozy home with a wood stove for the perfect winter retreat, close to snowmobile trails, and 30-40 minutes from fabulous restaurants, 3 ski areas and land for hunting, only a few miles to 3 beautiful lakes, Plunkett, Ashmere and Garnett. (Garnett is within walking distance with private beach). Swimming, kayaking, canoeing and fishing with ice fishing in the season. Almost 5 acres of the most peaceful, serene and nature filled setting. Wildlife. Make this your primary residence, second residence or an Air BnB. 10 cords of log length seasoned wood to be left for buyer. Updated bathroom, 2-year new deck with sliders from kitchen. This can be your oasis.


38 Photos
BIRCH PROPERTIES
$265,000
2 BD | 1 BA
Residential - Single Family

125 Hancock Road sits directly across from Pontoosuc Lake Park, offering peaceful views of the water and an easy connection to one of Pittsfield's most loved recreational areas. This bright and welcoming home enjoys lovely natural light throughout the day, with both the living room and dining room capturing views toward the lake and surrounding hills.Inside, the main level has an open and comfortable flow. The living room and dining room connect seamlessly, and the adjoining sitting room features a wood stove -- an inviting place to settle in on winter evenings. The kitchen offers warm cabinetry, stainless appliances, and a view over the backyard, linking easily with the home's main living spaces. A first-floor bedroom with soft natural light and a full bath complete this level.


3 Photos
STONE HOUSE PROPERTIES, LLC
$268,500
3 BD | 3 BA
Multi-Family

Spacious three-family home in the heart of Pittsfield's vibrant Downtown Cultural District! This property features a total of 3 bedrooms, offering strong rental potential and versatility. Recent capital improvements include newer roof and siding, reducing immediate maintenance costs and boosting curb appeal. Situated in a highly desirable, walkable location near restaurants, the Berkshire Carousel, galleries, theaters, shopping and public transit, this property is perfectly positioned for both appreciation and consistent cash flow.Whether you're expanding your portfolio or entering a high-demand market, this is a rare opportunity to secure a multi-family asset in one of the city's most dynamic and culturally rich neighborhoods. Don't miss out--schedule your private showing today.


32 Photos
LAMACCHIA REALTY, INC
$269,000
3 BD | 2 BA
Residential - Single Family

Opportunity awaits near Pontoosuc Lake! This solid ranch-style home offers great bones and endless potential on a generous double lot just moments from lake access. Featuring 3 bedrooms and 1.5 baths, the layout is practical and inviting, ready for your personal touch. A spacious living room, eat-in kitchen, and convenient single-level living provide a strong foundation for renovation or re-imagination. Step outside to a large deck overlooking the yard. The oversized garage offers plenty of space for vehicles, storage, or a workshop. With its prime location near boating, fishing, and recreation, this property is ideal for year-round living or a weekend getaway. Bring your vision and make this home shine!


29 Photos
LAMACCHIA REALTY, INC
$269,900
2 BD | 1 BA
Residential - Single Family

Cute as a button! Welcome to 90 Cheshire Road! This 2 bedroom , 1 bath ranch is turnkey and move in ready! Tastefully updated with some of the updates including newer Kitchen & Bath amongst many others. The convenient layout is perfect for someone looking for single level living! On the exterior you will find a recently paved driveway and walkway, shed and a fenced in area complete with gazebo. This home has been meticulously maintained and it shows. You won't want to miss this opportunity for a ranch style home close to shopping, restaurants and all that Pittsfield has to offer.


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BISHOP WEST REAL ESTATE
$272,000
6 BD | 2 BA
Multi-Family

Recently Renovated Two-Family Flat - Lead Compliant & Move-In Ready!Discover this nicely updated two-family flat offering comfort, convenience, & modern features. Lead compliant, this property is perfect for owner-occupants or investors alike.Each 3 BR unit boasts fresh finishes & functional layouts!. The fully fenced yard is ideal for pets, play, & entertaining, & the two-car garage provides secure parking & extra storage.Located within walking distance to schools & in a convenient location with a new (2022) sewer line & ramp for easy accessibility. This property checks all the boxes!Schedule your showing today & see why this opportunity won't last!


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NOCHER REALTY
$279,900
3 BD | 1 BA
Residential - Single Family

Move in ready 3 Bedroom / 1 Bath Ranch in Southeast Pittsfield. This home really checks all of the boxes, single level living, attached garage, perfect sized flat yard, screened in back patio, wood burning fireplace, desirable neighborhood, fully furnished, finished basement, hardwood floors and so much more. Welcome Home!!


29 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$279,900
2 BD | 1 BA
Residential - Condo/Townhouse

Welcome to Modern One Level Easy Living at Churchill Crest Condominiums. This unique offering has been meticulously updated and finished with new and improved features in each room. Enter spacious living room with expansive newer slider framing front to back views. Bousquet mountain out front and to rear see the rear patio, privacy, woods and beautiful custom landscape that has evolved from over 25 years of ownership. New cabinet kitchen topped with quartz and equipped with stainless sets a cozy table for two and a view of the center courtyard with rolling green lawns by Summer and peaceful and comfortable stroll to front door by winter. Primary bedroom faces the wooded border for privacy and quiet by night. Remodeled bath finishes the updates throughout.


42 Photos
LAMACCHIA REALTY, INC
$289,900
3 BD | 2 BA
Residential - Single Family

Welcome to this super cute and spacious 3-bed, 2-bath home nestled in desirable neighborhood. Inviting layout and thoughtful updates throughout. This home perfectly balances modern comfort and classic charm. Remodeled kitchen features stylish cabinetry, stainless steel appliances, a sleek tile backsplash, and marble-look countertops. Open dining area with built-ins connects seamlessly to the bright living room, where a large picture window fills the space with natural light. The refinished lower level offers a versatile bonus area complete with a bar setup and modern full bath, perfect for a family room, home office, gym, or guest suite. A separate updated laundry room adds convenience and organization. Enjoy the expansive yard -plenty of space for outdoor dining, gardening or relaxing


22 Photos
ROYAL PROPERTY GROUP
$299,900
3 BD | 1 BA
Residential - Single Family

Welcome to 121 Edward Avenue, an updated home in desirable Southeast Pittsfield offering a rare blend of move-in-ready improvements and classic character. The property features a one-car detached garage and a large yard, providing excellent outdoor space and functionality. The owner has completed extensive upgrades including brand-new roofs on both the house and garage, a new high-efficiency furnace, newly sanded and refinished floors, and fresh paint throughout the home, including the basement. The kitchen has been updated, and numerous interior and exterior repairs have been addressed, allowing the next owner to move in with confidence. This is a well-maintained home that delivers strong value in today's market.


31 Photos
KELLER WILLIAMS REALTY
$299,900
3 BD | 2 BA
Residential - Single Family

Rare opportunity to own a well maintained home offering a large yard with plenty of wooded area along with a convenient central location! Offering three bedrooms including one on the first floor. Upstairs bedroom has a built-in dresser and desk. Has two full bathrooms, family room, living room with built-in bookcase and cabinets, recreational room, and an office that could be converted into a fourth bedroom. Combined dining area and galley kitchen, laundry area on first floor, and plenty of closet space. Two car detached garage, deck and perennial gardens. Roof on the main portion of the house was replaced in 2025 and many replacement windows are throughout. Additional buildable lot available Parcel ID I11-0019-004 MLS listing 248337 to increase acreage to just over an acre.


7 Photos
THE KINDERHOOK GROUP - PITTSFIELD

Just shy of 20 acres. Make your way to the top for views, you won't be disappointed. An abundance of wildlife, and not a building in sight. Come take a look and make this your Berkshire retreat!

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