1,897 houses for sale in Berkshire County

Incredible Multi-Unit Investment Opportunity in Downtown Pittsfield! Located just steps from the Barrington Stage Company theater in the heart of the cultural district, this dynamic property includes 3 apartments, making it a true income-generating powerhouse. This is a rare opportunity for both the savvy investor and the live-in owner looking to offset housing expenses. The entire property has been newly renovated and is in excellent condition, offering peace of mind for years to come. Each unit has been thoughtfully updated with modern finishes, efficient systems, and attention to detail, making it a turn-key investment with minimal maintenance needs. There are 2 units on the 1st floor (front and back) that are 1 bed/1 bath each, plus the 2nd floor hosts a 2-bed/2 bath on the 2nd level

20 Marietta St, North Adams is fully renovated, move-in ready, and packed with value. This spacious 5 bedroom, 2 full bath home has been completely redone from top to bottom. Featuring a brand new roof, all new appliances, updated kitchen and bathrooms, and new flooring throughout, every detail has been taken care of. Clean, modern finishes give the home a fresh feel while maintaining a practical, functional layout. With ample living space and a garage for added convenience, this property is ideal for larger households, first-time buyers, or anyone looking for a true turnkey home. FHA and VA buyers welcome, making this an easy and accessible opportunity to own a fully updated property without the hassle of renovations. Everything has been done, just move in and enjoy

Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence and generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette and massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard and patio, separate studio apartment and 4 garage bays, a barn, and cutting gardens. The custom home, built by one of the region's premiere builders, has been featured in design magazines, garden tours and has received a Garden Club of America award for its ethos and thoughtful use of b

Prime investment opportunity in a highly desirable location just steps from the post office and within walking distance to downtown amenities, shopping, dining, and services. This well-maintained four-family property offers strong income potential with all separate utilities, allowing tenants to pay their own expenses and helping to maximize owner returns. Recent capital improvements include a new roof installed in 2022 and two high-efficiency gas furnaces added in 2023, providing peace of mind for years to come. Each unit features washer and dryer hookups, while newer hot water boilers, vinyl replacement windows, and low-maintenance vinyl siding contribute to reduced operating costs and enhanced efficiency. Tenants will appreciate the private paved parking area and detached two-car garage. a rare amenity in such a convenient in-town location. Whether you're expanding your portfolio or seeking a turnkey multi-family investment, this property offers an excellent combination of location,

This 3-bedroom, 2-bath ranch sits on a quiet street in one of Pittsfield's most desirable areas. The home has been meticulously maintained with an efficient layout and no wasted space. The kitchen was fully updated with quartz countertops. The basement has also been updated, adding real living space, not just storage. Both bedrooms have California Closet built-ins. Outside, a 32x16 inground pool with a new gas heater anchors the backyard. A newly installed front patio adds another spot to sit outside. There's also a 2-car garage. Meticulously maintained, right down to the details, this is a rare find on Pittsfield's East Side

Step into a canvas of timeless character in this Historic Colonial, originally built and occupied by Nathaniel Austin,a surveyor who was instrumental in mapping and settling Berkshire County, situated in the town of Sheffield. This 5-bedroom, 2-bathroom residence offers a rare opportunity to restore a piece of Berkshire County history while imprinting your own vision on its enduring architecture. Location and Lifestyle* Tree-lined driveway, a short stroll to the village green, markets, dining, and outdoor recreation. Proximity to the Housatonic River, lakes, and scenic trails, inviting year-round strolling, hiking, and local exploration. Easy access to regional attractions, farms, and cultural events that define the area's heritage. Exterior and Structural Potential* Traditional Colonial silhouette with original exterior detail awaiting revival. clapboard siding offers excellent restoration potential. Generous lot space with room for landscaping, a garden, or outdoor living areas once

OPEN HOUSE Saturday May 2nd, 12:30 pm to 2 pm*Video tour and floor plans availableThis lovely colonial home features two separate units, as it has been designed to offer an in-law apartment. The property has been tastefully renovated with new kitchens with quartz countertops, gorgeous updated bathrooms, fresh interior and interior paint, refinished gleaming hardwood floors, and other improvements, that include new roof, updated electrical panels, among other updates!The first floor features an adorable enclosed porch, spacious bedroom, living room, eat-in kitchen and full bathroom, while the upstairs offers two bedrooms, full bathroom, kitchen and living room. This top floor could also be used as a 3-bedroom. Each unit has its separate electric panel, heat and hot water.Outside, a lovely yard and detached garage complete this great home. There is so much more to see, come fall in love with it!

Year round retreat in the Lake Buel Community. Thoughtfully designed spaces, cozy and unpretentious. The living area, comfortable for family and guests, has vaulted ceiling and Gas Fireplace, making this home just as inviting in the cooler months. Kitchen is functional, attractive and updated. Simple lines, wainscoting, wood floors, ductless A/C units. The Sunroom is perfect for Dining, board games or snuggling up with a book. Wonderful sunny deck, and a grassy lawn with fire pit. Upgrades include fenced yard and Generator! A shed to store your kayaks and bikes. Deeded Lake access. Minutes to Great Barrington town center, Butternut Ski Area and Hiking Trails. Easy access to Lake, just over the knoll

Charming New England home in the heart of West Stockbridge offering the perfect blend of small-town convenience and Berkshire living. Set on a generous lot with room to relax, garden, and entertain, this inviting property provides comfortable living spaces, abundant natural light, and the character that buyers seek in a Berkshire home.Enjoy the best of both worlds-peaceful surroundings while being just minutes from downtown West Stockbridge, Stockbridge, Great Barrington, local shops, restaurants, cultural attractions, and year-round outdoor recreation. This property offers exceptional value and opportunity.The spacious yard provides room for outdoor gatherings, pets, gardening, or simply enjoying the changing seasons. Inside, you'll find a warm and welcoming atmosphere ready to enjoy today while still offering opportunities to make it your own. This is an entry only listing. For all inquires call ()

Move right into this beautifully renovated 3-bedroom, 3-bath ranch on a picturesque 1-acre lot in the heart of Becket. Designed for comfortable one-level living with central A/C, the home offers a flexible floor plan with additional living space featuring its own private entrance, ideal for guests, a home office, hobbies, or whatever fits your lifestyle. Enjoy a full walkout basement, an expansive rear deck overlooking the private backyard, and the convenience of being just a short walk to the Becket Post Office and Town Hall. Minutes from Crystal Pond recreation (without HOA restrictions), Jacob's Pillow, Tanglewood, hiking, skiing, and everything the Berkshires have to offer

This beautifully positioned Berkshire retreat offers the perfect blend of privacy, comfort and natural beauty. Nestled on a peaceful country road, this inviting home is surrounded by scenic woodlands and mountain views while remaining conveniently close to the cultural attractions, outdoor recreation, and vibrant communities that make Berkshire County so desirable. Inside, you'll find warm and welcoming living spaces, ideal for both everyday living and entertaining. Enjoy a quiet morning coffee overlooking the views or simply unwinding after a day of hiking, skiing, or exploring the Berkshires, this property delivers the lifestyle buyers search for. An oversized heated workshop/garage with artist loft and half bath is simply magnificent for a multitude of occupations or hobbies. Incredible

Charming 2-Bedroom Home with Inviting Outdoor Spaces Welcome home to this inviting 2-bedroom, 1.5-bath property offering comfort, functionality, and great outdoor living space. Featuring a brand-new roof and a garage for added convenience, this home is move-in ready with plenty of potential. Inside, you'll find a welcoming layout along with a versatile bonus space perfect for a home office, guest room, playroom, or workout area. The spacious living areas flow nicely for everyday living and entertaining. Step outside to enjoy the cozy porch and a beautifully usable backyard area ideal for gatherings, or relaxing evenings with friends and family. Whether you're a first-time buyer, downsizing, or looking for a home with flexible space, this property checks all the boxes! Step outside to enjoy the private backyard retreat featuring a lovely stone sitting area, ideal for entertaining, grilling, or simply evenings outdoors. A one-car garage adds convenience and additional storage space. Whet

Mountain View Homer with Endless Potential Opportunity awaits at this 3-bedroom, 1-bath home nestled on a generous half-acre lot with breathtaking mountain views. If you're looking for a property with solid fundamentals and room to add your personal touch, this home is full of possibilities. Inside, you'll find a bright and welcoming living room filled with natural light, a functional galley-style kitchen, and three comfortably sized bedrooms. While the home could benefit from some updates and cosmetic improvements, it offers great bones and a strong foundation for renovation. Outside, the spacious half-acre property provides plenty of room for gardening, outdoor entertaining, expansion, or simply enjoying the peaceful surroundings and stunning mountain scenery. A detached garage adds valuable storage and workspace options. There is also an additional outbuilding that can be used for a multitude of different functions such as workshop or storage space. Whether you're a first-time buyer

Beautifully maintained 4-bedroom, 2.5-bath Colonial set on a quarter acre lot with privacy and curb appeal. Enjoy a spacious floor plan featurning a wood-burning fireplace, natural gas heat and hot water and newer replacement windows throughout, including new living room windows in 6/2026. The primary suite offers his-and-hers closets and a private bath. The finished lower level adds valuable living space with a family room, bar area, surround sound and separate storage room with built-in cabinets. Relax outdoors on the deck with a new awning (2026), framed by an arbor and private setting. Additional highlights include metered water, an attached 2-car garage with auto openers and rear storage room. Move-in ready and ideal for everyday living and entertaining!

A house that stops people mid-sentence! At the Lenox/Stockbridge line on the western shore of Lily Pond, discover this one-of-a-kind home. A rare architectural sanctuary where nature, privacy, and imagination quietly redefine Berkshire living. Embraced by woods and water, this 4br, 4ba contemporary is bathed in extraordinary light. Enter and you'll find over 5000 sf. living space. Bedrooms are spaced apart for maximum privacy; the open living area takes center stage for entertaining. Post-and-beam great-room/atrium w stone floor. Open kitchen w custom cherry cabinetry. First floor primary suite. Outside, enjoy over 4 acres of privacy: lawn, gardens and your own nature trails! Deeded rights to the White Pines beach on Stockbridge Bowl. Walking distance to Tanglewood! Must see!

Welcome to 1228 East St. A longtime family home filled with warmth, character and opportunity. Beautiful hardwood floors throughout much of the home. Updates include electric panel, blown in insulation, a new oil tank 2018 and new oil burner 2022. The spacious second floor kitchen area offers potential to create a two-family flat subject to city approval. A three-car garage offers extra space for storage, family vehicles or earning potential by renting out bays. Close to shopping, parks, recreation and everyday conveniences. This East st gem is full of possibilities. Schedule your showing today

Move-in ready and beautifully maintained, this charming 3-bedroom, 1-bath townhouse offers the perfect blend of classic character and modern updates. The spacious kitchen was completely renovated in 2024 and features granite countertops, new oak flooring, new appliances, and ample cabinet space. The bright and inviting living room is filled with natural light, while the formal dining room, also featuring new oak flooring, provides an ideal space for everyday meals or entertaining. Upstairs, you'll find three comfortable bedrooms and a full bath, all complemented by beautiful hardwood floors. The interior has been freshly painted throughout, giving the home a clean and welcoming feel. Additional features include high ceilings, natural gas heat and hot water, public water and sewer,a walk-up attic for additional storage, and a spacious basement offering ample storage space.Enjoy the best of the Berkshires from this ideally located home!

Escape to the Berkshires in this stunning Victorian gem - designed for those who appreciate space, style, and character. Whether you're planting roots in North Adams or seeking a weekend retreat. Fully renovated 5-bed, 2-bath home with 2,551 sq ft in the heart of North Adams. Slate roof, repainted front porch, chimney repairs, and updated plumbing and electrical throughout. Inside features refinished black India ink hardwood floors, new lighting fixtures, popcorn ceiling removal, washer/dryer hookups, and designer finishes including Revere Pewter and Gentlemen's Grey. Both bathrooms fully refreshed with new tile, fixtures, and flooring. Furniture included. Minutes from Mass MoCA and the Mohawk Trail. Proven short-term rental with 4 years of documented Airbnb performance

Steeped in the timeless elegance of historic Stockbridge, this exceptional Colonial captures the enduring charm of a bygone era, evoking the quintessential New England scenes made famous by Norman Rockwell. Beautifully sited just moments from the heart of town, this distinguished four-bedroom residence blends classic architectural details with gracious, comfortable living. Inside, three fireplaces anchor inviting gathering spaces filled with warmth and character, while three spacious ensuite bedrooms offer exceptional comfort and privacy. Rich period details, handsome proportions, and abundant natural light create a home that is both sophisticated and welcoming. Beyond the main residence, a separate guest cottage provides the perfect retreat for visitors, extended family, a home office, or creative studio. The expansive, level lawn presents a rare opportunity to create a private estate setting with ample room for a pool, tennis court, or beautifully landscaped gardens. Completing the p

Back on the market, and someone else's loss is about to be your gain. 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 the standout, wide open with new countertops and appliances that make it as functional as it is inviting. New flooring and an updated bath round out an interior that is completely move-in ready. Outside is where this property really sets itself apart. Connecting the house to the 2-car garage is an enclosed sunroom with windows overlooking the backyard, a bonus space that works year round, whether you're sipping coffee on a cold morning or keeping an eye on the backyard. The fenced backyard with a firepit gives you a great p

Open House Sunday August 2, from 2:30 to 4:00 This four bedroom two bath Log home has had many updated including the furnace, added garage and a Generac generator. The property will include an extra lot for possible expansion or just privacy. There are deeded lake rights. The currant owner brought the laundry up to the first floor. There are hook ups in the basement. The property includes lot 13 that the home is on and Lot 12 is a 75.03 X 215.41 extra lot

Welcome to 22 Wealthy Ave located in the desirable Yankee Orchards neighborhood. Fresh, bright, and move in ready, this thoughtfully renovated home features beautifully refinished hardwood floors, a main level bedroom and full bath, plus two additional bedrooms upstairs with cedar lined closets, built in dresser drawers, and a newly renovated full bath. The updated kitchen includes a farmhouse sink, dishwasher, refrigerator, and oven/range. An attached garage with a new epoxy floor offers direct access to both the home and basement, where laundry hookups are conveniently located. Close to shopping, parks, schools, and downtown Pittsfield

Set on a corner lot with a total of three lots totaling 0.61 acres, this 3-bedroom, 1-bath home offers plenty of outdoor space along with mountain views. The backyard features a covered porch overlooking the yard, giving you a great place to relax or enjoy the scenery. The main level includes a kitchen, dining area, and living room, while all three bedrooms and the full bathroom are located upstairs. There's also a walk-up attic, providing plenty of storage or additional space to use however you choose. With a large yard, extra land, and room to make it your own, this property offers a great opportunity for someone looking for space both inside and out

Cape-style 3-bedroom, 1-bath home in a coveted Southeast Pittsfield location directly across from Deming Park and close to coffee shops, restaurants, a pharmacy, convenience stores, and other Elm Street amenities. Features include newer windows, a newer roof, new carpeting upstairs, and a recently renovated bath. The interior offers an opportunity for additional cosmetic updates and personalization. Enjoy a private fenced backyard, oversized detached garage, two driveways for added off-street parking, and a seasonal room offering extra living space with potential for future year-round use, subject to approvals

Just up the road from the world-renowned Jacob's Pillow Dance Center, this stunning architect-designed sanctuary sits on 14 sprawling acres with panoramic views of Greenwater Pond and the rolling valley beyond. At the heart of this masterfully crafted 1998 home is the great room with soaring vaulted ceilings centered on a magnificent oversized stone fireplace. This spectacular space is banked by a wall of glass windows and doors leading to an impressive 60-foot deck for a front row seat to dazzling sunsets. The great room flows seamlessly into a sleek and thoughtfully appointed kitchen, and a spacious dining room perfect for entertaining a crowd. The primary suite serves as a personal haven, featuring its own stunning vistas, dual primary baths, and a small office. The lower level. The lower level enjoys more views and its own grand living room anchored by another stone fireplace, with access to a private concrete patio through expansive glass doors. Two well-appointed guest rooms and