779 houses for sale in Lenox, Lenox town Berkshire County Massachusetts

Classic two family brick colonial with many possibilities! Including a front/rear porch, two separate yards on each side, and off street parking. Enter each side into a wide, open hallway with the original hardwood floors throughout. The left side has four bedrooms and one bathroom with potential for a second bathroom off the kitchen. The right side has been split into two smaller units with separate kitchens and bathrooms but originally was a three bedroom apartment. Each unit has its own heating, hot water, and electrical systems

Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size of 4160 square feet provides a significant footprint within the urban landscape. We invite you to discover the potential and unique character of this Pittsfield address. Three Units are vacant and recently remodeled with market rents averaging about 1395.00 in the area. One Unit is rented month to month at 950.00

Welcome to this spacious 3-bedroom, 2-bath home offering 1,920 square feet of living space in Pittsfield's desirable Morningside neighborhood. This home blends classic character with several major updates already completed, including a newer roof (2025), replacement windows, oil tank (2024), boiler (2019), and sewer line (2019). The flexible floor plan provides plenty of room for everyday living, entertaining, or multi-generational needs. Enjoy an eat-in kitchen, full basement with interior and exterior access, a detached one-car garage, and a generous lot with mature landscaping. Conveniently located near parks, schools, restaurants, shopping, and downtown Pittsfield. Located in an RM-zoned district, this property may offer future multi-family or investment potential, subject to buyer due diligence. Property is being sold AS IS. A great opportunity for investors, cash buyers, or conventional financing buyers looking to add value while building equity through cosmetic improvements

Own Pittsfield History in this distinctive solidly built Georgian-style brick estate set proudly atop a hill in this coveted enclave of stately residences. Live on historic Crofut St. near the esteemed Pittsfield Country Club, Up Street Cultural Art District and ideally minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved by this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring Little Red Guest House with 3 bedrooms, 2 bath, first floor in-law suite and 2 car garage to host family, friends. Enjoy carefree ownership central to all that is Berkshire!

Step into effortless Berkshire living in this design-forward mid-century ranch. Perfectly positioned on a quiet downtown dead-end road, this 3-bedroom, 1-bathroom home seamlessly blends crisp, modern style with classic architectural character. Inside, original hardwood floors guide you through a bright, fluid one-level layout. The living room serves as a comfortable anchor for cozy mountain evenings, featuring a striking wood stove that pairs perfectly with the home's fresh, stylish aesthetic. Outside, the generous 0.41-acre level lot offers a private, shaded yard surrounded by mature trees-a fantastic feature for a property this close to the action. Beyond its residential charm, this property boasts coveted Business zoning, making it perfect for an ideal live-work lifestyle

Welcome to this charming four-bedroom, three-bath home nestled in a desirable Southeast Pittsfield neighborhood. Lovingly maintained and well insulated through the years, this home offers a warm and inviting atmosphere with a wonderful blend of original character and everyday comfort. Inside, you'll find hardwood flooring, spacious bedrooms, two first-floor bedrooms and 2 full bathroom, and an expansive addition at the rear of the home that provides flexible living space to suit your needs. The generous mudroom offers excellent functionality and storage, while updated windows help enhance efficiency and natural light throughout. The partially finished basement provides additional living or hobby space, along with ample storage opportunities. Outside, enjoy beautiful flowering gardens and mature landscaping that create a welcoming setting throughout the seasons. Filled with charm and ready for your own personal updates and touches, this well-cared-for home offers a wonderful opportunity

Neat as a pin cape walking distance to downtown Great Barrington and amenities, this home has been thoughtfully renovated top to bottom. This sweet property, also zoned commercially, has 4 bedrooms, a full bath, and even a partially finished basement. The kitchen, complete with a large pantry, retains the charming mid century details, while appealing to the modern aesthetic. Outside, there is a nice flat side yard, and views of the Housatonic river winding below. Clean and classic, all you have to do is move in and start making it your own!

Move right into the vacant unit and start generating income from the other. The property includes a small, easy-to-maintain yard, perfect for enjoying outdoor space without extensive upkeep. While there is no off-street parking, the property's functional layout and income-producing potential make it an excellent value. Whether you're looking to owner-occupy or expand your investment portfolio, this duplex is ready for its next owner

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,

Welcome to 34 Daniels Avenue, part of the Westside Legends Attainable Housing Program. This updated Pittsfield home offers a comfortable layout with recent improvements throughout, including new flooring, new appliances, and refreshed bathrooms. The interior feels clean, bright, and move-in ready, while still offering a practical and manageable footprint for everyday living. Conveniently located near downtown Pittsfield, local parks, restaurants, shopping, and cultural attractions, this home provides an excellent opportunity for qualified buyers seeking attainable homeownership in a central Berkshire location

One of the most exceptional homes to come to market, this remarkable property blends timeless elegance with resort-style living. Featuring 5 bedrooms, 3.5 baths, including private guest quarters with bath and secondary staircase, this home offers both sophistication and versatility. The luxurious primary bedroom suite is a true retreat, complete with a spacious en-suite bath designed for comfort and relaxation. A stunning new kitchen serves as the heart of the home, thoughtfully designed for both everyday living and refined entertaining. Impeccably curated interiors extend seamlessly to breathtaking outdoor spaces highlighted by a spectacular heated in-ground pool, extraordinary landscaping, and meticulously maintained grounds. A true masterpiece of design and luxury living. Join the Country Club of Pittsfield for golf, tennis and pickelball just 1.5 miles away. Downtown Pittsfield's restaurants, museum and theaters are a short 15 minute walk. Drive 15 minutes to downtown Lenox and Tan

Have you been searching for an affordable retreat in the Berkshires' OPTION # 2 = Cabin w/out the extra lots. Attention nature lovers, hikers and outdoor enthusiasts, this one is tucked within the Ashmere Lake community and may be just what you've been waiting for. Nestled among the trees on a private road, this 1-bedroom cottage offers a peaceful escape where mornings begin with birdsong and evenings end around the fire under the stars. The spacious living room features large windows that bring the outdoors in, while the oversized bedroom provides plenty of sleeping space for family and guests. Garage and Shed for extra storage. Bring your vision, your tools, and your love of the outdoors to restore this cabin into the getaway it was meant to be. EASY to show. Agents use ShowingTime

Exceptional Investment Opportunity: Versatility and Prime Location Discover 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

Investor Special! This gutted duplex offers a blank canvas with 6 bedrooms, 2 bathrooms, and 2,000 sqft of space, plus the possibility of additional living space in the attic. this property features a large backyard with a serene water stream, A standing garage remains on site for additional storage or future use. Situated on a 13,108 sqft lot, can also be bundled with 40 Pecks Rd and 48 Brown st (Pittsfield) for even greater investment potential. Endless possibilities await, renovate, rebuild, or reimagine this space to maximize returns! Schedule a showing today!

Situated on Great Barrington's highly sought after neighborhood of 'The Hill', 11 Prospect delivers on style, convenience and of course, location! This four bedroom home with two and a half baths over three floors and hardwood floors throughout, offers lots of room for family and friends. An oversized screened in porch, attached two car garage and a finished basement are just some of the 'must haves' to enjoy in this recently updated property. Steps away from the shoreline of Lake Mansfield and a simple stroll to downtown Great Barrington's many coffee shops, restaurants, bakeries and theaters, this property is the perfect move in ready home!

Introducing 39-41 Bartlett Avenue, a classic three-family Victorian in the heart of Pittsfield, offering a fantastic investment opportunity. This fully occupied property provides immediate income potential and features separate natural gas utilities for each unit. The home boasts vinyl siding and replacement windows, combining classic charm with practical updates. Ideally situated just moments from downtown. Whether you're looking to expand your portfolio or owner-occupy this well-located multi-family is one you won't want to miss

Conveniently located near shopping, dining, and the the Ashuwillticook Rail Trail for biking, walking, and outdoor recreation, this 3 bedroom, 2 bath modified Cape with first floor home office/den, offers comfort and opportunity. Featuring hardwood floors, a spacious deck, and a large backyard perfect for outdoor enjoyment. This well built home has great bones and is ready for its next chapter. The flexible floor plan provides ample living space, while the central location makes daily errands and recreation a breeze. A significant improvement is already underway, with the seller installing a brand-new sewer line prior to closing, providing added peace of mind for the next owner. Don't miss this chance to make this well-located home your own

A Rare Find: This lovely Victorian is waiting for a new family. Currently a two family but can be converted to a single family. Lovely Woodwork and it even has a pocket door. Close to restaurants and entertainment. Call today for a showing

Welcome to easy living at 691 Crane Ave, Pittsfield! This single-level ranch offers the perfect blend of convenience and peace of mind, highlighted by a 2-year-old roof and a two-car garage. Inside, you'll find a highly functional layout featuring fantastic space in the basement-an ideal setup for your favorite crafts, a home workshop, or weekend hobbies. Step out back to find a standout feature: a large, fully fenced-in yard that provides a wonderful private outdoor retreat. Nestled in a highly convenient location close to local shopping, dining, and schools, this move-in-ready home is designed for an effortless lifestyle. Don't miss this Berkshire gem!

Located on a quiet street in Housatonic, this charming cottage offers easy single-level living in a peaceful neighborhood setting. Set on a sunny double lot, the property provides extra outdoor space and flexibility with room to garden, entertain, play, or simply enjoy the surroundings. Inside, the home features an efficient layout filled with natural light, creating a bright and comfortable feeling. An oversized garage adds valuable storage and space for hobbies, tools, or workshop use. One of the highlights of this location is being within walking distance to Old Maids Park, where you can enjoy fishing, swimming, and a picnic area along the river. This sweet cottage offers a wonderful opportunity for those seeking a manageable home with everyday simplicity and nearby recreation. Minutes to downtown GB, and local amenities!

Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered clapboard. Inside, original period charm takes center stage with wide-plank wood floors and glowing fireplaces, perfectly paired with a rare, substantial footprint featuring 7 generous bedrooms and 6.5 bathrooms. Designed for effortless hosting, this expansive retreat offers an incredible canvas for a lucrative rental investment, a boutique bed-and-breakfast, or a magnificent private country compound

CONTEMPORARY FARMHOUSE! Sited on a knoll dotted with old apples trees overlooking scenic views all framed by a meandering fence. All you could ask for is in this well-built home, offering a first floor primary ensuite, library with fieldstone fireplace, A well appointed kitchen opens to both the dining and a living room with fireplace. A screen porch, 1/2 bath, laundry room/mudroom leading to a 2 car garage completes the first floor. The second floor offers 3 addition bedrooms, full bath, built-in bookcase with window seat. Kick back and relax on the front porch! A fabulous Berkshire house close to all Berkshire cultural venues, skiing, shopping, restaurants and, just plain fun!

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 backyard on a 6,969 sq ft lot. Efficient gas steam heat. Move-in ready and thoughtfully improved for comfortable everyday living

The mid-century retreat you've been waiting for. This classic home sits on over 4 private acres, delivering the ultimate Berkshire lifestyle with a bright, open floor plan and two cozy fireplaces. With 4 bedrooms, 3 baths, a large office, and a sun room looking overlooking your oasis, the layout offers perfect flexibility for guests or remote work. Outside, your private resort features a heated swimming pool and a dedicated tennis or pickle ball court tucked at the end of a quiet road for unmatched seclusion. Modern upgrades including a large solar array and a new heating system drastically reduce utility costs. Experience total privacy while staying minutes from everything that makes Great Barrington a premier Berkshire destination

Income producing 3-family home with almost 4,000 SF of living space, featuring two 3 bedrooms/1 bath apartments and one 3 bedroom/2 bath apartment, each one with its own laundry hookups. All 3 apartments have lead compliance certificate!There are vinyl replacement windows, newer heating systems, newer roof done in 2022, and separate natural gas heat and hot water and electricity for each unit.Hall Place is a dead end street and the property sits on a large corner lot, offering plenty of parking and good yard space.This is a great income producing property with rents totaling $74,472/year. All apartments are rented through Section 8. *Interior photos shown are from 2025 before tenants moving in