1,259 houses for sale in Lenox town, Berkshire County Massachusetts

Iconic Lenox home: very rarely does a home with this historic integrity come on the market. now is your time to continue its legacy. Built in 1915 as one of the focal points of Cliffwood Street, this charming home has been updated for today's life style without sacrificing its significant architectural details. Beautiful common rooms including a dream kitchen with marble counters, formal Dining Room with French doors to the enclosed porch and onto the new deck and acre of land; formal Living Room with fireplace, family room and welcoming foyer off the front porch. The 2nd floor is home to all 5 bedrooms plus an inviting 'summer porch' off one! Updated baths, kitchen, roof, utilities. and add to that: crown moldings, pocket doors. this home is truly a rare find in today's market More Details of 19 Cliffwood St.: This iconic Lenox home is situated on a full private acre of land, only a few steps from the Village and is a rare find: Throughout the down stairs, 10' ceilings and plentiful l

Elegance Meets History on 1 Eaton Lane! Tucked away on a quiet, sought-after street just minutes from the Country Club of Pittsfield and only 10 minutes to vibrant downtown Lenox, this remarkable Colonial seamlessly blends timeless character with extraordinary versatility. Offering just under 5,000 square feet of living space, this historic estate presents a rare opportunity for those seeking a home with a story. The main house is a masterclass in classic architecture, featuring period details enhanced by thoughtful modern updates. High ceilings, gleaming hardwood floors, and charming front and back staircases ground the home in history, while the spacious layout provides endless room to breathe. The heart of the home is a sophisticated kitchen, featuring rich cherry cabinetry, new SS appliance brand-new quartz countertops, and a dedicated coffee bar. The living room is a large inviting retreat, anchored by a wood burning fireplace and striking exposed joist-and-beam ceilings. The dini

Perfectly situated in a highly sought-after community just moments from the scenic waters of Pontoosuc Lake, and conveniently located near the main corridor connecting Williamstown and South County, this beautifully maintained, approximately 11-year-old standalone condo offers the ultimate rarity: the privacy of a single-family home with the effortless lifestyle of condo living. Inside, gleaming wood floors and abundant natural light flow through a thoughtfully designed layout. A welcoming living and dining area leads to a stunning chef's kitchen at the heart of the home. Just beyond, a cozy family room opens to a beautiful screened back porch, the perfect spot to bask in the afternoon sun after a morning by the lake. Tucked away on the opposite side of the home, the serene primary suite features a walk-in closet and an airy en suite bath with a sleek, custom-tiled glass shower. Two additional bright bedrooms share a full bath, while convenient first-floor laundry completes this ideal

Well-located home nestled in a desirable neighborhood with convenient access to local amenities, schools, and outdoor recreation. This inviting property offers a comfortable layout designed for everyday living and entertaining, featuring bright, sun-filled spaces and a warm, welcoming atmosphere throughout. The home provides a functional flow with generously sized living areas, a thoughtfully designed kitchen, and ample room to accommodate a variety of lifestyles. Bedrooms offer comfortable retreats, while additional space allows for a home office, guest area, or flex use to suit your needs. Enjoy the benefits of a private yard and deck, ideal for relaxing, gardening, or hosting gatherings. Whether you are a first-time buyer, downsizing, or looking for a Ber

Mixed-use property in vibrant Housatonic village center. Three flexible units: two residential apartments above commercial space. Prime location within walking distance to local shops, art galleries, restaurants, town library, and neighborhood park with playground. Stunning views of the iconic Housatonic water tower and historic mill town industrial architecture. Property features mature gardens, private walled patio area, three dedicated parking spaces, plus rear garage requiring renovation work. Perfect investment opportunity for entrepreneurs seeking rental income or business owners wanting live-work space. The building offers excellent potential in this growing creative community hub with strong local character and charm. A must see!

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

Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest. The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors. A heated sunroom and screened porch extend the living experience across seasons. The primary suite includes an en-suite bath, and this level is further enhanced by a second kitchen and laundry hookups, creating true independence within the home. The secon

Nestled on 7.79 private mountaintop acres, this distinguished 1916 Italianate Berkshire Cottage sparkles with original architectural details, beautiful fireplaces throughout, and a stunning reflection pool surrounded by mature gardens. Four spacious bedrooms include a luxurious primary suite with sitting room, while the grand great hall creates perfect spaces for both intimate gatherings and gracious entertaining. The lower level features an elegant one-bedroom guest apartment plus a separate catering kitchen, utility rooms and two one car garages, while the main house enjoys lovely terraces facing south, east and west. Surrounded by 200 protected acres near world-class Tanglewood - your own slice of paradise where old-world charm meets mountain-top serenity! In 1916, renowned patron of the arts Elizabeth Sprague Coolidge commissioned this magnificent 4-bedroom mountain house atop South Mountain in Pittsfield as a gift for her son Albert. This stunning stucco Italianate Berkshire cotta

Building has been used as an antique business for the last 50 years. Seller had previously lived in the upstairs apartment. Located across the street from Mend and Calgary's and.5 miles from downtown Great Barrington. Selling as is, business and inventory separately - negotiable with owner

Nestled within a mixed use residential/commercial block this renovated space is ready for the next creative commercial endeavor. Rent the house and use the studio for art, office, store or Live and work all within walking distance to town center. Thoughtfully brought from a commercial office space to a 2 bedroom, 1.5 bath, bright open and airy living space with 5 parking spots and a nice size yard

Set on two-thirds of an acre in a residential area, walkable to all Great Barrington has to offer, this versatile home offers 4+ bedrooms and 3 bathrooms. The main floor boasts two bedrooms, a dedicated office or guest space, one and a half baths, laundry, as well as the main living, dining, and kitchen areas. Upstairs you will find 2 additional bedrooms and another half bath. Wood-burning fireplace, exposed beams, hardwood floors, and a spacious three-season porch overlooking the stone patio all make this property a must-see. The lot offers a large yard as well as the patio, a two car garage and an additional outbuilding

A rare French Manor estate gracing one of South Berkshire's most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary is awaiting buyers final finishes and offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook-creating a secluded retreat that feels worlds away, yet remains moments from the cultural heart of the Berkshires. SEE LIST OF ITEMS TO BE FINISHED IN DOCUMENTS. At the center of the estate stands a newly built main residence inspired by the grand proportions of the Gilded Age, featuring soaring 19-foot ceilings and impeccable architectural presence. Thoughtfully constructed by a highly regarded local craftsman, the home showcases state-of-the-art mechanical systems, including geothermal heating and cooling, blending classic elegance with modern efficiency. Approaching completion, the residence presents

Elegance Meets History on 1 Eaton Lane! Tucked away on a quiet, sought-after street just minutes from the Country Club of Pittsfield and only 10 minutes to vibrant downtown Lenox, this remarkable Colonial seamlessly blends timeless character with extraordinary versatility. Offering just under 5,000 square feet of living space, this historic estate presents a rare opportunity for those seeking a home with a story. The main house is a masterclass in classic architecture, featuring period details enhanced by thoughtful modern updates. High ceilings, gleaming hardwood floors, and charming front and back staircases ground the home in history, while the spacious layout provides endless room to breathe. The heart of the home is a sophisticated kitchen, featuring rich cherry cabinetry, new SS appliance brand-new quartz countertops, and a dedicated coffee bar. The living room is a large inviting retreat, anchored by a wood burning fireplace and striking exposed joist-and-beam ceilings. The dini

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

Lovingly maintained, this charming 2-bedroom Cape is ready for its next chapter. Filled with warmth and timeless appeal, a cozy wood-burning fireplace perfect for New England evenings, and a comfortable layout that's easy to make your own. Step outside to a sweet backyard complete with a beautiful deck, an ideal spot for morning coffee, summer barbecues, or simply relaxing outdoors. Conveniently located in Pittsfield, you'll enjoy being just a short drive from Onota Lake Beach and Boat Launch, offering easy access to swimming, boating, fishing, and some of the Berkshires' favorite outdoor recreation. You won't want to miss this delightful home for your new beginnings!

Welcome home to this charming 3-bedroom, 1-bath property nestled on a spacious corner lot in a wonderful neighborhood. Located on a quiet no-outlet street, this home offers the perfect blend of privacy, comfort, and convenience. Inside, you'll find an upgraded kitchen featuring newer appliances, ideal for everyday living and entertaining. The inviting living space is highlighted by a cozy wood-burning fireplace, while the bright sun porch provides the perfect place to relax with your morning coffee or unwind at the end of the day. French doors open to a deck overlooking the large, level backyard, offering plenty of room for outdoor gatherings, gardening, or simply enjoying the extra elbow room. One of the standout features is the impressive 24' x 28' detached garage with a concrete floor and high ceilings-perfect for vehicles, a workshop, hobbies, or additional storage. With its charming character, thoughtful updates, generous lot, and peaceful setting, this home is a rare opportunity

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

Set within one of the Berkshires most coveted communities, 9 Eastbrook Lane is a masterclass in refined living, where thoughtful design meets impeccable care. Beautifully and intentionally sited, this distinguished residence offers 5 bedrooms, 3 full and 2 half baths across a gracious, light-filled layout designed for both elegant entertaining and everyday comfort. The stunning kitchen showcases rich maple cabinetry, a premium Viking range, dual refrigerators and exceptional workspace, perfectly suited for the discerning cook. The renovated primary bathroom evokes a true spa experience, blending luxury and serenity with timeless finishes. Every detail has been meticulously maintained, from the seamless indoor-outdoor flow to the expansive Trex decking ideal for al fresco gatherings. Lower level includes a finished area for home gym as well as a finished laundry room, large mechanical/storage area, and a workshop/storage area. This square footage is not included in the 3,823 square feet

Lovely single level condo on the Hill. Just a short walk to town, The Oakwood provides a quiet community with a lovely pool, garaged parking, and mature landscaping. 2 bedrooms, 2 baths, a cozy living room with a wood burning fireplace and sliders to a sunny deck. Freshly painted, neat as a pin, and ready to move into

This 4-bedroom, 1 1/2-bath home offers over 1,800 square feet of comfortable living space on a spacious 0.58-acre lot. This home features hardwood floors throughout the main living areas and bedrooms, with durable flooring in the kitchen and bathrooms with a spacious addition room. This home has an unfinished basement with a finished bonus room. Improvements over the years include: 2018: High-efficiency propane boiler 2019: New composite deck 2019: Attic air sealing and additional insulation for improved energy efficiency 2020: Bonus room addition 2022: New garage floor 2024: Completely renovated full bathroom Additional features include: Public water and private septic Cast iron baseboard heat throughout Low property taxes Attached one-car garage

Investment Opportunity with Owner-Occupant Potential! This well-maintained two-family home offers spacious 3-4 bedroom apartments in each unit, making it an excellent opportunity for investors or buyers looking to offset their mortgage with rental income. One unit is currently vacant, allowing for immediate occupancy or the ability to secure a new tenant at current market rents. The occupied unit features separate utilities, all paid by the tenant, helping to maximize your return. The property offers low-maintenance vinyl siding, most replacement windows, and a convenient location close to schools, parks, shopping, and everyday amenities. Whether you're expanding your investment portfolio or searching for a home with built-in income potential, this versatile property is one you won't want to miss

Completely renovated New England farmhouse offering the perfect blend of historic charm and modern convenience. Thoughtfully remodeled throughout with updated kitchen, baths, systems, and finishes while preserving the character and warmth of a classic Berkshire home. Bright, inviting living spaces, abundant natural light, and quality craftsmanship create a move-in-ready residence with potentially two primary suites, one up and one down. Conveniently located near Gt Barrington's shops, restaurants, Berkshire County cultural attractions and ski/outdoor recreation. A rare opportunity to enjoy modern living in a beautifully restored farmhouse with lush private setting and fenced yard. A garden level pergola with seating area invites conversation with family and friends in complete privacy

A rare French Manor estate gracing one of South Berkshire's most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary is awaiting buyers final finishes and offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook-creating a secluded retreat that feels worlds away, yet remains moments from the cultural heart of the Berkshires. SEE LIST OF ITEMS TO BE FINISHED IN DOCUMENTS. At the center of the estate stands a newly built main residence inspired by the grand proportions of the Gilded Age, featuring soaring 19-foot ceilings and impeccable architectural presence. Thoughtfully constructed by a highly regarded local craftsman, the home showcases state-of-the-art mechanical systems, including geothermal heating and cooling, blending classic elegance with modern efficiency. Approaching completion, the residence presents

Welcome to life on beautiful Pontoosuc Lake, where breathtaking sunrise views and year-round waterfront living await. This charming, move-in-ready home offers the perfect combination of comfort, thoughtful updates, and low-maintenance living in a truly special lakefront setting. The open and airy living room features soaring vaulted ceilings, expansive windows that capture stunning lake views, abundant natural light, and a cozy gas fireplace, creating a warm and inviting space to relax or entertain. The well-designed floor plan includes spacious first-floor bedrooms with generous walk-in closets, updated bathrooms, newer flooring, Anderson windows, skylights, and multiple heating zones for added comfort. Designed with convenience in mind, the home offers natural gas heat, owned solar panels, energy-efficient air conditioning units, low-maintenance vinyl siding, and a two-car garage. The finished lower level provides additional living space and a versatile bonus room with direct access

Located in a 'hidden' neighborhood behind a stonewall entrance, this newly built home offers tranquil living just 5 minutes from the heart of Great Barrington. The spacious farmhouse front porch is the perfect spot to enjoy quiet mornings or gather in evenings with family and friends. Light-filled and open, the main level features an elegant living and dining area framed by French doors, a gas fireplace, and a chef's kitchen designed for effortless entertaining. Also on the 1st floor, a guest bedroom suite enjoys a private bath with shower and soaking tub. On the 2nd floor the generous primary suite offers dual walk-in closets as well as an luxuriously oversized shower and soaking tub. Also on this level is a guest bedroom with ensuite bath plus two additional bedrooms with a shared bath and laundry. The lower level features approximately 1100 sf of finished space, brightened by a bank of sliding doors. These two rooms would be perfect for a family room, home office, or fitness space.

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure. Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury. MORE The main level of the home includes a generous living room, a formal dining room featuring a custom four-wall mural by noted (formerly local) artist Laurel Tewes, a cozy library or den, a well-appointed kitchen with three refrigeration units including a side-by-si

Home on over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous counter space leading to the bright living room. Another feature on the first floor is that there is an option for private living quarters/in-law suite with its own entrance. The large primary suite offers a cozy fireplace, two walk-in closets, and an en suite bath with shower and jetted tub. Additionally, there is a first-floor laundry off the two-car garage, and an extra room great for an office. Needs TLC

Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, and the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area features a cozy gas fireplace, creating a warm focal point for chilly evenings, while the kitchen comes equipped with sleek, modern appliances. This turnkey residence offers 3 spacious bedrooms plus a versatile 4th full-size room that's ideal for a fourth bedroom, dedicated home office, or quiet retreat-along with 2.5 updated bathrooms. Downstairs, a vast, full open basement provides endless possibilities for exceptional storage, a home gym, or a recreation room. Beyond the interior, your ultimate outdoor sanctuary awaits in a professionally landscaped, fully fenced-in yard lined with a lush he

Thoughtfully maintained and move-in ready, this 2013 raised ranch is privately set on over 9 beautiful acres in Becket, offering the perfect blend of comfort, space, and Berkshire tranquility. This 3-bedroom, 2-full-bath home features a bright, open-concept floor plan with sun filled living, dining, and kitchen areas designed for both everyday living and effortless entertaining. Large windows fill the home with natural light, while the spacious newly renovated deck invites you to relax, dine outdoors, and enjoy the peaceful wooded setting. The finished lower level provides flexible bonus space ideal for a family room, home office, fitness area, or playroom. There is space for a bathroom already plumbed. An attached two-car garage offers convenience and additional storage. Surrounded by nature yet just minutes from the quaint village of Becket, this property is perfectly situated for those who love the outdoors. Enjoy easy access to hiking trails, lakes, and year-round recreational oppo

37-acre, ROCK RIDGE FARM, with early mid 20th century roots. Built in 1785, steeped in local history, Property has remained a working and residential farmstead today and reflects the regions long tradition of working farms. Offering a blend of local heritage and timeless New England character. Along with the main house there are several outbuildings that could be renovated, repurposed or redesigned to your vision. Original house boasts multiple living quarters. Continue this as a working farm, wedding venue, country inn or primary residence. Frontage on Dublin Rd and State Rd. Close to Tanglewood, Bousquet Ski-Sport and other cultural attractions. Easy access to routes in and out of the Berkshires. 37 acres that offer a rare freedom to build, invest or preserve something truly lasting