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

Prime investment opportunity! This five-unit property features a desirable mix of four, one-bedroom apartments and one, two-bedroom. All units have their own separate heating and electrical systems! Convenient location ensures high demand due to proximity to stores and the hospital. On-site parking. Detached garage/workshop could be rented separately for additional income or used as storage for tenants

This four bedroom two bath log home with deeded rights to Ashmere lake has several updates including the furnace, garage and Generac generator. Property includes an extra lot for possible expansion or just privacy. First floor laundry for ease and convenience, as well as 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

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!

Excellent investment or owner-occupied opportunity! This two-family flat offers two 2-bedroom, 1-bath apartments in a convenient Pittsfield location. Features include hardwood floors, a walk-up attic, public water and sewer, natural gas heat and hot water, two electric meters, one boiler, two hot water heaters, a spacious backyard, and ample off-street parking. The first-floor unit is owner-occupied, while the second-floor unit is vacant and in need of repairs, offering excellent value-add potential. Conveniently located near Berkshire Medical Center, downtown, schools, parks, shopping, restaurants, and cultural attractions. Property is being sold AS IS

Welcome home to this well-maintained 3-bedroom, 2.5-bath Cape offering 2,561 square feet of comfortable living space. The heart of the home is the kitchen and den area, featuring durable tile flooring and an open, inviting layout perfect for everyday living and entertaining. Sliding doors lead to a large screened porch overlooking the in-ground pool and beautifully sized backyard, creating an ideal setting for summer gatherings and outdoor relaxation. A formal living room with a cozy gas fireplace provides an elegant space for unwinding. The finished lower level offers additional flexible living space, perfect for home office, gym, or recreation area. Additional highlights include attached 2 car garage and ample storage. Enjoy indoor and outdoor living at its best in this attractive home

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

SUN DRENCHED MODERN HOME WITH POOL AND PRIVACY, A SHORT WALK TO THE WALDORF SCHOOL AND THE GREEN RIVER. This gorgeous property consists of 2 separate building lots and is on a lovely, quiet road ideal for walking and biking, and only 7 minutes drive to Guido's. The house, which has been recently completely reimagined and added onto, is an ode to sophistication, beauty, and practicality. 4+ bedrooms, 3.5 baths, Open plan sun filled kitchen/dining/living, walk in pantry, generous entry with built in benches and storage, TV room with custom shelving, bright office, and a loft like studio above the 3 car garage. For outdoor living, the mahogany deck runs along the back of the house and connects to a comfortable screened porch with plenty of room for dining and lounging

A diamond in the rough. Step into this 1900's colonial with 1400' sq ft on a large level corner lot. The first floor offer inviting kitchen; formal dining room; spacious living room, and covnient 1st floor laundry room. 2nd floor offers four bedrooms with closets in each room. The road frontage on 2 streets leads to endless possibilities for your outdoor activities. Walk up attic; full basement. House roof approx 15 yrs young Gas furnace approx 5 years young This house will not qualify for VA or FHA financing

Enjoy the relaxing Berkshire lifestyle on a friendly cul-de-sac within walking distance of town and Lake Mansfield. As the first house built on the street, the property has matured beautifully - seasonal flowering trees and pollinator-friendly gardens bring color and life to the yard from spring through fall. Cedar columns frame a distinctive front door that opens into 3,800 square feet of tastefully designed living space, where soaring ceilings, a linear gas fireplace, and built-in bookcases set the tone. The living room flows out to a screened-in porch with a treehouse-like view of the wooded backyard - the perfect spot for morning coffee or summer evenings. The chef's kitchen is beautifully appointed with Wolf and Sub-Zero appliances and granite countertops, and opens to the dining area and living room for easy entertaining. Also on the main floor: a primary suite with walk-in closet and spacious bath, two additional bedrooms (one with floor-to-ceiling built-in bookshelves), a full

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!

Welcome to 158-160 Linden Street in Pittsfield. This centrally located 2 family boast 3 bedrooms, 1 bath and laundry in each unit. The entire home was renovated approximately 25 years ago and has been well maintained since. Separate electric meters for each unit and they both offer electric baseboard heat that is not included in the rent. On the exterior you will find a large fenced in side yard, plenty of off street parking and a covered front porch. Don't miss the opportunity to own this great multifamily property!

Welcome to this impeccably maintained 4-BR, 2 bath residence offering comfort, style, and exceptional outdoor living. The updated kitchen features all new appliances, while the spacious layout provides plenty of room for family, guests, or a home office. Potential 1st floor BR! Step outside and discover your own private backyard retreat. Relax under the covered porch, entertain on the dining patio, or gather around the fire pit on cool evenings. Beautiful gardens add color and charm throughout the seasons, and the above-ground pool provides the perfect place to cool off and enjoy summer fun. Additional features include a one-car garage, well-maintained mechanicals, and pride of ownership evident throughout. Close to dining, shops, bus route and hospital! MOVE IN REA

PERFECT IN LENOX! This impeccably renovated Mid-Century Modern jewel has it all. Including a BIG VIEW! This 'down to the studs' interior rebuild including siding, windows, heating, electrical, plumbing, A/C with 2 zones and energy efficient LED lighting offers true main level living; three bedrooms, primary with walk in closet, open living/dining with stunning kitchen, main floor laundry, attached 2 car garage, sonos built in sound system and incredible natural light that envelops the panoramic view seen from every room; truly a move-in property. The location could not be more perfect. minutes to Miraval Resort for a little pampering, around the corner from beautiful Laurel Lake and of course minutes to the Village of Lenox and Tanglewood!

Charming open-concept Ranch includes a separate abutting building lot in the heart of the Berkshires on a quiet non-through street! This beautiful, move-in ready Ranch offers 1,959 sq ft of bright, inviting living space on the main level. Finished 1200 sq ft basement with a full bath adds extra space, perfect for a game room or holiday gatherings. The dining area connects to a large kitchen with newer quartz countertops. Great room features a natural gas fireplace. With 3 spacious bedrooms, 3 full bathrooms, there's plenty of room for everyone. Outside, enjoy a welcoming front porch with nice landscaping or host a barbecue on the large back deck. Complete with an attached 2-car garage. Close to Berkshire attractions, 15 minutes to Tanglewood, and minutes to shopping, this home truly has i

Calling all investors and hands-on owner-occupants! This 3-unit multi-family offers 15 rooms, 6 bedrooms, and 3 full baths across 3,510 sq ft on a 0.17-acre lot. The owner has already made key updates, including some new flooring, fresh paint, updated electric, and a new bulkhead, giving you a head start on renovations. Still needed: updated heating systems, roof work, wall patching, and final cosmetic finishes; a great candidate for a renovation loan (203k/HomeStyle) if you're looking to live in one unit while building equity. Investors can pick their own tenants and set market rents once complete. Public water/sewer and a full basement round out this diamond-in-the-rough opportunity to add to a portfolio or start one

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

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

Recently renovated colonial home with detached garage, located on a corner lot in a desirable Pittsfield location! This property features a lovely front porch as well as a side porch and great yard! There are 3 bedrooms, however, the home could be used as a 4-bedroom. You will love the two updated full bathrooms, one on each floor! Other improvements include a new roof, newer vinyl replacement windows and interior/exterior paint

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 diamond in the rough. Step into this 1900's colonial with 1400' sq ft on a large level corner lot. The first floor offer inviting kitchen; formal dining room; spacious living room, and covnient 1st floor laundry room. 2nd floor offers four bedrooms with closets in each room. The road frontage on 2 streets leads to endless possibilities for your outdoor activities. Walk up attic; full basement. House roof approx 15 yrs young Gas furnace approx 5 years young This house will not qualify for VA or FHA financing

Sun Filled Historic Reproduction Home Built in 2004 seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout-honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday living and entertaining. Step out to the inviting covered porch-an ideal spot to savor morning coffee and evening sunsets with mountain vistas. The primary suite captures stunning views, while the expansive yard provides additional room to roam. 2-car oversized garage. Secluded setting just minutes to downtown Gt Barrington and Berkshire attractions

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

This four bedroom two bath log home with deeded rights to Ashmere lake has several updates including the furnace, garage and Generac generator. Property includes an extra lot for possible expansion or just privacy. First floor laundry for ease and convenience, as well as 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 26 Crosier Ave-charming character meets creative opportunity! Nestled in the heart of Pittsfield, this delightful colonial-style home offers a bright, spacious layout with classic charm! With 3 bedrooms and 2 baths, cozy living room, a functional kitchen, and generously sized rooms filled with natural light. The unfinished third-level space whispers 'potential,' while the off-street parking and sunny porch add convenience and curb appeal. While this home has been lovingly maintained, it does need some cosmetic refresh-think fresh paint, updated fixtures, and modern touches to let its personality truly shine

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

In town 2-bedroom ranch with strong potential! Features include public water/sewer, off street parking, and a fenced backyard. Ideal for contractors, investors, or buyers seeking a project. Home is not insurable/does not qualify for standard financing due to roof condition and is offered as is. A great opportunity to renovate and add value

Beautifully updated while maintaining its classic New England charm. Offering 3 bedrooms, 1 full bath, and 1,335 square feet of move-in ready living space on a spacious and level half acre lot. The recently remodeled interior features a stunning new kitchen with white shaker cabinetry, granite countertops, subway tile backsplash, and new stainless steel appliances. The beautifully renovated bathroom showcases a custom tile shower surround, while fresh paint, updated flooring, recessed lighting, and hardwood floors throughout most of the home create a bright, inviting atmosphere. Large windows fill the living room with natural light, highlighting the home's warm character and comfortable layout. Step outside to enjoy the covered front porch or relax on the rear deck overlooking the generous backyard. The detached two-car garage provides excellent storage, workshop space, or protected parking. Conveniently located near the Ashuwillticook Rail Trail, Cheshire Reservoir, and Mount Greylock

Easy living Ranch home on beautiful Onota Lake. Fantastic views of the Lake and Distant Berkshire Hills. Enjoy westerly sunset views from your expansive, manicured lawn and almost every room in the house. A quiet setting with comparable homes and easy access to all the Berkshires has to offer. Needs a little TLC, but well worth it for this sought after location and lifestyle. Hardwood floors refinished and interior recently painted

Easy living Ranch home on beautiful Onota Lake. Fantastic views of the Lake and Distant Berkshire Hills. Enjoy westerly sunset views from your expansive, manicured lawn and almost every room in the house. A quiet setting with comparable homes and easy access to all the Berkshires has to offer. Needs a little TLC, but well worth it for this sought after location and lifestyle. Hardwood floors refinished and interior recently painted

Welcome home to this charming ranch offering effortless single-level living in a quiet, private, yet convenient neighborhood! Lovingly built, maintained, and cherished by the same family for decades, this home offers the perfect blend of comfort, flexibility, and functionality. The living room has a beautiful bay window, 3 bedrooms with abundant closet space and a full bath. The kitchen opens to the dining area, where a French door leads to a spacious deck overlooking the beautifully landscaped, fenced backyard. The finished lower level expands your living space with a 2nd bath, laundry area, storage, and a flexible area perfect for entertaining, a home gym or additional guest space. Move right in and discover why this hidden gem is the perfect place to call home!