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

Discover the exceptional lakefront lifestyle in this beautifully renovated, move-in ready 2-bedroom, 2-bath residence on Onota Lake. Bathed in natural light, expansive walls of windows frame captivating water views from the living room, dining area, and kitchen, creating a seamless connection to the outdoors. A welcoming fireplace adds warmth and charm, while efficient mini-split systems provide year-round comfort. The spacious primary suite offers a private bath and a serene retreat. Outdoors, a lakeside deck, fire pit and private dock create an inviting setting for entertaining, boating, and relaxed Berkshire living. A truly special waterfront offering

STILL HOUSE brings a new level of contemporary design to the Berkshires-quietly luxurious, exquisitely detailed, and made to be lived in. Minutes from the center of Great Barrington, this newly completed 5,148-square-foot home pairs the distinctive vision of acclaimed Brooklyn studio Me and General Design with exceptional craftsmanship and materials throughout. Four bedrooms, five-and-a-half baths, a heated saltwater pool, bespoke spa and fitness spaces, solar energy and exceptional privacy make this as much a retreat as a home.Preserved stone walls from the original structure bring history, texture and a distinctly Berkshire character to the new architecture. The main living level opens into a dramatic kitchen, dining and living space with cathedral ceilings, two stories of glass and views into the surrounding landscape. The custom Porcelanosa kitchen features richly veined stone, a substantial island, induction cooking, double ovens, integrated refrigeration, microwave drawer, dedica

Well-updated split-level ranch offering plenty of space inside and out! Updated kitchen features granite countertops, newer cabinetry, tile flooring and stainless appliances. Hardwood floors flow through much of the main level. The primary bedroom offers a slider to the elevated 10x42 wood deck overlooking the fenced backyard. Main-level full bath features a double vanity and tiled tub/shower. Two finished lower-level rooms plus a full bath add approx. 414 sq. ft. of finished living space, included in GLA. Enjoy the expansive deck and fenced yard, plus a large detached two-car garage with plenty of room for vehicles, storage, hobbies or a workshop. A well-maintained home with versatile living space and great outdoor features!

Step into timeless elegance in this exceptional 6-bedroom, 3-bath historic residence, where classic architectural details blend seamlessly with thoughtful modern updates. Meticulously maintained and enhanced over the years, this one-of-a-kind home showcases the craftsmanship and character rarely found today. From the moment you enter, you'll be captivated by the grand, sun-filled rooms, gleaming hardwood floors, original built-ins, statement fireplaces, and exquisite stained glass windows that fill the home with natural light. With updated electrical, plumbing, boiler, sewer line and kitchen, this home is designed for everyday living and entertaining. Ideally located near downtown Pittsfield's cultural attractions this is a rare opportunity to own a piece of architectural history

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

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio above the den-offering an ideal, quiet space for an executive home office or fitness room. Outdoor living is built for relaxation, featuring an expansive wrap-around deck with scenic views, a stone patio,

Offered for the first time by its original owner, this is a rare opportunity to own an exceptional Pontoosuc Lake property and make it entirely your own. With 115 feet of direct water frontage, the property offers a generous setting to enjoy life on the lake. Designed for gathering and entertaining, this spacious lakefront home features a fireplaced living area, original walnut woodwork, stone countertop kitchen, first-floor primary suite, generously sized upstairs bedrooms, large second-floor bath, and covered porch overlooking the water. Wake up to incredible sunrises over the hills reflecting across the water. Spend your days swimming and boating right from your shoreline, head out onto the open lake to take in views of Mount Greylock, and cruise the water for the evening sunse Bring your own vision and make this home completely yours. You have the freedom to preserve the classic character you love while updating the rest to match your personal style. The setting and footprint also

Get ready to relax in the Berkshires in your new condo with big windows, high ceilings, plus brand new boiler and A/C! Owner retiring and moving down south, giving up his beloved in town Great Barrington location. You'll love being close to stores and provisions for your various adventures, while being close to all the attractions that the Berkshires have to offer. And, at an approximately two and 1/2 hours from Boston or NYC, your location can't be beat. Come experience worry free living while the condo cuts your grass in the summer, or plows your driveway while you're up here to ski. 9 Stanley is simply country living at it's best! It's all here for you to see!

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

Welcome home to this spacious raised ranch located in a highly desirable neighborhood! This well-maintained property offers five bedrooms and two full baths, providing plenty of room for family, guests, or a home office. The inviting family room is perfect for gathering and entertaining, while the two-car garage adds convenience and storage. Step outside and enjoy the oversized deck overlooking the beautiful built-in pool an ideal setting for summer fun, outdoor dining, and relaxing with friends and family. With generous living space, great amenities, and a sought-after location close to schools, shopping, and local attractions, this home is a wonderful opportunity you wont want to miss

Charming 2-family flat offering a great opportunity for owner-occupants or investors alike! This well-maintained property features beautiful wood floors, inviting front porches, and private back decks perfect for relaxing or entertaining. Both units have separate utilities for added convenience and efficiency. The second-floor apartment includes a finished attic area providing extra living space. Outside, enjoy a nice yard with plenty of space for outdoor activities, along with a detached garage for parking and storage. A versatile multi-family property with character, space, and income potential!

Move in ready! New roof and gutters in 2026, maintains original details but has been thoroughly updated. Located on a quiet, tree lined street, 81 Northumberland offers the kind of lifestyle one dreams about. Imagine walking your children to the nearby elementary school, stopping in for fresh pastries at the local bakery, grabbing a coffee on the way home, or enjoying an evening stroll through the established Southeast neighborhood. With a warm, inviting home and everyday conveniences just minutes away, this is more than a place to live - it's a place to build lasting memories. During the cooler seasons the woodburning fireplace offers warmth and ambiance to your home. Within walking distance to stores, shopping and restaurants. A short drive and you can enjoy Canoe Meadows, Tanglewood, Bousquet and Jiminy Peak Ski Mountains and all the treasures of Berkshires

Spacious single-level living in Woodmont Estates! Set on 3.04 acres across two lots, this 3,400 sq. ft. home offers 4 bedrooms, 2.5 baths, an updated kitchen, renovated primary bath, custom library, private office, four-season sunroom with newer Andersen windows, and a large bonus room with endless possibilities. Recent improvements include a repaired retaining wall and tree removal that opened up the front entry, bringing in more natural light and enhancing curb appeal. Enjoy mature landscaping, seasonal water views, a brook, sunrise views, protected land beyond, central air, natural gas heat, and a full walkout lower level with abundant storage and future potential

This charming Ranch-style home offers the perfect blend of comfort, privacy, and convenience in a desirable Cheshire neighborhood, just a short distance from scenic Cheshire Lake and the Ashuwillticook Rail Trail.Inside, you'll find a spacious and inviting layout featuring three bedrooms, one full bathroom, beautiful oak hardwood flooring, and a generous living room filled with natural light. The renovated eat-in kitchen is ideal for everyday living and entertaining, featuring granite countertops and newer appliances. Central air provides year-round comfort, while the spacious basement offers excellent storage and flexibility.Step outside to enjoy the beautiful backyard-perfect for summer gatherings, gardening, relaxing, or simply enjoying the peaceful surroundings

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio above the den-offering an ideal, quiet space for an executive home office or fitness room. Outdoor living is built for relaxation, featuring an expansive wrap-around deck with scenic views, a stone patio,

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

Opportunity awaits! A mature apple tree greets you at the entrance, setting the tone for this spacious older home full of untapped potential. The property offers generous living space with room to reimagine the layout to suit your vision. Set on an approximate quarter acre lot, the yard provides plenty of room to garden, expand, or simply enjoy some outdoor space of your own. This home requires significant renovation from top to bottom, making it a strong fit for investors, contractors, or hands on buyers ready to restore character and build real equity. With good bones and a solid footprint, this is a rare chance to create something special in a convenient Pittsfield location. Bring your tools, your vision, and your work boots. This one is ready for a comeback

Set in a desirable southeast Pittsfield neighborhood, this charming 3 bedroom, 1 bath Colonial offers a compelling blend of timeless character, natural light, and thoughtfully addressed updates. Original hardwood floors lend warmth and authenticity throughout the living spaces, while updated windows bring added brightness to the home. The updated kitchen, with granite countertops, provides a comfortable foundation for everyday living and entertaining, while a fully heated sunroom adds an especially appealing dimension to the home; an inviting year-round retreat for morning coffee, reading, or simply enjoying the changing seasons. Important improvements, including updated electrical, have already been completed, offering peace of mind while leaving room for the next owner to bring their own vision and personal style. Ideally located in southeast Pittsfield, this welcoming Colonial presents an opportunity to enjoy the character of a classic New England home with many of the essential upd

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

Ideally located in the Downtown Arts District just off South Street, this two-family property offers an excellent investment opportunity. Fully renovated in 2007, the property features a total of 6 bedrooms and 2 1/2 bathrooms, with separate utilities for each apartment, paid by the respective tenants.The first-floor apartment offers 3 bedrooms, 1 1/2 bathrooms, and numerous updates throughout. The second-floor apartment features 3 bedrooms and 1 full bathroom, providing comfortable and functional living space.The property is serviced by public water and sewer and is equipped with two electric meters, two boilers, and two hot water heaters. Both apartments are heated with natural gas, with natural gas hot water as well. Conveniently located near Berkshire Medical Center, Berkshire Museum, The Colonial Theatre, Barrington Stage, schools, restaurants, shopping, and downtown attractions. Zoned business and residential, this property offers excellent investment potential in a convenient do

First time ever to Market! Charming Cape-style home on outer Churchill, directly abutting the Pittsfield State Forest with Onota lake nearby. This 3 bed, 1 bath property offers 1,529 square feet of living space and has been in the same family for decades, most recently operating as a successful Airbnb. The main level features mix of hardwood floors and luxury vinyl plank, 2 bedrooms, a full bath, and an updated kitchen with beautiful wood cabinets, granite countertops and stainless steel appliances. A cozy, heated back porch/family room with propane stove provides year-round comfort. Upstairs features a large bedroom and open bonus space. Most recent updates include vinyl replacement windows, sheetrock and insulation, an updated well water filtration system, and newer carpeting. Enjoy peace, privacy, and endless outdoor recreation right outside your door with this versatile Berkshire retreat

Welcome home to this beautifully updated 3-bedroom, 1-bath home in a great neighborhood close to the local school! The first-floor bedroom and bathroom offer convenient one-level living, while the recently renovated kitchen with marble backsplash, quartz counter tops and shaker cabinets provide a fresh, modern feel. Numerous updates throughout make this home move-in ready. Enjoy the spacious backyard, perfect for relaxing, entertaining, gardening or play. The partially finished basement offers additional flexible space, with room for a home office, playroom, or gym on one side and plenty of storage on the other. With its convenient location, thoughtful updates, and inviting yard, this home is a wonderful opportunity!

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

Charming Cape-style home offering comfort, character, and a convenient location! This tastefully decorated three-bedroom, one-bath home features inviting living spaces and a layout that is both functional and easy to enjoy. A one-car garage provides added convenience, while the private backyard creates a peaceful retreat for relaxing or entertaining. Step outside to the deck and patio area-an ideal setting for morning coffee, summer gatherings, or simply enjoying your own outdoor space. The partially finished basement adds valuable additional living and entertaining space, complete with a bar and comfortable seating area-perfect for game nights, casual gatherings, or relaxing with friends and family. Solar panels provide an added energy-efficient feature, helping to make this charming

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

Discover a prime investment opportunity at 110-118 Lincoln Street in Pittsfield! This well-maintained property features four spacious units, each offering three bedrooms and one bath-perfect for attracting reliable tenants. With separate utilities for each unit, managing expenses is seamless. Ample off-street parking ensures convenience for all residents, enhancing the living experience. Ideal for investors or those looking to enter the rental market, this property will be delivered vacant at closing, allowing for immediate occupancy or renovations. Don't miss out on this fantastic chance to secure this valuable asset

Welcome to 186 Burbank Street! This charming colonial-style home offers two bedrooms, one full bathroom, and 1,158 square feet of living space. Situated on a level corner lot in an established residential neighborhood, the home features a functional layout with plenty of potential. The main level includes a spacious kitchen with ample cabinet and counter space, a formal dining room, comfortable living room, and full bathroom. Upstairs, you'll find both bedrooms. A full basement provides plenty of additional storage, while the attached garage and private driveway offer convenient off-street parking. Conveniently located near Silver Lake, Lakewood Park, shopping, dining, and other local amenities. Bring your ideas and make this Pittsfield home your own! This property is eligible under Freddie Mac First Look Initiative through 09/06/2026. Only owner occupant, non-profit and Neighborhood Stabilization Program (NSP) offers will be reviewed and considered

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!

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!

Beautifully updated and maintained four bedroom, three and a half bath colonial. Spacious common areas washed with natural light make this home special. The main level boasts a large eat in kitchen, dining room, expansive living room with wood floors, family room with built ins and fireplace, separate laundry room, half bath, two car oversized garage and beautiful screened porch overlooking the landscaped large yard. The second level has three guest bedrooms, full bath and large primary bedroom with en suite and double closets. The finished lower level offers a media/flex room, office, bathroom and storage. This Convenient location is on the Southeast side of Pittsfield near Lenox and under 15 minutes to Tangelwood! This Convenient location is on the Southeast side of Pittsfield's best school districts near Lenox and under 15 minutes to Tangelwood!