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

Welcome to this charming, updated ranch tucked into a quiet neighborhood and conveniently located near shopping and restaurants. Enjoy the ease of single-level living with thoughtful updates throughout. Recent improvements include an updated bathroom, new driveway (2026), siding and Trex deck (2025), and furnace (2018), with the roof replaced in 2011. Move right in and enjoy a comfortable home with a great combination of updates, convenience, and low-maintenance living

This charming Cape has been lovingly maintained and offers 3/4 bedrooms. The first floor features a bright and inviting living space, two comfortable bedrooms, and a full bathroom, making one-level living an option. The eat-in kitchen offers new appliances. Upstairs you'll find a third bedroom along with a versatile bonus room-perfect for a craft room, home office, playroom or guest space. With many recent upgrades throughout, this home offers true move-in-ready convenience and peace of mind for years to come. Outside, enjoy the attached screened-in carport, creating a wonderful three-season space for relaxing, entertaining, or enjoying summer. Conveniently located close to shopping, restaurants and all that Pittsfield has to offer !

Located in a desirable neighborhood in Southeast Pittsfield, this three-bedroom, 1.5-bath home offers comfort, versatility, and exceptional value. The main residence features spacious living areas, large primary bedroom with walk in closet and laundry room, and a functional layout designed for everyday living. A standout feature of the property is the attached first floor apartment with an additional bedroom, and additional bathroom, perfect for extended family, guests, rental income, or a private home office. The property also includes an insulated workshop/barn, providing ample space for hobbies, storage, equipment, or small business needs. Enjoy outdoor living in the fenced backyard, ideal for pets, gardening, entertaining, or simply relaxing in your own private retreat

Investment Opportunity in Pittsfield! Well-maintained four-family flat offering four spacious 1-bedroom, 1-bath apartments. Each unit features separate utilities, providing tenants with individual responsibility for their utility costs. Natural gas heat and hot water add to the property's efficiency and appeal. Centrally located with convenient access to shopping, dining, schools, public transportation, and major routes. A great opportunity for investors looking to add a solid multi-family property to their portfolio or for an owner-occupant seeking rental income. Don't miss this centrally located Pittsfield four-family!

This lovely antique home is ready for its next chapter. Located close to downtown Great Barrington on over 2 acres, this property has mature perennial gardens and flowering trees galore. The home itself has a great layout and strong bones but will take imagination and work to make it into the dream home it deserves to be. An amazing opportunity in a beautiful location. House being sold as is

Relax and enjoy this spacious raised ranch, ideally situated on a quiet street just a 1/2 mile from Pontoosuc Lake. This inviting 3 bedroom, 2 bath home features a spacious living room, a generously sized kitchen and dining area, and plenty of room to entertain. The lower level features a terrific, office, workout or play area with laundry and 3/4 bath. Step outside to the enjoy the private rear deck and yard. The peaceful setting on a quiet street offers the best of both worlds-privacy and tranquility at home, while being just a short walk from the lake for boating, picnicking, swimming or simply enjoying the outdoors. Come see all this home and all its desirable location have to offer

Beautiful newly remodeled 3-bedroom Cape. Nothing to do but move right into this home. New roof, new siding, new windows, gutters, all exterior and interior doors. Updated kitchen with new appliances, new driveway with bluestone front steps, electric car charger in heated garage, large family room in basement and so much more. OPEN HOUSE SATURDAY 8/1 10:00AM-11:30am

Relax and enjoy this spacious raised ranch, ideally situated on a quiet street just a 1/2 mile from Pontoosuc Lake. This inviting 3 bedroom, 2 bath home features a spacious living room, a generously sized kitchen and dining area, and plenty of room to entertain. The lower level features a terrific, office, workout or play area with laundry and 3/4 bath. Step outside to the enjoy the private rear deck and yard. The peaceful setting on a quiet street offers the best of both worlds-privacy and tranquility at home, while being just a short walk from the lake for boating, picnicking, swimming or simply enjoying the outdoors. Come see all this home and all its desirable location have to offer

First time ever offered! Single Level Living Surrounded by Gardens You'll Fall in Love With Lovingly maintained by the original builder's family, this cherished ranch is ready for it's next chapter. Recently refinished hardwood floors, a fireplace, and a sun filled four season room with French doors overlooking established perennial gardens create a warm and inviting atmosphere. Years of thoughtful gardening have transformed the backyard into a peaceful retreat. A newer roof offers added peace of mind, while the home's solid craftsmanship is ready for your personal touch. A rare opportunity to own a home filled with quality, character, and timeless appeal in one of Pittsfield's desired neighborhoods

Well maintained 4 bedroom, 2 full bath cape set on a level quarter acre with mature landscaping! The first floor offers comfortable living space along with a full bathroom. Upstairs you will find additional bedrooms and a second full bath, so there is a full bathroom on each level. The home's electrical was upgraded in 2025. Other major updates include a brand new garage built in 2025 and a roof from 2020. Newer Andersen windows throughout. Gas fired hot water heat and a full basement offering plenty of room for storage and workshop space. Vinyl siding on the exterior. Nothing left to do but move in!

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

Move in ready home with vinyl siding, replacement windows and gas heat. Close to conveniences and a walk to Allendale Elementary School. 3 or 4 bedrooms as den on 1st floor could be used as a fourth. Half bath with laundry hookups on 1st floor as well. Stainless appliances in the kitchen. Comfort and character in this well kept home and a fireplace for those cozy nights. Just move in

Open house cancelled! Charming Cape Living on 1.16 Acres with Beautiful Views Welcome to 27 Madden Road! This inviting 3-bedroom, 2-bath Cape offers comfortable living and a versatile layout. The main level features an open floor plan with a spacious living room and fireplace, eat-in kitchen, full bathroom, and first-floor primary bedroom. Upstairs are two additional bedrooms and a second full bath. The finished lower level adds extra living area with a walkout, perfect for an office, gym, or hobby space. Set on 1.16 acres, there is plenty of room to relax, garden, entertain, and enjoy the surrounding views. Enjoy EZ Solar and property taxes under $800 per year, making this a great Berkshire getaway or year-round home!

Wake up each morning to breathtaking sunrises over beautiful Pontoosuc Lake from this exceptional waterfront retreat. Perfectly positioned to capture panoramic water views, this stunning 4 bedroom, 3 bath home offers the ideal blend of comfort and style. An inviting open-concept floor plan is designed to maximize the spectacular views, seamlessly connecting the spacious living, dining, and kitchen areas to create the perfect setting for entertaining or simply relaxing by the water. Outside, enjoy the the expansive Trex decking overlooking the lake, a large private dock, gazebo and an outdoor shower. Whether your are searching for a year round lakefront home or the ultimate vacation getaway, this home delivers lake life at its best! The first floor features generous living spaces for entertaining friends and family, two bedrooms, and a full bath. The spiral staircase ascends to the second floor primary suite with lovely updated primary bath, walk in closet, and walls of windows and skyl

Welcome home to this charming and well-maintained three-bedroom, two-bath property located in a desirable neighborhood just moments from Allendale School, downtown Pittsfield, shopping, dining, and everyday conveniences. This inviting home offers a wonderful blend of character and comfort, featuring beautiful hardwood floors in excellent condition, vinyl replacement windows, and a cozy wood-burning fireplace that creates a warm and welcoming atmosphere. The updated kitchen offers excellent functionality, with all appliances included for the new owner's convenience. A standout feature of the home is the gorgeous sunroom addition, complete with soaring ceilings, skylights, and direct access to the backyard-an ideal space to relax, entertain, or enjoy the changing seasons year-round. Upstairs, you'll find spacious and oversized bedrooms offering plenty of room to spread out. Outside, the flat, fenced-in backyard provides a great setting for outdoor enjoyment, gardening, pets, or gathering

Charming, move-in ready, and full of possibilities, this 3-bedroom, 1-bath home offers 1,428 square feet of comfortable living space. Inside, you'll find a bright and inviting layout with beautiful hardwood floors, an updated kitchen with plenty of cabinet and counter space, and a spacious upstairs that offers flexibility for bedrooms, a home office, or additional living space. Set on a manageable 0.18-acre lot, the property also offers a nice yard with room to relax, garden, or entertain. A great option for first-time buyers, those looking to downsize, or anyone searching for a home that's ready to enjoy from day one. Come see all this sweet property has to offer!

Nestled in a quiet cul-de-sac in one of the area's most desirable neighborhoods, this beautifully maintained 3-bedroom, 2 1/2-bath home offers the perfect combination of comfort, space, and location. Inside, you'll find beautiful hardwood floors and a thoughtfully designed floor plan ideal for everyday living and entertaining. A Spacious kitchen granite counters, cherry cabinets, newer appliances and a breakfast bar. Large sunroom overlooking the backyard offers the perfect place to relax, with plenty of natural light. Charming front porch adds to the home's inviting curb appeal and provides the perfect place to enjoy the quiet rhythm of the cul-de-sac. With its ideal location, inviting spaces, and effortless livability, this home isn't just a place to live-it's a place to truly feel at home

Open House Sunday August 2 From 2:30 to 4:00. Looking to enjoy lakeside living year round' This one bedroom home sits on three contiguous lots which provide the opportunity to expand your living space in the future. It overlooks it's own private lake lot allowing you to enjoy lakefront activities and everything that Ashmere Lake has to offer The home features an open floor plan with large windows overlooking the lake. At one end of the cathedral ceiling, a ship's ladder leads to an enclosed bonus room above the large bedroom The lower level walkout has a foyer entrance, multipurpose room, including the laundry room and a mechanical room Outside you'll find a separate deck, fire pit, and a large grassy yard with plenty of room for a garden. This property includes four lots. With Water Front on Ashmere Lake

Relax and enjoy this spacious raised ranch, ideally situated on a quiet street just a 1/2 mile from Pontoosuc Lake. This inviting 3 bedroom, 2 bath home features a spacious living room, a generously sized kitchen and dining area, and plenty of room to entertain. The lower level features a terrific, office, workout or play area with laundry and 3/4 bath. Step outside to the enjoy the private rear deck and yard. The peaceful setting on a quiet street offers the best of both worlds-privacy and tranquility at home, while being just a short walk from the lake for boating, picnicking, swimming or simply enjoying the outdoors. Come see all this home and all its desirable location have to offer

Tucked well back from the road on 3.5 private acres, this modern, lightly used home offers an effortless blend of low-maintenance living, single-story convenience, and quintessential Berkshires charm. Designed with an open, light-filled layout, the main level features gleaming hardwood floors and an seamless flow throughout the common living areas. At the heart of the main floor is a inviting living room with a gas fireplace framed by a stone surround and hearth, an updated kitchen, and a generous primary suite complete with a large walk-in closet.Enjoy indoor-outdoor living with a covered front porch, a spacious screened porch, and an expansive wrap-around deck perfect for entertaining or taking in the peaceful surroundings.The expansive finished walk-out lower level extends your living The expansive finished walk-out lower level extends your living space, equipped with cozy radiant heated floors, high-efficiency boiler system, and a flexible unfinished bonus room ready for custom exp

Come relax amid sweeping pastoral and mountain views in this exceptional retreat designed for both entertaining and everyday comfort. The impressive great room, anchored by a massive stone fireplace, offers a welcoming focal point and flows into a spacious well-designed kitchen/dining area. A screened porch with fireplace overlooks the pool and rolling landscape, creating a seamless indoor-outdoor experience. The first-floor primary suite features a luxurious bath and tranquil views. An exceptional cinema room includes theater-style reclining seats and a half bath. Generous guest accommodations throughout. A private office suite with full bath. Outdoors, enjoy an infinity pool, bluestone patios, lush gardens, a charming pool house - all just three miles from downtown Great Barrington

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

Here's your chance to spread out. This ranch home sits on 3 private acres in Cheshire, giving you the space to garden, entertain, or just breathe without sacrificing convenience. Built in 1973, the home offers classic ranch living with the single-level layout buyers still ask for. Unlike a lot of properties with this kind of acreage, you're not out in the middle of nowhere. Shopping, schools, and the daily essentials are all a short drive away. If you've been searching for room to roam without the long commute that usually comes with it, this is the one to see

This exquisite single-family home spans an impressive 4,300 square feet, offering an unmatched blend of elegance and modern comfort. With 5 spacious bedrooms and 4.5 beautifully renovated bathrooms, every detail has been meticulously crafted to perfection. Walking distance to downtown Great Barrington's shops and restaurants, the house is in one of the quietest areas of 'The Hill'. 12 rooms including a formal dining room, a sophisticated library/den, and a versatile media/recreation room. The chef's kitchen, featuring premium counters, a WOLF range, a Sub Zero refrigerator, a wine cooler, and a butler's pantry for seamless entertaining. The home is filled with natural light. Comfort is ensured year-round with air conditioning and central heating on every floor

Duplex in the hills of Housatonic. Three bedroom, one bathroom on each side. Enclosed front porches and open back porches, large garage, all on a corner lot. Located on the Grove St turn overlooking the village of Housatonic and only a few short steps from the Flag Rock conservation area, this is both in town and in a lovely mountain setting. Both units have large walk-up attic and basement spaces. On-site laundry, updated heating system and electrical, newer roof, and solar. This home is an excellent owner-occupied or investment opportunity. One side currently vacant

Impeccably maintained contemporary home set on four manicured acres bordering Massachusetts Fish and Game conservation lands and surrounded by approximately 4,500 acres of protected land in Hinsdale. Enjoy a private, serene setting just 1.6 miles from 287-acre Ashmere Lake. Inside, open entertaining spaces blend seamlessly with quiet retreats. The main level features a designer kitchen with granite countertops, Wolf range, and breakfast bar flowing into the dining area. A light-filled great room with gas fireplace offers year-round comfort, while a three-season screened porch and expansive decks invite outdoor dining. Three bedrooms include a first-floor primary suite with attached office or reading room. Additional highlights include 2.5 baths, laundry room, oversized two-car garage, and a massive basement with workbench and abundant storage. Just 30 minutes to Tanglewood, under 3 hours to Boston, and just over 3 hours to Manhattan

Lovely five bedroom two bath Colonial on 5500+ sq.ft. of land.Lots of space, front porch for relaxing on beautiful summer evenings. Two bedrooms on the first floor and three bedrooms on the second floor with a deck off the bedroom and off the kitchen on the first floor. Two driveways for plenty of parking!Three sheds on property for storage will stay. Or not

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

Gracious, elegant, and designed for living well, this exceptional center hall Colonial offers timeless character, beautiful mountain views, and an abundance of space. The welcoming entrance is accented by exquisite English stained glass, with wood floors flowing throughout the home. Five bedrooms and 3.5 baths provide room for family and guests, while grand living and dining rooms are perfect for entertaining. A spacious family room offers a more relaxed gathering space. The primary suite features cathedral ceilings and beautiful mountain views. Outside, covered patios and decks overlook a spectacular in-ground pool, gazebo, and bathhouse-creating a private setting for summer entertaining and relaxation. Thoughtful updates include a 2016 roof, 2023 driveway, and appliances updated 2023-26 The first floor also has a private office with bamboo floors, an updated kitchen with granite counter, island seating and dining space with sliders to the deck. First floor laundry. The finished lower

Located in a desirable neighborhood in Southeast Pittsfield, this three-bedroom, 1.5-bath home offers comfort, versatility, and exceptional value. The main residence features spacious living areas, large primary bedroom with walk in closet and laundry room, and a functional layout designed for everyday living. A standout feature of the property is the attached first floor apartment with an additional bedroom, and additional bathroom, perfect for extended family, guests, rental income, or a private home office. The property also includes an insulated workshop/barn, providing ample space for hobbies, storage, equipment, or small business needs. Enjoy outdoor living in the fenced backyard, ideal for pets, gardening, entertaining, or simply relaxing in your own private retreat