822 properties for sale in Housatonic

Built in 2021, this custom contemporary offers about 5,670 sq ft of finished living space on 2+ acres, just 5 minutes to Great Barrington center, with mountain views and sunsets to the west. The open first floor features vaulted ceilings, a propane fireplace and a chef's kitchen with a large island, coffee bar and generous storage, opening to the dining and living areas. A large screened porch extends the living space three seasons a year. A mudroom with laundry off the oversized 3-car garage, two offices and a powder room complete the main level. Upstairs, two guest rooms with en suite baths and a primary suite with fireplace and a large bath. The finished lower level adds about 1,900 sq ft: game room, gym, media room, guest bedroom and full bath. Central air, high-speed fiber available, and truly turnkey, with sunset views over the neighboring private airport

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires

Don't miss this Lenox beauty tucked away on a quiet side street. Main level w hardwood flooring, living room with crown molding, formal dining w. large bay window, updated kitchen w extensive cabinetry. Family room w gas fireplace opens to large screened porch / patio. First floor laundry and 1/2 bath. Three bedrooms on the upper level; primary suite w adjoining dressing room/ primary bath with soaking tub and separate shower. Two additional bedrooms and full bath; all w hardwood flooring. Central a/c; natural gas heat/hot water; attached two-car garage. Easy maintenance perennial gardens with a focus on native and specimen plantings -over 100 species carefully planned to bloom continuously wowing sight and scent! Abutting preserved land with year-round brook-your own magical retreat!

Experience elevated wellness living in this exceptional Canyon Ranch penthouse in Lenox. This 3,300+ sq. ft. residence offers three spacious ensuite bedrooms, a powder room, an expansive great room, a chef's kitchen and three fireplaces that create a warm, inviting atmosphere. A private patio provides the perfect retreat to relax and enjoy the natural beauty of the Berkshires. Ownership includes a requisite annual resort membership with full access to Canyon Ranch's world-renowned wellness amenities. Just minutes from the Berkshires' acclaimed cultural attractions, fine dining and outdoor recreation, this is a rare opportunity to enjoy luxury, wellness and timeless design in one extraordinary home

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion-with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision-be it modern apartments, stylish offices, retail space, or a dynamic studio. - Spacious and bright with 5,180 sq ft across two levels - Excellent bone

THE BEST OF GREAT BARRINGTON RIGHT OUTSIDE YOUR DOOR! Set high up on a knoll, this home boasts good, solid construction, wood floors, brick fireplace, a year round sunroom and a detached garage. The mature trees and perennials give the lot wonderful privacy. Easy manageable living, a block from the NYC bus this classic Berkshire house with the luxury of leaving your car behind

Enjoy easy Berkshire living in this recently updated, bright and inviting 2-bedroom, 950 sq. ft. top-floor condo. An oversized slider brings in an abundance of natural light and creates a more open, spacious feel. Set within a pet-friendly community, residents enjoy a gas BBQ/picnic area, children's playground, tennis and pickleball courts, heated pool and walking trails. Comfortable and convenient, this condo is ideal as a year-round home or Berkshire getaway The Berkshires is widely celebrated as 'America's Premier Cultural Resort' offering a unique blend of world class arts, historic estates, and scenic natural beauty. Close to shopping, dining, Tanglewood, and endless outdoor recreation, this is a wonderful opportunity to own in Lenox at an attractive value

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial built-ins create a sophisticated yet comfortable totally renovated interior. Outside, magnificent perennial gardens, privacy, outdoor showers, and courtyard provides a serene retreat. Enjoy access to the nearby Wyndhurst Club and Manor pool, tennis courts, reduced-rate fitness membership, and more. A rare offering combining luxury, lifestyle, and one of Lenox's most coveted settings

'ON THE HILL' Cozy 4 bedroom 1925 Cape, HOUSE BEING SOLD 'AS IS' WALK TO TOWN AND LAKE MANSFIELD. Living room with mini split, custom built cabinets in DR, Large primary bedroom with mini split, large family room, OPEN FRONT PORCH WITH VIEWS. BACK YARD PATIO FOR COOK OUTS. Attached 1 car garage, TOWN WATER AND SEWER. So much charm, house needs updating. DONT MISS THIS GEM !

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

Terrific opportunity to own a piece of Historic Lenox. Set back from the road, secluded by deciduous shade tree. Spacious front lawn and close to village This is a diamond in the rough and with some sweat equity could be a shining star. Original wood floors throughout. One car garage and garden shed in backyard which is very private. HW heater 1 yr old. Enclosed Porch has new footings and roof is about 8 years old. Call today for your private viewing. Won't last long

Pristine, Move-In Ready End-Unit with Unobstructed Meadow Views and Paid-in-Full Assessment Skip the stress, delays, and skyrocketing costs of renovating a fixer-upper. This exceptional, updated end-unit in the highly sought-after Rolling Hills community offers the ultimate move-in-ready Berkshires retreat, combining premium privacy with unmatched financial value. While other units in the area may require immediate, out-of-pocket improvements, this home is completely updated and waiting for you. The Premium Location Advantage Positioned as a rare end-unit, this property offers a level of privacy most units simply cannot match. Your living spaces look out onto gorgeous, unobstructed views of protected meadows and woodlands. Watch deer, foxes, turkeys, and vibrant birdlife change with the seasons directly from your private deck and sliding glass windows. Resort-Style Amenities Just 4 Minutes from Historic Lenox Center Leave the lawn care and snow removal behind. Your monthly fees grant y

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation and a separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry

TO BE BUILT: Gorgeous neighborhood setting with lush landscaping and Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 3,808 sq ft of thoughtfully designed, environmentally conscious living less than a mile from downtown Great Barrington, this home is the perfect modern retreat. Enter through a covered portico into a soaring cathedral-ceiling great room filled with natural light and serene woodland views. A wonderful screened porch expands the living space for peaceful mornings or easy entertaining. The open layout seamlessly connects the living, dining, and chef's kitchen, featuring premium appliances, quartz countertops, and a spacious island. A sophisticated split-bedroom design. Modern conveniences include a first-floor laundry, advanced electric heat pump systems promoting energy efficiency, and an electric vehicle charging station in the garage

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.

MOTIVATED SELLER'S! This property has an immaculate fenced in back yard for all your summer activities. Inside boasts beautiful hardwood floors, Full bath on the 1st and 2nd Level. Large mudroom from the main entrance for all you winter and mud season needs. A paved driveway with plenty of private parking. A walkout from the lower level to the parking area with a tuck under car port. Recently painted exterior and a screened in porch in the back. 3 large bedrooms and a perfect den for office space or media room. Centrally located in the Berkshires within close proximity to Shopping, Groceries Stores and Tanglewood!

This charming and move-in ready home invites you to settle into an easy Berkshire lifestyle. The first floor offers the comfort of one-level living, with a bedroom, full bath, laundry, and welcoming living spaces, while the second floor provides additional bedrooms and room for guests. Recent updates include an updated electrical service, refreshed interiors, and a beautiful enclosed porch made for slow mornings and quiet evenings. Just moments from shopping and dining, with downtown Lenox minutes away, Bousquet Mountain Ski Resort and Sports Center 4 minutes away, and Tanglewood about 10 minutes away. Spend your days exploring scenic trails, discovering local favorites, or enjoying the beauty of the Berkshires in every season

Looking for one level living' Must see ranch in the southeast. This Polo Acres updated home is just over the Lenox line and close to all the Berkshires have to offer. Enter from the covered porch into a spacious welcoming entry. The light-filled living room with fireplace and gleaming wood floors flows into the dining area and three-season sunroom with awning. The large kitchen opens to a flagstone patio for outdoor dining and BBQs. First-floor laundry adds convenience. Primary suite with full bath/walk-in shower plus two additional bedrooms and a second full bath. Enjoy the partially fenced yard, oversized two-car garage, and full basement with a 2nd fireplace and large windows offering the potential for future living or recreation space

Beautifully renovated and thoughtfully designed South Pond Farm unit located in a serene setting. Great circular flow with walls of windows bringing in the wooded view and natural light. The main level offers a great room with wood burning fireplace and built ins, open brand new kitchen and dining, charming den, new washer and dryer and refreshed half bath. Second floor boasts the gracious primary with en suite new bath, second guest bedroom, new guest bath and flex space with skylight. The lower level has been modified into a second primary bedroom retreat with sitting/media area, new bathroom, office and bedroom with walk out. Front patio, attached oversized garage with new EV charger and spacious deck complete this property. Association beach on Richmond Pond, pool and tennis court. Convenient location near cultural attractions and amenities here in the Berkshires

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 for sale separately. Negotiable with owner. Near all the cultural events specific to the Berkshires!

Pristine, Move-In Ready End-Unit with Unobstructed Meadow Views and Paid-in-Full Assessment Skip the stress, delays, and skyrocketing costs of renovating a fixer-upper. This exceptional, updated end-unit in the highly sought-after Rolling Hills community offers the ultimate move-in-ready Berkshires retreat, combining premium privacy with unmatched financial value. While other units in the area may require immediate, out-of-pocket improvements, this home is completely updated and waiting for you. The Premium Location Advantage Positioned as a rare end-unit, this property offers a level of privacy most units simply cannot match. Your living spaces look out onto gorgeous, unobstructed views of protected meadows and woodlands. Watch deer, foxes, turkeys, and vibrant birdlife change with the seasons directly from your private deck and sliding glass windows. Resort-Style Amenities Just 4 Minutes from Historic Lenox Center Leave the lawn care and snow removal behind. Your monthly fees grant y

Welcome to this charming 4-bedroom, 2-bath home offering the perfect blend of comfort, updates, and extra living space. The updated kitchen and renovated first-floor bath provide modern style and convenience, while the finished lower level adds versatile space for a family room, home office, gym, or guest area. A bright and inviting sunroom fills the home with natural light and offers the perfect place to relax year-round. Outside, enjoy a spacious fenced backyard ideal for entertaining, pets, or play, along with an oversized garage providing ample storage and workspace. As an added bonus, the property includes deeded lake rights with private access to Onota Lake, giving you access to enjoy nearby water activities and scenic surroundings

Welcome to this beautiful and inviting home in Pittsfield's most sought-after Southeast neighborhood. This is a unique opportunity to live at Wellesley Park, a small city-owned and beautifully maintained park, where homes rarely come on the market because once you live in this community, you will never move again! This well maintained, light-filled 2,100 square foot home boasts a large formal living room with over-sized picture windows at each end and fireplace; a very large kitchen with five-burner cooktop and double wall ovens; an office, half bath; dining room; and den making up the downstairs. The second floor has three very roomy light-filled bedrooms, closets galore, a large full bath, as well as hardwood floors throughout nearly the entire home (including under the carpeting in thformal living room). All of this sitting on a gorgeous lot with the home set well back from the road, a double-wide driveway, mature landscaping and located in the southernmost section of Pittsfield mak

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

Immaculate 3-bedroom ranch with additional 750 square feet of finished living space in lower level. Move in condition, cathedral ceiling in living room and 2 full baths, Prmary with ensuite. Set way back off Park Street North on 0.62 level acres. 8+ acres owned by Land Conservation in your back yard adds peace and privacy

This move-in-ready 4-bedroom, 2.5-bath Colonial in Southeast Pittsfield sits on over half an acre and blends classic charm with thoughtful updates. The welcoming chefs kitchen opens to a screened porch and flows into a generous dining room with built-in cabinetry, perfect for everyday living and entertaining. A light-filled living room anchored by a wood-burning fireplace creates a warm and inviting gathering space. Upstairs offers four comfortable bedrooms, two full baths, a large cedar closet, and abundant storage. A two-car garage and partially finished basement with a second wood-burning fireplace complete this exceptional home. Outside, the professionally landscaped, fully fenced backyard offers exceptional privacy and outdoor living space. Recent major improvements include: New roof Central air conditioning Newer furnace Replaced sewer line Newer appliances Freshly painted exterior What truly sets this property apart is its remarkable history. Lovingly cared for by only three own

TO BE BUILT: Gorgeous neighborhood setting with lush landscaping and Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 3,808 sq ft of thoughtfully designed, environmentally conscious living less than a mile from downtown Great Barrington, this home is the perfect modern retreat. Enter through a covered portico into a soaring cathedral-ceiling great room filled with natural light and serene woodland views. A wonderful screened porch expands the living space for peaceful mornings or easy entertaining. The open layout seamlessly connects the living, dining, and chef's kitchen, featuring premium appliances, quartz countertops, and a spacious island. A sophisticated split-bedroom design. Modern conveniences include a first-floor laundry, advanced electric heat pump systems promoting energy efficiency, and an electric vehicle charging station in the garage

Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. Ft. Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. A state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling

Moments from Lake Mansfield and Main Street, this turnkey contemporary offers clean lines, natural light, and effortless Berkshire living. The main level features an open-concept floor plan anchored by a show-stopping Duvemala tiled stove, serving as a striking centerpiece for gatherings and cozy evenings by the fire. Enjoy the convenience of a first-floor bedroom alongside one of the home's three well-appointed full baths. Upstairs, an expansive primary suite impresses with vast cathedral ceilings. The finished lower level adds a versatile bonus room, providing extra square footage for a home gym or game room. Outside, relax and entertain on the sun-soaked deck overlooking the oversized grounds of this rare double-sized parcel

Rare opportunity to own a beautifully restored Berkshire cottage at 17 Main Street, perfectly situated in the vibrant heart of downtown Lenox. This remarkable property, originally built in 1883 and once the residence of Gilded Age shipping magnate John Schermerhorn, combines historic elegance with modern comfort. The home underwent a comprehensive renovation between 2021 and 2025, including a new 30-year roof, upgraded electrical and plumbing, 8.5 renovated bathrooms, custom millwork, and restored original hardwood floors. The gourmet kitchen features a Viking 8-burner oven, KitchenAid designer dishwasher, and commercial-grade refrigeration-ideal for private entertaining or everyday living. All systems are new, including a four-zone HVAC and seven mini-splits for year-round comfort. With eight bedrooms (plus potential for a ninth), five fireplaces with new gas log sets, and inviting communal spaces, this home offers in-town living at its best. Enjoy the ultimate walk-to-everything life