775 houses for sale in Housatonic

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90+/- acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams and Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and a collection of buildings added during its later evolution into an educational campus. Despite decades of institutional use, much of the character of the original country house remains. Handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom recall Overlee's Gilded Age origins. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors, creating an intriguing foundation for its return to residential use. Beyond the main house, the campus includes two dormitory residences with appro

HOME BEING SOLD AS IS NO NEGOTIATION ON INSPECTION ISSUES. THE PRICE IS NOT NEGOTIABLE. Two family minutes from downtown Lenox. First floor unit has 2 bedrooms with spacious living area and kitchen. Upstairs unit is a 1 bedroom, 1 bath with fireplace and back deck. Roof replaced in 2021, natural gas, town water and sewer

Beautiful, well maintained ranch that's move-in ready! Located in the desirable Southeast. This home features a three season sunroom and patio where you can relax and enjoy a private fenced-in yard. A large eat-in kitchen with granite counters, stainless steel appliances, pantry closet and comfortable dining area. Two bedrooms, one bath with walk-in shower. For convenience the laundry is located in one of the second bedroom's closets. Plenty of storage space between closets, attached garage and shed. Tastefully landscaped walkway as you enter this lovely home!

Welcome to this beautiful home dead end location AND is the QUEEN OF THE LAKE on Robinsons Pond! Amazing 101' of water frontage! Situated high on the property this one of a kind home enjoys incredible, beautiful waterfront views. The exterior stone walls give this home unprecedented distinction. 3 Full levels of outdoor living and possible entertaining space. The first floor features a Trek Deck with clear railings to sit and enjoy a cup of coffee or'whatever' lol while the sun sets or rises. The lower level enjoys a slate patio with 2 magnificent curved granite staircases on either side of the property to the yard/grass level. There is a totally separate private section/area that was built and is ready and waiting for your Hot Tub to be installed! What an unbelievable setting for any event, wedding, or just enjoying life in this fabulous property. The mid section of the yard is totally flat, completely fenced in with rod iron pretty fencing and can host any type of any party you can i

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

Bring your vision and creativity to this spacious side-by-side duplex that's been stripped down and prepped for its next chapter. Much of the heavy lifting has already been completed, including extensive demolition work and rough electrical installation. The exterior has also received a 1st of coat of paint. Originally intended to be converted into townhouses and sold separately, the owner's plans have changed, creating an exciting opportunity to customize a property to their needs. One unit offers 4 bedrooms and 1.5 baths, while the second features 3 bedrooms and 1.5 baths. Both units include private enclosed front porches, open rear porches, and spacious layouts ready to be transformed. The walkout basement opens to the backyard and offers additional possibilities. Whether you're looking to create income-producing rentals, pursue a townhouse conversion, or design your dream multi-generational property, this diamond in the rough is packed with potential

Historic character meets modern updates in this beautifully renovated 1880s home! Thoughtfully updated while preserving its original charm and integrity, the home underwent an extensive renovation in 2016, including new electrical, plumbing, insulation, and much more. Beautiful wood floors flow throughout, adding warmth and character. The first floor offers flexible living with a bedroom or home office and a full bathroom. Upstairs, you'll find three additional bedrooms, another full bath, and the convenience of second-floor laundry. There is also potential to expand the primary suite with space for an additional bathroom that has already been roughed in. Set on just over two acres, the property offers plenty of room to enjoy the outdoors along with a charming wraparound porch and a barn ready for restoration and new possibilities. A wonderful opportunity to own a piece of Pittsfield history with many of today's updates already in place!

Move-in ready and completely renovated! This home was remodeled down to the studs in 2023 with new wiring, plumbing, insulation, windows, and walls. Features beautifully refinished hardwood floors, new interior and exterior lighting, and a brand-new on-demand heating system. The first floor offers a large living room, dining room, kitchen, office, and half bath, while the second floor features two bedrooms and a luxurious full bath. There is additional storage in the bright lower level. Enjoy one of the largest lots on the street, conveniently located near Egremont School. Nothing to do but move in and enjoy!

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

Set in a peaceful West Pittsfield neighborhood, 35 Meadow Ridge is a sophisticated contemporary home with spacious thoughtfully designed living. Soaring 12 foot ceilings and cherry hardwood floors welcome you inside. The main level features a family room with built-ins, living room with gas fireplace, dining room, eat-in kitchen and access to the outdoor deck. The second floor offers an expansive primary suite, 2 additional bedrooms, 2 full baths, and flexible fourth room for use as bedroom, den or gym.A finished walk-out basement includes a family room and ensuite bedroom adding valuable space. This versatile home offers exceptional comfort and flexibility.Moments from Pittsfield State Forest, Onota Lake, downtown dining and short drive to Tanglewood. This is Berkshire living at its best!

Situated on highly desirable Mountain Drive, this expanded 3-bedroom, 2-bath Cape delivers classic Berkshire charm, thoughtful updates, and flexible living spaces. Step inside from the welcoming front porch into an inviting layout featuring hardwood floors and abundant natural light. The spacious living room is anchored by a wood-burning fireplace flanked by custom built-ins, flowing into the formal dining room and a tastefully remodeled kitchen. Enjoy year-round tranquility in the heated four-season sunroom or relax in the separate main-floor den featuring a cozy gas fireplace and sliders leading out to the rear deck. A generous first-floor bedroom, full bath, and dedicated laundry room offer effortless single-level living convenience. Upstairs, find a sprawling primary suite with a walk-in closet, a second sizable bedroom, and a fully renovated full bath. The lower level expands your entertaining footprint with a heated family/recreation room and workout space, alongside a large unfi

This property is sure to please those who are seeking privacy, land, and room for all the toys! Over three acres accompany this privately sited ranch home. Scenic and mountain views form the covered front porch. Living room w fireplace; eat-in kitchen, 3 bedrooms, 2.5 baths. Partially finished lower level with family room and second fireplace. The back yard has a generously fenced section. The attached/oversized two-car garage is heated for multi-purpose use. The first outbuilding includes two garage bays, has power and heat; there is an additional spacious storage shed, too. Enjoy the private rear patio and take in the open cleared lawn, ready for your own gardens, orchard, recreational space

Welcome home to this desirable Southeast Colonial! Offering classic character and thoughtful updates, this inviting home is move-in ready! From the charming front porch to the warmth and character of the gorgeous hardwood floors, the beautifully updated kitchen features abundant storage, granite countertops, an eye-catching island, dynamic lighting, and newer appliances, creating a wonderful space for everyday living and entertaining. French door leads to the deck overlooking the private yard and above-ground pool; perfect for morning coffee or relaxing outdoors.The first floor also offers a full bath, in-kitchen laundry, and barn doors opening to the living room/1st floor bedroom. Upstairs, you'll find three comfortable bedrooms and a second full bath. The perfect place to call home!

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

CLASSIC VILLAGE CENTER HOME WITH OFFICE - Graciously restored vintage home. Ideal in town location. Residential/Commercial zone. Private Office/Studio. High ceilings, wonderful light. Large modern Kitchen. Filled with period detail alongside modern updates. Radiant heat in baths. Spacious Primary Bedroom Suite. Wood burning fireplace in Living Room. 1st floor Laundry Room. New 4 bedroom septic 2023. 1,000 square foot outbuilding with water, electric service, and unlimited possibilities. This is a property with a long, rich history. It feels like home. Come see for yourself!

A rare opportunity to own 5.2 acres in Pittsfield for under $400,000! Set in the scenic countryside of West Pittsfield, this spacious 1820s farmhouse offers nearly 2,000 sq. ft. of living space, historic character, and room to make it your own. Inside, you'll find hardwood floors, a fireplace, beautiful central staircase, oversized bedrooms, enclosed porch, and walk-up attic. Updates include a hot water heater (approx. 3 years), boiler and replacement windows (approx. 5 years), carpeting (approx. 1 year), and rebuilt front and side porches. Enjoy the space and privacy of country living while remaining just minutes from the conveniences of Pittsfield

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

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

Immaculate and well-maintained contemporary home in an exceptionally convenient location set on 5+ wooded acres. Designed for easy living and low maintenance, this home offers an open floor plan with high ceilings, wood floors, and a beautiful fieldstone fireplace anchoring the main living space. The kitchen opens to another living area creating a comfortable flow for everyday living and entertaining. Enjoy the lovely screened porch and outdoor deck overlooking the natural setting. Three bedrooms and 3.5 baths, including guest quarters or apartment space for added flexibility. Large two-car garage. It is in a very private setting, but is also a short distance (walking distance) to the elementary and secondary schools. Easy transition for a first floor primary bedroom

Upper Rhoda Pond in Copake, New York (Southern Columbia County) is a very special place. About 2 hours from New York City, it is a private body of water with no public access. The waterfront area includes docks and a kayak to row out to your exclusive floating raft. This 3 bedrooms (plus office) has 3 bathrooms and is approximately 1944 square feet. The open floor plans lends itself to family, friends and entertaining. Wood-burning fireplace to warm up on those cool nights. Fiber-optic is on premises. The screened porch has panels, so that you can take in the country location and water views all year round. There is even a heater out there. The lower level has a sizeable family room and includes a pool table and ping-pong table. Storage has been very well organized and there is plenty of it. All this is sited on over 2.5 acres. There is a detached two-car garage and gardens. This central location makes it so convenient to so many cultural activities (Tanglewood, Catamount Adventure Mou

Location, location, location! Ideally situated within easy walking distance of the village, elementary school, and Tanglewood, this charming ranch offers comfortable single-level living in a quiet, desirable neighborhood. The large, level and semi-private backyard provides plenty of room to relax, entertain, garden, or enjoy the above-ground pool. Inside, the home features a spacious open living area currently used as a dining and family room, separate living room, eat-in kitchen, three bedrooms, and a full bath with tub. Step directly from the kitchen onto the deck overlooking the pool and expansive backyard. Additional highlights include an attached two-car garage, full basement with four versatile rooms, and a designated laundry space complete with a laundry chute!

A Little Whimsy, A Lot of Wow! Step into a bungalow bursting with personality, where timeless Craftsman charm meets thoughtfully curated updates, playful color, and extraordinary style! Beautifully reimagined while preserving its solid bones and original character, this home is anything but ordinary. A gorgeous new kitchen with stainless steel appliances and an island flows into a darling butler's pantry and beautiful dining room. The inviting living room steals the show with its oversized fireplace and rich Craftsman woodwork. Generously sized bedrooms offer incredible closet storage, while an updated bathroom and convenient mudroom add everyday practicality. The enchanting front porch is made for reading, writing, dreaming, and watching the world go by. Out back, a charming patio with a custom privacy screen overlooks a level, fully fenced backyard, creating your own little outdoor sanctuary. Perfectly positioned in a prime Southeast Pittsfield location, this is anything but an ordin

'A Perfect Place Farm' - a Berkshires Masterpiece on 17+ Acres The one you've been waiting for. a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home. Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley

Single level living with room for everyone. This well loved Ranch House sits in a quiet park like neighborhood on a cul-de-sac. Livingroom with Fireplace, Eat-in Kitchen, 3 Bedrooms + a Bonus Bedroom that may double as an ADU (accessory dwelling unit), Rental or In-law suite. Large yard. Private Deck. Well located near shopping and schools. Truly a special home

This property is sure to please those who are seeking privacy, land, and room for all the toys! Over three acres accompany this privately sited ranch home. Scenic and mountain views form the covered front porch. Living room w fireplace; eat-in kitchen, 3 bedrooms, 2.5 baths. Partially finished lower level with family room and second fireplace. The back yard has a generously fenced section. The attached/oversized two-car garage is heated for multi-purpose use. The first outbuilding includes two garage bays, has power and heat; there is an additional spacious storage shed, too. Enjoy the private rear patio and take in the open cleared lawn, ready for your own gardens, orchard, recreational space

Welcome to 4 Filomena Drive, where comfort meets the natural beauty of the Berkshires! Tucked away in a peaceful Southeast Pittsfield neighborhood, this inviting home offers a wonderful connection to the outdoors. Enjoy the tranquil backyard, bordered by a year round brook and beautiful views of the surrounding natural landscape. Whether you are grilling on the deck, entertaining on the patio, or simply enjoying the sights and sounds of nature, this property offers a perfect place to unwind. Inside, you'll find welcoming living spaces, an enormous finished basement, and plenty of room to make yourself at home. Enjoy the serenity of your own backyard retreat while staying just minutes from all the Berkshires has to offer!

Beautifully updated and lovingly maintained Colonial in the heart of Great Barrington. Bright, sunny, and truly move-in ready, this inviting home offers a combination of classic charm and comfortable modern living. The first floor features a welcoming mudroom, updated kitchen, heated sunroom, dining room, living room, family room, laundry, and full bath, providing plenty of space for both everyday living and entertaining. Upstairs are three comfortable bedrooms and a second full bath. Outside, enjoy a lovely yard and charming covered porch-perfect for relaxing and enjoying the neighborhood. Ideally located with easy access to Great Barrington's vibrant town center, library, restaurants, shops, and churches. A warm and beautifully cared-for home in a wonderful convenient location

Wonderful 1930 grand Hudson Avenue home, set way back from road with relaxing front porch for summer evenings, from a time when trains ruled in Chatham. Center-staircase colonial with open, eat-in kitchen, Dining Room, Den, and Living Room, all with new floors. Upstairs there are three bedrooms and a studio w/separate entrance, now open to the main house but easily changed back to another apartment. Pine floors in the Living Room and Dining Room, tile in the kitchen and baths, one bed room with a walk in closet and a small BR/office down and a nice Family Room complete the main floor. Three bedrooms up the renovated oak staircase gives plenty of living space and family privacy. A cottage in rear of the parcel for guests, studio or office. Currently two legal one-bedroom units which are vacant. Walk to everything-restaurants, movies, school, church, library, main street shops, and grocery stores. Wonderful location! Easy commute to Hudson, Albany, or Massachusetts! Tax based on 828,182

$10,000 back to you at closing, plus your first year of flood insurance paid. The seller is motivated and ready to make a deal. Tucked at the end of a quiet dead-end street, 96 Boylston gives you privacy you won't find this close to downtown Pittsfield. No through traffic, just a peaceful spot to come home to. Inside it's clean, updated, and move-in ready. The kitchen is the showstopper, wide open with new counters and appliances. New flooring and an updated bath finish it off. Use the $10k for whatever you want. Upgrades, closing costs, or whatever works for you. Come see it and make an offer

Privately set on just under 7 acres, this beautifully renovated home offers the perfect combination of tranquility, privacy, and convenience. A meticulously paved circular driveway leads through elegant, iron fencing to the level, beautifully landscaped property. The home offers approximately 2,800 square feet of thoughtfully updated living space, with 3 to 4 bedrooms and 2 full baths across two spacious levels. Natural light fills the interior, highlighting beautiful wood floors throughout and adding to the warm, inviting atmosphere. Skylights bring even more light into the home, while the oversized deck provides an ideal setting for outdoor entertaining, relaxing, and enjoying the peaceful surroundings. An oversized two-car garage offers generous parking and storage. Tucked away in a completely private setting yet just minutes from town, this exceptional property is approximately two minutes from Sheffield's Cobble and the Appalachian Trail, offering easy access to hiking, nature, an