775 houses for sale in Housatonic

A rare offering of 118 acres in the highly sought-after Tyringham Valley. Sage Hill Farm encompasses an exceptional landscape of rolling meadows and woodlands, mature landscaping, exquisite gardens, beautifully crafted hardscape and handsome barns. Dating to 1817, the main house retains many of its original architectural details and is complemented by a partially renovated 1970s addition and separate 1941 guest house. The grounds are impressive, with a beautiful setting for the heated in-ground pool and ample areas to enjoy the property's extraordinary acreage. The original house and addition offer generous accommodations for family and guests, including six bedrooms and four bathrooms, two of which are roughed for plumbing. The inviting and comfortable guest house with 3 bedrooms and 3.5 baths, accessed by its own driveway, includes a garage/barn and is reached by a charming walking bridge over Hop Brook (see Documents for further details about the guest house). An exceptional opportu

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

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 & 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, dedicat

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

Sited down a long shared drive this lovely contemporary colonial style home is incredibly private. Circular drive brings you around the front entry, the current owner extended the house to give it a proper entry and created a lovely front porch. The living space is flanked with windows to the private backyard and open to the kitchen and dining area. A large great room sits on the south side of the home and the soaring ceilings and multiple skylights give it a solarium feel flooding it with light. Kitchen is large with good working space, a pantry closet, counter seating and french doors to the screened porch and patio. The side entry brings you from the 3 car detached garage through the coveted boot room into the kitchen with laundry tucked away. Upstairs there are 3 guest rooms, a hall bath and a primary suite. The primary has a working fireplace, a balcony over the great room with a sauna and potential office space. A truly private setting yet close to all the Berkshires has to offer

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

Newly constructed and thoughtfully designed, this home is ideally located within the Copake Lake community-Columbia County's only high-speed motorboat lake-and built by one of the area's most respected contractors. The property reflects quality craftsmanship throughout. The home offers 3 bedrooms and 3 full bathrooms, including two primary suites on the main level. The third bedroom is on the lower level currently used as additional living space. The open-concept great room combines the living area with a gas fireplace, ample space for dining, and kitchen with custom cabinetry and stainless steel appliances that includes double ovens. There is also a large full basement with potential for future expansion. Additional features include a heated two-car garage, an attached carport, an in-ground pool, and a beautifully maintained lawn with a protected vegetable garden with raised planting beds. The property is privately set among the trees while remaining close to lake access and activitie

This beautifully maintained, turnkey retreat offers 3,424 square feet, four bedrooms, two-and-a-half baths, a resort-style saltwater pool, and a peaceful private setting just minutes from Hudson. Designed for full-time living or weekend escapes, the spacious layout offers room for entertaining, remote work, and perfect for hosting family and friends. Outdoors, enjoy an in-ground fiberglass saltwater pool, an illuminated pergola with electricity and a ceiling fan, a custom fire pit, and multiple areas for dining and relaxing. Fiber-optic internet adds modern convenience, while the move-in-ready condition allows you to enjoy the Hudson Valley lifestyle immediately. The famous Bartlett House cafe and bakery is just down the road, with Hudson’s restaurants, shops, galleries, cultural attractions, and Amtrak station approximately 12–15 minutes away. Convenient to the Taconic State Parkway, Lake Taghkanic, hiking, skiing, and year-round recreation. Approximately two hours from New York City,

Great New Price! Discover the timeless charm of this beautiful turn-of-the-century Victorian, showcasing the craftsmanship and character of its era. Inside, you'll find impressive 9-foot ceilings, detailed crown molding, beautiful hardwood floors, and charming built-ins that highlight its classic architectural beauty. Spacious, sun-filled rooms offer plenty of room for entertaining, relaxing, and everyday living. Recent updates, including a newer furnace, windows, and roof, add to the home's appeal while preserving its distinctive character. Tucked away in a peaceful setting yet conveniently located close to downtown, this generously sized home offers the perfect blend of historic charm, everyday comfort, and endless possibilities for its next owner!

Welcome home to this beautifully maintained and thoughtfully cared-for residence, ideally situated on one of Southeast Pittsfield's most desirable dead-end streets. Offering exceptional curb appeal, mature landscaping, and a peaceful garden-like setting with a wonderfully private backyard, this charming home showcases quality craftsmanship, timeless character, and pride of ownership throughout. Designed for both everyday living and entertaining, the spacious sunroom is filled with natural light and overlooks the backyard, creating the perfect place to relax or gather with family and friends. Step outside to enjoy the inviting in-ground pool, private patio, and tranquil outdoor setting. A first-floor family room with direct access to the backyard provides additional living space and creates a seamless connection to outdoor entertaining, while the thoughtfully designed floor plan offers comfort, function, and flexibility throughout. Inside, you'll appreciate the home's quality finishes,

Built by Thomas Colt in 1865, 42 Wendell Avenue is a striking Italian Villa style property with a rich place in Pittsfield's history. Once owned by Simon England Sr who deeded it in memory of his wife, the building later became the Women's Club of Pittsfield and most recently served as the Whitney Center for the Arts. The arched entrance opens to more than 7,700 square feet across 15 rooms. Soaring ceilings, inlaid hardwood floors, ornate fireplaces, carved wood mantels, and substantial original woodwork lend character throughout. Tall windows bring natural light into the rooms, and a sunroom offers a bright space overlooking the grounds. The property's scale and layout invite a range of possibilities. Rooms on both floors could accommodate professional offices or studios, while the large rooms offer space for meetings, performances, or exhibitions. Multiple apartment spaces upstairs add residential possibilities, complemented by a commercial sized kitchen and an on site parking lot. W

Completely renovated contemporary home on almost 10 acres of marvelous land. The home sits back from the road, offering tranquility and privacy. The first floor features two bedrooms and an additional room with a wood-burning fireplace which can be used as a recreation room or a third bedroom. Downstairs you will also find a large laundry room with epoxy flooring, and a brand new full bathroom. The second floor offers an open concept and features a brand new kitchen with quartz countertops, a great room with a wood stove, a cozy dining area and a new full bathroom with a jetted tub. You will feel like you are at a spa! Relax and enjoy nature from your tub or step outside to the new deck that wraps around the home. The property has great quality flooring, from terracotta Mexican tile to walnut wood. Other improvements include new LP SmartSide siding, a new electrical service, roof, plumbing, windows and mini-splits throughout that provide both heat and A/C. A detached garage and a recen

Set on just under 4 acres along County Route 7, this property offers a farmhouse ready for restoration and a straightforward starting point for creating something of your own. The house is ready for updating and restoration, with a well and septic system already in place. With the subdivision currently in process, the property offers a manageable amount of land and plenty of room to shape the setting around the existing farmhouse. The location puts you minutes from Copake Lake and approximately 12 minutes from the Taconic State Parkway, with Hudson and Great Barrington both within easy reach. Surrounded by the landscape and amenities of the Hudson Valley and Berkshires, this is a property with a solid foundation and a blank slate for its next chapter

Step inside this turnkey 4-bedroom, 1.5-bath New England farmhouse and immediately feel at home. Additional room/office space on the first floor. Fully renovated in 2022 and freshly painted from top to bottom (2026), this vacant beauty is completely ready for its next chapter. The traditional farmhouse aesthetic offers timeless appeal, while the 2022 updated bring modern comfort and style. Outside, retreat to your own backyard for privacy and entertainment. Best of all, this property comes with a letter of full de-lead compliance, offering rare and valuable peace of mind

'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

This newly remodeled 2 family home boast 3+ bedrooms and 1.5 bathrooms on one. The work has been completed and it's ready for either a rental property or an owner occupied home. The renovations include, new kitchens, bathrooms, floors and also a new boiler in 2026. The laundry rooms are conveniently located in units. There is off street parking, a large private back yard with a shed. Conveniently located just a short walk to the Elm St area and Downtown

Welcome home to this renovated 1910 Tudor-style Ranch ideally located in a premier neighborhood. This charming home offers the perfect blend of timeless character and easy modern living. Original architectural details, beautiful woodwork, and period charm have been thoughtfully preserved while the home has been updated for today's lifestyle. Featuring 3 bedrooms, 2 baths, and a detached 2-car garage, the inviting floor plan is comfortable, functional, and move-in ready. A truly special home that delivers the character buyers love with the convenience they're looking for

Welcome to 1100 Harlemville Road, a c. 1850 farmhouse set on more than nine bucolic acres with sweeping views across the Taconic Hills. Perched above the road, the property enjoys a sense of privacy and a setting that feels quintessentially upstate. The drive approaches the rear of the home, where a covered porch offers the perfect vantage point to enjoy the landscape. Enter through a mudroom clad with vibrant wallpaper. Checkered tile floors lead to a spacious country kitchen; patterned tin accenting the walls lend character and texture. A generous pantry conceals the refrigerator while providing ample shelving and storage. The kitchen flows seamlessly into the dining room, anchored by a wood-burning stove. Just beyond, a cozy reading room is adorned in geometric wallpaper and opens to the grounds through French doors. Across the foyer, the living room connects to a dedicated office, offering flexibility for work or quiet retreat. Upstairs, a generous landing leads to three bedrooms a

A rare opportunity to acquire two neighboring properties, offered together on separate lots, in a desirable Pittsfield neighborhood. The former Pilgrim Holiness Church presents a distinctive space filled with character and exciting possibilities for adaptive reuse, creative pursuits, community-oriented activities, or future redevelopment. Next door, the former rectory is a well-maintained Cape offering comfortable living space and the potential for rental income, an owner's residence or on-site accommodations. Together, these properties create a compelling investment package with flexibility rarely found in a single offering. The separate lots add versatility for future ownership, use, or development strategies, subject to applicable zoning and municipal approvals. Whether envisioned as a live-and-work arrangement, an income-producing investment or a thoughtfully reimagined property, this unique Elm Street offering provides an outstanding foundation in a convenient and established Pitt

Nestled within a mixed use residential/commercial block this renovated space is ready for the next creative commercial endeavor. Rent the house and use the studio for art, office, store or Live and work all within walking distance to town center. Thoughtfully brought from a commercial office space to a 2 bedroom, 1.5 bath, bright open and airy living space with 5 parking spots and a nice size yard

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26

Welcome to this beautifully renovated 3-bedroom ranch, perfectly situated on a quiet dead-end street in Southeast. This move-in-ready home features a brand-new roof, new windows, new flooring throughout, and a completely updated kitchen and bathroom. The thoughtful renovations offer a fresh, modern feel while maintaining the comfortable layout and easy living of a classic ranch. Outside, enjoy a fenced-in backyard-ideal for entertaining, gardening, pets, or relaxing. With major updates already completed and a peaceful location to call home, this property is a fantastic opportunity for buyers!

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

Find Your North Star in the Berkshires! The pinnacle of value priced $250,000 below appraised value and $450,000 below assessed value! A private enclave near premier Lake Onota to experience idyllic living in the Berkshire hills while creating lasting memories. This stunning 6000+ sf, 5 Bedroom, 5.5 bath colonial is thoughtfully designed and beautifully set on 3.42 manageable acres with sweeping meadow views nestled perfectly to create peace in nature while centrally located minutes to the culture, arts, museums, eclectic dining and central to Tanglewood and The Clark Art. Three levels of living create a blend of fun and entertainment with a degree of separation on levels. First floor offers one level easy living with a dramatic two story primary bedroom su Second floor boasts heightened enjoyment with four spacious bedrooms spanning a second story balcony. Lower level offers a theatre, gym, gaming space plus a full bath. Looking to store your collection of toys see the 50 x 40 BONUS o

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

Southeast brick cape ready for summer fun! This 3 bed 2 bath cape is filled with warmth, character, and inviting spaces ready for memories all season long. Bright open kitchen, which flows to the dining area and family room with vaulted ceilings and doors to the deck. Around the corner a 2nd family room, game room or whatever you decide with wood burning fireplace. 1st floor also offers spacious bedroom and full bathroom. Upstairs 2 more bedrooms with character (one having the cutest nook!)and full bath with skylight! An attached one car garage offering every day convenience. Outside there is a large entertaining deck area with steps down to a patio. Perfect for outdoor BBQ's or smores by the fire at night. Plentiful outdoor space with comfortable living space makes this home a true gem!

Attention Investors and Portfolio Builders! Exceptional turn-key opportunity to acquire a high-yield, fully leased 2-family home in Pittsfield. Built in 1880, this solid Colonial-style income-producer delivers an ideal layout optimized for low landlord overhead and immediate, stable cash flow from day one. A standout feature of this asset is the entirely separate utility infrastructure, substantially lowering your operational expenses. The downstairs unit (Unit 1) features a comfortable 5-room, 2-bedroom, 1-bathroom unit. The sprawling upstairs unit (Unit 2) offers a spacious 6-room configuration, including 2 traditional bedrooms plus a flexible bonus room-perfect as a 3rd bedroom or home office-complete with its own dedicated in-unit laundry room. With separate meters in place, the tenants handle their own primary utility bills, keeping your net operating income predictable and protected. Both units are used as 3 Bedroom units. The property sits on a low-maintenance 2,613 sq. ft. lot

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!

Perched on a hill overlooking a scenic valley road, this 4-bedroom Dutch Gambrell offers a secluded country setting just a few minutes from town. This vibrantly-designed home opens into a handsome petrol-green kitchen with polished concrete floors and an ample dining area framed by French doors. The kitchen/dining area flows into an inviting living room anchored by a herringbone tile propane fireplace, a warm gathering space for family and friends. Just off the living room the 1st floor primary suite is a cheerful retreat with it's own striking classic black-and-white tiled bath with glass shower surround. Upstairs 3 guest bedrooms, a full bath and an upstairs playroom/lounge offer plenty of room for guests to relax. On the basement level there are two unheated semi-finished spaces for exercise and Media viewing. The lush back yard features a beautiful stone patio and hot tub. An attached 2-car garage with EV charging completes the package. Easy access to hiking, swimming, and everythi

Rural Sophistication Meets Eclectic Charm in Ghent. A captivating country retreat less than two hours from New York City. Tucked away among serene pines, this cedar-clad residence blends classic design with ecelctic architectural style including a wrap-around front porch and rooftop turret. Enjoy views from every room of the beautifully manicured lawns that transition into private wooded trails among fields of wildflowers. Designed for seamless indoor-outdoor living, the home features multiple points of egress leading to a tranquil swimming pond and a private tennis court. The open plan first floor features a living room with wood-burning fireplace, dining area and new chef kitchen with stainless steel appliances and breakfast bar. Completing the first floor is a bedroom and full bathroom. The second-floor features two large bedrooms with ample storage and ensuite bathrooms. Both opening out to elevated terraces with sweeping views of the grounds and surrounding hills. Cherry molding a