660 properties for sale in Great Barrington

Newly updated Housatonic cottage set on the corner of Kirk and Fairview. Two bedrooms, two baths, lovely living space, and a sweet screened porch and patio. The lot has potential for expanded gardens or recreational space. Seasonal views to Flagg Mtn. A perfect location and setting

Set on a sunny half-acre lot, this classic 1900 ranch is ready for its next chapter and top/bottom reinvention.The home is now strictly an 'as-is' handyman special or contractor's dream. Features a cozy compact ( yes small ) kitchen, vintage vibes (meaning every room needs a facelift ),and dirt basement. Roof is holding strong for now, but you'll want to budget for a replacement soon (real sooner) The real star here? The land and location, half-acre of fantastic, usable Berkshires property, you have ample room to expand, build new, or execute a total dream renovation. Title V not complete, seller will not repair fails, will be the responsibility of the Buyer. Showings must be scheduled; the home is occupied. Won't qualify for most lending products

El Refugio, 'The Refuge', a hidden gem minutes from downtown Great Barrington. A 2-bedroom, 2-bath, wood burning fireplace home - with a 46' heated pool and 2-car detached garage. Set back from the road on 7+ private acres with extensive shoreline on the Williams River

Set on a sunny half-acre lot, this classic 1900 ranch is ready for its next chapter and top/bottom reinvention.The home is now strictly an 'as-is' handyman special or contractor's dream. Features a cozy compact ( yes small ) kitchen, vintage vibes (meaning every room needs a facelift ),and dirt basement. Roof is holding strong for now, but you'll want to budget for a replacement soon (real sooner) The real star here' The land and location, half-acre of fantastic, usable Berkshires property, you have ample room to expand, build new, or execute a total dream renovation. Title V not complete, seller will not repair fails, will be the responsibility of the Buyer. Showings must be scheduled; the home is occupied. Won't qualify for most lending products

This well-maintained mixed-use property offers excellent flexibility for both commercial and residential use. The building is currently configured as two separate units. The first floor features a bright commercial space with large front-facing windows that provide excellent visibility and natural light-ideal for office or retail use. The space includes a private bathroom, dedicated heating and air conditioning, and a water filtration system for added convenience. The second floor offers a comfortable three-bedroom residential unit with a full bathroom, an open-concept kitchen and dining area, and attractive wood flooring throughout. The property is equipped with two separate heating systems to efficiently serve each unit. Additional highlights include ample parking in front and back

Newly updated Housatonic cottage set on the corner of Kirk and Fairview. Two bedrooms, two baths, lovely living space, and a sweet screened porch and patio. The lot has potential for expanded gardens or recreational space. Seasonal views to Flagg Mtn. A perfect location and setting

Discover a unique condo in a converted mill building where historic factory character meets modern style in the heart of Housatonic. Soaring ceilings and beautiful wood floors throughout complement two generously sized bedrooms, one full bathroom, a large living room with views of Flag rock and a spacious dining room. An enclosed porch offers a cozy spot to unwind while a community deck provides space to relax and gather. Enjoy local restaurants and numerous hiking trails just moments away. Come see what makes this distinctive condo such a special place to call home

Located on a quiet street in Housatonic, this charming cottage offers easy single-level living in a peaceful neighborhood setting. Set on a sunny double lot, the property provides extra outdoor space and flexibility with room to garden, entertain, play, or simply enjoy the surroundings. Inside, the home features an efficient layout filled with natural light, creating a bright and comfortable feeling. An oversized garage adds valuable storage and space for hobbies, tools, or workshop use. One of the highlights of this location is being within walking distance to Old Maids Park, where you can enjoy fishing, swimming, and a picnic area along the river. This sweet cottage offers a wonderful opportunity for those seeking a manageable home with everyday simplicity and nearby recreation. Minutes to downtown GB, and local amenities!

Newly updated Housatonic cottage set on the corner of Kirk and Fairview. Two bedrooms, two baths, lovely living space, and a sweet screened porch and patio. The lot has potential for expanded gardens or recreational space. Seasonal views to Flagg Mtn. A perfect location and setting

Motivated sellers are ready to move! Built in 2019 on 1.73 private acres in Housatonic, this well-maintained 3-bedroom, 3-bath ranch offers approximately 2,915 sq. ft. of finished space. The main level features a primary suite with walk-in closet and private bath, laundry, and red oak flooring milled from trees harvested on the property. The finished walkout lower level offers a large recreation room, full bath, and additional rooms for guests, hobbies, an office, or entertaining. Enjoy a Trex deck, covered patio, above-ground pool, and wooded surroundings. This detached condominium includes exclusive use of the home, yard, pool, deck, driveway, sheds, and grounds-offering single-family privacy. Annual property taxes are approximately $8,164; buyers should verify with the municipality

Discover a unique condo in a converted mill building where historic factory character meets modern style in the heart of Housatonic. Soaring ceilings and beautiful wood floors throughout complement two generously sized bedrooms, one full bathroom, a large living room with views of Flag rock and a spacious dining room. An enclosed porch offers a cozy spot to unwind while a community deck provides space to relax and gather. Enjoy local restaurants and numerous hiking trails just moments away. Come see what makes this distinctive condo such a special place to call home

Located on a quiet street in Housatonic, this charming cottage offers easy single-level living in a peaceful neighborhood setting. Set on a sunny double lot, the property provides extra outdoor space and flexibility with room to garden, entertain, play, or simply enjoy the surroundings. Inside, the home features an efficient layout filled with natural light, creating a bright and comfortable feeling. An oversized garage adds valuable storage and space for hobbies, tools, or workshop use. One of the highlights of this location is being within walking distance to Old Maids Park, where you can enjoy fishing, swimming, and a picnic area along the river. This sweet cottage offers a wonderful opportunity for those seeking a manageable home with everyday simplicity and nearby recreation. Minutes to downtown GB, and local amenities!

This well-maintained mixed-use property offers excellent flexibility for both commercial and residential use. The building is currently configured as two separate units. The first floor features a bright commercial space with large front-facing windows that provide excellent visibility and natural light-ideal for office or retail use. The space includes a private bathroom, dedicated heating and air conditioning, and a water filtration system for added convenience. The second floor offers a comfortable three-bedroom residential unit with a full bathroom, an open-concept kitchen and dining area, and attractive wood flooring throughout. The property is equipped with two separate heating systems to efficiently serve each unit. Additional highlights include ample parking in front and back

Mixed-use property in vibrant Housatonic village center. Three flexible units: two residential apartments above commercial space. Prime location within walking distance to local shops, art galleries, restaurants, town library, and neighborhood park with playground. Stunning views of the iconic Housatonic water tower and historic mill town industrial architecture. Property features mature gardens, private walled patio area, three dedicated parking spaces, plus rear garage requiring renovation work. Perfect investment opportunity for entrepreneurs seeking rental income or business owners wanting live-work space. The building offers excellent potential in this growing creative community hub with strong local character and charm. A must see!

Special opportunity to take over the 5BR owners' unit as part of this 4-unit compound and let the other 3 pay your mortgage. Relaxing property in the center of Housatonic village with two charming, recently renovated duplex homes - each with historic details left intact. The front house has a flex 4/5BR 2200 sq. foot owners' unit which feels like its own house. Split on 2 floors, it has 2 full baths, privacy, its own screened-in porch and outdoor BBQ area. Currently operating as a high-end furnished rental. Use it as your FT residence, weekend home or mid-term rental (i.e. traveling nurses), turn-key and ready to go. The remaining 3 x 2BR units are filled with wonderful tenants; each home has their own W/D, outdoor space and there is an expansive shared yard- -in back with fruit trees and a community garden. Property includes plenty of parking for all and entrepreneurs take note: it is zoned mixed-use so the street-facing rooms, currently separate and used as storage, can be turned int

Set on a sunny half-acre lot, this classic 1900 ranch is ready for its next chapter and top/bottom reinvention.The home is now strictly an 'as-is' handyman special or contractor's dream. Features a cozy compact ( yes small ) kitchen, vintage vibes (meaning every room needs a facelift ),and dirt basement. Roof is holding strong for now, but you'll want to budget for a replacement soon (real sooner) The real star here' The land and location, half-acre of fantastic, usable Berkshires property, you have ample room to expand, build new, or execute a total dream renovation. Title V not complete, seller will not repair fails, will be the responsibility of the Buyer. Showings must be scheduled; the home is occupied. Won't qualify for most lending products

Rare, renovated Berkshire investment compound on 0.59 acres in walkable Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Walk to Berkshire Mountain Bakery; minutes to Great Barrington and Tanglewood. A rare, turnkey find!

El Refugio, 'The Refuge', a hidden gem minutes from downtown Great Barrington. A 2-bedroom, 2-bath, wood burning fireplace home - with a 46' heated pool and 2-car detached garage. Set back from the road on 7+ private acres with extensive shoreline on the Williams River

Motivated sellers are ready to move! Built in 2019 on 1.73 private acres in Housatonic, this well-maintained 3-bedroom, 3-bath ranch offers approximately 2,915 sq. ft. of finished space. The main level features a primary suite with walk-in closet and private bath, laundry, and red oak flooring milled from trees harvested on the property. The finished walkout lower level offers a large recreation room, full bath, and additional rooms for guests, hobbies, an office, or entertaining. Enjoy a Trex deck, covered patio, above-ground pool, and wooded surroundings. This detached condominium includes exclusive use of the home, yard, pool, deck, driveway, sheds, and grounds-offering single-family privacy. Annual property taxes are approximately $8,164; buyers should verify with the municipality

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Truly, a one of a kind, stunning property both inside and out with scenic views of the sprawling land down to Long Pond. This thoughtfully crafted and designed home was curated to incorporate the natural serene outdoors into gracious open common spaces allowing warm natural light and comfortable flow. The first floor boasts the great room with wood burning fireplace open to the chefs kitchen with a large pantry and dining with built ins, unique sunroom with walls of glass and screened porch that extends the indoor outdoor living space while overlooking the pergola, play house and down to the water. The first floor primary en suite and office/den sitting area offer privacy in its own separate wing. The second level has ample guest space with three bedrooms, two en suite full baths and guest laundry. Completing the home on the lower level walkout is the guest suite with family room, private kitchen, two more additional bedrooms, office, full bath and patio. All of this set way back from

MOTIVATED SELLER*Nestled in the heart of Great Barrington, this spacious 4 bedroom, 4 bathroom residence offers the perfect blend of family-friendly comfort and private sophistication. The home greets you with gleaming wood floors and a stunning fieldstone fireplace that anchors the living spaces in warmth and character. Cook like a chef in the large open kitchen, where generous countertops, a welcoming island, and ample natural light inspire everyday gatherings. The first-floor primary suite provides convenience without sacrificing privacy, ideal for busy households seeking single-level living when desired. Step outside to your expansive outdoors: a grand deck that overlooks lush acreage, plus a screened-in porch and an oversized porch ideal for morning coffees, evening entertaining, and quiet moments surrounded by nature. This property delivers both space for growing families and the seclusion you crave, all within the desirable Great Barrington lifestyle-top schools, outdoor adventu

SUN DRENCHED MODERN HOME WITH POOL AND PRIVACY, ON ONE OF THE MOST COVETED ROADS IN THE BERKSHIRES. This gorgeous property consists of 2 separate lots and sits on the loveliest quiet road ideal for walking and biking, and only 7 minutes drive to Guido's. The house, which has been recently completely reimagined and added onto, is an ode to sophistication, beauty, and practicality. 4+ bedrooms, 3.5 baths, Open plan sun filled kitchen/dining/living, walk in pantry, generous entry with built in benches and storage, TV room with custom shelving, bright office, and a loft like studio above the 3 car garage. For outdoor living, the mahogany deck runs along the back of the house and connects to a comfortable screened porch with plenty of room for dining and lounging. A welcoming family retreat!

Your private Berkshire retreat! Sweeping views of Squaw Peak, surrounding mountains, 42 beautiful sub-dividable acres with trails, seasonal brook, room for pool, tennis court, family compound. Warm, welcoming 4BR, 4.5 bath, home with room for family, friends, gathering or quiet escapes. Sun-filled fireplaced LR with picture window, cozy window seat framing the view; elegant formal DR with window wall and fireplace. Spacious chef's kitchen with island, dining area, TV area, comfy wood stove, leading to the large screened porch and expansive deck-perfect for morning coffee, summer dinners or simply relaxing. 3 main-level BRs include ensuite primary. Above-grade LL offers office, 4th BR, bath, inviting fireplaced family room. 2-car garage. 1 mile to downtown Great Barrington

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

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

A rare French Manor estate gracing one of South Berkshire's most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary is awaiting buyers final finishes and offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook-creating a secluded retreat that feels worlds away, yet remains moments from the cultural heart of the Berkshires. SEE LIST OF ITEMS TO BE FINISHED IN DOCUMENTS. At the center of the estate stands a newly built main residence inspired by the grand proportions of the Gilded Age, featuring soaring 19-foot ceilings and impeccable architectural presence. Thoughtfully constructed by a highly regarded local craftsman, the home showcases state-of-the-art mechanical systems, including geothermal heating and cooling, blending classic elegance with modern efficiency. Approaching completion, the residence presents

This meticulously maintained 1900 farmhouse seamlessly blends timeless historic character with refined modern updates, creating a move-in ready retreat just minutes from the vibrant energy of downtown Great Barrington. Every corner of this classic three-bedroom, two-bathroom home reflects thoughtful care and craftsmanship, offering an ideal balance of warmth, functionality, and quintessential Berkshire charm. At the heart of the residence is a stunning cook's kitchen, thoughtfully renovated and fully outfitted with updated appliances, expansive counter space, and storage. Sunlit living spaces flow naturally throughout the main floor, showcased by rich, beautifully preserved wood floors that anchor the home in timeless elegance. Architectural charm continues outdoors with a classic front porch and a private back porch that adds seamless transitional space between the interior and the grounds. Outside, the property transforms into a true personal oasis, featuring thoughtfully designed pa