569 houses for sale in Great Barrington

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!

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!

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 renovated single floor home in Housatonic, just minutes from downtown Great Barrington, Tanglewood, and everything the Berkshires have to offer. With direct access to the Rail Trail, this move-in ready home is set on.93 acres, the property features a spacious yard and greenhouse, offering plenty of room to relax, garden, or entertain. The updated kitchen features stone countertops, stainless steel appliances, an induction range, and new LVP flooring. Both bathrooms have been fully renovated with Schluter waterproof systems. Additional upgrades include smart Lutron lighting with Alexa control, a Rheem smart hot water heater, Ring cameras, new 200-amp electrical service, a new driveway and retaining wall, irrigation system, freshly painted exterior, and a new septic installed in 2025!

Newly renovated single floor home in Housatonic, just minutes from downtown Great Barrington, Tanglewood, and everything the Berkshires have to offer. With direct access to the Rail Trail, this move-in ready home is set on.93 acres, the property features a spacious yard and greenhouse, offering plenty of room to relax, garden, or entertain. The updated kitchen features stone countertops, stainless steel appliances, an induction range, and new LVP flooring. Both bathrooms have been fully renovated with Schluter waterproof systems. Additional upgrades include smart Lutron lighting with Alexa control, a Rheem smart hot water heater, Ring cameras, new 200-amp electrical service, a new driveway and retaining wall, irrigation system, freshly painted exterior, and a new septic installed in 2025!

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

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!

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!

Newly renovated single floor home in Housatonic, just minutes from downtown Great Barrington, Tanglewood, and everything the Berkshires have to offer. With direct access to the Rail Trail, this move-in ready home is set on. 93 acres, the property features a spacious yard and greenhouse, offering plenty of room to relax, garden, or entertain. The updated kitchen features stone countertops, stainless steel appliances, an induction range, and new LVP flooring. Both bathrooms have been fully renovated with Schluter waterproof systems. Additional upgrades include smart Lutron lighting with Alexa control, a Rheem smart hot water heater, Ring cameras, new 200-amp electrical service, a new driveway and retaining wall, irrigation system, freshly painted exterior, and a new septic installed in 2025!

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

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

SUN DRENCHED MODERN HOME WITH POOL AND PRIVACY, A SHORT WALK TO THE WALDORF SCHOOL AND THE GREEN RIVER. This gorgeous property consists of 2 separate building lots and is on a lovely, 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

Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot w/ almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many recent updates and upgrades including kitchen,bathrooms as well as furnace and central AC system replacement. All of this and a heated community pool nearby and Great Barrington just minutes away, make this home ready for the next owners to create their own Berkshire journey and memories. -REPLACED/UPDATED WITHIN LAST 3 YEARS: furnace,central AC, kitchen,bathrooms,all exterior doors, stand by auto generator, basement improvements -8 homes in the community -HOA DUES WILL DECREASE TO $900 PER QUARTER ($300 PER MONTH) AFTER TWO LOANS ARE PAID OFF IN JULY AND OCT 2027. -RENTAL POLICY: FIRST RENTAL TERM:

Renovated, well-maintained, multi-use building perfect for a live-work situation in prime location! All 4 floors offer opportunity for offices, a studio, storage, retail showroom and more! Highlights include: a large parking lot, handicap accessible ramp, 2 half baths and finished 3rd floor attic. Finished basement w/ vault and video security system. The current retail space is bright and sunny with a large quartz s counter, display shelves, spot lights, fresh paint, with modern pendant lighting. The impressive metal roof and boiler were both installed in 2019, along with the emergency generator and mini splits throughout. The building's total of 3000 sq ft is based upon renovations. (See floor plans in documents.) B2 zoning offers many options for permitted use! (See GB bylaws in documents.)

Step into effortless Berkshire living in this design-forward mid-century ranch. Perfectly positioned on a quiet downtown dead-end road, this 3-bedroom, 1-bathroom home seamlessly blends crisp, modern style with classic architectural character. Inside, original hardwood floors guide you through a bright, fluid one-level layout. The living room serves as a comfortable anchor for cozy mountain evenings, featuring a striking wood stove that pairs perfectly with the home's fresh, stylish aesthetic. Outside, the generous 0.41-acre level lot offers a private, shaded yard surrounded by mature trees-a fantastic feature for a property this close to the action. Beyond its residential charm, this property boasts coveted Business zoning, making it perfect for an ideal live-work lifestyle

Step into effortless Berkshire living in this design-forward mid-century ranch. Perfectly positioned on a quiet downtown dead-end road, this 3-bedroom, 1-bathroom home seamlessly blends crisp, modern style with classic architectural character. Inside, original hardwood floors guide you through a bright, fluid one-level layout. The living room serves as a comfortable anchor for cozy mountain evenings, featuring a striking wood stove that pairs perfectly with the home's fresh, stylish aesthetic. Outside, the generous 0.41-acre level lot offers a private, shaded yard surrounded by mature trees-a fantastic feature for a property this close to the action. Beyond its residential charm, this property boasts coveted Business zoning, making it perfect for an ideal live-work lifestyle

Neat as a pin cape walking distance to downtown Great Barrington and amenities, this home has been thoughtfully renovated top to bottom. This sweet property, also zoned commercially, has 4 bedrooms, a full bath, and even a partially finished basement. The kitchen, complete with a large pantry, retains the charming mid century details, while appealing to the modern aesthetic. Outside, there is a nice flat side yard, and views of the Housatonic river winding below. Clean and classic, all you have to do is move in and start making it your own!

Situated on Great Barrington's highly sought after neighborhood of 'The Hill', 11 Prospect delivers on style, convenience and of course, location! This four bedroom home with two and a half baths over three floors and hardwood floors throughout, offers lots of room for family and friends. An oversized screened in porch, attached two car garage and a finished basement are just some of the 'must haves' to enjoy in this recently updated property. Steps away from the shoreline of Lake Mansfield and a simple stroll to downtown Great Barrington's many coffee shops, restaurants, bakeries and theaters, this property is the perfect move in ready home!

A Rare Find: This lovely Victorian is waiting for a new family. Currently a two family but can be converted to a single family. Lovely Woodwork and it even has a pocket door. Close to restaurants and entertainment. Call today for a showing

Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered clapboard. Inside, original period charm takes center stage with wide-plank wood floors and glowing fireplaces, perfectly paired with a rare, substantial footprint featuring 7 generous bedrooms and 6.5 bathrooms. Designed for effortless hosting, this expansive retreat offers an incredible canvas for a lucrative rental investment, a boutique bed-and-breakfast, or a magnificent private country compound

CONTEMPORARY FARMHOUSE! Sited on a knoll dotted with old apples trees overlooking scenic views all framed by a meandering fence. All you could ask for is in this well-built home, offering a first floor primary ensuite, library with fieldstone fireplace, A well appointed kitchen opens to both the dining and a living room with fireplace. A screen porch, 1/2 bath, laundry room/mudroom leading to a 2 car garage completes the first floor. The second floor offers 3 addition bedrooms, full bath, built-in bookcase with window seat. Kick back and relax on the front porch! A fabulous Berkshire house close to all Berkshire cultural venues, skiing, shopping, restaurants and, just plain fun!

The mid-century retreat you've been waiting for. This classic home sits on over 4 private acres, delivering the ultimate Berkshire lifestyle with a bright, open floor plan and two cozy fireplaces. With 4 bedrooms, 3 baths, a large office, and a sun room looking overlooking your oasis, the layout offers perfect flexibility for guests or remote work. Outside, your private resort features a heated swimming pool and a dedicated tennis or pickle ball court tucked at the end of a quiet road for unmatched seclusion. Modern upgrades including a large solar array and a new heating system drastically reduce utility costs. Experience total privacy while staying minutes from everything that makes Great Barrington a premier Berkshire destination

Rare offering of over six acres 'On the Hill', sprawling residence with first floor primary, large eat-in kitchen with cozy fireplace. porch-privacy-garage. open acreage bordered by woods. walking distance to Main Street, Skiing and Lake Mansfield nearby. Five bedrooms, three baths. Formal living room. Plenty of room for expansion

Custom built home situated on a private lot just minutes to GUIDOS! Impeccable home with open floor plan. kitchen, eating area, living room with fireplace. wood floors, tiled baths, gas heat, central air, established gardens including your very own blueberry patch!. A stunning house on a very special piece of take a look.

Positioned within walking distance to the vibrant downtown of Great Barrington, this property offers a unique opportunity for Homeowners, investors, non-profits, or developers seeking flexibility and future upside. Previously utilized as professional offices for mental health services, with vision, this could be converted into a 1 or 2 family home. Significant capital improvements have already been completed, including a newer boiler, newer hot water heater, a fully monitored smoke and CO detection system, and all windows replaced, ensuring efficiency and peace of mind for future ownership. The property sits on over one acre of land and features a large on-site parking lot and adjacent to a beautiful river. clients, or residents. Zoned residential, this property presents compelling redevelopment potential. Whether you envision a conversion to a single-family residence, multi-family housing, or a mixed-use concept (subject to approvals), the location and infrastructure support a wide ra