581 houses for sale in Great Barrington

PUBLIC OPEN HOUSE: Saturday October 10 from 10-1. See you there! Enjoy the relaxing Berkshire lifestyle on a friendly cul-de-sac within walking distance of town and Lake Mansfield. As the first house built on the street, the property has matured beautifully - seasonal flowering trees and pollinator-friendly gardens bring color and life to the yard from spring through fall. Cedar columns frame a distinctive front door that opens into 3,800 square feet of tastefully designed living space, where soaring ceilings, a linear gas fireplace, and built-in bookcases set the tone. The living room flows out to a screened-in porch with a treehouse-like view of the wooded backyard - the perfect spot for morning coffee or summer evenings. area and living room for easy entertaining. Also on the main floor: a primary suite with walk-in closet and spacious bath, two additional bedrooms (one with floor-to-ceiling built-in bookshelves), a full bath, a half bath, and dedicated mud and laundry rooms. Though

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

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:

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.

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. Newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, 4+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor gas grill. EV charging station in driveway. Walking distance to Lake Mansfield and Main Street shops, restaurants and theaters. House can be sold furnished

THIS HOME HAS BEEN UNDER CONSTRICTION SINCE 2018. PRICE DOES NOT REFLECT CURRENT MARKET CONDITIONS. PRICES ARE NOT AT THIS PRICE POINT ANY LONGER. Open plan living with, first floor master, fireplace, screened porch, high ceilings, two car garage, community pool. HOA covers all lawn maintenance, plowing, shoveling up to the front door. Quality New Construction. This price cannot be matched. 10 months to move into your beautiful new home. Photos are from a similar home with the same floor plan in the community, with upgrades. Build your dream home on one of the other beautiful lots. Single level with 2100 square feet or as large as 3800 square feet. 3-5 bedrooms with prices beginning at $689,000

Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence and generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette and massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard and patio, separate studio apartment and 4 garage bays, a barn, and cutting gardens. The custom home, built by one of the region's premiere builders, has been featured in design magazines, garden tours and has received a Garden Club of America award for its ethos and thoughtful use of b

Tucked away on an peaceful cul-de-sac off Lake Buel Road, this spacious, well-built, multi-level 3 bedroom, 2 full-bath home is priced approximately $200,000 below its current assessment, which supplies more than enough room for the interior renovation it needs and deserves. Originally built in 1997 and surrounded by 2.65 acres of wooded privacy, it was thoughtfully designed with over-sized rooms,a screened porch, open deck, interior access garage, laundry room, and separate basement area for storage. Located just minutes from Ski Butternut as well as Great Barrington's vibrant Main Street shops and restaurants, this is a fixer with excellent potential

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 separately - negotiable with owner

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:

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!

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!

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

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 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 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 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

Attention investors! This property features a primary bedroom with a half bath, along with three additional bedrooms, offering plenty of living space. The combined two lots total 7.99 acres, providing ample room for expansion. Having been vacant for several years, this property presents a blank canvas, ready for someone with a vision to restore it to its former glory. Potential buyers should be aware that the property does not qualify for FHA, CHFA, or government financing, so alternative funding will be necessary. Additionally, the buyer will be responsible for removing all items from the property. The property at 321 Salisbury Road spans 6.99 acres, and the adjoining lot at 313 Salisbury Road is 1 acre, which will be included in the transaction. Please note that the 313 Salisbury property has a vacant trailer on the lot, which the buyer will also need to manage. The property is being sold As Is. It has been inspected, and the septic system has failed the Title 5 inspection

Completely renovated and exceptionally versatile, this spacious 3-bedroom ranch is located in desirable Sheffield, MA. Set on a.50-acre commercially zoned lot just a 5 minute drive to downtown Great Barrington, the property offers outstanding investment, or business potential. The 2,258 sq. ft. main residence features 3 spacious bedrooms, a large new kitchen, full bath, washer/dryer, and garage. A brand-new adjoining apartment includes a new finished kitchen with granite countertops, washer/dryer, and private backyard access deal for rental income, or professional office use. Updates include a new 3-bedroom septic system and new roof, backyard fence and new grass. Some images have been digitally altered to include virtual staging

Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access to a wrap-around deck. Upstairs, a treehouse-like loft adds charm, while the primary suite delivers a spa-like experience. The three suites were designed for intimacy and privacy. The walk-out lower level houses a guest suite and fantastic game room. Renovated top-to-bottom with no expense spared, central A/C, and new mechanicals-just bring your suitcase. 15 mins to Guido's and 45 mins to the Wassaic NYC train

Nestled on a level in-town lot, this classic Colonial offers timeless charm, solid construction, and endless potential. Featuring three bedrooms and beautiful hardwood flooring, the home provides a warm and inviting layout ready for your personal touch. The front porch is THE perfect seasonal place to unwind after a long day or start your day with coffee! The adorable galley kitchen with convenient main-level laundry adds to the home's functionality, while a detached two-car garage offers additional storage and versatility. While the property could benefit from some cosmetic updates, it has been well maintained and stands on a strong foundation-making it the perfect opportunity to build equity and create your dream home. Located in the heart of Canaan, you'll enjoy the best of small-town living with the convenience of being able to walk right into town. Known for its scenic beauty and rich history, this charming Litchfield Hills community is home to the stunning Great Falls and the uni

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

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket doors that provide charm and flexibility. Every detail has been curated to embody warmth and sophistication, creating an inviting ambiance that is both refined and welcoming. Ideally located just moments from downtown Lenox, Tanglewood, a local municipal airport and a charming farm, HomeFarm, directly across the street. Highwick offers an unparalleled sanctuary in the heart of the Berkshires!

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and restaurants. Nestled amidst beautiful, well-maintained grounds, this residence exudes curb appeal. The apartments have all been thoughtfully updated and come equipped with outdoor space, access to laundry facilities, and exceptional parking

Welcome to this beautifully renovated and professionally decorated 3-bedroom, 2-full-bath ranch, offering the perfect combination of style, comfort, and easy one-level living! Thoughtfully updated throughout, this home features a spacious, flowing floor plan, abundant closet space, and tasteful finishes that create a warm and inviting atmosphere. The beautifully landscaped, level lot provides a wonderful setting for outdoor enjoyment, while the gorgeous rear stone patio is perfect for entertaining or simply relaxing. Recent improvements include new appliances, new windows, a new oil burner, updated electrical panel, totally renovated bathroom, and the addition of a third bedroom, adding valuable living space and functionality. The flexible layout also offers potential for an in-law arrangement, providing options for extended family or guests. Truly move-in ready, this exceptional home offers the charm of ranch-style living with the benefits of extensive modern updates

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations

Mixed use property located just 7 miles south of Gt Barrington on Route 7. Two commercial units and two residential units. Solar on roof and in back of property bring in additional lease revenue. Long term tenants in each apartment. Anchor commercial tenant, Berkshire Fence and Accessories, to sign long term lease with new owner. Second commercial unit vacant, perfect for owner occupied buyer

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 well-loved antique home offers a rare combination of history, thoughtful updates, and natural beauty. Set on 14+ acres with sweeping westerly mountain views, Carefully maintained over the years, the property has benefited from significant improvements, including an updated foundation, electrical and plumbing systems, heating system, windows, and roof. The home offers four bedrooms, two full baths, and a full basement, providing comfortable living space with the character and charm of an earlier era. Outside, the property unfolds across fields, gardens, mature fruit trees, and open land, with direct abutting state land and access to the Appalachian Trail nearby. An oversized detached garage with a second floor offers ample room for vehicles, equipment, storage, or a workshop. With its peaceful setting, mountain views, and connection to the surrounding landscape, this is a special property for someone who will appreciate its history and become its next steward