Discover the timeless allure of 'The Turning Point,' a quintessential Berkshire retreat nestled in the hills of Great Barrington. Originally a 1800's stagecoach stop, this enchanting 3600-square-foot property boasts a rich history as a thriving inn, short-term rental and home, offering 7 bedrooms and 6.5 bathrooms. Immerse yourself in its New England charm, complete with a wood stove, propane fireplace, wide plank floors, large kitchen, first floor bedroom, office and a welcoming floorplan emanating warmth and comfort. Perfectly situated mere moments from Butternut Basin (one of the Berkshires top ski destinations) and a short drive from vibrant downtown Great Barrington, this charming sanctuary invites you to experience the best of Berkshire living.

Discover the timeless allure of 'The Turning Point,' a quintessential Berkshire retreat nestled in the hills of Great Barrington. Originally a 1800's stagecoach stop, this enchanting 3600-square-foot property boasts a rich history as a thriving inn, short-term rental and home, offering 7 bedrooms and 6.5 bathrooms. Immerse yourself in its New England charm, complete with a wood stove, propane fireplace, wide plank floors, large kitchen, first floor bedroom, office and a welcoming floorplan emanating warmth and comfort. Perfectly situated mere moments from Butternut Basin (one of the Berkshires top ski destinations) and a short drive from vibrant downtown Great Barrington, this charming sanctuary invites you to experience the best of Berkshire living.

Prime commercial frontage on Great Barringtons South Main Street. This Large building has been actively run as retail, manufacturing and residential housing for many years. This property is a perfect spot for a live/work scenario or to produce income.Currently this space has been used as two retail fronts, one space for manufacturing, one space for machine repair and two residential rental units on the second floor. With lots of parking the possibilities are endless!

Investment Opportunity - 4-Unit Mixed-Use Property in Downtown Great Barrington, MAPrime downtown Great Barrington location! This well-maintained 4-unit mixed-use property includes three 1-bedroom apartments and one street-level commercial space offering excellent visibility and steady foot traffic.Two of the residential units are currently occupied by long-term tenants with strong payment history, while two units (one apartment and the commercial space) are vacant, providing immediate value-add potential for an investor or owner-occupant.

With its excellent curb appeal, charm and location, this property delivers! The inviting exterior exudes timeless appeal, while the sun-drenched three season porch provides an ideal space to relax and enjoy the southeastern mountain views.. Inside, warm and flexible living spaces, a cozy fireplace, a bright & sunny dining nook with skylight, and other rooms that easily adapt to your lifestyle needs. Nestled in a sweet, welcoming neighborhood, this home promises the best of Berkshire living- comfort, whimsy and unbeatable location. Walking distance to Lake Mansfield, Main Street and Farmer's Market a short stroll.

Located just 1.8 miles from Ski Butternut, this Berkshires retreat is the perfect basecamp for multi-generational gatherings, or groups of friends who want room to spread out. Set on 4.32 private acres on the Great Barrington/Monterey line, this spacious 1958 ranch has grown over the years into an impressive 5,200 sq. ft. haven--ideal for creating lifelong vacation memories.Inside, the home's generous footprint and light-filled addition offer endless possibilities: multiple hangout zones, bunk areas, a game room, a ski-tuning corner, or even a cozy apres-ski lounge. Outside, the property provides instant access to miles of snowshoeing and cross-country skiing in your own backyard or on the Appalachian Trail.After a day spent skiing on the slopes or fishing and skating at

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation and a separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry.

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation & separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry.

Renovated commercial property (down to the studs!), located in prime GB main street location. Handicap access, two 1/2 baths, second floor staff kitchen, office space & finished attic for storage. Fully renovated basement with climate-controlled vault and high security make this building a rare find. Outside, there is plenty of off-street parking. Inside the main store sparkles with lots of white paint, ceiling lights and natural light. Top it off with a new metal roof (2019). Building total of 3000 sq ft is from the seller, based upon renovations. See floor plans in Documents. Dynamic Investment opportunity! (NOTE: The business is not for sale, just the building and land.)

6 Bay Car & Truck Service Center and Garage. Ideally located on the heavily trafficked Route 23 - Route 7 Corridor in the commercial center of Great Barrington. Private, secure fenced-in lot. Well maintained by Owner-User. Available with Lifts, & Equipment, if desired. Well priced and ideal for several types of use (...not just a Garage!).

Architectural gem with lots of glass perched like a treehouse on the backside of Monument Mountain. The open, mid-century modern home was built in 2012 for maximum light, efficiency, and provides glittering views through the trees of the Housatonic River! 2 bedroom, 2 full baths-both ensuite + central AC, and a Scandinavian soapstone wood stove, permit included! Minutes from hiking trails, Taft Farm, Berkshire Mountain Bakery and downtown GB. Also close to town schools, Butternut, Tanglewood, and other Berkshire cultural centers. So quiet, yet close to everything. Design by AIA recognized architect Steve Dietemann.

Welcome to 6 Lake Buel Road--a stunningly renovated 3-bedroom, 2-bathroom home set on 3.5 private acres in one of the Berkshires' most desirable locations. Just 1 minute to Butternut Ski Resort and 7 minutes to downtown Great Barrington, this property offers the perfect balance of peaceful seclusion and year-round convenience.Gutted and fully renovated within the last five years, the home features modern finishes throughout, an open floor plan, and high-end design elements. The chef's kitchen is outfitted with soapstone countertops, a commercial-grade range, and an 8 foot island--perfect for hosting or quiet weekends in. Slate floors run through the mudroom and kitchen, combining durability with timeless style.

Charming Renovated 1900 Colonial ''On The Hill''A beautifully updated home blends historic charm with modern amenities in a sought-after neighborhood. The thoughtfully opened floor plan features gorgeous wood floors and an abundance of natural light throughout. A chef's eat-in kitchen is complete with a center island and seamless flow into the spacious living room and den. A wood-burning fireplace anchors the space, creating a warm and inviting atmosphere. French doors open onto a fabulous wraparound porch perfect for entertaining or relaxing. The kitchen leads to a deck overlooking a beautiful fenced yard with a fire pit-- for cozy evenings outdoors. 4 bdrms, 2 baths. A sidewalk takes you to the vibrant downtown to enjoy restaurants, coffee shops, movies, live music, and so much more.

POOL COMMUNITY: BUILD YOUR DREAM HOME: 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.

First time on market in almost 50 years. Located on the north end of Gt. Barrington at Belcher Square is this exceptional opportunity. Boasting two curb cuts, one on Rt 7 aka Stockbridge Rd and the other on Rt 23 aka State Rd. This property is ready for new owners. Situated on .47 +/_ acres are two buildings. At 215 State Rd is a post and beam two story barn with one story additions on two sides. Two garage doors for ease of access. There is a 1/2 bath (cold water only). Utilities are town water, town sewer, 200-amp fuses, natural gas hot air furnace. The second building contains three rental units. Upstairs at 8A Stockbridge Rd is a three-room apartment with galley kitchen and full bath. Heat is oil fired hot water. Electric is 200-amp circuit breakers. Main level at 8 Stockbridge Rd

Residential development opportunity! This expansive parcel offers potential for 17 building sites, ideally located just minutes from downtown Great Barrington and Butternut Ski Area. The property abuts the iconic Appalachian Trail, offering tranquil access to nature and recreation. Build a cul-de-sac community where residents can experience the best of the Berkshires--hiking, skiing, and vibrant town life--all just moments away!

Just outside the charming village of Housatonic, this extraordinary Queen Anne Victorian stands as a true architectural gem, nested amid lush gardens and beautifully landscaped grounds. From its distinctive urn shaped columns to its twin towers, gables and wrap around porch, every detail reflects the grace and grandeur of a bygone era - balanced perfectly with thoughtful modern updates. Sweeping lawn with private patio and mature plantings. Currently configured as a two family residence, the layout offers easy conversion back to a magnificent single-family home, making it ideal for a grand Berkshire retreat, full time residence, or multi-generational living. Inside you will find historical character, original millwork & trim, and updated kitchens & baths. Whether you're seeking a stately

Embrace the extraordinary at 395 Park St. North, where history meets opportunity. This stunning red brick 6,833 sq.ft. warehouse, once a bustling trolley barn, boasts high ceilings and a rich industrial charm, with river views while exploring the spacious layout, featuring 3 updated bathrooms, a newer roof and building updates. It has versatile separate offices and garage/shop areas. With ample parking and loading docks, envision endless possibilities from manufacturing to art gallery or more. Conveniently located near dining, parks, and cultural attractions, this property invites you to re-imagine living or workspace with style and creativity. Total acreage and assessment include two lots.

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!

This historic 4-bedroom 3.5-bath home sits on a beautifully landscaped 1-acre lot surrounded by ornamental trees, vibrant flower gardens and mature plantings. Originally built around 1800, this comfortable well-maintained house features high ceilings, warm wood flooring, and plenty of period charm. The main level welcomes you with a spacious living room accented with Greek Revival moldings, an expansive bay window with built-in window seats, and an inviting wood-burning fireplace. Nearby, a charming den offers another wood burning fireplace and quiet spot to relax with a book. Off the living room, the formal dining room can comfortably accommodate a large crowd at holiday gatherings...