A rare opportunity to own two lots totaling 10.6 acres in sought-after West Stockbridge. Accessed by a shared driveway, the parcels offer flexibility for a private compound or two thoughtfully sited homes. Mowed walking paths wind through groves of mature trees and the partially cleared landscape, creating a peaceful setting with a natural balance of privacy and usable space. The property benefits from excellent southern exposure, well-suited for passive solar design and improved energy efficiency. Preliminary plans for a single home are available to help bring your vision to life. Ideally located just minutes from Tanglewood and close to downtown Lenox and West Stockbridge.

NEAT AND CLEAN MID-CENTURY RANCH ON A PRETTY COUNTRY ROAD. Lovely pastoral and distant mountain views. 3 bedrooms, 1.5 baths. Living room with gas fireplace. Kitchen open to the dining area. Original built-ins. Large screened porch and deck to enjoy the VIEW. Clean basement with high ceilings. One car garage.

Welcome to 5 Pomeroy St. in the heart of charming West Stockbridge, where small-town New England character meets the beauty of the Berkshires. Ideally located just moments from local shops, galleries, restaurants, and cultural attractions; this property offers convenient access to Tanglewood, hiking trails, skiing, and year-round recreation. Enjoy a peaceful setting with easy access to major routes, making weekend getaways or everyday living equally appealing. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this property offers exceptional potential in one of Berkshire County's most desirable communities. Don't miss the opportunity to own a home in this sought-after location.

Here's a rare opportunity to own a classic roadside motel with strong potential in a popular small-town tourist destination. This 17-room property, complete with an on-site owner's quarters, offers a solid option for renovation or rebranding or to convert to housing. The motel has been operating for many years and continues to welcome repeat travelers, but it would benefit from fresh energy and cosmetic updates to reach its full potential. With steady local tourism and limited lodging competition, there's plenty of room to grow revenue through improved marketing, refreshed rooms, and updated amenities. Located near shops, restaurants, and popular area attractions such as Tanglewood, Edith Wharton House, Norman Rockwell Museum, and many others.

This charming New England farmhouse is located in the heart of West Stockbridge Village. You'll feel right at home in this updated, open-floor-plan, 3 bedroom, two bath home featuring beautiful hardwood floors throughout. The modern kitchen with newer appliances, butcher block island, and breakfast bar is perfect for entertaining as well as enjoying quiet home-cooked meals. Relax on your spacious seasonal front porch and back deck as additional living spaces. Gather around the new propane fueled fireplace in the living area for a cozy evening during chilly days. The end of driveway sidewalk leads you to local shops, restaurants, entertainment and the Williams River/Shaker Mill Pond - just a just a block away.

Don't miss this rare opportunity to own this private, meticulously maintained waterfront sanctuary. The grounds feature a charming English garden, an expansive deck and a private dock for launching kayaks, offering outdoor living at its best. The main level features an eat-in kitchen with custom cabinetry, a living room, sunroom ideal for gatherings, an office, mudroom with laundry and a first-floor primary suite with full bath, providing convenient single-level living. This home includes central AC and a backup generator for year round comfort and peace of mind. With beautiful views and just moments from downtown, this property blends privacy, comfort and convenience in a truly special setting.

Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.Can also be purchased as part of a investment portfolio 13 Park Street Stockbridge, MA MLS#249532

Prime Commercial Property in the center of downtown West Stockbridge (see VIDEO). Over 4,200 square feet on Main Floor with office/storage on the second floor. Currently used as several Galleries and a large Workshop. Town Water & Sewer plus a private Parking Lot offers the possibility of expansion, re-creation, possibilities and profitability.Ideal for Restaurant, Marketplace, Retail, Professional Office, Live/Work or Gallery. Minutes from the MA Turnpike (I-90), NY State line, Tanglewood and all Berkshire attractions. Owner retiring and priced to sell.

Nestled in the heart of West Stockbridge, this stunning 5-bedroom, 5.5-bath Federal/Greek Revival style home at 4 Stockbridge Road combines historic charm with modern luxury. Built in 1825, the residence has been beautifully renovated, maintaining its classic character while offering contemporary amenities. The spacious interior features generous living areas, perfect for family gatherings and entertaining. Outside, you'll find a large barn, a greenhouse and impeccable gardens ideal for gardening enthusiasts or creative projects. This property is not just a home; it's an opportunity to enjoy the tranquil beauty of West Stockbridge, with its vibrant community and picturesque surroundings. Located minutes from many local attractions including Tanglewood and minutes from the highway.

Welcome to 3 Cone Hill in the heart of the Berkshires. This rustic retreat is the epitome of a classic country compound that's been lovingly cared for and enjoyed by the same family for many years. Minutes to Tanglewood, this 2+ acre lot hold more fun and relaxation than most large estates. Sitting over Cone Brook, you'll enjoy listening to the babbling water from your screened-in gazebo. After playing a game of tennis or pickle ball, take a soak in the hot tub before guests come, which will be plenty as you can easily sleep 14 people. The house has 5 BR/3BA with an open concept on the main level. The detached garage has 1 BR/1 BA guests quarters where they can come and go as they please. Let the lasting memories begin today!

Set across 30+ pristine Berkshire acres, this property offers sweeping westerly mountain views, gently rolling fields, and Cone Brook running the length of the land to Shaker Mill Pond. With approximately 2,000 feet of frontage on Swamp Road, the possibilities are wide open: farming, equestrian use, a private estate, or potential subdivision into 6+ buildable lots.Two substantial barns, both equipped with electric and water, are already in place, offering immediate utility and flexibility. The setting is both scenic and convenient & just minutes to the village of West Stockbridge. A short drive to Tanglewood and Lenox, and within easy reach of ski areas.Additionally, a 1950s four-bedroom, two-bath home with a heated basement sits along the road frontage, ready for

Nestled in a peaceful, wooded setting, this exceptional home offers the perfect blend of comfort, style, and natural beauty. Sunlight fills the open floor plan through expansive windows, creating bright, inviting living spaces and showcasing scenic views year-round. A soaring stone fireplace anchors the great room, while beautiful hardwood floors flow throughout. Enjoy the screened porch, accessible from both the great room and the first-floor primary suite, for quiet mornings or relaxing evenings. The main level also features a spacious primary suite and convenient first-floor laundry. Upstairs, a generous loft provides flexible living space, along with three additional bedrooms and two full baths, including one en suite. . . . .

Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully designed to meet the needs of modern living. These units feature elegant wood floors and come equipped with all necessary appliances, including dishwashers and in-unit laundry facilities. Central air conditioning ensures comfort year-round, while tiled double-sink bathrooms add a touch of luxury. Ample storage space is available in each unit, allowing residents to keep their living areas tidy.

A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. There's an impressive architect-designed guest house with 2 ensuite bedrooms, balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place for rentals, or hosting family and friends both winter and summer.The main house is 3-4 bed, 2 1/2 bath, views of Tom Ball mountain, the property is a combination of gardens, fields, forest, and offers several outdoor living spaces, including a stone patio off the kitchen. A short jaunt to No. Six Depot, The Foundry performing arts, and Tanglewood. Central to Gt. Barrington, Lenox and Stockbridge for theatres, boutiques, skiing, golfing, museums and so much more at your fingertips

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant heat throughout the main

Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace below. Guided by museum-quality principles, long stretches of UV-protected wall space give way to precisely framed vistas. Board-formed concrete walls mitigate winter winds, while the exterior is clad in enduring, low-maintenance Vermont slate. Embracing sustainable luxury, the three-bedroom, two-study home features triple-glazed windows, super-insulated envelopes, and geothermal climate control.