Cleared and mowed building lot with attractive views, conveniently located just minutes from West Stockbridge Village. Enjoy easy access to local restaurants, cafés, shops, galleries, cultural attractions, and outdoor recreation, while being close to all that the Berkshires have to offer. A wonderful opportunity to build your Berkshire retreat in a peaceful yet convenient setting.

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.

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.

Just the right size, this lovely contemporary home captures the ease and beauty of Berkshire living, with beautiful westerly views and a sunny, open-sky setting. A stone's throw from the charming village of West Stockbridge and just minutes from downtown Lenox and Tanglewood, the location offers an ideal blend of country living, culture, and convenience. Inside, three bedrooms and two baths complement an inviting open floor plan anchored by a dramatic floor-to-ceiling fieldstone fireplace. The kitchen and dining areas flow naturally into the living space, while a cozy den and lovely screened porch offer additional places to relax and enjoy the surroundings. A large deck, detached garage and storage shed complete the property. Effortless and inviting, this is the perfect Berkshire getaway.

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.

Classic 1860 New England farmhouse located in the historic enclave of Williamsville. Carefully renovated with meticulous attention to detail, this home blends timeless character with modern comforts. The light-filled eat-in kitchen features a Viking range, center island, quartz countertops and backsplash, and a newer refrigerator and dishwasher. A striking timber-frame family room addition showcases a cathedral ceiling, pine floors, and a new pellet stove, with access to a bluestone patio surrounded by beautiful perennial gardens and a designated fire pit area. The dining room features a wood-burning fireplace and opens to the sunny formal living room, currently used as a billiard room but easily adapted to suit your needs.

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.

Drive in beneath the trees and the house appears in a pool of sunlight, set well back from a quiet road with gardens, lawn and woods gathered around it. There is an immediate sense of having arrived somewhere apart. Private and peaceful, yet not isolated, this one-owner West Stockbridge home has the easy spirit of a modern farmhouse and a distinctly relaxed way of living--a place to slow down and settle in. An inviting front porch, screened by the surrounding landscape, is private enough to become a place of its own--for morning coffee, reading or the pleasure of doing very little.

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

Extraordinary, Inside and Out. This stylish log home on 3+ acres is the complete Berkshire retreat. Recently updated and improved, the home pairs modern lodge character with resort-like amenities. A heated saltwater gunite pool and integrated hot tub anchor the beautifully landscaped grounds. A locust fence encloses the pool area, with bluestone patio, lush lawn, and a stunning renovated pool house designed for entertaining, dining, or remote work. Inside, the home is warm, open, and full of character, with the added benefit of true one-level living. The great room is the centerpiece, with soaring ceilings, exposed log beams, and a substantial stone fireplace.

Now offered at a new compelling price! 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.

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.