SUCCESSFUL CHOCOLATE SHOP BUSINESS FOR SALE in a prime location on Main Street in Stockbridge. Business for sale only, with all display cases, fixtures, furniture, and inventory included. Serving chocolates, gelato, teas, cocoa, and other sweets since 2015, this long-established business has been a favorite of visitors and locals alike for many years. This ideally located and successful chocolate shop takes advantage of the built-in high foot traffic, as tourists and locals visit The Red Lion Inn and other Stockbridge cultural venues. If you've ever dreamed of owning your own chocolate or sweets shop in a quaint yet thriving New England town, this business opportunity is for you!

This Historic Carriage House located on an old estate in the center of Stockbridge awaits your renovation as Unit #10 on this unique condominium property. Walk down the driveway and you are right in town or sit in the backyard and be away from it all. The building is being sold ''as is.'' Easements, the fees for the connection of residential utilities, a Wetlands delineation report and all Town of Stockbridge permits and their costs for this single residential unit are the responsibility of the Buyer. A closing date that anticipates ample time for all permitting and approvals to be completed can be scheduled after the signing of the Purchase and Sale Agreement. Come see this lovely property and use your imagination to envision your future home in this beautiful old New England town.

PRIME BERKSHIRE LAND - FEEL 'AWAY FROM IT ALL' YET YOU ARE MOMENTS FROM THE BEST OF THE BERKSHIRES. $158,000+ UNDER ASSESSED VALUESet on a serene & forested country road, this location makes the perfect retreat - yet you are in the heart of the Berkshires just minutes to Stockbridge & Lenox, Tanglewood, The Bowl, The Mount, Kripalu, Great Barrington, the Pike, shopping & more. The single home site & septic area are already cleared, wetlands approvals are in place, and rough-in driveway cut in.This 7.8 acre parcel offers peace & quiet, beauty, and low Stockbridge taxes. With an assessed value of $397,600 this land offers a tremendous value for those looking to build on PRIME Berkshire land. This is so close to 'ready to go' - plan your design, drill a well, and finish permit!

This 2-acre property just .4 mi. from the center of Lenox is an opportunity of a lifetime to build your Berkshire dream luxury/lifestyle home. This historical property was the site for the home of Jonathan Hinsdale-first European inhabitant in the town of Lenox (1750). Adjacent to Shakespeare & Company Campus and just minutes from Tanglewood and all the local attractions. Town water/sewer/electric on Old Stockbridge Road.

Beautiful 25 Acres in Stockbridge. Stockbridge Bowl, Tanglewood, the villages of Stockbridge, Lenox, and Housatonic are all nearby. The property consists of two separate building lots - the south lot with 12.56 acres, and the north lot with 12.66 acres. Potential for mountain views from both lots with some clearing. At the top of the driveway of the north lot is a large flat area that offers several different building site opportunities. The south lot is a bit steeper with a small flat section at the end of the driveway for a potential building site. Many possibilities - build on the north lot and keep the south lot for extra acreage, an additional dwelling to use as a guest house or to sell off in the future. Great opportunity in Stockbridge.

Heron Pond Condominiums in Stockbridge (at intersection of Wallace Rd. and 26 East St.) is adjacent to the village and the Red Lion Inn. Famous for having been the former Shaggy Dog Recording Studio, that was a location for prominent musicians of the 60's and 70's. Come experience the beauty of the four seasons in the center of the Berkshires. Enjoy 1-level living, 1-bed, 1-bath condo with lots of storage space, a fully applianced kitchen. Washer and Dryer included. The grounds offer plenty of green manicured lawns, a pond and walking trails throughout. A skip to Berkshire Theatre, close to Great Barrington, Tanglewood in Lenox, and most Berkshire cultural amenities.

Beautiful first floor condo that has been rehabbed. This beautiful Knoll Condominium is walk to town in a beautiful lovely setting. Lots of natural light in this unit and it so charming , Laundry room and storage area in the building, Perfect location if you like to walk to the Red Lion Inn and downtown. Close to all the Berkshire attractions. No Pets

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Welcome to Heron Pond Condominiums in charming Stockbridge, where comfort meets convenience in a tranquil setting. This beautiful condominium offers an ideal combination of spacious living and cozy charm, featuring 2 or 3 bedrooms and 2 full baths. The screened porch is ideal to relax and enjoy nature without the bugs, a serene space to unwind, whether you're enjoying morning coffee or evening breezes. The flexible floor plan allows you to choose between 2 or 3 bedrooms to best fit your needs - perfect for guests, an office, or extra sleeping space. Two stylish full bathrooms ensure everyone has plenty of space and comfort. Nestled in Stockbridge, you'll have easy access to all the charm and amenities the area has to offer, with nature at your doorstep. Offered fully furnished.

Welcome to this lovely village home in the desirable town of West Stockbridge. Super location; walkable to Six Depot for coffee, The Foundry for theater, and Ella Mae's for ice cream-just a few of the benefits of living in town. In addition, just a quick drive to Tanglewood and Norman Rockwell Museum. Meticulously maintained with newer windows throughout and offering a perfect blend of charm and comfort. Cheerful kitchen w/ breakfast area and nicely sized gathering rooms. Also a laundry and 1/2 bath on the first floor. Upstairs you will find three spacious bedrooms and a full bath with bathtub. The yard offers lush greenery and there is a large deck off the kitchen- perfect for outdoor grilling & dining. Attached shed for garden supplies. Great curb appeal & move right in.

Incredible land in Stockbridge available for the first time in over 120 years. Build your dream home here in a private setting yet very close to the Norman Rockwell Museum, Berkshire Botanical Gardens and under 3 miles to the historical downtown Stockbridge! Trails, the original chimney and fireplace from the 1800's homestead along with the old trees and gently sloping topography make this unique property a must see. Currently in Chapter 61 for tax benefits. Call today for your appointment!

The best of village living. A gracious in-town colonial with spacious rooms, high ceilings, wood floors and an abundance of natural light. Delightful first and second floor back porches overlooking the lovely backyard with walking bridge over a gentle brook and the winter views of Lenox Mt. Restaurants, shops, recreational and cultural venues are just a short walk down the street. Only 4 miles over the hill to Tanglewood. Should you need more space, there is a partially finished walkout lower level and a walk-up attic with high ceilings and large windows.

Discover an exceptional commercial property on a thriving main thoroughfare in Great Barrington's heart. Formerly a bustling confectionary, this vacant 3,592 sq ft building is a blank canvas for your successful business venture. Its highly visible location with significant traffic, near popular shopping destinations, ensures your business will achieve maximum exposure. The spacious interior provides ample room for retail, office space, a restaurant, or other service-oriented businesses. Key features include existing commercial-grade infrastructure (utilizable or adaptable), public utilities, and convenient off-street parking. Bring your vision to this prime spot and become a cornerstone of the vibrant Great Barrington business community!

Some of the best views the Berkshires have to offer. One of the ''Great Estates'' conversions, Winden Hill condos are in Stockbridge, but within 1.5 miles of downtown Lenox and a short drive to Tanglewood. Located in the Smith building - this unit features 2 bedrooms each with private bath. Easy entertaining in the great room with fireplace and vaulted ceiling. French door leads to the spacious deck. Den/office with half bath serves as bonus third sleeping space. Natural gas heat, central a/c, charging station for your electric vehicle. Very short walk to the community pool, tennis/pickleball.

Charming 1930s Retreat with Water Views and Historic Charm - 170 Stockbridge Road, Lee MANestled just five minutes from both Stockbridge and the village of Lee, this beautifully restored 1930s gem offers the best of Berkshire living. Located near world-class cultural destinations--including Tanglewood, The Norman Rockwell Museum, and Jacob's Pillow--this home sits on a desirable lot overlooking the serene Willow Brook.Inside, you'll find a warm and inviting living room, three generously sized bedrooms, and an open-concept kitchen and dining area ideal for gatherings. The character of the era remains intact, with thoughtful updates that blend old-world charm with modern convenience.An attached barn house adds to the property's appeal and offers exciting potential for creative

Large parcel of land centrally located on a quiet road in Stockbridge. Minutes to the town centers of Stockbridge, Lenox, and West Stockbridge, as well as Tanglewood, Kripalu, the Norman Rockwell Museum, and the Berkshire Botanical Gardens. It is also walking-distance to the Stockbridge Bowl outlet and the Berkshire Art Center.The land is mostly wooded, level, and dry with some open areas. Town water and sewer are on the street. It is an exceptional estate property but could potentially be subdivided in various ways.

This meticulously renovated antique cottage is nestled in a picturesque, private setting along the banks of Kampoosa Brook in the sought-after area of Stockbridge. With thoughtful attention to detail throughout, this charming home beautifully blends historic character with modern conveniences, making it a delightful surprise for contemporary living.Inside, you'll find several cozy spots to relax by the fire, enjoy views of the garden, and listen to the soothing sounds of the brook. Features like exposed beam ceilings, an original oversized fireplace, and wide floorboards pay homage to the home's rich history. The unique layout offers two potential guest/ in-law suites, each with its own entrance for added privacy. The beautifully landscaped yard creates a serene secret garden,

Beautifully renovated & meticulously maintained New England Farmhouse in Stockbridge. Offering a comfortable layout, this beautiful home seamlessly blends modern updates while maintaining a classic country charm. A coveted mudroom entry leads to a gorgeous kitchen with custom cabinetry, stainless appliances, sliders to the patio, and a wood stove for ambiance. Also on the main level are a full bathroom, fantastic laundry room, a spacious LR with fireplace, office/tv room & an elegant paneled DR. On the second floor are 3 bedrooms, including an ensuite primary with balcony & whirlpool tub and a guest bathroom. Gorgeous property w/ stone walls, mature gardens, and old growth trees offering shade and a beautiful landscape. Adjacent 3000 sq.ft barn w/ more land available.

LIGHT-FILLED CONTEMPORARY CAPE on a premier road in the historic Interlaken section of Stockbridge. The open-concept first floor includes a living area with a wood-burning fireplace, dining area with a glass door leading to a large deck, and a recently remodeled kitchen. A half bath and a primary bedroom suite with a full bath complete the first floor. Upstairs, is a second primary suite with a full bath and two guest bedrooms which share a full bath. A two car garage leads to a full, clean basement. The house is in MINT CONDITION and has central air conditioning. There are professionally landscaped gardens with groomed pathways, and a lovely stone patio. Stockbridge residents enjoy access to a private beach on Stockbridge Bowl. A terrific location just 6 minutes from Tanglewood.

Stunning Circa 1850's renovated with seven bedrooms and nine full baths. Classic Greek Revival with strong lines and lovingly preserved details; three period fireplaces, generous gourmet eat-in cook's kitchen and the comfort and style of today's living in the perfect location just a short drive to Tanglewood and in between Stockbridge and Lenox!! This property offers gracious common spaces and six en-suite guest bedrooms. New first floor guest suite with separate entrance.