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.

Beautiful lot located on a highly desirable street. Less than a mile from the town beach at Stockbridge Bowl ! Town sewer available on the street. Plenty of land to build your dream home and still have space for walking trails and ample acreage to enjoy all that nature has to offer.

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!

Property is being sold in AS IS condition. Charming 1850s Two-Family Home on a Quiet Dead-End Street - A Rare Berkshire Opportunity! Nestled in a peaceful Housatonic neighborhood, this historic fixer-upper offers incredible potential for homeowners and investors alike. Built in the 1850s, it's ideal for those seeking a homestead, rental income, or private retreat. Set on a quiet lot with room to garden, farm, or expand, this property features a sunny front porch, an original outhouse, and a garden shed. Enjoy peaceful surroundings while being just minutes from Housatonic village and Stockbridge Center. With multi-family potential, live in one unit while renting the other or create a spacious single residence. A rare find in the Berkshires--schedule your showing today!

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.

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.

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.

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!

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.

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 Stockbridge Colonial has it all....location, separate guest suite and plenty of country chic design. This historic home boasts all the charm of yesteryear with fabulous wide pine floors, state of the art country kitchen that retains it's charm, formal dining room with fireplace, gracious banister to the second floor of guest bedrooms with renovated bath all while seamlessly blending with the open Great room for today's lifestyle living; a fabulous main floor primary bedroom with a wall of closets and an en suite renovated bath. From the spacious decking of the main house there is a romantic covered walkway that leads to separate guest quarters with a Great room, bedroom, bath and kitchenette that has it's own private outdoor gathering space with firepit. The two car oversized garage

THE BERKSHIRE HOUSE YOU'VE BEEN LOOKING FOR IS NOW AVAILABLE!!! This Contemporary is minutes from Tanglewood and the Village of Lenox, private on 6+ acres overlooking Lily Pond and has deeded rights to a private beach on Stockbridge Bowl! An open Great Room of living/dining/kitchen with fireplace and a double volume wall of windows maximizes the view from every vantage and direct access to a fantastic screened porch along with a study/den/office w/fireplace and a primary en suite all on the main level makes this offering almost perfect. Two guest bedrooms, full bath and an open loft family room on the upper level complete this very special offering. Come view this wonderful Contemporary in it's most special and convenient location!

Nestled just north of Stockbridge, MA, this elegantly expanded brick Federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) Originally built in the 1830s, the Carter Estate has been artfully expanded and renovated and boasts over 5,400sf of light-filled, luxurious living space, ideal for those seeking a private yet gracious lifestyle.As you enter through classic stone walls and manicured hedgerows, you'll be welcomed by sweeping meadows and lush gardens. Time slows as you meander along stone pathways that lead to a charming red barn and a quaint stone summer cottage--perfect for painting or relaxing. The estate is oriented towards cultural and natural beauty with walking trails

Unbelievable transformation. You won't want to miss this opportunity. Stunning interior decorating for this Historic General Williams House circa 1795 Lovingly restored and improved with 6 inviting bedrooms, 5.5 updated bathrooms, 6 gorgeous woodburning fireplaces, two full kitchens.: Historic General Williams House circa 1795. This exquisite home has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio Sparkling newer inground pool for your summer pleasure. All this and close to downtown Stockbridge, Norman Rockwell Museum, Tanglewood and all the cultural activities

One of the Berkshires' finest residences, basking in the idyllic mountain scenery. Designed and crafted to meticulous standards, this distinguished 6.2 acre compound is surrounded by captivating, protected vistas far and wide. In the enduring tradition of the regions iconic estates, this extraordinary residence is a place for life to the fullest, providing an endless source of enjoyment in exquisite indoor /outdoor spaces. Fine millwork and 9 fireplaces underscore the comfortably elegant environment. Lower-level entertainment (media)room, wine cellar, fitness studio. elevator, computerized systems. 9,339 SF with 5 bedrooms,6 full/3half baths. Wraparound tiered terraces feature pool with pool house. Glorious terraced gardens and formal gardens with fountain. Separate 3 bedroom guest house