Millerton Classified Ad Listings

5 Magnolia St. Charming In-Town Cape on a Spacious Lot with Inground Pool. Located in a delightful neighborhood close to town. This inviting home built in 1951 offers 5 bedrooms and 2 full baths. Inside, the residence seamlessly balances ample room to spread out with warm, light-filled spaces tailored for everyday living and entertaining. Timeless architectural details throughout bring characte...

200 Sharon Mountain Rd. Effortless elegance on seven acres directly across from protected conservation land. A dappled willow hedge and a classic pea stone driveway lead to this fully reimagined four-bedroom, three-and-a-half-bath retreat. Interiors are by Ellsworth Home, the New York and New England design studio behind the 2024 renovation - featured recently in Litchfield Magazine. Classic mo...

3 Lake Buel Rd. Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered cl...

226 Grove St. Duplex in the hills of Housatonic. Three bedroom, one bathroom on each side. Enclosed front porches and open back porches, large garage, all on a corner lot. Located on the Grove St turn overlooking the village of Housatonic and only a few short steps from the Flag Rock conservation area, this is both in town and in a lovely mountain setting. Both units have large walk-up attic an...

70 Gay St. Welcome to 70 Gay St! Just minutes from Sharon's town center, this 1947, two-story charmer exudes peaceful and sun-filled vibes! Well sited on a beautiful, large 3.8-acre lot with equal parts wildflowers and lawn, the home is nicely nestled among mature trees, with just the right balance of sun and shade. And if you're an investor or developer, this property affords an excellent subd...

18 Butternut Dr. Tucked away on an peaceful cul-de-sac off Lake Buel Road, this spacious, well-built, multi-level 3 bedroom, 2 full-bath home is priced approximately $200,000 below its current assessment, which supplies more than enough room for the interior renovation it needs and deserves. Originally built in 1997 and surrounded by 2.65 acres of wooded privacy, it was thoughtfully designed wi...

8 Equestrian Dr. Here's your chance to enjoy Woodridge Lake living in this spacious, unfurnished three-bedroom home set on a private, wooded 2.5-acre lot. The home features vaulted ceilings, three bedrooms, and an additional first-floor room ideal for a home office. Renters have access to Woodridge Lake and the clubhouse offering tennis, pickle-ball, boating, beach, and pool. Conveniently locat...

153 State Rd. Neat as a pin cape walking distance to downtown Great Barrington and amenities, this home has been thoughtfully renovated top to bottom. This sweet property, also zoned commercially, has 4 bedrooms, a full bath, and even a partially finished basement. The kitchen, complete with a large pantry, retains the charming mid century details, while appealing to the modern aesthetic. Outsi...

77 Paxton Ct. Experience the pinnacle of modern elegance in this sun-soaked new construction masterpiece, privately positioned at the end of a quiet cul-de-sac in the prestigious Woodridge Lake community just two hours from NYC. Unlike most homes in the community, this location offers a rare combination: serene seclusion with a babbling brook audible from the back deck, yet just minutes from ev...

48 Old Middle St Unit 1. Experience the ultimate in Litchfield Hills living with this gorgeous, fully furnished rental at 48 Old Middle Street, Unit 1, in Goshen, CT. Steeped in historic pedigree, this impressive residence built in 1800 beautifully showcases classic architectural details, including stunning wide-board flooring, original exposed beams, and a cozy fireplace. Offering 2,088 square...

32 Calkinstown Rd. Enchanting circa-1850 cedar-shingled cottage tucked into a lush, beautifully landscaped setting along one of Sharon's picturesque country roads. Surrounded by mature specimen trees, layered perennial gardens, stone walls and pathways, and a meandering brook, the property offers a wonderful sense of privacy and the feeling of a secluded garden retreat. Inside, the home is warm...

360 W Side Rd. Meticulously renovated less than five years ago, this breathtaking waterfront home is absolute perfection. Nestled on 1.19 professionally landscaped acres, the property is thoughtfully designed to maximize its stunning natural setting. Upon entering, your gaze is immediately drawn through the open floor plan to a dramatic wall of windows framing panoramic water views. A striking ...

27 Morey Rd. Set along a quiet, dead-end road in the Ellsworth section of Sharon, this newly constructed shed-roof home was designed for simple, efficient living with a strong connection to the Earth. Solar panels and a heat pump system keep utility costs remarkably low, while expansive windows capture natural light and western sunset views. Thoughtful details include Bosch appliances, copper l...

860 Hunns Lake Rd. Peaceful, private 3 bedroom, 3 bath home set in the woods on a mountaintop with a 3/4 deck surrounding the back where you can relax and watch the hawks soar. The inside has an open plan anchored by a double sided fire place that blazes in both the kitchen and living area. Access to the deck is through either the living room for entertaining or kitchen area for grilling. Downs...

Lake Buel Rd. Beautiful level lot with woods and meadow. Mountain views. Minutes to downtown Great Barrington and Butternut Ski Basin. Perced. See attached documents. Build your dream retreat in the Berkshires!

392-394 Park St. Rare, renovated Berkshire investment compound on 0.59 acres in walkable Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic ho...

110 Geer Mountain Rd. FURNISHED RENTAL AVAILABLE for October 2026@$6,500k/month. Modern Country home filled with stylish designer furniture and art. Fabulous AAA South Kent location with expansive lawn and western exposures. 4-5 bedrooms, fabulous outdoor entertainment areas, pond and brook. Close to Lake Waramaug, Appalachian Trail, Mohawk Mtn skiing, Kent and New Preston. Not far from NYC met...

651 Hayes Hill Rd. OFFERED FULLY FURNISHED AND TURNKEY. Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by ...

497 Cornwall Bridge Rd. YOUR PRIVATE RETREAT AWAITS - RENOVATED, MOVE-IN READY and COMPLETE WITH AN ABOVE GROUND POOL! Welcome to this beautifully renovated 3 bedroom, 2.5 bath home offering the perfect combination of modern updates, comfort, and outdoor living. From the moment you arrive, you'll appreciate the fresh new siding and the attention given to updating this property throughout. Step ...

102 Westwoods Rd Unit 1. November-May, $4,500/month. Uber Stylish Furnished 4 Bed/3.5 Bath Cabin. Quiet and Private Setting Tucked Back from Low-Traveled Town Road. Open Floor Plan with Fireplace and Vaulted Ceiling. 1st Floor Primary Suite with Luxurious Bath. Upstairs En Suite First Class Bedroom Plus 2 Others with Shared Bath. Wonderful, Large Screened-in Porch. 3 Min to Village; 12 Min to M...