Berkshire County Real Estate

Welcome to Berkshire County, Connecticut, a hidden gem that perfectly blends the charm of small-town living with the vibrancy of nature and community spirit. Nestled in the northwest corner of the state, Berkshire County boasts stunning landscapes, rich history, and an array of recreational opportunities that make it a desirable destination for families, retirees, and outdoor enthusiasts alike.

With its rolling hills, lush forests, and picturesque lakes, Berkshire County is a haven for those who appreciate the great outdoors. Whether you’re hiking along scenic trails, fishing in tranquil waters, or enjoying a leisurely picnic in one of the many parks, the natural beauty of this region is truly captivating. In the winter months, residents and visitors can indulge in skiing and snowboarding at nearby resorts, making it a year-round playground for adventure seekers.

The county is also steeped in history, with charming towns that offer a glimpse into Connecticut’s rich past. From the historic architecture of Great Barrington to the quaint shops and local eateries in Stockbridge, each town has its own unique character and story to tell. Community events, farmers' markets, and art festivals bring residents together, fostering a strong sense of belonging and camaraderie.

Education is a priority here, with highly-rated schools and access to esteemed higher education institutions, making Berkshire County an ideal place to raise a family. Whether you’re looking for a cozy cottage, a spacious family home, or a luxurious retreat, the real estate options in this area cater to a variety of tastes and budgets.

Explore the beauty and charm of Berkshire County, CT, where every day feels like a breath of fresh air, and discover your perfect home in this enchanting corner of New England.

Newest Listings in Berkshire County

$1,795,000

4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24193129 MLS

MAGNIFICENT circa 1913 ESTATE with CARRIAGE HOUSE Rare opportunity to own a distinguished estate featuring two residences on more than six private acres. The stately main home at 1 Park Avenue showcases exceptional craftsmanship, a grand foyer with sweeping staircase, expansive kitchen with butler's pantry, formal living spaces, sun porch, and multiple covered porches. The luxurious primary suite offers a sitting room, balcony, sun porch, and spa-like bath. Three additional bedrooms, office, and finished third floor provide ample living space. The charming carriage house at 5 Park Avenue features 4 bedrooms and flexible accommodations for guests, extended family, caretakers, home office, or income potential. Attached 2-car garage, mature grounds, and exceptional privacy complete this remarkable estate.

1 And 5 Park Ave, Dalton

$2,950,000

7 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24171893 MLS

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and equestrian excellence. Spanning 27.3+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence/Inn, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility. The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The main house/inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations. For the serious equestrian, the estate offers multiple barns and paddocks. Training is a year-round luxury thanks to the 6,000 sqft heated indoor arena, which includes an owner's apartment and viewing area - and a professional grade outdoor ring. Enjoy all the area attractions including Tanglewood, the Mount, MASS MoCa and breathtaking hiking trails.

802 State Rd, Richmond

$7,250,000

6 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24151033 MLS

A rare French Manor estate on one of the most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook-creating a secluded retreat that feels worlds away, yet remains moments from the cultural heart of the Berkshires. It is awaiting buyers final finishes. At the center of the estate stands a newly built main residence inspired by the grand proportions of the Gilded Age, featuring soaring 19-foot ceilings and impeccable architectural presence. Thoughtfully constructed by a highly regarded local craftsman, the home showcases state-of-the-art mechanical systems, including geothermal heating and cooling, blending classic elegance with modern efficiency. Approaching completion, the residence presents a rare opportunity for the next owner to personalize select finishes and make this remarkable home truly their own. A short stroll west leads to a beautifully converted barn guest house, carefully relocated to the property and transformed into a dramatic open-concept retreat. Soaring ceilings, antique beams, and expansive windows frame the estate's sweeping mountain and pond views, creating an inviting space for guests, artists, or quiet reflection.

209 Blue Hill Rd, Great Barrington

$3,998,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24142076 MLS

WHERE THE WORLD FALLS AWAY 227 acres. 227 years. At East Hill Road's summit, East Hill Farm is a fully realized estate where infrastructure, land, and possibility are complete and in place. The 1798 Thomas Shepard House-museum-quality restoration featuring 5 bedrooms, 5.5 baths, 5 fireplaces, original King's board floors, hand-blown glass windows-awaits your vision for kitchens and baths. Modern additions: radiant heat, elevator, sun-filled library, luminous sunroom overlooking formal gardens and 4-acre spring-fed pond. The 227 acres aren't just land-they're composition. Meadow unfolding to pond positioned where morning & evening light catch it. Mature forest giving way to unbroken views. Trails looping you gently home by blue hour. Stone walls, pool, tennis court, greenhouse. Magnificent 3,550sf hand-hewn barn moved here. Northern land borders State Forest; southern abuts conservation land-permanent privacy. Guest house (6,668sf): 4 residences replete with possibilities-multigenerational living, art studios, writing spaces, media rooms, yoga, creative sanctuary. Cathedral ceilings, fireplaces, soaring light. The quiet money cannot buy: depth of silence settling at dusk, Milky Way stretching clear across valley, no light pollution. Architecture, land, and sky speaking the same language. Where hosting feels like breathing, completely natural. 5 families in 227 years. You'll be 5th. 5 min to dining, 20 min to Great Barrington, 2.5 hrs to Boston/NYC. Complete and irrepla

764 E Hill Rd, New Marlborough

$110,000

ACTIVE Status ⋅ 24113956 MLS

Set along A rural country Town road, this parcel is a mixture of lightly wooded flat ground adjacent to/with a bog which is home to a mixture of frogs, a heron or two and other 'seasonal' visitors. Of the 7.2+- acres (the parcels total size) approximately 2.5 acres is a mostly flat zone in within which a home could be located. While approved for same back around the turn of tis century, all permits are expired and must be re-applied for to build 'today. The neighborhood consists of mixed-use lots ranging between mostly residential, and a few small businesses. REGARDING THE PICTURES: Many are when the land was cleared for building some years ago; currently it has become overgrown and lightly wooded. An underground electric line (not live) is installed underground to a post(pictured), for hooking into any structure needing electric when built. Any uncleared pictures show land in its current condition as you read this. Proper footwear and clothes are recommended for inspection. Especially in foliated months. The area is near Sheffield, Gt. Barrington, Canaan, CT., as well as ski areas (Butternut and Catamount), hiking trails, fishing rivers, the Arts, and others that exist throughout the Berkshires.

730 Clayton Rd Rd, Sheffield

$5,650,000

11 Beds ⋅ 10 Baths ⋅ ACTIVE Status ⋅ 24013888 MLS

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of the future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands The Tullar House; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique Dutch Gambrel dating back to 1761, reported to be the 2nd oldest house in Egremont. Retaining much of its original charm and detail, this historic jewel boasts ample-sized rooms for gatherings and entertaining, a renovated chef's kitchen, a formal dining room, 3 grand fireplaces, 2 primary suites, and plenty of room for guests. Enjoy sweeping views of the grounds from the porch laid with locally sourced marble or relish in the shade of 'The Champion', a 250+-year-old Black Walnut Tree standing as the oldest in the state and serving as a living testament to Tullar Farms' rich past. The exterior is a sight to behold with ornate and symbolic details that capture the attention of all who pass by.

25 Sheffield Rd, Egremont

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