Berkshire Homes for Sale

Welcome to Berkshire County, Massachusetts – a picturesque haven nestled in the western part of the state, where stunning natural beauty meets vibrant community life. Known for its breathtaking landscapes, including the majestic Berkshire Mountains and serene lakes, this region offers a unique blend of outdoor adventure and cultural richness. Whether you’re hiking the Appalachian Trail, skiing at one of the local resorts, or enjoying the summer music festivals, Berkshire County is a year-round destination for nature lovers and art enthusiasts alike.

The charm of Berkshire County extends to its diverse real estate market, where homes for sale cater to a variety of lifestyles and budgets. From quaint cottages tucked away in wooded enclaves to luxurious estates with sprawling views, there’s something for everyone in this enchanting region. Imagine waking up to the sound of birds chirping and the sight of vibrant fall foliage right outside your window!

As you explore the homes for sale in Berkshire County, you'll discover properties that not only offer comfort and style but also a sense of community. Many neighborhoods boast excellent schools, friendly neighbors, and local amenities that make everyday life a pleasure. Whether you’re looking for a weekend retreat or a permanent residence, Berkshire County’s real estate options are sure to inspire.

Join us in discovering the beauty of Berkshire County, where your dream home awaits amidst the stunning backdrop of nature and culture. Don’t miss the opportunity to make this captivating region your own!

Newest Berkshire Homes for Sale

$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

$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

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.