Berkshire Homes for Sale

Berkshire Homes for Sale

Welcome to Berkshire County, Massachusetts – a picturesque region where natural beauty meets small-town charm. Nestled in the western part of the state, Berkshire County is renowned for its stunning landscapes, rolling hills, and vibrant cultural scene. Whether you're drawn to the breathtaking views of the Berkshires or the rich history that permeates the area, this county offers a unique blend of outdoor adventure and artistic inspiration.

With homes for sale ranging from quaint cottages to sprawling estates, Berkshire County is a haven for anyone looking to invest in real estate. Imagine waking up to the serene sounds of nature, with the majestic mountains as your backdrop. Here, you'll find properties that reflect the character of the region, featuring classic New England architecture and modern amenities. Whether you're seeking a cozy retreat for weekend getaways or a permanent residence to enjoy year-round, Berkshire County has something for everyone.

The local community is vibrant and welcoming, with charming towns like Lenox, Stockbridge, and Great Barrington, each offering their own unique flavor of life. Enjoy world-class dining, boutique shopping, and a plethora of outdoor activities, from hiking and skiing to art galleries and music festivals. The Berkshires are not just a place to live; they are a lifestyle choice that embraces the beauty of nature and the warmth of community.

Explore the homes for sale in Berkshire County today and discover your dream home in this enchanting part of Massachusetts. Your new adventure awaits!

Newest Berkshire Homes for Sale

$589,000
3 Beds ⋅ 1 Baths ⋅ 73556884 MLS
Escape to your own island retreat where each day is a peaceful, waterfront sojourn. Nestled on an island in Big Pond, this tranquil waterfront property offers extraordinary privacy, natural beauty and modern comfort. Thoughtfully updated, the home features a masterfully renovated kitchen and bath, a first-floor bedroom and distinctive architectural details including cedar shakes, that create warmth and character throughout. All furnishings to stay. Mornings of seasonal birdsong and the delicate beauty of the new day invite ease and comfort both on the screened, full-windowed porch or on the two outdoor decks. Breathtaking views of the lake encourage leisurely relaxation while winding garden paths and natural stone walls enhance the property’s timeless appeal. A large boathouse provides exceptional storage for all your recreational equipment and includes a clothes dryer and refrigerator for added convenience. If you enjoy sailing, paddling or simply exploring the water, the property’s sailboat, canoe, kayaks and motorboat allow you to embrace an active and energetic lifestyle on this 330-acre lake. Tension and stress melt away as you cross the water to your own secluded oasis. Here you’ll discover enduring serenity, stunning scenery and stimulating outdoor activities where privacy and nature surround you. Tanglewood, world-class art museums and theatre, shopping, dining and everyday conveniences remain within easy reach in Otis and the nearby Berkshire hills.

18 Big Pond, Otis

Listing courtesy of Listing Agent: Mary O'Connell from Listing Office: Wolcott Realty.
$2,295,000
5 Beds ⋅ 6 Baths ⋅ 73557267 MLS
A long private drive opens to a contemporary Berkshire estate set across nearly 20 acres in Richmond. More than 4,800 square feet unfold with an easy, connected flow, from the light-filled cathedral entry to generous rooms made for gathering. The home offers five bedrooms, 5.5 baths and two fireplaces, plus a flexible guest or extended-family wing with a separate entrance and plumbing for a future kitchen. An elevator, central air, attached 3-car garage and whole-house generator bring ease to everyday living. Outside, a beautifully landscaped in-ground pool is framed by broad lawns and mature woods, with abundant space for dining, lounging and long summer afternoons. A path leads into the acreage and toward the mountain beyond. Set apart from the house, a heated recreation building with an indoor pickleball court, flexible recreation space, seasonal water and half bath adds an exceptional dimension to this private Richmond retreat.

421 Swamp Rd, Richmond

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.
$275,000
5 Beds ⋅ 2 Baths ⋅ 73555056 MLS
This home has been well loved by the same family since 1960. In 1967 a large addition was built to expand the space. Today, there are 3 main floor bedrooms and a main floor bath with laundry. Or use one of the main bedrooms as a formal dining room! 2 bedrooms upstairs with a half bath make this a very spacious home. There is also an expanded attic space over the addition. Rounding this space out are a front porch and a back porch! A large partially fenced yard is perfect for outdoor enjoyment!This home is ready for it's new people... Anyone can move in today and slowly update as desired! The roof was done in 2012. The boiler was new in 2009 - new sewer pipe sleeve in 2008. Windows were also done circa 2009

93 Pine St, Dalton

Listing courtesy of Listing Agent: Kolleen E. Schmitt from Listing Office: Keller Williams Realty.
$289,000
3 Beds ⋅ 2 Baths ⋅ 73554906 MLS
Set on private acres in the Berkshires, this one-owner manufactured home, built in 2005, offers the perfect combination of privacy, space, and opportunity. The home features 3 bedrooms and 2 full bathrooms, including a spacious primary suite with a private bath complete with a soaking tub and separate walk-in shower. The functional layout offers comfortable living spaces, while a walk-up attic provides valuable storage. Served by a 420ft drilled well and with a passed Title 5 inspection, this property offers added value and peace of mind. Situated on a slab foundation, enjoy your morning coffee or unwind in the evening from the front porch overlooking the property. Outside, you'll also find an exterior storage shed and a concrete pad with electricity already in place!

9 South County Rd, Florida

Listing courtesy of Listing Agent: Patricia Molina from Listing Office: Century 21 North East.
$599,000
2 Beds ⋅ 1 Baths ⋅ 73553901 MLS
Deadline for Highest & Best Offers Mon. 7/27 @ 5:00PM! Welcome to your summer escape on one of the Berkshires' most quintessential lakes. This architect-redesigned cottage blends classic New England charm with thoughtful, modern updates- the result is a home that feels both timeless and completely turn-key. Step inside to an open floor plan bathed in natural light & water views where the updated kitchen and bath bring clean lines and modern finishes without losing the warmth of a true lake cottage. The living space opens up to the new composite deck built for summer evening gatherings & morning coffee. Set on a perfect stretch of shoreline, this is the magical summer cottage you've been waiting for: still water in the morning, swimming and paddling in the afternoon, and stars overhead at night. A private dock offers easy mooring for your boat.The property comes fully furnished and includes kayaks and a canoe, so all you need to bring is yourself — the water is calling, and there's still time to make this summer yours! Come visit one of the Open Houses, this Sat 7/25 11-1 or Sun 7/26 1-3!

279 Old Pond Rd, Becket

Listing courtesy of Listing Agent: Sarah Shipman from Listing Office: 5 College REALTORS® Northampton.
$699,900
4 Beds ⋅ 3 Baths ⋅ 73553438 MLS
Enjoy comfort, space, and privacy in this custom 8-room post and beam home set on 25.3 scenic acres. The property features 2½ bathrooms, Bruce hardwood floors, first-floor laundry, and a spacious living room with high ceilings and a pellet fireplace. The partially finished basement adds living space with a family room, wood-burning fireplace, and bar area. An oversized two-car garage provides added convenience and storage above. Outside, you’ll find a15x26 in-ground pool with pavilion, 3 storage sheds, a 24’ x 20’ barn, a large rear wooden deck, and a front Trex deck. The acreage offers excellent privacy and plenty of room for recreation, gardening, animals, equipment storage, or hobby farming. Whether you’re looking for a peaceful country retreat or a property with room to grow, this estate offers a rare opportunity to own acreage, outbuildings, a pool, and generous living space.

200 Peru Rd, Windsor

Listing courtesy of Listing Agent: Zahi Haddad from Listing Office: Zee Haddad Realty.
$1,795,000
4 Beds ⋅ 8 Baths ⋅ 73552517 MLS
MAGNIFICENT circa 1913 ESTATE with CARRIAGE HOUSE. Rare opportunity to own a distinguished Berkshire 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. See the Stone House Properties web site for further details.

1 and 5 Park Ave, Dalton

Listing courtesy of Listing Agent: Jeff Wilkinson from Listing Office: Jeff Wilkinson.
$325,000
2 Beds ⋅ 1 Baths ⋅ 73549506 MLS
Darling, adorable, a simply must see. Charming craftsman style ranch, boasts 2 bedrooms plus the sunroom has heat pump heat / AC providing more opportunity for additional living space (a 3rd bedroom?, space for washer & dryer? ~ you decide).Living room features wood floors, bay window, fireplace with dentil molding, spacious dining, and kitchen with newer appliances. This single level living home is situated on an approximately 1/3 acre spacious back yard and has mature landscaping, shed & 1 car garage.Large ticket items recently done: Roof is 5 yrs old +/- on house, and shed & garage are 2+/- years old. Electrical upgrade 2025. Weatherization 2024. Water heater 2025. Furnace 2025 by BCAC. Easy to show. Agents - use ShowingTime.

26 Windsor Ave, Pittsfield

Listing courtesy of Listing Agent: Nadine Hiser from Listing Office: KRG - Key Realty Group.
$2,698,000
5 Beds ⋅ 5 Baths ⋅ 73551597 MLS
Some homes are purchased. Others become part of a family's legacy. Welcome to 109 Under Mountain Road. There is something unmistakably special about a Berkshire summer- evening stroll to Tanglewood, morning coffee overlooking protected meadows, or relaxing on the patio as the music of the Boston Symphony Orchestra drifts softly through the evening air. Bathed in extraordinary natural light, this architect-designed home embraces its breathtaking setting with soaring walls of glass, vaulted ceilings, exposed beams, skylights, and exquisite gardens. Thoughtfully designed for gracious entertaining and comfortable everyday living, the spacious first-floor primary suite allows you to enjoy the home with ease for years to come, while family and friends gather in beautifully appointed guest rooms.

109 Under Mountain Rd, Lenox

Listing courtesy of Listing Agent: Maureen White Kirkby from Listing Office: Berkshire Hathaway Home Services Barnbrook Realty.
$249,900
3 Beds ⋅ 1 Baths ⋅ 73551312 MLS
This recently renovated cape sits on a double lot, offering almost a half acre of land, since the sale includes an adjacent lot on Oak Ave. There are gleaming hardwood floors in bedrooms, living room and dining room.The layout is amazing! The 1st floor offers a bedroom, beautiful bathroom, kitchen with quartz countertops and new appliances, and the living room & dining room both with windows overlooking beautiful city and mountain views, which you can also admire from your deck. The 2nd floor features 2 additional bedrooms. The walkout basement offers great storage space. There is plenty of parking & a driveway on the back. City water & sewer, updated 200 amp electric service and vinyl siding complete this great home. Located within walking distance to many restaurants and other downtown attractions, including MassMoca, and approx a 5 min drive to MCLA!

335 State St, North Adams

Listing courtesy of Listing Agent: Maria Liccardi from Listing Office: Kempf-Vanderburgh Realty Consultants, Inc..
$499,999
4 Beds ⋅ 3 Baths ⋅ 73550281 MLS
Turnkey Sandisfield RentalCurrently used as an income-producing rental, 125 Town Hill Rd offers consistent cash flow with strong potential for future owner occupancy or a weekend retreat. Set on a quiet country road surrounded by woods, the property delivers the privacy with your own tennis court in your backyard and a spacious screened-in porch. Inside features a comfortable, functional layout with bright living spaces and a welcoming feel. Ideal for investors, second-home buyers, or those planning ahead to occupy. Convenient access to nearby towns, outdoor recreation, and all the Berkshires have to offer. A versatile property with both income and lifestyle upside--don't miss it!

125 Town Hill Rd, Sandisfield

Listing courtesy of Listing Agent: Maureen White Kirkby from Listing Office: Berkshire Hathaway Home Services Barnbrook Realty.
$1,750,000
6 Beds ⋅ 5 Baths ⋅ 73550137 MLS
Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. a state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling.

500 Williams, Pittsfield

Listing courtesy of Listing Agent: Maureen White Kirkby from Listing Office: Berkshire Hathaway Home Services Barnbrook Realty.
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