Berkshire County Real Estate

Berkshire County Real Estate

Welcome to Berkshire County, Massachusetts – a hidden gem nestled in the heart of the picturesque Berkshires. Known for its stunning natural beauty, vibrant arts scene, and rich history, this enchanting region offers a unique blend of rural charm and cultural sophistication, making it an ideal place to call home.

Berkshire County is renowned for its breathtaking landscapes, featuring rolling hills, lush forests, and tranquil lakes. Outdoor enthusiasts will revel in the endless opportunities for hiking, skiing, and water sports. The county boasts several state parks, including the famous Mount Greylock State Reservation, which is home to the highest peak in Massachusetts, offering panoramic views that are nothing short of spectacular.

Culturally, the Berkshires are a treasure trove of artistic expression. The region is home to the renowned Tanglewood Music Center, where the Boston Symphony Orchestra performs each summer, as well as a plethora of galleries, theaters, and museums. The Norman Rockwell Museum, located in Stockbridge, celebrates the iconic American artist's work, capturing the essence of small-town life.

In addition to its natural beauty and cultural offerings, Berkshire County features charming towns and communities, each with its own unique character. From the historic streets of Lenox to the vibrant downtown of Great Barrington, residents enjoy a strong sense of community and a slower pace of life, all while being just a short drive from urban conveniences.

Whether you're seeking a serene retreat or an active lifestyle filled with cultural experiences, Berkshire County is the perfect place to find your dream home. Discover the magic of the Berkshires and embrace a lifestyle that balances tranquility with inspiration.

Newest Listings in Berkshire County

$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.
$325,000
6 Beds ⋅ 4 Baths ⋅ 73557707 MLS
Don't miss this recently renovated two-family property in a desirable location close to downtown! Each spacious unit offers 3 bedrooms and 1.5 bathrooms, featuring updated kitchens and baths, beautifully refinished hardwood floors, and functional layouts. Whether you're looking to expand your investment portfolio or owner-occupy while generating rental income, this property checks all the boxes. Conveniently located near shopping, dining, schools, and local amenities, this is an excellent opportunity in a sought-after neighborhood.

34-36 Crandall St, Adams

Listing courtesy of Listing Agent: Michele Purcell from Listing Office: Lamacchia Realty, Inc..
$20,000
73557592 MLS
Explore the possibilities with this parcel located on Shuttlecock in the desirable Sherwood Greens community of Becket. Enjoy access to beautiful Long Bow Lake, where residents can take advantage of swimming, kayaking, canoeing, fishing, and the private beach. Conveniently located near Jacob's Pillow, Tanglewood, hiking trails, skiing, golf, and the many recreational and cultural attractions the Berkshires have to offer, this property provides an opportunity to own land in a peaceful, amenity-rich setting.Parcel ID: 213-68.30Buyer and buyer's agent to perform all due diligence regarding property boundaries, zoning, permitted uses, utilities, access, and any potential future use of the property. Property is being sold AS IS, WHERE IS, with no representations or warranties, express or implied. Seller and listing agent make no representations or warranties regarding the property.

0/6 Shuttle Cock Dr, Becket

Listing courtesy of Listing Agent: Jessica Rebello from Listing Office: Remax Revolution.
$870,000
3 Beds ⋅ 2 Baths ⋅ 73557264 MLS ⋅ ['Oronoque'] BLDG.
One of only eight freestanding Oronoque Villas, this 3-bedroom, 2-bath condominium offers 1,773 square feet of beautifully proportioned one-level living on the historic grounds of one of Stockbridge’s great Berkshire cottages. Originally the model residence for the Villas, the home features hardwood floors, handsome millwork, built-ins, a wood-burning fireplace, and an easy, inviting layout designed for both everyday living and relaxed entertaining. The kitchen and dining area form the heart of the home, while the heated enclosed porch opens to views of the private garden. Dine on the deck beneath mature trees, unwind in the hot tub, or spend summer afternoons beside Oronoque’s heated pool and tennis court. An attached garage and whole-house generator add year-round comfort and convenience. Minutes from Stockbridge village, Lenox, Tanglewood, Naumkeag, the Norman Rockwell Museum, hiking, skiing, dining, and the Berkshires’ celebrated cultural attractions, this is a rare Stockbridge villa to enjoy in every season.

11 Prospect Hill Unit 8, Stockbridge

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.
$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.
$1,200,000
73556496 MLS
Own a part of history..."Blue Stone Manor". Available for the first time in over twenty years. Create your own 'one of a kind' estate on a piece of the land houses the "Gilded Age Tudor" mansion that is associated with McKim, Mead & White. West Sheffield Road is one of Great Barrington's most picturesque country Road. Offering a quintessential Berskhires landscape of rolling meadows, mature woodland and sweeping mountain vistas. Enjoy privacy and yet all the conveniences of walking to acclaimed restaurants, cultural attractions, and the heart of Great Barrington. Easy access to Tanglewood, Butternut Mountain and the Appalachian Trail. This 3.69 acres is ready for a new steward with 300' of frontage on West Sheffield Road.

Lot 2 West Sheffield Road, Great Barrington

Listing courtesy of Listing Agent: Shelly Tretter Lynch from Listing Office: Kinlin Grover Compass.
$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.
$419,000
8 Beds ⋅ 4 Baths ⋅ 73554619 MLS
Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA.. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size of 4160 square feet provides a significant footprint within the urban landscape. We invite you to discover the potential and unique character of this Pittsfield address. Three Units are vacant and recently remodeled with market rents averaging about 1395.00 in the area. One Unit is rented month to month at 950.00. All units are lead certified.

53.5 Orchard St, Pittsfield

Listing courtesy of Listing Agent: David Houser from Listing Office: Houser Metro Realty.
$375,000
6 Beds ⋅ 3 Baths ⋅ 73554585 MLS
Turnkey 3-unit multifamily investment in Pittsfield, just minutes from downtown. 100% occupied, generating $4,173/month ($50,076/year) in gross rent from all-current tenants. Unit mix: 98A (1BR/1BA) at $1,199/mo, 98B (2BR/1BA) at $1,324/mo, and 100 (3BR/2BA) at $1,650/mo. All three units have gas heat and hot water; owner covers snow removal, landscaping, and water & sewer. 2025 operating expenses: taxes $3,102.87, insurance $3,168, electric $365.34, water & sewer $2,265.48. Priced at just $102/SF — well below nearby comparable sales at 91 Dalton Ave ($114.50/SF) and 1 Rostone Pl ($119.50/SF). A stable, cash-flowing asset with strong relative value in a growing rental market. Buyer to do Due Diligence.

98 Lincoln St, Pittsfield

Listing courtesy of Listing Agent: Jason Saphire from Listing Office: www.HomeZu.com.
$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.
$129,900
73553500 MLS
Come enjoy the outskirts of Great Barrington just 1 mile off of Rte23/7 intersection, this 7 acre lot on a dead end private way. Just off of Route 23 this land abuts a Commonly owned lot of the East Mountain Estates community adding a buffer between you and Route 23 also a view of a pond. Watch the area wildlife come to the pond while enjoying the outdoors on your future deck/patio area you are going to build. There is a downslope from the road but level when you get to the main portion of the lot. Drive would be cut in along the slope to have a more gentle access. Utilities are underground, HOA fees will apply to help with maintenance of the roadway and common areas.

5 East Mountain Rd, Great Barrington

Listing courtesy of Listing Agent: Susan Como from Listing Office: Buy Rite Home.
Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.