Sort:


60 Photos
STONE HOUSE PROPERTIES, LLC
$2,995,000
4 BD | 5 BA
Residential - Single Family

Set on 30 private acres bordering Beartown State Forest, this exceptional Berkshire estate offers a rare combination of timeless farmhouse architecture, refined craftsmanship, and complete privacy. Built in 2018, the 4,700-square-foot residence is thoughtfully designed to blend seamlessly into its surroundings, creating a home that feels both elegant and deeply connected to the landscape. Filled with natural light and beautifully proportioned throughout, the home offers four bedrooms, five bathrooms, and inviting spaces designed for both everyday living and effortless entertaining. At the heart of the home, the chef's kitchen features Vermont Danby marble countertops, a spacious pantry, and an inviting breakfast nook that opens to the surrounding gathering spaces.


36 Photos
STONE HOUSE PROPERTIES, LLC
$749,000
3 BD | 4 BA
Residential - Single Family

Nestled in a magical woodsy setting on a lightly-travelled country road, this uniquely charming home is a standout. Designed and renovated with exceptional taste, enter the front door and you won't want to leave. The open-floorplan living area includes a gourmet kitchen, a gas fireplace, and access to a wide, screened porch overlooking acres of wooded privacy. The hallway off the entry foyer/mudroom leads past the powder room to the cozy primary suite. At the top of the open staircase you'll find a comfortable sitting nook between 2 more bedrooms and a second full bath. The lower level has a large finished room with another gas fireplace & the third full bathroom, perfect for use as a family room or fourth bedroom. There's also large separate storage. Only 10 minutes from the private Otis


53 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$950,000
4 BD | 3 BA
Residential - Single Family

Perfectly poised and priced! This immaculately maintained four-bedroom residence, set on an acre of land, delivers three levels of sophisticated living space designed for both effortless entertaining and quiet sanctuary. The property balances a serene, retreat-like setting with beautiful mountain views and unparalleled convenience to local amenities and top-tier Great Barrington schools. The home is enveloped by a lush and mature landscape, offering a changing tapestry of flowering color and seasonal interest throughout the year. Cross the welcoming mahogany front porch an ideal vignette for morning coffee or evening relaxation into the expansive main level. The heart of the home is an open-concept great room featuring beautiful cherry wood floors, anchored by a warm fireplace, built-in


57 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$724,900
4 BD | 3 BA
Residential - Single Family

One of a kind home, on cul-de-sac in sought after Dalton neighborhood. Custom designed and built by famed architect, Brian Pilling. Quality Built by Allegrone. Distinctive layout with three family rooms one on each level. Sunken living room with dramatic floor to ceiling stone masonry fireplace. Open kitchen remodeled with granite, unique tile and stonework plus professional grade appliances. Lightfilled rooms with balcony overlook to master suite with new luxury bath and loft sitting room-office . Two tier deck private from master suite. Full walkout to expansive and private wooded back yard on just under one acre. Style, space and three levels of expansive living with many updates for a move in ready home in desirable Dalton. Incredible seasonal sunset views. Feel like country in town.


56 Photos
THE KINDERHOOK GROUP
$1,490,000
4 BD | 2 BA
Residential - Single Family

''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage'' Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming 1BR guest cottage, with large living room and mini-splits, is ideal for rental income or private guests. Garages for 5+ cars, perfect pool site, and privacy ensured by abutting protected land.


34 Photos
BURNHAM GOLD REAL ESTATE, LLC
$259,900
6 BD | 3 BA
Multi-Family

Expand your investment portfolio with this well-maintained three-family property in a desirable North Adams location! Each unit offers separate heat, electric, and hot water, providing added convenience for owners and tenants alike. Conveniently located just over the bridge from MASS MoCA and downtown North Adams, residents will enjoy easy access to dining, shopping, entertainment, and local attractions. The property also features off-street parking with one dedicated space per unit. Whether you're an experienced investor or looking to owner-occupy while generating rental income, this is an excellent opportunity to own a solid income-producing property in a sought-after location.


19 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Build your Berkshire dream home on this exceptional parcel offering the rare combination of privacy, distant southwestern views, and deeded access to Big Pond -- one of the Southern Berkshires' hidden gems. The property features a large, level, elevated building site with perc testing already completed and partial clearing in place, making it easy to begin planning your getaway or year-round residence. Just a short distance away, enjoy deeded access to beautiful 330-acre Big Pond, a motorboat lake perfect for swimming, kayaking, fishing, or mooring your boat for summer adventures. Located in the charming town of Otis, you'll enjoy low taxes, town-owned fiber optic broadband with affordable Gig-speed internet, and the unique character of a Berkshire community known for its natura


54 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$795,000
4 BD | 3 BA
Residential - Single Family

At the end of a quiet dead-end road in Sandisfield, this c.1892 four-bedroom farmhouse sits less than twenty feet from the Wild and Scenic West Branch of the Farmington River, a federally protected, free-flowing trout river. Four bedrooms. Two full baths plus a half. 2,516 sq ft. 4.61 acres. Beautifully transformed interior: a granite-island kitchen rebuilt from the ground up, wide softwood floors, working brick fireplace, cast-iron clawfoot tub, first-floor primary opening through French doors to a stone patio, stairs to lawn and river. Kitchen and dining open to a deck over the water. Quarry-granite three-car garage, studio cottage with grandfathered footprint, and a second river parcel with 19th-century mill history included. Flood Zone A12; elevation certificate available. READ MORE


50 Photos
PIRETTI REAL ESTATE
$2,750,000
4 BD | 3 BA
Residential - Single Family

Experience the best of Berkshire living in this stunning contemporary waterfront home on Stockbridge Bowl. Thoughtfully designed, this 4 BR, 3 full bath year 'round home offers a seamless blend of modern comfort and natural beauty! Sunlight pours through expansive windows, framing breathtaking water views from nearly every room. The open concept living space is anchored by a striking double sided fireplace, creating a warm and inviting atmosphere for both every day living and entertaining. The kitchen flows effortlessly into dining and living areas, all oriented to capture the lakefront setting. The deck is the perfect place for dining or simply soaking in your surroundings and a private dock provides direct access for boating or swimming. Your opportunity to own a turnkey retreat!


78 Photos
PIRETTI REAL ESTATE
$2,100,000
5 BD | 4 BA
Residential - Single Family

Iconic Lenox home: very rarely does a home with this historic integrity come on the market...now is your time to continue its legacy . Built in 1915 as one of the focal points of Cliffwood Street, this charming home has been updated for today's life style without sacrificing its significant architectural details. Beautiful common rooms including a dream kitchen with marble counters, formal Dining Room with French doors to the enclosed porch and onto the new deck and acre of land; formal Living Room with fireplace, family room and welcoming foyer off the front porch. The 2nd floor is home to all 5 bedrooms plus an inviting ''summer porch'' off one! Updated baths, kitchen, roof, utilities...and add to that: crown moldings, pocket doors...this home is truly a rare find in today's market


15 Photos
ASHMERE REALTY, INC.
$409,900
4 BD | 2 BA
Residential - Single Family

4 Bedroom 1.5 bath brick cape on over half acre lot, wood floors throughout, fireplace, newly painted, dining room, eat in kitchen, one car attached garage, breezeway, family room in basement. Includes separate 720 square foot ranch with 2 bedrooms, 1 bathroom on property, front porch, vinyl siding, separate utilities


64 Photos
COMPASS MASSACHUSETTS , LLC GB
$1,275,000
4 BD | 4 BA
Residential - Single Family

Special Berkshire retreat on 25 private acres in Harrington Woods with beautiful views. Offering 5,400 sq ft, this 4-bedroom, 4-bath home features oversized rooms and high ceilings. The main level includes a recently renovated chef's kitchen, expansive primary suite with walk-in closets, guest room/office, library with built-ins, dramatic living room and a 400 sq ft screened porch. The walkout lower level offers two additional bedrooms, exercise room, family room, professional pool table, sauna and steam shower. Additional highlights include an oversized 2-car garage with Level 2 EV charger, 12x24 storage shed, and a 30-panel solar array with a transferable utility credit. HOA amenities include tennis, pickleball and a heated seasonal pool. Minutes to Otis Ridge and Great Barrington.


27 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$595,000
3 BD | 2 BA
Residential - Single Family

Tranquil Berkshire Retreat: Cottage with Screened Porch and River Sounds Embrace the ease of single-level living in this enchanting 3-bedroom, 2-full-bath cottage nestled in historic Stockbridge. Perfect as a year-round residence or a peaceful weekend getaway, this home perfectly blends cozy charm with modern convenience.


32 Photos
ALTON & WESTALL REAL ESTATE AGENCY, LLC
$274,900
3 BD | 2 BA
Residential - Single Family

This cherished family home is ready for its next chapter. The first floor offers a functional kitchen featuring a custom-built island with bar seating, a dining room, living room, flexible bedroom or home office, and a convenient half bath with laundry. The second floor features three bedrooms and a full bath. The partially finished basement adds valuable living space with a game room or family room and abundant storage options. Energy-efficient features of this home include seller-owned solar panels, vinyl replacement windows throughout, and a high-efficiency tankless water heater. Step outside to your own private oasis, complete with a fenced yard, newer above-ground pool, hot tub, multiple decks, and landscaping that creates the perfect setting for relaxation and outdoor gatherings.


56 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$979,000
5 BD | 5 BA
Residential - Condo/Townhouse

Sitting right on the Lenox-Lee line, Katydid Cottage is one of the few freestanding homes at Fox Hollow - your own house, your own private patio, with Lenox and Tanglewood just up the road. It feels like a single-family home but comes with the ease of condo ownership, so your weekends go to the lake instead of the upkeep. The main floor is where this one really works. The kitchen is bright and open to a big dining room, and the living room has a gas fireplace for the cold months. The primary suite is on the first floor too, so you can live on one level if you'd prefer.