Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The thoughtfully appointed, updated kitchen flows seamlessly into a generous living area anchored by custom built-ins and a cozy wood-burning fireplace. Wall-to-wall windows grace the formal dining room, ensuring every meal is accompanied by breathtaking scenery. Both the living and dining rooms offer direct access to a sprawling rear deck, perfect for entertaining.

Uncommonly Superb View -- A Vermont Meadow Retreat Tucked quietly into a broad meadow and surrounded by lush Vermont landscape, this property enjoys one of those rare, completely unspoiled western vistas: a full, harmonious sweep of the Taconic Mountain ridgeline, framed perfectly within human scale. The almost 40 acre setting--meadow bordered by deep woodland--creates a sense of arrival, privacy, and permanence that is difficult to replicate. The architect designed home blends natural materials inside and out, offering a calming, organic environment that feels inseparable from the land around it. One of the sellers' guiding goals the architect skillfully interpreted, was harmony with the landscape, expressed most beautifully in the roofline: ... (see more)

Fabulous historic church. Located in the Stockbridge hamlet of Interlaken. Quiet and exclusive neighborhood just off Rt.183. Stylishly decorated by a renowned architect and designer. High ceilings, huge windows, and mahogany fittings. Beautifully restored kitchen with many original details. Marble topped sink/counter. Walk through to the magnificent living area to step back in time to an earlier era. Then on to the nave to enjoy soaring ceilings, oversized windows and room for entertaining. Enjoy this 'party space.' Or use for an artist studio, recording studio or any pastime that needs space. Minutes to Berkshire Botanical Garden, Tanglewood and the center of Historic Stockbridge.

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio

An excellent opportunity to blend immediate cash flow with long term upside in a desirable and growing area! An added advantage of this exciting property is its potential for short-term rental income, subject to local ordinances! Rare opportunity to acquire two apartment buildings totaling nine units in a convenient Adams location. These properties are thoughtfully updated throughout, with a newer roof, boilers, hot water, windows, electrical systems, and modern finishes. Kitchens are remodeled with stylish touches, including quartz countertops, newer cabinetry, and updated appliances. with stylish touches including marble countertops, new cabinetry, and updated appliances.

Magical Egremont setting. Step into timeless charm with the comfort and craftsmanship of a beautifully renovated 1860 home abutting Karner Brook. The brook flows just beyond the sitting room and deck overlooking the beautiful landscaping and bridge that leads to the garden and brand-new outbuilding. Offering three/four bedrooms, three bathrooms, and over 3,000 square feet, this distinctive property blends historic character with thoughtful modern upgrades, including cherry cabinetry, granite countertops, a Sub-Zero refrigerator, Viking six-burner range and hood, and two dishwashers. Wide-plank pine floors, beautiful woodworking, and a fireplace create inviting spaces throughout.

Originally a gift from Williams College President Harry A. Garfield, the son of United States President James Garfield, to his daughter, this elegant and gracious South Street home is available for the first time in over thirty years. Fine architectural details abound with beautiful crown moldings and woodwork, six panel doors, gleaming oak flooring, abundant built-in shelving and cabinetry, and large, light-filled floor-to-ceiling windows. The spacious entrance hall opens on your left to a stunning wood-paneled library lined with ample book-shelving and warmed by a corner fireplace with wood mantel and slate hearth. Ahead, the lovely living room, with another handsome fireplace with decorative mantel, side pilasters and marble hearth, provides access to a covered slate side terrace.

Exceptional Federal style reproduction farmhouse located in a peaceful setting on a scenic country road. Offering 3-4 bedrooms, 3.5 bathrooms, beautiful hardwood and marble floors. The kitchen with Viking range, custom cherry cabinets, granite countertops and walk-in pantry opens to a family room with a brick Rumford fireplace. The formal dining room opens into the living room. There are French doors to a heated sunroom that connects to a barn/garage with 2nd floor great room and full bathroom. The grounds include a bluestone patio and Goshen steps to the home. Property setting has mature landscaping and perennial gardens. Adjacent undeveloped 2.5 acre lot included.

Nestled in a peaceful, wooded setting, this exceptional home offers the perfect blend of comfort, style, and natural beauty. Sunlight fills the open floor plan through expansive windows, creating bright, inviting living spaces and showcasing scenic views year-round. A soaring stone fireplace anchors the great room, while beautiful hardwood floors flow throughout. Enjoy the screened porch, accessible from both the great room and the first-floor primary suite, for quiet mornings or relaxing evenings. The main level also features a spacious primary suite and convenient first-floor laundry. Upstairs, a generous loft provides flexible living space, along with three additional bedrooms and two full baths, including one en suite. . . . .

Excellent 8-Unit Investment Opportunity-5 minute walk to the Lake! Clean, well-maintained multifamily property featuring 8 total units with separate utilities. Each unit includes central A/C. Property offers private, dedicated parking for tenants. Prime location—just minutes from major hospitals, large employers, shopping, and public transit. High-demand rental area with strong occupancy history. Ideal for investors seeking turnkey income with upside potential. Great long-term hold in a desirable neighborhood.

Easy living Ranch home on beautiful Onota Lake. Fantastic views of the Lake and Distant Berkshire Hills. Enjoy westerly sunset views from your expansive, manicured lawn and almost every room in the house. A quiet setting with comparable homes and easy access to all the Berkshires has to offer. Needs a little TLC, but well worth it for this sought after location and lifestyle. Hardwood floors refinished and interior recently painted.

Attention Investors! Excellent 6-unit investment opportunity in Lee with strong existing income and flexible rental potential. Five of the six units have been renovated with premium finishes, complemented by a newer roof, updated electrical and newer heating systems--helping reduce near-term maintenance and capital needs. Currently operated with a mix of long-term and seasonal rentals, the property offers flexibility for traditional leasing, short-term rental use, or a combination of both. The spacious 4BR/2BA unit also provides an attractive owner-occupancy option while generating income from the remaining units. Public water and sewer, separate utilities, ample parking and convenient access to the Mass Pike, Lee Outlets and Berkshire attractions. Easy to show- come see for yourself!

Cross the charming historic-style covered bridge and enter a world of privacy, nature, and endless possibilities. This remarkable 94-acre sportsman's estate offers river frontage on the Farmington River, expansive woods, trails, and room to roam. At the heart of it all is a spacious split-level home with 3 bedrooms and 2.5 baths, featuring fresh paint, new flooring, and a new roof. A 5-bay barn/garage provides incredible space for vehicles, equipment, hobbies, and toys. A separate mobile home offers flexible additional space for a studio, guest quarters, office, or creative retreat. Whether you're seeking a private Berkshire escape, outdoor adventure, or simply a place where the woods are truly your own, 132 North Main Road is a rare opportunity to own your very own Hundred Acre Wood!

Step into history at 1001 Canaan Southfield Rd, a rare 1797 Colonial estate set on over 23 breathtaking acres of mature, landscaped grounds. This extraordinary property features two serene ponds with fountains, over 300 feet of classic stone walls, and the scenic Umpachene River winding through the land. Extensive landscaping, stone patios, and picturesque outdoor spaces create a private retreat unlike any other. The home offers 4 bedrooms, including a spacious primary suite, blending timeless character with natural beauty. Included are three separate parcels, with an additional lot located across the street, offering endless possibilities for expansion, recreation, or investment. A truly one-of-a-kind Berkshire property rich in history, charm, and unmatched natural surroundings.

Discover a rare lakefront opportunity on Otis Reservoir with amenities seldom found in one property. Combined with the lower lot, enjoy 62 feet of direct waterfront, a grandfathered boathouse with electricity and electric lift, waterfront bathhouse with living room, heated garage, dedicated hot tub room with fireplace, and lake views from nearly every room. Perfect for entertaining with an updated kitchen, multiple living areas, separate driveways, ample parking, and two storage sheds. Remodeled in 2021 with new heating and cooling, on-demand hot water, quartz island, stacked cabinetry, stainless appliances, and gas range. Walk-out basement. Sold fully furnished and ready to enjoy.

Experience upscale, maintenance-free living in desirable Devon Meadows, ideally located near Lenox and Stockbridge and just 5 minutes from Tanglewood and the many cultural and outdoor attractions of the Berkshires. This spacious luxury condominium features an open floor plan perfect for everyday living and entertaining. The first floor offers a primary bedroom suite, laundry, and a versatile fifth bedroom ideal for an office or den. Upstairs are three spacious bedrooms, two full baths, and a comfortable family room. Enjoy the privacy of a peaceful country setting with the convenience of being minutes from dining, recreation, shopping, and all that the Berkshires has to offer.

Experience upscale, maintenance-free living in desirable Devon Meadows, ideally located near Lenox and Stockbridge and just 5 minutes from Tanglewood and the many cultural and outdoor attractions of the Berkshires. This spacious luxury features an open floor plan perfect for everyday living and entertaining. The first floor offers a primary bedroom suite, laundry, and a versatile fifth bedroom ideal for an office or den. Upstairs are three spacious bedrooms, two full baths, and a comfortable family room. Enjoy the privacy of a peaceful country setting with the convenience of being minutes from dining, recreation, shopping, and all that the Berkshires has to offer.

CONTEMPORARY FARMHOUSE! Sited on a knoll dotted with old apples trees overlooking scenic views all framed by a meandering fence. All you could ask for is in this well-built home, offering a first floor primary ensuite, library with fieldstone fireplace, A well appointed kitchen opens to both the dining and a living room with fireplace. A screen porch, 1/2 bath, laundry room/mudroom leading to a 2 car garage completes the first floor. The second floor offers 3 addition bedrooms, full bath, built-in bookcase with window seat. Kick back and relax on the front porch! A fabulous Berkshire house close to all Berkshire cultural venues, skiing, shopping, restaurants and, just plain fun!

Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes -one a four bedroom home and a 1000 sq ft guest house-both 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. Spacious garage allows room for cars, hobbies and workshop, perfect pool site, and privacy ensured by abutting protected land. Generator for both houses.Access to town beach. A generous seller credit opportunity toward buyer's preferred improvements upon acceptable offer. Online psf is in error. Actual is $469 psf

Custom built contemporary home on over 2 acres, 5 minutes to Great Barrington center. Large open first floor with vaulted ceilings and lovely gathering space. Kitchen is dreamy w/large island, coffee bar, ample storage and tons of working space. Open to dining area as well as the living room with propane fireplace. Large screened in porch flanks the east side of the home expanding the footprint 3 seasons a year. A mud room entry off the garage with laundry, two offices and a powder room complete this floor. Upstairs there are two guest rooms with en suite baths and a primary suite with fireplace and large bathroom. The LL offers an add'l 1900 sq ft (not included) with a game room, gym, guest bedroom, media and full bath. Truly turn key w/ sunset views over the neighboring private airport.