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.

Set on 22 private acres, this Monterey retreat offers a peaceful escape from city and suburban life. Freshly painted this spring, it's near Lake Garfield and Monterey Town Beach, and across from Beartown State Forest. The bright, expansive home features four ensuite bedrooms, including a spacious primary suite, large entertaining areas, and cathedral & vaulted ceilings. Outdoors, enjoy a 16' x 40' heated gunite pool, an outdoor enclosed shower, a large stone patio, and the year-round Loom Brook flowing through the woods. The lower level includes a sauna, exercise pool, and utilities. A two-car garage connects to a mudroom with laundry, half bath, and outdoor shower, plus a large bonus room above. A rare opportunity at this price in scenic, convenient Monterey, with fiber internet.

Tucked away at the end of a long driveway and perched atop its own private hill, this stunning 3-bedroom, 2.5-bath post-and-beam home offers complete privacy and breathtaking mountain views. The open floor plan is centered around a dramatic floor-to-ceiling fieldstone wood-burning fireplace, with soaring ceilings, exposed beams, and beautiful pine floors throughout. The primary suite includes a private bath, while two additional vaulted-ceiling bedrooms share a full bath. Enjoy central AC, a metal roof, board-and-batten siding, portable generator hookup, and a large dry basement for storage. Outside, relax on the expansive rear deck, swim in your spring-fed pond, fish on a lazy Sunday afternoon, and enjoy spectacular sunsets and incredible stargazing from your own hilltop retreat.

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!

A Truly Inspired Berkshire Retreat. The perfect home to relax, create, and be inspired, this remarkable Egremont property offers an exceptional blend of luxury, comfort, and creativity--truly unlike anything else on the market. The main residence features three spacious bedrooms and three full baths, enhanced by radiant in-floor heating beneath stunning reclaimed ancient teak floors. The thoughtfully designed first-floor primary suite serves as a private sanctuary, complete with direct access to a personal sauna, hot tub, and greenhouse--an ideal setting for rest and rejuvenation. Outdoors, the property transforms into a private resort. A heated Gunite pool is surrounded by lush, curated gardens, elegant stone patios, a fire pit, and a charming gazebo. A dedicated pickleball court adds

Privately sited across 10.37 park-like acres, this fully updated residence stands as an elevated countryside sanctuary, positioned moments from historic Rhinebeck Village and ten minutes from the Taconic State Parkway. The interiors express a refined architectural warmth, anchored on the main level by a primary suite with full bath, a striking floor-to-ceiling stone fireplace with an integrated wood stove, and a thoughtfully updated chef's kitchen designed around a generous central island. The upper level offers private guest quarters featuring two spacious bedrooms, a full bath, and a dedicated laundry room, while an attached two-car garage affords subtle everyday convenience.

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.

Properties of this magnitude and character are becoming a true rarity in today's market. Brookmede Farm, isn't just a listing; it is a magnificent blank canvas of 22 beautiful scenic acres, defined by sweeping mountain views and a profound sense of quiet serenity. From the moment you arrive, the silence and the scale of the landscape invite you to imagine the unlimited possibilities. Whether you envision a world-class equestrian estate, a sustainable organic farm with cows and chickens, or a sophisticated multi-structure family compound, this land provides the space and the soul to make it a reality. Standing as a centerpiece to this vision is a towering, three-story Timber Frame barn. With its incredible volume and structural presence, it offers a

Four-bedroom homes are a rarity at Coldbrooke, where most residences offer three. This one combines that hard-to-find layout and one of the community's more generous floor plans with a location beside the Miraval Berkshires resort and the historic Wyndhurst estate, putting world-class spa, dining, and golf just steps from the door. Inside, vaulted ceilings and an open layout fill the home with light. A thoughtfully updated kitchen anchors the main level, opening to a spacious great room with adjoining dining and living areas built for gathering. Out back, a screened porch and deck overlook the golf course, an easy setting for summer cookouts or a drink after a round.

A once-in-a-lifetime opportunity to build your dream home on a large waterfront parcel in Lenox. This spectacular 14-acre property offers privacy, tranquility, and direct frontage on beautiful Laurel Lake while remaining just minutes from downtown Lenox, Tanglewood, shopping, dining, and all the Berkshires has to offer. Enter through the stone and metal electric gate, cross the stone bridge, and arrive at a cleared, manicured homesite ready for your custom estate or compound. A scenic boardwalk winds to your private dock and lakeside sitting area. Truly a rare Berkshire offering combining natural beauty, convenience, and waterfront living.

Set on a desirable tree-lined dead-end street in the heart of Lenox, this beautifully restored 1937 Cape blends timeless character with exceptional craftsmanship. Featured in Berkshire Magazine, the 3,740 sq. ft. home offers original heart pine floors, a wood-burning fireplace, and extensive updates including new plumbing, electrical, Pella windows, roof, and central AC. The three-level layout features 3 bedrooms, 4 full baths, two upper-level suites, and a finished lower level with a guest suite, office, and workshop. French doors open to a wraparound veranda overlooking Goshen stone terraces, fruit trees, and a fire pit. Walk to downtown Lenox with convenient sidewalk access, while Tanglewood is just minutes away.

Entertainer's Delight! Tucked away in one of Sandisfield's most scenic settings, this quality-built log home offers over 4,600 sq.ft. of finished living space, plus an additional 2,000+ sq.ft. in the walkout basement ready for living, recreation, or storage. Crafted with exceptional materials, the home features soaring ceilings, expansive gathering spaces, and a warm, inviting atmosphere perfect for entertaining or everyday living. Multiple decks provide an ideal setting to dine, unwind, and enjoy the peaceful natural surroundings. Experience the perfect balance of privacy and convenience, just 20 minutes to Guido's and downtown Great Barrington, 30 minutes to Lenox and Tanglewood, and 15 minutes to Ski Butternut. A true Berkshire gem for year-round living, weekend retreat, or investment!

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.

Classic eyebrow colonial along the Roeliff Jansen Kill w/ renovated barn and large tillable field across the road. The home has been completely redone from the studs out. Exposed beams, vaulted ceilings, radiant heat, central air, new plumbing, new electrical yet so many original details were preserved. Kitchen is open to dining with wood stove and seating area making this the center of the home. Off the entry is the den (with laundry closet) and the living room with french doors to a patio. Upstairs there are three bedrooms, two with en suite baths. The barn is three stories of finished space with central air and heat. Lower level presently a wood shop, main floor is separated into two large studios; high ceilings, natural light. 2nd floor is a large space with full bath and kitchenette.

Exceptional Commercial Investment Opportunity | 5.1 Acres | Multi-Tenant AssetPositioned along a high-visibility corridor on a major highway, this rare 5+ acre commercial offering features five well-maintained buildings with a diverse and fully occupied tenant mix. The property includes a popular restaurant, gift shop, coffee/breakfast cafe, hair salon, lively beer hall, medical office, and a dedicated maintenance building--providing stable, multiple income streams in a single, cohesive investment.The grounds and infrastructure have been meticulously cared for, with recent upgrades including newer septic systems and new boilers, ensuring operational efficiency and long-term reliability.

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

Nestled on just under three beautifully landscaped acres in one of Williamstown's most sought-after neighborhoods, this gracious, sprawling cedar-shingle residence blends classic New England architecture with modern updates and exceptional spaces for everyday living and entertaining. The thoughtfully designed floor plan offers 4 spacious bedrooms and 4.5 bathrooms, including a generous primary suite. Multiple living and gathering spaces include a welcoming family room, a formal living room with crown molding and custom built-ins, an elegant dining room, and a beautifully updated kitchen and bathrooms. Above the attached two-car garage, a private guest suite with a bedroom, full bathroom, and kitchenette provides exceptional flexibility for extended family, guests, or a private home office

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.