Prime investment opportunity! This five-unit property features a desirable mix of four, one-bedroom apartments & one, two-bedroom. All units have their own separate heating & electrical systems! Convenient location ensures high demand due to proximity to stores and the hospital. On-site parking. Detached garage/workshop could be rented separately for additional income or used as storage for tenants.

In the heart of historic downtown Lenox, 85 Church Street presents an exciting opportunity to own a versatile two-family property in one of the Berkshires' most desirable villages. Zoned commercial and delivered vacant, the property offers an unusual degree of flexibility for an owner-occupant, investor, or buyer seeking income-producing potential in the center of Lenox. The property features two two-bedroom, one-bath units, each with natural wood details and its own separate natural gas heating system. Both units are equipped with a refrigerator, dishwasher, and range. Refreshed bathrooms, some replacement windows, and a second-floor rear landing/mudroom add to the comfort and functionality.

Elegance Meets History on 1 Eaton Lane! Tucked away on a quiet, sought-after street just minutes from the Country Club of Pittsfield & only 10 minutes to vibrant downtown Lenox, this remarkable Colonial seamlessly blends timeless character with extraordinary versatility. Offering just under 5,000 square feet of living space, this historic estate presents a rare opportunity for those seeking a home with a story. The main house is a masterclass in classic architecture, featuring period details enhanced by thoughtful modern updates. High ceilings, gleaming hardwood floors, & charming front & back staircases ground the home in history, while the spacious layout provides endless room to breathe. The heart of the home is a sophisticated kitchen, featuring rich cherry cabinetry, new SS appliance

Beautiful property in a bucolic setting with sprawling front flower gardens! The main floor boasts a first floor primary with en suite bath, open kitchen with fireplace, dining room with built ins and access to the oversized deck, great room with beautiful wood floors and doors that lead to the serene screened porch, cozy den with fireplace, office/flex space and half bath. The second level includes two guest bedrooms and a full bath with washer and dryer. Truly a special offering.

Welcome to your private retreat in the Crystal Pond community, set on just over 2 acres of beautifully wooded privacy. This 4-bedroom, 3.5-bath residence blends refined comfort with natural serenity, offering a true Berkshire escape. Soaring cathedral ceilings, skylights, and expansive windows fill the home with natural light, highlighting rich wood plank flooring and a warm, elevated design throughout. The main living area features a fireplace, while a separate den is enhanced by a wood stove insert that provides efficient, comfortable heat and a cozy atmosphere. The thoughtfully designed layout includes generously sized bedrooms, including a second-floor bedroom with a private loft space, ideal for a reading nook, office, or creative retreat. Two upstairs bedrooms each enjoy access to

Welcome to 12 Mountain St, a quintessential colonial masterpiece that blends classic elegance with modern functionality. Spanning over three expansive, light-filled floors, this stunning home offers five spacious bedrooms and 3.5 bathrooms, providing the ideal layout for those who love to entertain. The chef's kitchen is designed to inspire with high-end finishes, including a vast center island, a professional-grade Six-burner gas stove w/pot filler, chic quartz countertops. With an abundance of cabinetry and a dedicated, organized pantry featuring custom built-ins, this kitchen is as practical as it is beautiful. Gleaming hardwood floors flow throughout the main level, creating a seamless, inviting atmosphere. Ascend to the second floor, where you will find a tranquil primary en suite wit

Charming, beautifully maintained, and ideally located, this gorgeous Four Square home sits directly across the street from the Mohawk Trail Multi-Use Path and is at the base of the Pine Cobble Trail System, offering an exceptional combination of classic character and outdoor adventure right outside your door. The home features 4 bedrooms and 1.5 baths, beautiful wood floors, and a finished attic that provides additional flexible living, office, or recreational space. A stunning wraparound front porch welcomes you home and offers the perfect spot to enjoy your morning coffee or gather with friends and family. The cozy back deck overlooks a fenced in back yard for those pet lovers and provides even more outdoor living space. Both the front porch and back deck are crafted from beautiful,

The original Tryon Hotel - circa 1840 has the charm of age with the palette of a modern residence. The entry is off the front porch, perfect for mornings basking in the sun and evenings watching the life around. Porch comes into the kitchen area with good working space and open to the dining room with gas fireplace. Large back living room with mini-split gives generous square footage to the first floor. The front living room has built-ins and is flooded with light. A first floor bedroom and en suite full bath complete this floor. The second floor meanders as only an old house can, there are 4 bedrooms, a large hall bath and an office space. A brand new fence surrounds the backyard giving a lovely amount of privacy in this quintessential village home - moments to the library and town beach.

Stylish and chic custom condo at Lenox Woods. Spacious great room with open living. Four bedrooms 3.5 baths. Screened porch and stone patio bordering on Kennedy Park. This centrally located condo is right in the midst of all the culture that the Berkshires offer. Restaurants, theater, Tanglewood. Steps to hiking, a short drive to skiing.

Step out your back door and onto the mountain--this unique slopeside condo offers direct access to skiing and hiking trails right from your backyard. Offering 2,750 sq. ft., this beautifully updated 3-bedroom, 2½-bath home features a gas fireplace and refreshed kitchen with quartz countertops, subway tile backsplash, and GE Profile appliances. Updates include newer carpeting and paint, California Closets, and USB/USB-C outlets. The unfinished basement offers generous storage, home gym or future living space and is stubbed for plumbing. Enjoy peaceful mountain surroundings and a community pool in warmer months. Just a short drive from Lenox and Tanglewood, with easy access to dining, shopping and the best of the Berkshires

Enjoy comfortable, move-in-ready living at this inviting Sheffield property, complete with a barn and access to a nearby pond for fishing and kayaking. The versatile layout is ideal for extended family, guests, a home office, or supplemental rental income. Sheffield Center is approximately two miles away, offering restaurants, the Bushnell-Sage Library, the Sheffield Historical Society, and the welcoming character of this historic Berkshire village. Great Barrington's restaurants, shopping, and everyday conveniences are just 15 minutes away, while Canaan, Connecticut, is approximately 10 minutes away.

Be home for the holidays in this truly special Berkshire retreat, where rustic charm, natural beauty, and complete privacy come together. Nestled on over three acres of serene, beautifully landscaped grounds, this one-of-a-kind Lanesborough home offers a peaceful escape surrounded by nature and wildlife. Inside, gorgeous exposed wooden beams, soaring vaulted ceilings, and a magnificent stone fireplace create a warm and inviting atmosphere, perfect for celebrating the holiday season and making lasting memories. The expansive first-floor primary suite features walk-in closets and a spacious en-suite bathroom. A welcoming front porch and spacious deck provide beautiful settings to relax, entertain, or simply enjoy the tranquility of your surroundings.

Dramatic Price Reduction creates opportunity for updates and remodel. Gracefully situated on a gentle sloping hillside street this distinctively designed, quality built, multi-level home offers distant neighborhood mountain views. Abutting the rolling meadows of Arrowhead, Melville's historic home to embrace privacy, natural beauty much like the famed author. Surrounded by artfully designed gardens, this architecturally refined residence is a private enclave offering 4-5 bedrooms, 3 full bath, masterfully landscaped set on 1.5 acres with unique tree selection, blooming shrubs and pollinator flowering perrenials. Just 10 minutes to the culture, cuisine and art offerings of Lenox especially the sounds of Tanglewood. Minutes to all that is Berkshire while being immersed in renowned peaceful

Enjoy privacy on 2.38 acres in this four-bedroom home with natural light, hardwood floors in the main living area, a stone fireplace, and seasonal valley views. The kitchen features oak cabinets and granite countertops, with a dining area for everyday meals and gatherings. Four bedrooms and 1.5 baths are on the first floor. The partially finished basement offers electric heat, a pool room, bar, and office or workout space. Two buildings provide 6 oversized garage spaces plus storage; the garage has a separate electric panel, heat, and hot water. Potential accessory dwelling unit: one bedroom, living room, half bath, and separate first-level exit, with a full bath and laundry in the basement. Convenient to Routes 112, 66, and 20. Room for equipment and everyday living.

Beautiful upper unit with seasonal serene water view of Laurel Lake. The main level boasts open great room and dining with walls of windows washing the space with natural light, wood burning fireplace, screened porch and vaulted ceilings. Updated kitchen with additional eating space, large island, ample storage, washer and dryer. Gracious main level primary with sliding glass doors to the porch, walk in closet and en suite bathroom with oversized jacuzzi tub, double sinks, water closet and separate shower. Completing the main level living is a lovely bedroom with full bath that can be accessed from both the main hall and bedroom. Second level offers a private guest suite with bedroom, full bath and private deck overlooking the bucolic setting. Association offers a brand new pool and

Dating from the late eighteenth century, this handsome, hip-roofed Colonial home is a distinctive and stately presence gracing its two and one half acre site in historic South Williamstown and provides a glimpse into its storied past. The finely proportioned residence offers casual elegance with its three fireplaces, wide board flooring and extensive built-in cabinetry and shelving. With a unique hand-painted wall mural of Williamstown's iconic scenery complementing the warmth of the original old world architectural details, the spacious dining room awaits the hosting of many gatherings both intimate and large. The kitchen overlooks a bright solarium with woodburning stove and ample bookshelves, perfect for relaxation and reading or simply viewing the meadows beyond. Three to four bedrooms

Loads of room for family and friends in this semi-private country home near The Old Inn on the Green and The Southfield Store Café. The first floor features spacious living areas, including a living room with a wood-burning fireplace, a large eat-in kitchen and dining area, and a paneled den, along with an attached two-car garage. Two of the six bedrooms are on this level, including the primary and an adjacent bedroom currently used as a home office. The adjoining room offers the potential to create an expansive en-suite bath and walk-in closet. Upstairs are four generously sized bedrooms, a full bath, and a large laundry room. A full basement provides ample storage and houses a new Buderus boiler. Set well back from the road, the property enjoys a large, private backyard.

Experience year-round magic at this classic 1925 lakefront cottage, set on a private point of Shaw Pond with 60' of direct shoreline. Panoramic water and mountain views unfold from the screened porch, while a stone fire pit sets the scene for sunset gatherings. Inside, renovated, light-filled spaces include an open living room with stone fireplace, fully equipped kitchen, updated full bath, and laundry. Upstairs, three cozy bedrooms and a half bath offer a peaceful retreat. A private summer dock invites kayaking, paddleboarding, and motorized boating, while winter brings ice fishing and skating. Just 13 minutes to downtown Lee, 24 minutes to Tanglewood, and 20 minutes to Jacob's Pillow. Berkshire lakefront living at its best, in every season!

This 1860's Italianate has been thoughtfully restored and improved over the years. With nearly 3800sq ft, this magnificent home offers ample space and a flexible floor plan. Gleaming hardwood floors, timeless trims and mouldings, and decorative fireplaces adorn many of the rooms. A beautifully remodeled, eat-in kitchen is ideal for those who love to cook! There are 3 full bathrooms, and 5 spacious bedrooms. The Main Suite includes a walk in closet with custom cabinetry, and a full bath with a soaking tub. An option for a first floor bedroom opens up possibilities for multi-generational living. The second floor offers a bonus space perfect for a family or media room. Need a home office or studio? There are plenty of suitable options. Many recent improvements add value and convenience to

Charming open-concept Ranch includes a separate abutting building lot in the heart of the Berkshires on a quiet non-through street! This beautiful, move-in ready Ranch offers 1,959 sq ft of bright, inviting living space on the main level. Finished 1159 sq ft basement with full bath adds extra space, perfect for a game room, holiday gatherings. The dining area connects to a large kitchen with newer quartz countertops. Great room features a natural gas fireplace. With 3 spacious bedrooms,3 full bathrooms, there's plenty of room for everyone. Outside, enjoy a welcoming front porch with nice landscaping or host a barbecue on the large back deck. Complete with an attached 2-car garage. Close to Berkshire attractions, 15 minutes to Tanglewood, and minutes to shopping, this home truly has it all!