MOTIVATED SELLER'S! This property has an immaculate fenced in back yard for all your summer activities. Inside boasts beautiful hardwood floors, Full bath on the 1st and 2nd Level. Large mudroom from the main entrance for all you winter and mud season needs. A paved driveway with plenty of private parking. A walkout from the lower level to the parking area with a tuck under car port. Recently painted exterior and a screened in porch in the back. 3 large bedrooms and a perfect den for office space or media room. Centrally located in the Berkshires within close proximity to Shopping, Groceries Stores and Tanglewood!

Location, location, location! Ideally situated within easy walking distance of the village, elementary school, and Tanglewood, this charming ranch offers comfortable single-level living in a quiet, desirable neighborhood. The large, level and semi-private backyard provides plenty of room to relax, entertain, garden, or enjoy the above-ground pool. Inside, the home features a spacious open living area currently used as a dining and family room, separate living room, eat-in kitchen, three bedrooms, and a full bath with tub. Step directly from the kitchen onto the deck overlooking the pool and expansive backyard. Additional highlights include an attached two-car garage, full basement with four versatile rooms, and a designated laundry space complete with a laundry chute!

Nestled on a peaceful street, this inviting 3 bedroom, 1.5 bath home offers the perfect blend of comfort and convenience. Step inside to find a bright and welcoming living space filled with natural light, a cozy dining area, and a functional kitchen ready for your personal touch. The three bedrooms provide plenty of room for family, guests, or a home office, while the updated half bath adds extra convenience. Enjoy morning coffee on the front porch or unwind in the private backyard--ideal for relaxing or entertaining. With sidewalks leading straight to town, you'll love being just a short stroll from shops and restaurants, all while enjoying the tranquility of a quiet neighborhood setting. Move-in ready and full of charm, this home offers small-town living at its best.

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.

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.

Fantastic Offer! Custom-designed & beautifully maintained one-owner residence offering 4 bedrooms, 3.5 baths, in the most desirable location in the verdant Berkshires. Calm & Quiet with direct access to Kennedy Park - you'll enjoy the perfect balance of nature, community & the Arts. Lenox offers quality shops, farmers markets, Botanic Gardens & music. A beautiful open floor plan features a totally upgraded kitchen with gas stone fireplace overlooking the woods. Adjacent screened porch opens to a private paver patio surrounded by native gardens. 1st floor en-suite bedroom provides an ideal 1-level living. Upstairs the spacious primary suite offers double closets, a beautifully appointed bath with quartz countertops, double sinks, generous linen closet, tile tub & shower.

A UNIQUE OPPORTUNITY TO OWN A SPACIOUS LENOX HOME IN A PRIVATE, COUNTRY SETTING AT A REASONABLE PRICE. 4BR, 2.5 BATHS, WITH HARDWOOD FLOORS, OPEN KITCHEN/DINING AREA, LARGE OPEN DECK, PELLET STOVE AND AN IN-GROUND POOL. LOVELY LANDSCAPING WITH STONE WALLS, GARDENS AND OPEN LAWN AREA FOR ATHLETICS OR JUST RELAXING. GREAT CENTRAL LOCATION, A SHORT DISTANCE TO TANGLEWOOD, TOWN AND YOUR FAVORITE BERKSHIRE ATTRACTIONS AND CULTURAL EVENTS.

Don't miss this Lenox beauty tucked away on a quiet side street. Main level w hardwood flooring, living room with crown molding, formal dining w. large bay window, updated kitchen w extensive cabinetry. Family room w gas fireplace opens to large screened porch / patio. First floor laundry and 1/2 bath. Three bedrooms on the upper level; primary suite w adjoining dressing room/ primary bath with soaking tub and separate shower. Two additional bedrooms and full bath; all w hardwood flooring. Central a/c; natural gas heat/hot water; attached two-car garage. Easy maintenance perennial gardens with a focus on native and specimen plantings -over 100 species carefully planned to bloom continuously wowing sight and scent! Abutting preserved land with year-round brook-your own magical retreat!

Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area features a cozy gas fireplace, creating a warm focal point for chilly evenings, while the kitchen comes equipped with sleek, modern appliances. This turnkey residence offers 3 spacious bedrooms plus a versatile 4th full-size room that's ideal for a fourth bedroom, dedicated home office, or quiet retreat along with 2.5 updated bathrooms.

Discover a prime commercial opportunity at 449 Pittsfield Road Lenox, MA. This expansive building boasts approximately 9,000 square feet and features eight versatile office suites, perfect for businesses of all sizes. With ample parking available, your clients and employees will enjoy easy access. Strategically located in a high-traffic area, this property benefits from excellent visibility and foot traffic, making it ideal for retail or professional services. Whether you're looking to invest or establish your business, this location offers a unique blend of functionality and convenience. Don't miss your chance to secure a spot in this vibrant commercial hub!

Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly Views of October Mountain. Plenty of room for family and friends.

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite—pool, fitness center, clubhouse, and tennis—all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite—pool, fitness center, clubhouse, and tennis—all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

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.

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial built-ins create a sophisticated yet comfortable totally renovated interior. Outside, magnificent perennial gardens, privacy, outdoor showers, and courtyard provides a serene retreat. Enjoy access to the nearby Wyndhurst Club and Manor pool, tennis courts, reduced-rate fitness membership, and more. A rare offering combining luxury, lifestyle, and one of Lenox's most coveted settings.

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial built-ins create a sophisticated yet comfortable totally renovated interior. Outside, magnificent perennial gardens, privacy, outdoor showers, and courtyard provides a serene retreat. Enjoy access to the nearby Wyndhurst Club and Manor pool, tennis courts, reduced-rate fitness membership, and more. A rare offering combining luxury, lifestyle, and one of Lenox's most coveted settings.

Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest. The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors.

Crosby House, a property with a storied Lenox history and a location second to none, presents a rare opportunity to own a residence of remarkable character, scale, and flexibility in the heart of the village. Currently configured as two spacious residences, this distinctive multifamily property offers an exceptional array of possibilities. Subject to applicable zoning, permitting, and approvals, the existing configuration may offer the potential to be thoughtfully combined into one extraordinary single-family residence or could provide the foundation for two highly distinctive condominium residences.