Set on a prime Lenox road directly across from Canyon Ranch, this fully renovated antique offers the rare convenience of a sidewalk leading straight into the village center. Shops, dining, Shakespeare & Co., and The Mount are just moments away -- yet the property feels private and peaceful, surrounded by mature trees and gardens.Originally the Gardener's Cottage for the historic Bishop Estate, the home blends preserved character with extensive recent improvements, creating a residence that feels timeless and truly move-in ready.

Discover comfortable & gracious living in this impeccably renovated home in Lenox. 4 BRs & 4 BAs approx. 4,000 sq ft of open, modern design. The entire home is filled w/sunlight & gleaming new red oak flooring & a sleek chef's kitchen outfitted with new Bosch appliances, quartz countertops & significant storage. Functional yet luxurious details throughout- from laundry on 2nd level to mini-split systems, fireplace & a sunroom that promises cozy comfort in all season. Step outside into your private natural oasis: enjoy gatherings w/ woodland views around the fire pit, on deck or patio. Newly finished lower level includes a living, dining & media room equipped with kitchenette & full bthrm. Set in one of Lenox's most desirable neighborhoods, this home provides privacy and convenience.

A ONCE IN A LIFETIME OPPORTUNITY TO BUILD YOUR DREAM HOME ON A SPECTACULAR, 14 ACRE, WATERFRONT PROPERTY IN THE HEART OF THE BERKSHIRES. PRIVATE, QUIET, BUT NOT ISOLATED. FROM YOUR NEW RESIDENCE, BEAUTIFUL LAUREL LAKE IS AN EASY STROLL DOWN THE BOARDWALK TO YOUR PRIVATE DOCK AND SITTING AREA. FIVE MINUTES TO DOWNTOWN LENOX, TEN MINUTES TO TANGLEWOOD AND CONVENIENT TO ALL THE BERKSHIRES HAS TO OFFER. ACLEARED, MANICURED HOMESITE, GRACIOUS ENTRANCE AND AN ENCHANTING STONE BRIDGE OVER A STREAM AWAITS YOU. TOWN WATER, AND UTILITIES AT THE SITE. COME SEE FOR YOURSELF.

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.

Perched atop a gentle hill with distant Berkshire views, this distinguished former Lenox school building known as ''Crystal Hill'' has been thoughtfully converted into 10 residential apartments plus one office space.The historic masonry structure combines character and stability with modern updates, including hardwood floors, spacious layouts, and separate hot water and electric meters for each unit. Strong rental income and solid cap rate make this an attractive investment in one of the county's most sought-after towns.Set on two scenic acres, the property offers ample parking, coin-operated laundry, three storage rooms, and a boiler room. Capital improvements include a Simplex fire alarm system (2014), roof replacements (2015 & 2016), apartment upgrades (2019)

Perched atop a gentle hill with distant Berkshire views, this distinguished former Lenox school building known as ''Crystal Hill'' has been thoughtfully converted into 10 residential apartments plus one office space.The historic masonry structure combines character and stability with modern updates, including hardwood floors, spacious layouts, and separate hot water and electric meters for each unit. Strong rental income and solid cap rate make this an attractive investment in one of the county's most sought-after towns.Set on two scenic acres, the property offers ample parking, coin-operated laundry, three storage rooms, and a boiler room. Capital improvements include a Simplex fire alarm system (2014), roof replacements (2015 & 2016), apartment upgrades (2019)

An Unrivaled 8-Acre Sanctuary of Beauty, Privacy & SophisticationNestled in the cultural heart of the Berkshires, just steps from downtown Lenox, this extraordinary property offers a rare and coveted blend of seclusion and sophistication set on an unheard-of 8 acres of wooded, professionally designed, and maturely landscaped grounds.Inside, the home has been completely reimagined, with every detail thoughtfully curated. Sunlight pours into the open-concept floor plan, seamlessly connecting the gourmet kitchen, grand great room with a striking stone fireplace, and elegant dining area. French doors on either side of the stone fireplace open to a spacious sunroom, where multiple sliding glass doors lead out to a Trex deck overlooking beautifully terraced gardens.

Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for four-season enjoyment of the Berkshires lifestyle--Tanglewood, Lenox village, farm-to-table dining, ski slopes, hiking-this custom-built 2017 home was fully reimagined and entirely updated in 2020 by master craftsmen. Every detail has been elevated to support both elegant entertaining and relaxed daily living.Dramatic ceiling heights and a sun-drenched upper gallery define ... see more

Gated Berkshire Stone Estate in exclusive Pinecroft compound with Canyon Ranch Living and its 125 maintenance-free acres. Optional membership. Turnkey home features elevator, 300-year-old reclaimed timber floors and large gourmet kitchen. Great room boasts floor-to-ceiling stone fireplace, wet bar, Nano doors to screened lanai. Two primary en suite bedrooms with cedar closets. Lower level: gym, sauna, 8-seat hi-def theater, wine cellar, massage room, en suite bedroom/office and a soda fountain. Elegant outdoor living includes heated gunite saltwater pool/spa, firepit, pool house with guest suite and fully equipped kitchen. Heated driveway and garage. Near downtown Lenox, Tanglewood and Berkshire arts.

Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest, and a rare level of privacy and provenance.Arrival.Approached via a long private drive, the property unfolds gradually--passing a sun-kissed meadow, through a grove of majestic pines, past a stunning carriage house, before arriving at an inviting courtyard. The house itself is beautifully sited to capture natural light and frame the sweeping mountain and pastoral views.