Luxury homes for sale & real estate in 01238, MA

Luxury Home for sale in 01238, MA:

Bring your BOAT and enjoy all that the Stockbridge Bowl has to offer. This charming home has deeded rights to the lake, as well as its own dock space! The house was recently renovated with all top of the line mechanicals and appliances. Bosch, Miele, & Fisher Paykel. Central AC. One level living with two bedrooms and two full baths. Open concept living with a large front deck and yard for entertaining. Inside is an original log fireplace for those chilly winter nights. All new cedar lined closets and freshly painted throughout. A three-minute walk to your boatslip and private neighborhood dock, you can sit and watch the sunset from the best spot on the bowl. Make an appointment to vie

Luxury Home for sale in 01238, MA:

Contemporary home built in 2012 on over 11 acres walking distance to Stockbridge center. Original house was taken down and this sun-drenched home was built on the saved footprint. Main floor has a small living area off the entry open to large kitchen and dining with sliders to the deck, primary suite with walk-in closet and deck access, 1/2 bath and access to the oversized garage. Second floor has vaulted ceilings, a large landing, second living area, 2 guest rooms with a hall bath and another primary suite. There are two porches off the second floor, one small off the primary and the other flanking the East side - covered for protected enjoyment. The Konakpot Brook winds through the back o

Luxury Home for sale in 01238, MA:

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

Luxury Home for sale in 01238, MA:

Historic 1815 compound — 3 independent income-producing units — $154K gross revenue in 2025. 1815 Greek Revival farmhouse duplex + converted barn — an investment rental property or family compound minutes from Main Street Stockbridge. Turnkey 5-star Airbnb, 6 years running, $154K/year. On historic registry as birthplace of a U. S. Supreme Court Justice. Compact, low-maintenance parcel — all the Berkshires, none of the yard work. Original wide-beam floors, log rafters, double-sided fireplace with brick vaulted bread oven, mature gardens with bistro tables. Three addresses — 1574, 1577 & 1579 Pleasant St. Each unit fully self-contained with own entrance, k

Luxury Home for sale in 01238, MA:

Extraordinary opportunity to own a showcase of New England history and hospitality--17 Main Street, a masterfully restored Berkshire cottage in the vibrant heart of downtown Lenox. Originally built in 1883 and once owned by Gilded Age shipping magnate John Schermerhorn, this landmark property blends historic grandeur with modern comfort. Between 2021 and 2025, the residence underwent a comprehensive top-to-bottom renovation: a new 30-year roof, upgraded electrical and plumbing, 8.5 renovated bathrooms, custom millwork, and restored original hardwood floors. The gourmet kitchen features a Viking 8-burner oven, KitchenAid designer dishwasher, and commercial-grade refrigeration--perfect for bo

Luxury Home for sale in 01238, MA:

Tucked away in one of Lenox's most desirable neighborhoods, this contemporary ranch has been completely renovated with no expense spared, offering effortless single-level living and a seamless connection to the outdoors. Vaulted ceilings, walls of glass, and an abundance of natural light create an open, inviting atmosphere, while nearly every room overlooks the beautifully landscaped, private backyard. Designed for both everyday living and entertaining, the thoughtfully planned floor plan centers around a stunning eat-in kitchen featuring quartz countertops, premium Thermador appliances and custom floor to ceiling millwork with an easy flow into the spacious living room with a gas fireplace