Updated and spacious condo just a short distance from Main Street Stockbridge, downtown Lenox, and all the Berkshires has to offer! Premier Unit at Stockbridge Terrace: Enjoy peaceful living on a private cul-de-sac with a limited number of units. The main level living setup is perfect for the primary resident, featuring a large primary bedroom with an en-suite bath and walk-in closet, an open-concept kitchen that has been recently updated complete with top-of-the-line appliances and all new high end cabinetry. The Great Room boasts cathedral ceilings bringing an abundance of natural light and a soaring gas fireplace for added ambiance. Enjoy your private backyard views from the 4-season sun porch equipped with both heat and A/C for year-round comfort.

Welcome to elegant single-level living in one of Lenox's most coveted locations. Ideally positioned on prestigious Saint Andrews Drive, this exceptional home offers privacy, comfort, and stunning views--just minutes from the heart of the Berkshires.This expansive 3,379-square-foot residence features four bedrooms and four full baths, thoughtfully designed for both everyday living and entertaining. Each bedroom includes its own private bath, ensuring comfort and privacy for family and guests alike.A grand living room with soaring ceilings and a double wood-burning fireplace flows seamlessly into a cozy den, separate office, and formal dining room. The gourmet eat-in kitchen is beautifully appointed and enhanced by custom woodwork and artistic tile details throughout.

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle.The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen adjoins the dining area, creating an ideal space for entertaining. With three full floors of living space, the home offers four ensuite bedrooms plus an additional bedroom, providing comfort and privacy for family and guests. Enjoy seamless indoor-outdoor living with a screened porch off the main level leading to spacious decks and a hot tub. The lower level includes a media room and sauna for relaxation

The thoughtfully renovated and expanded 1940s Main House is full of exceptional spaces--elegant formal dining and living rooms in front, informal sitting area and spacious eat-in kitchen at the back, stunning central stairwell, cozy den/bar, and media room. Five comfortable bedrooms, including two luxurious primary suites. Every material, sightline, and design element has been curated with care and sensitivity. Delightful outdoor spaces abound--front and rear goshen stone patios, rolling lawns, balconies and roof spaces. Cozy historic sunroom off the living room. Above the oversized two-car garage, is a stunning light-filled studio with intricate ceiling details, exterior balcony and bathroom. The in-ground pool is surrounded by a huge patio area, gardens and pastoral views.

Welcome to an extraordinary lakefront estate on the shores of Pontoosuc Lake, an offering that sets a new benchmark for luxury living in the Berkshires. With over 7,494 square feet of total space, including exceptional garage capacity ideal for car collectors or hobbyists, this remarkable property offers unparalleled scale, versatility, and setting.The main living area showcases a thoughtfully designed open floor plan that flows seamlessly toward the water, ensuring the views are always front and center. Enjoy sweeping northern-facing vistas of Pontoosuc Lake, Mount Greylock, and the surrounding Berkshire hills. Whether relaxing on the expansive deck, swimming in the in-ground pool, or departing from your private dock, the connection to nature and water is ever-present.

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.