luxury houses with terrace for sale Pittsfield, United States

2 bed, 2 full bath Berkshire retreat. The bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch and 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand new back deck, an ideal setting for summer evenings. 2 bedrooms on the second floor, with a full bath and dreamy tub. Meticulously-maintained home with a new 200-amp electrical service, this turnkey retreat ensures total peace of mind. Expansive back yard with basketball court and shed. Whether you're enjoying the classic rocking-chair porch or exploring nearby trails and boutiques, this sweet sanctuary is a rare find in the heart of Berkshires.

Beautifully renovated historic farm house available in Lenox, Massachusetts. A charming 1840s clapboard house located on the estate of ''Brookhurst,'' one of the famed Berkshire ''cottages,'' this former guest house has 3 or 4 bedrooms and 2 full baths spread over three floors (primary bedroom and bath on main floor). It has a private gated driveway and an attached 2-car garage. Luxurious traditional decor throughout the home but with all the modern conveniences including AC, wifi, whole house generator and more. A flagstone terrace overlooks the lush backyard and fully planted walled garden. The house benefits from the rolling landscaped vistas of the beautifully maintained estate property it abuts. Minutes to the town of Lenox and to Tanglewood!

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody and Stearns, this Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace below. Guided by museum-quality principles, long stretches of UV-protected wall space give way to precisely framed vistas. Board-formed concrete walls mitigate winter winds, while the exterior is clad in enduring, low-maintenance Vermont slate. Embracing sustainable luxury, the three-bedroom, two-study home features triple-glazed windows, super-insulated envelopes, and geothermal climate control.

Welcome to this wonderful Colonial in a quiet, sought after neighborhood in Lee, MA. 3 bedrooms, 2.5 baths, and a finished lower level. Enjoy an expansive deck overlooking the rear yard; providing plenty of outdoor living space. Amenities include vinyl siding, gas heat, hardwood floors, eat-in kitchen, dog fence, and a two car attached garage.

Quitessential 1831 side hall Colonial. Charming home located in the village of Interlaken in the town of Stockbridge, MA. Just minutes to Lenox, downtown Stockbridge, and the Berkshire Botanical Center. Listen to the babbling water from the Larrywaug Brook and visit the nearby town park. Sit on the deck or around the firepit to soak in the atmosphere of privacy and peace. This 3 bedroom, 1.5 bath house has been meticulously updated. These updates include: roof, windows, deck, painting, kitchen, baths, cement clapboard, wood flooring, laundry on main level. Full walkout basement, oil heat, central air, town water, town sewer. Garage is partitioned for a workshop but can easily be converted to a one-car garage again.

Tucked into the woods of Sherwood Greens and just a short walk to Long Bow Lake's private beach, this home is the kind of Berkshire retreat you have been looking for. Set on 2.35 acres with privacy on both sides, it offers the peaceful, tucked-away feeling of a cabin in the woods while remaining just minutes from Lee and the Berkshires' renowned cultural attractions, including Jacob's Pillow, Tanglewood, and the area's vibrant restaurants, shops, and hiking trails. One of the community's greatest attractions is Long Bow Lake itself, a quiet non-motorized lake enjoyed by kayakers, canoeists, paddleboarders, and those seeking a more peaceful pace. Inside, cathedral ceilings, warm pine walls, and a wood stove create an inviting atmosphere that feels instantly welcoming. Offering 1,764 square feet, the spacious living room opens to the dining area, creating a comfortable gathering space filled with natural light and character. Sliding glass doors lead to a brand new deck overlooking the surrounding woods, while a cozy den, kitchen, and half bath complete the first floor. Upstairs, the primary suite features a private bath with a soaking tub, while two additional bedrooms share a full guest bath. Whether you're spending the day at the community beach, paddling across the lake, exploring nearby Berkshire attractions, or relaxing by the fire after a day outdoors, this home captures the laid-back lake lifestyle that makes Sherwood Greens so special. Private, peaceful, and full of charm, 410 Long Bow Lane is the kind of place where weekends turn into entire summers.

Timeless farmhouse charm meets modern luxury in the heart of Old Chatham. Set on 1.4 picturesque acres, this beautifully renovated 1875 home has been thoughtfully restored from top to bottom, blending historic character with contemporary comfort. Inside, you’ll find sun-filled living spaces, gleaming hardwood floors, a gourmet kitchen featuring a Wolf range, Bosch appliances, quartz countertops, and custom solid wood cabinetry, plus three spacious bedrooms, 2.5 designer baths, and an oversized dressing room. Outside, enjoy a brand-new wraparound porch overlooking peaceful grounds that invite morning coffee, evening cocktails, and everything in between. Whether you’re searching for a full-time residence or the perfect Hudson Valley weekend escape, this move-in-ready home offers the rare combination of classic farmhouse warmth, exceptional craftsmanship, and effortless living in one of Columbia County’s most charming villages.

Tucked away on 3.6 serene acres, this bright and airy single-level home is the perfect year-round escape. This completely renovated home offers an open concept main living area including the dining room, efficient eat-in kitchen with stainless steel appliances, and family room with wood stove, perfect for relaxation and entertaining. Two additional guest rooms and a den. The newly-completed primary suite boasts a beautiful bathroom and an oversized walk-in closet versatile enough for a home office. Outside, the private grounds feature a dining patio, fire pit, gazebo, and shed. Located just minutes from the slopes of Ski Butternut and downtown Great Barrington, this turnkey property also features a proven track record as a short and long term rental. Propane has been added with additional plumbing to set up gas-powered cooking if desired and possibility to convert wood stove to a gas option. House plumbed for forced air system. The primary suite features radiant floor and a heated towel bar, as well as a new mini split system in 2021. High efficiency tankless Rinnai water heater. Close cell spray foam insulation throughout the house, all exterior walls, crawlspace, and foundation walls. Whole house water filtration system with three stage filter and water softener. Roof replaced in 2021. Ring security system with camera. Whole house dehumidifier in crawl space.