luxury house with terrace for sale Old Chatham, United States

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.

Come see everything this charming Victorian home in the country has to offer. Set on 2.5 acres, this beautiful property blends turn of the century charm with thoughtful modern upgrades throughout. Original pine floors, detailed trim work, and a stunning curved staircase speak to the home's early 1900s craftsmanship and timeless character. Upstairs, you'll find three spacious bedrooms and an additional full bath. The fully finished attic offers flexible extra space perfect for a home office, artist studio, movie room, guest space, or possible fourth bedroom. Enjoy morning coffee on the lovely front porch while taking in the privacy and open space surrounding the home. Additional highlights include a whole house generator and walking distance to LaHoff Brewery, a laid back local favorite set inside a restored 1900s barn. Conveniently located just 20 minutes to Hudson, 30 minutes to the Catskills and Albany, and approximately 2 hours to NYC. Recent upgrades and additions include brand new appliances, six Mitsubishi mini split systems for efficient heating and cooling, and a 10x20 lofted barn shed offering additional storage. Thoughtfully maintained and full of charm, this is the kind of Hudson Valley property that feels equally suited for full-time living or the perfect weekend escape.

A mixed use building in the heart of historic Hudson. This c1860 Federal style brick building is a fabulous investment with four beautifully updated apartments. Gut renovated in 2021, the building is completely turn key and has retained much of its historic charm. You’ll find a studio garden apartment in the lower level, a 2BR apartment on street level which could also be used as commercial/retail space, a 2BR apartment on the second floor, and a stunning duplex takes up the top two stories. Off-street parking for three cars in the rear, a fenced in yard planted with lovely perennials and a deck. With minimal maintenance and a healthy cap rate, 358 Warren is an incredible location, a wonderful opportunity for live/work or a pure investment play. Walking distance to Amtrak and in the heart of all that Hudson has to offer.

4 Union St offers a fabulous location, incredible views and comfortable living just steps from the Amtrak station. The c1830 townhouse on desirable lower Union Street is an early example of the federal style in a town renowned for its architecture. Inside, the home has been wonderfully modernized while still remaining true to its historic roots. Walls have been opened on the ground floor to create a large and light filled open space, the living room and kitchen connected. An old brick mantle grounds the living room, and a large center island grounds the kitchen. The ceilings are high, the windows are large, the wide old growth pine floorboards are original. The second floor has also been reimagined, opened up into a single, large bedroom designed with gorgeous views of the Hudson River taking center stage. The third floor at the home’s highest elevation has a large open landing and two small rooms at the house’s southern end. Currently used as offices, both have windows overlooking the Hudson Athens lighthouse, an incredibly rare and coveted vantage point, and the Catskill Mountains beyond the river. One of the best views that this charming rivertown has to offer. The lower level of the home has been converted to additional living space with a bedroom and full bath It walks out to a lovely and sizable tiered courtyard with expertly laid stonework and perennial plantings. A sun filled spot when the weather turns. 4 Union is all buttoned up, steps to the Amtrak and all that Hudson has to offer.

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.

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.

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!

Newly completed and set on 11.7 private acres in the heart of Hillsdale, this architect-designed 4-bedroom, 4-bath modernist residence combines striking contemporary architecture with sweeping pastoral and mountain views in every direction. Arriving via a long private driveway, rolling lawns and open fields unfold toward a home defined by bold geometric forms, expansive walls of glass, and a seamless connection to the surrounding landscape. Just minutes from the Hamlet of Hillsdale, Catamount Mountain Resort, Great Barrington, and Hudson, the property offers a rare balance of architectural refinement, privacy, and access to the region’s most desirable destinations. The residence is centered around a dramatic great room with a soaring 20-foot vaulted ceiling and a wood-burning fireplace clad in richly toned chestnut marble. Floor-to-ceiling glass and oversized Arcadia sliding doors dissolve the boundary between interior and exterior, opening onto more than 540 square feet of covered outdoor living space designed for year-round entertaining and relaxed outdoor living. Throughout the home, natural light shifts across clean architectural lines and warm materiality, reinforcing a strong connection between structure and landscape. The kitchen serves as both a design centerpiece and functional workspace, featuring custom walnut cabinetry crafted by a Brooklyn cabinetmaker, integrated Fisher & Paykel and Bosch appliances, an oversized monolithic island, and a 48-inch double-oven gas range. A fully equipped butler’s pantry and bar area provides additional prep space, storage, second dishwasher, and additional refrigeration, allowing the main kitchen to remain clean and open for entertaining. The primary suite is a private retreat with vaulted ceilings, a custom dressing room, and a spa-like bath finished in dramatic Calacatta Violetta marble, featuring a soaking tub, oversized shower, and fluted glass steel-framed doors. Upstairs, a second ensuite bedroom offers its own walk-in closet and marble-appointed bath, complemented by an additional guest bedroom suite. A versatile fourth bedroom on the main level provides flexible use as a guest suite, office, media room, or wellness space with direct access to the outdoor terrace. Designed for high-performance modern living, the home includes spray foam insulation, high-performance windows, forced-air heating and central air conditioning, on-demand hot water, Lutron lighting controls, remote-access thermostats, generator hookup readiness, and a detached heated 26' x 26' two-car garage. Located just minutes from Catamount Mountain Resort and within easy reach of Great Barrington and Hudson, the home places owners at the center of the Hudson Valley and Berkshires lifestyle. Days might begin with coffee overlooking the fields, followed by a visit to the Saturday farmers market, skiing at Catamount, or hiking nearby trails. Afternoons can be spent browsing Hudson’s celebrated design and antique shops or exploring the galleries, bookstores, and restaurants of Great Barrington. Evenings bring performances at local theaters and live music venues, or a quiet return home as the light settles across the landscape. The setting balances architectural refinement, outdoor recreation, and cultural depth in equal measure. A rare expression of contemporary Hudson Valley living, where architecture, light, and landscape are held in perfect balance. An adjoining 6.73-acre parcel is also available for purchase, offering the opportunity to expand the estate or create a private family compound. (listing agent has a financial interest in the property)

Pride of ownership resonates through this distinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut Street near the esteemed Pittsfield Country Club and Upstreet Cultural District, and just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character, boasting five bedrooms and two and a half baths, thoughtfully improved over the long term owners' commitment to preservation and restoration. This prominent manor style home may be coupled with the neighboring guest house which features 3 bedrooms and 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends, or caregivers.

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.