luxury property for sale East Chatham, United States

Nestled in the picturesque Berkshires, this historic circa-1776 Richmond estate seamlessly blends Colonial charm, timeless elegance, and premier equestrian amenities. The expansive compound features a beautifully maintained seven-bedroom, 7.5-bath main residence/Inn, three guest cottages, multiple barns, and a spacious entertaining barn. The distinguished main home offers a gracious dining room, entrance parlor, stately library, cozy den, period greenhouse, and well-appointed kitchen. An equestrian enthusiast's dream, the property boasts lush paddocks, multiple barns, a 6,000-square-foot heated indoor riding arena with viewing area and owner's apartment, and a professional outdoor riding ring, providing exceptional facilities for year-round training and entertaining.

Down a long, private drive lined with mature maple trees, a remarkable piece of Hudson Valley history awaits. Set within luxurious privacy yet just a pleasant walk from the heart of Kinderhook, this extraordinary antique Dutch Colonial offers the rare combination of architectural authenticity, refined modern comforts, and effortless access to one of the region’s most charming villages. Public records date the home to 1840, though references to its origins reaching back to the early 1700s add another layer to its already fascinating history. For those who appreciate early American architecture, homes with this degree of original character are increasingly difficult to find. From the moment you enter through the classic double-hung Dutch door, your foot meets the aged wide-plank floors of the foyer and the feeling is immediate: this is a home with stories to tell. Two grandly proportioned parlors flank the entry, each anchored by an impressive brick fireplace. To the right, the formal living room provides an intimate setting for receiving guests and lingering conversation; to the left, a handsome study offers a quieter retreat. Both spaces have been thoughtfully restored, preserving their original architectural integrity while creating rooms that feel warm, elegant, and entirely livable today. Beyond, a luminous atrium dining corridor draws you toward the informal dining room and breakfast nook, ultimately opening into a spectacular gourmet kitchen. Oversized top-of-the-line appliances, generous custom cabinetry, and another enormous brick fireplace make this the natural gathering place of the house. Framed views extend beyond the kitchen and dining spaces toward a pond and beautifully manicured English-style gardens, bringing the landscape into everyday life. A separate formal dining room just off the kitchen sets the stage for memorable dinners and long evenings with friends and family. Upstairs, five generously proportioned bedrooms each possess their own distinct personality while continuing the architectural language found throughout the home: original details, deep-set windows, aged floors, and the unmistakable sense of permanence that only an antique house can provide. Beautifully designed bathrooms introduce a sophisticated modern counterpoint, including a luxurious steam shower designed for unwinding at the end of the day. Across the property, privately tucked to the side, is an expansive in-ground pool accompanied by a charming two-bedroom, two-bath pool house. Designed as its own private retreat, the guest house allows friends and family to settle in comfortably while the main house remains wonderfully serene. Together, the pool and pool house create an idyllic setting for long summer afternoons, impromptu dinners, and weekends that seem to stretch a little longer than expected. And then there is Kinderhook itself. Just a walk from the property, the village offers a wonderfully curated collection of shops, cafés, restaurants, and a wine bar—places with the sophistication and sense of discovery found in the Hudson Valley’s better-known destinations, but without the weekend crowds. It is precisely the kind of place that feels discovered rather than descended upon. A home of extraordinary provenance, privacy, and presence, this is an uncommon opportunity to own a piece of the Hudson Valley’s architectural history while enjoying the pleasures of contemporary country living. Historic at heart, beautifully evolved, and perfectly positioned in Kinderhook

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.

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

Rare, renovated Berkshire investment compound on 0.59 acres in pedestrian-friendly Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Moments from Berkshire Mountain Bakery; minutes to downtown Great Barrington and Tanglewood. A rare, turnkey find!

A modern country home inspired by the farmhouses of the Hudson Valley. Taconic Creek Road is tucked away amongst rolling hills and large surrounding parcels, on a beautiful dead end road with just a few lovely houses. The palette is restrained but luxurious with a thoughtful layout and custom design details. Spanning 2,100 square feet, you’ll find lime washed walls with stunning depth of color, custom millwork and wideboard wood flooring that adds warmth to the space. The main living area is anchored by the open kitchen, with Tundra Gray marble counters, an English farmhouse sink, custom inset cabinetry and paneled appliances. A deVOL pendant hangs over the kitchen table. The sitting area is lined with custom built bookshelves and there are large, deep windows lining the room. They face out into the garden, and french doors at the center take you onto the patio. There is storage and a built in bench at the entry for your boots and bags, and a lovely bath on the main level with Noguchi pendant lights. Upstairs, a light filled sitting room walks out to a screened in porch, and there are three bedrooms spread out across the floor. The primary suite is large with a stunning picture window, an office/walk-in closet and a gorgeous bathroom. You’ll find a walk-in-shower and soaking tub with views of the surrounding treetops. Two other bedrooms share the third bathroom off the hall. There is an extensive list of upgrades that includes a new roof, HVAC and septic, and the current owners buried the electrical lines to the house. A large pool is surrounded by lilacs and hedges, private and peaceful, and there is a garage for parking. Taconic Creek Road offers a rare level of calm and sophistication just 15m to Hudson and Amtrak and under 2.5h north of NYC.

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)

A very early Hudson home built c1790 likely in the Federal style, 102-104 North Fifth Street was converted into a striking Italianate at the turn of the 19th century. The beautifully ornamental porch is a fabulous place to take in the charming block, and the striking facade is adorned with bracketed cornices typical of the Italianate style. Just blocks to Warren Street, Hudson’s main drag, the neighborhood is residential and quiet. You have a large backyard with a patio, a 6ft fence for privacy, and lovely & mature plantings. Inside, the proportions are as elegant as the exterior, with high ceilings and wide spaces. The kitchen is open, grounded by a center island, and you’ll find large common spaces and small quiet nooks. An office sits at the back of the house, and you’ll find a gas fireplace clad in brick in the living room. A magnificent curved staircase has its original banister, a work of art, and upstairs you’ll find three bedrooms. The primary is ensuite, lovely and large with a soaking tub, separate shower, and double vanity. There is off street parking lined with cobblestone walls, and the double lot offers wonderful outdoor space. A wonderfully quiet corner just a 3m walk to the center of town and all that Hudson has to offer with its renowned restaurants & antique shops, and just up the road from the Amtrak train station. 102-104 North Fifth is completely turn key & done to a wonderfully high standard, just 2.5h north of NYC.

Overlooking ten acres of city-owned green space, this passive house is just two blocks from the best restaurants and shops that Hudson has to offer but a world away. The site is entirely unique within Hudson, the terraced yard is exceptionally private and overlooks pastoral fields, and a small waterfall out back can be heard from the house. The backyard is enveloped by trees, this is one of a few in-town locations where you'll find no neighbors in sight. Built c2015, the incredibly efficient home has 3 bedrooms and 2 full baths spread out over two stories. The main living space is an open kitchen and living room, both walk out onto the deck where one can enjoy the outdoors right in Hudson proper. On the lower level you’ll find radiant concrete floors. The home is clad in COR-TEN steel siding and the European windows are triple-pane. Outside, stone walls terrace the yard, there is a built-in grill/firepit, a large storage shed and off-street parking. This incredibly unique location offers in-town convenience and proximity to nature— it is truly the best of both worlds.

Some addresses simply carry weight and 514 Warren Street sits at the very heart of Hudson's celebrated mile-long main corridor -- the cultural and commercial spine of one of the Hudson Valley's most sought-after cities. This is not just a property. It is a front-row seat to everything that makes Hudson extraordinary. Warren Street has stood at the center of Hudson since the city's founding in 1783, when a group of Quaker whalers and merchants laid out the grid that still defines the city today. The buildings that line it have been called one of the richest dictionaries of architectural history in New York State -- and 514 Warren places you squarely within that legacy. Step outside and you are surrounded by the best Hudson has to offer. The mile-long business district centered on Warren Street boasts dozens of first-tier antique and home furnishing shops, along with an eclectic mix of art galleries, restaurants, and performance spaces. Neighbors at this stretch of Warren include acclaimed galleries, destination restaurants, and boutiques that draw visitors from New York City and beyond every weekend. The Hudson Amtrak station -- offering a direct two-hour connection to Manhattan -- is just blocks away, making this address equally compelling for full-time residents and savvy second-home buyers. Hudson is a small, supply-constrained market with persistent demand driven by second-home buyers, remote workers, and downstate transplants. Inventory remains limited, particularly for move-in-ready historic properties near Warren Street. In short: properties here don't wait. In Hudson's market, authenticity and condition are far more important value drivers than square footage alone -- and a Warren Street address is the very definition of authentic. Whether you envision a sophisticated private residence, a mixed-use live-work property, or a premium commercial space, 514 Warren Street offers the platform to realize it. Hudson's zoning along Warren Street has historically supported a flexible blend of retail, gallery, hospitality, and residential use -- giving the next owner genuine optionality. Well-priced properties on Warren Street continue to attract strong interest , and in a city where scarcity is a permanent feature of the landscape, the window to act is always shorter than it appears.

There are houses that have been renovated, and then there are houses that have been thoughtfully stewarded. Occupying one of the most coveted stretches of Hudson's sought after 500 block of Warren Street, this exceptional brownstone is a masterclass in preservation—a home where extraordinary period architecture has been honored rather than replaced, and where every modern intervention feels quietly inevitable. For those drawn to historic homes, it is an increasingly rare offering. Throughout, original architectural details remain remarkably intact. Towering windows flood the interiors with natural light, while substantial moldings, deep baseboards, elaborate tin ceilings, oversized door casings, solid brass hardware, decorative cast-iron hinges, and weighty original doorknobs speak to a level of craftsmanship that simply isn't replicated today. Every room carries the quiet confidence of another era, lending the home an unmistakable sense of old-world glamour. Yet despite its reverence for the past, the house never feels like a museum. Instead, it possesses a sophistication that is difficult to manufacture—a layered, collected quality that suggests generations of thoughtful stewardship rather than a single decorating project. Rich textures, wallpapers, antique furnishings, and beautifully composed spaces create interiors that feel both deeply personal and effortlessly elegant. Every room has been edited with remarkable restraint from the area's local artisans and antique shops, allowing the architecture to remain the true focal point. The home unfolds across gracious entertaining spaces, intimate bedrooms, and beautifully appointed baths, each one carrying its own distinct character while remaining part of a cohesive whole. From richly paneled rooms and dramatic fireplaces to sunlit bedrooms, every space invites a slower pace and rewards careful attention. Beneath it all, a fully finished walkout lower level adds an entirely different dimension to daily living. Complete with a gym, generous mudroom, and dedicated dog wash, it offers the kind of practical luxury rarely found in historic townhouses, seamlessly connecting to the rear of the property. Outside, private rear parking—an invaluable amenity in Hudson—provides effortless convenience while preserving the home's elegant Warren Street presence. Situated on one of the city's most sought-after blocks, just moments from Hudson's renowned restaurants, galleries, boutiques, and cafés, the location is every bit as exceptional as the home itself. The 500 block of Warren Street has long been considered among the finest addresses in the city, where beautifully preserved nineteenth-century architecture forms one of the most distinguished streetscapes in the Hudson Valley. This is more than a beautifully renovated townhouse. It is a home for someone who appreciates the romance of period architecture, the quality of enduring craftsmanship, and the quiet luxury of spaces that have been assembled with patience. Homes of this caliber are exceptionally rare, and rarer still are those that feel as authentic, sophisticated, and timeless as this one.

Versatile mixed-use property pairing a sophisticated second-floor apartment with a flexible first-floor residence that doubles as an ideal commercial or gallery space. Overlooking a tranquil year-round brook and a private backyard, the offering sits right downtown Egremont and includes the convenience of an ample garage. | Property Highlights | Second-Floor Apartment: Sophisticated, charming living quarters featuring high-quality finishes, total privacy, and serene views of the brook and grounds. First-Floor Mixed-Use Space: Currently configured as a comfortable residential apartment while offering incredible potential for an art gallery, retail boutique, or commercial enterprise. Ample Garage: Generous garage space providing excellent storage, parking, or workshop potential. Exceptional Septic Infrastructure: Robustly engineered system designed to service a 35-seat restaurant. First floor has been a restaurant, bookshop, and now a residence.