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$1,745,000
4 Beds ⋅ 3 Baths ⋅ 909070 MLS
This historic house is a timeless beauty. Ice skate on the pond, garden in the greenhouse, and fish and swim in the creek, which borders the property on its south side. Looking for a meditative practice? Stroll the orchard, practice your art in one of the many outbuildings perfect for a studio, or read a book in your very own library. The kitchen, with its huge picture window, is always sunny, and the bedrooms are well-sized, each with their own view of lush garden beds, stone walls, gravel paths and hedges. Enjoy Old-World charm (wide floorboards; stacked-stone exterior; an enormous brick fireplace) while being comforted by modern luxuries (new windows; re-modeled bathrooms; and a kitchen with quartz countertops, a cast-iron sink, and deVOL fixtures). Come and enjoy the view - weeping willows, 300-year old maple trees, and other rare specimens abound. A rare Hudson Valley find, this home has to be seen to be understood.

202 Buckwheat Bridge, Germantown
$1,750,000
4 Beds ⋅ 3 Baths ⋅ 1016435 MLS
SKY FARM MODERN. Designed by renowned architect Will Meyer, Sky Farm Modern is a masterful expression of minimalism, where every element serves a purpose and form and function exist in perfect harmony. A winding drive through the woods reveals a striking composition: a sleek, dark rectangular volume punctuated by a luminous white cube and a dramatic cutout. The white cube houses the kitchen, flooding the heart of the home with natural light and tranquil woodland views, while the architectural cutout creates a covered carport that lends visual lightness to the structure. Step inside and arrive at the center of the home, where an expansive open living space is framed by an entire wall of glass leading to a generous deck overlooking the treetops, with seasonal views of the lake beyond. A suspended fireplace serves as both a sculptural focal point and a source of warmth, while the chef’s kitchen is appointed with premium appliances and high-end fixtures. Wide-plank ash flooring runs throughout the main level, adding warmth and understated elegance. A gallery-like hallway extends the length of the residence. At one end, the private primary suite features an en suite bath with a deep soaking tub and a wall of glass opening onto a secluded deck. Two additional bedrooms along the hall also enjoy direct deck access and share a beautifully appointed bathroom complete with a sauna. At the opposite end of the home, a spacious guest suite offers its own en suite bath and breathtaking corner-wrapped glass walls that immerse the room in natural light and surrounding forest views. A sculptural circular staircase descends to a finished lower-level room with cork flooring and abundant storage. Equally suited as a media room, artist’s studio, fitness space, or home office, it offers exceptional flexibility for modern living. Offering remarkable privacy and requiring minimal upkeep, Sky Farm Modern is an ideal retreat—a refined sanctuary where exceptional architecture and nature come together in perfect balance.

312 Sky Farm Road, Copake
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 1053041 MLS
A Grand Macy Residence -- A Timeless Piece of Hudson's History. Once home to Gertrude and Hiram Macy, descendants of one of Hudson's early founding families who arrived from Nantucket, MA, in the 18th century, this Victorian-era residence showcases remarkable craftsmanship and architectural grandeur that simply cannot be reproduced today. Over the past 13 years, the current owners have lovingly maintained and meticulously renovated the residence, preserving its historic character while introducing modern comforts. A beautifully appointed gourmet kitchen with a Wolf range and Liebherr refrigerator, an updated first-floor full bath, and air conditioning complement the home's charm. Outdoors, improvements include a freshly painted exterior, new cedar siding, deck, fencing, and blue stone patio, along with a hot tub tucked into its own private nook. From the moment you enter this historic home, high ceilings, crown moldings, marble fireplaces, and a magnificent curved staircase with carved details showcase the craftsmanship of a bygone era. Intricate hardwood inlays and contrasting woods create mosaic-like patterns underfoot. The living room fireplace has been converted to gas. A formal living room and dining room set the stage for memorable dinner parties, while the beautifully landscaped yard invites entertaining on a grand scale. A den with French doors opens to a deck and sitting area, with a blue stone patio below. After a stroll along Warren St., retreat to the sunroom with a good book or enjoy a leisurely afternoon summer nap. Ascending the curved staircase is an experience in itself, leading to three bedrooms and two updated full baths, including a primary with an en-suite. The once-barren yard has become a spectacular private oasis, with flowering plants, lush shrubs, and trees creating a tapestry of seasonal color that must be seen to be believed. Stone steps lead to an expansive lawn, complemented by an additional side lot included in the sale. There's ample room for a swimming pool, subject to necessary approvals. What sets this property apart is the elegance of a stately residence, the serenity of a country estate, the convenience of living in the heart of town, with easy access to Amtrak and New York City just two hours away. 525-527 Union Street is a one-of-a-kind property that must be experienced to be truly appreciated.

525-527 Union Street, Hudson
$1,850,000
3 Beds ⋅ 4 Baths ⋅ 1022485 MLS
A c1865 Italianate farmhouse set back from the road under mature willows and maples, with the arched dormer, bracketed eaves, and double-leaf paneled front door that mark the period. The house has been kept close to original — wide pine plank floors throughout, tall windows, a carved wood mantel with a green marble surround in the living room — while the systems underneath it have been fully updated. Main level- Double front doors open to a side stair entry hall with original pine flooring and mud room space for your jackets and shoes. The living room holds a bay window, a period mantel, and leads through to a green-walled study with a sitting area and desk. The kitchen and dining room are the result of a recent addition. The kitchen features black cabinetry, brass hardware, butcher block counters, and a zellige tile backsplash and range hood; a wall of windows over the sink looks out to the willows. A blue-walled family room and adjoining dining area spills out to the back patio for easy gathering and entertaining. A full bath with laundry and main floor bedroom complete the level. Upper levels- The second floor has 2 bedrooms, one beautifully appointed at the front of the house, with a full hall bath. The primary suite is anchored by a wall of built-in bookshelves, has a walk in closet and en suite bath. A finished third-floor room under the eaves, lit by a skylight, works as a sleeping loft or playroom and includes a full bath. Grounds A deep, tree-lined lot with mature plantings, a boxwood-edged path to an in-ground salt water pool with a stone patio, bordered by perennial beds. There is a small accessory dwelling for an office, art studio or yoga room. Location On County Route 19 in the Town of Clermont, Columbia County — between Red Hook and Hudson, with easy access to the Taconic State Parkway and the Amtrak stations in Rhinecliff and Hudson.

1788 County Route 19, Red Hook
$1,850,000
3 Beds ⋅ 3 Baths ⋅ 1028112 MLS
Beaver Mountain Farms is an exceptional 41-acre Hudson Valley estate in the picturesque town of Ancram, Columbia County, offering an extraordinary opportunity for agriculture, equestrian pursuits, or a private country retreat. At the heart of this remarkable property is an impressive collection of farm buildings, including a classic dairy barn, an expansive 80' x 200' steel barn ideally suited for an indoor riding arena, equipment storage, agricultural production, or event space, along with workshops, office space, and a detached artist studio. Rolling pastures, open fields, and a tranquil pond create an idyllic landscape that embodies the timeless beauty of the Hudson Valley while providing endless possibilities for farming, livestock, horses, or creative ventures. Complementing the exceptional farmstead is a beautifully updated three-bedroom, two-and-a-half-bath farmhouse featuring a gourmet kitchen, inviting propane fireplaces, a spacious primary suite with an ensuite bath, and expansive windows that frame breathtaking views of the surrounding countryside and in-ground pool. A partially finished basement offers additional flexible living or workspace. Ideally located near Hudson, Copake, Hillsdale, Millerton, and Great Barrington, Massachusetts, Beaver Mountain Farms offers the perfect balance of rural privacy and convenient access to the Hudson Valley's renowned restaurants, cultural attractions, farmers' markets, and outdoor recreation. This is a rare legacy property where agricultural heritage, modern comfort, and boundless opportunity come together in one of Columbia County's most desirable locations.

1030 County Route 27A, Ancram
$1,950,000
4 Beds ⋅ 3 Baths ⋅ 1033983 MLS
Commanding one of the highest residential elevations in the Hudson Valley, this extraordinary custom residence enjoys breathtaking, uninterrupted views across the Catskill Mountains and Hudson Valley, offering spectacular sunsets, endless skies, and extraordinary stargazing from the privacy of your own mountaintop retreat. Thoughtfully designed for luxurious everyday living and effortless entertaining, the home features a chef's kitchen appointed with premium Bosch, Sub-Zero, and other high-end stainless steel appliances, a gas cooktop, a handsome butler's bar, and exceptional custom cabinetry and built-ins handcrafted by renowned local artisan Vormer Cabinetry of Hillsdale. Superb craftsmanship is evident throughout, complemented by high-performance insulated Pella windows that enhance comfort and energy efficiency while framing the spectacular views. The dramatic great room is anchored by a striking stone fireplace with a reclaimed wood mantel, while a marble gas fireplace with a wood mantel creates an inviting atmosphere in the den. The spacious primary suite enjoys magnificent views and is complemented by an open spa-inspired bath, laundry, and generous closet space. The spacious two-car garage offers abundant storage for outdoor equipment, bicycles, paddleboards, and kayaks, perfectly complementing the property's proximity to Queechy Lake, Stockbridge Bowl, and the region's exceptional outdoor recreation. Modern conveniences include app-controlled security cameras and heating and cooling systems, allowing effortless remote management of the home. Outdoor living is equally impressive, with expansive decks and patios positioned to capture the extraordinary views, multiple barbecue and fire pit areas, and a heated saltwater swimming pool creating an exceptional setting for entertaining or quiet relaxation. A charming pool house with its own outdoor grilling patio extends the outdoor living experience, while the walkout lower level opens to an additional stone patio and fire pit--another spectacular vantage point from which to enjoy unforgettable Catskill sunsets beneath expansive evening skies. Raised garden beds, ornamental flower gardens, and fenced vegetable gardens with programmable drip irrigation provide an ideal setting for growing vegetables, herbs, and flowers. Flexible living space offers additional guest accommodations, while a backup generator provides year-round peace of mind. An additional five-acre parcel is included in the sale, presenting an exceptional opportunity to construct a guest house, studio, office, or other accessory structure, subject to approvals. Located within an exclusive community with privately maintained roads, the property offers exceptional privacy while remaining just minutes from Chatham, Hudson, and the Berkshires. Enjoy easy access to acclaimed dining, boutique shopping, yoga and Pilates studios, organic markets, farm stands, theater, antiquing, and renowned cultural destinations including Tanglewood, Jacob's Pillow, Stockbridge, Lenox, Egremont, Great Barrington, and the Shainman Gallery. Convenient to the Taconic State Parkway, Interstate 90, New York City, Boston, and Albany International Airport, this remarkable residence offers the very best of Hudson Valley luxury living.

116 Ridge Road, East Chatham
$1,950,000
4 Beds ⋅ 3 Baths ⋅ 1042663 MLS
Perched high above the Hudson Valley, Sunset House is an exceptional modern country residence offering over 3,000 sq ft of beautifully renovated living space, extraordinary views, complete privacy, and an uncompromising level of craftsmanship. From its elevated position in Germantown, the house captures an expansive 360-degree panorama Catskill Mountain views to the west, the Berkshire foothills to the east, and luminous sunsets that transform the landscape each evening. The property has been comprehensively renovated with a sophisticated, natural palette and an emphasis on exceptional materials and craftsmanship. Wide-plank white oak floors, custom solid-wood doors and trim, Anderson casement windows, custom lighting, new electrical and plumbing, and a new standing-seam metal roof and HardiePlank siding create a house that feels both contemporary and enduring. The architecture is oriented toward the landscape, with oversized windows bringing the surrounding mountains into nearly every room. In the living room, the effect is particularly striking--the house seems to float above the valley, with uninterrupted views and a new gas fireplace providing a warm counterpoint to the expansive setting. At the center of the home is a custom-designed kitchen combining KraftMaid cabinetry with substantial solid black walnut elements and a custom island surround crafted locally by Cross & Miter. Calacatta Verde marble tile, solid quartz surfaces, raw brass hardware, and a full suite of Bertazzoni appliances create a kitchen that is as beautiful as it is functional. A sophisticated wet bar, complete with wine, beverage and snack refrigerators, hammered stainless sink, quartz surfaces, and custom butternut shelving, extends the entertaining spaces. Four generously proportioned bedrooms, with flexibility for a fifth, include a newly created primary suite with private bath, custom closet, and a large private porch overlooking the surrounding landscape. Three beautifully appointed full baths feature hand-cut fireclay and terracotta tile, marble and quartzite, custom vanities, polished nickel fixtures, deep soaking tubs, and walk-in showers. Every closet features custom-built hardwood interiors. Outside, the property is designed for effortless summer living. The pool occupies a prime position against the mountain views, surrounded by new bluestone coping, new fencing, a brand-new pool house, and mature flowering plantings that create a sense of privacy. Behind the house, a new bluestone terrace provides another beautifully appointed outdoor setting, framed by river stone pea gravel and the surrounding landscape. New exterior lighting, doors, gutters, landscaping, and architectural details complete the extensive exterior improvements. The septic system was inspected, approved to be in excellent condition, and pumped prior to construction. The location is equally compelling. Set in the heart of the Hudson Valley, Sunset House is walking distance to Germantown with easy access to the restaurants, galleries, shops, and cultural life of Hudson, Tivoli, and Rhinebeck. It is a rare setting that offers true privacy and panoramic country views without giving up proximity to some of the region's most sought-after destinations. Sunset House is a fully realized country retreat--private, architectural, beautifully appointed, and completely connected to its extraordinary setting. A place for long summer days by the pool, dinners that stretch into the evening, and sunsets that never get old.

180 Hilltop Road, Germantown
$1,995,000
3 Beds ⋅ 3 Baths ⋅ 1032384 MLS
Set on eight private acres just outside the Village of Germantown, 150 Round Top Road is a thoughtfully designed contemporary home that blends seamlessly with its quiet, wooded surroundings. Built in 2023, the home is clad in cypress wood and natural stone and features a heated in ground pool, perfect for summertime. Inside, soaring 12 foot ceilings and ample windows allow natural light to illuminate the home, especially the open kitchen and upstairs living space. Anchored by a floor to ceiling Venetian stucco fireplace, the upstairs living space opens onto the oversized kitchen, with painted slab cabinetry, walnut accents, quartz countertops, and generous space for cooking, gathering and entertaining. The deck, located off the great room, is perched among the surrounding trees, integrating the home with its beautiful setting. The primary suite is also on this level, with a walk-in closet and an en-suite bathroom with an oversized, walk-in shower and radiant heat. Two additional bedrooms finish out the the upper level, each with considerable closet space and views of the surrounding forest. A full bathroom with a combination tub/shower and radiant heat sits between these two bedrooms, and solid white oak floors gleam throughout this level. Downstairs, a fully finished walkout lower level adds significant flexibility. This space is currently configured for multiple purposes, functioning as additional seating for large gatherings, a hangout spot for movie night, and a recreation area with plenty of room for ping pong! There is also a dedicated gym on this level, with a window overlooking the backyard and pool, as well as a third bathroom. For added convenience, the integrated 2-car garage opens into this level of the home, with a tiled mudroom ideal for everything from rainy days to snowy boots. Outside, the fenced backyard opens onto the deck, hardscape patio and heated pool, all enjoying a lush and private setting perfect for long days spent outdoors. The backyard is also an ideal entertaining space, with plenty of room for outdoor furniture and grill nights. A lighted, meandering driveway and no road visibility make the setting feel especially private and secluded. Located just minutes from the Village of Germantown, you’ll be within easy reach of favorites like Nines and Universal Cafe. Tivoli, Red Hook and Hudson are also all nearby, with plentiful shopping and dining options. Local breweries like Lasting Joy and Suarez Family are also close. With approximately 3,500 square feet of finished living space, new construction, and more than eight acres of property, 150 Round Top Road offers the ease of a spacious and turnkey contemporary home in a private, desirable location.

150 Round Top Road, Germantown
$2,150,000
3 Beds ⋅ 3 Baths ⋅ 995720 MLS
Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches - all to take in the beautiful Catskills. Stepping through the front door of a wide covered front porch, you'll find an open plan kitchen, dining & living room - the heart of the home, made cozy in winter by an efficient wood stove. The first floor also includes a mud room, office, powder room, laundry room and den. However, it is the 600 sq ft ''Great Room'', with windows on 3 sides that immerse you in the ever-shifting displays of nature and the Catskill range. Upstairs you'll find 3 generous sized bedrooms and 2 full baths including a primary suite with walk-in closet room. The pond, designed by famed UK pool master Anthony Archer-Wills, provides an unparalleled natural swimming experience, set among a chorus of frogs and dragonfly's dancing across the water. A variety of colorful waterlilies and other pond plantings keep the water fresh and inviting. Renovated throughout in 2024-2025, this solar powered home offers you privacy, comfort and jaw dropping sunsets. Conveniently located 10 minutes from Chatham, 30 minutes to the train in Hudson, 40 minutes to the Albany Airport and 25 minutes to Great Barrington & all the culture and fun that our neighboring Berkshires offer. Broker Owned.

53 May Lane, Chatham
$2,395,000
4 Beds ⋅ 5 Baths ⋅ 995945 MLS
Do you want a house which takes care of you, or do you want to take care of a house? If it's the former, then come to 397 Viewmont, Germantown, a newly completed 4-bedroom, 4.5-bath home with 4,100 square feet of above-grade living space, plus 1,100 square feet of finished lower-level space, on 6.86 private acres. Everything is new, including the systems, finishes, and appliances. Designed by a Hudson Valley artist, the house has a classically proportioned exterior with a nod to historic Hudson Valley architecture, but inside it feels open, airy, and full of light. At the center of the house is a dramatic great room with 30-foot cathedral ceilings, an upper-level loft overlooking the room, and a three-tiered south-facing wall of windows. Natural light comes in throughout the day, and a fireplace makes the large room still feel warm and comfortable. The chef's kitchen was designed for real use as much as for entertaining, with Sub-Zero refrigeration, a Miele induction range, two dishwashers, a second refrigerator, a microwave drawer, and a wet bar with an under-counter beverage cooler. The bathrooms are equally generous, including two soaking tubs and an 11-foot double shower. The first-floor primary suite includes two walk-in closets and an oversized bath, while a large laundry and mudroom add everyday convenience. The lower level adds close to 1,100 square feet of open space with oak floors, easily suited for a media room, gym, office, studio, or guest overflow. Subject to town approvals and buyer verification, the property may also offer two-family potential. Geothermal Heating and cooling, abundant natural light, and an all-electric setup mean the house lives comfortably and efficiently, with no Fossil Fuels used for heating or cooling. Set just two hours north of New York City in historic Germantown, the home is 15 minutes from Amtrak in Hudson and about 20 minutes from Rhinebeck. Private but not remote, substantial without feeling overwhelming, this is a truly turnkey Germantown house that offers space, light, comfort, and proximity to town without the burden of a project. Make it your home, where you can enjoy nature, create, write, rest, garden, gather, and more.

397 Viewmont Road, Germantown
$2,550,000
4 Beds ⋅ 4 Baths ⋅ 922554 MLS
All of the charm of an old farmhouse with none of the headaches. This c2005 build has sweeping views of the Catskill Mountains and loads of charm. Down a long, tree lined driveway, you’re just two minutes from the historic hamlet of Germantown but you feel like you’re in a world of your own. Peaceful, private and quiet, 336 Main Street truly offers the best of both worlds. Rocking chairs line the porch to watch the show as the sun sets over the mountains, a fire pit sits in the yard and hammocks hang in the trees. The eight acres have been beautifully landscaped with low maintenance, perennial gardens, and the rolling green lawn brings your eye to the mountains. A bucolic view, the only building in sight is a church steeple in the distance. Inside, you’ll find high ceilings and walls of windows and glass doors to let the outside in— the house was truly built to frame the view. The chef’s kitchen is an absolute dream with a large island, a Sub Zero refrigerator, Viking gas range, two sinks and two dishwashers. A screened in porch runs the length of the house, perfect for entertaining, while there are quiet sitting rooms and an office tucked off to the side with dreamy views of the landscape and mountains. Upstairs there are three bedrooms, all ensuite. The primary has a private balcony & a large bathroom with a double vanity, a soaking tub and a large walk-in shower. The third floor has been built out with bunk beds, perfect for overflow or a place to park the kids. 336 Main is the ultimate in country living— it leaves no stone unturned with its modern conveniences, old world charm, and those quintessential Hudson Valley pastoral views. Just 10m to Hudson & Amtrak, 15m to Rhinebeck village and 2h north of NYC.

336 Main Street, Germantown
$2,795,000
4 Beds ⋅ 5 Baths ⋅ 1025867 MLS
Welcome to Sutherland Estate, a private country compound set on more than 56 acres of rolling meadows, gardens, ponds, with Catskill Mountain views. A long paved drive leads to this elegantly designed 5,760-square-foot home, inspired by classic Greek Revival architecture and recently renovated from top to bottom with refined, high-end craftsmanship. The home features a standing-seam metal roof, radiant heated bathroom floors, energy-efficient heat pumps, a whole-home generator, and a fully integrated smart home system for lighting, temperature, and security. Recent upgrades include newly refinished white oak hardwood floors, new luxury vinyl plank basement flooring, a refreshed lighting plan with recessed fixtures and designer pieces from Arteriors and Hinkley, updated Lutron switches and outlets, new HVAC registers and vents, fresh paint, new baseboards, and updated hardware. The main level offers bright, connected gathering spaces with sweeping views of the ponds and Catskill Mountains. Living and dining rooms flow together, anchored by a beautifully appointed kitchen with a large custom island, a counter-depth panelized Sub Zero fridge, and professional-grade appliances. French doors open to a wide stone patio with an outdoor BBQ, framed by landscaped gardens and open lawns. A paneled cherry wood office/library with built-in cabinetry and a wood-burning stove sits beside a three-season sunroom overlooking the pond, while a spacious living room with a gas fireplace completes the main floor. Upstairs, the primary suite offers a private retreat with a gas fireplace, two walk-in closets, and a luxurious bathroom with soaking tub and steam shower; three additional bedrooms, a guest media room, two full bathrooms with updated quartz-top vanities and faucets, and a laundry room complete the second floor. The finished lower level adds a kitchenette, sauna, and full bath with new LVP flooring, ideal for guests or wellness use. An attached three-car heated garage offers additional space for storage. Outdoors, a footbridge crosses the aerated pond, and the grounds include raised-bed gardens, a potting shed, and a newly built, insulated 26x34-foot carriage house offering space for vehicles, a barn, or future ADU conversion. Located minutes from both Chatham and Kinderhook villages, Sutherland Estate offers refined, move-in-ready country living in beautiful Columbia County.

189 Sutherland Road, Chatham
$3,500,000
5 Beds ⋅ 4 Baths ⋅ 1025502 MLS
Just imagine leaving the city behind and arriving somewhere that immediately feels different. There is a reason the idea of “Eden” has endured for so long. It represents something simple. Something natural. A place where everything feels more balanced, more open, and more your own. Set on a generous parcel with scenic Hudson River views, this property captures that same feeling. Space. Privacy. A quiet sense of separation from everything that does not matter. From the moment you enter the long, tree lined drive, there is a shift. The noise fades. The pace slows. The environment changes. The setting is what defines it. Elevated and surrounded by protected land, the property offers Hudson River views, most notably from the main living space, where oversized windows frame the landscape in a way that feels connected to the home. The residence offers a spacious layout currently configured as four bedrooms, with the flexibility to create a fifth bedroom if desired, along with multiple living areas designed to bring in natural light, views, and everyday comfort. Multiple heating zones allow each area of the home to be controlled independently, creating flexibility throughout the seasons. The land itself expands what is possible. Open, usable acreage provides the opportunity for a pool, outdoor entertaining, or future expansion. A second home on the property, along with an additional structure, creates the potential for guest space or additional uses of the property. Wooded areas of the property offer additional privacy and the potential to create private walking paths throughout the landscape. And then there are the details that are harder to replicate. A private pond set into the landscape. Natural surroundings that preserve long term privacy. A setting that evolves with the seasons, from open summer days to quiet winter mornings. This is not just about what the property is. It is about why it matters. A place to step away when you want to. A place that gives you space without compromise. A place that feels increasingly rare. Eden. The Sunset Escape.

32 Sunset Circle, Germantown
$3,595,000
6 Beds ⋅ 5 Baths ⋅ 919651 MLS
A rare offering of scale, privacy, and refinement, Bellavista Country Estate is a magnificent 12,000-square-foot Georgian brick residence set on over 25 secluded acres in the foothills of the Berkshires, perfectly positioned between the Hudson River Valley and the Berkshires. Designed for elegant country living at the highest level, the estate offers six to nine beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, a fully equipped eat-in kitchen, and a gracious formal dining room—an exceptional blend of timeless architecture and modern luxury. The grounds are equally compelling, featuring a spacious in-ground pool, a tranquil pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, amenities rival those of a private resort, with a full gym, game and entertainment room, home theater, and a refined library creating an environment of comfort, recreation, and retreat. A finished attic and an impressive 4,500-square-foot barn with foosball and ping pong provide additional flexible space for leisure and gathering. Fiber-optic internet and a full-house generator ensure seamless modern living, while the estate's thoughtful infrastructure and meticulous maintenance support effortless year-round ownership. Bellavista stands as a premier private estate, offering a rare combination of total privacy, exceptional amenities, and enduring quality. Just minutes from Chatham, Hudson, and Kinderhook—and a short drive to Lenox, Stockbridge, and Great Barrington—the property is surrounded by acclaimed farm-to-table dining, art galleries, organic markets, and the historic Crandell Theater. Easily accessible via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, and Albany International Airport, Bellavista is as convenient as it is extraordinary.

147 Rock City Road, Chatham
$3,600,000
5 Beds ⋅ 6 Baths ⋅ 1009156 MLS
Presiding over 27 acres of rolling hills, meadows, and dramatic mountain views, Southview Farm is a fully reimagined country estate in the heart of Hillsdale farm country. Once part of a 300-acre dairy farm with a grand farmhouse on this site for over a century, the property has been expanded and rebuilt from the ground up to deliver modern luxury, efficiency, and comfort while honoring its historic character. Facing due south on a quiet country road, the residence overlooks a one-acre, 14-foot-deep spring-fed pond with sweeping vistas to Catamount Ski Area, the Taconic Ridge, and the distant Berkshires. The landscape is so cinematic that scenes from Ang Lee's "Taking Woodstock" were filmed here, evoking the setting of the iconic music festival. The headwaters of the Roeliff Jansen Kill form the eastern boundary of the property, tying the land directly to the scenic Hudson Valley as it winds through Columbia County countryside to the Hudson River itself. The main house offers over 5,000 square feet of living space with four bedrooms and five-and-a-half baths. The ground floor centers on the original stair hall and an expansive chef's kitchen with an 18-foot L-shaped island, soapstone countertops, double sinks, Wolf 48" dual-fuel range with convection microwave, and 42" Sub-Zero refrigerator. A relocated wood-burning fireplace, rebuilt with original farmhouse brick, anchors this warm gathering space. Off the kitchen, a bright butler's pantry/mudroom opens toward a sunroom wrapped in oversized windows and warmed by a wood stove, ideal for four-season enjoyment of the views. Opposite the kitchen, the generous living room features the second wood-burning fireplace and picture-perfect views of both the mountains and the wildflower meadow and pool area. A main-level bedroom suite offers a private wing with a refined en-suite bath and custom walk-in closet. Upstairs, the second floor includes additional bedrooms, a den, office, and laundry room. The third floor is a dramatic open space with cathedral ceilings, currently used as a gym and sitting area, easily adaptable to create two more bedrooms with en-suite baths if desired. Throughout the home, hardwood floors with radiant heat, centralized cooling, and expansive windows create a light-filled, comfortable environment. All systems are new, including 400-amp electrical service with standby Generac generator, new plumbing and well with whole-house filtration and softener, and a whole-house ERV fresh air and dehumidification system. Restored full-length front and rear porches provide covered outdoor living and frame the panoramic views. Across the parking court, a finely crafted Hennin Post & Beam barn from Woolwich, Maine, offers approximately 1,800 square feet of additional space. The two-story, 38' x 36' structure features eastern white pine framing and interior walls milled from trees on the property. The upper level serves as a guest suite with kitchenette, laundry, and full bath; the lower level is a heated woodshop that could easily be converted to a four-car garage. The barn is weather tight with structural insulated panels, fitted with Marvin windows, and equipped with in-floor radiant heat on the first floor and hot water radiators, air conditioning, and ceiling fans upstairs. A separate pole barn on the property provides storage for equipment, tools, and firewood. Gracious outdoor living centers on the 40' x 18' heated gunite pool with Pebble Tec finish, automatic cover, auto-fill, and bluestone surround, set against a backdrop of native wildflower fields that shift in color from spring through fall. The home and grounds exude a sense of quiet luxury and privacy that celebrates the exquisite setting. Impeccably maintained and thoughtfully upgraded, Southview Farm offers turnkey country living where the Hudson Valley meets the Berkshires, with the conveniences of Hillsdale village nearby and easy access to Hudson, Great Barrington, skiing, and hiking.

335 Dawson Road, Hillsdale
$3,885,000
5 Beds ⋅ 6 Baths ⋅ 937843 MLS
Public Remarks: Built in 1887 in the Aesthetic Movement Style, this red brick building commands the center of Warren Street in the heart of Hudson. The exterior features extensive ornamental terra-cotta panels and trim. The historic interior retains elaborate wood beam ceilings with richly paneled rooms, oak and cherry fireplace mantles and intricate parquet floors. Originally the private residence Hudson brewer Robert Evans of the Evans Brewing Company.. A free-standing building is rare in Hudson; it commands an air of sophistication and private elegance. Windows on all four sides provide excellent sunlight into the interior throughout the day. The house was sensitively reorganized in 1940 into six suites: two office suites on the first floor and four residential suites on the second and third floors. In 2018 a careful, architect directed, restoration of the historic interior woodwork and decorative features also included the restoration of exterior masonry, historic windows and doors, and the addition of a new rear porch. The 2018 renovation provided new mechanical, electrical, data, and plumbing systems for the entire building. Each of the six suites has its own dedicated high efficiency heating and cooling system. Residential suites have new kitchens, bathrooms, washers, dryers, and dedicated water heaters. The office suites have dedicated bathrooms and office kitchens. One office suite is ADA compliant. Each suite is individually metered for electric, natural gas and fiber optic services. The basement is finished, full height with generous windows, conditioned and has exterior access. Each suite has an interior arrangement of rooms with windows providing three exposures: front, side, and rear. The distinctive three-story tower creates interior bay windows with commanding views up and down Warren Street. The main building entrances provide direct access to Warren Street, and the rear entrances thru a lovely small, fenced courtyard to the six on-site parking spaces with alley access. The history and restoration of the Robert Evans Residence make it ideally suited to create a variety of residential and work arrangements. Units could be combined to create a generous owner-occupied suite while still maintaining income producing office and apartment suites. Come have a look.

420 Warren, Hudson
$3,995,000
6 Beds ⋅ 5 Baths ⋅ 991875 MLS
CEDAR HILL - Architectural Country Living at its Finest - is the embodiment of 21st-century modern luxury. Elevated on 10 private acres with sweeping mountain views, a gracious mix of open and wooded landscape, a serene spring-fed lily pond, and an organic vegetable garden, this newly expanded and reimagined six-bedroom home is set in Old Chatham, one of the most coveted corners of New York’s historic Hudson Valley. The home engages seamlessly with its natural surroundings through walls of glass that draw in the changing seasons - from spring’s first blooms and summer’s golden light to autumn’s rich palette and the quiet beauty of snow-covered peaks. Abundant natural light and warm finishes create interiors that balance architectural precision with a sense of comfort and ease. The grounds include a 50-foot heated in-ground Gunite salt-water pool and spa, surrounded by expansive bluestone patios. Thoughtfully positioned just beyond, a cedar-clad spa pavilion - with sauna and custom sleek stainless hot tub - is connected to the house by a breezeway, creates a natural extension of the home while preserving a sense of privacy. Southern light fills this entire setting throughout the day, enhancing both the interiors and outdoor living spaces. A deco-turf night-lit tennis court built by a premier tennis contractor in the Berkshires complete the private, resort-like atmosphere, ideal for restorative retreats, entertaining, or quiet relaxation. The formal living room, with soaring 22-foot ceilings, anchored by a wood-burning fireplace flows effortlessly into a gracious dining area, an open kitchen and butler’s pantry and a secondary gathering room with its own wood-burning fireplace. A game and media room opens directly to the pool terrace, while the main level also offers a first-floor bedroom, full plus half- bath, along with a beautifully designed mudroom with breezeway access. Upstairs, the primary suite serves as a private sanctuary, with glass doors opening to a deck that captures mountain vistas with south and west exposures. Four additional bedrooms, bathroom, a flexible-use room with grand terrace, and a second laundry provide ample space for guests, work and wellness. The property, rebuilt and expanded over a multi-year renovation, was completed in 2023. Designed for year-round, sustainable modern living. Solar power, radiant heated interiors, a three-car heated garage, and multiple EV charging stations ensure comfort and efficiency in every season. Underground utilities further enhance the natural setting. Surrounded by the natural beauty of the Hudson Valley and the Berkshires, Cedar Hill offers access to hiking, skiing, farm-to-table dining, and cultural destinations - while remaining a peaceful retreat to relax and recharge.

33 Ford Road, Chatham
$7,995,000
8 Beds ⋅ 10 Baths ⋅ 929847 MLS
Where History Breathes and Beauty Dwells: WHITE BRIDGE FARM c1775 Welcome to White Bridge Farm, an exquisite historic18th century estate restored and designed honoring and preserving the history with imagination and perfection. White Bridge Farm will take your breath away at every turn from the original restored iron main gate to magical stonewalls, pathways and gardens landscaped to intrigue all your senses with three miles of trails to the magic in all her structures. Pause at sitting areas overlooking the stream, the waterfall and fields with fountains and fire-pits and decorative arbors found throughout this160-acre sanctuary. The 1700's main home, with enchanting courtyard, interior and exterior original and authentic details is comprised of three bedrooms, formal living and dining rooms each with wood burning fireplace, the masterful kitchen, office, mudroom and four full baths and one-half bath. The main level primary en-suite with double height ceiling, wood burning fireplace and master bath is stunning. Upstairs you will find two sunlit en-suite bedrooms and an inviting sitting area. The roof is of handcrafted "dog-ear" copper tiling. All other buildings have copper standing seam roofing. The air is central, and floors are radiant, as in all living structures. The Barn complex creates a delightful courtyard comprised of two guest suites flanked by two magnificent barns. The main level ‘Bridle Suite', with flagstone flooring on the main level is an intriguing open concept space with original stall walls retained to define the spaces opening to brick patio. Above, the light-filled three bedroom ‘Hayloft Suite’ with restored wood flooring has open dining, three bedrooms and lounging terrace. Each suite has Big Chill appliances, WBFP, radiant flooring and W/D. The Barns: the "Horse Barn', has original cobblestone floors and completely restored. The stalls are intact and decorated as living spaces for gathering and bath with shower and copper tub with Lillie Herbeau filter. Upstairs is open space with soaring ceilings to dance, dream and create. The "Gathering Barn" completely restored with soaring ceilings and all original beams and intact stalls originally for hunting dogs decorated as living spaces and grand open spaces for gathering is truly incredible. Attached is a four bay garage with original barn doors, radiant floors and custom storage. The pool house with floor to ceiling stone wood burning fireplace and soaring ceiling highlighting architectural trusses is fabulous, as are the kitchen and bath. French doors open to the custom gunite pool with seating area designed to take in the views and surrounded by gracious plantings and gardens with bluestone decking, pergola, hot tub and stone shower. The systems throughout the property are as spectacular. A magical property for a lifetime of memories. Truly a sanctuary to be marveled.

47 White Bridge Rd, Chatham
$9,950,000
4 Beds ⋅ 6 Baths ⋅ 1026597 MLS
Introducing Pierce Peak, an extraordinary estate set on 31+ acres of private mountaintop where the Hudson Valley meets the Berkshires. Designed by acclaimed architects Burr & McCallum, the 6,000-plus-square-foot residence crowns Cunningham Hill, commanding 360-degree views across the New York and Massachusetts countryside. A dramatic 300-foot roofline stretches across the landscape, interrupted only by an infinity-edge pool that appears to merge with the horizon. Inside the main residence, walls of glass fill the open-concept interior with natural light while framing the surrounding mountains and countryside from nearly every room. The great room and screened three-season porch each feature dramatic cathedral ceilings defined by substantial exposed timber beams and fireplaces. The main residence includes a gourmet kitchen and pantry and two primary suites, while the guest house offers two additional bedrooms. Together, the estate offers four bedrooms and three full and three half baths. A dedicated fitness center and pool house complete the living and recreational spaces. Geothermal heating and cooling complement the home's thoughtful design, while a covered courtyard leads to the garage discreetly integrated beneath the residence. Beyond the residence, the estate unfolds into a complete equestrian setting with an impressive covered riding arena, a five-stall barn with tack room, fenced paddocks, and open pasture. Ideally positioned between the Hudson Valley and Berkshires, Pierce Peak is approximately eight minutes from Queechy Lake, 13 minutes from West Stockbridge, and 20 minutes from Chatham, placing celebrated dining, shopping, culture, and outdoor recreation within effortless reach.

241 Cunningham Hill Road, Canaan
$21,000,000
5 Beds ⋅ 7 Baths ⋅ 1040841 MLS
There are beautiful homes in the Hudson Valley, and then there are properties that seem to occupy a world entirely their own. Set at one of the most extraordinary vantage points in the region, this exceptional contemporary estate presides over 135 private acres with sweeping, unobstructed views across the Hudson Valley to the Catskill Mountains. The sense of scale is remarkable: open sky, rolling land, distant mountains, and complete privacy in every direction—yet Hudson and Great Barrington are each only 25 minutes away. The residence was designed around this landscape; dramatic walls of glass frame the Catskills throughout the house, while soaring ceilings and expansive, open living spaces give the interiors a sense of volume without sacrificing warmth. Living, dining, and kitchen spaces unfold effortlessly toward the terrace and infinity pool, where the water appears to disappear into the mountains beyond. The entire home lives on a single level, an increasingly rare luxury at this scale. Two primary suites and three additional ensuite bedrooms create five beautifully private bedroom suites, equally suited to intimate everyday living or a house full of family and friends. Throughout, the architecture is sophisticated but restrained, allowing the extraordinary setting to remain the focus. And the house is only the beginning. The estate encompasses 135 acres of lawns, fields, woods, and private trails, creating a property that can be experienced as much as admired. A large, crystal-clear swimming pond offers an idyllic counterpoint to the infinity pool. Miles of trails wind through the acreage for riding, hiking, and exploring, while a barn and riding arena establish the property as a true equestrian retreat. A separate two-bedroom cottage provides charming guest accommodations, while a carriage house with its own apartment creates additional flexibility for guests, staff, an office, or studio. What ultimately distinguishes this property, however, is something photographs and specifications can only begin to convey: the feeling of being here. Morning light moving across 135 private acres. Long afternoons by the pond. Horses on the trails. Dinner overlooking the mountains. And, each evening, the sun setting behind the Catskills from an infinity pool seemingly suspended above the Hudson Valley. It is extraordinarily private without being isolated, grand without being ostentatious, and remarkably complete without feeling overdone. Properties of this caliber are exceedingly difficult to create—and even harder to find. Just 25 minutes from the restaurants, galleries, shops, and cultural life, this is not simply a country house. It is one of those rare places that makes leaving the city feel like arriving somewhere else entirely.

21 Schoolhouse Road, Hillsdale
$90,000,000
4 Beds ⋅ 5 Baths ⋅ 922447 MLS
For the first time in history, Mill Farm — Spanning more than 2,000 contiguous acres in Ancramdale, New York, — is being offered to the market. Almost all of the farm is surrounded by thousands of acres of adjacent protected conservation land, making it the only 2,000-acre working farm in the region, ensuring a level of privacy and ecological integrity that cannot be duplicated. Steeped in history, The Mill House dates back to the Revolutionary War era and the Livingston family, and is the conversion of the famed Grist Mill “Defiance,” a rare surviving landmark of early American industry that established the region’s first foundation of commerce. At its core is the Mill House, an approximately 5,600-square-foot architectural treasure set directly on the Punch Brook Stream, where the water flows through the home itself to power its historic hydro turbine mill system. There is a waterfall set close to the Mill House that is an ever present living feature of the environs, as it is closely visible from nearly every room. Adjacent, the former Mill Keeper’s House has been reimagined as a private movie theatre, blending centuries-old character with modern indulgence. Crest Lane, an approximately 3,500-square-foot masterpiece, stands as a second architectural jewel, featuring a windowed living room with sweeping views across the valley. Beyond these primary residences, the property includes 8 single-family homes, including four newly renovated cottages, each on its own deeded parcel, offering unmatched flexibility for family, guests, or future investment. The two main residences, the Mill House and Crest Lane, are connected by a three-mile internal gravel road system. The land itself is a defining asset. This is arguably the largest working farm within two hours of New York City, with organic-certified hay production, fertile valley floors, and rising elevations to both the east and west that frame extraordinary views. Rare 18th-century barns, including a remarkable Dutch Barn, stand as enduring testaments to America’s agrarian history. An active windmill system still feeds water to various points across the farm, while aquifers and tributaries ensure abundant water availability. Recreational and ecological value are equally profound. The farm contains more than 18 miles of perfected, drivable trails that interconnect every corner of the property, creating a network for horse riding, exploration, and access to resources. Three miles of the untouched Punch Brook, a designated New York State trout stream, run through the property—a pristine waterway under private stewardship. The farm is also home to documented bobcat habitats and study areas in partnership with Panthera.org. Its eastern boundary adjoins a vast conservation bird sanctuary, ensuring uninterrupted natural surroundings and extending the feeling of total seclusion for thousands of acres in every direction. Mill Farm uniquely combines agricultural productivity, historical resonance, and ecological significance. With its unmatched scale, legacy, and proximity to New York City, it represents an opportunity that exists nowhere else in the Northeast — a living landmark, never before available on the open market.

281 County Route 3, Ancramdale

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