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$392,500
2 Beds 2 Baths 1030579 MLS
Colonial Home on a Beautiful Country Parcel with New Garage Nestled on a peaceful country road, this charming two-bedroom Colonial offers the perfect blend of privacy, comfort, and convenience. Set back from the road on a beautiful parcel, the home welcomes you into a bright, open-concept living and dining area filled with natural light and complemented by attractive hardwood floors. The galley-style kitchen features stainless steel appliances, making meal preparation and entertaining effortless. Enjoy dinner in the adjoining dining area, relax in the inviting three-season sunroom, or step outside to the spacious rear deck to soak in the surrounding countryside. The first floor also offers the convenience of a full bathroom and laundry area. Upstairs, you'll find two generously sized bedrooms, including a spacious primary suite complete with a walk-in closet and private full bath. A standout feature of the property is the newly constructed two-bay garage, already equipped with electricity and plumbing, making it ideal for a workshop, hobby space, or future expansion. The unfinished second level provides a blank canvas for a studio, home office, guest space, or whatever the next owner envisions. A large rear patio offers the perfect place to enjoy your morning coffee while overlooking the expansive fenced backyard, ideal outdoor gatherings. While offering the tranquility of country living, this home is conveniently located just two hours from New York City. Enjoy easy access to the charming towns of Hudson, Rhinebeck, and Catskill, where you'll find exceptional shopping, dining, entertainment, and cultural attractions. Outdoor enthusiasts will appreciate the nearby hiking trails at Stissing Mountain, boating and fishing on Copake Lake, and skiing at Catamount Mountain Resort or Hunter Mountain during the winter months. Whether you're looking for a full-time residence or a weekend retreat, this inviting property offers the best of the Hudson Valley lifestyle.

155 Pumpkin Hollow Road N, Hillsdale

$2,750,000
4 Beds 5 Baths 1029665 MLS
SUNSET MEADOW - A rare place where architecture and nature exist in perfect balance... As the the private drive gently climbs through the landscape, a sense of calm settles in. Perfectly sited on over 30 private acres of rolling lawns, flowering gardens, open meadows, and woodlands, this exceptional Kate Johns-designed country residence reveals itself, embracing commanding western Catskill Mountain views, spectacular sunsets, complete privacy, and nature's ever-changing beauty. An expansive front porch welcomes you before you even step inside, hinting at the gracious living spaces beyond, where soaring ceilings, walls of glass, wide-plank floors, and abundant natural light frame breathtaking vistas. Flooded with natural light, gracious living and dining spaces unfold beneath soaring ceilings, where a grand stone fireplace, timeless architectural details, and French doors opening to the stone patio create an atmosphere that is both elegant and inviting. Nearly every room enjoys breathtaking western Catskill Mountain views. The chef's kitchen is beautifully designed for both the serious and enthusiastic cook, with a generous center island, oversized walk-in pantry, Wolf range, and abundant storage. French doors open to one of the home's most memorable spaces—an expansive bluestone three-season porch overlooking lush gardens, the pool, patio and commanding western Catskill Mountain views. From morning coffee to sunset dinners, it's a space designed to be enjoyed in every season, creating an effortless connection between indoors and out. The private primary wing is a true sanctuary, offering a spacious bedroom, luxurious bath, exceptional walk-in closet, and an adjoining library or home office that easily serves as an additional bedroom. Upstairs, a sitting area connects two private en-suite guest bedrooms, each enjoying those sweeping Western views. In its own separate area, an additional spacious room offers remarkable flexibility as a studio, home office, library, or additional guest bedroom, allowing the home to live comfortably as either a four- or five-bedroom residence with 4½ baths. The finished lower level offers yet another wonderful surprise, designed for entertaining with a recreation room, bar, full bath, and abundant storage. A welcoming mudroom, laundry room, and attached two-car garage make everyday living as effortless as weekends in the country. Outside, lush perennial and wildflower gardens embrace the pool and spa, where monarch butterflies drift from bloom to bloom throughout the summer. A spring-fed swim pond, open meadows, and mature woodlands complete this extraordinary landscape, offering endless opportunities to relax, explore, and enjoy every season. ... A rare place where architecture and nature exist in perfect balance. Sunset Meadow.

60 Blueberry Lane, Austerlitz

$995,000
2 Beds 2 Baths 1030050 MLS
Built by Dutch settlers in 1740 and quietly tucked along one of Claverack's most peaceful country roads, 210 Bate Road is a home that tells the story of the Hudson Valley itself. Set on 4.72 acres of mature trees, rolling lawn, and woodland, it offers an increasingly rare combination of complete privacy and remarkable convenience--just ten minutes from the restaurants, galleries, and shops of Warren Street in Hudson. Over nearly three centuries, the house has evolved with extraordinary care. While its early Dutch structure remains intact, later stewards thoughtfully incorporated architectural elements salvaged from a nearby grand Federal home, layering the house with another chapter of regional history. Elegant mantels, cupboards, doors, windows, and the staircase sit comfortably alongside hand-hewn beams, wide-plank floors, and beautifully weathered brick, creating interiors that feel collected over generations rather than restored all at once. The kitchen and baths have been sensitively renovated, offering modern comfort while remaining entirely sympathetic to the home's historic character. Every improvement feels quiet and intentional, allowing the architecture--and nearly three hundred years of craftsmanship--to remain the focus. Looking toward the future, the home is powered by solar energy serving both the house and barn, with two Tesla Powerwall batteries providing efficient energy storage and resilience without compromising the property's historic character. The living spaces unfold naturally from one another, each with its own distinct sense of warmth. A wood-burning fireplace anchors the living room, while two wood stoves--one welcoming guests in the generous entrance hall and another in the primary bedroom--make the house feel equally inviting throughout the colder months. An office and a soaring artist's studio provide inspiring spaces to work and create, flooded with natural light beneath vaulted ceilings and exposed timber framing. Upstairs, two peaceful bedrooms share a Jack-and-Jill bath, while a second full bath on the main floor offers flexibility for guests. Outside, the landscape is every bit as compelling as the house itself. Loomis Creek meanders through the property, crossed by charming footbridges that lead to woodland walking trails beneath a mature canopy of trees. A fenced garden surrounds the house, while the open meadow offers ample room for a pool or pond should the next owner wish to add one. The property's creative legacy extends beyond the main residence. The antique two-story carriage barn was once the working studio of renowned local artist Stanley Bate, who lived here at the turn of the twentieth century. His original gas-fired kiln remains in the barn today, a remarkable artifact of the property's artistic past and a lasting reminder of the generations of makers who have found inspiration here. The barn continues to offer exceptional space for creative pursuits, workshops, or future possibilities. Homes of this age are rare. Homes that have been so thoughtfully stewarded--where nearly three centuries of history, craftsmanship, artistic legacy, and modern sustainability exist in such quiet harmony--are rarer still. 210 Bate Road is one of those exceptional places that feels both timeless and entirely alive, offering an extraordinary country setting just minutes from the vibrant cultural life of Hudson.

210 Bate Road, Claverack

$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

$749,000
3 Beds 2 Baths 1005033 MLS
This country home is nestled on 8.7 private acres just five miles from the center of Hillsdale, this charming retreat offers the perfect blend of comfort, character, and natural beauty. A meandering driveway winds through the woods, leading to a welcoming cottage-style home surrounded by perennial gardens filled with native ferns and plantings. The inviting covered front porch opens to a spacious bluestone patio, creating an ideal setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Offering approximately 2,040 square feet, the home features three bedrooms and two full bathrooms, with natural woodwork and wide-board Pine floors throughout. At the heart of the home is a beautifully renovated chef's kitchen with a six-burner propane Bertazzoni range, Marble like tile countertops, a porcelain farm sink, wood cabinetry with abundant storage. The kitchen flows seamlessly into the dining area, where a cast-iron wood stove creates a warm and inviting atmosphere for gatherings around a large farmhouse table. The dramatic great room showcases soaring cathedral ceilings with exposed beams and a natural stone wood burning fireplace as its centerpiece, providing a wonderful space for relaxing and entertaining. The light-filled first-floor primary suite offers a peaceful retreat with an ensuite full bathroom. The additional two spacious bedrooms, feature cathedral ceilings, wide-board Pine floors, warm wood walls, and walls of windows that bring the views of the outdoors in. A welcoming front foyer serves as a practical mudroom with built-in bench seating, a coat closet and laundry/storage closet. The attached one-car garage offers ample space for storage and the utility room. The home includes many updates such as the kitchen, bathrooms, electrical service (200 amp), septic system (2020), paved driveway, a high-efficiency on-demand heating and hot water system (2025). Conveniently located near the villages of Hillsdale, Great Barrington, Chatham, and Hudson, and just minutes from Catamount Ski Area, local farms, hiking trails, state parks, and schools, this exceptional property is equally suited as a full-time residence or a peaceful weekend getaway. A must see to fully appreciate this special home. Please see 3D Interactive Floor Plan & Property Tour.

695 Wolf Hill Road, Hillsdale

$650,000
2 Beds 1 Baths 1016385 MLS
Thoughtfully designed with Passive House principles in mind, this beautifully crafted 2023 home proves that sustainability and great design can go hand in hand. Set on five peaceful acres in the rolling hills between Ancram and Copake, this two-bedroom, one-bath retreat was built for exceptional energy efficiency, lasting quality, and a seamless connection to the surrounding landscape. The open-concept living space is flooded with natural light thanks to a dramatic wall of Andersen and Marvin high-efficiency windows and oversized sliding glass doors that blur the line between indoors and out. Warm pine siding and a spacious deck complement the home's clean architectural lines, while the carefully designed airtight building envelope, continuous insulation, and high-performance construction provide year-round comfort with remarkably low energy consumption. Whether you're looking for a full-time residence or a low-maintenance weekend escape, this home offers a rare combination of modern simplicity, thoughtful craftsmanship, and the peace of knowing it was built to stand the test of time. Perfectly positioned to enjoy some of the Hudson Valley and Berkshires' most beloved destinations, you're just minutes from the Harlem Valley Rail Trail for biking and walking, scenic hikes at Taconic State Park, Bash Bish Falls, and Mount Washington State Forest, and only 15 minutes from the iconic Stissing House. Nearby you'll also find local favorites like The Greens at Copake Country Club, The Aviary, Catamount Mountain Resort, farm stands, wineries, and the charming villages of Copake, Millerton, and Hillsdale. Whether your weekends are filled with hiking, skiing, antiquing, or long dinners with friends, this location puts the very best of the region within easy reach, all just over two hours from New York City.

60 Under Mountain Road, Copake

$650,000
3 Beds 3 Baths 1021272 MLS
Escape to your own private retreat where lake living, outdoor adventure, and timeless country charm come together! Just steps from scenic Copake Lake, this property offers access to one of Columbia County's premier recreational destinations. The 410-acre, motorboat-friendly lake is perfect for boating, waterskiing, kayaking, paddleboarding, and excellent fishing, while nearby Copake Country Club features an 18-hole championship golf course and year-round dining. Conveniently located between Hudson and Great Barrington, and just a short drive to Catamount Mountain Resort, the area offers four-season recreation, with the tranquility of your own beautifully landscaped 4.66 acre setting. Inside, this home is rich with warmth and timeless character. The inviting eat-in kitchen features a breakfast bar, abundant cabinetry, and a pantry, creating a functional space that will delight any home chef. Just beyond, the dining area flows seamlessly into the spacious living room where a cozy wood-burning stove, custom built-in bookcases, and decorative wood trim create a welcoming atmosphere for everyday living and entertaining. The bright, glass enclosed sunroom provides the perfect spot for morning coffee, reading, or simply relaxing, while a handily located half bath completes the main level. Upstairs, you'll find three comfortable bedrooms and two full bathrooms. Gleaming hardwood floors span throughout both levels, and an abundance of natural light fills the home, enhancing the attractive appeal. Outside, the detached two-car garage includes automatic door openers and ample room for a workshop, lawn equipment, bicycles, kayaks, and other recreational gear. Above the garage, the second level offers endless possibilities as an artist's studio, home office, fitness room, or hobby space. The grounds are a gardener's dream, filled with thoughtfully designed plantings and peaceful outdoor spaces. Unwind beneath the covered patio and enjoy the serenity of your surroundings. Whether you're searching for a full-time residence or the perfect weekend getaway, this exceptional property offers the ideal balance of privacy, recreation, and convenience—just minutes from the Taconic State Parkway and only 2.5 hours from New York City.

3493 County Route 7, Hillsdale

$1,350,000
3 Beds 3 Baths 1010320 MLS
Perched atop its own private hill on 15.59 acres in the rolling countryside of Austerlitz, this extraordinary post-and-beam home offers something increasingly rare in today's world: complete and total privacy paired with breathtaking long-range views that seem to stretch forever. Hidden from the road and reached by a long winding driveway, the property unfolds like a private retreat, surrounded by nature, open skies, and the peaceful sounds of the countryside. From sunrise to sunset, the ever-changing landscape becomes a living work of art. Watch morning fog drift through the valleys below, enjoy spectacular mountain views throughout the day, and end each evening beneath a canopy of stars so bright you'll feel miles away from everything—yet you're still conveniently located within easy reach of the Hudson Valley's most desirable destinations. The home itself is a classic post-and-beam design that blends warmth, character, and timeless craftsmanship. Inside, the open floor plan creates a welcoming flow for both everyday living and entertaining. At the heart of the home stands an awe-inspiring floor-to-ceiling fieldstone wood-burning fireplace, anchoring the main living space with rustic elegance and serving as a natural gathering place during every season. The soaring ceilings, exposed beams, and beautiful pine floors create an atmosphere that is both grand and inviting. The spacious kitchen, dining, and living areas flow seamlessly together, all designed to capture the surrounding views and natural light. Central air conditioning ensures comfort throughout the warmer months, while the fireplace provides cozy ambiance when the temperatures drop. The primary suite offers a peaceful retreat complete with an en-suite bath and tranquil views of the surrounding landscape. Two additional bedrooms feature vaulted ceilings and share a full bath, creating comfortable accommodations for you and your guests. An additional half bath adds convenience for entertaining. Step outside onto the expansive rear deck and discover one of the property's most remarkable features. Whether you're enjoying your morning coffee as the mountains emerge from the mist, hosting summer gatherings, or simply gazing at the stars on a clear evening, this outdoor space was designed to celebrate the incredible setting. Nature lovers will appreciate the spring-fed swimming pond, perfect for cooling off on warm summer afternoons, while anglers can spend a relaxing Sunday casting a line in the peaceful waters. The property invites a lifestyle connected to the outdoors, where privacy and serenity are part of everyday life. Additional features include durable board-and-batten siding, a metal roof, portable generator hookup, and a large dry basement providing abundant storage space. Properties offering this level of privacy, natural beauty, and unforgettable views are exceptionally difficult to find. This is more than a home—it's a hilltop sanctuary where the mountains, sky, and surrounding landscape become part of your daily life. A place to escape, recharge, and experience the Hudson Valley as it was meant to be enjoyed.

436 Schoolhouse Road Unit #62, Austerlitz

$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

$3,850,000
5 Beds 4 Baths 1017634 MLS
Exceptional Hudson Valley Estate, Where Modern Living Meets Mountain Majesty. The uniqueness of this impressive property begins with its siting. Nineteen acres at the base of Mount Washington, flanked by Taconic State Park to the east and the Harlem Valley Rail Trail to the west, deliver sunrise over the Taconic Range and spectacular sunsets over the Catskills, with open Hudson Valley views. Opportunities for biking, hiking, snowshoeing, skiing, and kayaking abound, surrounded by regular sightings of blue herons, bald eagles, hawks, cardinals, and hummingbirds. This architecturally refined 5,540 sf home offers 5 bedrooms, 2 offices, two five-fixture bathrooms, one three-fixture bathroom, and a powder room--made for entertaining indoors and out, yet equally comfortable for two. The entire interior was redesigned and renovated beginning in 2020. At the heart of the home is a state-of-the-art kitchen featuring a Sub-Zero 36'' refrigerator/freezer, Wolf 6-burner range with griddle and dual ovens, Wolf stainless hood, Miele dishwasher, dual sinks with disposals, quartzite countertops, custom Italian cabinetry, two appliance garages, and a 10' entertaining island. Just steps away, a 50' lap pool and 8'×8' hot tub anchor the outdoor living area. The L-shaped layout of the house allows required pool fencing to run contiguous with the structure, naturally creating a more informal, secured southern end--with pool and garden--and a formal northern end with living and dining rooms. The living room features a soaring vaulted ceiling and an enormous bay window that puts the Catskill view center stage, anchored by a carved limestone fireplace. The expansive primary suite is a private retreat with a gas fireplace, smart bidet toilet, double sinks, soaking tub, and luxurious rain-and-waterfall shower. Four guest bedrooms, two home offices (one perched high atop the house), formal and informal dining rooms, a mudroom, large gym, and two laundry rooms provide both practicality and flexibility for remote work or multigenerational living. The three-car radiant-heated garage is a dream for collectors and hobbyists, with a new polyaspartic floor, granite-topped workstation with sink, and 240V EV outlet. Long-term peace of mind is supported by a whole-house generator, new roof (2024), and Buderus heating oil boiler. Fresh well water is centrally filtered and conditioned, and a residential elevator connects all three levels. Five-zone radiant heat runs throughout the floors--complemented by central air conditioning and blown hydronic heat for year-round efficiency. Additional highlights include two monitored alarm systems, a smart water monitoring system with automatic shut-off, and a private fiber optic internet line.

315 Weed Mine Road, Copake

$745,000
1016157 MLS
Experience the freedom and beauty of country living on this expansive parcel of land with breathtaking rural views in every direction. Offering an abundance of acreage, this property provides endless opportunities for a private estate, farm, equestrian property, recreational retreat, or future investment. Enjoy rolling countryside vistas, wide-open spaces, and the peace and quiet that only a large tract of land can provide. With plenty of room to build, explore, hunt, ride, or simply enjoy nature, this remarkable property offers the privacy, space, and scenic beauty that are becoming increasingly hard to find. Whether you’re looking to create your dream homestead or secure a substantial piece of countryside, this property is a rare opportunity to own a truly impressive stretch of land. Experience the freedom and beauty of country living on this expansive parcel of land atop a mountain with a milelong private road with breathtaking rural views in every direction. Offering an abundance of acreage, this property provides endless opportunities for a private estate, farm, equestrian property, recreational retreat, or future investment. Enjoy rolling countryside vistas, wide-open spaces, and the peace and quiet that only a large tract of land can provide. With plenty of room to build, explore, hunt, ride, or simply enjoy nature, this remarkable property offers the privacy, space, and scenic beauty that are becoming increasingly hard to find. Whether you’re looking to create your dream homestead or secure a substantial piece of countryside, this property is a rare opportunity to own a truly impressive stretch of land. To be sold with adjoining property MLS 1016151.

Mile High Road, Elizaville

$534,000
1016151 MLS
Experience the freedom and beauty of country living on this expansive parcel of land atop a mountain with a mile long private road with breathtaking rural views in every direction. Offering an abundance of acreage, this property provides endless opportunities for a private estate, farm, equestrian property, recreational retreat, or future investment. Enjoy rolling countryside vistas, wide-open spaces, and the peace and quiet that only a large tract of land can provide. With plenty of room to build, explore, hunt, ride, or simply enjoy nature, this remarkable property offers the privacy, space, and scenic beauty that are becoming increasingly hard to find. Whether you’re looking to create your dream homestead or secure a substantial piece of countryside, this property is a rare opportunity to own a truly impressive stretch of land. To be sold with adjoining lot MLS 1016157.

Mile High Road, Elizaville

$1,300,000
3 Beds 2 Baths 1015707 MLS
Welcome to 1100 Harlemville Road, a c.1850 farmhouse set on more than nine bucolic acres with sweeping views across the Taconic Hills. Perched above the road, the property enjoys a sense of privacy and a setting that feels quintessentially upstate. The drive approaches the rear of the home, where a covered porch offers the perfect vantage point to enjoy the landscape. Enter through a mudroom clad with vibrant wallpaper. Checkered tile floors lead to a spacious country kitchen; patterned tin accenting the walls lend character and texture. A generous pantry conceals the refrigerator while providing ample shelving and storage. The kitchen flows seamlessly into the dining room, anchored by a wood-burning stove. Just beyond, a cozy reading room is adorned in geometric wallpaper and opens to the grounds through French doors. Across the foyer, the living room connects to a dedicated office, offering flexibility for work or quiet retreat. Upstairs, a generous landing leads to three bedrooms and a spacious full bath with built-in shelving. Wide-plank floors run throughout the home, lending warmth and charm. Outside, a 600-square-foot barn supports a variety of recreational and creative pursuits, with potential for conversion into a studio, office, or gym. Raised garden beds are ready for summer planting, while a fire pit at the meadow's edge invites long evenings beneath the stars. Perched above Harlemville Hamlet, convenient to the Taconic Pkwy -- 10 minutes to Chatham 20 minutes to Hudson. Two hours to NYC.

1100 Harlemville Road, Ghent

$1,300,000
3 Beds 2 Baths 1015339 MLS
Down a quiet country road is this 1860 farmhouse sits on thirty acres of mature woodland and open rolling lawns leading to a clear swim pond. The property feels deeply rooted in its setting--an authentic country homestead that has evolved thoughtfully over time. A three-building country compound features a farmhouse, a detached 2-car garage, and a purpose-built barn/studio, creating a rare live/work setting The residence retains the warmth, charm and authentic farmhouse character one hopes to find in a house of this era. Sunlight moves through the interiors throughout the day, highlighting the antique wide-plank floors, historic details, and rooms that feel both comfortable and lived-in. This 3 Bedroom, 2 Bath home strikes a rare balance between preservation and practicality creating a natural gathering place through every season. The home is suited to summer living, holiday dinners, quiet winter weekends, and evenings spent around the wood stove after a day outdoors. The spacious deck just off the kitchen provides a perfect vantage point for outdoor dining and relaxing with a view of the pond. The property's mature hardwoods and evergreens circle the landscape creating natural beauty and great privacy. A newer barn/studio lend both beauty and utility, offering numerous possibilities for creative use, it was designed for the hobbiest or for serious creative or commercial work. The building is outfitted with 200-amp electric service, a roll-up door allows easy access for large-scale work, equipment, or vehicles. A separate downstairs space functions equally in a variety of ways as a working studio, fabrication shop, gallery, or flexible commercial use, offering significant potential for income-producing or professional activity. Access to an upstairs loft space could serve as an office or additional storage. The setting feels private and peaceful, yet remains convenient to the areas most beloved destinations for skiing, hiking, dining, and weekend exploration. 286 Manor Rock Road is the kind of property that has become increasingly difficult to find--an antique farmhouse with genuine character, meaningful acreage, and a sense of place that feels distinctly upstate. It is an ideal fit for buyers seeking the quiet and seclusion of the rural countryside with serious working apace in one private address. This is a strong candidate for remote executives, creative professionals, makers/artists or anyone balancing more than one life under one roofline. Private and serene, this property captivates on every level, offering a rare opportunity to own something truly special. Become the next steward of its rich history while shaping its future and creating a legacy of your own.

286 Manor Rock Road, Craryville

$949,900
3 Beds 2 Baths 1011743 MLS
Steeped in Hillsdale’s rich history, this extraordinary property began its life as one of the area’s original grist mills, situated in the area of Hillsdale once known as Murray’s Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as though it has been lifted from the pages of a storybook. A meandering stream, cascading waterfalls, and a picturesque pond create a peaceful backdrop, while the soothing sounds of flowing water provide a constant sense of calm and escape. Designed for both relaxation and entertaining, the grounds offer an array of inviting outdoor spaces. A spacious deck overlooks the stream and waterfalls, multiple fire pits provide gathering spots throughout the property, and a dock perched next to the pond for quiet moments by the water. A charming pond-side retreat offers comfortable indoor and outdoor seating, while a quaint two-story barn/shed creates another idyllic perch from which to enjoy the sound of a nearby waterfall. Additional outbuildings include a historic barn ready for restoration or reinvention, a garage, and a potting shed. Footbridges and walking paths wind throughout the landscape, inviting exploration of the property's natural beauty at every turn. Inside, the home offers generous living space with three bedrooms and two bathrooms, allowing family and guests to spread out comfortably. The second floor sitting area features a cathedral ceiling and overlooks the stream and falls. Historic elements remain throughout, from original floors and woodwork and including an original mill wheel that now lays proudly at the entrance to the rear shed, serving as a reminder of the property's unique past. Despite its remarkably private setting, the property enjoys a convenient location just over a mile from the center of Hillsdale, less than two miles from Catamount Mountain Resort, 15 minutes from Great Barrington, MA, 25 minutes from Hudson, 10 minutes from the Taconic State Parkway, and approximately 2¼ hours from New York City. A rare opportunity to own a piece of Hillsdale history, surrounded by natural beauty, timeless charm, and the soothing presence of water at every turn.

2955 State Route 23, Hillsdale

$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

$4,125,000
998452 MLS
The Philmont Collection presents a rare opportunity to acquire a 36-unit multifamily portfolio encompassing nine buildings across seven tax lots in the heart of Philmont's National Register Historic District. Spanning approximately 26,606 square feet, the collection combines immediate scale, strong in-place cash flow, historic character, and meaningful redevelopment potential within one of the Hudson Valley's most closely watched village investment markets. Strategically clustered within a few walkable blocks of one another, the portfolio includes seven stabilized income-producing assets together with two historic value-add buildings, creating a level of operational efficiency and market presence rarely available in a single acquisition. The collection comprises 36 residential units with 48 bedrooms and 28 bathrooms, offering a diverse mix of apartments and duplex residences that support broad tenant appeal and stable occupancy. The stabilized core portfolio is projected to generate approximately $350,000-$360,000 in annual NOI, providing attractive current returns while preserving opportunities for future value enhancement. Ownership has invested substantially throughout the portfolio in capital improvements, infrastructure upgrades, and operational efficiencies designed to improve long-term performance and reduce operating costs. A cornerstone asset within the collection, 62 Main Street has undergone extensive renovation, including updated residential units, restored facade improvements, enhanced insulation, conversion from central oil heat to individual electric systems, and renovated bathrooms. These improvements, together with portfolio-wide upgrades, position the collection as a well-maintained and professionally operated investment. Current operations utilize the DoorLoop management platform for leasing, maintenance coordination, rent collection, tenant communication, applications, and screening, facilitating a seamless transition for future ownership. The portfolio also includes the historic front and rear buildings at 7 Church Street, presenting a compelling redevelopment opportunity within Philmont's historic core. Subject to purchaser verification and approvals, these buildings may be eligible for substantial federal and New York State historic rehabilitation tax incentives, creating a potentially powerful avenue for future value creation and income growth. Long appreciated for its architectural character and strategic location, Philmont continues to attract investors, entrepreneurs, artists, and designers drawn to its affordability relative to neighboring Hudson, its historic building stock, and its ongoing revitalization. Significant public and private investment, adaptive reuse projects, and preservation initiatives continue to strengthen the village's long-term trajectory. Ideally situated just minutes from the Taconic State Parkway and approximately fifteen minutes from Hudson and Amtrak service to New York City, the portfolio enjoys convenient access to the Berkshires, Hawthorne Valley Farm, Art Omi, hiking trails, skiing, boating, waterfalls, acclaimed dining destinations, and the cultural amenities that define the Hudson Valley lifestyle. Combining immediate income, operational scale, historic character, redevelopment potential, and an extraordinary village-wide footprint, The Philmont Collection represents a truly uncommon opportunity to establish a meaningful position within a growing and increasingly recognized Hudson Valley market. MLS information reflects the primary parcel only. Seller reserves the right to sell individual assets or subsets of assets separately from the portfolio offering. Complete financial statements, rent rolls, parcel information, and supporting materials are available upon request. Annual tax amount reflects the entire portfolio.

7 Canal Street, Claverack

$525,000
5 Beds 2 Baths 1006015 MLS
Welcome to 52 Church Street, a c.1900 home set on a generously-sized quarter acre lot in the Village of Philmont. Enter through a large mudroom flanked with windows. A stylish living room flows seamlessly to a large kitchen overlooking the yard. Numerous windows and a door leading to the backyard flood the kitchen space with light. A hall leads to a second kitchen, bedroom and full bath, perfect for an in-law suite or separate apartment. Upstairs four large bedrooms with generous closet spaces share a full bath. Tasteful wallpaper and decorative finishes combine with hardwood floors to provide charm throughout. Outside, an expansive deck runs the length of the exterior, giving way to a large fenced-in yard. A new hot tub and sauna offer moments of respite while the gas firepit ensures guests will be entertained well into the evening. A separate garage offers off-street parking and additional space suitable for a workshop and / or storage. Numerous updates include — but are not limited to — new appliances in each kitchen, a mini-split heating & cooling system as well as painted interiors & exteriors. Ideally located within walking distance to Philmont village amenities and High Falls Conservation Area, this home is perfectly positioned to enjoy the best of the Hudson Valley. Hudson and Amtrak are just 15 minutes away, with New York City approximately 2.5 hours by car.

52 Church Street, Hudson

$399,000
1005073 MLS
Located in the heart of historic Ancram, this versatile multi-family duplex offers a unique opportunity for investors, owner-occupants, or those seeking a country retreat with income potential. Set on just under an acre along the scenic Roeliff Jansen Kill creek, the property combines charm, character, and a peaceful natural setting. The duplex features two separate living spaces: one side offers a comfortable 2-bedroom, 1-bath layout, while the larger unit includes 4 bedrooms and 2 full bathrooms, providing flexibility for rental income, extended family living, or a live-in investment arrangement. Hardwood floors and original details add warmth and character throughout. Outside, you’ll find a detached one-car garage and a rustic barn overlooking the backyard and creek, creating the perfect backdrop for gardening, recreation, or simply enjoying the sounds of nature. The property offers a blend of historic Hudson Valley charm and practical functionality with room to make updates and add value over time. Conveniently located near Hudson, Millerton, Copake, and the Berkshires, this property provides easy access to farm markets, restaurants, hiking, and outdoor recreation while maintaining the quiet atmosphere that makes Ancram so desirable. Whether you’re looking for an income-producing property, weekend escape, or long-term investment, this duplex is full of potential.

2457 State Route 82, Ancram

$325,000
998490 MLS
Privately tucked away along one of Ancram’s most picturesque country roads, this beautiful approximately 25-acre offering presents a rare opportunity to create a secluded full-time residence or weekend retreat in the heart of the Hudson Valley. Quiet and rural, yet conveniently located just 8 minutes to Pine Plains, 15 minutes to Millerton and Copake, and under 30 minutes to Hudson, Red Hook, and Rhinebeck. The land offers a wonderful blend of rolling woods, hills, and natural beauty, with a stream winding through the property and abundant space for hiking, recreation, hunting, or simply enjoying the privacy of a substantial acreage parcel. A roughed-in drive already meanders through the landscape, following a former logging road that has been partially cleared, and the current owner has begun clearing two potential building sites. Whether envisioned as a full-time home, weekend escape, or multi-home compound, the property offers exceptional flexibility and potential. The offering consists of two parcels, and the acreage and taxes shown reflect both properties combined. Second parcel ID: 103400-213-000-0001-011-000-0000.

Hall Hill Road, Ancram

$649,000
3 Beds 2 Baths 1002222 MLS
On a quiet country road, sit's the prettiest sunshine yellow house you've ever seen. Welcome to a property where outdoor splendor and indoor comfort merge seamlessly, where everything has been taken care of, and all you need to do is arrive and exhale. Rolling hills and open farmland stretch out before you, and they're all yours to enjoy. Inside, the dining room flows into an open kitchen and connects to a three season porch, an effortless setup for entertaining from morning coffee to evening gatherings. A wood burning fireplace anchors the living space, ready for exactly the kind of cozy winter nights you've been dreaming about. The first floor offers a bedroom with en suite bath, and a game room in the basement adds even more flexibility. Upstairs, two generously sized, sun drenched bedrooms complete the main house. And then there's the garage. Converted into a fully self contained one bedroom apartment, a huge picture window frames sweeping views of the surrounding countryside, the kind of view you never tire of. Use it for rental income, a guest suite, a creative studio, or a private retreat . The possibilities are endless. Just moments to Copake Lake, Bash Bish State Park, the Rail Trail, Catamount, the best farmers market, Random Harvest, and Hilltown Hotpies. One of the most idyllic settings in all of Columbia County.

81 Black Grocery Road, Hillsdale

$299,000
996860 MLS
Welcome to DREAMLAND. Set along a quiet country road, this exceptional 22 acre parcel offers the rare combination of privacy, curated natural beauty, and effortless access from New York City. Just minutes from the Taconic State Parkway, the property is ideally positioned for seamless weekend escapes or full-time living. A sun-drenched open meadow—perfectly oriented for southern exposure—creates an ideal setting for a modern country estate, while a network of winding, tree-lined trails invites exploration through a landscape of mature hardwoods, including striking 200-year-old oak trees and historic stone walls. The setting feels both expansive and intimate, a 5 acre building site offering the opportunity to design a home that fully captures the surrounding natural beauty. Located moments from the renowned Hawthorne Valley School and its celebrated farm store, and within easy reach of the cultural richness of the Berkshires, this property places you at the intersection of nature, design, and lifestyle. Skiing, art, and dining are all nearby, while the vibrant riverfront city of Hudson is just 20 minutes away. A rare opportunity to create a legacy property in one of the Hudson Valley’s most sought-after settings—where architecture, landscape, and lifestyle come together seamlessly. BOHA, Driveway permit, survey

County Route 21, Hillsdale

$325,000
3 Beds 2 Baths 998268 MLS
Welcome to Hawthorne Cottage, a circa 1900 updated residence on Main Street in the heart of Philmont's historic district, set on a sloping lot with a stone wall and partial woodland in one of Columbia County's most authentic small villages. The home has been fully renovated. Open shelving and curated details create inviting living spaces full of warmth and character. The kitchen includes butcher block counters, a herringbone tile backsplash, stainless steel appliances, and striking navy cabinetry accented by brushed brass hardware. New laminate floors run through every room and bathrooms have been updated. The cozy layout spans 1,392 square feet, with a half bath on the first floor and three bedrooms and a full bath above. The unfinished walk-out basement adds approximately 360 square feet of flexible additional space, and is ready to be finished to your own specifications. Ideal as a home office, guest quarters, home gym, or creative studio. A brand new heating system completes a renovation that leaves little to do but move in. Philmont is a small Columbia County village with a growing creative community and a genuine historic fabric. Hawthorne Valley School and its beloved farm store are nearby, as is the High Falls Conservation Area, where trails wind through hemlock ravines to Columbia County's highest waterfall. Local 111 and other village favorites are close at hand for dining. Hudson's Warren Street galleries, restaurants, and Amtrak station are eighteen minutes away, Chatham is fifteen minutes, and New York City is two and a half hours by car. The farm stands, hiking trails, and country roads that define life in this part of the valley are all within easy reach.

152 Main Street, Claverack

$1,300,000
4 Beds 3 Baths 991625 MLS
Wildflower Hill is a rare and distinctive country retreat set behind a gated entrance on nearly six private acres in the gently rolling countryside of Southern Columbia County. Tucked behind mature trees and open lawns in the heart of Ancram, this four-bedroom, two-and-a-half-bath residence offers over 3,900 square feet of well-proportioned living space, where reclaimed wood beams, abundant natural light, a striking stone fireplace, and artful architectural details create a home of warmth, character, and timeless style. Designed for relaxed daily living, weekend entertaining, and four-season enjoyment, the interiors unfold through generous living and dining spaces with an easy connection to the outdoors. A large deck overlooks the grounds and extends the home beautifully for summer dinners, visiting guests, and quiet mornings in the country. Recent improvements include a brand-new boiler and brand-new septic system, offering immediate comfort, efficiency, and long-term peace of mind. Outside, the setting is both serene and full of charm. A koi pond, fruit trees, rolling lawns, fenced garden, and light-filled potting shed create a property that feels established, private, and deeply connected to the land. The acreage is beautiful and usable, with room to garden, entertain, explore, or simply enjoy the quiet rhythm of the seasons. Wildflower Hill balances privacy with exceptional access to the region’s most beloved destinations. A short walk leads to the Ancram Little Store for coffee, breakfast, lunch, local cheeses, dairy, teas, and seasonal provisions. Farmers Wife is approximately six minutes away, Hillrock Estate Distillery is approximately nine minutes away, and Stissing House is about thirteen minutes away for celebrated farm-to-table dining. Millerton is roughly fifteen minutes away for restaurants, shopping, The Moviehouse, and Oblong Books, while Mashomack Polo Club, Catamount Mountain Resort, Hudson, Hillsdale, and the Berkshires are all within easy reach. New York City is approximately two hours away. Equally suited as a full-time residence, refined weekend retreat, or year-round lifestyle investment, Wildflower Hill captures the enduring appeal of Hudson Valley living with privacy, character, and a setting worth discovering.

2339 State Route 82, Ancram

$525,000
3 Beds 2 Baths 992789 MLS
Discover the Charm of Country Living Escape to this authentic 3-bedroom, 2-bath log home tucked away on a peaceful private road in Ancram. Set on 5 acres, the property also includes a separate 3-acre buildable lot across the lane—perfect for maintaining privacy, creating a guest house or studio, or simply preserving your view and open space. Start your day with coffee on the front porch, or soak up the sunshine from the back deck. After a crisp autumn afternoon, unwind with a hot drink by the fire. With high-speed, fiber optic internet, you can stream your favorite shows or work remotely while surrounded by nature. Whether your passions lean toward the outdoors, local arts, farm-to-table dining, or simply quiet moments in the beauty of the Taconic Valley, this home offers the best of upstate living—serenity, character, and endless possibilities.

284 Hall Hill Road, Ancram

$195,000
2 Beds 1 Baths 986915 MLS
Set on a generous parcel in a quiet Hudson setting, this property offers a compelling opportunity for those with vision. The surrounding landscape is defined by open lawn, mature trees, and a natural sense of privacy—creating a setting that feels both spacious and serene. The existing home is a single-level residence with a straightforward layout, ready for thoughtful renovation. While the interiors reflect the need for updating, they present a clear canvas for reconfiguration or restoration. The true value lies in the land. The depth of the lot and its natural surroundings offer flexibility for outdoor living, expansion, or simply enjoying the space as a private retreat. There is a sense of openness here that is increasingly difficult to find. Just a short drive from Hudson’s Warren Street—often noted for its design-forward character—this location places you within reach of independent shops, galleries, vintage and antique sourcing, and a well-regarded dining scene rooted in farm-to-table culture. With close proximity to the Catskills, riverfront access, and a community that continues to attract artists and creatives, the area offers a balance of cultural depth and natural surroundings without feeling removed.

280 Route 217, Hudson

$525,000
2 Beds 2 Baths 990020 MLS
Welcome to this charming two-story Colonial set along a scenic road in a quiet, picturesque setting. This turn-key home is filled with character and warmth, featuring wide-plank hardwood floors, exposed wood beams, soaring vaulted ceilings, and a stunning stone wood-burning fireplace that anchors the inviting eat-in kitchen. Thoughtfully updated with solar panels for energy efficiency, the home blends timeless style with modern convenience. Upstairs, the spacious primary suite offers a private retreat complete with a beautifully appointed en suite bath and classic clawfoot tub. A flexible office/den provides the option for a third bedroom, perfect for guests or remote work needs. Step outside to the deck and take in seasonal countryside views—an ideal spot for relaxing or entertaining. Perfect as a full-time residence or weekend escape, this exceptional property also offers easy access to nearby amenities, including scenic trails at Bash Bish Falls and refreshing summer days at nearby Lake Taghkanic State Park. A rare opportunity to enjoy peaceful country living without sacrificing convenience.

17 Rothvoss Road, Ancramdale

$850,000
986731 MLS
Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with the varied topography, these features lend an air of serenity and seclusion. The property is currently enrolled in a forestry program that affords property tax reductions and opportunities for periodic timber revenue. Two distinct building envelopes, each encompassing three to four acres, are excluded from the program, allowing for immediate development while preserving the tax benefits. For those seeking broader vision, the acreage also presents the potential for subdivision, presenting a unique investment opportunity with far-reaching views in a highly desirable region. Ideally positioned at the crossroads of the Hudson Valley and the Berkshires, this exceptional offering combines privacy and natural beauty with access to renowned cultural institutions, fine dining, and year-round outdoor pursuits.

Overlook Drive, Hillsdale

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