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$21,000,000

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.

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

$615,000

Set on 3.28 acres amid the open farmland of Copake, this inviting 1960s farmhouse has the relaxed character of a country house that immediately makes you feel at home. A generous covered porch stretches across the front of the house, overlooking its own open field and the agricultural landscape beyond. Inside, wide-plank pine floors, abundant windows, and natural wood details give the house its easy country character. The living room is centered around a wood-burning stove, with built-in bookshelves and cabinetry adding both charm and function. The adjoining kitchen is bright and thoughtfully laid out, with generous workspace and views onto the surrounding greenery. From there, the house opens into an inviting dining room with wraparound windows that bring the landscape into the room, while doors lead directly outside to an outdoor dining area. Two generously sized bedrooms and a full bath are located on the first floor. Upstairs, the primary bedroom sits beneath vaulted, pine-clad ceilings and includes an en-suite bath and spacious walk-in closet. A large additional room on this level offers plenty of flexibility for a library, studio, office, den, or guest space. Outside, the property unfolds from lawn and established plantings into an open field, with room to garden, play, gather with friends, or simply enjoy the landscape. The front porch is an especially lovely perch for taking it all in, while a rear deck offers a more tucked-away place outdoors. A two-car garage, basement, laundry area, and additional storage round out the property. The location puts some of the best of Columbia County and the Berkshires within easy reach. Copake and Hillsdale are close at hand, with Egremont and Great Barrington just across the Massachusetts border. Catamount, nearby lakes and hiking trails, farm stands, and local markets offer plenty to explore throughout the year, with Hudson an easy drive to the west. Unfussy, comfortable, and surrounded by farmland, this is a house that captures much of what makes this corner of the Hudson Valley so appealing. It offers space to spread out, a close connection to the landscape, and the pleasures of country life.

3 Beds ⋅ 2 Baths ⋅ 1042091 MLS

Set on 3.28 acres amid the open farmland of Copake, this inviting 1960s farmhouse has the relaxed character of a country house that immediately makes you feel at home. A generous covered porch stretches across the front of the house, overlooking its own open field and the agricultural landscape beyond. Inside, wide-plank pine floors, abundant windows, and natural wood details give the house its easy country character. The living room is centered around a wood-burning stove, with built-in bookshelves and cabinetry adding both charm and function. The adjoining kitchen is bright and thoughtfully laid out, with generous workspace and views onto the surrounding greenery. From there, the house opens into an inviting dining room with wraparound windows that bring the landscape into the room, while doors lead directly outside to an outdoor dining area. Two generously sized bedrooms and a full bath are located on the first floor. Upstairs, the primary bedroom sits beneath vaulted, pine-clad ceilings and includes an en-suite bath and spacious walk-in closet. A large additional room on this level offers plenty of flexibility for a library, studio, office, den, or guest space. Outside, the property unfolds from lawn and established plantings into an open field, with room to garden, play, gather with friends, or simply enjoy the landscape. The front porch is an especially lovely perch for taking it all in, while a rear deck offers a more tucked-away place outdoors. A two-car garage, basement, laundry area, and additional storage round out the property. The location puts some of the best of Columbia County and the Berkshires within easy reach. Copake and Hillsdale are close at hand, with Egremont and Great Barrington just across the Massachusetts border. Catamount, nearby lakes and hiking trails, farm stands, and local markets offer plenty to explore throughout the year, with Hudson an easy drive to the west. Unfussy, comfortable, and surrounded by farmland, this is a house that captures much of what makes this corner of the Hudson Valley so appealing. It offers space to spread out, a close connection to the landscape, and the pleasures of country life.

1492 County Route 7A, Copake

$349,500

Experience the benefits of luxury living without the luxury price tag. Nestled in the northern Hudson Valley just minutes from the Taconic State Parkway, 80 Lakeshore Acres offers a rare opportunity to embrace a slower, more beautiful way of life. Set in the charming community of Craryville. Inside, 2 bedrooms, one bathroom and the open-concept layout creates a warm and welcoming space for gathering, while the beautiful bonus room offers the flexibility to become a home office, guest retreat, studio, or simply a quiet place to escape. Thoughtful details include rich cherry wood cabinetry, granite countertops, generous closets, and well-maintained mechanical systems. A two-car garage and plenty of additional parking is available on the property. It also includes three heating options such as electric hot air, a pellet stove, and a Toyotomi kerosene fireplace. You can enjoy the home comfortably throughout the seasons. Step outside and let the beauty unfold. The fenced-in-ground pool, with its inviting pool house, creates a private setting for relaxing, entertaining, and enjoying long summer days. Just a short walk from Copake Lake, the property offers deeded lake access rights coupled with a dock, inviting you to spend your days on the water and take in the surrounding natural beauty. And beyond the property, there is so much to enjoy. Start your morning with a peaceful walk or hike, spend the afternoon by the lake, listen to live music at the marina, or wander through the local farmers market. Golf, playgrounds, a dog park, local dining, and Roe Jan Brewing Company are all nearby. When winter arrives, trade the lake for the slopes at Catamount Mountain Ski Resort. Whether you're looking for a weekend getaway, a full-time residence, or a place to enjoy the beauty of the Hudson Valley, this property offers comfort, outdoor enjoyment, and an ideal setting. This is more than a home. It is a place to create the lifestyle you've been dreaming about.

2 Beds ⋅ 1 Baths ⋅ 1039149 MLS

Experience the benefits of luxury living without the luxury price tag. Nestled in the northern Hudson Valley just minutes from the Taconic State Parkway, 80 Lakeshore Acres offers a rare opportunity to embrace a slower, more beautiful way of life. Set in the charming community of Craryville. Inside, 2 bedrooms, one bathroom and the open-concept layout creates a warm and welcoming space for gathering, while the beautiful bonus room offers the flexibility to become a home office, guest retreat, studio, or simply a quiet place to escape. Thoughtful details include rich cherry wood cabinetry, granite countertops, generous closets, and well-maintained mechanical systems. A two-car garage and plenty of additional parking is available on the property. It also includes three heating options such as electric hot air, a pellet stove, and a Toyotomi kerosene fireplace. You can enjoy the home comfortably throughout the seasons. Step outside and let the beauty unfold. The fenced-in-ground pool, with its inviting pool house, creates a private setting for relaxing, entertaining, and enjoying long summer days. Just a short walk from Copake Lake, the property offers deeded lake access rights coupled with a dock, inviting you to spend your days on the water and take in the surrounding natural beauty. And beyond the property, there is so much to enjoy. Start your morning with a peaceful walk or hike, spend the afternoon by the lake, listen to live music at the marina, or wander through the local farmers market. Golf, playgrounds, a dog park, local dining, and Roe Jan Brewing Company are all nearby. When winter arrives, trade the lake for the slopes at Catamount Mountain Ski Resort. Whether you're looking for a weekend getaway, a full-time residence, or a place to enjoy the beauty of the Hudson Valley, this property offers comfort, outdoor enjoyment, and an ideal setting. This is more than a home. It is a place to create the lifestyle you've been dreaming about.

80 Lake Shore Acres, Craryville

$3,600,000

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.

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

$325,000

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.

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