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$1,200,000
5 Beds 4 Baths 1049616 MLS
Welcome to 156 Farm Road, a rare and versatile multi-residence property offering two completely renovated homes for one price. Set along a quiet country road and surrounded by mature trees, this turnkey property offers privacy, flexibility, and an array of possibilities for an owner-occupant, extended family, guests, or an investment opportunity. The lower residence is a charming two-story farmhouse offering 1,646 square feet with three bedrooms and two full bathrooms. The first floor features a bedroom and full bathroom, while upstairs are two additional bedrooms and a shared full bathroom. A wood-burning fireplace adds warmth and character to the living space. The home also features its own paved driveway, detached garage, fire pit, and partially fenced outdoor area. The upper residence is a 1,400 square-foot ranch, privately situated at the end of a gently winding, sloped driveway and nestled among the trees. Offering two bedrooms and two full bathrooms, the home includes a spacious primary suite, eat-in kitchen, and inviting living area with a wood-burning fireplace. A wraparound deck provides multiple ways to enjoy the peaceful setting, with access from both the main front entrance and the kitchen. The ranch also enjoys its own private backyard, fire pit, and partial fencing for added privacy. Both homes have been completely renovated inside and out, feature electric car chargers, and are fully electric, featuring central air in the upper house, and mini-split heating and cooling systems supplemented by electric baseboard heat in the lower house. Recent exterior improvements include reseeding of the yard, professional tree maintenance, two paved driveways, and additional gravel parking for the upper residence. With two separate residences on one tax lot, the property offers exceptional flexibility. Live in one home while using the other for guests, extended family, or potential rental income, or explore the property as an investment. The thoughtful separation of the two homes allows for privacy while still offering the convenience of a single property. Quiet, private, and completely turnkey, 156 Farm Road is a distinctive opportunity to own two beautifully renovated residences in one peaceful country setting.

156 Farm Road, Copake

$879,000
3 Beds 3 Baths 1048206 MLS
Located on a quiet country cul-de-sac in Hillsdale, this spacious three-bedroom home sits on 4.7 private acres. One of just three residences along the road, it enjoys an exceptionally peaceful setting, with open lawn, well-maintained woods, trails, and old stone walls. Inside, the living space provides generously proportioned rooms and abundant natural light. The living room centers around a stone fireplace, with large windows and direct access to an expansive back deck, ideal for outdoor dining, grilling, or simply enjoying the surroundings. The generously sized kitchen includes a large eat-in area, while a separate dining room offers additional space for gathering. The primary suite is notably spacious, with an en-suite bath featuring a soaking tub and separate shower. Two additional well-sized bedrooms, a second full bath, and a half bath complete the main level. A full walkout lower level spans the footprint of the house, with high ceilings, multiple windows, and French doors leading outside. Currently unfinished, it offers potential for additional living space, a studio, gym, or recreation room. The home also has an attached two-car garage. A separate two-car garage/workshop offers even more flexibility for creative pursuits, projects, or additional storage. For all its privacy, the property is exceptionally well positioned, with the village of Hillsdale, Catamount, and the Harlem Valley Rail Trail all just five minutes away. Copake is also nearby, with both Hudson and Great Barrington within easy reach.

310 Pine Ridge Lane, Hillsdale

$299,000
1 Beds 1 Baths 1048427 MLS
Built in 1807, this charming one-bedroom, one-bath cottage feels like a little piece of history. Recent thoughtful updates have brought comfort and ease to the home while keeping the details and character that make it so special. The main level is open and light filled, with original wide plank floors and exposed beams running through the living and dining space, a nod to the home’s early origins. Just beyond is a home office with French doors that open directly onto the patio, bringing fresh air and garden views into the workday. Upstairs, the lofted bedroom is tucked beneath the roofline, a cozy space with a character all its own. Outside, the partially fenced yard offers plenty of reasons to spend time outdoors, with a fire pit for evenings under the stars. A separate studio is perhaps the property’s most unexpected feature. With its own wood-burning stove, it’s a space for painting, writing, making, or whatever creative pursuit takes hold. With the Hudson Valley and Berkshires both at your fingertips, there’s plenty to do in every direction. Hudson is 20 minutes away, Great Barrington 10 minutes, Millerton 20 minutes and Copake just 5. Ski at Catamount, bike the Harlem Valley Rail Trail, wander through Roeliff Jansen Park and stop by the farmers market, enjoy every season at Bash Bish Falls, or pick up a stretch of the Appalachian Trail. Restaurants, markets, antique shops and local favorites fill the surrounding towns, making it easy to head out without much of a plan and still end up somewhere wonderful.

2779 State Route 23, Hillsdale

$799,900
3 Beds 3 Baths 1048408 MLS
Tucked into the woods on a quiet country road, just a mile from Route 22, 224 Under Mountain Road is the kind of home that makes you slow down, take a breath, and settle in. Surrounded by nature yet wonderfully convenient, this warm and inviting 3-bedroom, 2.5-bath home on 4 acres offers a relaxed country lifestyle with thoughtful updates and spaces designed for everyday living and entertaining. Step inside and you are immediately welcomed by gorgeous wood floors, natural light and a sense of warmth that continues throughout the home. The living room centers around a wood insert fireplace, creating the perfect gathering place on cool evenings. The heart of the house is the incredible chef's kitchen, complete with a generous island and high-BTU gas range--just right for unleashing your inner professional chef. From casual breakfasts to elaborate dinners with friends, this is a kitchen meant to be enjoyed. A proper mudroom provides a practical transition from the outdoors and leads into the inviting family room, where wooden ceiling beams and a wood stove add character and warmth. When the weather cooperates, life naturally moves outdoors to the rear covered, screened-in porch. It is an ideal spot for morning coffee, dinner al fresco, or lingering with friends while listening to the sounds of nature. Here, the distinction between inside and outside seems to disappear. Upstairs, the private primary en-suite bedroom offers a comfortable retreat with its own walk-in shower, while two additional bedrooms and a full hall bath provide plenty of room for family and guests. Recent improvements make this country retreat as comfortable as it is charming, including a new HVAC system (central AC too!), new windows, durable cement siding, and a new rear deck and fire pit area. High-speed internet is on site, making it possible to enjoy the tranquility of the woods without giving up modern connectivity. A full basement provides abundant storage and offers potential for additional finished living space, studio, recreation room or workshop. The attached two-car garage keeps vehicles protected and provides easy access to the house, while a smaller detached garage is perfectly suited for lawn equipment, bicycles and all the tools needed to maintain your country surroundings. The whole house generator will rise above any storm and keep the electric on. And then there is the location. The Harlem Valley Rail Trail and Alander mountain trail heads are just steps away, offering miles of scenic terrain for walking, running and cycling. Under Mountain Golf Course is practically at your doorstep, just yards up the road. Spend Saturday mornings at the Copake Farmers' Market, explore the nearby lakes, villages and restaurants, or head out for a day of skiing at Butternut or Catamount, both approximately 30-45 minutes away. Hudson and Amtrak are about 25 minutes away, while New York City is approximately 2.25 hours. A peaceful woodland setting, wonderful character, exceptional kitchen, inviting outdoor spaces and significant recent improvements come together beautifully here. This is more than a house in the country--it is a place where nature becomes part of everyday life.

224 Under Mountain Road, Ancram

$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

$620,000
3 Beds 2 Baths 1044728 MLS
Welcome to this charming country home set along a quiet rural road in Copake. Bright, comfortable living spaces and a peaceful setting surrounded by mature trees and open lawn create an atmosphere that feels instantly relaxing. The open living area brings together the updated kitchen, dining room, and living room anchored by a brick fireplace—perfect for cozy evenings. French doors open to a warm, sun filled room, with additional French doors from both the dining room and sunroom leading out to a private deck for effortless indoor-outdoor living. The home offers a good-sized primary bedroom with its own bath, plus 2 bedrooms, a common bath, and a family room for flexible use. A built-in garage adds convenience, while the detached 2 car garage features a workshop and a finished studio above ideal for creative space, guests, or a home office. The home has an automatic whole-house generator installed just incase of a power outage. Enjoy privacy, nature, and easy access to Copake Lake, Bash Bish Falls, Catamount, Hudson, and Great Barrington. An ideal choice for full time living or a welcoming weekend retreat in the Hudson Valley.

33 Twin Bridges Road, Copake

$615,000
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
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

$389,000
3 Beds 1 Baths 1035127 MLS
Welcome to your dream country escape! This charming, fully renovated Cape Cod home has been meticulously rebuilt down to the studs, offering brand-new modern finishes while preserving its classic character.Step inside to discover a bright, airy open floor plan designed for effortless entertaining and comfortable daily living. Owner in process of finishes which will include, electric fireplace, front porch and new kitchen. Still time to pick cabinetry colors for kitchen once under contract. Situated just a 2-hour drive via the Taconic State Parkway, this property is the ideal second home or weekend retreat. Enjoy the tranquility of Columbia County with the ultimate convenience: you are within walking distance to Copake Lake, local dining, marina access, golf course and outdoor recreation. Move right in and start enjoying Hudson Valley living from day one!

235 Birch Hill Road, Copake

$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

$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
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

$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

$939,000
3 Beds 2 Baths 1015339 MLS
Down a quiet country road is this 1860 Farmhouse with Studio building sits on 34.9 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 Studio Building lend both beauty and utility, of 1720 Square Feet 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

$849,900
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

$495,000
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

$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

$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

$495,000
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

$1,650,000
3 Beds 3 Baths 961602 MLS
Spectacularly renovated and offered for the first time since its complete transformation, this exceptional pondfront residence overlooking Maiden Lake is located within the highly sought-after Fern Hill community and offers refined design, privacy, and effortless indoor-outdoor living. The home is clad in warm natural cedar siding, lending timeless character while blending seamlessly with the surrounding landscape. Maiden Lake is a shared pond maintained by the Fern Hill HOA with private swimming access. Set on a quiet country road just outside the Hawthorne Valley hamlet, the property is minutes to Great Barrington, Massachusetts, close to respected private schools, and offers convenient access to the Taconic Parkway and Albany International Airport, allowing for easy travel from New York, Boston, and Connecticut. The thoughtfully designed home features multiple private bedroom suites, lofted ceilings, and expansive light-filled living spaces. Interior finishes highlight exceptional natural materials and craftsmanship, including white oak flooring in the main living areas, cherry cabinetry, soapstone kitchen countertops, French oak stairs, and a custom single-stringer stair with a black steel beam, black steel railing, and white oak banister. Bedroom suites feature maple flooring, while the upstairs loft, office, or studio includes wide-board pine floors. Custom wainscoting and a dedicated linen closet serve the bedroom suite hallway. The open main living area centers around a well-appointed chef's kitchen with an oversized dining island and additional dining space. Premium stainless steel appliances include a Bosch wall oven, Thermador gas cooktop, Fisher & Paykel refrigerator, KitchenAid dishwasher, and Zephyr range hood. Bathrooms feature white subway tile, marble sink countertops, rain and hand-shower fixtures, and wood-grained porcelain tile flooring. The home is filled with light and comfort through Marvin triple-pane windows and doors with built-in shades, automated skylights, and thermal skylight shades. Ceiling fans, insulated thermic shades, and remote-operated skylights enhance energy efficiency and airflow. Multiple dedicated home office areas support flexible modern living. Year-round comfort is provided by an energy-efficient heat pump system with heating and cooling, radiant heated floors in the main living areas and primary bathroom, and a separate gas furnace serving the rear portion of the home. A whole house backup generator provides added peace of mind. Additional upgrades include high-efficiency insulation, fully updated plumbing and electrical systems, a 400-amp electric service, and ethernet outlets. A gas fireplace adds warmth to the main living space. The laundry room includes cherry cabinetry and Bosch stackable washer and dryer units. The entry mudroom features a brick floor, bluestone bench seating, antique wood beams, a Buderus European-style radiator, abundant windows and skylights, and generous storage. The landscaped grounds include perennial gardens, bluestone walkways, copper gutters and drainspouts, selective fencing suitable for small livestock or chickens, and fenced raised-bed gardens. A charming barn includes a three-to-four-person luxury sauna with an Amerec SaunaLogic controller and Laava series heater. Outdoor living is exceptional, with an expansive wraparound Brazilian walnut deck, a spacious gazebo with sweeping pond views, an additional deck overlooking the water, and a dock. Cultural destinations like Hudson galleries, Art Omi, Tanglewood, and Jacob's Pillow are nearby, along with skiing at Catamount, Jiminy Peak, and Butternut. Best of all, Hawthorne Valley Waldorf School and the renowned Hawthorne Valley Farm Store—featuring the highest quality local, organic, and biodynamic food—are just moments away by foot or bicycle.

119 Fern Hill Road, Ghent

$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

$1,250,000
4 Beds 3 Baths 882928 MLS
Step into a world of timeless charm and understated luxury with this impeccably restored 18th-century farmhouse, nestled on over 6 acres of landscaped lawns, flowering gardens, and river frontage along the trout-rich Roe-Jan Kill. The residence exudes warmth and authenticity, offering luminous interiors and inviting outdoor living spaces ideal for entertaining or quiet retreat. The grand living room, anchored by a wood-burning fireplace and lined with a wall of windows, frames views of the grounds and invites natural light throughout the day. The custom-designed kitchen marries modern function with period detail, while the sun-drenched dining room—with exposures on two sides—provides an elegant setting for intimate gatherings. A deep, screened porch spans the length of the north wing, overlooking the gardens and flowing lawns. On the main floor, a serene en suite bedroom and a private guest suite with sitting room and separate entrance offer flexible accommodations. Upstairs, two charming bedrooms share a beautifully appointed bath. A short stroll through lush gardens and across a second private drive leads to the stunning, two-story post-and-beam barn. Currently curated as an antique store, the structure offers an expansive lofted studio and is zoned for commercial or residential use—ideal for a gallery, guesthouse, or creative workspace. This rare, historic compound offers a peaceful, pastoral lifestyle just over two hours from Manhattan—a perfect fusion of old-world charm and modern-day potential. Tucked into the rolling foothills of the Berkshires, Hillsdale is one of the Hudson Valley’s most coveted enclaves—quietly elegant, unspoiled, and deeply rooted in charm. Just over two hours from Manhattan, it offers the ideal blend of refined rural living and easy access to the region’s most sophisticated cultural and culinary experiences. Here, sweeping vistas, winding country roads, and historic farmhouses coexist with curated farm-to-table restaurants, chic design shops, and proximity to world-class destinations like Hudson, Great Barrington, and Tanglewood. Hillsdale is home to Catamount Mountain Resort for year-round recreation, from skiing to ziplining, and just minutes from Copake Lake, private golf clubs, and nature preserves. Discreet, low-key, and deeply authentic, Hillsdale attracts those seeking serenity without sacrifice—an elevated escape that feels worlds away, yet entirely within reach. Hillsdale is fast becoming one of one of Columbia County’s most desirable investment destinations. Just over two hours from Manhattan, this historic town offers a rare combination of timeless charm and smart, long-term value. As boutique hospitality, curated design, and high-end food culture continue to expand nearby—in Hudson, Great Barrington, and Chatham—Hillsdale has quietly emerged as a prime location for luxury second homes and discreet development. With a strong track record of appreciation and zoning that allows for flexibility, it's an ideal market for those looking to balance lifestyle with strategic growth Hillsdale offers proximity to a refined network of private clubs, golf courses, and recreational resorts that define the elevated Hudson Valley lifestyle. You're just minutes from the exclusive Copake Country Club, private lakefront communities, and the slopes of Catamount Mountain, offering four-season access to skiing, hiking, and ziplining. Paired with nearby spas, organic farms, and award-winning restaurants, Hillsdale is a magnet for those who appreciate privacy, taste, and a quietly luxurious pace—without sacrificing access to world-class experiences.

9960 Route 22, Hillsdale

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