Courtesy: Columbia County RE Specialist
518-325-9784
Discover a truly beautiful, peaceful setting at 309 Pine Ridge Lane, a 2,500-square-foot, traditional colonial home custom built in 1996. Three-bedroom, three baths, set on just under 6 acres of pristine woodlands on one of Hillsdale's prettiest country roads. This home offers the rare combination of modern architecture, privacy, and effortless living. Walls of windows in the living room and kitchen, that invite a constant play of light throughout the interior and frame the surrounding landscape. An Open Floor plan blends artistic uniqueness with sophistication, including built in carvings of repurposed wood designs from New Orleans perfectly placed above the wood burning stone fireplace in the living room, as well as in the 1st floor primary (ensuite bathroom) bedroom & upstairs office/great room that frames the cathedral ceiling overlooking the downstairs. Custom hand milled wooden stair rail, balcony off the upstairs landing overlooking the front yard, and so many other beautiful accents. Outside you find hand laid stone walkways up to the front wrap around porch. All this and more, found on a lightly traveled quiet road, just minutes to Catamount for year-round entertainment, along with hiking, biking, theatre and performing arts and multiple awesome restaurants of the area. Full basement with high ceilings can easily be finished for additional living space. Located halfway between Hudson NY and Great Barrington MA. Close to Tanglewood, 2.5 hrs. to NYC and/or Boston.
Courtesy: Four Seasons Sotheby's Int.
518-822-0800
A modern country home inspired by the farmhouses of the Hudson Valley. Taconic Creek Road is tucked away amongst rolling hills and large surrounding parcels, on a beautiful dead end road with just a few lovely houses. The palette is restrained but luxurious with a thoughtful layout and custom design details. Spanning 2,100 square feet, you'll find lime washed walls with stunning depth of color, custom millwork and wideboard wood flooring that adds warmth to the space. The main living area is anchored by the open kitchen, with Tundra Gray marble counters, an English farmhouse sink, custom inset cabinetry and paneled appliances. A deVOL pendant hangs over the kitchen table. The sitting area is lined with custom built bookshelves and there are large, deep windows lining the room. They face out into the garden, and french doors at the center take you onto the patio. There is storage and a built in bench at the entry for your boots and bags, and a lovely bath on the main level with Noguchi pendant lights. Upstairs, a light filled sitting room walks out to a screened in porch, and there are three bedrooms spread out across the floor. The primary suite is large with a stunning picture window, an office/walk-in closet and a gorgeous bathroom. You'll find a walk-in-shower and soaking tub with views of the surrounding treetops. Two other bedrooms share the third bathroom off the hall. There is an extensive list of upgrades that includes a new roof, HVAC and septic, and the current owners buried the electrical lines to the house. A large pool is surrounded by lilacs and hedges, private and peaceful, and there is a garage for parking. Taconic Creek Road offers a rare level of calm and sophistication just 15m to Hudson and Amtrak and under 2.5h north of NYC.
Courtesy: Stone House Properties, LLC
518-392-0332
2999 Route 23, Hillsdale, New York - Historic Country Estate on 12.5 Acres Step into a piece of living history with this beautifully preserved 1915 home, perfectly situated on a private 12.5-acre parcel in the heart of the Berkshires. Offering four generous bedrooms and three baths (2 full, 1 Half), this classic residence blends timeless charm with everyday comfort, creating an ideal setting for family living, weekend escapes, or peaceful country entertaining. Outside, the grounds are nothing short of spectacular with flower beds are scattered around the house and front yard. Cool off in the sparkling in-ground pool, relax by the tranquil pond, or follow the gentle sounds of the year-round stream that flows along the property. The magnificent 1800s post-and-beam barn stands ready for your vision, whether as a workshop, artist studio, equestrian space, or rustic gathering spot. Located just a stone's throw from Catamount Ski Mountain, this property minutes away from skiing, snowboarding, and year-round mountain recreation right at your doorstep. In warmer months, enjoy hiking trails, scenic drives, and the vibrant cultural scene of nearby Hudson and Great Barrington. With its rare combination of historic character, abundant water features, and sweeping acreage, 2999 Route 23 offers a lifestyle that's equal parts serene and invigorating. This is more than a home--it's a private Berkshire retreat waiting for its next chapter. Ready for showings or more details? Reach out today to experience it for yourself.
Courtesy: The Kinderhook Group, Inc.
518-751-4444
WRENROCK. This idyllic Arts and Crafts cottage, built in 1906, is nestled in a woodland setting. Located in bucolic Hillsdale on a beautiful country road, it is within minutes to the town center, Catamount, the farmer’s market and library. A deep porch with stone pillars is at the front of the cedar shingled home. The main level is a large open space with dark hardwood floors. There are multiple windows that allow natural light to flood the room throughout the day. A large stone fireplace anchors the room; it is the ideal spot to relax on a cool evening. The second level has exposed rafters and skylights, perfect for nighttime star gazing. There are two bedrooms, a sitting /reading area and a bathroom with a clawfoot tub. The lower level is an open space with an updated kitchen with stainless steel appliances and quartz countertops. There’s plenty of room for dining and hanging out…and a woodstove for extra warmth. Large windows and French doors allow views of the woods and wildlife. There is a second bath with a walk-in shower. At the back of the cottage, there is a bluestone patio that’s perfect for dining al fresco. An old icehouse on the property functions as a garden shed. Wrenrock is move-in ready. The cottage is available fully furnished for an additional fee. Agent owned.
Courtesy: Copake Lake Realty Corp.
518-325-3921
Sited on 5 beautifully landscaped acres on a very quiet, park-like setting off a private road, this well maintained and thoughtfully designed home overlooks a tranquil pond and offers the perfect country escape. Designed by architect Dennis Wedlick, to maximize space and ease of living, the home features 3-4 bedrooms, and 3 baths, of which one is a primary ensuite and another a separate guest suite. A renovated kitchen and updated baths blend seamlessly with gleaming wood floors and a striking double-sided fireplace connecting the living room and den. Custom designed windows fill the home with natural light while framing picturesque views. An exceptional property in a bucolic setting, ideal as a full time residence or low-maintenance getaway, Solar panels to reduce energy bills and EV charger in garage. Private, polished and effortlessly livable, this distinctive country retreat is for the buyer seeking design and setting. Could be sold turn key.
Courtesy: Columbia County RE Specialist
518-325-9784
This one checks all of the boxes. Our newly listed two bedroom, two bath Cape Cod style home in Hillsdale has been meticulously maintained and is in excellent condition inside and out. The main level features a functional kitchen, dining area, bathroom, and living room centered around a propane fireplace; all with hardwood floors. A 12x12 great room with hardwood floors was added to provide additional living space. Ideally located on one of Hillsdale's prettiest country roads and in close proximity to everything that makes Hillsdale such a popular destination. Whippoorwill Road is within a short drive of Catamount Ski Area, Vine Gate Lavender Farm, the HV Rail Trail, Taghkanic State Park, The Copake-Hillsdale Farmers Market, Copake Lake, downtown Hudson and the Berkshires. The 5-acre parcel is completely tree lined for total privacy and seclusion. A garden shed, large gazebo and spacious deck overlooking the back yard make enjoying the outdoors a breeze all summer long. ''Neat as a pin'', ''cute as a button'', ''big things come in small packages''. These superlatives all ring true. You have the power to make them more than a superlative. You can make them become a reality!
Courtesy: Four Seasons Sotheby's Int.
518-822-0800
Welcome to a newly built modern farmhouse estate set on 11.7 private acres in the heart of Hillsdale. Arriving via a sweeping driveway, rolling lawns unfold into cultivated fields and far-reaching pastoral and mountain views in every direction. Designed for indoor-outdoor living, this 4-bedroom, 4-bath residence blends modern architecture with the warmth and ease of Hudson Valley living. Clean architectural lines are softened by natural materials, soaring vaulted ceilings, and expansive walls of glass that fill the home with changing light throughout the day. At the center of the home, the dramatic great room rises to a 20-foot vaulted ceiling anchored by a wood-burning fireplace clad in earthy, chestnut-toned marble. Large Arcadia custom glass doors open seamlessly to over 540 square feet of covered outdoor living space, creating an effortless connection between indoors and out--ideal for entertaining, quiet mornings, or long sunset evenings overlooking the landscape. The kitchen was designed as both a gathering space and a functional centerpiece, featuring custom walnut cabinetry handcrafted by a Brooklyn cabinetmaker, integrated Fisher & Paykel and Bosch appliances, an oversized monolithic island, and a 48-inch double-oven gas range. A generous butler's pantry and bar area adds additional prep space, storage, a second dishwasher, prep sink, and microwave drawer--allowing the main kitchen to remain clean, open, and entertaining-ready. The primary suite is a private retreat with vaulted ceilings, a custom dressing room, and a spa-like bath finished in dramatic Calacatta Violetta marble with soaking tub, oversized shower, and fluted glass steel-framed doors. Upstairs, a second primary suite offers a walk-in closet and marble-appointed bath, alongside an additional en-suite bedroom. A versatile fourth bedroom on the main level offers flexibility as a guest suite, office, wellness room, or media space with direct patio access. Thoughtfully engineered for high-performance living, the home features spray foam insulation, high-performance windows, forced-air heating and central air conditioning, on-demand hot water, Lutron lighting controls, remote-access thermostats, generator hookup readiness, and a heated detached 26x26 two-car garage. Just minutes from Catamount Mountain Resort and the Hamlet of Hillsdale, and within easy reach of Great Barrington and Hudson, the property offers a rare combination of architectural refinement, rural privacy, and access to the Hudson Valley and Berkshires' celebrated farm-to-table dining, local markets, cultural destinations, and year-round recreation. A modern farmhouse of quiet confidence, architectural clarity, and elevated rural living. (listing agent has a financial interest in the property)
Courtesy: Compass Greater NY LLC
914-238-0676
Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere you look you stop to take in the view, large bath with walk-in closet and laundry. The inner courtyard has a heated pool, sunken jacuzzi, outdoor shower, screen porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.
Courtesy: Houlihan Lawrence Inc.
518-822-0300
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 for family. 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.
This updated contemporary home in Hillsdale offers a perfect blend of comfort and style on 10 private acres. The interior features a mix of hardwood, carpet, and nearly new vinyl flooring complemented by fresh paint and trim throughout. The kitchen comes fully equipped with a refrigerator, microwave, and stove. Enjoy a semi-finished basement. Key updates include new electric and plumbing, an electric HVAC system, and a 12-year-old roof. Complete with a 1-car garage and a solid foundation. Assignment Listing.
Courtesy: Compass, Hillsdale
914-327-2777
Offering privacy, quality construction, and an ideal location. Set in the heart of the Roe-Jan region of the Hudson Valley and at the edge of the Berkshires, this home is tucked privately among mature trees on nearly eight acres while remaining close to the center of town. Recently constructed by one of the region's top builders, the residence was designed with both quality and longevity in mind. Notable features are a durable metal roof and 'Hardie Board' clapboard siding, ensuring minimal maintenance. Inside, a welcoming entry foyer and mudroom provide a practical transition from outdoor to indoor living. The open-concept great room combines living and dining into one modern space for everyday living and entertaining. The kitchen anchors the room with a large breakfast bar, and a spacious office on this level provides flexibility. It could easily function as an additional sleeping space. Upstairs, the primary suite occupies half of the second floor, offering a private retreat complete with a spacious walk-in closet and an ensuite bath. Two generously sized guest bedrooms share a full guest bathroom. There is a large heated two-car garage with storage room with an adjacent fenced meadow. It is the perfect space to keep animals, for pets to roam safely, or simply a wide-open area for recreation and relaxation.
Courtesy: Venture Fox Realty Group
518-290-1070
Set on the shores of Copake Lake, this charming waterfront home blends classic lake character with thoughtful modern updates. Offering three bedrooms and 1.5 baths, the home features a bright open kitchen, living, and dining area designed for easy lake living and entertaining. Recent renovations, including HVAC, septic system, and expansion to main floor, bring fresh style and comfort while maintaining the cozy charm expected from a lakeside retreat. French doors open to a spacious deck overlooking the water, creating a seamless connection between indoor living and the peaceful lake views beyond. Just steps from the deck, enjoy your private shoreline and dock--perfect for swimming, boating, and relaxing by the water. Copake Lake is one of the area's only fully motorized lakes, ideal for water sports, fishing, and sunset cruises. Conveniently located near Copake Country Club and Catamount Mountain Resort, and under 30 minutes to both Amtrak and Metro-North rail service, as well as the vibrant towns of Hudson, NY and Great Barrington, MA
Courtesy: Compass Greater NY LLC
914-238-0676
This charming 3 BR, 1.5 Bath cottage is located across the street from Copake Lake and the HOA Waterfront, Marina and Beach area. Unlike some of the other homes in the area, the house is situated on an elevated, oversized lot with a big front yard and spectacular sunset views. Inside, the house features real wood paneling and a wood burning stove in the living room, a cozy kitchen with a new gas stove (November 2025) , and a dining area. The 3 Bedrooms are in the back of the house and one of them has a half bath ensuite. A full bathroom is off the hallway. This home features central heat with in-wall air conditioners. Copake Lake is approximately 425 acres and close by to multiple ski mountains, outdoor recreation, world class road biking, and the Copake Lake Country Club with its 18 Hole course and award winning restaurant , The Greens. Currently, there is a boat slip available, depending on the type of boat. Access to this Hudson Valley lifestyle is only 2 hours from NYC and 2.5 hours to Boston For Showings, please contact Russ Stein at [email protected]
Courtesy: Coldwell Banker Advisor Realty
518-828-7111
Step back in time and imagine the possibilities with this charming 1800s farmhouse, situated on a picturesque 1-acre lot complete with a pond and stream. Nestled in a desirable area, this property offers a rare opportunity to restore and customize a true piece of history. The home features solid construction and ''great bones,'' providing a strong foundation for a full renovation. A spacious basement adds valuable storage and utility space, enhancing the home's potential for modernization and expansion. While the property requires a complete rehabilitation, the setting make it well worth the investment. Surrounded by natural beauty, the expansive lot offers endless opportunities for gardens, outdoor entertaining, or simply enjoying the peaceful water views. Whether you envision a thoughtfully restored historic residence, a charming country retreat, this outstanding site provides the perfect canvas. Bring your vision and transform this classic farmhouse into something truly special.
Courtesy: The Meenagh Group Realty
518-281-5496
1800s farm house. Just waiting for some TLC. This property consists of the main farm house. one very large barn. Addtional 3 out building. One of the back building contains an attractive apartment.The property butts up to the Harlem Valley Rail Trail. Walking distant to the Hamlet of Hillsdale. Including the Roe Jan Brewing Co. IGA, The Hillsdale House, The town park. Less then 5 min ride to Catamount. 25 min ride to Hudson NY. 20 min ride to Great Barrington MA.Property is being sold as is.
Courtesy: The Kinderhook Group, Inc.
518-751-4444
A rare 193-acre estate in Austerlitz/Hillsdale, very close to the Berkshire border. The charming 3-bed cottage overlooks a pristine pond with a bordering creek. The wooded land has clearly marked and maintained hiking trails. Recently renovated, the cottage features an updated bathroom and an expanded living room, blending modern comfort with rustic charm. Geothermal heating and air conditioning ensure energy-efficient living year-round. An additional structure offers flexible space, ideal for a studio, guest quarters, or creative retreat. Two parcels make up the property, with a conservation easement ensuring that the land is protected from further development (an 18-acre portion may be built upon.) Note that the abutting property at 890 Bald Mountain Road, a gorgeous 85-acre compound with main house and two guest houses may be purchased from same seller (listed at 5.95 Mil.)
Courtesy: Coldwell Banker Advisor Realty
518-828-7111
Come see the new me!. I've had a face lift and you are sure to enjoy the gleaming hardwood floors and the updated kitchen with granite counters and new appliances. It's one level of easy living, and offers many wonderful features. Enjoy the spacious living room framed by a fireplace, or the cozy den which has one as well..The middle bedroom features sliders that open onto a deck, great to enjoy your morning coffee, or use as office space and let the wonders of the outdoors inspire you. A new roof, fresh paint, inside and out, new septic and more, mean less work for you and more time for fun. A wonderful opportunity just minutes from the hub of Hillsdale, Copake Lake, Catamount Ski area and the beautiful Bash Bish waterfalls. A brief drive will get you to Great Barrington or Hudson and its just 2 hours to NYC.
Courtesy: Four Seasons Sotheby's Int.
518-822-0800
Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County's most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a constant play of light throughout the interior and frame the surrounding landscape as living art. Inside, the soaring cupola-topped ceiling and radiant-heated polished-concrete floors create a calming, loft-like atmosphere, anchored by a dramatic floating propane fireplace. The designer kitchen integrates seamlessly into the open living and dining spaces, making the home equally suited for quiet evenings or stylish entertaining. Two airy, loft-style sleeping areas, and two sleek glass-and-steel baths complete the thoughtfully curated layout. Every element of the home blends sophistication with simplicity—ideal for a buyer who values design, nature, and ease. Tucked away yet minutes from Hillsdale, Hudson, Egremont, and Great Barrington, the location offers instant access to the region's best culture, dining, and outdoor recreation. With NYC and Boston a little over 2 hours away, this property is the perfect full-time escape or effortlessly luxurious weekend base. A rare architectural and design statement, this steel-and-glass modern barn redefines country living for the buyer seeking something truly unique.
Courtesy: Four Seasons Sothebys Intl
518-822-0800
Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County’s most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a constant play of light throughout the interior and frame the surrounding landscape as living art. Inside, the soaring cupola-topped ceiling and radiant-heated polished-concrete floors create a calming, loft-like atmosphere, anchored by a dramatic floating propane fireplace. The designer kitchen integrates seamlessly into the open living and dining spaces, making the home equally suited for quiet evenings or stylish entertaining. Two airy, loft-style sleeping areas, and two sleek glass-and-steel baths complete the thoughtfully curated layout. Every element of the home blends sophistication with simplicity—ideal for a buyer who values design, nature, and ease. Tucked away yet minutes from Hillsdale, Hudson, Egremont, and Great Barrington, the location offers instant access to the region’s best culture, dining, and outdoor recreation. With NYC and Boston a little over 2 hours away, this property is the perfect full-time escape or effortlessly luxurious weekend base. A rare architectural and design statement, this steel-and-glass modern barn redefines country living for the buyer seeking something truly unique.
Courtesy: Four Seasons Sotheby's Int.
518-822-0800
For the first time on the market in 50 years, Underwood Farm, with its late 18th century cedar shake 3200 square foot salt box house, is 281 acres of primo hilltop exposure. Driving the property, the entire expanse is the high ground between West End Road and Rockledge Road with its equal parts woods, open meadows and fields with the rolling Taconics to the East. Below, the neighborhood is experiencing a renaissance and is dotted with new restorations of gorgeous farmhouses and new builds, adding a fresh dynamic to the area. This site is perfect for any health and wellness guru looking to recreate life on a farm for the benefit of the community, for an hotelier or hospitality group to develop an Upstate experience compound or simply to restore a piece of American architectural history to become a beautiful 4 bedroom 2 bathroom residence in the heart of the Craryville to Hillsdale corridor and all the conveniences that entails. The house sits high on a bluff overlooking West End Road and below the dale is a large former dairy barn with a metal roof and cattle stalls. There is a detached garage with an efficiency apartment over it behind the house with the opportunity to plant a crop in an adjacent waiting field. Three large parcels make up this offering and the residence has the opportunity to sell the remaining two while maintaining 100+ acres for an impressive estate.
Courtesy: Red Apple Realty
518-851-9601
Newly Renovated Hillsdale Gem! Welcome to this beautifully renovated 3-bedroom home in the heart of Hillsdale. Thoughtfully updated with today's buyer in mind, this residence blends modern comfort with timeless charm. Inside, you'll find a bright, welcoming kitchen featuring quartz countertops, high-end vinyl plank flooring, and a suite of updated appliances designed for both style and functionality. A large living room perfect for entertaining, with a potential dining area on one end featuring a built-in china cupboard. There is also a separate family room with a wood stove to keep you cozy on chilly nights, with glass doors that lead you out to the 18' x 18' stone patio that is ideal for summertime relaxation and entertainment. The two bedrooms on the main level are serviced by the updated 3/4 bath, while a large third room upstairs offers endless possibilities for an additional bedroom or office. For your convenience, there are laundry facilities with built in storage and cubbies located in the entry way mudroom. Step outside to your private backyard; a serene retreat perfect for morning coffee, entertaining, or simply unwinding in nature. The outdoor space offers a fenced-in portion of the 1-acre yard, privacy, and tranquility, making it a true extension of the home. Every detail has been carefully considered; from the freshly installed siding to the recent roof, ensuring peace of mind for years to come. This turnkey property is ready for its next chapter - whether you're seeking a weekend escape or full-time residence, this home delivers modern living in a peaceful Hudson Valley setting.
Courtesy: Gilcrest Properties
518-610-8121
New listing in Hillsdale, set high on a quiet dirt road where privacy, peace, and panoramic views define your backdrop. Why wait a year and a half for a new house to be built? This brand-new construction is being sold as it stands today, as a blank unfinished canvas ready for you to make it your own. The structure is in place with a brand-new drilled well, septic system, and 200-amp electrical service already set. Plumbing, electric hookups, walls, flooring, fixtures, and finishes are still needed--giving you full creative freedom to choose your style and finish every detail to your taste. The main level offers 1,800 sq ft with 3 bedrooms, 3 bathrooms, and a dedicated home office. With soaring 10' ceilings, oversized rooms, and new Pella windows and doors, the home is flooded with natural light and sweeping easterly views across the marsh and surrounding landscape. Step out onto the massive mahogany deck where Mother Nature puts on a show in all four seasons--whether it's fall foliage, winter snow-glow, spring blossoms, or endless summer skies, the scenery is ever-changing and unforgettable. The walk-out lower level adds another 1,800 sq ft of potential, waiting to be transformed into whatever you can dream up--an expansive recreation room, home theater, wet bar and lounge, gym, or even a golf simulator. The possibilities are truly limitless. Nestled among the trees with total seclusion yet close to everything, this home is ideally located. Just 15 minutes to Hudson for dining, shopping, and the Amtrak station, 2.5 hours to NYC, and surrounded by year-round recreation. Skiing at Butternut, Catamount, and Jiminy Peak are all within 30 minutes. Bash Bish Falls, multiple conservation areas, and endless hiking and biking trails are minutes away. This is more than just a house--it's an opportunity to skip the waiting list and create the Hudson Valley retreat you've always imagined. With the hard work done and the canvas set, the only thing missing is your vision.
Courtesy: Four Seasons Sothebys Intl
518-822-0800
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.
Courtesy: Houlihan Lawrence, Inc
518-822-0300
Welcome to Wolverton Creative Compound, a storied 119-acre estate set within a hidden valley offering complete seclusion, integrated creative workspaces, and timeless beauty. The original 1830s farmhouse is tucked away at the end of a private lane in Claverack, NY, where the road terminates in a round gravel driveway anchored by the property's original stone well. Two large ponds grace the land, including an aerated, swimmable pond directly in front of the house. Sited among meadows and mature woodlands, the main house, upgraded studio barn, and charming studio shed are framed by terraced stonework, a network of trails, and thoughtfully designed gardens. The setting is peaceful, restorative, and deeply connected to the land, yet only a short drive to both Hudson and Great Barrington. The antique farmhouse offers four bedrooms and three bathrooms across 2,825 square feet, where original details like moldings, wood floors, and Dutch doors preserve its old-world charm. A generous double living room and a Vitsoe-outfitted studio lead to a bright dining area and kitchen, each with direct access to patios and gardens. The layout supports an easy indoor-outdoor rhythm, with covered porches and multiple terraces for lounging, cooking, or gathering. Two staircases rise to the upper-level bedrooms, where southern exposure fills each room with light, and the insulated attic improves year-round comfort. Throughout the home, an intentional color palette lends softness and cohesion. The design brings together European sensibility and Hudson Valley character, creating a live-work compound that balances utility with ease, warmth, and quiet sophistication. Across the garden sits a fully insulated 1,900-square-foot historic barn transformed into a large-scale creative studio, complete with bathroom and clawfoot tub, kitchenette, updated electrical, and HVAC. The studio is wired for photography, cinematography, sound, editing, and workshop use, with fiber-optic service and an underground data connection linking house and studio. The compound has a full HUE lighting system with states created by a film lighting designer. A detached potting shed offers another versatile space, ideal as a garden studio, writer's nook, or future guest cottage, and connects to an outdoor bath deck that invites restorative soaks beneath the stars with its fireplace, clawfoot tub, and outdoor shower. A carport at the barn with EV charging and a full-property generator ensure comfort and continuity year-round, whether for everyday living or on-site production. A whole-house water filtration system adds another layer of comfort. The primary pond is the centerpiece of the property. This aerated, swimmable pond, bordered by a pebble beach and firepit, is ideal for swimming or evening gatherings after a day in the studio. Terraced gardens by The Secret Gardener surround the home with a cottage-style blend of flowering plants, herbs, and vegetables. Rewilded fields and meadows lead to two miles of maintained trails through native grasses and towering trees. The land qualifies for a forestry exemption and includes multiple cleared areas, offering potential for a guest house, additional studios, horses, or even a helipad. Whether hosting music on the lawn, staging a shoot, convening a creative team, or watching the changing sky reflect in the pond, Wolverton Creative Compound is a rare legacy estate and true sanctuary for creative work and retreat.
Courtesy: Columbia County RE Specialist
518-325-9784
Welcome to Copake Lake!! Sweet two-bedroom, one bath cottage, eat in kitchen, views of the lake from living room and one of the two bedrooms, nice big yard to enjoy outdoor fun. All appliances included. PLUS (As per Seller) water rights along that 20-foot stretch, a buyer may be able to agree with others in the area to extend the existing dock, which could be up to 60 feet into the lake! Property includes lake and water rights, and interested buyers can review the deed and survey with their attorney for further clarification or potential agreements regarding the dock use. Pretty Sweet!!! Sold 'As Is'
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Hillsdale is located in New York. Hillsdale, New York has a population of 1,659. Hillsdale is less family-centric than the surrounding county with 13.6% of the households containing married families with children. The county average for households married with children is 22.64%.
The median household income in Hillsdale, New York is $81,293. The median household income for the surrounding county is $73,065 compared to the national median of $69,021. The median age of people living in Hillsdale is 53.4 years.
The average high temperature in July is 82.4 degrees, with an average low temperature in January of 12.4 degrees. The average rainfall is approximately 46.2 inches per year, with 53.4 inches of snow per year.
