Courtesy: Columbia County RE Specialist
518-325-9784
PRIVATE & QUIET ~ 124 Syre Lane, Hillsdale NY Federal Style Colonial home in Hillsdale, perched on the top of the mountain, pairing historical accuracy with state-of-the-art modern conveniences. This stately country home offers unparalleled, endless views in every direction of the valley and Catskill Mountains. Offering Immeasurable beauty, from every window and large back deck, perfect for enjoying sunsets. General Features: - Living space of 5,700+/- square feet situated on 12.02 acres - Custom floor-to-ceiling windows with built-in wood shutters created by New England craftsmen - High ceilings, natural sunlight, a gourmet kitchen, modern appliances, and top-of-the-line radiant heat - Whole house generator and Hardie Board siding - Standing seam roof - Post & Beam 3-bay garage with mini splits and a large upstairs studio featuring wide board flooring First Floor: - 10' ceilings with crown molding - 40' living room and dining room areas featuring two fireplaces with antique period mantles - Study, library, or additional bedroom option Second Floor: - 10' ceilings - Primary bedroom/master suite with two walk-in closets, a dressing room, a private office, and a gourmet ensuite bathroom equipped with a jet jacuzzi bathtub and steam shower - Massive guest suite - Bedrooms 2 & 3 with a shared ensuite bathroom Basement & Utilities: - Mini splits, gym, and game room - Additional bedrooms and a utility room - Two water softeners, two oil tanks, and a Buderus furnace
Courtesy: Elyse Harney Real Estate
518-789-8800
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.
Courtesy: Copake Lake Realty Corp.
518-325-9741
OPEN HOUSE - (Saturday) August 8 from 2-4 p.m. The Edward Herrington House, circa 1886 - 1898 is one of the historic homes in the charming hamlet of Hillsdale, New York. A multi-century-old sugar maple greets you as you enter this quaint Hamlet Historic District home. This spacious 3-bedroom, 1.5 bathroom heritage residence takes you back in time with its many original details while providing important updates. Read a book from the built-in library in the sitting room or gather by the centrally located woodstove on cold winter days, which really does heat the house, and relax in the peaceful upstairs screened-in sleeping porch in the warmer months. Enjoy the private fenced backyard with a stone patio, raised garden beds and a nice-sized shed for storage. Some other amenities include a reverse-osmosis water filtration system, hardwood floors throughout, built-in cabinets and even a Murphy bed and more. The location is ideal for those looking for a village home in a rural community. Right down the road you will find the Harlem Valley Rail Trail and the Roe Jan Brewing Co., renowned for its wood-fired pub menu and a wide variety of craft beers brewed onsite. The brewery also sits inside the historic 1851 Hillsdale Mercantile Building. Check out downtown Hillsdale's local shops, restaurants, farmers markets, parks, library, antiquing, and the hamlet is only 6 minutes from Catamount's Adventure Park,, which offers year-round attractions including snow skiing, concerts, ropes courses and the longest zip line in the USA. Tanglewood and the Norman Rockwell Museum are about 30 minutes away too. Hillsdale sits between the vital waterway of the Hudson River - the river that flows both ways - and the beautiful ancient rolling hills of the Berkshire Mountains. Hillsdale is about 2 hours from New York City and 2.5 hours from Boston. It is equidistance to Hudson, NY, and Great Barrington, MA. The Metro-North train station in Wassaic and the Amtrak station in Hudson make it easy to travel to New York City. Enjoy this vintage homestead with all it has to offer within historic Columbia County, NY, known for its beautiful mix of rural farmland, artsy towns, and nature, and is home to several properties recognized on the National Register of Historic Places. Come step back in time. It would be our honor to introduce you to the Edward Herrington House.
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. 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 ample room for a workshop, lawn equipment and recreational storage. The second floor of the garage offers endless possibilities as an artist's studio, home office, fitness room, or hobby space. . 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.
Courtesy: Corcoran Country Living
845-338-5832
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.
Courtesy: Berkshire Hathaway HomeService
518-758-1300
Welcome to THE UPSTATE RETREAT--where every day feels like a vacation on Copake Lake, the largest lake in Columbia County, spanning approximately 425 acres. Whether you're searching for the perfect weekend escape, a summer lake house, or a year-round getaway, this charming 2-bedroom, 1-bath bungalow offers the quintessential upstate lifestyle just over two hours from New York City. Beyond the lake, adventure awaits in every direction. Explore the charming towns of the Hudson Valley and Berkshires, hike nearby Bash Bish Falls and Taconic State Park, ski at Catamount Mountain Resort, tee off at Copake Country Club, or spend the day discovering the renowned restaurants, galleries, boutiques, music, and cultural attractions that make this region one of the Northeast's most desirable destinations. Perfectly positioned just 30 minutes from both the Hudson and Wassaic train stations, The Upstate Retreat offers an easy commute from the city while feeling worlds away. Whether you're looking for a peaceful personal escape or a memorable vacation home, this is your opportunity to experience the very best of Copake Lake living. Home is being offered in ''as is'' condition. Home includes 15 feet of deeded access to waterfront on Copake Lake.
Courtesy: Red Apple Realty
518-851-9601
Discover Your Dream Cape-Style Home: A Serene Escape on 2.1 Acres Nestled in a tranquil setting, this stunning Cape-style home offers the perfect blend of comfort and luxury, with 2.1 acres of nature at your doorstep. Imagine sipping your morning coffee on the spacious front porch while listening to the gentle rustle of leaves around you. Step inside to an inviting and dramatic living room, where vaulted ceilings and a cozy fireplace with a wood stove insert create a warm ambiance. The rich hardwood floors lead you seamlessly into an elegant dining room, also featuring vaulted ceilings and an abundance of natural light, enhanced by gorgeous cherry floors. The heart of the home is a Cook's kitchen, equipped with double wall ovens, a cooktop, a wine cooler, and a center island with a breakfast bar--perfect for family gatherings or entertaining friends. A convenient laundry room on the main level adds to the home's functional design. Retreat to the primary bedroom, complete with a walk-in closet and a freshly remodeled primary bath that boasts a luxurious soaking tub and a spacious walk-in shower, while the first floor also features a stylish half bath for guests. Upstairs discover two large bedrooms and a versatile room ideal for a storage area, home office, or playroom, along with a second full bath for added convenience. Step outside to a huge rear deck that wraps around the side of the house, offering a perfect space for entertaining against a backdrop of serene, wooded views, ensuring maximum privacy. Additional amenities include a generator, a three-car detached garage, and central air conditioning for year-round comfort. The full basement provides ample storage space and a dedicated area for a home gym, complete with a rubber floor for your workouts. Don't miss the opportunity to make this remarkable property your forever home. Schedule a viewing today and experience the tranquility and elegance it has to offer!
Courtesy: Columbia County RE Specialist
518-325-9784
Are you dreaming of times spent tucked away in a rustic cabin, preferably wrapped in a cozy blanket in front of a roaring fireplace? Or maybe you're dreaming of barefoot in the stream that feds into the Green River and sunbathing with rays of sunshine beaming through the trees? Welcome to 251 Overlook, Hillsdale NY! Cira 1900 Cottage in the woods, built on the side of a mountain, on 4.5 Acres. A wood lover's dream. Some features include one bedroom, one bath, eat-in kitchen with classic refrigerator, knotty pine walls, 2-story fieldstone fireplace with enamel stove w/thermal glass doors, a fully lined chimney, cathedral ceiling with exposed beams and a sleeping loft overlooking it all. Located just minutes to Catamount Mountain Resort for Skiing and now the Aerial Adventure Park! 10-min to Roe Jan Library, Copake-Hillsdale Farmers Market, Copake Lake, Copake Country Club, Bash Bish Falls, Harlem Valley Rail Trail, Taconic State Park, near Tanglewood, Jacobs Pillow, Kripalu, endless local amenities, cultural activities, attractions- music, art galleries, museums, restaurants, breweries, wineries, pick-your-own farms. 2 hours to NYC, ½ hr to Hudson NY and on the Berkshire border, Great Barrington only 20 minutes away! Metro North and Amtrak close by. Easy to show.
Courtesy: Four Seasons Sotheby's Int.
518-822-0800
This perfect modern farmhouse retreat is tucked away on one of Columbia County's most quiet and beautiful roads guaranteeing a tranquil respite from the city. Being one of just a handful of properties on the road creates a sense of peace and quiet that is unmatched. While a feeling of simplicity emanates throughout the land there is a clear level of sophistication in the design details. 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 pergola covered 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. The structure is perfectly buttoned up without a single project needed to start your next chapter. The long list of care put into this property by the current owner includes a new roof, HVAC and septic, and buried 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 calmness and proximity; just 15m to Hudson and Amtrak and under 2.5h north of NYC.
Courtesy: Coldwell Banker Advisor Realty
518-828-7111
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.
Courtesy: Coldwell Banker Advisor Realty
518-828-7111
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.
Courtesy: Brown Harris Stevens HV LLC
845-871-2700
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.
Courtesy: Brown Harris Stevens
845-871-2696
Presiding over 27 acres of rolling hills and meadows with exquisite mountain views, Southview Farm is an ideal weekend retreat set amidst the glorious landscapes of Hillsdale farm country. Originally a 300 acre dairy farm, with a grand farmhouse occupying this location for over 100 years, the property has undergone a recent expansion and top to bottom reimagining of the space and grounds, and now offers all of the 21st century comforts of home. The home faces due south, with clear views out over a one acre 14 ft. deep pond to the Catamount Ski area and beyond, and down the Taconic Ridge that runs between the Hudson Valley and the Berkshires. The landscape is so special that scenes from Ang Lee's ''Taking Woodstock'' were filmed here, as the views in front of the house closely resembled the site of the original Woodstock music festival. The headwaters of the Roeliff Jansen Kill, a major tributary to the Hudson River, define the property line to the east, tying this land directly to the rich history and scenic character of Columbia County and the Hudson Valley. Southview boasts over 5000 square feet of living space and is currently comprised of four bedrooms and five and a half bathrooms. Among the second floor bedrooms there are also a den, office and laundry room. The third floor opens to a vast space with soaring cathedral ceilings, currently used as a gym and sitting area, which could easily provide an additional two bedrooms with baths en-suite if desired. The ground floor of the home is built around the original center stair hall and is anchored by the heart of the house- an enormous chef's kitchen with an 18 foot L-shaped island, soapstone countertops, double sinks, both a Wolf dual fuel 48'' range and under counter Convection Micro, plus a 42'' Subzero refrigerator. The kitchen also incorporates one of the two relocated wood burning fireplaces, preserving and reusing the original bricks of the historic farmhouse. Two wonderful rooms shoulder the kitchen- a sunny and well-appointed butler's pantry/mudroom with an opening over the sink to peer into an inviting sunroom beyond. This lovely corner space is wrapped in oversized windows to take in the views, and features a wood burning stove for cozy winter days and nights. Across the center hall from the kitchen is the ample living room centered on the second wood burning fireplace, with mountain views at the front of the house and views of the wildflower meadow and pool area at the back. The living room leads to a master bedroom wing with a handsome bath en-suite and well-appointed walk in closet. Throughout the entirety of the home, there are beautiful hard wood floors with radiant heat, central cooling and glorious views from every room. All of the systems are new, including a 400Amp electrical service with standby Generac generator, all new plumbing and well, with whole house filter and water softener and whole-house ERV Fresh Air and Dehumidifier system installed. Two well-constructed porches were restored to the home and run the length of both the front and rear of the house for gathering with friends or just relaxing and taking in the views.
Courtesy: Columbia County RE Specialist
518-325-9784
Unique investment opportunity in the hamlet of Hillsdale. This new-to-the-market commercial/residential property has been meticulously renovated by the current owner, a commercial builder, who over-engineered the project with high-end features throughout. The property consists of four distinct rental units: 2666 Route 23, Main (Blue) Building - First-Floor Commercial Unit Right Side: 360 sq. ft. (currently Antique Shop) - Second-Floor Residential Apartment: Two bedrooms, 737 sq. ft. (currently VERY LUCRATIVE AirBnB) - Two-Story Commercial Unit Left Side: 766 sq. ft. (currently leased 12+/- mo. to State) Red Barn Building - Two-Story Barn Renovation: Two bedrooms, one bath, 791 sq. ft. (currently VERY LUCRATIVE AirBnB) Main Building: Circa 1880 3 Units ~ 2 Commercial Retails and a Fully Furnished turn key AirBnB/Apartment In the Berkshire/Taconic Mtn area, main building was fully renovated creating retail shops and a sophisticated but casually comfortable 2 BR apt. saving many of the original building features. Efficiency kitchen (convention microwave, cooktop, Mr. Coffee, all utensils, cookware, DW) with a W/D, marble bath, sleeps 4 , cable TV and internet. Bright and airy, full AC. Children friendly with tamper proof outlets, central station fire alarm system, CO detector. Offered Fully Furnished. The Carriage House ~ Private Residence AirBnB This structure was built around 1845 as a carriage house for the main building. The building's structure was completely reconstructed with great sensitivity to the unique features of the original use. The hay loft floor remains as a ceiling for the 1st floor although it is now 11 ft high. The 1st floor consists of an open plan living space with a washer/dryer combo tucked tastefully in the utility space. The 2nd floor has 2 bedrooms and a bathroom highlighted by the exposed timber roof framing. The space; the effort to maintain the 1845 appeal of the space is very successful with finishes utilizing reclaimed materials from the main house renovation as well as much from the original carriage house. The original siding has been incorporated into the interior walls abutting the timber framed structure. The bathroom is finished with Carrera marble tile shower walls and floor. Five panel mahogany doors complete the charming ambiance of the space. The Barn is highly energy efficient with spray foam insulation, new Pella windows and heat pump supplying environmental comfort. Immediately outside the entrance is a blue-stone paver patio with dining table chairs, Adirondack seating and gas grill. This overlooks a calming view of gardens and neighboring backyards. Offered Fully Furnished. Five Start AirBnB stats upon request. Purchased in 2012, transformed into sophisticated retail/residential, vacation getaway spaces, while preserving many original architectural features - see list of improvements. Basement of main building could easily be converted into additional living space. Features include high ceilings, water already hooked up etc. The location is ideal for a four-season destination, situated near Catamount Ski and Adventure Park, the Copake-Hillsdale Farmers Market, the Harlem Valley Rail Trail (goes all the way to NYC now!), and Taghkanic State Park. It also offers easy access to the dining and entertainment options in Hudson and the Berkshires. This is an exceptional multi-use property for anyone seeking a high-quality investment in Columbia County.
Courtesy: Compass Greater NY LLC
914-238-0676
Custom contemporary home built in 1996 with thoughtful gathering spaces. Main floor has a vaulted ceiling living room with fireplace, open to dining and the eat-in-kitchen. Down a hall to the south end there is the primary suite, a powder room, laundry, the den with a vaulted ceiling and a woodstove and access to the garage. On the north side of the main living room is a large entry foyer, a great room with woodstove and 3/4 bath. Upstairs there are two bedrooms, a hall bath and ample closet space. The lower level has a walkout section with a large bedroom, hall bath and a hall that takes you into the below grade finished area with office, play space and extra room. The screened porch off the entry foyer leads to a very large deck on the east side of the property angled southeast with views and tremendous light. Close to the farm store, Hillsdale center, 20 min to Great Barrington and 30 min to Hudson.
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 . 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.
Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The thoughtfully appointed, updated kitchen flows seamlessly into a generous living area anchored by custom built-ins and a cozy wood-burning fireplace. Wall-to-wall windows grace the formal dining room, ensuring every meal is accompanied by breathtaking scenery. Both the living and dining rooms offer direct access to a sprawling rear deck, perfect for entertaining. A tranquil sun-room provides a versatile space, ideal for a home office or a quiet retreat. Down a private hall, the sleeping wing awaits. The primary suite is a true haven, featuring a second fireplace, a charming window seat for reading, a large walk-in closet, and an en-suite bath. Two additional well-proportioned bedrooms with ample closet space share a pristine hall bathroom. A generous two-car attached garage and a full basement offer abundant storage and convenience right off the main entry.Outside, the 8.3-acre grounds are a serene blend of manicured lawn, wild meadow, and mature plantings. The location is truly stellar: less than five minutes to Catamount Mountain Resort for year-round adventure, and just moments from
Courtesy: Columbia County RE Specialist
518-325-9784
Nestled on a wooded hillside on one of Hillsdale's prettiest country roads is where you will discover this exceptional 2,500 sq.ft. custom-built home. The 5.5-acre parcel sits above Pine Ridge Lane; a lightly travelled country road located just off Mitchell Street in the heart of Hillsdale. Surrounded by nature in every direction, the peaceful, park-like setting is unique and as beautiful as any other we have seen. The spacious three-bedroom, three bath colonial offers numerous design features and accents that bring the outdoors in and fills the home with natural light. The main level features an open floor plan centered around the grand living room with vaulted ceiling and stone fireplace. Off the living room you will find a formal dining room, updated kitchen with center island, breakfast nook and bedroom suite with full bath and walk-in closet. On the second level, there are two additional generously sized bedrooms and a full bath situated off the balcony sitting area. If more living space is desired, the full basement has high ceilings and can easily be finished to create a great room, exercise room or any other space you desire. Outdoors is another area where this property truly shines. Although the parcel size is not over-sized, it's location and setting provide the privacy and seclusion generally only reserved for much larger parcels. Entering the property, you are greeted by an impressive stone wall and stairway leading to the front entrance. A composite deck wraps around the front, side and rear of the property for outdoor enjoyment. A surprisingly large lawn provides an open setting with plenty of sunlight, while the hardwood forest surrounding the house protects is privacy. The woodlands and natural gardens have been meticulously maintained over the years to create the natural setting that helps make this home so uniquely special. All this and more can be found on a quiet dead-end road in Hillsdale that is only a few minutes away from Catamount Ski Area, the HV Rail Trail, Taghkanic State Park and located half-way between Hudson and the Berkshires.
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: 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) ''This listing contains digitally rendered photograph showing a proposed pool and modified landscaping to illustrate the property's architectural potential. These features do not currently exist on the property. Please refer to the included unedited photographs for the true, current physical condition of the lot.''
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.
Courtesy: KW MidHudson
914-962-0007
BACK ON MARKET!! Welcome home to this charming and stylishly updated retreat situated on a spacious, level lot in beautiful Hillsdale, NY! Offering a perfect blend of modern character and country appeal, this home is ideal for those looking for a peaceful getaway with fantastic outdoor space. As you arrive, the striking dark grey exterior, crisp white accents, and charming fenced-in front yard lead you to a welcoming entry. Head inside to find newly finished floors in a bright and airy living room and a stunning custom paneled accent wall that sets a warm, modern tone throughout. The heart of the home flows seamlessly from the living room into the inviting dining area, making it perfect for gathering. Just beyond, the beautifully refreshed kitchen offers sleek dark cabinetry, modern wood-look plank flooring, a stainless-steel double sink, and bright white appliances, ready for you to personalize to your taste. You’ll also find a crisp, updated bathroom showcasing classic white wainscoting, modern fixtures, and a glass-enclosed corner shower. Step outside to discover an expansive rear deck—a perfect spot for outdoor entertaining, summer barbecues, or simply relaxing while overlooking the generous, open backyard. One of the standout features of this property is the fantastic detached garage, complete with a built-in workbench and rustic wood-paneled interior, offering incredible potential for a workshop, hobby space, or ample storage. An additional storage shed in the yard provides even more convenience for all your outdoor equipment. Enjoy the best of country living with unbeatable access to everything the Hudson Valley and neighboring Berkshires and Copake Lake have to offer. Schedule your showing today!
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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.
