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: Compass, Hillsdale
914-327-2777
Nestled on 18+ secluded acres along one of Hillsdale's most bucolic and sought-after roads, this solidly built country home offers endless potential. Located just minutes from the Massachusetts border on the edge of the Berkshires and only 15 minutes from Great Barrington, this property provides the perfect balance of peaceful rural living and convenient access to the region's renowned cultural, dining, and outdoor attractions. The home is filled with warmth and character with beautiful natural wood details throughout. A spacious through-house living room serves as the heart of the home, anchored by a striking stone wood-burning fireplace complete with an indoor grill. A large sunroom extends the living space, offering the perfect spot to enjoy the surrounding landscape in every season. The residence features two bedrooms, two full bathrooms and a half bath, as well as a freshly painted 400+sf attic with heat and air conditioning and 5 windows, providing flexibility for guests and home office space. Approached by a long, meandering gated driveway, the property offers exceptional privacy. The entire acreage is enclosed with deer fencing, creating a secure environment for gardens, pets, or livestock. Outdoor enthusiasts will appreciate the property's many unique features, including a large fenced dog run that could easily accommodate horses or other animals. A picturesque pond, once a beloved local swimming hole, adds to the property's appeal. On the water's edge is a grand double-sided stone fireplace, presenting a remarkable opportunity to create outdoor entertaining and dining overlooking the water. There is a full basement with an integrated garage space currently used as a workshop, a detached two-car garage with substantial storage and extra square footage previously utilized for animals, and a charming pole barn ideal for lawn equipment, hobbies, or additional storage. Recently trenched and updated power and fiber optic and new septic piping. A truly special Hillsdale property offering privacy, natural beauty, and the opportunity to create your own Hudson Valley and Berkshires retreat.
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: 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.
Set just off the banks of Copake Lake and privately positioned on five wooded acres, The Van Bueran House offers a rare blend of modern design, an inground pool, and deeded lake rights to one of Columbia County's most sought-after motorboat lakes. Recently renovated with forever in mind, the home pairs thoughtful design with meaningful infrastructure: white oak and radiant heated floors throughout, a standing seam metal roof, new windows, updated mechanicals, a whole-house generator, a new kitchen, and beautifully reimagined baths. Designed as both an escape from city life and a full embrace of it, this is a home that invites you to slow down, spread out, and immerse yourself in the natural beauty of upstate New York. Curated with an emphasis on generous indoor-outdoor living, the home's design prioritizes flow, light, and connection to its landscape - creating spaces that encourage gathering, movement, and a daily relationship with nature. At the heart of the home, the open living, kitchen, and dining wing is a true centerpiece - wrapped in an oversized deck and surrounded by the forest canopy. Vaulted ceilings, skylights, and expansive sliding and french glass doors flood the space with natural light, while a striking black fireplace anchors the living room. A dining area designed for ten opens directly to the screened porch, while the kitchen introduces a playful pop of color and is centered around an oversized island built for conversation and connection. The main-level primary suite also offers vaulted ceilings and direct deck access - plus an en suite bath with radiant heated floors, a walk-in shower, and warm wood finishes. A second king-sized bedroom and an additional queen bedroom share a beautifully finished full bath (also with radiant heat). The lower level expands with a stylish media and game room, two thoughtfully designed bedrooms, and a full bath with a deep soaking tub. A substantial unfinished storage and laundry area with walk-out access adds practicality without compromising design. Outside, the 40' x 16' pool is tucked privately into the southern side of the property, where mature trees, a pool shed, solo fire pit, and star-filled skies create a secluded summer sanctuary. Below, a third lower deck offers yet another layer of retreat - ideal for slow mornings, outdoor dinners, reading, or yoga. A whole-house generator adds year-round confidence to this peaceful woodland setting. What truly distinguishes this offering is its connection to Copake Lake - one of the Hudson Valley's most coveted recreational enclaves. Residents enjoy access to a private beach, docks, boat slips (based on availability), and the rare luxury of a beloved waterfront restaurant, creating a lake lifestyle that feels both vibrant and effortless. Minutes to Catamount Mountain Resort, Bash Bish Falls, Copake Country Club, and the celebrated dining, shopping, and cultural destinations of Hudson and Great Barrington, this is Hudson Valley living at its best - private, design-forward, and deeply connected to adventure. Under 30 minutes to Amtrak, 35 minutes to Metro North, and under two hours to the George Washington Bridge.
Courtesy: William Pitt Sothebys Int Rlty
203-644-1471
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 the heart of Hillsdale, home to excellent dining like the historic Roe Jan Brewing Co. With Great Barrington, MA, just 20 minutes away and Hudson, NY, a mere 30-minute drive, this exceptional property perfectly balances pastoral tranquility with unbeatable cultural access.
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.
Courtesy: Compass Greater NY, LLC
838-877-8283
Set just off the banks of Copake Lake and privately positioned on five wooded acres, The Van Bueran House offers a rare blend of modern design, an inground pool, and deeded lake rights to one of Columbia County’s most sought-after motorboat lakes. Recently renovated with forever in mind, the home pairs thoughtful design with meaningful infrastructure: white oak and radiant heated floors throughout, a standing seam metal roof, new windows, updated mechanicals, a whole-house generator, a new kitchen, and beautifully reimagined baths. Designed as both an escape from city life and a full embrace of it, this is a home that invites you to slow down, spread out, and immerse yourself in the natural beauty of upstate New York. Curated with an emphasis on generous indoor-outdoor living, the home’s design prioritizes flow, light, and connection to its landscape - creating spaces that encourage gathering, movement, and a daily relationship with nature. At the heart of the home, the open living, kitchen, and dining wing is a true centerpiece - wrapped in an oversized deck and surrounded by the forest canopy. Vaulted ceilings, skylights, and expansive sliding and french glass doors flood the space with natural light, while a striking black fireplace anchors the living room. A dining area designed for ten opens directly to the screened porch, while the kitchen introduces a playful pop of color and is centered around an oversized island built for conversation and connection. The main-level primary suite also offers vaulted ceilings and direct deck access - plus an en suite bath with radiant heated floors, a walk-in shower, and warm wood finishes. A second king-sized bedroom and an additional queen bedroom share a beautifully finished full bath (also with radiant heat). The lower level expands with a stylish media and game room, two thoughtfully designed bedrooms, and a full bath with a deep soaking tub. A substantial unfinished storage and laundry area with walk-out access adds practicality without compromising design. Outside, the 40’ x 16’ pool is tucked privately into the southern side of the property, where mature trees, a pool shed, solo fire pit, and star-filled skies create a secluded summer sanctuary. Below, a third lower deck offers yet another layer of retreat - ideal for slow mornings, outdoor dinners, reading, or yoga. A whole-house generator adds year-round confidence to this peaceful woodland setting. What truly distinguishes this offering is its connection to Copake Lake - one of the Hudson Valley’s most coveted recreational enclaves. Residents enjoy access to a private beach, docks, boat slips (based on availability), and the rare luxury of a beloved waterfront restaurant, creating a lake lifestyle that feels both vibrant and effortless. Minutes to Catamount Mountain Resort, Bash Bish Falls, Copake Country Club, and the celebrated dining, shopping, and cultural destinations of Hudson and Great Barrington, this is Hudson Valley living at its best - private, design-forward, and deeply connected to adventure. Under 30 minutes to Amtrak, 35 minutes to Metro North, and under two hours to the George Washington Bridge.
Welcome to Foxleigh Estate, a designer residence perched high on over 14 private acres on a quiet dead-end road in prime Hillsdale, with sweeping Catskills and Berkshires Mountain views. Entered by a long pea gravel drive framed by stone walls, the fully renovated four-bedroom home features refined interiors, a heated gunite pool, pond, and a spa sanctuary with a sauna, hot tub, and cold plunge positioned to capture the views. Just minutes to skiing and hiking, and with easy access to Hudson, and Great Barrington. At this level of design, setting, and privacy, Foxleigh Estate is without peer in one of the region's most coveted settings. Interiors and architectural updates by celebrated designer Louise Copeland of L.B. Copeland, including a reconfigured floor plan, new kitchen, flooring, lighting, and front portico. Offered with the option to purchase furnished. At this level of design, setting, and privacy, Foxleigh Estate is without peer in the region.
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: 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: Columbia County RE Specialist
518-325-9784
51 Sabeff Road is new to the market for the first time since the original owner, Sabcho Sabeff, sold it in 1981. It has been enjoyed as a family compound by the current owners since that time. Entering the property from Sabeff Road, a town maintained dead end road in the heart of Hillsdale, is like taking a step back in time. This spectacular parcel is a nice mix of flat lawn and slightly sloping woodland. The entire 11-acre parcel is surrounded by woods, offering uncompromised privacy and seclusion. Because of its primitive uniqueness, this is the special type of setting that has become priceless in today's market. The single story home is highlighted by a stone foundation and chimney, wide-board pine floors, new well and water system, wood siding and 2-car attached garage. It offers 1,750 square feet of living space, with 3 bedrooms and 2 baths. The floor plan centers around the original stone fireplace located in the open living room/dining room/kitchen area. Additionally, the home features a large great room overlooking the front yard and an enclosed porch that overlooks the deep side yard. An ideal candidate for expansion, accessory dwelling unit or an updating project. There is more than enough room to serve as a family compound, without sacrificing privacy. A beautiful classic barn and newly drilled well and water system are already in place. The future for this special property, will be at the discretion of the next owner's vision.
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!
Courtesy: KW Mid-Hudson
914-962-0007
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 a bright and airy living room featuring original hardwood floors 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!
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: 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.
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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.
