Courtesy: Red Apple Realty
518-851-9601
Recently Renovated Hillsdale Gem! Welcome to this beautifully renovated 3-bedroom home in the heart of Hillsdale, blending modern comfort with timeless charm. The bright, welcoming kitchen features quartz countertops, high-end vinyl plank flooring, and updated appliances that balance style and functionality. A spacious living room offers plenty of room for entertaining, with space for a dining area complemented by a built-in china cupboard. A separate family room features a cozy wood stove and glass doors that open onto an 18' x 18' stone patio, perfect for summertime relaxation and gatherings. Two main-level bedrooms are served by an updated 3/4 bath, while a spacious third room upstairs offers flexibility as an additional bedroom or home office. The entryway mudroom adds everyday convenience with laundry facilities, built-in storage, and cubbies. Outside, the private backyard provides a peaceful setting for morning coffee, entertaining, or simply unwinding. The 1-acre property includes a fenced-in area, offering outdoor space to enjoy throughout the seasons. Recent improvements include freshly installed siding, a newer roof, and a brand-new septic tank, adding lasting value and peace of mind. Whether you're seeking a weekend escape or a full-time residence, this turnkey home is ready for its next chapter in a peaceful Hudson Valley setting.
Courtesy: Copake Lake Realty Corp.
518-325-3921
Surrounded on three sides by Audubon Society land, this 3 bedroom, 2 full bath home offers a combination of beautiful views and everyday conveniences. Set on one acre, the property looks out front its deck across protected wetlands where great blue heron, ducks, geese and an abundance of other birds and wildlife can be enjoyed throughout the seasons. The wooded Rheinstrom hillside provides a beautiful natural backdrop. Inside, the home features an eat-in kitchen and a dining room with glass doors opening to the views, bringing the surrounding landscape into the heart of the home. The lower level offers a large gathering room, perfect for entertaining, relaxing or additional living space. There is also a convenient one car under garage. Shopping is just one mile away. Ideally located midway between Great Barrington and Hudson this property offers shops, arts, culture and many recreational opportunities of the Berkshires and Hudson Valley.
Courtesy: Houlihan Lawrence Inc.
518-822-0300
This architect-owned and thoughtfully renovated 1880s Hudson Valley farmhouse in the hamlet of Hillsdale effortlessly brings together historic character and contemporary design. Original details and a striking modern addition create a home that feels timeless, warm, and modern. Distinctive, beautifully maintained, and move-in ready, this home is perfect for weekend getaways or year-round living offering privacy, and convenience--set in one of the region's most sought-after landscapes. Enter the dramatic addition with its 12-foot ceilings and abundant natural light -- built to expand the living and dining spaces which flow into the beautifully designed kitchen. Thoughtful details and an intuitive layout make the heart of the home equally inviting for both quiet mornings and effortless entertaining. Approximately 1,800 square feet, the three-bedroom, two-bath home is layered with original character, including hand-hewn beams and hardwood floors. A wood-burning stove adds warmth and atmosphere on winter evenings, while two well-appointed bathrooms feature custom details and generous storage. The home sits on 1.3 acres. The convenient mudroom off the kitchen hallway, complete with washer and dryer, provides a practical transition from country life to indoors. Throughout, ample storage and carefully considered spaces make the home remarkably functional without compromising its relaxed, welcoming feel. Outside, the gardens are as appealing as the house itself. Stone walls, mature plantings, generous flower beds, and a spacious wood deck create a series of inviting outdoor spaces for summer barbecues, long afternoons, and enjoying the changing seasons. An upstate barn, ready for its next chapter, adds another layer of character and possibility. The location offers an exceptional balance of privacy and access. Catamount Ski Resort and the Harlem Valley Rail Trail are just minutes away, while Great Barrington is less than 20 minutes by car and Hudson and the Amtrak station are approximately 30 minutes away. Manhattan is a little over two hours by car, or accessible by train to Grand Central, making this an ideal year-round home and an effortless weekend escape.
Courtesy: Realmart Realty, LLC
888-362-6543
Updated home on 1.4 acres offering 2,430 sq ft of living space. Major improvements completed within the last 5 years include roof, plumbing, flooring, kitchen updates with oak countertops, cabinets, and appliances, log siding, and more. Features a partially finished basement with a bedroom and rec room potential. New septic system installed approximately 2 years ago, plus a newer well pressure pump. Second-floor bathroom is partially finished and awaiting final touches. Great opportunity to complete remaining updates and make this property your own.
Courtesy: The Kinderhook Group, Inc.
518-751-4444
Where Nature and Serenity Take Center Stage! At the end of a private road, a magical country retreat awaits. Offered with two lots totaling over 10 acres, this secluded sanctuary brings together tranquility, natural beauty, and privacy. A winding gravel drive leads to the home, framed by colorful gardens and two picturesque ponds. A stone pathway meanders through vibrant flowers and lush greenery, with bluestone steps leading to the front door. An unforgettable first impression. The current owners are only the second owners of the property, and much of what makes it so special is their creation. Since purchasing the home, they have added the sunroom, decking, ponds, and shed, along with the extensive landscaping and gardens that have transformed the property into the retreat of today. Inside, character and comfort complement the beauty outdoors. The open kitchen with center island flows into the family room, where a wood stove adds charm. Ideal for entertaining, the layout allows you to be part of the conversation. Glass doors open to a wooden deck overlooking a grassy lawn and a newly repaired stone patio. Seasonal winter views from the back of the house add to the beautiful setting. The first floor offers a bedroom or home office, a full bath with laundry closet, a dining room with wood-burning fireplace, and a spectacular sunroom wrapped in three walls of windows. Flooded with natural light, the sunroom's windows frame the changing seasons like a living work of art. A convenient gas stove makes it an inviting year-round retreat, while the covered outdoor deck is perfect for a good book or afternoon nap. Upstairs, the primary features an en-suite bath and private balcony overlooking the grounds, with a guest bath as well. The true magic of this property lies outdoors. Wander through spectacular gardens, relax beside the ponds, or discover the creek just beyond. Follow the land uphill behind the ponds to a beautiful vantage point offering sweeping views and unforgettable sunsets. With over 10 acres to explore, nature and tranquility are yours to enjoy. Despite its seclusion, the location offers exceptional convenience: 15 minutes to Great Barrington and the Berkshires, 25 minutes to Hudson's Warren Street and Amtrak, 15 minutes to the Taconic State Parkway, and approximately two hours north of New York City. Two lots. Over 10 private acres. Spectacular gardens, picturesque ponds and creek, and unforgettable sunsets. Your own private world to reconnect with nature, embrace serenity, and rejuvenate. Please respect the current owners' privacy and refrain from visiting the property without a confirmed appointment. Thank you for your understanding.
Courtesy: Compass Greater NY, LLC
914-238-0676
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: Copake Lake Realty Corp.
518-325-9741
COUNTRY CONTEMPORARY RANCH ON 9.5 ACRES WITH FOREVER WILD VIEWS A truly special country getaway, this distinctive 3-bedroom, 2-bath contemporary home is set on 9.5 beautiful acres with sweeping views of protected farmland and forever-wild Audubon sanctuary lands. Designed to embrace its natural surroundings, the home enjoys southern exposure and passive solar orientation, creating a warm and inviting connection to the landscape. The primary bedroom occupies a private loft area with its own sitting area and deck, offering a peaceful retreat and beautiful views. Two additional bedrooms are conveniently located on the main level. The contemporary design features numerous custom-built elements throughout, along with a fireplace, spacious family room, and an interior hot tub--perfect for relaxing after a day outdoors. Outside, enjoy an in-ground pool, a small pond, mature fruit trees, and plenty of space for gardens. The property also includes two run-in barns. Open acreage with endless possibilities for gardening, animals, recreation, or simply enjoying the tranquility of country living. Ideally located just minutes from the Taconic State Parkway and approximately 10 minutes to the Berkshires, this property offers the rare combination of privacy, protected views, recreational amenities, and convenient access to the best of the Hudson Valley and Berkshires. A unique country property offering privacy, custom character, and room to enjoy the land--your own peaceful retreat in the country
Courtesy: Corcoran Country Living
845-876-6676
Located on a quiet country cul-de-sac in Hillsdale, this spacious three-bedroom home sits on 4.7 private acres. One of just three residences along the road, it enjoys an exceptionally peaceful setting, with open lawn, well-maintained woods, trails, and old stone walls. Inside, the living space provides generously proportioned rooms and abundant natural light. The living room centers around a stone fireplace, with large windows and direct access to an expansive back deck, ideal for outdoor dining, grilling, or simply enjoying the surroundings. The generously sized kitchen includes a large eat-in area, while a separate dining room offers additional space for gathering. The primary suite is notably spacious, with an en-suite bath featuring a soaking tub and separate shower. Two additional well-sized bedrooms, a second full bath, and a half bath complete the main level. A full walkout lower level spans the footprint of the house, with high ceilings, multiple windows, and French doors leading outside. Currently unfinished, it offers potential for additional living space, a studio, gym, or recreation room. The home also has an attached two-car garage. A separate two-car garage/workshop offers even more flexibility for creative pursuits, projects, or additional storage. For all its privacy, the property is exceptionally well positioned, with the village of Hillsdale, Catamount, and the Harlem Valley Rail Trail all just five minutes away. Copake is also nearby, with both Hudson and Great Barrington within easy reach.
Courtesy: Houlihan Lawrence, Inc
518-822-0300
Welcome to Bons Reves House, a beautifully designed escape tucked away on nearly seven acres in the most desirable part of the Austerlitz hills. Built in 1985 and meticulously renovated and expanded by a top builder in 2012 and again in 2025, this 4-bedroom, 3.5-bath contemporary home feels like a luxury treehouse hidden among mature hardwoods and surrounded by large estates and high-end residences. Custom millwork, natural stone and wood surfaces, bespoke plaster treatments, and designer-chosen paint colors all speak to exceptional quality. The gracious, flowing layout offers plenty of room for gathering, and bedrooms tucked into separate wings create privacy and practicality. This is a home built as much for weekend entertaining as it is for quiet days spent resting and recharging. On the first floor, a renovated chef's kitchen with stone countertops, custom cabinetry, multiple prep areas, and an island breakfast bar make it a true country kitchen, with plenty of room for gatherings and holidays. It flows into a Thanksgiving-sized dining area and a large, inviting living room centered around a cozy wood burning fireplace. Just off the kitchen, a newly built four-season sunroom looks out through oversized windows onto treetops and the ridgeline beyond. A mudroom with laundry, a full bath, and a powder room round out this level. Up one set of stairs, the primary suite has vaulted ceiling, multiple closets, and a full bath with a dramatic architectural sensibility. A second staircase off the kitchen leads to two more bedrooms and a full bath. Down on the lower level, an additional bedroom joins a studio or work space, an exercise area, and a newly built window-lined sitting room, offering room to spread out or tuck away. Outside, the wraparound Trex deck, front porch, fenced garden, handbuilt stone walls, and professionally landscaped grounds create a storybook atmosphere for outdoor living. The wooded acreage surrounding the home creates a natural buffer for privacy and quiet. Recent upgrades reflect real investment in the property: new windows, six new heat pumps, a recently replaced roof, a generator, a new garage door, and a freshly painted interior and exterior. The location suits both a weekend retreat and a full-time home. Just 15 minutes from Chatham, 20 to Great Barrington, MA, 35 minutes to Hudson, 45 minutes to Albany, and two-and-a-half hours to New York City, Bons Reves House puts summer evenings at Tanglewood, a movie night in Chatham, dinner out, and gallery walks through Great Barrington and Hudson all within easy reach. Local golf courses and cycling routes round out the list of ways to spend a day here. Convenient to the region's best amenities and attractions, the home still feels hidden away from the world.
Courtesy: Columbia County RE Specialist
518-325-9784
PRIVATE SETTING!! Cape Cod style home, built in 2000, 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: Douglas Elliman Real Estate
914-232-3700
There are beautiful homes in the Hudson Valley, and then there are properties that seem to occupy a world entirely their own. Set at one of the most extraordinary vantage points in the region, this exceptional contemporary estate presides over 135 private acres with sweeping, unobstructed views across the Hudson Valley to the Catskill Mountains. The sense of scale is remarkable: open sky, rolling land, distant mountains, and complete privacy in every direction—yet Hudson and Great Barrington are each only 25 minutes away. The residence was designed around this landscape; dramatic walls of glass frame the Catskills throughout the house, while soaring ceilings and expansive, open living spaces give the interiors a sense of volume without sacrificing warmth. Living, dining, and kitchen spaces unfold effortlessly toward the terrace and infinity pool, where the water appears to disappear into the mountains beyond. The entire home lives on a single level, an increasingly rare luxury at this scale. Two primary suites and three additional ensuite bedrooms create five beautifully private bedroom suites, equally suited to intimate everyday living or a house full of family and friends. Throughout, the architecture is sophisticated but restrained, allowing the extraordinary setting to remain the focus. And the house is only the beginning. The estate encompasses 135 acres of lawns, fields, woods, and private trails, creating a property that can be experienced as much as admired. A large, crystal-clear swimming pond offers an idyllic counterpoint to the infinity pool. Miles of trails wind through the acreage for riding, hiking, and exploring, while a barn and riding arena establish the property as a true equestrian retreat. A separate two-bedroom cottage provides charming guest accommodations, while a carriage house with its own apartment creates additional flexibility for guests, staff, an office, or studio. What ultimately distinguishes this property, however, is something photographs and specifications can only begin to convey: the feeling of being here. Morning light moving across 135 private acres. Long afternoons by the pond. Horses on the trails. Dinner overlooking the mountains. And, each evening, the sun setting behind the Catskills from an infinity pool seemingly suspended above the Hudson Valley. It is extraordinarily private without being isolated, grand without being ostentatious, and remarkably complete without feeling overdone. Properties of this caliber are exceedingly difficult to create—and even harder to find. Just 25 minutes from the restaurants, galleries, shops, and cultural life, this is not simply a country house. It is one of those rare places that makes leaving the city feel like arriving somewhere else entirely.
Courtesy: Stone House Properties, LLC
413-232-4253
There are beautiful homes in the Hudson Valley, and then there are properties that seem to occupy a world entirely their own. Set at one of the most extraordinary vantage points in the region, this exceptional contemporary estate presides over 135 private acres with sweeping, unobstructed views across the Hudson Valley to the Catskill Mountains. The sense of scale is remarkable: open sky, rolling land, distant mountains, and complete privacy in every direction--yet Hudson and Great Barrington are each only 25 minutes away. The residence was designed around this landscape; dramatic walls of glass frame the Catskills throughout the house, while soaring ceilings and expansive, open living spaces give the interiors a sense of volume without sacrificing warmth. Living, dining, and kitchen spaces unfold effortlessly toward the terrace and infinity pool, where the water appears to disappear into the mountains beyond. The entire home lives on a single level, an increasingly rare luxury at this scale. Two primary suites and three additional ensuite bedrooms create five beautifully private bedroom suites, equally suited to intimate everyday living or a house full of family and friends. Throughout, the architecture is sophisticated but restrained, allowing the extraordinary setting to remain the focus. And the house is only the beginning. The estate encompasses 135 acres of lawns, fields, woods, and private trails, creating a property that can be experienced as much as admired. A large, crystal-clear swimming pond offers an idyllic counterpoint to the infinity pool. Miles of trails wind through the acreage for riding, hiking, and exploring, while a barn and riding arena establish the property as a true equestrian retreat. A separate two-bedroom cottage provides charming guest accommodations, while a carriage house with its own apartment creates additional flexibility for guests, staff, an office, or studio. What ultimately distinguishes this property, however, is something photographs and specifications can only begin to convey: the feeling of being here. Morning light moving across 135 private acres. Long afternoons by the pond. Horses on the trails. Dinner overlooking the mountains. And, each evening, the sun setting behind the Catskills from an infinity pool seemingly suspended above the Hudson Valley. It is extraordinarily private without being isolated, grand without being ostentatious, and remarkably complete without feeling overdone. Properties of this caliber are exceedingly difficult to create--and even harder to find. Just 25 minutes from the restaurants, galleries, shops, and cultural life, this is not simply a country house. It is one of those rare places that makes leaving the city feel like arriving somewhere else entirely.
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: Mahar Real Estate, LLC
518-965-1465
Some places announce themselves. This one waits for you at the end of a quiet drive, set well back from the road on a full acre where mature pines close in and the outside world falls away. A green metal roof sits beneath those pines, and the wood construction gives the house a warmth and character that new builds simply cannot copy. Inside, the 2020 renovation did the heavy lifting so you do not have to. Mini splits handle the heating and cooling, the home runs entirely on electric, and two full baths keep the mornings easy. Two bedrooms anchor the layout, and a flexible space on the main level can become a third bedroom, a primary suite, or a home office, whatever your life calls for. The floor plan bends to the way you live rather than the other way around. Step outside and you are close to Hillsdale and the rail trail, with morning walks, bike rides, and an easy afternoon in town waiting for you. Route 22 is right there when you need it, while the pines keep your evenings relaxed and your privacy intact. Whether you want a home to settle into, a weekend retreat, or a property that can work as a rental where local rules allow, the setting and the condition make it easy to picture. Real bones, a smart renovation, and an acre to call your own. Come see it for yourself and schedule your showing today.
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: Berkshire Hathaway HomeService
518-758-1300
PRICE REDUCTION - Under 300,000 dollars on Copake Lake! Welcome to 81 SW Colony Road, a charming 2-bedroom, 1-bath bungalow now offered at a newly adjusted price point that makes owning a piece of Columbia County paradise more accessible than ever. Experience the quintessential upstate lifestyle just over two hours from New York City and 30 minutes from both the Hudson and Wassaic train stations--perfect for a weekend escape, summer lake house, or year-round getaway. Take an immediate look inside with our 3D Virtual Tour on Homes.com to explore this unique property, which boasts 15 feet of coveted, deeded access to the pristine, 425-acre waters of Copake Lake. Adventure awaits in every direction, putting you minutes from skiing at Catamount Mountain Resort, golfing at the Copake Country Club, hiking at Bash Bish Falls, and exploring the vibrant culture, dining, and boutiques of the Hudson Valley and Berkshires. Offered in ''as-is'' condition, this home represents an opportunity to customize, modernize, and build immediate equity--schedule your tour today and secure your ultimate cozy getaway before the ski season hits!
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: 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.
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: 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: 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.
