84 properties for sale in Green River, Hillsdale town Columbia County New York

A Classic Modern Farmhouse with Incredible Views. This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above. The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings. The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a welcoming foyer, a serene bedroom suite, and an elegant formal living room. Upstairs, the master suite is a haven of sophistication, complete with a stone fireplace and ample space for relaxation. Two additional gue

Welcome to Bald Mountain Estate, an extraordinary private compound spanning 85 breathtaking acres overlooking the Hudson Valley and the Berkshire Hills. This four-building, ultra-contemporary estate epitomizes modern country luxury, featuring floor-to-ceiling glass walls and a steel infrastructure that creates a distinctive blend of rustic elegance and architectural sophistication. The open-concept main residence seamlessly integrates indoor-outdoor living and showcases three fireplaces, reclaimed wood floors, and a striking maple staircase. Nearby, two custom guest houses, a workshop, two serene ponds, and a stunning Gunite pool framed by dramatic stone walls complete the compound. Meandering hiking trails traverse the property, leading to the mountaintop and its breathtaking panoramic views of the Catskill, Berkshire, and Taconic Mountain Ranges. This elevated site also presents a magnificent opportunity for a new main residence, with the existing structures preserved as guest cottag

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 livi

Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County’s most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a constant play of light throughout the interior and frame the surrounding landscape as living art. Inside, the soaring cupola-topped ceiling and radiant-heated polished-concrete floors create a calming, loft-like atmosphere, anchored by a dramatic floating propane fireplace. The designer kitchen integrates seamlessly into the open living and dining spaces, making the home equally suited for quiet evenings or stylish entertaining. Two airy, loft-style sleeping areas, and two sleek glass-and-steel baths complete the thoughtfully curated layout. Every element of the home blends sophistication with simpli

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

Sunset meadow. Where Architecture and Nature Exist in Perfect Balance As the private drive gently climbs through the landscape, a sense of calm settles in. Perfectly sited on over 30 private acres of rolling lawns, flowering gardens, open meadows, and woodlands, this exceptional Kate Johns-designed country residence reveals itself, embracing commanding western Catskill Mountain views, spectacular sunsets, complete privacy, and nature's ever-changing beauty. An expansive front porch welcomes you before you even step inside, hinting at the gracious living spaces beyond, where soaring ceilings, walls of glass, wide-plank floors, and abundant natural light frame breathtaking vistas. Flooded with natural light, gracious living and dining spaces unfold beneath soaring ceilings, where a grand stone fireplace, timeless architectural details, and French doors opening to the stone patio create an atmosphere that is both elegant and inviting. Nearly every room enjoys breathtaking western Catskill

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

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)

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

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

Camp Dugway A home that evokes the great camps of the Adirondacks within 2 hours of Manhattan. Cross the bridge over a babbling brook to a setting straight out of a Cooper novel. Three cascading waterfalls frame the view. The pond sits just off the bluestone patio. Inside a blend of craftsman style and great camp ambiance in every room. The fieldstone in the fireplace came from the land as did much of the wood used in the flooring and panels. The rooms are of a grand scale, with window placement and size designed to compliment nature and splash light. The living room is anchored by the fireplace, the dining flows nicely from the kitchen. The kitchen is made to prepare a feast with room for as many cooks as necessary. The first floor main bedroom opens to the outside patio with a deep tub for long soaks of contemplation. Upstairs three more bedrooms and the game room, full of light and mischief. Downstairs its movie time in the theater with cinema seating and lighting. A home gym for we

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 ric

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

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

Newly renovated single floor home in Housatonic, just minutes from downtown Great Barrington, Tanglewood, and everything the Berkshires have to offer. With direct access to the Rail Trail, this move-in ready home is set on. 93 acres, the property features a spacious yard and greenhouse, offering plenty of room to relax, garden, or entertain. The updated kitchen features stone countertops, stainless steel appliances, an induction range, and new LVP flooring. Both bathrooms have been fully renovated with Schluter waterproof systems. Additional upgrades include smart Lutron lighting with Alexa control, a Rheem smart hot water heater, Ring cameras, new 200-amp electrical service, a new driveway and retaining wall, irrigation system, freshly painted exterior, and a new septic installed in 2025!

Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches. All to take in the beautiful Catskills. Stepping through the front door of a wide covered front porch, you'll find an open plan kitchen, dining & living room. The heart of the home, made cozy in winter by an efficient wood stove. The first floor also includes a mud room, office, powder room, laundry room and den. However, it is the 600 sq ft'Great Room', with windows on 3 sides that immerse you in the ever-shifting displays of nature and the Catskill range. Upstairs you'll find 3 generous sized bedrooms and 2 full baths including a primary suite with walk-in closet room. The pond, designed by famed UK pool master

Light-filled contemporary cape built in 2020, this Stockbridge home features an open floor plan anchored by a great room with a gourmet kitchen, dining area & living room. Two spacious first-floor bedrooms share a full bath, while the expansive second-floor primary suite offers a luxurious spa bathroom & a balcony overlooking the living area. The four-season sunroom (heated & cooled for year-round use) opens to the level backyard. Lovely front entrance with Bluestone steps into an ample mudroom. Enjoy year-round comfort with zone-controlled mini-splits. Close to vibrant Great Barrington, Stockbridge & Lenox. A quick drive to Tanglewood, cultural venues, & abundant outdoor recreation including hiking & lakes, this modern retreat blends style, comfort, and an exceptional Berkshires location

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 sea

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 sea

Manufactured home at the end of a quiet lane. Nearly 5 acres of tranquility. Close to State Forest and Beebe Hill for hiking. Two bedrooms with two full baths. Open floor plan. Easy maintenance. Enclosed porch and nice deck. Two hundred square foot enclosed. Doesn't get any more private than this. Shed for storage. Woodstove for the fall and winter nights. Cleared spot perfect for gardening or camping

Tucked down a private road and high in the hills of northern Hillsdale, this well-built home offers sweeping mountain views, a beautiful pool, and more than 12 completely private acres-all within 10 minutes of town and 15 minutes from Great Barrington. The house is outfitted with thoughtful details that make country living comfortable and easy-central cooling, ample storage in all the right places, a two-car garage that opens into a mudroom and laundry room, en-suite baths in every bedroom, and a whole-house generator. The first-floor layout flows seamlessly, with two separate living rooms: one with a gas fireplace just off the dining room, and another farther down the hall with easy access to the guest bath. The kitchen is appointed with beautiful new soapstone countertops, a deep fireclay sink from Limoges, France, and a new gas range. At the end of the hall, the spacious and serene primary suite features a walk-in closet designed for two and a full bath with a walk-in shower and ove

With a view as far as the eye can see, 65 Meadow Lane, Hillsdale never fails to amaze from sunrise to sunset, as a full moon lights up your bedroom; hawks fly past wandering clouds, the fiery yellow and burnt red leaves of autumn and the pine trees dripping with snow like confectionary sugar in a winter wonderland. The only sounds you hear are woodpeckers and wild turkeys and your heartbeat slowing down in the serenity. It's a comfortable and comforting home to escape to and share with family and friends. Private & quiet. 3 bedrooms, 3 baths, 2 woodburning Fireplaces, shared swim/fishing pond, just under 10 acres with long distant views of mountains, water and beauty. Finished basement with woodstove & bathroom. A place to sit and be in peace

Offered with Seller Financing, this Majestic Tudor Berkshire Estate sits on 71 Acres atop Tom Ball Mountain in quaint Alford, MA. Privacy and Breathtaking views. Formal Entry and Foyer. Stately Living Room and Dining Room. Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. 2 Bedroom Tudor Guest House w beamed ceilings and full amenities. Manicured grounds, infinity Pool and Hot Tub, Pool House with full Bath, Tennis Court and Pickleball Court. 7 Garages and additional Barn. Exquisite architectural touches, state-of-the-art home technology and security, in the most peaceful of surroundings. Easy access by road, rail and private Airport. Close to Tanglewood and Berkshire attractions. Fully Furnished and ready to enjoy

A true haven of tranquility and beauty in the hills of Austerlitz, located just minutes from the hamlet of Spencertown. Sweeping views of the rolling hills form a perfect backdrop to the stunning pond, all of which can be enjoyed from the ideally placed front porch of this delightful home. The 17 private acres feature a scenic mix of woodlands and open spaces, complete with quiet trails to explore and a winding creek to follow. You will never want to leave the shade of the spacious front porch, except to swim in the crystal-clear pond or to barbecue on the private back deck. Completely restored under an architect's guidance, the residence was thoughtfully sited for absolute privacy, set far back from the road and secluded by mature trees. While offering total seclusion, convenience is just around the corner. A great cup of coffee is only minutes away in the village of Chatham, and the famous Hawthorne Valley Farm Store is just an eight-minute drive

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