Pine Plains NY Real Estate & Homes for Sale

Historic 1880s Farmhouse with Expansive Acreage Step back in time with this spacious 1880s farmhouse, enhanced by 20th-century additions, featuring soaring ceilings and beautiful original woodwork. While the home requires extensive updates, its charm and potential are unmatched. Set on 65 acres of pristine land, the property offers a pond, a solid barn, an open meadow, and peaceful woodlands that promise endless outdoor possibilities. Tucked away in the rural beauty of Pine Plains, yet conveniently close to the region's wineries, breweries, golf courses, and recreational pursuits like skiing, biking, and hiking. This is the perfect opportunity to create your dream home while enjoying all the countryside has to offer.

This exceptional property offers a unique blend of modern living, luxury and rural tranquility. Fully renovated the estate features a 5100-square-foot main residence, along with a 750-square-foot detached one-bedroom guest apartment located on 13.8 acres. Thoughtfully designed for both comfortable living and entertaining, the home boasts a spacious eat-in kitchen equipped with high-end appliances, seamlessly flowing into the dining and living areas, all framed by breathtaking views of rolling hills. A cozy TV room completes the main floor. With six bedrooms, four full baths, and one half-bath the home offers ample space for family & friends. The primary suite and two additional ensuite bedrooms are conveniently located on the entry level, while the third floor includes three more bedrooms, a bath, and a library, all easily accessible by elevator. Outside, the property's grounds feature expansive lawns and ample patio spaces offering panoramic views of Stissing Mountain and stunning sunset vistas. Located minutes from Pine Plains.

You wanted charm? This vintage 1903 village home in Pine Plains, NY once served as both the town pharmacy and library, and many of the bookshelves and apothecary drawers remain. The large home on a landscaped half acre is filled with period details: wood moldings, original door knobs and intricate iron hardware, a carved mantelpiece, and several built-ins. And under the carpets are beautiful wood floors. Entered from either of two covered porches, the first floor has a living room, library, dining room, laundry room, powder room and eat-in kitchen. Upstairs are four bedrooms, a study, and a full bath with a spacious walk in closet. While the house is in move-in condition, updating the kitchen and baths will make the home really shine. The fenced-in yard has gardens, a wide-open lawn and a barn with loft that serves as a garage and workshop. Steps away from popular local restaurants and the Stissing Center for the Arts, this property is right in the heart of this up-and-coming town.

A quaint antique home the hamlet ofGallatinville, NY. This 1820 home on .68 acres is loaded with quirky charm. With vintage wallpaper, lots of built-in cabinets and bookshelves, the 3-bedroom 1-bath house is as homey as they get. From the glassed-in porch, you step into a cozy entry hall, then into a large dining room. The country kitchen and comfortable living room with wood burning fireplace insert are off the dining room, and the bathroom is on the ground floor too. Upstairs are three bedrooms and a sitting area that can be converted to a bath or furnished as a library or study. In the shade of the trees surrounding the house are a patio, an old root cellar, a stone barbecue and a raised bed vegetable garden. A two-car garage is tucked into the hillside and there's ample parking for additional cars. Once lovingly landscaped, the property has been little-used for a couple of years, but a little care will bring the gardens back to life. Come check it out!

Check out this multi family home with a detached garage and 2 bedroom apartment in the heart of Pine Plains. This property will appeal to a wide range of buyers. Whether you are looking for a primary residence with some income potential or a multi-family investment, here's your chance. The main house is a 3 bedroom, 1 bath, two story home. The first floor contains a good sized galley style kitchen, dining room and large living room. Upstairs you'll find three bedrooms and one bathroom. The largest of the bedrooms has a great walk-in closet. Tile in the kitchen, otherwise wood floors throughout. The detached garage has a spacious two bedroom, one bathroom apartment above. Both the house and apartment are currently occupied by tenants. Shops, dining, entertainment, hiking trails and essentials are all walkable from this property.

Stretching across the top of 29 wildflower-blanketed acres on the southern ridge of Winchell Mountain, w/commanding Catskills views, lies High View Farm. Inspired by the rolling farmland & expansive blue skies of this very special part of the Hudson Valley, the Architectural & Interior Design duo HallidayGreer collaborated with Architect Graydon Yearick & LaGuardia Design Group Landscape Architects to create a one-of-a-kind living experience. Using sustainable natural materials & state-of-the-art building technology, High View Farm is a perfect synthesis of contemporary modernism & rural barn. Working primarily with local artisans, they have created the ultimate combination of comfort & understated luxury. Relying on the endless power of the sun & the constant, cool temperature of geothermal energy they've realized a passive, architecturally-inspired EcoLux compound that will excite and endure for generations. The 5900 sf, 5 BR/5 BA main house has 3 primary suites and 2 additional ensuite guest rooms. The baths are all appointed with Waterworks fixtures & custom cabinets. The bedrooms, all with spectacular views, are generously proportioned with custom millwork closets with oak interiors. The kitchen is a chef's dream with an AGA Mercury induction stove, a Thermador fridge, an appliance pantry, 2 dishwashers, full butler's pantry with wine refrigeration, and a Miele integrated coffee system. The great room has a masonry fireplace & dining for 14 people. The ground floor has a Tonal Smart personal training machine, free weights, a yoga/stretching area, surround-sound cinema, and a cedar sauna. The piece-de-resistance is the four season indoor/outdoor room with a wood-burning fireplace-a dream for entertaining in a country home. The 50x11ft. saltwater gunite infinity pool, w/sun-shelf & tub spa, overlooks Stissing Mtn. and has a pool house with a ''live'' green roof, full kitchen & bath, & lounge/sleeping area. It's united to the pool by floor-to-ceiling sliding glass panel doors running the length of the pool. A lovely fire pit area for cooler summer & autumn evenings is just past the pool and up the ridge from the built-in BBQ. Closer to the main house, with its own wood-burning built-in BBQ, is the Maple Grove; another idyllic outdoor moment for more elaborate summer parties & alfresco dining. There are 2 add'l structures on the property. First, a 30x40 mortice & tenon barn w/pine & oak hand-hewn beams assembled by local Connecticut barn builders, with room for 2 cars, and a hayloft easily convertible to additional living space. Second, an atmospheric potting shed, inspired by an outbuilding on the grounds of the Parrish Art Museum in Southampton, NY made of pine & clad with perforated stainless steel...a sculptural solution to a utilitarian need. Among the many eco-lux features are fumed white oak wide plank flooring, radiant floor heating, forced geothermal cooling to maintain absolute climate control, ultra-efficient top-quality windows throughout, sustainable radiata pine Abodo siding, and an aesthetically pleasing Tesla solar tile roof that generates almost 20KW of electricity-enough to power the whole property. It also has smart home features like programmable solar roof power generation distribution control, 3 car-charging connections, remote-controlled audio sound system, landscape lighting, window shades, security cameras & automated entry gates. The home comes fully furnished w/bespoke soft furnishings, and fully outfitted, from luxurious sheets to elegant knife sets, all displaying the designers' impeccable style. The interiors blend European & American classical, modernist, & contemporary pieces (primarily sourced from local antique dealers & Hudson Valley craftsmen) in a palette that reflects the rich colors & textures of the surrounding landscape. High View Farm is a homage to the rich history and diversity of the area's rural farming community with an equally engaged commitment to the future

Stretching across the top of 29 wildflower-blanketed acres on the southern ridge of Winchell Mountain, with commanding Catskills views, lies High View Farm. Inspired by the rolling farmland & expansive blue skies of this very special part of the Hudson Valley, the Architectural & Interior Design duo HallidayGreer collaborated with Architect Graydon Yearick & LaGuardia Design Group Landscape Architects to create a one-of-a-kind living experience. Using sustainable natural materials & state-of-the-art building technology, High View Farm is a perfect synthesis of contemporary modernism & rural barn. Working primarily with local artisans, they have created the ultimate combination of comfort & understated luxury. Relying on the endless power of the sun & the constant, cool temperature of geothermal energy they've realized a passive, architecturally-inspired EcoLux compound that will excite and endure for generations. The 5900 sf, 5 BR/5 BA main house has 3 primary suites and 2 additional ensuite guest rooms. The baths are all appointed with Waterworks fixtures & custom cabinets. The bedrooms, all with spectacular views, are generously proportioned with custom millwork closets with oak interiors. The kitchen is a chef's dream with an AGA Mercury induction stove, a Thermador fridge, an appliance pantry, 2 dishwashers, full butler's pantry with wine refrigeration, and a Miele integrated coffee system. The great room has a masonry fireplace & dining for 14 people. The ground floor has a Tonal Smart personal training machine, free weights, a yoga/stretching area, surround-sound cinema, and a cedar sauna. The piece-de-resistance is the four season indoor/outdoor room with a wood-burning fireplace...a dream for entertaining in a country home. The 50 x 11 ft. saltwater gunite infinity pool, w/sun-shelf & tub spa, overlooks Stissing Mtn. and has a 425 sq. ft. heated/cooled pool house with a "live" green roof, full kitchen & bath, & lounge/sleeping area. It's united to the pool by floor-to-ceiling sliding glass panel doors running the length of the pool. A lovely fire pit area for cooler summer & autumn evenings is just past the pool and up the ridge from the built-in BBQ. Closer to the main house, with its own wood-burning built-in BBQ, is the Maple Grove; another idyllic outdoor moment for more elaborate summer parties & alfresco dining. There are 2 additional structures on the property. First, a 30 x 40 mortice & tenon barn with pine & oak hand-hewn beams assembled by local Connecticut barn builders, with room for 2 cars, and a hayloft easily convertible to additional living space. Second, an atmospheric potting shed, inspired by an outbuilding on the grounds of the Parrish Art Museum in Southampton, NY made of pine & clad with perforated stainless steel...a sculptural solution to a utilitarian need. Among the many eco-lux features are fumed white oak wide plank flooring, radiant floor heating, forced geothermal cooling to maintain absolute climate control, ultra-efficient top-quality windows throughout, sustainable radiata pine Abodo siding, and an aesthetically pleasing Tesla solar tile roof that generates almost 20KW of electricity-enough to power the whole property. It also has smart home features like programmable solar roof power generation distribution control, 3 car-charging connections, remote-controlled audio sound system, landscape lighting, window shades, security cameras & automated entry gates. The home comes fully furnished w/bespoke soft furnishings, and fully outfitted, from luxurious sheets to elegant knife sets, all displaying the designers' impeccable style. The interiors blend European & American classical, modernist, & contemporary pieces (primarily sourced from local antique dealers & Hudson Valley craftsmen) in a palette that reflects the rich colors & textures of the surrounding landscape. High View Farm..."Not that far from everywhere but a world away" is a homage to the rich history and diversity of the area's

SILVERNAILS FARM This extraordinary compound on 127 acres blends the historic Hudson Valley with a modern masterpiece main residence. The property boasts two guest cottages featuring five bedrooms, two historic Dutch barns with additional bedrooms, nine indoor and six outdoor horse stalls, and a professional riding ring alongside the 7,500-square-foot stunning glass main house with four bedrooms designed by architect Niels Schoenfelder. At the center of this home is the show-stopping great room with 29' floor-to-ceiling glass flanked by fireplaces on each end, radiant heated limestone flooring, and glass doors to an expansive stone terrace. The chef's kitchen provides a walnut island with an AGA stove, double-sided fireplace, and accesses a spacious butler's pantry and the full outdoor kitchen off the terrace. Below the terrace are three ensuite bedrooms, a gym, wine room, mudroom, laundry room, and an attached heated two-car garage. The upper level houses an entire primary suite comprised of a sitting area, a double-sided fireplace that leads to the private bathroom, dressing room, and sauna. From the primary suite, one overlooks the 60' heated gunite pool and the rivers. The sound of rushing waterfalls provides tranquility from the extensive waterfront where the Roeliff Jansen Kill meets Shekomeko Creek, making it ideal for world-class trout fishing. Built on the site of the first settlers of Gallatin, dating before 1748, the property perfectly incorporates old and new. The land is diverse with open fields, trails, woodlands, two rivers, and a long bridge spanning the water. Less than two hours from Manhattan makes this the perfect country retreat. Co-exclusive with CORE Group Marketing.

Alwynds, a circa 1911 ivy covered stone and stucco Victorian home located in the Hudson Valley village of Pine Plains, built by Irving Huested Pulver (a local cattle dealer) The original charm of the home has been well preserved and maintained by the current owners over the last 46 years. Many of the original features and detailing such as, -Oak and Red Pine floors, Chestnut trim and paneled pocket doors, pantry and 1/2 bath just off the kitchen with custom cabinets. There is a stone fireplace in the dining room with a gas log insert (which will heat the downstairs during the winter months). There is a large walk-up attic just waiting for you to finish into a third floor living space. The property is amazingly private with 1.2 acres and close to all the local happenings. There's a large 2 story barn with a workshop, and storage and it has water and electricity. Behind the barn there is a fenced garden and woodshed. You'll enjoy fresh fruit from your very own orchard. Recent improvements include: 200-amp electrical service w/circuit breakers - hook up for generator - septic, roof and outside paint recently done - landscaping - painted stone basement with concrete floor - water softener - underground utilities to both the house and garage - Viking and Sub-Zero appliances in the kitchen, Kohler fixtures in the bathrooms. Walking distance to town with shopping, restaurants, pharmacy, bank, post office, and market. Hike Stissing Mountain or take a dip in Stissing Lake. 60 miles from Albany, 100 miles from NYC and only 7 miles off the Taconic Parkway. Price reduced, owners purchased a home.

Located at the end of a private road, this four bedroom home is comfortable and sure to please. The first level features a stylish eat-in-kitchen, light-filled dining room, cozy living room, family room, and a powder room. A primary suite with a stunning new bathroom, three additional bedrooms, and another full bathroom off the hallway complete the second floor. Many improvements throughout, including attractive oak flooring on the second floor. A spacious walk-out basement provides an opportunity for finishing more living space with a sliding glass door to access to the backyard. A new walkway and custom stonework enhance the front yard. For outside dining, there is a rear deck overlooking the 5+ private acres. Only a short drive to the town of Pine Plains makes this a convenient location with easy access to all local amenities. A great opportunity to make this your own home. Enjoy the sounds of nature in this country retreat!

Quintessential Hudson Valley Farmhouse. Nestled at the end of a country road in Gallatin overlooking your own stocked fishing pond, is this storybook setting with 265.17 acres of privacy. The home was newly constructed in 2011 from the original c.1787 homestead keeping some of the original details in a few rooms. A modern great room with soaring 14' beamed ceilings and a stone fireplace is the focal point of the house. A screened porch off the kitchen expands the space for summer evenings to dine. There is a primary suite on the first floor plus an additional bedroom, full bath and foyer. Upstairs, are two bedrooms and a full bath with one of the bedrooms having the original pine floors, wood paneling and beams. A detached oversized 2+ car garage/barn has many possibilities. Hardie Board siding, efficient utilities, A/C, and a whole house generator add to the appeal of this property. Delight in the peace and serenity this property offers with trails throughout the woodlands. Just 15 minutes to Pine Plains, 25 minutes to Rhinebeck, 2.5 hours to NYC and easy access to the Taconic State Parkway. Subdividable.

The approach to this spectacular contemporary barn-style home takes you up a long, winding private driveway past open fields & woods that are part of this special 22+ acre property. At the top of the hill, sits this incredibly private, recently completed, custom, stick built, 3-bedroom, 3.5-bath, contemporary home boasting approximately 4,000 sf of total square footage. This stunning home is designed to take advantage of its exquisite surroundings and to be one with nature with lots of windows, an open floor plan, and soaring high ceilings. Features include a standing seam roof, a lovely in-ground gunite pool, 9' engineered European oak flooring, a fabulous loft office/den, custom cabinetry and vanities, bedrooms with baths en suite, beautiful tiling, a contemporary propane fireplace, high-end appliances and a full basement, the perfect place for a gym/media room/family room/ playroom. Through the trees that surround the home, you can see glimpses of the mountains and pastoral farmland, and with some clearing, the views would be truly unparalleled. Conveniently located in New York's scenic Hudson Valley, just 6 minutes to Millerton & Pine Plains, 20 minutes to Rhinebeck, Red Hook & Millbrook and under 2 hours to NYC. Additional options at additional cost include bluestone patio, decking, garage and much more. Agricultural exemption ensures ongoing tax advantages!! A truly stunning and unique, must-see private property (not in a development).