Pine Plains NY Real Estate & Homes for Sale

This very private home was designed and built by two architects who have enjoyed it for 20 yrs. The building elements, house, screen porch, pool enclosure, studio and garage are grouped around a venerable old white pine creating an exterior reminiscent of the traditional farm yard. Entering the home through a small porch and vestibule, the main space explodes into an 18ft. high single room for the living-dining room and kitchen. The shapes of the built-in fireplace, TV unit and dining table and buffet all reinforce the shape of the overall space. Natural light fills the rooms through a wall of French Doors facing the south with views of an open meadow. The balcony primary suite is light and airy with three large windows. The house was built on sloping land so the lower level bedrooms are above grade and flooded with light. There is a studio/guest quarters and a 20 x 40 heated gunite pool. Convenient to TSP and area attractions

Secluded 2BR/2BA RANCH w/2 large decks, all wood floors, ornamented wood siding painted + detached 2 car garage on 7 acres. Parcel is subdividable in Hamlet zone. New well installed.

Welcome to this 1867 square foot ranch, with 2 bedrooms, 2 bathrooms, an open kitchen and dining area, perfect for entertaining, cozy living room with propane fireplace and a large home office. The front entry boasts a welcoming foyer with a coat closet. Off the kitchen is a side entry mud room and laundry room. The master bedroom contains a walk in closet and a private bathroom with a jacuzzi tub. The full unfinished basement with poured concrete foundation holds the potential for additional living or recreational space. Outside you'll find a level lot measuring just shy or 1 acre and there is an older two car garage and shed. Don't miss this opportunity.

Dating back to 1787, this sprawling 4 bed, 3 bath farmhouse holds a rich history, passing through just three families. Remodeled and expanded in the 1900s, it underwent a comprehensive renovation in 2016, seamlessly blending historical charm with modern amenities.The house features extensive updates, including new plumbing, electric, windows, insulation, and drywall. It also offers wood flooring, radiant heat, original hand-hewn beams, updated fireplaces, and outdoor amenities such as a bluestone patio, custom fireplace, and pizza oven. Restoration efforts extend to the front porch, cast-iron radiators, original stonework, and chimney.This presents a unique opportunity to own a historical property in Pine Plains, mere seconds from the popular Hammertown Barn and the Stissing House Restaurant. Situated less than 30 minutes from Rhinebeck, Red Hook, and Millbrook, with easy access to the Wassaic Train Station, 10 minutes to Millerton, and just over 30 minutes to Hudson.

Come see this 3 bedroom, 2.5 bathroom colonial in Pine Plains. Situated on a half acre, level lot, this home is a short drive to the center of town for shopping or dining. Enjoy sitting peacefully on the front covered porch or entertain on the large deck. Numerous hiking and biking trails are nearby. Centrally located to Rhinebeck, Red Hook, Millbrook, Millerton and Hudson. Amtrak and MTA are 20 minutes away.

This very private home was designed & built by two architects who have enjoyed it for 20 yrs. The building elements, house, screen porch,pool enclosure, studio & garage are grouped around a venerable old white pine creating an exterior reminiscent of the traditional farm yard. Entering the home through a small porch & vestibule, the main space explodes into an 18ft. high single room for the living-dining room & kitchen. The shapes of the built-in fireplace, TV unit & dining table and buffet all reinforce the shape of the overall space. Natural light fills the rooms through a wall of French Doors facing the south with views of an open meadow. The balcony primary suite is light & airy with 3 large windows. The house was built on sloping land so the lower level bedrooms are above grade & flooded with light. There is a studio/guest quarters and a 20 x 40 gunite heated pool. Convenient to TSP and area attractions

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!

Welcome to your dream house lake retreat at 243 Lake Drive, directly across from Stissing Pond. This stunning new construction offers the perfect blend of modern design and serene lakeside living. The moment you step foot in this home you will fall in love with this open concept space. No detail has been overlooked, from the exceptionally large windows, fireplace, lighting, white oak floors, butlers pantry, hidden mud room, pocket doors, and much more. The kitchen is a chef's dream and fully equipped with top-of-the-line appliances, ample counter space and custom cabinetry. Whether you're hosting intimate gatherings or creating culinary masterpieces, this kitchen is sure to inspire you. Oversized windows throughout the home showcase breathtaking views of Stissing Mountain & Pond, creating a seamless connection between indoor comfort and outdoor beauty. The primary suite offers luxurious amenities, including spa-like ensuite bathroom, spacious walk in closet with laundry, and direct access to the outdoors. In addition to the primary suite, the home offers 3 other well-appointed bedrooms and bathrooms, living and work space. This is the most thoughtful and meticulous construction done to the highest standards. This property is packed with upgrades you must see to appreciate. Most notably the home comes with an additional neighboring BOH approved lot that can be used to build more structures to create your own compound or grounds for a pool and gardens. Pine Plains has been recognized as "The 12 Best Small Towns in New York" by Travel & Leisure and the local restaurant Stissing House is a James Beard Award Semifinalist. Whether you enjoy fishing, kayaking, hiking, or simply basking in the natural beauty of your surroundings, this lake paradise offers endless opportunities. Nestled between the towns and villages of Rhinebeck and Millbrook, just 10 minutes from the Taconic Parkway, and 2 hours to Manhattan, this home offers easy access to desirable local shopping, dining, and events.

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.

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.

Enjoy one level living in this cute ranch on a nice corner, quiet lot. Beautiful landscape. Fantastic opportunity to live in the picturesque village of Pine Plains. Walk to Stissing Lake and the Thompson Nature Preserve. Near all the amenities. Excellent starter or retirement home, freshly painted throughout. Nice level yard for a garden, family, pets and entertaining! Walk to library, community center, shops, restaurants, post office, and recreational areas and trails. An outdoor enthusiast's heaven! Come enjoy the lovely landscape, mountains, lakes and neighbors of Pine Plains! You will be impressed.,AboveGrade:1008,Cooling:Ceiling Fan,EQUIPMENT:Carbon Monoxide Detector,Smoke Detectors,ExteriorFeatures:Landscaped,FOUNDATION:Concrete,Slab,InteriorFeatures:Gas Dryer Connection,Washer Connection,Level 1 Desc:LIVING ROOM, KITCHEN, HALL, BATHROOM 1/2 AND FULL, BEEDROOMS,Other School:COLD SPRING,ROOF:Asphalt Shingles

Fly into this private, hilltop country estate with its own airstrip. This five bedroom, five and one half bath home has stunning bucolic views to Stissing Mountain and provides a layout that has an airy and elegant ambiance. The cathedral living room is centered around a soaring stone fireplace and leads to a cozy library and the formal dining room. Top of the line appliances, marble countertops, and a large butcher block clad island create the perfect chef's space. French doors from the eat-in kitchen and family room lead to a terrace with fireplace and Argentinian grill for al fresco dining. Upstairs, is the primary suite with balcony overlooking Stissing Mountain. An additional four bedrooms and three full baths are also on the second floor. The lower level offers laundry, an office and a full bath. Adding to the allure of this property is a 20' x 45' heated, gunite pool with a guest/pool house and a Har-tru tennis court. The guest/pool house features an additional loft bedroom, bath, kitchen and a gym with sauna. A fully stocked pond, garden and beautiful grounds on the 28.5 acres makes this the ideal place to unwind and enjoy the solitude of this property. Located just minutes to the quaint town of Pine Plains.

Fly into this private, hilltop country estate with its own airstrip. This five bedroom, five and one half bath home has stunning bucolic views to Stissing Mountain and provides a layout that has an airy and elegant ambiance. The cathedral living room is centered around a soaring stone fireplace and leads to a cozy library and the formal dining room. Top of the line appliances, marble countertops, and a large butcher block clad island create the perfect chef's space. French doors from the eat-in kitchen and family room lead to a terrace with fireplace and Argentinian grill for al fresco dining. Upstairs, is the primary suite with balcony overlooking Stissing Mountain. An additional four bedrooms and three full baths are also on the second floor. The lower level offers laundry, an office and a full bath. Adding to the allure of this property is a 20' x 45' heated, gunite pool with a guest/pool house and a Har-tru tennis court. The guest/pool house features an additional loft bedroom, bath, kitchen and a gym with sauna. A fully stocked pond, garden and beautiful grounds on the 29.96 acres makes this the ideal place to unwind and enjoy the solitude of this property. Located just minutes to the quaint town of Pine Plains.

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).

Welcome to Gallatin Homestead, an amazing country property comprised of 57.44 Acres, 2 Homes and multiple outbuildings. The property is made up of 47+/- acres of woodland, a 6+/- acre hay field and about 4 acres of area surrounding the homes and outbuildings. A natural stream flows through the property and is the delineation between the woodland and developed area. Home #1 is a Sidehall Colonial with addition. The home features 4 bedrooms, 3 baths and includes details such as solid oak doors, maple hardwood floors and wood stove insert in the living room fireplace. This home has a 38'x31' detached 3 car garage/workshop with large second floor.Home #2 is an Eyebrow Colonial with large front porch. This home features 5 bedrooms, 2 baths and includes details such as oak and maple hardwood flooring and wood burning stove in the living room. This home has a detached 24'x24' 2 car garage with second floor storage and firewood lean-to off the rear.The property also includes a massive 5 Bay 60'x120'x16' barn with 14' doors constructed in 2013. Within the barn, there is a 16'x18' office, 20'x34' machine shop and 18'x28' storage area all with loft space overhead. Radiant heating throughout with energy efficient spray foam insulation.A 18'x18' building with a 60kVA Onan Generator supplies energy to all structures on the property in the event of a power outage.On the edge of the 6+/- acre field is a partially enclosed pole barn, currently rented by the neighbor for storage.This property would make an incredible estate or compound with some updating and TLC. It is well suited for the outdoor enthusiast between the expansive workshop space and beautiful woodland with stream, natural rock outcroppings and nature trails. 18 miles to Hudson, 14 miles to Red hook and only 5.5 miles from the Taconic State Parkway.

Welcome to Gallatin Homestead, an amazing country property comprised of 57.44 Acres, 2 Homes and multiple outbuildings. The property is made up of 47+/- acres of woodland, a 6+/- acre hay field and about 4 acres of area surrounding the homes and outbuildings. A natural stream flows through the property and is the delineation between the woodland and developed area. Home #1 is a Sidehall Colonial with addition. The home features 4 bedrooms, 3 baths and includes details such as solid oak doors, maple hardwood floors and wood stove insert in the living room fireplace. This home has a 38'x31' detached 3 car garage/workshop with large second floor.Home #2 is an Eyebrow Colonial with large front porch. This home features 5 bedrooms, 2 baths and includes details such as oak and maple hardwood flooring and wood burning stove in the living room. This home has a detached 24'x24' 2 car garage with second floor storage and firewood lean-to off the rear.The property also includes a massive 5 Bay 60'x120'x16' barn with 14' doors constructed in 2013. Within the barn, there is a 16'x18' office, 20'x34' machine shop and 18'x28' storage area all with loft space overhead. Radiant heating throughout with energy efficient spray foam insulation.A 18'x18' building with a 60kVA Onan Generator supplies energy to all structures on the property in the event of a power outage.On the edge of the 6+/- acre field is a partially enclosed pole barn, currently rented by the neighbor for storage.This property would make an incredible estate or compound with some updating and TLC. It is well suited for the outdoor enthusiast between the expansive workshop space and beautiful woodland with stream, natural rock outcroppings and nature trails. 18 miles to Hudson, 14 miles to Red hook and only 5.5 miles from the Taconic State Parkway.

Meticulously Maintained ELEVATED Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING Mountain Views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This is unquestionably the perfect entertainment perch which captures the expansive long views of the valley and hillsides. Fabulous open floor plan inside, with vaulted ceilings in living room with stone fireplace, large dining area, and light and bright gourmet eat-in kitchen with high-end appliances. Primary bedroom also has vaulted ceilings, stone fireplace, and large walk-in closet leading to primary bath. Den/study off of primary bedroom. Another great entertaining space is found downstairs including a large area perfect for games, exercise or media room with kitchenette. Also downstairs is a large second bedroom and updated bathroom. 3 car heated garage with massive storage space upstairs. 45KW generator. For the horse enthusiast, the property also includes a hay barn, paddock, 4 stall horse barn & tack room, equipment sheds and arena. Great riding trails abound. This exceptional property is move-in ready and utterly magical.

Silvernails Farm is a legacy compound in the heart of the Hudson Valley, home to the breathtaking confluence of the Roeliff Jansen Kill and the Shekomeko Creek, a large natural basin, set within 127 acres of pristine land, integral to both Mohican and Dutch history. The recently completed 7,500sf main residence features lime stucco walls and solid fieldstone masonry on the interior and exterior with a mix of hardwood and Jerusalem limestone flooring. With 4 en-suite bedrooms, the residence also includes a powder room, private study/TV room, large laundry/pantry, wine cellar, and a gym. The living room with 26' ceilings is bracketed by two fireplaces. While embracing traditional craftsmanship and materials, the house is equipped with every modern convenience including an infrared sauna, steam room, 3 fireplaces, motorized shades, insect screens and radiant heated floors. The huge terrace has a covered seating area with a fully equipped kitchen, radiant floor heating and overhead heaters. The open design kitchen features a large pantry and workspace, 3 thick limestone counters, solid 3 walnut island with AGA stove and bar cabinet, twin dishwashers and sinks, crisper drawers, fridge, freezer, and wine fridge. There is a dog wash, covered firewood storage and a climate controlled two-car garage. South of the house, with magical river views and a fieldstone patio, sits a 60ft heated pool with an auto-cover. A fully renovated cottage delivers two separate living spaces: an upstairs 3-bedroom cottage and a downstairs 2-bedroom apartment. Several barns dating from the 1700's to the early 1900's include an equestrian barn with 9 large box stalls, heated wash stalls, tack room, office and feed room with a 2 bedroom apartment above. A utilitarian barn features additional stalls and an outdoor riding ring with show quality footing. Seven years of extensive effort has restored this sacred piece of land that inspires walking barefoot through the forest, basking in the river bends, and taking wild weed walks through the abundant forests that comprise a large portion of the property. Multiple outdoor living room vignettes with wooden decks inspire glamping and play in the natural beauty of this truly divine land. For sports enthusiasts, multiple options for riding, hiking, biking, rafting, kayaking, and superb fly-fishing are in abundance. Located 5 minutes from Pine Plains, 24 minutes from Rhinebeck and Hudson, this property epitomizes the Hudson Valley dream.,ExteriorFeatures:Gazebo,Landscaped,Outside Lighting,AboveGrade:7500,FLOORING:Wide Board,Wood,InteriorFeatures:Beamed Ceilings,Gas Stove Connection,Walk-In Closets,Heating:Central Heat,Zoned,Other School:PRIVATE,ROOF:Wood Shingles,EQUIPMENT:Carbon Monoxide Detector,Smoke Detectors,OTHERROOMS:Accessory Apartment,FOUNDATION:Concrete,AMENITIES:Pool