Pine Plains, NY Homes for Sale with Acreage

Perched high on 5.32 private acres with breathtaking, distant panoramic views of the Taconic Range and Berkshire Mountains, this contemporary home has been completely transformed by a top-to-bottom renovation. Seamlessly blending chic modern upgrades with dramatic architectural bones, this turn-key residence offers utmost privacy on a scenic country lane, yet still provides incredible

Callan Bergmann Compass Greater NY, LLC

Looking for a property that offers an opportunity for a homestead lifestyle in the Hudson Valley? Situated in the Town of Pine Plains, this early colonial farmhouse is now offered for sale on 15+ acres. Appointed with wide-plank floors, the main level features sun-lit, well-proportioned rooms. On the second floor, there is a primary bedroom with a dressing room, 3 additional bedrooms, an office,

Susan Whalen George T Whalen Real Estate

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. Also available with 8 additional acres for 565000 or with 12 acres (3 building lots) for 689000.

David Birch Barns & Farms Realty, LLC

Cedar Ridge Farm is a premier 246-acre equestrian estate set in the heart of Dutchess County, offering exceptional land quality, extensive infrastructure, and the rare scale required for a top tier equestrian operation or private country estate. The farm encompasses approximately 110 acres of fenced paddocks supported by thoughtfully designed facilities that ensure efficiency, functionality, and

George Langa Houlihan Lawrence Inc.

Set on 7.34 acres in Pine Plains, this 3-bedroom, 2-bath manufactured home offers 1,620 square feet of living space with plenty of room to enjoy the outdoors. A long driveway provides added privacy from Route 199, while the wooded surroundings and stream create a peaceful country setting.The single-level layout includes a living room, kitchen, den/office, three bedrooms, two full baths,

Derek Greene Greene Realty Group

Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming

HOMER STALEY JR. Staley Real Estate, LLC

Discover the Charm of Country Living Escape to this authentic 3-bedroom, 2-bath log home tucked away on a peaceful private road in Ancram. Set on 5 acres, the property also includes a separate 3-acre buildable lot across the lane-perfect for maintaining privacy, creating a guest house or studio, or simply preserving your view and open space. Start your day with coffee on the front porch, or soak

Kelly Harrison Taconic Valley Real Estate

Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has a proven track record as a highly successful Airbnb. Whether you are looking for a lucrative investment, a dream summer getaway, or a year-round sanctuary, this home has it all. The entire front of the house features stunning, unobstructed lake views. Start your mornings on

KELLY ROMANO Keller Williams Realty

Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit - the ultimate "entertainment perch" for soaking in breathtaking, panoramic valley

Diana Bisselle William Pitt Sothebys Int Rlty

Privately set on 32 extraordinary acres in the heart of Shekomeko, this light-filled country retreat captures sweeping views of Stissing Mountain and the Catskills from nearly every vantage point. A long drive winds through the landscape to a thoughtfully sited three-bedroom, two and a half bath residence featuring vaulted ceilings, expansive windows, a wood stove, and exceptional southern,

Byron Anderson Compass Greater NY, LLC

We welcome this 1834 restored farm into our Luxury Collection of Hudson Valley properties. This magnificent property makes the perfect country compound. Completely updated, restored and improved to also include a new addition on the main house. This 200 acre farm has all the privacy and beauty of a true country retreat. With such amenities as a converted dairy barn to an indoor tennis court

George Langa Houlihan Lawrence Inc.

2-4 Lot Subdivision, includes secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone (possible subdivision into 2 lots) Plus adjoining 8 acre parcel. Adjoining 4 acre boha parcel can be added for $125,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show with

David Birch Barns and Farms Realty LLC

Secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone Easy subdivision into 4 and 3 acre lots. Also available as Compound with adjoining 8 acre parcel for $565.000 and additional 4 acre boha parcel for $689,000. Adjoining parcels can be purchased separately for . Great location between Pine Plains Village and Millerton on quiet

David Birch Barns and Farms Realty LLC

Discover the Charm of Country Living Escape to this authentic 3-bedroom, 2-bath log home tucked away on a peaceful private road in Ancram. Set on 5 acres, the property also includes a separate 3-acre buildable lot across the lane—perfect for maintaining privacy, creating a guest house or studio, or simply preserving your view and open space. Start your day with coffee on the front porch, or soak

Kelly Harrison Taconic Valley Real Estate

A 1949 original, 153 Near Road was fully reimagined in 2021. The house is sited on two acres off a county lane, yet is a short distance to Hudson, Red Hook, Pine Plains with easy access to the Taconic Parkway. The first floor features an open concept, the kitchen, dining and living spaces flow together without interruption, anchored by a kitchen island and warmed by a wood stove. Flooded with

Jonathan Berry Upstate Down

An intoxicating opportunity to own a 343 acre swath of spectacular farmland, proudly eligible for the National Register of Historic Places, that encompasses several impressive barn structures, plus a fully functioning distillery and tasting room. Dutch's Spirits, on Harvest Homestead Farm, is a distillery with a legacy! Built in 1932 toward the end of the Prohibition Era, it was Dutchess County's

Andrew Gates Houlihan Lawrence, Inc.

Light-filled 2006 home blends privacy with effortless convenience. An open-air front porch and a generous backyard frame inviting indoor/outdoor living. Inside, the living room centers on a charming stove, while the chef’s kitchen echoes the home’s airy feel with an island and open plan ideal for entertaining. The first-floor primary suite is a private retreat with a freestanding tub and tiled

Liza Reiss Elyse Harney Real Estate

Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

Ernie Acampora River Realty Services, Inc.

Charming Cape Cod Retreat on Nearly 6 Acres in Pine Plains.Tucked away on a quiet country road just outside the village of Pine Plains, this charming three-bedroom, two-bath Cape Cod offers the perfect blend of country tranquility, comfortable living, and endless possibilities on nearly six beautiful acres.Welcoming you home with its cheerful yellow exterior, the spacious main level

David Norman Hall Houlihan Lawrence Inc.

Set far back from one of the Hudson Valley’s most prestigious and scenic roads, this stunningly restored 1830s colonial farmhouse is a masterclass in combining historic charm with sophisticated living. Situated in the heart of the pastoral Shekomeko Valley on just under 10 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white

Oliver Brown Houlihan Lawrence Inc.

Discover the Charm of Country LivingEscape to this authentic 3-bedroom, 2-bath log home tucked away on a peaceful private road in Ancram. Set on 5 acres, the property also includes a separate 3-acre buildable lot across the lane—perfect for maintaining privacy, creating a guest house or studio, or simply preserving your view and open space. Start your day with coffee on the front porch, or

Kelly Harrison Taconic Valley Real Estate

Beautifully reimagined 1924 home blends character with modern comfort and thoughtful design. Completely renovated in 2020 the residence offers 2,304 finished square feet with 3 bedrooms and 3 full baths. Vaulted ceilings, exposed beams abundant windows and an open-concept floor plan create a sense of beauty and spaciousness. The main level features warm wood floors, radiant heat throughout, and

Linda Lindsay Upstate Down