Pine Plains, NY Houses for Sale

This c. 1880 three-story farmhouse seamlessly blends historic charm with modern luxury, meticulously cared for and thoughtfully curated to offer both timeless elegance and contemporary comfort.Step inside and be greeted by the inviting, light-filled living room. This spacious area exudes classic sophistication, centered around a warming wood-burning fireplace and boasting large windows that

Jill Rose Houlihan Lawrence Inc.

Nestled on 13 private acres of lush landscapes, meandering trails and impressive stone walls, you will find two very special vintage homes, outdoor sauna and shower plus small artist studio. Built in 1850 this two bedroom cottage combines historical character with contemporary amenities, featuring gleaming wood and wide board floors, beamed ceilings, stone fireplace, central air and a gourmet

Jeannine Simmons Corcoran Country Living

This architect designed and custom built passive solar home and guest house is sited privately on 17.90 acres with panoramic views of the of the eastern valley plains to Stissing Mountain and beyond. The tree lined driveway leads you to both houses that sit high on the land, facing south over looking the property fields & pond. Perfectly sited for the passive solar design and the solar panel

Kimberly Baker BHHS Hudson Valley Properties

Sunlight streams through the many windows and the vaulted ceilings with exposed beams create an airy, open atmosphere in this 1924 Ranch which has been beautifully renovated. Your mornings begin in the primary suite, where French doors open to a private deck overlooking a tranquil yard. Imagine sipping coffee while listening to birdsong and watching the changing seasons across your peaceful

Linda Lindsay Upstate Down

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

Welcome to Fallkill Farm, an incredible 37 acre oasis with expansive meadows, wooded buffers, mountain backdrop and Roeliff Jansen Kill frontage. Historic significance and modern amenities converge with the impeccably restored circa 1800 farmhouse featuring updated kitchen w/center island, designer cabinetry, Subzero refrigerator, Wolfe range and soapstone counters. Loaded with period features

Dan Axtmann BHHS Hudson Valley Properties

PINE PLAINS 2-3 LOT DEVELOPMENT, 15+ acres for Family Compound or upscale development between Pine Plains Village and Millerton on quiet road off Route 199. The Development includes a 1400 SF 2BR/2BA RANCH with new well, w/2 large decks, all wood floors, wood siding + detached 2 car garage on 7+ acres subdividable into 4 acres with house and 3 acre vacant lot. Included is additional approved 8

David Birch Barns and Farms Realty LLC

One level living. 2 Acres partially wooded. Lots of privacy. Put in a few updates and a little elbow grease and make this home your style.

MICHAEL MORRISON Corcoran Country Living

Want country living at its finest? LOOK no further! Nestled halfway between Rhinebeck and Millbrook is this Stanfordville gem! This gorgeous 3 bed 2 & half bath home sits on a majestic acre w/bucolic scenery surrounding you! You even have your own bubbling brook to mesmerize you! Simply sit out on the expansive decking and enjoy the natural beauty that greets you on so many levels that it

Justina Trainor BHHS Hudson Valley Properties

Meticulously maintained 2500+ sq ft 4-bedroom 2.5 bath center hall colonial sits on a beautiful and flat corner lot with stunning mountain views just minutes to the center of the town of Pine Plains. As you enter the home you immediately notice the care and attention to detail that the original owners have shown – Tasteful updates throughout include hardwood floors, chef’s kitchen with quartz

Ronald Green KW MidHudson

A darling country house. 4 Skiba sits on a quiet country lane with a sprawling sunlit lawn. The setting is as peaceful as can be, a little slice of heaven. Abutting very large parcels on either side, the land is just shy of an acre and feels expansive and private. Inside there is a wonderful amount of natural light. You’ll find a newly renovated kitchen and an open floor plan. There is a

Annabel Taylor Four Seasons Sothebys Intl

Welcome to 43 Stissing Mountain Drive — a peaceful and private retreat set on 2 beautifully wooded acres in the heart of the Hudson Valley. This great contemporary home offers 3 bedrooms and 2 bathrooms across 1,862 square feet of comfortable living space. With an open-concept layout, cathedral ceilings, and abundant natural light, the home blends style and function. A cozy fireplace anchors the

Richard Brenner Rich Brenner Realty, LLC

A true Hudson Valley treasure! Step into this enchanting 1934 Hudson Valley home, where vintage charm meets modern sophistication. Set on nearly 2 peaceful acres, this 2-bedroom, 2-bath retreat features a cozy open floor plan with an inviting fireplace/woodstove, multiple skylights, exposed beams, incredible architectural lines, and beautiful Doug fir wood floors. Offering a perfect blend of

Margaret Niekrewicz Margaret Mondello Real Estate

Whether for starting out retirement or weekend use, 48 Woodside Street is an efficient, move-in-ready home. Pine Plains offers a number of attractions from fine dining at the Stissing House, or a relaxing kayak paddle on Thompson Pond. Nearby hiking trails offer options such as the Stissing Fire Tower, a challenging local favorite, and the Thompson Preserve an easy woodland stroll around a

Brad Rebillard DUTCHESS COUNTRY REALTY INC. M

Spring has sprung and it is such a beautiful time of the year, here in Ancram, New York. The birds are starting to nest and are singing away!This 3 BR, 2 BA, 1768 sf log cabin is sited on 5 acres, and is surrounded by woods and meadows. A full basement below with its own fireplace (never used by these owners).There is a separate 3-acre parcel across the private road that is buildable. This will

Lindsay Lebrecht Copake Lake Realty Corp.

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 Family Compound with adjoining 8 acre and 4 acre boha parcels for 699,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show unoccupied.

David Birch Barns & Farms Realty, LLC

Nestled on top of Carpenter Hill, with unparalleled views of Stissing Mountain, the Catskills and the surrounding farmland, sits this country estate on 24.78 acres. The traditional, cedar shake 6,310 square foot home exudes elegance exhibited through the well proportioned rooms with 9’4” ceiling height, exceptional craftmanship and attention to detail found throughout the home. A dramatic double

PAULA REDMOND Corcoran Country Living

Nestled on 56 private acres of lush landscapes, meandering trails and impressive stone walls, you will find two very special vintage homes, sizeable barn, outdoor sauna and shower plus small artist studio. Built in 1850 this two bedroom cottage combines historical character with contemporary amenities, featuring gleaming wood and wide board floors, beamed ceilings, stone fireplace, central air

Jeannine Simmons Corcoran Country Living

Located in the picturesque Antlers Club Lake Community, this 2-bedroom, 2-bath Cape Cod offers a peaceful retreat with beach access and your own dock for kayaking, fishing, or relaxing by the water. The home features a bright and inviting layout, with spacious living areas, a well-equipped kitchen, and a full bath on the main level. Upstairs, a large bedroom and another full bath provide a cozy

Michael Cahill HomeSmart Homes & Estates

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 Family Compound with adjoining 8 acre and 4 acre boha parcels for 625,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show unoccupied.

David Birch Barns and Farms Realty LLC

Major Update! Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING 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

Diana Bisselle William Pitt Sothebys Int Rlty

Ingadi, the Zulu word for garden, is a true legacy compound all set within 127 acres of pristine land with a total of 11 bedrooms across four distinct residential structures. A magical journey of the senses where the Roeliff Jansen Kill and the Shekomeko Creek merge, ensuring sustainability while creating one of the most spiritually powerful and visually stunning experiences in the Hudson Valley.

Byron Anderson Compass Greater NY, LLC

Set among the beautiful rolling hills on 203 acres is this private estate that takes you back in time. The farm was built in 2008 around a c.1754 Dutch barn that was dismantled from upstate NY and transformed into an incredible great room with 34' soaring ceilings, a brick fireplace and two huge French doors to take in the view. Designed by Cynthia Filkoff with 6,340 square feet, the main house

Paula Redmond Corcoran Country Living - Mill

A long driveway leads to this imposing Greek Revival style house set high on a hill on 200 + acres of prime land overlooking Hudson Valley's farm country. Open fields and woodland with1600' of frontage on the Roeliff Jansen Kill. The house has 9000 sq ft with 12' ceilings throughout, large areas for entertaining, surrounding balconies for summer living and a 5000 bottle wine cave. The kitchen

HEATHER CRONER William Pitt Sotheby's Interna

You wanted charm? You got it! This vintage 1903 village home in Pine Plains, NY formerly served as both the town pharmacy and library, and many of the bookshelves and all the quaint apothecary drawers remain intact. The large 3000sq foot home on a nicely landscaped yard of nearly a half an acre is filled with period details: wooden moldings, original door knobs and intricate iron hardware, a

David Norman Hall Houlihan Lawrence Inc.

A quaint antique home is for sale in Gallatinville, NY. This rare 1820 home on .68 acres in a quiet hamlet 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 / office, then into a large dining room. The country kitchen and comfortable living

David Norman Hall Houlihan Lawrence Inc.