Pine Plains, NY Homes for Sale

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  /50

  $3,995,000

  • 4 Beds
  • 4 Baths
  • 4,103 Sq Ft

  476 Carpenter Hill Rd, Pine Plains, NY 12567

  Modern Minimalist Masterpiece on 19 Bucolic Acres in Dutchess County. Welcome to a rare offering in the heart of the Hudson Valley, where striking modern architecture meets timeless pastoral beauty. Completed in late 2024, this extraordinary estate sits on over 19 acres of flat, fenced farmland at the picturesque intersection of Bethel Cross and Carpenter Hill Road. Perfectly sited on a

  

  Rebecca Doh

  William Raveis Lifestyles Rlty

  (518) 594-8655

  476 Carpenter Hill Rd, Pine Plains, NY 12567
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  /28

  $475,000

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  3807 Route 199, Pine Plains, NY 12567

  Nestled between the villages of Pine Plains and Millerton, in the hamlet of Pulver's Corners, this single-level home exudes country charm and a cozy vibe. The backyard features a stone patio surrounded by perennial and vegetable gardens, with a picturesque view of a pasture. Morning sunlight beautifully illuminates the rolling hills and farmland beyond. Inside, the home boasts natural wood

  

  Brad Rebillard

  DUTCHESS COUNTRY REALTY INC. M

  (518) 941-8819

  3807 Route 199, Pine Plains, NY 12567
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  /24

  $3,600,000

  • Land
  • 229 Acres
  • $15,727 per Acre

  0 Skunks Misery Rd Unit KEY860535, Pine Plains, NY 12546

  Sensational vistas of the stunning and unspoiled countryside extending to the Taconic's to the East and from a hidden knoll with an elevation of 1,250' there is a magnificent private setting with incredible Catskill views. The main parcel of 157 acres is offered for the first time in generations and that parcel adjoins a 71.5-acre parcel, this was a family owned and operated farm. Both properties

  

  Larry Havens

  Havens Real Estate

  (518) 676-2868

  0 Skunks Misery Rd Unit KEY860535, Pine Plains, NY 12546
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  /26

  $379,000

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  48 Woodside St, Pine Plains, NY 12567

  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.

  (518) 662-5219

  48 Woodside St, Pine Plains, NY 12567
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  /4

  $145,000

  • Land
  • 5 Acres
  • $28,884 per Acre

  0 Mount Ross Rd, Pine Plains, NY 12567

  Every once in a while, an exceptional opportunity like this turns up. Located in rural Pine Plains this 5.02-acres is a pair of vacant building lots that offers privacy and serenity. These two contiguous parcels are completely wooded and accessed via a shared driveway. Your dream home is only limited by your imagination these parcels will invigorate that imagination. The Town center and the

  

  Larry Havens

  Havens Real Estate

  (518) 672-6676

  0 Mount Ross Rd, Pine Plains, NY 12567
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  /7

  $1,995,000

  • 3 Beds
  • 2.5 Baths
  • 2,267 Sq Ft

  820 Cold Spring Rd, Stanfordville, NY 12581

  (To be built) Perfectly sized upstate retreat, Zenith integrates seamlessly with its bucolic setting, minutes from Rhinebeck village. The low pitched angled roof planes intersect in the residence’s great room with clerestory windows to flood the living spaces with light.Zenith is sited on 7 private primarily wooded acres. The residence showcases interiors with natural textures and a

  DOUG MAXWELL Upstate Modernist

  820 Cold Spring Rd, Stanfordville, NY 12581
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  /37

  $1,225,000

  • 4 Beds
  • 2 Baths
  • 1,888 Sq Ft

  174 County Route 11, Pine Plains, NY 12567

  Expansive 55+ Acre Multi-Home Compound. A rare opportunity to own a one-of-a-kind compound set on 57.44 private, picturesque acres—ideal for multi-generational living or a unique investment. The main residence offers 1,888 square feet of rustic charm and comfort, featuring 4 bedrooms and 2 full baths. Enjoy cozy evenings in the living room with pegged oak floors, pine paneling, and a classic

  Paula Redmond Corcoran Country Living - Mill

  174 County Route 11, Pine Plains, NY 12567
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  /31

  $2,495,000

  • 6 Beds
  • 5 Baths
  • 3,352 Sq Ft

  729 Cold Spring Rd Unit 731, Stanfordville, NY 12581

  A Storied 1798 Farmhouse Between Millbrook & RhinebeckSet at the end of a long, graceful gravel drive and surrounded by large estates and protected land, The George is a timeless 1798 farmhouse quietly nestled on 7.2 serene acres in the heart of the Hudson Valley. Beautifully framed by towering old-growth trees, gently rolling lawns, and a freshwater pond, this historic property offers a

  DOMINIQUE SHUMINOV William Pitt Sothebys Int Rlty

  729 Cold Spring Rd Unit 731, Stanfordville, NY 12581
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  /33

  $2,495,000

  • 3 Beds
  • 3 Baths
  • 4,648 Sq Ft

  387 Skunks Misery Rd, Millerton, NY 12546

  Perched high above Millerton in the Hudson Valley, this exceptional 2020-built contemporary farmhouse estate commands 53± private acres with panoramic western views spanning the Catskills and Berkshire Mountain Range, including Mount Kaaterskill. Wide red oak hardwood floors unite the main level, where abundant natural light floods through expansive windows, creating an atmosphere of

  Elyse Morris Elyse Harney Real Estate

  387 Skunks Misery Rd, Millerton, NY 12546
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  /43

  $1,175,000

  • 5 Beds
  • 3 Baths
  • 2,482 Sq Ft

  303 Hicks Hill Rd, Stanfordville, NY 12581

  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

  303 Hicks Hill Rd, Stanfordville, NY 12581
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  /36

  $1,499,000

  • 5 Beds
  • 3.5 Baths
  • 4,176 Sq Ft

  1598 Jackson Corners Rd, Red Hook, NY 12571

  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

  1598 Jackson Corners Rd, Red Hook, NY 12571
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  /37

  $1,595,000

  • 4 Beds
  • 3 Baths
  • 3,980 Sq Ft

  235 Knob Hill Rd, Stanfordville, NY 12581

  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

  235 Knob Hill Rd, Stanfordville, NY 12581
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  /7

  $139,000

  • Land
  • 4.24 Acres
  • $32,783 per Acre

  620 Bean River Rd, Pine Plains, NY 12567

  Great opportunity for 1 residence (property is in Hamlet Zone and possibly subdividable). Approved Septic design and existing shared driveway. (May need improvement). Newly renovated home on North and vacant 8 acre lot for 225,000 on South. Owner financing possible.

  David Birch Barns & Farms Realty, LLC

  620 Bean River Rd, Pine Plains, NY 12567
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  /37

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,580 Sq Ft

  143 Ryan Rd, Pine Plains, NY 12567

  This 4 Bedroom, 2.5 Bath Classy Contemporary Colonial emulates "Pride of Ownership" and has so much to offer anyone looking for a turnkey home in a wonderful town. As you enter the airy Center Hall you will immediately fall in love with the gleaming Cherry Hardwood Floors that run abundantly through the whole home. Appreciate the Crown Molding that accentuates each room. Marvel at the lofty

  Catherine Mondello Mondello Upstate Properties

  143 Ryan Rd, Pine Plains, NY 12567
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  /17

  $345,000

  • 2 Beds
  • 3 Baths
  • 1,728 Sq Ft

  46 Myrtle Ave, Pine Plains, NY 12567

  Check out this charming two family home in the Town of Pine Plains. Live in one unit and keep the other unit rented OR rent out the entire building. One unit was recently updated. Separate utilities and each unit has its own driveway and storage shed. Covered porch, screened-in porch, large backyard. Convenient location, walk to shops & local attractions.

  Susan Whalen George T Whalen Real Estate

  46 Myrtle Ave, Pine Plains, NY 12567
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  /15

  $1,995,000

  • Land
  • 150 Acres
  • $13,258 per Acre

  1533-1539 Route 83, Pine Plains, NY 12567

  Discover a rare 150-acre estate in one of the Hudson Valley’s most coveted farmland corridors. This property offers a private building site accessed by a scenic driveway and showcases the best of Hudson Valley living where nature meets luxury. Enjoy panoramic views of protected farmland, Shekomeko Creek, and wooded mountains. Surrounded by conservation land, this estate ensures lasting privacy

  John Panzer Elyse Harney Real Estate

  1533-1539 Route 83, Pine Plains, NY 12567
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  /38

  $579,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,269 Sq Ft

  540 Hicks Hill Rd, Stanfordville, NY 12581

  Charming 3-bedroom, 2.5-bathroom Colonial nestled on 5.58 private acres. Enjoy quiet moments on your wrap-around rocking chair front porch and take in picturesque views of Stissing Mountain. This inviting home features a spacious living room, formal dining room and an eat-in kitchen that flows into a comfortable family room perfect for gatherings. Step out from the family room onto a patio ideal

  Rita Longo Howard Hanna Rand Realty

  540 Hicks Hill Rd, Stanfordville, NY 12581
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  /30

  $595,000

  • 4 Beds
  • 2.5 Baths
  • 3,180 Sq Ft

  30 N Main St, Pine Plains, NY 12567

  Grand 1880 Colonial Estate Sale - Historic Fixer-Upper with Original Features and Garden Oasis Near Town CenterThis rare 1880 Grand Colonial is a dream opportunity for restoration enthusiasts and anyone searching for a historic fixer-upper near the heart of town. Situated on a flat, tree-lined lot, this estate sale is being sold as is and is filled with authentic charm—from original

  Arleen Shepley Elyse Harney Real Estate

  30 N Main St, Pine Plains, NY 12567
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  /13

  $4,950,000

  • 3 Beds
  • 2 Baths
  • 5,000 Sq Ft

  3362 New York 199, Pine Plains, NY 12567

  To-Be-Built Luxury Estate with Infinity Pool & Panoramic Catskill Views – Pine Plains, NY. Elevated high above the valley floor with sweeping, unobstructed Catskill Mountain views, this to-be-built custom estate is a rare opportunity in the heart of the Hudson Valley. Set on an extraordinary piece of land—offering total privacy and dramatic natural beauty—this 5,000+ square foot

  Michael Lund Corcoran Country Living

  3362 New York 199, Pine Plains, NY 12567
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  /7

  $145,000

  • Land
  • 3.45 Acres
  • $42,029 per Acre

  66 Ryan Rd, Pine Plains, NY 12567

  Build your dream home in the heart of Pine Plains, surrounded by nature, history, and vibrant Hudson Valley living, on this exceptional 3.45 Acre elevated homesite, Board of Health approved for a 4-bedroom residence, with sweeping views of majestic Stissing Mountain. This remarkable parcel offers the perfect blend of tranquility, natural beauty, and convenience, presenting a rare opportunity to

  Vida Odescalchi Legacy Land & Homes LLC

  66 Ryan Rd, Pine Plains, NY 12567
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  /38

  $875,000

  • 4 Beds
  • 1.5 Baths
  • 2,709 Sq Ft

  7668 Route 82, Pine Plains, NY 12567

  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

  Susan Whalen George T Whalen Real Estate

  7668 Route 82, Pine Plains, NY 12567
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  /50

  $8,475,000

  • 6 Beds
  • 7.5 Baths
  • 12,418 Sq Ft

  367 Prospect Hill Rd, Ancramdale, NY 12503

  First time on the market! This magnificent 170-acre Modern Adirondack-styled estate near Millbrook, designed by architect Lloyd Taft, features a main house and three elegant guest cabins. Built by a third-generation builder of camps in upstate New York and the Thousand Islands, the cabin serves as the centerpiece of the compound. Meticulously maintained and tailor-made for year-round recreation,

  George Langa Houlihan Lawrence Inc.

  367 Prospect Hill Rd, Ancramdale, NY 12503
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  /30

  $925,000

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft

  1388 Route 83, Pine Plains, NY 12567

  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.

  1388 Route 83, Pine Plains, NY 12567
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  /36

  $995,000

  • 4 Beds
  • 3 Baths
  • 3,980 Sq Ft

  235 Knob Hill Rd, Stanfordville, NY 12581

  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 farmhouse combines historical character with contemporary amenities, featuring gleaming wood and wide board floors beamed ceiling, stone fireplace, central air and a gourmet

  Jeannine Simmons Corcoran Country Living

  235 Knob Hill Rd, Stanfordville, NY 12581
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  /43

  $899,000

  • 5 Beds
  • 3.5 Baths
  • 2,714 Sq Ft

  198 Sigler Rd, Pine Plains, NY 12567

  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

  198 Sigler Rd, Pine Plains, NY 12567
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  /25

  $535,000

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft

  618 Bean River Rd, Millerton, NY 12546

  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

  618 Bean River Rd, Millerton, NY 12546
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  /20

  $375,000

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  1814 Route 199, Stanfordville, NY 12581

  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

  1814 Route 199, Stanfordville, NY 12581
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  /19

  $995,000

  • Land
  • 29 Acres
  • $34,669 per Acre

  5-8 Lakeside Ln, Pine Plains, NY 12567

  Welcome to your own slice of paradise! This beautiful 29-acre waterfront property offers the perfect canvass for your dream home. Nestled in the shadow of Stissing Mountain, you'll enjoy country views and ample space to build your oasis. Boasting approximately 800 feet of waterfront on Twin Island Lake, enjoy fishing, kayaking or just observing natures glory. Privacy is paramount on this property

  Richard Brenner Rich Brenner Realty, LLC

  5-8 Lakeside Ln, Pine Plains, NY 12567
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  /39

  $399,000

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  107 Near Rd, Red Hook, NY 12571

  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

  107 Near Rd, Red Hook, NY 12571
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  /49

  $699,000

  • 7 Beds
  • 5 Baths

  80 County Route 7, Pine Plains, NY 12567

  This beautifully updated legal 2-family home seamlessly blends vintage charm with modern convenience, offering exceptional flexibility for multigenerational living, rental income, or guest accommodations. Located just 7 minutes from Pine Plains Village and set on a scenic lot with sweeping countryside views and a neighboring 200-acre farm, the property features meticulously maintained grounds,

  Margaret Niekrewicz Margaret Mondello Real Estate

  80 County Route 7, Pine Plains, NY 12567
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  /16

  $539,000

  • 3 Beds
  • 2 Baths
  • 1,768 Sq Ft

  284 Hall Hill Rd-Stop # 18, Ancram, NY 12502

  A ''Real Deal'' log home in Ancram, New York. This listing has been reconfigured to include a separate 3 acre building parcel, across the private dead-end road. Read below the importance of this added acreage. The home has 3 BR, 2 BA, and is 1768 sf. It is surrounded by woods and meadows. There is a brick fireplace, wood stove, open floor plan, and deck out back. Fiber-optic

  Lindsay Lebrecht Copake Lake Realty Corp.

  284 Hall Hill Rd-Stop # 18, Ancram, NY 12502
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  /22

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,037 Sq Ft

  22-28 Ryan Rd, Pine Plains, NY 12567

  Looking for a piece of property for a great low price? Looking for two homes for the price of one? Here is a great opportunity for you to acquire one manufactured home, and one mobile home, both on the same plot of land with 2.30 acres! Investors will consider this property for rental income. Those interested in home ownership will consider this property as well, given you can live in one of the

  Jorge Lugo Real Broker NY LLC

  22-28 Ryan Rd, Pine Plains, NY 12567
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  /15

  $535,000

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft

  618 Bean River Rd, Pine Plains, NY 12567

  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 & Farms Realty, LLC

  618 Bean River Rd, Pine Plains, NY 12567
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  /45

  $4,950,000

  • 5 Beds
  • 5.5 Baths
  • 6,310 Sq Ft

  310 Carpenter Hill Rd, Pine Plains, NY 12567

  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

  310 Carpenter Hill Rd, Pine Plains, NY 12567
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  /6

  $409,000

  • Land
  • 111 Acres
  • $3,685 per Acre

  0 Route 82 Unit 156245, Pine Plains, NY 12567

  Large parcel with 1700 foot of frontage on 3 road. Lots of possibilities for estate, recreation or subdivision. Convenient to Taconic Parkway and Hudson.

  David Birch Barns & Farms Realty, LLC

  0 Route 82 Unit 156245, Pine Plains, NY 12567
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  /16

  $389,000

  • 2 Beds
  • 1.5 Baths
  • 1,336 Sq Ft

  618 Bean River Rd, Millerton, NY 12546

  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 parecel for $535,000. Additional 4 acre boha parcel for $135,000. Adjoining parcels can be purchased separately. Great location between Pine Plains Village and Millerton on quiet

  David Birch Barns and Farms Realty LLC

  618 Bean River Rd, Millerton, NY 12546
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  /35

  $18,750,000

  • 11 Beds
  • 7.5 Baths
  • 7,500 Sq Ft

  461 Silvernails Rd, Pine Plains, NY 12567

  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

  461 Silvernails Rd, Pine Plains, NY 12567
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  /36

  $12,000,000

  • 5 Beds
  • 3.5 Baths
  • 6,340 Sq Ft

  118 Finkle Rd, Ancramdale, NY 12503

  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

  118 Finkle Rd, Ancramdale, NY 12503
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  /29

  $7,400,000

  • 9 Beds
  • 11 Baths
  • 9,000 Sq Ft

  255 Mill Hill Rd, Pine Plains, NY 12567

  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

  255 Mill Hill Rd, Pine Plains, NY 12567
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  /8

  $545,000

  • Land
  • 51 Acres
  • $10,754 per Acre

  0 Route 82, Ancramdale, NY 12503

  Come see this beautiful property of 50+ wooded acres with incredible Catskill views! Total privacy with a picture perfect building site at the top of the hill, build a dream home that will gaze westward toward the Catskill Mountains. It has a varied terrain with many possibilities for hiking and walking trails, vantage points offering a variety of views, and sitting just outside the hamlet of

  David Norman Hall Houlihan Lawrence Inc.

  0 Route 82, Ancramdale, NY 12503

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