Pine Plains, NY Homes for Sale

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  /50

  $3,495,000

  • 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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  /4

  $145,000

  • Land
  • 5.02 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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  /28

  $439,000

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  3807 Route 199, Pine Plains, NY 12567

  Situated between the charming villages of Pine Plains and Millerton, in the quaint hamlet of Pulver's Corners, this single-level residence radiates country elegance and a welcoming atmosphere. The backyard showcases a stone patio surrounded by lush perennial and vegetable gardens, offering a serene view of a picturesque pasture. Morning sunlight gracefully illuminates the rolling hills and

  

  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
  • 228.91 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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  /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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  /47

  $2,290,000

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

  729 Cold Spring Rd Unit 731, Stanfordville, NY 12581

  A Storied 1798 Farmhouse Between Millbrook & Rhinebeck Set 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 rare

  DOMINIQUE SHUMINOV William Pitt Sothebys Int Rlty

  729 Cold Spring Rd Unit 731, Stanfordville, NY 12581
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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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  /47

  $490,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  30 Myrtle Ave, Pine Plains, NY 12567

  Welcome to the Historic Town of Pine Plains! This completely renovated three bedroom home on a quiet country road will delight and intrigue you. The home dates back to the early 1900's and some of the original characteristics have been left in tact. This is most assuredly Old World Charm meets Modern Convenience. One bedroom on the first floor attached to the Sunroom, will work for a great Flex

  Ellen Mallet

  30 Myrtle Ave, Pine Plains, NY 12567
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  /37

  $575,000

  • 3 Beds
  • 1.5 Baths
  • 1,725 Sq Ft

  100 Knob Hill Rd, Stanfordville, NY 12581

  This beautiful and unique 10+ acre subdividable private property is a must see! The acreage currently includes a 3-bedroom, 2-bath ranch-style home as well as a separate 1200 SQFT workshop and the property offers so much more in endless opportunity – as a peaceful nature retreat, family compound, entrepreneurial venture- bring your vision when you visit! It’s located minutes off TSP on a quiet

  Kimberly Wickes R. Ferris Real Estate, LLC

  100 Knob Hill Rd, Stanfordville, NY 12581
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  /14

  $539,000

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

  284 Hall Hill Rd, Ancram, NY 12502

  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

  284 Hall Hill Rd, Ancram, NY 12502
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  /38

  $489,000

  • 4 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  82 Lake Rd, Pine Plains, NY 12567

  A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite

  MICHELLE FRANCESE Corcoran Country Living

  82 Lake Rd, Pine Plains, NY 12567
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  /20

  $1,250,000

  • 4 Beds
  • 2.5 Baths
  • 3,360 Sq Ft

  216 North Rd, Red Hook, NY 12571

  ?? 216 North Rd, Red Hook, NY 12571 Offered on 119 Acres – A Rare Hudson Valley Retreat Experience the best of country living on this stunning 119-acre estate bordering a state park, offering endless opportunities for outdoor recreation and peaceful privacy. This completely renovated 4-bedroom, 2-bath home combines modern comfort with the beauty of nature. Every detail has been updated — move-in

  Bill Flood Houlihan Lawrence Inc.

  216 North Rd, Red Hook, NY 12571
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  /21

  $265,000

  • 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? Looking for a good-sized plot of land? 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 or tear-down and rebuild. Currently, the main manufactured home has

  Jorge Lugo Real Broker NY LLC

  22-28 Ryan Rd, Pine Plains, NY 12567
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  /14

  $539,000

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

  284 Hall Hill Rd Stop 18, Ancram, NY 12502

  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

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

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  84 North Rd, Red Hook, NY 12571

  Early 1800s Colonial loved and enjoyed by same family for over 60 years. Looking for a visionary person to restore to former glory. Many original details still intact include hand hewn beams, wide board floors, cobble fireplace in Living room etc. 3 plus Bedrooms, 1 Full Bath with possible 2nd on upper level. Large country Kitchen, Formal Dining Room with Woodstove Hook Up and access to massive

  Catherine Mondello Mondello Upstate Properties

  84 North Rd, Red Hook, NY 12571
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  /41

  $10,850,000

  • 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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  /7

  $290,000

  • Land
  • 68.33 Acres
  • $4,244 per Acre

  000 New York 82, Pine Plains, NY 12567

  This beautiful, gently sloping parcel offers the perfect canvas to create your country escape or full-time residence on 68+ private acres. Soil tests have been done on a potential lower building site. A level area at a higher elevation could offer even more privacy and ridgeline views. Roughed-in driveway is in place, so you're well on your way to building a home that's tailored exactly to your

  Jeffries Blackerby Houlihan Lawrence Inc.

  000 New York 82, Pine Plains, NY 12567
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  /7

  $150,000

  • Land
  • 0.93 Acre
  • $161,290 per Acre

  58 Britton St, Pine Plains, NY 12567

  Two lots sold together totaling just under 1 acre. 1000 gallon concrete septic tank and leach fields already in place. Drilled well complete. Under ground 200 amp electric service installed. Current mobile home will be removed. Flat lot with all utilities in a well established residential area just waiting for a new home.

  Richard Brenner Rich Brenner Realty, LLC

  58 Britton St, Pine Plains, NY 12567
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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. Newly renovated home on North. Adjoining 8 acre vacant lot to the South available for 199,000. Owner financing possible.

  David Birch Barns & Farms Realty, LLC

  620 Bean River Rd, Pine Plains, NY 12567
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  /15

  $1,995,000

  • Land
  • 150.48 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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  /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 office,

  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

  $840,000

  • 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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  /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
  • 28.7 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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  /15

  $519,000

  • 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. Or buy the1400 SF 2BR/2BA RANCH with new well on 7+ acres for 385,000. Included is additional approved 8 acre building lot with approved septic design. Additional adjoining 4 acre building lot available for 139,000. Easy to show unoccupied.

  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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  /16

  $379,000

  • 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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  /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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  /12

  $499,000

  • 4 Beds
  • 1.5 Baths
  • 3,072 Sq Ft

  7786 S Main St, Pine Plains, NY 12567

  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.

  7786 S Main St, Pine Plains, NY 12567
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  /13

  $995,000

  • Land
  • 28.4 Acres
  • $35,035 per Acre

  390 Carpenter Hill Rd, Pine Plains, NY 12567

  With magnificent Catskill Mountain views, this 28 acre estate property is the perfect site to build the home of your dreams. The land features exceptional privacy among gentle rolling fields and stunning sunsets over the valley and the Catskills. There is already a gravel driveway in place plus plans for building, landscaping and septic. Much of the surrounding land is forever protected through

  Dan Kessler Compass Greater NY, LLC

  390 Carpenter Hill Rd, Pine Plains, NY 12567
• 

  

  /7

  $199,000

  • Land
  • 8.59 Acres
  • $23,166 per Acre

  622 Bean River Rd, Millerton, NY 12546

  Great opportunity for 1 or 2 residence (property is in Hamlet Zone and subdividable).Very private with small pond, site back from road on Bean River Road, quiet town road, .8 miles North of Route 199 near border with Columbia County. Approved Septic design and existing shared driveway. (May need improvement). Adjoins 2BR2BA Ranch for sale on 7+ acres for $399,000. Owner financing possible with

  David Birch Barns & Farms Realty, LLC

  622 Bean River Rd, Millerton, NY 12546
• 

  

  /21

  $375,000

  • Land
  • 5.02 Acres
  • $74,701 per Acre

  0 New York 82 Unit KEYM420064, Stanfordville, NY 12581

  Located in the center of Stanfordville, in upstate Dutchess County NY, this Hudson Valley opportunistic open development area is now available. The entire 5.02 acres are usable and zoned Rural Center with mixed use (commercial and residential) possibilities. The site is entered on an existing DOT approved road to a deeded 25' wide right of way to the property. The land is sub dividable and

  Steve Bruman Corcoran Country Living

  0 New York 82 Unit KEYM420064, Stanfordville, NY 12581
• 

  

  /27

  $300,000

  • 3,444 Sq Ft

  245 Hicks Hill Rd, Stanfordville, NY 12581

  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.

  245 Hicks Hill Rd, Stanfordville, NY 12581

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