Pine Plains, NY Homes for Sale

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  /18

  $599,000

  • 4 Beds
  • 4 Baths
  • 3,928 Sq Ft

  115-133 Mount Ross Rd, Pine Plains, NY 12567

  My client wants this property to continue to be shown. There is an accepted offer. Historic 1880s Farmhouse with Expansive AcreageAn impressive home of distinction, this spacious 1880s farmhouse, enhanced by 20th-century additions, featuring soaring ceilings and beautiful original woodwork. While the home requires extensive updates, its charm and potential are extraordinary. Set on 65 acres of

  

  Larry Havens

  Havens Real Estate

  (518) 671-8313

  115-133 Mount Ross Rd, 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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  /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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  /14

  $285,000

  • Land
  • 9 Acres
  • $32,872 per Acre

  3362 New York 199, Pine Plains, NY 12567

  Here is an opportunity for you to build your dream home.8.67 acres of land in Pine Plain in Dutchess County, New York is for sale. This exceptional property is situated behind a 70-foot road frontage on Route 199.Key Features:Location: Pine Plains in Dutchess County, New YorkLand Size: 8.67 acresAccess: 70 feet of road frontage on Route 199Amenities: Cleared

  Community Lands

  3362 New York 199, Pine Plains, NY 12567
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  /29

  $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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  /11

  $900,000

  • 5 Beds
  • 2.5 Baths
  • 2,413 Sq Ft

  2365 Route 83, Pine Plains, NY 12567

  Rare opportunity to own 160 breathtaking acres in the heart of Pine Plains, featuring rolling fields, wooded terrain, and scenic wetlands. Anchoring the property is an antique farmhouse awaiting restoration, set within a 7 plus acre residential area offering privacy and pastoral charm. Most of the property is protected under a conservation easement, preserving the natural landscape while allowing

  Richard Brenner Rich Brenner Realty, LLC

  2365 Route 83, Pine Plains, NY 12567
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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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  /35

  $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 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

  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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  /43

  $1,225,000

  • 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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  /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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  /47

  $595,000

  • 4 Beds
  • 2 Baths
  • 2,605 Sq Ft

  5 Myrtle Ave, Pine Plains, NY 12567

  Beautiful Two Story, 4BR/2BA corner lot home with mountain views & quick walk to post office, shops, Stissing Lake & Stissing Mountain hiking trails. Experience the wonderful life of beautiful Pine Plains living! Wonderful large front, side & back yard on quiet sought after Myrtle Ave. Lovely front porch to sit & enjoy the scenery or head into the private back yard for a BBQ. Walk to school, post

  Thomas Zengen Thomas Zengen

  5 Myrtle Ave, Pine Plains, NY 12567
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  /25

  $589,000

  • 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

  $400,000

  • 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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  /50

  $549,900

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft

  1760 Route 199, Stanfordville, NY 12581

  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

  1760 Route 199, Stanfordville, NY 12581
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  /39

  $825,000

  • 3 Beds
  • 3 Baths
  • 2,304 Sq Ft

  82 Near Rd, Red Hook, NY 12571

  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

  82 Near Rd, Red Hook, NY 12571
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  /29

  $585,000

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

  143 Ryan Rd, Pine Plains, NY 12567

  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

  143 Ryan Rd, Pine Plains, NY 12567
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  /19

  $550,000

  • 2 Beds
  • 1.5 Baths
  • 1,774 Sq Ft

  4 Skiba Rd, Pine Plains, NY 12567

  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

  4 Skiba Rd, Pine Plains, NY 12567
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  /29

  $650,000

  • 3 Beds
  • 1.5 Baths
  • 1,862 Sq Ft

  43 Stissing Mountain Dr, Pine Plains, NY 12567

  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

  43 Stissing Mountain Dr, Pine Plains, NY 12567
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  /26

  $2,250,000

  • Land
  • 34 Acres
  • $66,430 per Acre

  7702-7714 S Main St, Pine Plains, NY 12567

  Prime 26.8-Acre Commercial Opportunity in Pine Plains, NYA rare investment opportunity awaits with this 26.8-acre commercial parcel—the last of its kind in the growing town of Pine Plains. Strategically located along South Main St (Route 82) with deeded right of way access from Route 83, this property is fully equipped for development and positioned to capitalize on the area’s increasing demand

  Richard Brenner Rich Brenner Realty, LLC

  7702-7714 S Main St, Pine Plains, NY 12567
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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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  /15

  $89,000

  • Land
  • 2.60 Acres
  • $34,231 per Acre

  0 Finkle Rd, Pine Plains, NY 12567

  Ready to build? Here's a great opportunity on 2.6 acres in Pine Plains NY. This cleared, mostly level lot has BOHA for a four bedroom home. Situated about halfway between Millerton and Pine Plains, this property offers country living while staying close to local amenities. This property is adjacent to 3977 Route 199

  Richard Brenner Rich Brenner Realty, LLC

  0 Finkle Rd, Pine Plains, NY 12567
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  /39

  $450,000

  • 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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  /24

  $449,000

  • Land
  • 25 Acres
  • $17,967 per Acre

  285 South Rd, Stanfordville, NY 12581

  Welcome to 24.99 Acres of Scenic Tranquility and Endless PossibilitiesDiscover the beauty and serenity of nearly 25 acres of gently rolling, wooded land, featuring captivating natural water elements—including two tranquil ponds and a meandering stream. A constructed driveway and underground electric service lead you deep into the heart of the property, where a charming barn stands

  Michael Tellerday Houlihan Lawrence Inc.

  285 South Rd, Stanfordville, NY 12581
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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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  /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.

  48 Woodside St, Pine Plains, NY 12567
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  /16

  $535,000

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

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

  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.

  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

  $389,000

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

  618 Bean River Rd, Pine Plains, NY 12567

  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

  618 Bean River Rd, Pine Plains, NY 12567
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  /25

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,097 Sq Ft

  1601 Route 199, Red Hook, NY 12571

  Charming Renovated Ranch with Scenic Views and Endless Potential, l with extra additional side lot!! Welcome to this beautifully renovated ranch-style home offering 1,200 square feet of comfortable, single-level living. Featuring 3 spacious bedrooms and 2 full baths, this thoughtfully updated home boasts a functional and versatile layout with multiple private entrances—perfect for

  Jason Schobert eXp Realty

  1601 Route 199, Red Hook, NY 12571
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  /43

  $4,950,000

  • 5 Beds
  • 4.5 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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  /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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  /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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  /22

  $189,900

  • 2 Beds
  • 1.5 Baths

  1691 Jackson Corners Rd, Red Hook, NY 12571

  Unique Opportunity Knocks! Visionaries Wanted! Older manufactured home is serving as living quarters for the current family. A separate foundation, building permit and a fully approved set of stamped plans are included with the property which overlooks a lovely, wooded hillside. Replace the current home with newer model or build your dream home or studio. Infrastructure in place includes well,

  Catherine Mondello MONDELLO UPSTATE PROPERTIES LLC

  1691 Jackson Corners Rd, Red Hook, NY 12571
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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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  /37

  $320,000

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft

  4 Antler Club Rd, Pine Plains, NY 12567

  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

  4 Antler Club Rd, 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 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

  618 Bean River Rd, Millerton, NY 12546
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  /34

  $1,575,000

  • 3 Beds
  • 3 Baths
  • 3,833 Sq Ft

  617 Bean River Rd, Millerton, NY 12546

  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

  617 Bean River Rd, Millerton, NY 12546
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  /36

  $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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