Pine Plains, NY Homes

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  $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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  /50

  $2,610 per month

  Stissing Farms

  2 Beds

  51 Hillside Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and two car parking (one garage, one driveway)thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private

  51 Hillside Rd, Pine Plains, NY 12567
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  $732,000 Sold Oct 09, 2025

  546 Hicks Hill Rd, Stanfordville, NY 12581

  • 3 Beds
  • 2.5 Baths
  • 2,971 Sq Ft
  • Built 2003

  Last Sold Summary

  • $246/SF
  • 33 Days On Market

  Current Estimated Value $714,000

  Last Listing Agent Joseph Iannibelli Keller Williams NY Realty

  546 Hicks Hill Rd, Stanfordville, NY 12581
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  Est $1,718,038 Not Listed For Sale

  454 Bean River Rd, Pine Plains, NY 12567

  454 Bean River Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 9% Below List Price
  • 194 Days On Market

  Last Sold Price $1,895,000

  Last Listing Agent PAULA REDMOND Corcoran Country Living
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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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  $2,610 per month

  • 2 Beds
  • 2 Baths
  • 1,147 Sq Ft
  • Townhouse for Rent

  32 Town Centre Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  32 Town Centre Rd, Pine Plains, NY 12567
• 

  $415,000 Sold Oct 14, 2025

  1601 Route 199, Red Hook, NY 12571

  • 3 Beds
  • 2 Baths
  • 1,097 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $378/SF
  • 30 Days On Market

  Current Estimated Value $440,000

  Last Listing Agent Jason Schobert eXp Realty

  1601 Route 199, Red Hook, NY 12571
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  Est $2,023,327 Not Listed For Sale

  88 Friar Tuck Rd, Ancramdale, NY 12503

  • 6 Beds
  • 3.5 Baths
  • 3,804 Sq Ft
  • Built 1880

  88 Friar Tuck Rd, Ancramdale, NY 12503

  Last Sold Summary

  • 1% Above List Price
  • $526/SF
  • 202 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Ann Simmons Compass Greater NY, LLC d/b/a
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  $120,000

  • Land
  • 5.02 Acres
  • $23,904 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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  $2,790 per month

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Townhouse for Rent

  53 Hillside Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  53 Hillside Rd, Pine Plains, NY 12567
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  /13

  $924,500 Sold Aug 07, 2025

  Tbd Woods Dr, Ancramdale, NY 12503

  • Land
  • 105.45 Acres
  • $8,767 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 113 Days On Market

  Last Listing Agent Arlena Armstrong Anatole House LLC

  Tbd Woods Dr, Ancramdale, NY 12503
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  Est $556,582 Not Listed For Sale

  7795 S Main St, Pine Plains, NY 12567

  • Studio
  • 4,032 Sq Ft
  • Built 1979

  7795 S Main St, Pine Plains, NY 12567

  Last Sold Summary

  • 14% Below List Price
  • $121/SF

  Last Sold Price $489,000

  Last Listing Agent Jo-Ann Campagiorni
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  $4,495,000

  • 7 Beds
  • 4 Baths
  • 5,481 Sq Ft

  8032-8060 New York 82, Pine Plains, NY 12567

  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.

  8032-8060 New York 82, Pine Plains, NY 12567
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  /15

  $2,750 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Townhouse for Rent

  7 Hillside Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  7 Hillside Rd, Pine Plains, NY 12567
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  $4,970,000 Sold Mar 09, 2026

  310 Carpenter Hill Rd, Pine Plains, NY 12567

  • 5 Beds
  • 5.5 Baths
  • 6,310 Sq Ft
  • Built 1993

  Last Sold Summary

  • 11% Below List Price
  • $788/SF
  • 239 Days On Market

  Current Estimated Value $3,689,385

  Last Listing Agent PAULA REDMOND Corcoran Country Living

  310 Carpenter Hill Rd, Pine Plains, NY 12567
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  Not Listed For Sale

  7604 Route 82, Pine Plains, NY 12567

  • 5 Beds
  • 3.5 Baths
  • 3,712 Sq Ft
  • Built 1970

  7604 Route 82, Pine Plains, NY 12567

  Last Sold Summary

  • $131/SF
  • 346 Days On Market

  Last Sold Price $485,000

  Last Listing Agent MICHELLE FRANCESE Corcoran Country Living
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  $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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  $2,750 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Townhouse for Rent

  20 Town Centre Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  20 Town Centre Rd, Pine Plains, NY 12567
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  $390,000 Sold Aug 11, 2025

  285 South Rd, Stanfordville, NY 12581

  • Land
  • 24.99 Acres
  • $15,606 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 54 Days On Market

  Current Estimated Value $395,484

  Last Listing Agent Michael Tellerday Houlihan Lawrence Inc.

  285 South Rd, Stanfordville, NY 12581
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  Not Listed For Sale

  0 County Route 11, Pine Plains, NY 12567

  0 County Route 11, Pine Plains, NY 12567

  Last Sold Summary

  • 69 Days On Market

  Last Sold Price $28,000

  Last Listing Agent Melissa Vooris Past Member
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  /18

  $3,995,000

  • 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 residence is

  Michael Lund Corcoran Country Living

  3362 New York 199, Pine Plains, NY 12567
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  /17

  $2,950 per month

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • House for Rent

  119 Righters Corners Rd, Pine Plains, NY 12567

  Welcome to 119 Righters Corners Rd, a charming and well-maintained two-bedroom, one-bathroom home located in the scenic Town of Pine Plains, New York. This inviting residence features hardwood floors throughout, creating a warm and cohesive living space. The kitchen and bathroom have been tastefully renovated, offering modern finishes while maintaining the home’s comfortable, classic feel. The

  Richard Brenner Rich Brenner Realty, LLC

  119 Righters Corners Rd, Pine Plains, NY 12567
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  /12

  $55,000 Sold Oct 27, 2025

  0 County Route 8 Unit 20252154, Gallatin, NY 12567

  • Land
  • 1.1 Acres
  • $50,000 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 46 Days On Market

  Last Listing Agent Joel Craig Coldwell Banker Village Green

  0 County Route 8 Unit 20252154, Gallatin, NY 12567
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  Not Listed For Sale

  0 County Route 7 Unit 144952, Pine Plains, NY 12567

  0 County Route 7 Unit 144952, Pine Plains, NY 12567

  Last Sold Summary

  • 659 Days On Market

  Last Sold Price $809,000

  Last Listing Agent Ann Simmons Compass Greater NY, LLC d/b/a
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  $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

  $6,500 per month

  • 1 Bed
  • 1.5 Baths
  • 936 Sq Ft
  • House for Rent

  43 Lake Shore Dr, Pine Plains, NY 12567

  Welcome to The Lake Cottage – A Rare Seasonal Retreat on Twin Island LakeDiscover The Lake Cottage, a one-of-a-kind, fully furnished seasonal escape on the shores of Twin Island Lake. This private lakefront compound offers a tranquil and inspiring setting, making it the perfect getaway for artists, writers, creatives, or anyone in search of rest and renewal.Nestled behind lush, mature

  SHERI SCEROLER Four Seasons Sothebys Intl

  43 Lake Shore Dr, Pine Plains, NY 12567
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  $270,000 Sold Jan 08, 2026

  34 Myrtle Ave, Pine Plains, NY 12567

  • 5 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 1900

  Last Sold Summary

  • 7% Below List Price
  • $129/SF
  • 17 Days On Market

  Current Estimated Value $287,294

  Last Listing Agent Blake Michaud BHHS Hudson Valley Properties

  34 Myrtle Ave, Pine Plains, NY 12567
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  Est $642,584 Not Listed For Sale

  308 Hall Hill Rd, Ancram, NY 12502

  • 3 Beds
  • Built 1974

  308 Hall Hill Rd, Ancram, NY 12502

  Last Sold Summary

  • 543% Above List Price
  • $39/SF
  • 94 Days On Market

  Last Sold Price $100,000

  Last Listing Agent Chelsea Pollard-Seiler Mondello Upstate Properties
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  $4,395,000

  • 10 Beds
  • 6.5 Baths
  • 6,994 Sq Ft

  1515-1517 County Road 83, Pine Plains, NY 12567

  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 9.6 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white clapboard

  OLIVER BROWN Houlihan Lawrence Inc.

  1515-1517 County Road 83, Pine Plains, NY 12567
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  $810,000 Sold Apr 08, 2025

  2854 Church St, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 2,208 Sq Ft
  • Built 1911

  Last Sold Summary

  • 2% Below List Price
  • $367/SF
  • 61 Days On Market

  Current Estimated Value $820,579

  Last Listing Agent Diana Bisselle William Pitt Sothebys Int Rlty

  2854 Church St, Pine Plains, NY 12567
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  Est $327,190 Not Listed For Sale

  44 Conklin Hill Rd, Stanfordville, NY 12581

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft
  • Built 1975

  44 Conklin Hill Rd, Stanfordville, NY 12581

  Last Sold Summary

  • 26% Above List Price
  • $351/SF
  • 170 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Jill Rose Houlihan Lawrence Inc.
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  /22

  $315,000

  • 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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  $2,153,550 Sold Mar 04, 2026

  820 Cold Spring Rd, Stanfordville, NY 12581

  • 3 Beds
  • 2.5 Baths
  • 2,267 Sq Ft
  • Built 2025

  Last Sold Summary

  • 8% Above List Price
  • $950/SF
  • 166 Days On Market

  Last Listing Agent DOUG MAXWELL Upstate Modernist

  820 Cold Spring Rd, Stanfordville, NY 12581
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  Est $1,071,590 Not Listed For Sale

  140 Mountain Rd, Stanfordville, NY 12581

  • 3 Beds
  • 3 Baths
  • 2,568 Sq Ft
  • Built 1984

  140 Mountain Rd, Stanfordville, NY 12581

  Last Sold Summary

  • 32% Below List Price
  • $611/SF
  • 16 Days On Market

  Last Sold Price $1,570,000

  Last Listing Agent Elyse Morris Elyse Harney Real Estate
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  /47

  $469,000

  • 3 Beds
  • 2 Baths
  • 1,298 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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  $290,000 Sold Jun 30, 2025

  15 Ferris Ln, Red Hook, NY 12571

  • Land
  • 9.25 Acres
  • $31,351 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 91 Days On Market

  Last Listing Agent PAULA REDMOND Corcoran Country Living

  15 Ferris Ln, Red Hook, NY 12571
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  Est $883,509 Not Listed For Sale

  218 Mountain Rd, Stanfordville, NY 12581

  • 3 Beds
  • 2.5 Baths
  • 2,486 Sq Ft
  • Built 2002

  218 Mountain Rd, Stanfordville, NY 12581

  Last Sold Summary

  • 29% Above List Price
  • $276/SF
  • 82 Days On Market

  Last Sold Price $685,000

  Last Listing Agent Savannah Miceli Century 21 Alliance-NP
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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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  $820,000 Sold Jan 16, 2026

  1388 Route 83, Pine Plains, NY 12567

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft
  • Built 1880

  Last Sold Summary

  • 11% Below List Price
  • $273/SF
  • 169 Days On Market

  Current Estimated Value $820,303

  Last Listing Agent Jill Rose Houlihan Lawrence Inc.

  1388 Route 83, Pine Plains, NY 12567
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  Est $313,196 Not Listed For Sale

  196 Mountain Rd, Stanfordville, NY 12581

  • 4 Beds
  • 1 Bath
  • 1,506 Sq Ft
  • Built 1879

  196 Mountain Rd, Stanfordville, NY 12581

  Last Sold Summary

  • 61% Above List Price
  • $129/SF
  • 51 Days On Market

  Last Sold Price $194,000

  Last Listing Agent Gail Saucier BHHS Hudson Valley Properties

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