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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  $2,760 - $2,940 per month

  Stissing Farms

  2 Beds

  51 Hillside Rd, Pine Plains, NY 12567

  Live the way you've always wanted without compromising style or quality. At Stissing Farm Townhomes, our apartment residences are designed with you in mind. Now you really can have it all . . . lifestyle included.Pine Plains was named One of the Best Small Towns in New York by !

  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 $726,387

  Last Listing Agent Joseph Iannibelli Keller Williams NY Realty

  546 Hicks Hill Rd, Stanfordville, NY 12581
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  /16

  Est $237,593 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  3066 Church St, Pine Plains, NY 12567

  3066 Church St, Pine Plains, NY 12567
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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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  /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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  $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 $425,000

  Last Listing Agent Jason Schobert eXp Realty

  1601 Route 199, Red Hook, NY 12571
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  Est $1,691,095 Not Listed For Sale

  454 Bean River Rd, Pine Plains, NY 12567

  454 Bean River Rd, 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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  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  2704 Ny-199 Unit Apartment for rent, Pine Plains, NY 12567

  3 Bedrooms-2 bathroom - Full kitchen and huge dining area- Living room - Utilities include heating, hot water, electric- Free parking in the lot- Brand new renovations including new flooring, new windows, new insulation.

  2704 Ny-199 Unit Apartment for rent, Pine Plains, NY 12567
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  $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 $2,071,970 Not Listed For Sale

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

  88 Friar Tuck Rd, Ancramdale, NY 12503

  88 Friar Tuck Rd, Ancramdale, NY 12503
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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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  /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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  $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 $392,131

  Last Listing Agent Michael Tellerday Houlihan Lawrence Inc.

  285 South Rd, Stanfordville, NY 12581
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  Est $557,501 Not Listed For Sale

  • Studio
  • 4,032 Sq Ft

  7795 S Main St, Pine Plains, NY 12567

  7795 S Main St, Pine Plains, NY 12567
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  $490,000

  • 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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  $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

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

  7604 Route 82, Pine Plains, NY 12567

  7604 Route 82, Pine Plains, NY 12567
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  $4,950,000 Pending

  • 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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  $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

  Last Listing Agent Blake Michaud Serhant LLC

  34 Myrtle Ave, Pine Plains, NY 12567
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  Not Listed For Sale

  0 County Route 11, Pine Plains, NY 12567

  0 County Route 11, Pine Plains, NY 12567
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  $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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  $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 $829,108

  Last Listing Agent Diana Bisselle William Pitt Sothebys Int Rlty

  2854 Church St, Pine Plains, 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
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  /5

  $140,000

  • Land
  • 1.5 Acres
  • $93,333 per Acre

  25 Five Roses E, Ancram, NY 12502

  Ready to build, this 1.5-acre parcel is located on a peaceful country road in the scenic town of Ancram, Columbia County, New York. Board of Health approval is already in place for a four-bedroom residence, saving valuable time in the building process. The property is well-prepared with an installed septic system, existing well, driveway, and underground electric service run from the road to a

  Richard Brenner RICH BRENNER REALTY LLC

  25 Five Roses E, Ancram, NY 12502
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  /3

  $335,000 Sold Jan 30, 2025

  599 Bean River Rd, Millerton, NY 12546

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1950

  Last Sold Summary

  • 4% Below List Price
  • $258/SF
  • 53 Days On Market

  Current Estimated Value $373,675

  Last Listing Agent Christopher Virtuoso Keller Williams Realty HV Nort

  599 Bean River Rd, Millerton, NY 12546
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  Est $616,580 Not Listed For Sale

  • 3 Beds

  308 Hall Hill Rd, Ancram, NY 12502

  308 Hall Hill Rd, Ancram, NY 12502
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  $239,900

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  16 Ryan Rd, Pine Plains, NY 12567

  Adorable 3-bedroom ranch ready for you to move in. Ideal for First-time home buyers or anyone tired of paying rent. Bright eat in kitchen, living room with fireplace. door that leads out to large back yard. Close to schools, Village of Pine Plains and TSP. County living at its best. Additional Information: HeatingFuel:Oil Above Ground,

  Joseph Lukic Compass Greater NY, LLC

  16 Ryan Rd, 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 $325,945 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft

  44 Conklin Hill Rd, Stanfordville, NY 12581

  44 Conklin Hill Rd, Stanfordville, NY 12581
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  /31

  $549,000

  • Land
  • 43.69 Acres
  • $12,566 per Acre

  Tbd Hicks Hill Rd, Pine Plains, NY 12567

  Enjoy nature on your own 43 scenic acres located on Hicks Hill Road and additional access from Knob Hill Road, which is across from apprx 600 acres of protected land that can not be developed offering exceptional long term privacy. A versatile existing barn provides potential for a variety of uses. With over 1,400 feet of road frontage on Hicks Hill Road and electric available on the property,

  Jeannine Simmons Corcoran Country Living

  Tbd Hicks Hill Rd, 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

  Last Listing Agent Jill Rose Houlihan Lawrence Inc.

  1388 Route 83, Pine Plains, NY 12567
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  Est $929,181 Not Listed For Sale

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

  140 Mountain Rd, Stanfordville, NY 12581

  140 Mountain Rd, Stanfordville, NY 12581
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  $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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  $520,000 Sold Dec 30, 2025

  30 N Main St, Pine Plains, NY 12567

  • 4 Beds
  • 2.5 Baths
  • 3,180 Sq Ft
  • Built 1880

  Last Sold Summary

  • 13% Below List Price
  • $164/SF
  • 99 Days On Market

  Last Listing Agent Arleen Shepley Elyse Harney Real Estate

  30 N Main St, Pine Plains, NY 12567
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  Est $912,618 Not Listed For Sale

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

  218 Mountain Rd, Stanfordville, NY 12581

  218 Mountain Rd, Stanfordville, NY 12581
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  $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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  $250,000 Sold Apr 01, 2025

  97 North Rd, Red Hook, NY 12571

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1951

  Last Sold Summary

  • 2% Below List Price
  • $200/SF
  • 77 Days On Market

  Current Estimated Value $264,057

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  97 North Rd, Red Hook, NY 12571
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  Est $324,229 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,506 Sq Ft

  196 Mountain Rd, Stanfordville, NY 12581

  196 Mountain Rd, Stanfordville, NY 12581

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