2,744

Pine Plains, NY Homes

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  • 82 Maple Hill Ln, Pine Plains, NY 12567
    82 Maple Hill Ln, Pine Plains, NY 12567
    82 Maple Hill Ln, Pine Plains, NY 12567
    /27

    $750,000

    • 4 Beds
    • 2.5 Baths
    • 3,108 Sq Ft

    82 Maple Hill Ln, Pine Plains, NY 12567

    Light-filled 2006 home blends privacy with effortless convenience. An open-air front porch and a generous backyard frame inviting indoor/outdoor living. Inside, the living room centers on a charming stove, while the chef’s kitchen echoes the home’s airy feel with an island and open plan ideal for entertaining. The first-floor primary suite is a private retreat with a freestanding tub and tiled

    Liza Reiss Elyse Harney Real Estate

    82 Maple Hill Ln, Pine Plains, NY 12567
  • 23 Myrtle Ave Unit 25, Pine Plains, NY 12567
    23 Myrtle Ave Unit 25, Pine Plains, NY 12567
    23 Myrtle Ave Unit 25, Pine Plains, NY 12567
    /49

    $835,000

    Sold Jun 23, 2026

    23 Myrtle Ave Unit 25, Pine Plains, NY 12567

    • 4 Beds
    • 2.5 Baths
    • 2,425 Sq Ft
    • Built 1865

    Last Sold Summary

    • 1% Above List Price
    • $344/SF
    • 13 Days On Market

    Current Estimated Value $493,713

    Last Listing Agent Matthew Snyder Compass, Hillsdale

    23 Myrtle Ave Unit 25, Pine Plains, NY 12567
    • 357 North Rd, Red Hook, NY 12571

      Est $581,491

      Not Listed For Sale

      357 North Rd, Red Hook, NY 12571

      • 3 Beds
      • 2.5 Baths
      • 3,980 Sq Ft
      • Built 1962
      357 North Rd, Red Hook, NY 12571

      Last Sold Summary

      • 114 Days On Market

      Last Listing Agent Patricia Dantzic Upstate Down

  • 211 Sigler Rd, Pine Plains, NY 12567
    211 Sigler Rd, Pine Plains, NY 12567
    211 Sigler Rd, Pine Plains, NY 12567
    /25

    $409,000

    $16K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,860 Sq Ft

    211 Sigler Rd, Pine Plains, NY 12567

    More space and flexibility than you might expect! Set along a quiet country road in the Town of Gallatin, just outside Pine Plains, this 3-bedroom ranch offers approximately 1,860 square feet of living space with a finished lower level, providing plenty of room to spread out, work from home, entertain, or accommodate guests.The main level features hardwood floors, a full bathroom, three

    Richard Brenner Rich Brenner Realty, LLC

    211 Sigler Rd, Pine Plains, NY 12567
  • 660 County Route 7, Pine Plains, NY 12567

    $1,100,000

    Sold Sep 19, 2025

    660 County Route 7, Pine Plains, NY 12567

    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft
    • Built 1850

    Last Sold Summary

    • 23% Above List Price
    • $1,000/SF
    • 8 Days On Market

    Current Estimated Value $1,041,825

    Last Listing Agent SHERI SCEROLER Four Seasons Sothebys Intl

    660 County Route 7, Pine Plains, NY 12567
    • 21 Hamlet Ln, Red Hook, NY 12571

      Est $435,299

      Not Listed For Sale

      21 Hamlet Ln, Red Hook, NY 12571

      • 2 Beds
      • 2 Baths
      • 1,408 Sq Ft
      • Built 1960
      21 Hamlet Ln, Red Hook, NY 12571

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent Jessica Hill Redfin Real Estate

  • 245 Hicks Hill Rd, Stanfordville, NY 12581
    245 Hicks Hill Rd, Stanfordville, NY 12581
    245 Hicks Hill Rd, Stanfordville, NY 12581
    /27

    $164,900

    $135K PRICE DROP Pending
    • 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
  • 0 New York 199, Stanfordville, NY 12581

    $160,000

    Sold Jun 09, 2026

    0 New York 199, Stanfordville, NY 12581

    • Land
    • 16 Acres
    • $10,000 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 211 Days On Market

    Last Listing Agent MARIE MONROE BHHS Hudson Valley Properties

    0 New York 199, Stanfordville, NY 12581
    • 26 Hamlet Ln, Red Hook, NY 12571

      Est $273,520

      Not Listed For Sale

      26 Hamlet Ln, Red Hook, NY 12571

      • 2 Beds
      • 1 Bath
      • 800 Sq Ft
      • Built 1940
      26 Hamlet Ln, Red Hook, NY 12571

      Last Sold Summary

      • 147 Days On Market

      Last Listing Agent KEVIN HOWE BHHS Hudson Valley Properties

  • 82 Near Rd, Red Hook, NY 12571
    82 Near Rd, Red Hook, NY 12571
    82 Near Rd, Red Hook, NY 12571
    /28

    $799,000

    $26K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,304 Sq Ft

    82 Near Rd, Red Hook, NY 12571

    Beautifully reimagined 1924 home blends character with modern comfort and thoughtful design. Completely renovated in 2020 the residence offers 2,304 finished square feet with 3 bedrooms and 3 full baths. Vaulted ceilings, exposed beams abundant windows and an open-concept floor plan create a sense of beauty and spaciousness. The main level features warm wood floors, radiant heat throughout, and

    Linda Lindsay Upstate Down

    82 Near Rd, Red Hook, NY 12571
  • 107 Near Rd, Red Hook, NY 12571

    $354,700

    Sold Dec 23, 2025

    107 Near Rd, Red Hook, NY 12571

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1934

    Last Sold Summary

    • 27% Below List Price
    • $253/SF
    • 178 Days On Market

    Current Estimated Value $363,778

    Last Listing Agent Margaret Mondello Margaret Mondello Real Estate

    107 Near Rd, Red Hook, NY 12571
    • 97 North Rd, Red Hook, NY 12571

      Est $300,198

      Not Listed For Sale

      97 North Rd, Red Hook, NY 12571

      • 2 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 1951
      97 North Rd, Red Hook, NY 12571

      Last Sold Summary

      • 77 Days On Market

      Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  • 66 Ryan Rd, Pine Plains, NY 12567
    66 Ryan Rd, Pine Plains, NY 12567
    66 Ryan Rd, Pine Plains, NY 12567
    /11

    $140,000

    • Land
    • 3.45 Acres
    • $40,580 per Acre

    66 Ryan Rd, Pine Plains, NY 12567

    Ready to build your Hudson Valley dream home? Save numerous months of engineering expense and time with this fully Board of Health Approved 3.45-acre parcel, pre-tested and permitted for a 4-bedroom residence! (Please note: the image of the home in the listing pictures is a POSSIBLE concept created by AI using the land photos.)A rough-cut driveway leads up to a secluded, elevated building

    Vida Odescalchi Legacy Land & Homes LLC

    66 Ryan Rd, Pine Plains, NY 12567
  • 174 County Route 11, Pine Plains, NY 12567
    174 County Route 11, Pine Plains, NY 12567
    174 County Route 11, Pine Plains, NY 12567
    /37

    $1,142,500

    Sold Jul 01, 2026

    174 County Route 11, Pine Plains, NY 12567

    • 4 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1948

    Last Sold Summary

    • 7% Below List Price
    • $605/SF
    • 231 Days On Market

    Last Listing Agent Paula Redmond Corcoran Country Living - Mill

    174 County Route 11, Pine Plains, NY 12567
    • 110 South Rd, Red Hook, NY 12571

      Est $361,124

      Not Listed For Sale

      110 South Rd, Red Hook, NY 12571

      • 2 Beds
      • 1 Bath
      • 1,152 Sq Ft
      • Built 1965
      110 South Rd, Red Hook, NY 12571

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Jeffery Dolfinger Century 21 Hudson Valley Rlty.

  • 479 Prospect Hill Rd, Pine Plains, NY 12567
    479 Prospect Hill Rd, Pine Plains, NY 12567
    479 Prospect Hill Rd, Pine Plains, NY 12567
    /55

    $499,000

    Pending
    • 4 Beds
    • 1.5 Baths
    • 2,108 Sq Ft

    479 Prospect Hill Rd, Pine Plains, NY 12567

    Framed by open fields on a peaceful country road, this antique Pine Plains farmhouse is the kind of home that tells its story through every beam, floorboard, and well-worn detail. Just minutes from Chaseholm Farm and the village center, it offers a setting that feels wonderfully rural while remaining close to everyday conveniences. Inside, hand-hewn beams, original hardwood floors, and

    Paige Backhaus William Raveis Real Estate

    479 Prospect Hill Rd, Pine Plains, NY 12567
  • 198 Sigler Rd, Pine Plains, NY 12567

    $825,000

    Sold Nov 04, 2025

    198 Sigler Rd, Pine Plains, NY 12567

    • 5 Beds
    • 3.5 Baths
    • 2,714 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $304/SF
    • 108 Days On Market

    Last Listing Agent Kimberly Baker BHHS Hudson Valley Properties

    198 Sigler Rd, Pine Plains, NY 12567
    • 38 County Route 7, Pine Plains, NY 12567

      Est $422,348

      Not Listed For Sale

      38 County Route 7, Pine Plains, NY 12567

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1970
      38 County Route 7, Pine Plains, NY 12567

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent PAULA REDMOND Corcoran Country Living

  • 1515-1517 County Road 83, Pine Plains, NY 12567
    1515-1517 County Road 83, Pine Plains, NY 12567
    1515-1517 County Road 83, Pine Plains, NY 12567
    /48

    $3,895,000

    $500K PRICE DROP
    • 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 just under 10 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white

    Oliver Brown Houlihan Lawrence Inc.

    1515-1517 County Road 83, Pine Plains, NY 12567
  • 143 Ryan Rd, Pine Plains, NY 12567

    $575,000

    Sold Jan 23, 2026

    143 Ryan Rd, Pine Plains, NY 12567

    • 4 Beds
    • 2.5 Baths
    • 2,580 Sq Ft
    • Built 2010

    Last Sold Summary

    • $223/SF
    • 100 Days On Market

    Current Estimated Value $588,749

    Last Listing Agent Catherine Mondello Mondello Upstate Properties

    143 Ryan Rd, Pine Plains, NY 12567
    • 102 Hall Hill Rd, Ancram, NY 12502

      Est $1,122,615

      Not Listed For Sale

      102 Hall Hill Rd, Ancram, NY 12502

      • 3 Beds
      • 1.5 Baths
      • 2,268 Sq Ft
      • Built 1988
      102 Hall Hill Rd, Ancram, NY 12502

      Last Sold Summary

      • 147 Days On Market

      Last Listing Agent Antoinette Caruso Stonewall Realty Group LLC

  • 284 Hall Hill Rd Stop 18, Ancram, NY 12502
    284 Hall Hill Rd Stop 18, Ancram, NY 12502
    284 Hall Hill Rd Stop 18, Ancram, NY 12502
    /14

    $495,000

    $30K PRICE DROP
    • 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
  • 46 Myrtle Ave, Pine Plains, NY 12567

    $275,000

    Sold Dec 08, 2025

    46 Myrtle Ave, Pine Plains, NY 12567

    • 2 Beds
    • 3 Baths
    • 1,728 Sq Ft
    • Built 1875

    Last Sold Summary

    • 20% Below List Price
    • $159/SF
    • 86 Days On Market

    Current Estimated Value $291,232

    Last Listing Agent Susan Whalen George T Whalen Real Estate

    46 Myrtle Ave, Pine Plains, NY 12567
    • 712 County Route 7, Pine Plains, NY 12567

      Est $366,764

      Not Listed For Sale

      712 County Route 7, Pine Plains, NY 12567

      • 2 Beds
      • 1.5 Baths
      • 1,728 Sq Ft
      • Built 1800
      712 County Route 7, Pine Plains, NY 12567

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent PAULA REDMOND Corcoran Country Living

  • 622 Bean River Rd, Pine Plains, NY 12567
    622 Bean River Rd, Pine Plains, NY 12567
    622 Bean River Rd, Pine Plains, NY 12567
    /7

    $195,000

    $4K PRICE DROP
    • Land
    • 8.59 Acres
    • $22,701 per Acre

    622 Bean River Rd, Pine Plains, NY 12567

    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 389,000. Owner financing possible.

    David Birch Barns & Farms Realty, LLC

    622 Bean River Rd, Pine Plains, NY 12567
  • 3807 Route 199, Pine Plains, NY 12567

    $374,000

    Sold Mar 09, 2026

    3807 Route 199, Pine Plains, NY 12567

    • 3 Beds
    • 1 Bath
    • 1,573 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Above List Price
    • $238/SF
    • 22 Days On Market

    Current Estimated Value $380,403

    Last Listing Agent Janet Myer Houlihan Lawrence Inc.

    3807 Route 199, Pine Plains, NY 12567
    • 105 Mill Hill Rd, Pine Plains, NY 12567

      Not Listed For Sale

      105 Mill Hill Rd, Pine Plains, NY 12567

      • 4 Beds
      • 2.5 Baths
      • 3,500 Sq Ft
      • Built 1870
      105 Mill Hill Rd, Pine Plains, NY 12567

      Last Sold Summary

      • 562 Days On Market

      Last Listing Agent ANN SIMMONS Compass Greater NY, LLC

  • 0 Mount Ross Rd, Pine Plains, NY 12567
    0 Mount Ross Rd, Pine Plains, NY 12567
    0 Mount Ross Rd, Pine Plains, NY 12567
    /6

    $219,000

    • Land
    • 12.78 Acres
    • $17,136 per Acre

    0 Mount Ross Rd, Pine Plains, NY 12567

    Perched on top of the world, this 12.78 acre sanctuary remains completely untouched, offering a rare blend of tranquility and possibility. The future home site is wrapped in mature forest, creating total privacy with the potential for inspiring seasonal vistas. Enjoy the convenience of being just minutes from downtown Pine Plains, with effortless access to the Taconic State Parkway. A deeded

    Larry Havens Havens Real Estate

    0 Mount Ross Rd, Pine Plains, NY 12567
  • 48 Woodside St, Pine Plains, NY 12567

    $360,000

    Sold Sep 25, 2025

    48 Woodside St, Pine Plains, NY 12567

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Built 2001

    Last Sold Summary

    • 7% Below List Price
    • $281/SF
    • 95 Days On Market

    Current Estimated Value $377,217

    Last Listing Agent Brad Rebillard DUTCHESS COUNTRY REALTY INC. M

    48 Woodside St, Pine Plains, NY 12567
    • 607 County Route 7, Ancram, NY 12502
      607 County Route 7, Ancram, NY 12502
      607 County Route 7, Ancram, NY 12502
      /35

      Est $741,049

      Not Listed For Sale

      607 County Route 7, Ancram, NY 12502

      • 4 Beds
      • 1.5 Baths
      • 2,720 Sq Ft
      • Built 1840
      607 County Route 7, Ancram, NY 12502

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Leslie Foti Coldwell Banker Village Green

  • 4 Antler Club Rd, Pine Plains, NY 12567

    $280,500

    Sold Oct 03, 2025

    4 Antler Club Rd, Pine Plains, NY 12567

    • 2 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1950

    Last Sold Summary

    • 23% Below List Price
    • $173/SF
    • 231 Days On Market

    Current Estimated Value $427,837

    Last Listing Agent Michael Cahill HomeSmart Homes & Estates

    4 Antler Club Rd, Pine Plains, NY 12567
    • 12 Skiba Rd, Pine Plains, NY 12567
      12 Skiba Rd, Pine Plains, NY 12567
      12 Skiba Rd, Pine Plains, NY 12567
      /25

      Est $1,400,056

      Not Listed For Sale

      12 Skiba Rd, Pine Plains, NY 12567

      • 3 Beds
      • 1.5 Baths
      • 2,510 Sq Ft
      • Built 2002
      12 Skiba Rd, Pine Plains, NY 12567

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Ann Simmons Past Member

  • 84 Green Hill Rd, Pine Plains, NY 12567

    $1,100,000

    Sold Dec 18, 2025

    84 Green Hill Rd, Pine Plains, NY 12567

    • 4 Beds
    • 2.5 Baths
    • 3,220 Sq Ft
    • Built 1980

    Last Sold Summary

    • 19% Above List Price
    • $342/SF
    • 27 Days On Market

    Current Estimated Value $1,104,576

    Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

    84 Green Hill Rd, Pine Plains, NY 12567
    • 60 Near Rd, Red Hook, NY 12571

      Est $790,240

      Not Listed For Sale

      60 Near Rd, Red Hook, NY 12571

      • 3 Beds
      • 2 Baths
      • 2,012 Sq Ft
      • Built 1977
      60 Near Rd, Red Hook, NY 12571

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Linda Lindsay Upstate Down

  • 717 County Route 7, Pine Plains, NY 12567
    717 County Route 7, Pine Plains, NY 12567
    717 County Route 7, Pine Plains, NY 12567
    /45

    $850,000

    Sold Oct 31, 2025

    717 County Route 7, Pine Plains, NY 12567

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • Built 1870

    Last Sold Summary

    • $472/SF
    • 39 Days On Market

    Current Estimated Value $829,270

    Last Listing Agent Sarah Lipsky William Pitt Sothebys Intn'l

    717 County Route 7, Pine Plains, NY 12567
    • 82 Skiba Rd, Pine Plains, NY 12567

      Est $762,926

      Not Listed For Sale

      82 Skiba Rd, Pine Plains, NY 12567

      • 3 Beds
      • 2 Baths
      • 2,156 Sq Ft
      • Built 1975
      82 Skiba Rd, Pine Plains, NY 12567

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Dan Kessler Compass Greater NY, LLC

    • 246 County Route 11, Pine Plains, NY 12567
      246 County Route 11, Pine Plains, NY 12567
      /2

      Est $620,727

      Not Listed For Sale

      246 County Route 11, Pine Plains, NY 12567

      • 3 Beds
      • 1 Bath
      • 1,168 Sq Ft
      • Built 1951
      246 County Route 11, Pine Plains, NY 12567

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Andrew Gates Houlihan Lawrence, Inc.

    • 21 Finkle Rd Unit 5, Ancramdale, NY 12503
      21 Finkle Rd Unit 5, Ancramdale, NY 12503
      21 Finkle Rd Unit 5, Ancramdale, NY 12503
      /40

      Est $2,012,959

      Not Listed For Sale

      21 Finkle Rd Unit 5, Ancramdale, NY 12503

      • 3 Beds
      • 2.5 Baths
      • 3,997 Sq Ft
      • Built 1989
      21 Finkle Rd Unit 5, Ancramdale, NY 12503

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Paula Redmond Corcoran Country Living - Mill

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

      Est $789,311

      Not Listed For Sale

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

      • 4 Beds
      • 4 Baths
      • 3,928 Sq Ft
      • Built 1880
      115-133 Mount Ross Rd, Pine Plains, NY 12567

      Last Sold Summary

      • 285 Days On Market

      Last Listing Agent Larry Havens Havens Real Estate

    • 2812 W Church St, Pine Plains, NY 12567

      Not Listed For Sale

      2812 W Church St, Pine Plains, NY 12567

      • 460 Sq Ft
      • Built 1965
      2812 W Church St, Pine Plains, NY 12567

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Terese Mondello Mondello Upstate Properties

Showing Results 121 - 160, Page 4 of 18

New York Dutchess County

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