Pine Plains, NY Homes

• 

  $520,000

  Sold Jul 28, 2025

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

  • 4 Beds
  • 4 Baths
  • 3,928 Sq Ft
  • Built 1880

  Last Sold Summary

  • 13% Below List Price
  • $132/SF
  • 285 Days On Market

  Current Estimated Value $782,885

  Last Listing Agent Larry Havens Havens Real Estate

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

  Est $644,224

  Not Listed For Sale

  250 South Rd, Stanfordville, NY 12581

  • 2 Beds
  • 2 Baths
  • 1,990 Sq Ft
  • Built 1998

  250 South Rd, Stanfordville, NY 12581

  Last Sold Summary

  • 56 Days On Market
• 

  

  

  /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
• 

  

  

  /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 $457,711

  Last Listing Agent Matthew Snyder Compass, Hillsdale

  23 Myrtle Ave Unit 25, Pine Plains, NY 12567
• 

  Est $764,255

  Not Listed For Sale

  351 Willow Glen Rd, Red Hook, NY 12571

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2002

  351 Willow Glen Rd, Red Hook, NY 12571

  Last Sold Summary

  • 18 Days On Market
• 

  

  /23

  $419,500

  $6K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,860 Sq Ft

  211 Sigler Rd, Pine Plains, NY 12567

  Tucked away on a quiet country road and surrounded by open fields and natural beauty, this charming ranch-style home offers the perfect blend of comfort, flexibility, and peaceful country living. Set on a manageable .25-acre lot this 3-bedroom, 2-bath home features approximately 1,860 square feet of living space with hardwood floors throughout the main level. The fully finished lower level

  Richard Brenner Rich Brenner Realty, LLC

  211 Sigler Rd, 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 $1,004,943

  Last Listing Agent SHERI SCEROLER Four Seasons Sothebys Intl

  660 County Route 7, Pine Plains, NY 12567
• 

  

  /29

  Est $835,477

  Not Listed For Sale

  348 Willow Glen Rd, Red Hook, NY 12571

  • 2 Beds
  • 2.5 Baths
  • 2,092 Sq Ft
  • Built 1968

  348 Willow Glen Rd, Red Hook, NY 12571

  Last Sold Summary

  • 58 Days On Market
• 

  

  /27

  $169,900

  $130K PRICE DROP

  • 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
• 

  $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
• 

  Est $584,405

  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
• 

  

  /28

  $825,000

  • 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
• 

  $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 $378,969

  Last Listing Agent Margaret Mondello Margaret Mondello Real Estate

  107 Near Rd, Red Hook, NY 12571
• 

  Est $433,662

  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
• 

  

  /42

  $725,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 2,028 Sq Ft

  303 Mt Ross Rd, Pine Plains, NY 12567

  Thoughtfully restored while preserving its historic character, this circa-1820 farmhouse blends timeless craftsmanship with modern comfort and efficiency. Original hand-hewn beams and a fieldstone foundation anchor the home’s authentic charm, while extensive upgrades throughout create a move-in ready retreat designed for year-round living. The open floor plan seamlessly connects the dining room,

  Kyle Irwin Corcoran Country Living

  303 Mt Ross Rd, 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
• 

  Est $282,950

  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
• 

  

  /14

  $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

  Elyse Morris Elyse Harney Real Estate

  1533-1539 Route 83, 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
• 

  Est $295,777

  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
• 

  

  /10

  $140,000

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

  66 Ryan Rd, Pine Plains, NY 12567

  BUILD YOUR DREAM HAVEN WITH STISSING MOUNTAIN VIEWS Embrace the perfect blend of tranquility, history, and vibrant Hudson Valley living on this exceptional 3.45-acre elevated homesite in the heart of Pine Plains. Already Board of Health approved for a 4-bedroom residence, this remarkable parcel offers a rare opportunity to design a custom retreat surrounded by nature. Enjoy an idyllic lifestyle

  Vida Odescalchi Legacy Land & Homes LLC

  66 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 $517,986

  Last Listing Agent Catherine Mondello Mondello Upstate Properties

  143 Ryan Rd, Pine Plains, NY 12567
• 

  Est $351,701

  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
• 

  

  /48

  $3,995,000

  $400K 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
• 

  $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 $285,358

  Last Listing Agent Susan Whalen George T Whalen Real Estate

  46 Myrtle Ave, Pine Plains, NY 12567
• 

  Est $381,476

  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
• 

  

  /14

  $525,000

  • 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
• 

  $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 $376,197

  Last Listing Agent Janet Myer Houlihan Lawrence Inc.

  3807 Route 199, Pine Plains, NY 12567
• 

  Est $1,019,963

  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
• 

  

  /7

  $197,000

  $2K PRICE DROP

  • Land
  • 8.59 Acres
  • $22,934 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
• 

  $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 $372,725

  Last Listing Agent Brad Rebillard DUTCHESS COUNTRY REALTY INC. M

  48 Woodside St, Pine Plains, NY 12567
• 

  Est $382,731

  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
• 

  

  /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
• 

  

  /37

  $665,000

  Sold Aug 15, 2025

  2067 County Road 83, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Built 1810

  Last Sold Summary

  • 1% Below List Price
  • $405/SF
  • 27 Days On Market

  Last Listing Agent William Golan Compass Greater NY, LLC

  2067 County Road 83, 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
• 

  

  /29

  $1,250,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  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 ready and designed for year-round

  Bill Flood Houlihan Lawrence, Inc.

  216 North Rd, Red Hook, NY 12571
• 

  $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 $415,538

  Last Listing Agent Michael Cahill HomeSmart Homes & Estates

  4 Antler Club Rd, Pine Plains, NY 12567
• 

  

  /35

  Est $681,374

  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
• 

  $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 $1,142,623

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  84 Green Hill Rd, Pine Plains, NY 12567
• 

  

  /25

  Est $1,330,964

  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

Showing Results 121 - 160, Page 4 of 18