Pine Plains, NY Homes

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  /23

  $1,695,000

  • 3 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  1504 Route 83, Pine Plains, NY 12567

  Privately set on 32 extraordinary acres in the heart of Shekomeko, this light-filled country retreat captures sweeping views of Stissing Mountain and the Catskills from nearly every vantage point. A long drive winds through the landscape to a thoughtfully sited three-bedroom, two and a half bath residence featuring vaulted ceilings, expansive windows, a wood stove, and exceptional southern,

  Byron Anderson Compass Greater NY, LLC

  1504 Route 83, Pine Plains, NY 12567
• 

  

  

  /26

  $240,000

  Sold Oct 10, 2025

  721 County Route 7, Pine Plains, NY 12567

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1820

  Last Sold Summary

  • 30% Below List Price
  • $171/SF
  • 418 Days On Market

  Current Estimated Value $263,016

  Last Listing Agent David Norman Hall Houlihan Lawrence Inc.

  721 County Route 7, Pine Plains, NY 12567
• 

  Est $507,262

  Not Listed For Sale

  16 Meusel Rd, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 3,012 Sq Ft
  • Built 2001

  16 Meusel Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 44 Days On Market
• 

  

  

  /26

  $4,250,000

  • 6 Beds
  • 5 Baths
  • 6,146 Sq Ft

  468 Tripp Rd, Pine Plains, NY 12567

  We welcome this 1834 restored farm into our Luxury Collection of Hudson Valley properties. This magnificent property makes the perfect country compound. Completely updated, restored and improved to also include a new addition on the main house. This 200 acre farm has all the privacy and beauty of a true country retreat. With such amenities as a converted dairy barn to an indoor tennis court

  George Langa Houlihan Lawrence Inc.

  468 Tripp Rd, Pine Plains, NY 12567
• 

  $711,000

  Sold Sep 22, 2025

  37 Stissing Mountain Dr, Pine Plains, NY 12567

  • 2 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Below List Price
  • $438/SF
  • 34 Days On Market

  Last Listing Agent Jason Nadeau Compass Greater NY, LLC

  37 Stissing Mountain Dr, Pine Plains, NY 12567
• 

  Est $363,954

  Not Listed For Sale

  50 Meusel Rd, Pine Plains, NY 12567

  • 3 Beds
  • 2.5 Baths
  • 1,760 Sq Ft
  • Built 1996

  50 Meusel Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 115 Days On Market
• 

  

  /29

  $588,000

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

  618 Bean River Rd, Millerton, NY 12546

  2-4 Lot Subdivision, includes secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone (possible subdivision into 2 lots) Plus adjoining 8 acre parcel. Adjoining 4 acre boha parcel can be added for $125,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show with

  David Birch Barns and Farms Realty LLC

  618 Bean River Rd, Millerton, NY 12546
• 

  $850,000

  Sold Feb 10, 2026

  390 Carpenter Hill Rd, Pine Plains, NY 12567

  • Land
  • 28.4 Acres
  • $29,930 per Acre

  Last Sold Summary

  • 29% Below List Price
  • 560 Days On Market

  Current Estimated Value $1,090,214

  Last Listing Agent Dan Kessler Compass Greater NY, LLC

  390 Carpenter Hill Rd, Pine Plains, NY 12567
• 

  Est $425,554

  Not Listed For Sale

  32 Britton St, Pine Plains, NY 12567

  • 3 Beds
  • 2.5 Baths
  • 2,002 Sq Ft
  • Built 2006

  32 Britton St, Pine Plains, NY 12567

  Last Sold Summary

  • 123 Days On Market
• 

  

  /19

  $575,000

  $75K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,646 Sq Ft

  60 Stissing Ave, Pine Plains, NY 12567

  SET ON A NICELY LANDSCAPED AND PRIVATE YARD IDEAL FOR GARDENING WITH 1.37 ACRES TOTAL-(HOUSE ON .65 ACRE AND AN ADJACENT BUILDING PARCEL OF .72 ACRE). THIS INVITING WELL MAINTAINED 3-BEDROOM, 2-BATH RANCH OFFERS COMFORT AND HAS HANDICAP ACCESSIBLE INTERIOR. FEATURES INCLUDE A LIVINGROOM WITH A FIREPLACE, LOVELY WOOD FLOORS THROUGHOUT AND A LARGE BASEMENT PERFECT FOR A WORKSHOP, RECREATION ROOM OR

  ANN SIMMONS Compass Greater NY, LLC

  60 Stissing Ave, Pine Plains, NY 12567
• 

  $104,000

  Sold Apr 26, 2026

  Knob Hill Rd N Knob Hill Rd, Stanfordville, NY 12581

  • Land
  • 4 Acres
  • $26,000 per Acre

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Peggy Santamorena Houlihan Lawrence Inc.

  Knob Hill Rd N Knob Hill Rd, Stanfordville, NY 12581
• 

  Est $424,395

  Not Listed For Sale

  53 Britton St, Pine Plains, NY 12567

  • 3 Beds
  • 1 Bath
  • 1,632 Sq Ft
  • Built 2002

  53 Britton St, Pine Plains, NY 12567

  Last Sold Summary

  • 14 Days On Market
• 

  

  /40

  $1,575,000

  • 3 Beds
  • 3 Baths
  • 2,433 Sq Ft

  617 Bean River Rd, Pine Plains, NY 12567

  Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit - the ultimate "entertainment perch" for soaking in breathtaking, panoramic valley

  Diana Bisselle William Pitt Sotheby's Int'l

  617 Bean River Rd, Pine Plains, NY 12567
• 

  $559,000

  Sold Jan 07, 2026

  540 Hicks Hill Rd, Stanfordville, NY 12581

  • 3 Beds
  • 2.5 Baths
  • 2,269 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $246/SF
  • 78 Days On Market

  Current Estimated Value $562,147

  Last Listing Agent Rita Longo Howard Hanna Rand Realty

  540 Hicks Hill Rd, Stanfordville, NY 12581
• 

  Est $363,832

  Not Listed For Sale

  26 Bowman Rd, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 3,010 Sq Ft
  • Built 1965

  26 Bowman Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 54 Days On Market
• 

  

  /21

  $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 Compound with adjoining 8 acre parcel for $588.000 and additional 4 acre boha parcel for $713,000. Adjoining parcels can be purchased separately for . Great location between Pine Plains Village and Millerton on quiet

  David Birch Barns and Farms Realty LLC

  618 Bean River Rd, Millerton, NY 12546
• 

  $850,000

  Sold Oct 14, 2025

  2365 Route 83, Pine Plains, NY 12567

  • 5 Beds
  • 2.5 Baths
  • 2,413 Sq Ft
  • Built 1830

  Last Sold Summary

  • 6% Below List Price
  • $352/SF
  • 54 Days On Market

  Current Estimated Value $860,688

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  2365 Route 83, Pine Plains, NY 12567
• 

  Est $372,057

  Not Listed For Sale

  14 Myrtle Ave, Pine Plains, NY 12567

  • 2 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1870

  14 Myrtle Ave, Pine Plains, NY 12567

  Last Sold Summary

  • 53 Days On Market
• 

  

  /50

  $639,000

  • 3 Beds
  • 2.5 Baths
  • 2,760 Sq Ft

  553 Lake Rd, Pine Plains, NY 12567

  Your Lakeside Sanctuary Awaits at 553 Lake Rd in Pine Plains NY. Imagine a life where your mornings begin not with an alarm, but with the gentle song of birds and the sun rising over the glassy waters of Twin Island Lake. Welcome to 553 Lake Road in Pine Plains—a home that doesn’t just offer a place to live, but a feeling of profound peace, warmth, and sanctuary.A Home Infused with Warmth and

  KELLY ROMANO Keller Williams Realty

  553 Lake Rd, Pine Plains, NY 12567
• 

  $10,850,000

  Sold Mar 02, 2026

  118 Finkle Rd, Ancramdale, NY 12503

  • 5 Beds
  • 3.5 Baths
  • 6,340 Sq Ft
  • Built 2008

  Last Sold Summary

  • $1,711/SF
  • 78 Days On Market

  Current Estimated Value $5,285,187

  Last Listing Agent PAULA REDMOND Corcoran Country Living

  118 Finkle Rd, Ancramdale, NY 12503
• 

  Est $456,806

  Not Listed For Sale

  36 Briarcliff Ln, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 2,142 Sq Ft
  • Built 1920

  36 Briarcliff Ln, Pine Plains, NY 12567

  Last Sold Summary

  • 35 Days On Market
• 

  

  /42

  $725,000

  Pending

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

  303 Mount 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 Mount Ross Rd, Pine Plains, NY 12567
• 

  $550,000

  Sold Sep 18, 2025

  4 Skiba Rd, Pine Plains, NY 12567

  • 2 Beds
  • 1.5 Baths
  • 1,774 Sq Ft
  • Built 1800

  Last Sold Summary

  • $310/SF
  • 31 Days On Market

  Current Estimated Value $599,011

  Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl

  4 Skiba Rd, Pine Plains, NY 12567
• 

  Est $483,783

  Not Listed For Sale

  4 Stissing Mountain Ln, Pine Plains, NY 12567

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • Built 1850

  4 Stissing Mountain Ln, Pine Plains, NY 12567

  Last Sold Summary

  • 19 Days On Market
• 

  

  /31

  $529,000

  Under Contract

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  367 Woods Ct, Ancramdale, NY 12503

  Exceptional ranch-style home on 3.25 acres offering partial mountain views and total privacy in a picturesque country setting. Bright, airy interior with 3 bedrooms and a completely tiled bathroom featuring a luxury rain shower. Thoughtful upgrades and move-in ready systems include a Mitsubishi AC, propane HVAC, overhead fans in the living room and primary bedroom, whole-house water filtration,

  Paul Crayton Coldwell Banker Advisor Realty

  367 Woods Ct, Ancramdale, NY 12503
• 

  $285,000

  Sold Aug 13, 2025

  6 Carla Terrace, Pine Plains, NY 12567

  • 4 Beds
  • 1.5 Baths
  • 1,328 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Below List Price
  • $215/SF
  • 48 Days On Market

  Current Estimated Value $308,544

  Last Listing Agent Theodore Weinstein REO Edge LLC

  6 Carla Terrace, Pine Plains, NY 12567
• 

  Est $463,101

  Not Listed For Sale

  1420 Route 83, Pine Plains, NY 12567

  • 5 Beds
  • 2.5 Baths
  • 2,456 Sq Ft
  • Built 1865

  1420 Route 83, Pine Plains, NY 12567

  Last Sold Summary

  • 55 Days On Market
• 

  

  /26

  $850,000

  • 3 Beds
  • 2 Baths
  • 2,700 Sq Ft

  608 Lake Rd, Pine Plains, NY 12567

  Discover the charm and possibilities of this private lakefront property set on 5.9 picturesque acres. This updated 1950's cottage features three plus bedrooms and two baths, with a bright, inviting interior that immediately feels like home. As soon as you step inside, you're welcomed by a direct view of Twin Island Lake, creating a stunning first impression. Relax on the decks and take in the

  ANN SIMMONS Compass Greater NY, LLC

  608 Lake Rd, Pine Plains, NY 12567
• 

  $537,500

  Sold Sep 09, 2025

  5 Myrtle Ave, Pine Plains, NY 12567

  • 4 Beds
  • 2 Baths
  • 2,605 Sq Ft
  • Built 1860

  Last Sold Summary

  • 10% Below List Price
  • $206/SF
  • 37 Days On Market

  Current Estimated Value $532,235

  Last Listing Agent Thomas Zengen Thomas Zengen

  5 Myrtle Ave, Pine Plains, NY 12567
• 

  /2

  Est $1,706,901

  Not Listed For Sale

  168 Fishwoods Rd, Red Hook, NY 12571

  • 3 Beds
  • 3 Baths
  • 2,121 Sq Ft
  • Built 1979

  168 Fishwoods Rd, Red Hook, NY 12571

  Last Sold Summary

  • 1 Day On Market
• 

  

  /14

  $525,000

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

  284 Hall Hill Rd, Ancram, NY 12502

  Discover the Charm of Country Living Escape 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 soak

  Kelly Harrison Taconic Valley Real Estate

  284 Hall Hill Rd, Ancram, NY 12502
• 

  

  /17

  $695,000

  Sold Sep 17, 2025

  60 County Route 7, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 1971

  Last Sold Summary

  • 9% Above List Price
  • $388/SF
  • 26 Days On Market

  Current Estimated Value $738,010

  Last Listing Agent David Norman Hall Houlihan Lawrence Inc.

  60 County Route 7, Pine Plains, NY 12567
• 

  Est $386,153

  Not Listed For Sale

  1645 Route 199, Stanfordville, NY 12581

  • 4 Beds
  • 2 Baths
  • 2,102 Sq Ft
  • Built 1930

  1645 Route 199, Stanfordville, NY 12581

  Last Sold Summary

  • 201 Days On Market
• 

  

  /15

  $799,000

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft

  153 Near Rd, Red Hook, NY 12571

  A 1949 original, 153 Near Road was fully reimagined in 2021. The house is sited on two acres off a county lane, yet is a short distance to Hudson, Red Hook, Pine Plains with easy access to the Taconic Parkway. The first floor features an open concept, the kitchen, dining and living spaces flow together without interruption, anchored by a kitchen island and warmed by a wood stove. Flooded with

  Jonathan Berry Upstate Down

  153 Near Rd, Red Hook, NY 12571
• 

  $850,000

  Sold Apr 27, 2026

  19 Friendship Ln, Red Hook, NY 12571

  • 5 Beds
  • 3.5 Baths
  • 5,650 Sq Ft
  • Built 1989

  Last Sold Summary

  • 10% Below List Price
  • $150/SF
  • 158 Days On Market

  Current Estimated Value $845,727

  Last Listing Agent Jeffery Dolfinger Century 21 Hudson Valley Rlty.

  19 Friendship Ln, Red Hook, NY 12571
• 

  Est $336,621

  Not Listed For Sale

  300 South Rd, Stanfordville, NY 12581

  • 3 Beds
  • Built 1951

  300 South Rd, Stanfordville, NY 12581

  Last Sold Summary

  • 21 Days On Market
• 

  

  /26

  $3,950,000

  70 Ryan Rd, Pine Plains, NY 12567

  An intoxicating opportunity to own a 343 acre swath of spectacular farmland, proudly eligible for the National Register of Historic Places, that encompasses several impressive barn structures, plus a fully functioning distillery and tasting room. Dutch's Spirits, on Harvest Homestead Farm, is a distillery with a legacy! Built in 1932 toward the end of the Prohibition Era, it was Dutchess County's

  Andrew Gates Houlihan Lawrence, Inc.

  70 Ryan Rd, Pine Plains, NY 12567
• 

  

  /35

  $950,000

  Sold Nov 25, 2025

  235 Knob Hill Rd, Stanfordville, NY 12581

  • 4 Beds
  • 3 Baths
  • 3,980 Sq Ft
  • Built 1850

  Last Sold Summary

  • 5% Below List Price
  • $239/SF
  • 103 Days On Market

  Last Listing Agent Jeannine Simmons Corcoran Country Living

  235 Knob Hill Rd, Stanfordville, NY 12581
• 

  Est $304,163

  Not Listed For Sale

  Unlisted Address

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1950

  Unlisted Address

  Last Sold Summary

  • 52 Days On Market
• 

  

  /50

  $9,500,000

  • 5 Beds
  • 7 Baths
  • 6,875 Sq Ft

  506 Silvernail Rd, Pine Plains, NY 12567

  A rare offering of enduring beauty and thoughtful design, this extraordinary modern farmhouse--built in 2019--stands as a true masterpiece set on 52.32 acres of rolling landscape, with sweeping views of mountains, open hills, and the Roeliff Jansen Kill. Spanning 6,875 square feet, the residence blends refined craftsmanship with a warm, livable elegance. Reclaimed 19th-century pine floors with

  Paula Redmond Corcoran Country Living - Mill

  506 Silvernail Rd, Pine Plains, NY 12567

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