Pine Plains, NY Homes

• 

  Est $355,246

  Not Listed For Sale

  3 Carla Terrace, Pine Plains, NY 12567

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1968

  3 Carla Terrace, Pine Plains, NY 12567

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Andrea Replansky BHHS Hudson Valley Properties
• 

  

  

  /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
• 

  $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 $573,888

  Last Listing Agent Rita Longo Howard Hanna Rand Realty

  540 Hicks Hill Rd, Stanfordville, NY 12581
• 

  Est $526,877

  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

  Last Listing Agent Diane Zani BHHS Hudson Valley Properties
• 

  

  

  /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
• 

  $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 $910,897

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  2365 Route 83, Pine Plains, NY 12567
• 

  Est $395,706

  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

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC
• 

  

  /29

  $565,000

  $23K PRICE DROP

  • 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
• 

  $1,055,000

  Sold May 22, 2026

  216 North Rd, Red Hook, NY 12571

  • 4 Beds
  • 2.5 Baths
  • 3,360 Sq Ft
  • Built 1996

  Last Sold Summary

  • 16% Below List Price
  • $314/SF
  • 188 Days On Market

  Current Estimated Value $1,167,359

  Last Listing Agent Bill Flood Houlihan Lawrence Inc.

  216 North Rd, Red Hook, NY 12571
• 

  Est $458,354

  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

  Last Listing Agent Melissa Pettinella Century 21 Alliance Realty Grp
• 

  

  /19

  $540,000

  $110K 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
• 

  $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 $5,411,206

  Last Listing Agent PAULA REDMOND Corcoran Country Living

  118 Finkle Rd, Ancramdale, NY 12503
• 

  Est $418,303

  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

  Last Listing Agent Catherine Mondello Mondello Upstate Properties
• 

  

  /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 $565.000 and additional 4 acre boha parcel for $689,000. 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
• 

  $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 $573,339

  Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl

  4 Skiba Rd, Pine Plains, NY 12567
• 

  Est $340,490

  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

  Last Listing Agent Shannon Martin BHHS Hudson Valley Properties
• 

  

  /50

  $639,000

  Pending

  • 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
• 

  

  /42

  $800,000

  Sold Jul 23, 2026

  303 Mount Ross Rd, Pine Plains, NY 12567

  • 3 Beds
  • 1.5 Baths
  • 2,028 Sq Ft
  • Built 1820

  Last Sold Summary

  • 10% Above List Price
  • $394/SF
  • 26 Days On Market

  Last Listing Agent Kyle Irwin Corcoran Country Living

  303 Mount Ross Rd, Pine Plains, NY 12567
• 

  Est $448,085

  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

  Last Listing Agent Gail Saucier BHHS Hudson Valley Properties
• 

  

  /50

  $525,000

  • 2 Beds
  • 1.5 Baths
  • 1,325 Sq Ft

  10 Dickman Farm Rd, Red Hook, NY 12571

  Beautifully renovated home privately set on a scenic, park-like property, offering the perfect blend of privacy and convenience—Located on the Dutchess/Columbia line just 2 minutes to the Taconic State Parkway for an easy commute. This move-in-ready home is filled with natural light and showcases high-end finishes, designer touches, and thoughtful updates throughout.The chef's kitchen

  Nicole Porter Houlihan Lawrence Inc.

  10 Dickman Farm Rd, Red Hook, NY 12571
• 

  $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 $545,395

  Last Listing Agent Thomas Zengen Thomas Zengen

  5 Myrtle Ave, Pine Plains, NY 12567
• 

  

  /30

  Est $492,045

  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

  Last Listing Agent Adam Ecker ECKER ADAM D
• 

  

  /38

  $300,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,446 Sq Ft

  18 Wicks Ave, Pine Plains, NY 12567

  Nestled on a peaceful corner lot spanning nearly an acre, this 4 bedroom 2 bath ranch offers the perfect blend of privacy, tranquility, and convenience. Located in a quiet, well-establish neighborhood, you’ll enjoy a serene setting while remaining just minutes from local restaurants, shops, and schools. The home features a spacious single-level layout with endless potential for those looking to

  Julie Roberts eXp Realty

  18 Wicks Ave, Pine Plains, NY 12567
• 

  

  /31

  $495,000

  Sold Jul 17, 2026

  367 Woods Ct, Ancramdale, NY 12503

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $397/SF
  • 55 Days On Market

  Current Estimated Value $529,004

  Last Listing Agent Paul Crayton Coldwell Banker Advisor Realty

  367 Woods Ct, Ancramdale, NY 12503
• 

  

  /33

  Est $435,757

  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

  Last Listing Agent Adam Ecker ECKER ADAM D
• 

  

  /30

  $415,000

  $24K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,091 Sq Ft

  75 Birch Dr, Pine Plains, NY 12567

  Beautiful, quiet neighborhood with park like setting. Lovely three-bedroom home with landscaped front, back and side yards. Spacious living room flows into quaint dining room with stained pine tongue & groove walls & updated country kitchen with backyard walkout access. Whether you're relaxing in front of the fireplace in the living room or entertaining friends at the backyard fire pit, you will

  Thomas Zengen Thomas Zengen

  75 Birch Dr, Pine Plains, NY 12567
• 

  $850,000

  Sold Aug 07, 2026

  608 Lake Rd, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 2,700 Sq Ft
  • Built 1955

  Last Sold Summary

  • $315/SF
  • 37 Days On Market

  Current Estimated Value $848,065

  Last Listing Agent ANN SIMMONS Compass Greater NY, LLC

  608 Lake Rd, Pine Plains, NY 12567
• 

  /2

  Est $1,895,724

  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

  Last Listing Agent Raj Kumar Four Seasons Sotheby's Int.
• 

  

  /14

  $495,000

  $30K PRICE DROP

  • 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 $727,677

  Last Listing Agent David Norman Hall Houlihan Lawrence Inc.

  60 County Route 7, Pine Plains, NY 12567
• 

  Est $421,660

  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

  Last Listing Agent Ernie Acampora River Realty Services, Inc.
• 

  

  /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 $845,734

  Last Listing Agent Jeffery Dolfinger Century 21 Hudson Valley Rlty.

  19 Friendship Ln, Red Hook, NY 12571
• 

  Est $319,156

  Not Listed For Sale

  Unlisted Address

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

  Unlisted Address

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Lorraine Little LITTLE LORRAINE ML
• 

  

  /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 $698,536

  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

  Last Listing Agent KEVIN HOWE BHHS Hudson Valley Properties
• 

  

  /50

  $9,500,000

  Pending

  • 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
• 

  $800,000

  Sold Jul 23, 2026

  303 Mt Ross Rd, Pine Plains, NY 12567

  • 3 Beds
  • 1.5 Baths
  • 2,028 Sq Ft
  • Built 1820

  Last Sold Summary

  • 10% Above List Price
  • $394/SF
  • 27 Days On Market

  Current Estimated Value $718,993

  Last Listing Agent Kyle Irwin Corcoran Country Living

  303 Mt Ross Rd, Pine Plains, NY 12567
• 

  

  /29

  Est $821,498

  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

  Last Listing Agent Sarah Finch The Kinderhook Group, Inc.

Showing Results 81 - 120, Page 3 of 18