Pine Plains Homes

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  $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
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• 

  $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 $570,704

  Last Listing Agent Rita Longo Howard Hanna Rand Realty

  540 Hicks Hill Rd, Stanfordville, NY 12581
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  Est $596,086 Not Listed For Sale

  7760 S Main St, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 1,643 Sq Ft
  • Built 1960

  7760 S Main St, Pine Plains, NY 12567

  Last Sold Summary

  • 1% Above List Price
  • $359/SF
  • 19 Days On Market

  • Last Sold Price $590,000
  • Nov 15, 2024

  Last Listing Agent CHRISTINE BATES William Pitt
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  /21

  $255,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,037 Sq Ft

  22-28 Ryan Rd, Pine Plains, NY 12567

  Looking for a piece of property for a great low price? Looking for two homes for the price of one? Looking for a good-sized plot of land? Here is a great opportunity for you to acquire one manufactured home, and one mobile home, both on the same plot of land with 2.30 acres! Investors will consider this property for rental income or tear-down and rebuild. Currently, the main manufactured home has

  Jorge Lugo Real Broker NY LLC

  22-28 Ryan 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 $843,939

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  2365 Route 83, Pine Plains, NY 12567
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  Est $825,298 Not Listed For Sale

  2854 Church St, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 2,208 Sq Ft
  • Built 1911

  2854 Church St, Pine Plains, NY 12567

  Last Sold Summary

  • 2% Above List Price
  • $367/SF
  • 61 Days On Market

  • Last Sold Price $810,000
  • Apr 08, 2025

  Last Listing Agent Diana Bisselle William Pitt Sothebys Int Rlty
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  /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 $564,000 and additional 4 acre boha parcel for $664,000. Adjoining parcels can be purchased separately. Great location between Pine Plains Village and Millerton on quiet road

  David Birch Barns and Farms Realty LLC

  618 Bean River Rd, Millerton, NY 12546
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  $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 $305,253

  Last Listing Agent Theodore Weinstein REO Edge LLC

  6 Carla Terrace, Pine Plains, NY 12567
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  /31

  Est $744,586 Not Listed For Sale

  43 Lake Shore Dr, Pine Plains, NY 12567

  • 1 Bed
  • 0.5 Baths
  • 936 Sq Ft
  • Built 1960

  43 Lake Shore Dr, Pine Plains, NY 12567

  Last Sold Summary

  • 1% Below List Price
  • $802/SF
  • 155 Days On Market

  • Last Sold Price $751,000
  • Dec 21, 2023

  Last Listing Agent Jennifer Capala William Pitt Sothebys Intn'l
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  $120,000 Pending

  • 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

  0 Mount Ross Rd, Pine Plains, NY 12567
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  $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 $522,138

  Last Listing Agent Thomas Zengen Thomas Zengen

  5 Myrtle Ave, Pine Plains, NY 12567
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  Est $483,092 Not Listed For Sale

  35 Pine St, Pine Plains, NY 12567

  • 4 Beds
  • 2 Baths
  • 2,884 Sq Ft
  • Built 1890

  35 Pine St, Pine Plains, NY 12567

  Last Sold Summary

  • 35% Above List Price
  • $124/SF
  • 46 Days On Market

  • Last Sold Price $357,000
  • Nov 10, 2023

  Last Listing Agent Sean Eidle BHHS Hudson Valley Properties
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  /16

  $179,000

  • Land
  • 19.4 Acres
  • $9,227 per Acre

  A Skunks Misery Rd, Millerton, NY 12546

  Stunning 19.4 Acres – Estate Setting on a Premier Country Road Discover the perfect blend of natural beauty and refined location with this 19.4-acre parcel situated on a picturesque country road, renowned for its stately homes and rural charm. With multiple elevated building sites, long road frontage, and sweeping view potential, this property offers endless opportunities. Explore its trout

  Robert Dunlop Havens Real Estate

  A Skunks Misery Rd, Millerton, NY 12546
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  $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 $720,970

  Last Listing Agent Larry Havens Havens Real Estate

  115-133 Mount Ross Rd, Pine Plains, NY 12567
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  Est $347,487 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

  • 1% Above List Price
  • $302/SF
  • 89 Days On Market

  • Last Sold Price $345,000
  • Oct 08, 2024

  Last Listing Agent Andrea Replansky BHHS Hudson Valley Properties
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  /27

  $174,800

  • 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
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  $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 $527,209

  Last Listing Agent Catherine Mondello Mondello Upstate Properties

  143 Ryan Rd, Pine Plains, NY 12567
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  Est $512,237 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

  • 15% Above List Price
  • $148/SF
  • 44 Days On Market

  • Last Sold Price $445,000
  • Aug 22, 2023

  Last Listing Agent Diane Zani BHHS Hudson Valley Properties
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  /16

  $3,600,000

  • Land
  • 228.91 Acres
  • $15,727 per Acre

  317 Skunks Misery Rd, Millerton, NY 12546

  Public Remarks: One of the most breathtaking vistas in the region, this 157-acre parcel crowns a private site at 1,250 feet, with commanding views to the Catskills. Offered for the first time in generations, this legacy property is paired with an adjacent 71.5-acre parcel, once a distinguished family farm. The panoramic vista from every knoll enjoys the unspoiled countryside extending to the

  Larry Havens Havens Real Estate

  317 Skunks Misery Rd, Millerton, NY 12546
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  $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 $284,029

  Last Listing Agent Susan Whalen George T Whalen Real Estate

  46 Myrtle Ave, Pine Plains, NY 12567
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  Est $375,916 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

  • 11% Above List Price
  • $193/SF
  • 115 Days On Market

  • Last Sold Price $339,200
  • Nov 04, 2024

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC
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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

  0 Skunks Misery Rd Unit KEY860535, Pine Plains, NY 12546
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  $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 $353,808

  Last Listing Agent Janet Myer Houlihan Lawrence Inc.

  3807 Route 199, Pine Plains, NY 12567
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  Est $446,429 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

  • 8% Above List Price
  • $207/SF
  • 123 Days On Market

  • Last Sold Price $415,000
  • Jun 20, 2024

  Last Listing Agent Melissa Pettinella Century 21 Alliance Realty Grp
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  $199,000

  • Land
  • 8.59 Acres
  • $23,166 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
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  $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 $369,002

  Last Listing Agent Brad Rebillard DUTCHESS COUNTRY REALTY INC. M

  48 Woodside St, Pine Plains, NY 12567
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  Est $416,029 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

  • 11% Above List Price
  • $230/SF
  • 14 Days On Market

  • Last Sold Price $375,000
  • Dec 20, 2023

  Last Listing Agent Catherine Mondello Mondello Upstate Properties
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  $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
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  Est $404,033 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

  • 46% Above List Price
  • $92/SF
  • 54 Days On Market

  • Last Sold Price $277,000
  • Jul 31, 2023

  Last Listing Agent AARON VIGNOGNA Century 21 Alliance Rlty Group
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  $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 $298,333

  Last Listing Agent Michael Cahill HomeSmart Homes & Estates

  4 Antler Club Rd, Pine Plains, NY 12567
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  Est $376,650 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

  • 30% Above List Price
  • $171/SF
  • 53 Days On Market

  • Last Sold Price $290,000
  • Jul 30, 2024

  Last Listing Agent Shannon Martin BHHS Hudson Valley Properties
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  Est $502,626 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

  • 82% Above List Price
  • $129/SF
  • 35 Days On Market

  • Last Sold Price $275,888
  • Dec 22, 2023

  Last Listing Agent Gail Saucier BHHS Hudson Valley Properties
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  Est $436,019 Not Listed For Sale

  18 Bfs Ln, Pine Plains, NY 12567

  • 3 Beds
  • 1 Bath
  • 2,860 Sq Ft
  • Built 1951

  18 Bfs Ln, Pine Plains, NY 12567

  Last Sold Summary

  • 62% Above List Price
  • $94/SF
  • 61 Days On Market

  • Last Sold Price $269,000
  • Jun 15, 2023

  Last Listing Agent Thomas Zengen Thomas Zengen
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  /30

  Est $473,674 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

  • $380/SF
  • 19 Days On Market

  • Last Sold Price $475,000
  • Oct 01, 2024

  Last Listing Agent Adam Ecker ECKER ADAM D
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  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

  • $233/SF
  • 18 Days On Market

  • Last Sold Price $107,000
  • Oct 30, 2024

  Last Listing Agent Terese Mondello Mondello Upstate Properties
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  Not Listed For Sale

  3362 New York 199, Pine Plains, NY 12567

  3362 New York 199, Pine Plains, NY 12567

  Last Sold Summary

  • 87 Days On Market

  • Last Sold Price $250,000
  • Dec 16, 2024

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC
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  /16

  Not Listed For Sale

  00WP Hoffman Rd, Pine Plains, NY 12567

  00WP Hoffman Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 133 Days On Market

  • Last Sold Price $62,000
  • Nov 21, 2024

  Last Listing Agent Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)
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  Est $414,508 Not Listed For Sale

  23 Willow St, Pine Plains, NY 12567

  • 2 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 2010

  23 Willow St, Pine Plains, NY 12567

  Last Sold Summary

  • 14% Above List Price
  • $194/SF
  • 154 Days On Market

  • Last Sold Price $362,500
  • Nov 01, 2024

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC
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  Not Listed For Sale

  639 Bean River Rd, Pine Plains, NY 12547

  639 Bean River Rd, Pine Plains, NY 12547

  Last Sold Summary

  • 183 Days On Market

  • Last Sold Price $101,000
  • May 30, 2023

  Last Listing Agent Michael Tellerday Houlihan Lawrence Inc.
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  Est $714,023 Not Listed For Sale

  17 Hammertown Rd, Pine Plains, NY 12567

  • 3 Beds
  • 3 Baths
  • 2,898 Sq Ft
  • Built 2010

  17 Hammertown Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 59% Above List Price
  • $155/SF
  • 95 Days On Market

  • Last Sold Price $450,000
  • Jun 09, 2023

  Last Listing Agent Howard Payson RE/MAX

Showing Results 41 - 80, Page 2 of 18