Pine Plains Homes

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  /31

  Est $824,079

  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

  • 155 Days On Market

  Last Listing Agent Jennifer Capala William Pitt Sothebys Intn'l
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  /32

  $395,000

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft

  31 Lake Shore Dr, Pine Plains, NY 12567

  Here is a truly exceptional opportunity to enjoy the peaceful lifestyle that comes with lakefront living. Immerse in the sounds of nature, enjoy the changing seasons, spend warm summer days kayaking on the lake, and relax in a setting that feels like a true departure from the everyday. Welcome to your sweet escape at 31 Lake Shore Drive, a charming cottage with an open floor plan and vaulted

  Roadman Etienne BHHS Hudson Valley Properties

  31 Lake Shore Dr, 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 $430,009

  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

  • 46 Days On Market

  Last Listing Agent Sean Eidle BHHS Hudson Valley Properties
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  /7

  $138,000

  $1K PRICE DROP

  • Land
  • 4.24 Acres
  • $32,547 per Acre

  620 Bean River Rd, Pine Plains, NY 12567

  Great opportunity for 1 residence (property is in Hamlet Zone and possibly subdividable). Approved Septic design and existing shared driveway (probably 10 feed are shared). Newly renovated home on North. Adjoining 8 acre vacant lot to the South available for 199,000. Both lots for 300,000. Owner financing possible.

  David Birch Barns & Farms Realty, LLC

  620 Bean River 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 $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
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  /72

  $1,975,000

  $500K PRICE DROP

  • 7 Beds
  • 6 Baths
  • 4,675 Sq Ft

  85 Hammertown Rd, Pine Plains, NY 12567

  The History:The wonderfully characterful Hammertown was established in 1774, in a small hamlet of millworkers, farmers, and blacksmiths, amidst the lush pastoral landscapes surrounding what would become the town of Pine Plains, New York. The home and its grounds were occupied by only three families across 250 years, each family slowly developing the property to include, in addition to the

  Raj Kumar Four Seasons Sotheby's Int.

  85 Hammertown 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 $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
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  /38

  $485,000

  $4K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  82 Lake Rd, Pine Plains, NY 12567

  A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite

  MICHELLE FRANCESE Corcoran Country Living

  82 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 $545,395

  Last Listing Agent Thomas Zengen Thomas Zengen

  5 Myrtle Ave, 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
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  /50

  $549,000

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  559 Lake Rd, Pine Plains, NY 12567

  Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has a proven track record as a highly successful Airbnb. Whether you are looking for a lucrative investment, a dream summer getaway, or a year-round sanctuary, this home has it all. The entire front of the house features stunning, unobstructed lake views. Start your mornings on

  KELLY ROMANO Keller Williams Realty

  559 Lake Rd, 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
• 

  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
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  /8

  $345,000

  • Land
  • 68.33 Acres
  • $5,049 per Acre

  000 New York 82, Pine Plains, NY 12567

  This beautiful, gently sloping parcel offers the perfect canvas to create your country escape or full-time residence on 68+ private acres. Soil tests complete for two building sites. Some clearing would offer ridgeline views to the south and west. Roughed-in driveway is in place, so you're well on your way to building a home that's tailored exactly to your needs. Just 20 minutes to Hudson and Red

  Jeffries Blackerby Houlihan Lawrence Inc.

  000 New York 82, Pine Plains, NY 12567
• 

  $160,000

  Sold Jun 11, 2026

  A Skunks Misery Rd, Millerton, NY 12546

  • Land
  • 19.4 Acres
  • $8,247 per Acre

  Last Sold Summary

  • 30% Below List Price
  • 285 Days On Market

  Last Listing Agent Robert Dunlop Havens Real Estate

  A Skunks Misery Rd, Millerton, NY 12546
• 

  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
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  /40

  $1,495,000

  $80K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,833 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 Sothebys Int Rlty

  617 Bean River 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
• 

  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
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  /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
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  /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
• 

  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
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  /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
• 

  $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
• 

  

  /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
• 

  

  /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
• 

  $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
• 

  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
• 

  

  /17

  $1,450,000

  • Land
  • 106.43 Acres
  • $13,624 per Acre

  0 Skunks Misery Rd Unit 20264594, Pine Plains, NY 12546

  A Sportsman's Paradise - Hunt, Fish, and Explore in Nature's EmbraceEscape to a breathtaking retreat tucked along a peaceful country lane, offering the perfect sanctuary for outdoor enthusiasts and nature lovers. This remarkable estate features rolling meadows, lush pastures, and towering woodlands, all centered around a picturesque pond. Whether you're seeking a private getaway or an estate to

  Larry Havens Havens Real Estate

  0 Skunks Misery Rd Unit 20264594, Pine Plains, NY 12546
• 

  $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
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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

  • 18 Days On Market

  Last Listing Agent Terese 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
• 

  $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
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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 Listing Agent Richard Brenner Rich Brenner Realty, LLC
• 

  

  /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
• 

  $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
• 

  

  /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 Listing Agent Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

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