Pine Plains Homes

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  /8

  $975,000

  • Land
  • 37,026 Sq Ft
  • $1,147,059 per Acre

  71 Lake Shore Dr, Pine Plains, NY 12567

  The Ultimate Hudson Valley Lakefront Package: Waterfront Mainland Barn, Private Island Glamping Airbnb, Ease Side Lake Access Land & Endless Views!Welcome to a truly unprecedented real estate opportunity on the pristine waters of Twin Island Lake in beautiful Pine Plains, NY. This isn’t just a land listing; it is an extraordinary three-parcel package deal that blends rustic charm, income

  KELLY ROMANO Keller Williams Realty

  71 Lake Shore Dr, Pine Plains, NY 12567
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• 

  $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 $581,865

  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

  • 19 Days On Market
• 

  

  

  /7

  $139,000

  • Land
  • 4.24 Acres
  • $32,783 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 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 $808,704

  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

  • 61 Days On Market
• 

  

  /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
• 

  $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
• 

  

  /31

  Est $814,262

  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
• 

  

  /16

  $549,000

  Open Sat 1PM - 4PM

  • 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 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 $405,936

  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
• 

  

  /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
• 

  $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 $349,886

  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
• 

  

  /15

  $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 FEATURES A LIVINGROOM WITH A FIREPLACE, LOVELY WOOD FLOORS THROUGHOUT AND A LARGE BASEMENT PERFECT FOR A WORKSHOP, RECREATION ROOM OR ADDITIONAL STORAGE. THE ATTACHED GARAGE

  ANN SIMMONS Compass Greater NY, LLC

  60 Stissing Ave, 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
• 

  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
• 

  

  /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
• 

  $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 $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
• 

  

  /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
• 

  $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 $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
• 

  

  /18

  $639,000

  Open Sat 1PM - 4PM

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

  553 Lake Rd, Pine Plains, NY 12567

  COMING SOON: 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

  KELLY ROMANO Keller Williams Realty

  553 Lake Rd, 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 $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
• 

  

  /42

  $725,000

  • 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
• 

  $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 $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
• 

  

  /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
• 

  $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 $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
• 

  

  /16

  $179,000

  $51K PRICE DROP Pending

  • 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
• 

  

  /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
• 

  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
• 

  

  /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
• 

  $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
• 

  Est $398,015

  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

  • 61 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

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