Pine Plains, NY Homes

• 

  $1,470,000

  Sold Jul 23, 2026

  1598 Jackson Corners Rd, Red Hook, NY 12571

  • 5 Beds
  • 3.5 Baths
  • 4,176 Sq Ft
  • Built 1790

  Last Sold Summary

  • 13% Below List Price
  • $352/SF
  • 372 Days On Market

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  1598 Jackson Corners Rd, Red Hook, NY 12571
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  /4

  Not Listed For Sale

  0 Hill Top Rd Unit 155018, Gallatin, NY 12502

  0 Hill Top Rd Unit 155018, Gallatin, NY 12502

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Andrew Gates Houlihan Lawrence, Inc.
• 

  

  

  /11

  $325,000

  • Land
  • 24.9 Acres
  • $13,052 per Acre

  0 Hall Hill Rd Unit KEY998490, Ancram, NY 12502

  Privately tucked away along one of Ancram’s most picturesque country roads, this beautiful approximately 25-acre offering presents a rare opportunity to create a secluded full-time residence or weekend retreat in the heart of the Hudson Valley. Quiet and rural, yet conveniently located just 8 minutes to Pine Plains, 15 minutes to Millerton and Copake, and under 30 minutes to Hudson, Red Hook, and

  Ann Stettner Neil Charles Real Estate, LLC

  0 Hall Hill Rd Unit KEY998490, Ancram, NY 12502
• 

  $520,000

  Sold Dec 30, 2025

  30 N Main St, Pine Plains, NY 12567

  • 4 Beds
  • 2.5 Baths
  • 3,180 Sq Ft
  • Built 1880

  Last Sold Summary

  • 13% Below List Price
  • $164/SF
  • 99 Days On Market

  Current Estimated Value $549,158

  Last Listing Agent Arleen Shepley Elyse Harney Real Estate

  30 N Main St, Pine Plains, NY 12567
• 

  Est $2,508,084

  Not Listed For Sale

  420 Carpenter Hill Rd, Pine Plains, NY 12567

  • 6 Beds
  • 4.5 Baths
  • 5,163 Sq Ft
  • Built 1996

  420 Carpenter Hill Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 162 Days On Market

  Last Listing Agent LINDSAY BALDWIN Houlihan Lawrence Inc.
• 

  

  /43

  $1,250,000

  • 5 Beds
  • 3 Baths
  • 2,482 Sq Ft

  303 Hicks Hill Rd, Stanfordville, NY 12581

  Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming

  HOMER STALEY JR. Staley Real Estate, LLC

  303 Hicks Hill Rd, Stanfordville, NY 12581
• 

  $515,000

  Sold Oct 27, 2025

  43 Stissing Mountain Dr, Pine Plains, NY 12567

  • 3 Beds
  • 1.5 Baths
  • 1,862 Sq Ft
  • Built 1983

  Last Sold Summary

  • 21% Below List Price
  • $277/SF
  • 93 Days On Market

  Current Estimated Value $597,457

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  43 Stissing Mountain Dr, Pine Plains, NY 12567
• 

  Est $1,283,303

  Not Listed For Sale

  140 Mountain Rd, Stanfordville, NY 12581

  • 3 Beds
  • 3 Baths
  • 2,568 Sq Ft
  • Built 1984

  140 Mountain Rd, Stanfordville, NY 12581

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Elyse Morris Elyse Harney Real Estate
• 

  

  /14

  $220,000

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  16 Ryan Rd, Pine Plains, NY 12567

  Welcome to 16 Ryan Road, a spacious 3-bedroom, 2-bathroom home in the scenic Pine Plains area. Featuring a large kitchen with plenty of workspace, a center island, and a functional layout with generous living areas, this home offers a great foundation for your next project.The property needs some updating and is ideal for a buyer looking to add their own personal touches and build equity.

  Jasper Newman Charles Rutenberg Realty Inc

  16 Ryan Rd, Pine Plains, NY 12567
• 

  $595,000

  Sold Feb 19, 2026

  100 Knob Hill Rd, Stanfordville, NY 12581

  • 3 Beds
  • 1.5 Baths
  • 1,725 Sq Ft
  • Built 1965

  Last Sold Summary

  • 3% Above List Price
  • $345/SF
  • 27 Days On Market

  Current Estimated Value $603,624

  Last Listing Agent Kimberly Wickes R. Ferris Real Estate, LLC

  100 Knob Hill Rd, Stanfordville, NY 12581
• 

  

  /33

  Est $801,575

  Not Listed For Sale

  218 Mountain Rd, Stanfordville, NY 12581

  • 3 Beds
  • 2.5 Baths
  • 2,486 Sq Ft
  • Built 2002

  218 Mountain Rd, Stanfordville, NY 12581

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent Savannah Miceli Century 21 Alliance-NP
• 

  

  /49

  $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
• 

  $350,000

  Sold Dec 31, 2025

  0 New York 82 Unit KEYM420064, Stanfordville, NY 12581

  • Land
  • 5.02 Acres
  • $69,721 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 725 Days On Market

  Last Listing Agent Steve Bruman Corcoran Country Living

  0 New York 82 Unit KEYM420064, Stanfordville, NY 12581
• 

  

  /3

  Est $368,628

  Not Listed For Sale

  599 Bean River Rd, Millerton, NY 12546

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1950

  599 Bean River Rd, Millerton, NY 12546

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Christopher Virtuoso Keller Williams Realty HV Nort
• 

  

  /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
• 

  $135,000

  Sold Jan 23, 2026

  58 Britton St, Pine Plains, NY 12567

  • Land
  • 40,510 Sq Ft
  • $145,161 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 94 Days On Market

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  58 Britton St, Pine Plains, NY 12567
• 

  

  /43

  Est $663,471

  Not Listed For Sale

  3327 Route 199, Pine Plains, NY 12567

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • Built 1787

  3327 Route 199, Pine Plains, NY 12567

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Audrey Winslow Houlihan Lawrence Inc.
• 

  

  /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
• 

  $165,000

  Sold May 08, 2026

  22-28 Ryan Rd, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Built 1972

  Last Sold Summary

  • 38% Below List Price
  • $159/SF
  • 122 Days On Market

  Last Listing Agent Jorge Lugo Real Broker NY LLC

  22-28 Ryan Rd, Pine Plains, NY 12567
• 

  Est $358,055

  Not Listed For Sale

  3088 Church St, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 2,328 Sq Ft
  • Built 1872

  3088 Church St, Pine Plains, NY 12567

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC
• 

  

  /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
• 

  /2

  $2,600,000

  Sold Jul 17, 2026

  3778 New York 82, Ancramdale, NY 12503

  • 3 Beds
  • 3.5 Baths
  • 4,247 Sq Ft
  • Built 1991

  Last Sold Summary

  • $612/SF
  • 23 Days On Market

  Last Listing Agent Michael Stasi Corcoran Country Living

  3778 New York 82, Ancramdale, NY 12503
• 

  

  /16

  Est $336,667

  Not Listed For Sale

  3066 Church St, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • Built 1870

  3066 Church St, Pine Plains, NY 12567

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Brad Rebillard Past Member
• 

  

  /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
• 

  $100,000

  Sold Sep 10, 2025

  1691 Jackson Corners Rd, Red Hook, NY 12571

  • 2 Beds
  • 1.5 Baths
  • 984 Sq Ft
  • Built 1970

  Last Sold Summary

  • 47% Below List Price
  • $102/SF
  • 79 Days On Market

  Last Listing Agent Catherine Mondello Mondello Upstate Properties

  1691 Jackson Corners Rd, Red Hook, NY 12571
• 

  

  /7

  Est $199,372

  Not Listed For Sale

  10 Academy St, Pine Plains, NY 12567

  • 2 Beds
  • 1 Bath
  • 1,153 Sq Ft
  • Built 1870

  10 Academy St, Pine Plains, NY 12567

  Last Sold Summary

  • 118 Days On Market

  Last Listing Agent Libby McKee Berkshire Hathaway HomeService
• 

  

  /6

  $107,750

  Under Contract

  • 3 Beds
  • 1 Bath
  • 800 Sq Ft

  7 Woodside St, Pine Plains, NY 12567

  Set on approximately .53 acres in a desirable Pine Plains neighborhood, this three-bedroom, one-bath mobile home offers an excellent opportunity for those looking to bring their vision and creativity to a property with potential. The home is in need of some TLC and is ready for renovation, updating, and thoughtful improvements to restore its appeal and make it shine once again. With a convenient

  Arleen Shepley Elyse Harney Real Estate

  7 Woodside St, Pine Plains, NY 12567
• 

  

  /11

  $185,000

  Sold Nov 01, 2025

  00-1 New York 82, Pine Plains, NY 12567

  • Land
  • 20 Acres
  • $9,250 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 22 Days On Market

  Last Listing Agent Jeffries Blackerby Houlihan Lawrence Inc.

  00-1 New York 82, Pine Plains, NY 12567
• 

  Est $598,864

  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

  Last Listing Agent CHRISTINE BATES William Pitt Sotheby's Int'l
• 

  

  /14

  $495,000

  $30K PRICE DROP

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

  284 Hall Hill Rd Unit Stop 18, 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 Unit Stop 18, Ancram, NY 12502
• 

  

  /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 $257,218

  Last Listing Agent David Norman Hall Houlihan Lawrence Inc.

  721 County Route 7, Pine Plains, NY 12567
• 

  Est $810,271

  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

  Last Listing Agent Diana Bisselle William Pitt Sothebys Int Rlty
• 

  

  /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
• 

  $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
• 

  

  /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
• 

  

  /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
• 

  $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 $1,118,147

  Last Listing Agent Dan Kessler Compass Greater NY, LLC

  390 Carpenter Hill Rd, Pine Plains, NY 12567
• 

  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
• 

  

  /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
• 

  $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

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