Pine Plains Homes

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  $3,495,000

  • 4 Beds
  • 4 Baths
  • 4,103 Sq Ft

  476 Carpenter Hill Rd, Pine Plains, NY 12567

  Modern Minimalist Masterpiece on 19 Bucolic Acres in Dutchess County. Welcome to a rare offering in the heart of the Hudson Valley, where striking modern architecture meets timeless pastoral beauty. Completed in late 2024, this extraordinary estate sits on over 19 acres of flat, fenced farmland at the picturesque intersection of Bethel Cross and Carpenter Hill Road. Perfectly sited on a

  

  Rebecca Doh

  William Raveis Lifestyles Rlty

  (518) 594-8655

  476 Carpenter Hill Rd, Pine Plains, NY 12567
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  /50

  $2,610 per month

  Stissing Farms

  2 Beds

  51 Hillside Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and two car parking (one garage, one driveway)thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private

  51 Hillside Rd, Pine Plains, NY 12567
• 

  $732,000 Sold Oct 09, 2025

  546 Hicks Hill Rd, Stanfordville, NY 12581

  • 3 Beds
  • 2.5 Baths
  • 2,971 Sq Ft
  • Built 2003

  Last Sold Summary

  • $246/SF
  • 33 Days On Market

  Current Estimated Value $714,000

  Last Listing Agent Joseph Iannibelli Keller Williams NY Realty

  546 Hicks Hill Rd, Stanfordville, NY 12581
• 

  Est $1,718,038 Not Listed For Sale

  454 Bean River Rd, Pine Plains, NY 12567

  454 Bean River Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 9% Below List Price
  • 194 Days On Market

  Last Sold Price $1,895,000

  Last Listing Agent PAULA REDMOND Corcoran Country Living
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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

  (518) 676-2868

  0 Skunks Misery Rd Unit KEY860535, Pine Plains, NY 12546
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  $2,610 per month

  • 2 Beds
  • 2 Baths
  • 1,147 Sq Ft
  • Townhouse for Rent

  32 Town Centre Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  32 Town Centre Rd, Pine Plains, NY 12567
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  /12

  $55,000 Sold Oct 27, 2025

  0 County Route 8 Unit 20252154, Gallatin, NY 12567

  • Land
  • 1.1 Acres
  • $50,000 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 46 Days On Market

  Last Listing Agent Joel Craig Coldwell Banker Village Green

  0 County Route 8 Unit 20252154, Gallatin, NY 12567
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  /2

  Est $556,582 Not Listed For Sale

  7795 S Main St, Pine Plains, NY 12567

  • Studio
  • 4,032 Sq Ft
  • Built 1979

  7795 S Main St, Pine Plains, NY 12567

  Last Sold Summary

  • 14% Below List Price
  • $121/SF

  Last Sold Price $489,000

  Last Listing Agent Jo-Ann Campagiorni
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  /4

  $120,000

  • 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

  (518) 672-6676

  0 Mount Ross Rd, Pine Plains, NY 12567
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  $2,790 per month

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Townhouse for Rent

  53 Hillside Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  53 Hillside Rd, Pine Plains, NY 12567
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  $270,000 Sold Jan 08, 2026

  34 Myrtle Ave, Pine Plains, NY 12567

  • 5 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 1900

  Last Sold Summary

  • 7% Below List Price
  • $129/SF
  • 17 Days On Market

  Current Estimated Value $291,085

  Last Listing Agent Blake Michaud BHHS Hudson Valley Properties

  34 Myrtle Ave, Pine Plains, NY 12567
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  Not Listed For Sale

  7604 Route 82, Pine Plains, NY 12567

  • 5 Beds
  • 3.5 Baths
  • 3,712 Sq Ft
  • Built 1970

  7604 Route 82, Pine Plains, NY 12567

  Last Sold Summary

  • $131/SF
  • 346 Days On Market

  Last Sold Price $485,000

  Last Listing Agent MICHELLE FRANCESE Corcoran Country Living
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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

  (518) 765-1759

  317 Skunks Misery Rd, Millerton, NY 12546
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  $2,750 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Townhouse for Rent

  7 Hillside Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  7 Hillside Rd, Pine Plains, NY 12567
• 

  $810,000 Sold Apr 08, 2025

  2854 Church St, Pine Plains, NY 12567

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

  Last Sold Summary

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

  Current Estimated Value $820,579

  Last Listing Agent Diana Bisselle William Pitt Sothebys Int Rlty

  2854 Church St, Pine Plains, NY 12567
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  Est $362,362 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

  • 8% Above List Price
  • $258/SF
  • 53 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Christopher Virtuoso Keller Williams Realty HV Nort
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  $469,000

  • 3 Beds
  • 2 Baths
  • 1,298 Sq Ft

  30 Myrtle Ave, Pine Plains, NY 12567

  Welcome to the Historic Town of Pine Plains! This completely renovated three bedroom home on a quiet country road will delight and intrigue you. The home dates back to the early 1900's and some of the original characteristics have been left in tact. This is most assuredly Old World Charm meets Modern Convenience. One bedroom on the first floor attached to the Sunroom, will work for a great Flex

  Ellen Mallet

  30 Myrtle Ave, Pine Plains, NY 12567
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  /15

  $2,750 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Townhouse for Rent

  20 Town Centre Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  20 Town Centre Rd, Pine Plains, NY 12567
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  $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 $545,062

  Last Listing Agent Arleen Shepley Elyse Harney Real Estate

  30 N Main St, Pine Plains, NY 12567
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  Est $487,251 Not Listed For Sale

  3469 Route 199, Pine Plains, NY 12567

  • 3 Beds
  • 2.5 Baths
  • 2,272 Sq Ft
  • Built 1983

  3469 Route 199, Pine Plains, NY 12567

  Last Sold Summary

  • 39% Above List Price
  • $154/SF
  • 146 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Daniel Balassone VYLLA Home
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  /38

  $875,000

  • 4 Beds
  • 1.5 Baths
  • 2,709 Sq Ft

  7668 Route 82, Pine Plains, NY 12567

  Looking for a property that offers an opportunity for a homestead lifestyle in the Hudson Valley? Situated in the Town of Pine Plains, this early colonial farmhouse is now offered for sale on 15+ acres. Appointed with wide-plank floors, the main level features sun-lit, well-proportioned rooms. On the second floor, there is a primary bedroom with a dressing room, 3 additional bedrooms, an office,

  Susan Whalen George T Whalen Real Estate

  7668 Route 82, Pine Plains, NY 12567
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  /17

  $2,950 per month

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • House for Rent

  119 Righters Corners Rd, Pine Plains, NY 12567

  Welcome to 119 Righters Corners Rd, a charming and well-maintained two-bedroom, one-bathroom home located in the scenic Town of Pine Plains, New York. This inviting residence features hardwood floors throughout, creating a warm and cohesive living space. The kitchen and bathroom have been tastefully renovated, offering modern finishes while maintaining the home’s comfortable, classic feel. The

  Richard Brenner Rich Brenner Realty, LLC

  119 Righters Corners Rd, Pine Plains, NY 12567
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  $2,510,460 Sold Aug 06, 2025

  53 Brooks Rd, Pine Plains, NY 12567

  • 6 Beds
  • 5.5 Baths
  • 4,000 Sq Ft
  • Built 1850

  Last Sold Summary

  • 16% Below List Price
  • $628/SF
  • 300 Days On Market

  Last Listing Agent Anthony D'Argenzio Houlihan Lawrence, Inc

  53 Brooks Rd, Pine Plains, NY 12567
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  Est $722,297 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

  • 9% Above List Price
  • $220/SF
  • 49 Days On Market

  Last Sold Price $660,000

  Last Listing Agent Audrey Winslow Houlihan Lawrence, Inc.
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  /18

  $239,900

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

  16 Ryan Rd, Pine Plains, NY 12567

  Adorable 3-bedroom ranch ready for you to move in. Ideal for First-time home buyers or anyone tired of paying rent. Bright eat in kitchen, living room with fireplace. door that leads out to large back yard. Close to schools, Village of Pine Plains and TSP. County living at its best. Additional Information: HeatingFuel:Oil Above Ground,

  Joseph Lukic Compass Greater NY, LLC

  16 Ryan Rd, Pine Plains, NY 12567
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  /31

  $6,500 per month

  • 1 Bed
  • 1.5 Baths
  • 936 Sq Ft
  • House for Rent

  43 Lake Shore Dr, Pine Plains, NY 12567

  Welcome to The Lake Cottage – A Rare Seasonal Retreat on Twin Island LakeDiscover The Lake Cottage, a one-of-a-kind, fully furnished seasonal escape on the shores of Twin Island Lake. This private lakefront compound offers a tranquil and inspiring setting, making it the perfect getaway for artists, writers, creatives, or anyone in search of rest and renewal.Nestled behind lush, mature

  SHERI SCEROLER Four Seasons Sothebys Intl

  43 Lake Shore Dr, Pine Plains, NY 12567
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  $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 $535,173

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  43 Stissing Mountain Dr, Pine Plains, NY 12567
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  /2

  Est $466,605 Not Listed For Sale

  6 Sheldon Dr, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 1,310 Sq Ft
  • Built 2006

  6 Sheldon Dr, Pine Plains, NY 12567

  Last Sold Summary

  • 30% Below List Price
  • $275/SF

  Last Sold Price $360,000

  Last Listing Agent Larry Havens Havens Real Estate
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  /20

  $410,000

  • 3 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  73 Meusel Rd, Pine Plains, NY 12567

  A large and roomy home is for sale in the charming Village of Pine Plains, NY. Situated in a residential neighborhood with views of the surrounding hills, the home sits well back from the road on a corner lot. On the first floor are two living rooms, a dining room, an eat-in kitchen, a powder room and a mudroom. Off the kitchen is a partially finished three season room and a deck. Upstairs is the

  David Norman Hall Houlihan Lawrence, Inc

  73 Meusel Rd, Pine Plains, NY 12567
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  $307,500 Sold Mar 20, 2025

  3088 Church St, Pine Plains, NY 12567

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

  Last Sold Summary

  • 10% Below List Price
  • $132/SF
  • 43 Days On Market

  Current Estimated Value $334,544

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  3088 Church St, Pine Plains, NY 12567
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  Est $667,234 Not Listed For Sale

  2067 Route 83, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Built 1810

  2067 Route 83, Pine Plains, NY 12567

  Last Sold Summary

  • 16% Above List Price
  • $351/SF
  • 53 Days On Market

  Last Sold Price $575,000

  Last Listing Agent Kornelia Tamm BHHS Hudson Valley Properties
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  $4,495,000

  • 7 Beds
  • 4 Baths
  • 5,481 Sq Ft

  8032-8060 New York 82, Pine Plains, NY 12567

  Cedar Ridge Farm is a premier 246-acre equestrian estate set in the heart of Dutchess County, offering exceptional land quality, extensive infrastructure, and the rare scale required for a top tier equestrian operation or private country estate. The farm encompasses approximately 110 acres of fenced paddocks supported by thoughtfully designed facilities that ensure efficiency, functionality, and

  George Langa Houlihan Lawrence Inc.

  8032-8060 New York 82, Pine Plains, NY 12567
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  $135,000 Sold Jan 23, 2026

  58 Britton St, Pine Plains, NY 12567

  • Land
  • 0.93 Acre
  • $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
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  Est $264,763 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

  • 39% Below List Price
  • $134/SF
  • 52 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Brad Rebillard Dutchess Country Realty, Inc.
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  /31

  $549,000

  • Land
  • 43.69 Acres
  • $12,566 per Acre

  Tbd Hicks Hill Rd, Pine Plains, NY 12567

  Enjoy nature on your own 43 scenic acres located on Hicks Hill Road and additional access from Knob Hill Road, which is across from apprx 600 acres of protected land that can not be developed offering exceptional long term privacy. A versatile existing barn provides potential for a variety of uses. With over 1,400 feet of road frontage on Hicks Hill Road and electric available on the property,

  Jeannine Simmons Corcoran Country Living

  Tbd Hicks Hill Rd, Pine Plains, NY 12567
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  /40

  $8,350,000 Sold Jul 03, 2025

  25 Winchell Trail, Pine Plains, NY 12567

  • 5 Beds
  • 5 Baths
  • 5,935 Sq Ft
  • Built 2023

  Last Sold Summary

  • 15% Below List Price
  • $1,407/SF
  • 305 Days On Market

  Current Estimated Value $7,880,150

  Last Listing Agent Gary DiMauro Four Seasons Sotheby's Int.

  25 Winchell Trail, Pine Plains, NY 12567
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  Est $400,433 Not Listed For Sale

  3018 Church St, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft
  • Built 1875

  3018 Church St, Pine Plains, NY 12567

  Last Sold Summary

  • 27% Above List Price
  • $185/SF
  • 27 Days On Market

  Last Sold Price $315,000

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC
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  $139,000

  • Land
  • 4.6 Acres
  • $30,217 per Acre

  620 Bean River Rd, Pine Plains, NY 12567

  Great opportunity for 1 residence (property in Hamlet Zone, possibley subdividable) Approved septice design and existing shared driveway. Newly renovated home on adjoining lot. 8 acre lot on the other side also available for purchase. Owner will consider 3 year financing with substantial downpayment.

  David Birch Barns and Farms Realty LLC

  620 Bean River Rd, Pine Plains, NY 12567
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  /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
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  Est $488,284 Not Listed For Sale

  17 Smith St, Pine Plains, NY 12567

  • 6 Beds
  • 2,550 Sq Ft
  • Built 1952

  17 Smith St, Pine Plains, NY 12567

  Last Sold Summary

  • 15% Above List Price
  • $167/SF
  • 88 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Thomas Zengen Thomas Zengen

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