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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  $2,760 - $2,940 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
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  $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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  Est $1,677,672 Not Listed For Sale

  454 Bean River Rd, Pine Plains, NY 12567

  454 Bean River Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 11% Below List Price
  • 194 Days On Market

  • Last Sold Price $1,895,000
  • Dec 18, 2023

  Last Listing Agent PAULA REDMOND Corcoran Country Living
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  $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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  /15

  $2,850 per month

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

  59 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

  59 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 $280,362

  Last Listing Agent Blake Michaud BHHS Hudson Valley Properties

  34 Myrtle Ave, Pine Plains, NY 12567
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  Est $557,568 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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  $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
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  $12,000 per month

  • 4 Beds
  • 4 Baths
  • 3,029 Sq Ft
  • House for Rent

  231 Lake Rd, Pine Plains, NY 12567

  Ideal Summer Retreat. This 4 bedroom (all ensuite), is a perfect blend of chic furnishings and modern conveniences, located in a quiet lakeside community in the heart of Pine Plains but also removed and private. A stones-throw away from Stissing Pond, where you can swim, launch SUP’s and go fishing for trophy Bass, or take a leisurely bike ride around the lake, 3-5 mile loop (local traffic

  CATHERINE HOWARD Corcoran Country Living

  231 Lake Rd, Pine Plains, NY 12567
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  $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 $734,342

  Last Listing Agent Joseph Iannibelli Keller Williams NY Realty

  546 Hicks Hill Rd, Stanfordville, NY 12581
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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
  • Jun 02, 2023

  Last Listing Agent MICHELLE FRANCESE Corcoran Country Living
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  $399,000

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  3838 Route 199, Pine Plains, NY 12567

  Sweet and solid, one level Ranch home on a bucolic setting with rolling hills and farmland framing your homestead. Walk into your open living room with built ins and lovely bay window. Through to the dining room and eat in kitchen, perfect for hosting with ease. Sliders to the back covered porch off the dining room allows for al fresco living and enjoying your coffee while watching the sunrise.

  Chelsea Pollard-Seiler Mondello Upstate Properties

  3838 Route 199, Pine Plains, NY 12567
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  /17

  $2,250 per month

  • 2 Beds
  • 1 Bath
  • 594 Sq Ft
  • House for Rent

  3004 W Church St Unit Cottage, Pine Plains, NY 12567

  Fully renovated two-bedroom cottage in the hamlet of Pine Plains, offering the convenience of in-town living just steps from the center of this charming Hudson Valley community. The home features a bright, welcoming interior with an updated kitchen and bath, two well-proportioned bedrooms, and the convenience of an in-home washer and dryer. Modern updates throughout blend cottage charm with

  Jennifer Enloe Four Seasons Sotheby's Int.

  3004 W Church St Unit Cottage, 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 $538,323

  Last Listing Agent Arleen Shepley Elyse Harney Real Estate

  30 N Main St, Pine Plains, NY 12567
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  Est $3,020,699 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

  • 12% Below List Price
  • $663/SF
  • 162 Days On Market

  • Last Sold Price $3,425,000
  • Apr 16, 2025

  Last Listing Agent LINDSAY BALDWIN Houlihan Lawrence Inc.
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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, and the Pine Plains School District! 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

  Ellen Mallet

  30 Myrtle Ave, Pine Plains, NY 12567
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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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  $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 $365,520 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

  • 9% Above List Price
  • $258/SF
  • 53 Days On Market

  • Last Sold Price $335,000
  • Jan 30, 2025

  Last Listing Agent Christopher Virtuoso Keller Williams Realty HV Nort
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  $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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  $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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  $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 $543,930

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  43 Stissing Mountain Dr, Pine Plains, NY 12567
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  Est $773,712 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

  • 17% Above List Price
  • $220/SF
  • 49 Days On Market

  • Last Sold Price $660,000
  • Aug 09, 2024

  Last Listing Agent Audrey Winslow Houlihan Lawrence Inc.
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  $389,000

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft

  618 Bean River Rd, Pine Plains, NY 12567

  Secluded 2BR/2BA RANCH w/2 large decks, all wood floors, ornamented wood siding painted + detached 2 car garage on 7 acres. Parcel is subdividable in Hamlet zone. New well installed.also available with 8 additional acres for 564000 with additional 4 acres for 664000

  David Birch Barns & Farms Realty, LLC

  618 Bean River Rd, Pine Plains, NY 12567
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  $2,850 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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  $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
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  Est $650,941 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

  • 13% Above List Price
  • $351/SF
  • 53 Days On Market

  • Last Sold Price $575,000
  • Jul 31, 2023

  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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  $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 $6,166,594

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

  25 Winchell Trail, Pine Plains, NY 12567
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  Est $338,123 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

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

  • Last Sold Price $307,500
  • Mar 20, 2025

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC
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  $549,000 Under Contract

  • 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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  $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 $293,987 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

  • 55% Below List Price
  • $134/SF
  • 52 Days On Market

  • Last Sold Price $190,000
  • Jan 13, 2025

  Last Listing Agent Brad Rebillard Past Member
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  $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
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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
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  Est $219,664 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

  • 69% Above List Price
  • $113/SF
  • 118 Days On Market

  • Last Sold Price $130,000
  • Apr 04, 2025

  Last Listing Agent Libby McKee Berkshire Hathaway HomeService
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  $485,000

  • 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
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  $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 $1,096,694

  Last Listing Agent Dan Kessler Compass Greater NY, LLC

  390 Carpenter Hill Rd, Pine Plains, NY 12567
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  Est $462,156 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

  • 9% Above List Price
  • $167/SF
  • 88 Days On Market

  • Last Sold Price $425,000
  • May 16, 2023

  Last Listing Agent Thomas Zengen Thomas Zengen

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