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

  Live the way you've always wanted without compromising style or quality. At Stissing Farm Townhomes, our apartment residences are designed with you in mind. Now you really can have it all . . . lifestyle included.Pine Plains was named One of the Best Small Towns in New York by !

  51 Hillside 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 $726,387

  Last Listing Agent Joseph Iannibelli Keller Williams NY Realty

  546 Hicks Hill Rd, Stanfordville, NY 12581
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  Est $237,593 Not Listed For Sale

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

  3066 Church St, Pine Plains, NY 12567

  3066 Church St, Pine Plains, NY 12567
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  $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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  $2,950 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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  $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 $1,691,095 Not Listed For Sale

  454 Bean River Rd, Pine Plains, NY 12567

  454 Bean River Rd, Pine Plains, NY 12567
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  $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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  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  2704 Ny-199 Unit Apartment for rent, Pine Plains, NY 12567

  3 Bedrooms-2 bathroom - Full kitchen and huge dining area- Living room - Utilities include heating, hot water, electric- Free parking in the lot- Brand new renovations including new flooring, new windows, new insulation.

  2704 Ny-199 Unit Apartment for rent, 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

  Last Listing Agent Blake Michaud Serhant LLC

  34 Myrtle Ave, Pine Plains, NY 12567
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  Est $557,501 Not Listed For Sale

  • Studio
  • 4,032 Sq Ft

  7795 S Main St, Pine Plains, NY 12567

  7795 S Main St, Pine Plains, NY 12567
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  $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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  $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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  $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 $829,108

  Last Listing Agent Diana Bisselle William Pitt Sothebys Int Rlty

  2854 Church St, Pine Plains, NY 12567
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  Not Listed For Sale

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

  7604 Route 82, Pine Plains, NY 12567

  7604 Route 82, Pine Plains, NY 12567
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  $490,000

  • 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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  $335,000 Sold Jan 30, 2025

  599 Bean River Rd, Millerton, NY 12546

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

  Last Sold Summary

  • 4% Below List Price
  • $258/SF
  • 53 Days On Market

  Current Estimated Value $373,675

  Last Listing Agent Christopher Virtuoso Keller Williams Realty HV Nort

  599 Bean River Rd, Millerton, NY 12546
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  Est $554,769 Not Listed For Sale

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

  3469 Route 199, Pine Plains, NY 12567

  3469 Route 199, Pine Plains, NY 12567
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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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  $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

  Last Listing Agent Arleen Shepley Elyse Harney Real Estate

  30 N Main St, Pine Plains, NY 12567
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  Est $744,203 Not Listed For Sale

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

  3327 Route 199, Pine Plains, NY 12567

  3327 Route 199, Pine Plains, NY 12567
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  $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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  $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 $454,177 Not Listed For Sale

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

  6 Sheldon Dr, Pine Plains, NY 12567

  6 Sheldon Dr, Pine Plains, NY 12567
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  $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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  $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

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  43 Stissing Mountain Dr, Pine Plains, NY 12567
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  Est $657,386 Not Listed For Sale

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

  2067 Route 83, Pine Plains, NY 12567

  2067 Route 83, Pine Plains, NY 12567
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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. Newly renovated home on North. Adjoining 8 acre vacant lot to the South available for 199,000. Owner financing possible.

  David Birch Barns & Farms Realty, LLC

  620 Bean River 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 $336,074

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  3088 Church St, Pine Plains, NY 12567
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  Est $385,250 Not Listed For Sale

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

  3018 Church St, Pine Plains, NY 12567

  3018 Church St, Pine Plains, NY 12567
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  $145,000

  • Land
  • 3.45 Acres
  • $42,029 per Acre

  66 Ryan Rd, Pine Plains, NY 12567

  Build your dream home in the heart of Pine Plains, surrounded by nature, history, and vibrant Hudson Valley living, on this exceptional 3.45 Acre elevated homesite, Board of Health approved for a 4-bedroom residence, with sweeping views of majestic Stissing Mountain. This remarkable parcel offers the perfect blend of tranquility, natural beauty, and convenience, presenting a rare opportunity to

  Vida Odescalchi Legacy Land & Homes LLC

  66 Ryan Rd, 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 $8,307,768

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

  25 Winchell Trail, Pine Plains, NY 12567
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  Est $471,121 Not Listed For Sale

  • 6 Beds
  • 2,550 Sq Ft

  17 Smith St, Pine Plains, NY 12567

  17 Smith St, Pine Plains, NY 12567
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  $150,000 Pending

  • Land
  • 0.93 Acre
  • $161,290 per Acre

  58 Britton St, Pine Plains, NY 12567

  Two lots sold together totaling just under 1 acre. 1000 gallon concrete septic tank and leach fields already in place. Drilled well complete. Under ground 200 amp electric service installed. Current mobile home will be removed. Flat lot with all utilities in a well established residential area just waiting for a new home.

  Richard Brenner Rich Brenner Realty, LLC

  58 Britton St, 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 $528,329 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,643 Sq Ft

  7760 S Main St, Pine Plains, NY 12567

  7760 S Main St, Pine Plains, NY 12567
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  $213,750

  • 4 Beds
  • 2.5 Baths
  • 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
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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 $426,290 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,165 Sq Ft

  17 Farview Ave, Pine Plains, NY 12567

  17 Farview Ave, Pine Plains, NY 12567

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