Pine Plains Homes

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  /40

  $2,995,000

  $1M PRICE DROP

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

  476 Carpenter Hill Rd, Pine Plains, NY 12567

  Modern Minimalist Estate on 19 Bucolic Acres in Dutchess County, NY. A rare Hudson Valley offering where bold modern design meets pastoral beauty. Completed in late 2024, this 4,700+ sq ft single-level home sits on 19 acres of flat, fenced farmland along scenic Shekomeko Creek. The residence features a 3,057+/-sq ft main house, 1,046+/- sq ft greenhouse-conservatory, and 1,423 +/-sq ft heated

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (518) 594-8655

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

  Starting at $2,660 Per Month

  • 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

  Stissing Farms

  (845) 868-0476

  

  51 Hillside 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
• 

  Est $2,074,000

  Not Listed For Sale

  454 Bean River Rd, Pine Plains, NY 12567

  454 Bean River Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 194 Days On Market
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  /34

  $394,000

  $5K PRICE DROP

  • 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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  /6

  $2,750

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Condo for Rent

  144 N Main St Unit Front Apt, Pine Plains, NY 12567

  Twin Cottage Home /Pine Pains Apartment Rental2BR/2FULL BATHS/NEW APPLIANCES/ELECTRIC,HEATING,COOLING INCSIDE PATIO DECK/NO SMOKING/SMALL PET OK**RENTERS INSURANCE REQUIRED

  144 N Main St Unit Front Apt, Pine Plains, NY 12567
• 

  $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 $307,376

  Last Listing Agent Blake Michaud BHHS Hudson Valley Properties

  34 Myrtle Ave, Pine Plains, NY 12567
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  /2

  Est $554,273

  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
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  /35

  $499,000

  • 4 Beds
  • 1.5 Baths
  • 3,072 Sq Ft

  7786 S Main St, Pine Plains, NY 12567

  Step into the charm and character of a bygone era with this spacious early-1900s Colonial-style home located in the heart of the hamlet of Pine Plains. Offering over 3,000 square feet of living space, this 4-bedroom, 1.5-bath residence sits on approximately 0.47 acres and is filled with history, warmth, and timeless architectural details.Once home to both the town pharmacy and library, this

  Richard Brenner Rich Brenner Realty, LLC

  7786 S Main St, Pine Plains, NY 12567
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  /28

  $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
• 

  $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 $746,761

  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

  • 346 Days On Market
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  /47

  $469,000

  $21K PRICE DROP Pending

  • 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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  /13

  $1,500 Per Month

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft
  • Apartment for Rent

  2815 Church St, Pine Plains, NY 12567

  A large and roomy one bedroom apartment awaits you in lovely Pine Plains NY. Situated right on West Church St, this south-facing and sunny apartment has a large living room, an eat-in kitchen, a good-sized bedroom, full bath, and plenty of closets. It’s right near the public school, and is walkable to all the local shops, restaurants, and the Stissing Center for the Performing Arts. Pine Plains

  David Norman Hall Houlihan Lawrence, Inc

  2815 Church St, Pine Plains, NY 12567
• 

  $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 $533,869

  Last Listing Agent Arleen Shepley Elyse Harney Real Estate

  30 N Main St, Pine Plains, NY 12567
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  Est $2,731,355

  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
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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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  /15

  $2,825 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
• 

  $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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  /3

  Est $355,872

  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
• 

  

  /20

  $410,000

  Pending

  • 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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  /21

  $4,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,350 Sq Ft
  • House for Rent

  3411 Route 199, Pine Plains, NY 12567

  Located on the grounds of a 119+ acre estate, this 2,300+ square foot home has been totally renovated and offers ease of living in a beautiful setting. The first floor of this home comprises a living room with wood burning fireplace, formal dining room with large bow window, spacious eat-in-kitchen, lovely den/office and a half bath. The second floor has a master suite, 2 additional bedrooms and

  Paula Redmond Corcoran Country Living - Mill

  3411 Route 199, Pine Plains, NY 12567
• 

  $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 $555,663

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

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

  Est $658,609

  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
• 

  

  /15

  $387,000

  $2K PRICE DROP

  • 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 588000 with additional 12 acres (3 building lots) for 713000

  David Birch Barns & Farms Realty, LLC

  618 Bean River Rd, Pine Plains, NY 12567
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  /29

  $35,000 Per Month

  • 7 Beds
  • 9 Baths
  • 7,617 Sq Ft
  • House for Rent

  200 Chase Rd, Pine Plains, NY 12567

  SUMMER RENTAL. Available July & August for 35,000 per month. Overlooking 119+ acres of rolling hills this property offers an ideal setting for the perfect country lifestyle. The spacious country house with seven en-suite bedrooms and has been fully customized with generously sized rooms, crown moldings and beautiful flooring throughout. Outdoor features include a large bluestone terrace, heated

  Paula Redmond Corcoran Country Living - Mill

  200 Chase Rd, 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
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  Est $648,988

  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

  • 53 Days On Market
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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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  /17

  $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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  /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 $6,100,931

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

  25 Winchell Trail, Pine Plains, NY 12567
• 

  Est $347,082

  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
• 

  

  /31

  $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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  /15

  $2,660 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
• 

  $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
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  /16

  Est $327,776

  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
• 

  

  /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
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  /13

  $1,500 Per Month

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft
  • Apartment for Rent

  2815 W Church St Unit B, Pine Plains, NY 12567

  A large and roomy one bedroom apartment awaits you in lovely Pine Plains NY. Situated right on West Church St, this south-facing and sunny apartment has a large living room, an eat-in kitchen, a good-sized bedroom, full bath, and plenty of closets. It's right near the public school, and is walkable to all the local shops, restaurants, and the Stissing Center for the Performing Arts. Pine Plains

  David Norman Hall Houlihan Lawrence Inc.

  2815 W Church St Unit B, 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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  /7

  Est $203,765

  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

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