Pine Plains, NY Homes

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  /30

  $849,900

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,352 Sq Ft

  521 Hall Hill Rd Unit 18, Ancram, NY 12502

  This home is perfect for entertaining, with multiple indoor and outdoor spaces. The custom-designed kitchen, complete with an ice maker, two separate ovens, and a gas stove, is ideal for hosting large holiday gatherings. The open living room and kitchen layout make it easy for conversation to flow. Upstairs, you'll find three oversized bedrooms, including a master suite with a newly remodeled

  

  Tracy Boomhower

  Country Views Realty Inc

  521 Hall Hill Rd Unit 18, Ancram, NY 12502
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  /50

  Starting at $2,750 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

  

  51 Hillside Rd, Pine Plains, NY 12567
• 

  $415,000

  Sold Oct 14, 2025

  1601 Route 199, Red Hook, NY 12571

  • 3 Beds
  • 2 Baths
  • 1,097 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $378/SF
  • 30 Days On Market

  Current Estimated Value $446,000

  Last Listing Agent Jason Schobert eXp Realty

  1601 Route 199, Red Hook, NY 12571
• 

  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
• 

  

  

  /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

  476 Carpenter Hill Rd, 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
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  /13

  $924,500

  Sold Aug 07, 2025

  Tbd Woods Dr, Ancramdale, NY 12503

  • Land
  • 105.45 Acres
  • $8,767 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 113 Days On Market

  Last Listing Agent Arlena Armstrong Anatole House LLC

  Tbd Woods Dr, Ancramdale, NY 12503
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  /38

  Est $1,967,653

  Not Listed For Sale

  88 Friar Tuck Rd, Ancramdale, NY 12503

  • 6 Beds
  • 3.5 Baths
  • 3,804 Sq Ft
  • Built 1880

  88 Friar Tuck Rd, Ancramdale, NY 12503

  Last Sold Summary

  • 202 Days On Market
• 

  

  /23

  $599,000

  $66K PRICE DROP

  • 7 Beds
  • 5 Baths
  • 3,500 Sq Ft

  80 County Route 7, Pine Plains, NY 12567

  This beautifully updated legal 2-family home seamlessly blends vintage charm with modern convenience, offering exceptional flexibility for multigenerational living, rental income, or guest accommodations. Located just 7 minutes from Pine Plains Village and set on a scenic lot with sweeping countryside views and a neighboring 200-acre farm, the property features meticulously maintained grounds,

  

  Margaret Mondello

  Margaret Mondello Real Estate

  80 County Route 7, 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
• 

  $285,000

  Sold May 12, 2026

  84 North Rd, Red Hook, NY 12571

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • Built 1800

  Last Sold Summary

  • 12% Below List Price
  • $198/SF
  • 183 Days On Market

  Current Estimated Value $315,095

  Last Listing Agent Catherine Mondello Mondello Upstate Properties

  84 North Rd, Red Hook, NY 12571
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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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  /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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  /15

  $2,750 Per Month

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

  17 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

  17 Hillside Rd, Pine Plains, NY 12567
• 

  $440,000

  Sold Jun 17, 2026

  30 Myrtle Ave, Pine Plains, NY 12567

  • 3 Beds
  • 2 Baths
  • 1,298 Sq Ft
  • Built 1845

  Last Sold Summary

  • 10% Below List Price
  • $339/SF
  • 185 Days On Market

  Current Estimated Value $444,456

  Last Listing Agent Ellen Mallet

  30 Myrtle Ave, Pine Plains, NY 12567
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  /9

  Not Listed For Sale

  0 County Route 11, Pine Plains, NY 12567

  0 County Route 11, Pine Plains, NY 12567

  Last Sold Summary

  • 69 Days On Market
• 

  

  /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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  /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
• 

  $4,970,000

  Sold Mar 09, 2026

  310 Carpenter Hill Rd, Pine Plains, NY 12567

  • 5 Beds
  • 5.5 Baths
  • 6,310 Sq Ft
  • Built 1993

  Last Sold Summary

  • 11% Below List Price
  • $788/SF
  • 239 Days On Market

  Current Estimated Value $3,554,979

  Last Listing Agent PAULA REDMOND Corcoran Country Living

  310 Carpenter Hill Rd, Pine Plains, NY 12567
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  Not Listed For Sale

  0 - TBD County Route 7, Copake, NY 12516

  0 - TBD County Route 7, Copake, NY 12516

  Last Sold Summary

  • 202 Days On Market
• 

  

  /34

  $2,600,000

  Pending

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

  3778 New York 82, Ancramdale, NY 12503

  Set up a hillside on over 76 acres, this architectural gem looks over a magnificent valley nestled in gentle rolling hills, meadows and woodlands with views to distant mountains. It's a private artist's retreat and gardener's dream and on the market for the first time in over 35 years. The overall design was conceived by the owner/architect Sam Brody, and features a 4,250 SF main home connected

  Simone Consor Corcoran Country Living

  3778 New York 82, Ancramdale, NY 12503
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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
• 

  $390,000

  Sold Aug 11, 2025

  285 South Rd, Stanfordville, NY 12581

  • Land
  • 24.99 Acres
  • $15,606 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 54 Days On Market

  Current Estimated Value $401,947

  Last Listing Agent Michael Tellerday Houlihan Lawrence Inc.

  285 South Rd, Stanfordville, NY 12581
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  /3

  Not Listed For Sale

  0 County Route 7 Unit 144952, Pine Plains, NY 12567

  0 County Route 7 Unit 144952, Pine Plains, NY 12567

  Last Sold Summary

  • 659 Days On Market
• 

  

  /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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  /18

  $5,500 Per Month

  • 2 Beds
  • 2.5 Baths
  • 4,000 Sq Ft
  • House for Rent

  156 County Route 7, Pine Plains, NY 12567

  All you can say when entering The Barn is AMAZING! Converted 1800's three level barn with original beams and reclaimed wood for flooring and elsewhere. The dramatic open living room and dining areas have walls of glass and soaring ceilings. The upper floor is an open bedroom suite with space for an office, sitting area and has an outside balcony. There is geothermal radiant heat and A/C.

  ANN SIMMONS Compass Greater NY, LLC

  156 County Route 7, Pine Plains, NY 12567
• 

  

  /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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  Not Listed For Sale

  0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503

  • 4 Beds
  • 3 Baths
  • 4,144 Sq Ft
  • Built 2000

  0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503

  Last Sold Summary

  • 428 Days On Market
• 

  /2

  $475,000

  • Land
  • 7 Acres
  • $67,857 per Acre

  8 McGhee Hill Rd, Millerton, NY 12546

  This gorgeous 7.9 acre estate lot is at the east end McGhee Hill Road and only minutes from the vibrant village of Millerton. Lot 8 is entirely Board of Health approved and shovel-ready with all improvements, a cut driveway from McGhee Hill Road and stone pillared entrance. Sited just west of Rte 22 on McGhee Rill Road, this lot is surrounded by other large parcels offering privacy and bucolic

  Jason Karadus Corcoran Country Living

  8 McGhee Hill Rd, Millerton, NY 12546
• 

  

  /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
• 

  $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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  Not Listed For Sale

  0 Hill Top Rd Unit ONEH6333617, Gallatin, NY 12502

  0 Hill Top Rd Unit ONEH6333617, Gallatin, NY 12502

  Last Sold Summary

  • 85 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
• 

  

  /15

  $2,825 Per Month

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

  11 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

  11 Hillside Rd, Pine Plains, NY 12567
• 

  

  /49

  $545,000

  Sold Mar 03, 2026

  1301 County Route 7, Ancram, NY 12502

  • 3 Beds
  • 3 Baths
  • 2,184 Sq Ft
  • Built 1894

  Last Sold Summary

  • 13% Below List Price
  • $250/SF
  • 112 Days On Market

  Current Estimated Value $606,858

  Last Listing Agent Anthony D'Argenzio Houlihan Lawrence Inc.

  1301 County Route 7, Ancram, NY 12502
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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
• 

  

  /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 or with 12 acres (3 building lots) for 713000.

  David Birch Barns & Farms Realty, LLC

  618 Bean River Rd, Pine Plains, NY 12567
• 

  

  /33

  $1,800 Per Month

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

  525 Lake Rd Unit 3, Pine Plains, NY 12567

  Come home to the Lake !! Nicely renovated 1 Bedroom Apartment. Also has a Den/Office. All new Kitchen & Bath. Includes new dishwasher, new state-of-the-art gas range, new refrigerator & microwave. All new bathroom fixtures and tiled floor. Situated up a hill with a great view of the beautiful Twin Island Lake - some lake rights included. The fishing is excellent! Landlord pays heat, hot water,

  MICHELLE FRANCESE Corcoran Country Living

  525 Lake Rd Unit 3, Pine Plains, NY 12567
• 

  $2,153,550

  Sold Mar 04, 2026

  820 Cold Spring Rd, Stanfordville, NY 12581

  • 3 Beds
  • 2.5 Baths
  • 2,267 Sq Ft
  • Built 2025

  Last Sold Summary

  • 8% Above List Price
  • $950/SF
  • 166 Days On Market

  Last Listing Agent DOUG MAXWELL Upstate Modernist

  820 Cold Spring Rd, Stanfordville, NY 12581
• 

  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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