Pine Plains, NY Homes

• 

  

  

  /30

  $825,000

  $75K 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
• 

  

  

  /50

  Starting at $2,750 Per Month

  • 2 Beds

  51 Hillside Rd, Pine Plains, NY 12567

  One Month Free on a 13 month Lease!

  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 $445,000

  Last Listing Agent Jason Schobert eXp Realty

  1601 Route 199, Red Hook, NY 12571
• 

  Est $1,667,224

  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

  Last Listing Agent PAULA REDMOND Corcoran Country Living
• 

  

  

  /19

  $575,000

  $90K PRICE DROP

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

  80 County Route 7, Pine Plains, NY 12567

  Stunning renovated Colonial farmhouse set in a peaceful country setting with beautiful pastoral views, just minutes to the Village of Pine Plains. Completely updated in 2020, this spacious home offers the perfect blend of classic charm and modern finishes.The main residence features 4 large bedrooms and 3 full bathrooms, a gracious formal dining room, and a bright, open kitchen with tile

  

  Margaret Mondello

  Margaret Mondello Real Estate

  80 County Route 7, Pine Plains, NY 12567
• 

  

  /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
• 

  $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 $316,645

  Last Listing Agent Catherine Mondello Mondello Upstate Properties

  84 North Rd, Red Hook, NY 12571
• 

  

  /38

  Est $2,054,182

  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

  Last Listing Agent Ann Simmons Past Member
• 

  

  /34

  $394,000

  $5K PRICE DROP Pending

  • 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
• 

  

  /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
• 

  $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 $442,310

  Last Listing Agent Ellen Mallet Houlihan Lawrence Inc.

  30 Myrtle Ave, Pine Plains, NY 12567
• 

  /2

  Est $568,475

  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
• 

  

  /35

  $489,000

  $10K PRICE DROP

  • 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
• 

  

  /14

  $2,750 Per Month

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

  85 Ledge Ct, 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

  85 Ledge Ct, 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 $4,472,780

  Last Listing Agent PAULA REDMOND Corcoran Country Living

  310 Carpenter Hill Rd, Pine Plains, NY 12567
• 

  

  /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

  Last Listing Agent Melissa Vooris Past Member
• 

  

  /24

  $1,200,000

  Open Sat 11:30AM - 1:30PM

  • 3 Beds
  • 3 Baths
  • 2,968 Sq Ft

  572 Hicks Hill Rd, Stanfordville, NY 12581

  Perched high on 5.32 private acres with breathtaking, distant panoramic views of the Taconic Range and Berkshire Mountains, this contemporary home has been completely transformed by a top-to-bottom renovation. Seamlessly blending chic modern upgrades with dramatic architectural bones, this turn-key residence offers utmost privacy on a scenic country lane, yet still provides incredible

  Callan Bergmann Compass Greater NY, LLC

  572 Hicks Hill Rd, Stanfordville, NY 12581
• 

  

  /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
• 

  

  /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
• 

  

  /37

  Not Listed For Sale

  2067 County Road 83, Pine Plains, NY 12567

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

  2067 County Road 83, Pine Plains, NY 12567

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent William Golan Compass Greater NY, LLC
• 

  

  /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
• 

  

  /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
• 

  

  /20

  $400,000

  Sold Jul 31, 2026

  73 Meusel Rd, Pine Plains, NY 12567

  • 3 Beds
  • 2.5 Baths
  • 2,688 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Below List Price
  • $149/SF
  • 81 Days On Market

  Current Estimated Value $418,117

  Last Listing Agent David Norman Hall Houlihan Lawrence Inc.

  73 Meusel Rd, Pine Plains, NY 12567
• 

  Est $391,877

  Not Listed For Sale

  285 South Rd, Stanfordville, NY 12581

  285 South Rd, Stanfordville, NY 12581

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Michael Tellerday Houlihan Lawrence Inc.
• 

  /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
• 

  $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 $310,642

  Last Listing Agent Blake Michaud BHHS Hudson Valley Properties

  34 Myrtle Ave, Pine Plains, NY 12567
• 

  

  /7

  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

  Last Listing Agent Jeffries Blackerby Houlihan Lawrence Inc.
• 

  

  /15

  $359,000

  $30K PRICE DROP

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

  618 Bean River Rd, Millerton, NY 12546

  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 565000 or with 12 acres (3 building lots) for 689000.

  David Birch Barns & Farms Realty, LLC

  618 Bean River Rd, Millerton, NY 12546
• 

  

  /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 $575,809

  Last Listing Agent Anthony D'Argenzio Houlihan Lawrence Inc.

  1301 County Route 7, Ancram, NY 12502
• 

  

  /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

  Last Listing Agent Ann Simmons Past Member
• 

  

  /22

  $359,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  2795 Church St, Pine Plains, NY 12567

  Attractive 3 bedroom, 1 bath cape cod loaded with recent improvements. Attractive open floor plan includes kitchen w/stainless appliances, granite counters & breakfast bar, which flows seamlessly to living room w/fireplace. Two first floor bedrooms and tile bathroom. Second floor includes generously sized bedroom plus office/den and storage space. Three season front porch is the perfect place to

  Dan Axtmann BHHS Hudson Valley Properties

  2795 Church St, Pine Plains, NY 12567
• 

  $12,500,000

  Sold May 01, 2026

  461 Silvernails Rd, Pine Plains, NY 12567

  • 11 Beds
  • 7.5 Baths
  • 7,500 Sq Ft
  • Built 2020

  Last Sold Summary

  • 44% Below List Price
  • $1,667/SF
  • 403 Days On Market

  Current Estimated Value $5,112,350

  Last Listing Agent Byron Anderson Compass Greater NY, LLC

  461 Silvernails Rd, Pine Plains, NY 12567
• 

  

  /13

  Not Listed For Sale

  Tbd Woods Dr, Ancramdale, NY 12503

  Tbd Woods Dr, Ancramdale, NY 12503

  Last Sold Summary

  • 113 Days On Market

  Last Listing Agent Arlena Armstrong Anatole House LLC
• 

  

  /32

  $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
• 

  $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 $755,383

  Last Listing Agent Joseph Iannibelli Keller Williams NY Realty

  546 Hicks Hill Rd, Stanfordville, NY 12581
• 

  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

  Last Listing Agent Neil Charles Neil Charles Real Estate, LLC
• 

  

  /19

  $249,000

  Pending

  • 1 Bed
  • 1 Bath
  • 830 Sq Ft

  280 Hall Hill Rd, Ancram, NY 12502

  Renovated one bedroom, one bathroom with office space, on 3.37 acres. Over the past 2-3 years; new roof, well pump and tank, windows, doors, siding, appliances, oil tank, water heater, breaker box, shed and gazebo. Large parcel on a country road. Great weekend retreat or year round residence.

  Richard Brenner Rich Brenner Realty, LLC

  280 Hall Hill Rd, Ancram, NY 12502
• 

  $820,000

  Sold Jan 16, 2026

  1388 Route 83, Pine Plains, NY 12567

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft
  • Built 1880

  Last Sold Summary

  • 11% Below List Price
  • $273/SF
  • 169 Days On Market

  Current Estimated Value $799,327

  Last Listing Agent Jill Rose Houlihan Lawrence Inc.

  1388 Route 83, Pine Plains, NY 12567
• 

  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

  Last Listing Agent Andrew Gates Houlihan Lawrence Inc.
• 

  

  /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

Showing Results 1 - 40, Page 1 of 18