1,445

Pine Plains Homes

Section Image
  • /8

    $3,495,000

    • Land
    • 234 Acres
    • $14,936 per Acre

    317 Skunks Misery Rd, Millerton, NY 12546

    Rarely does a property of this caliber become available. Spanning approximately 234 acres across two contiguous parcels (162 acres and 71.5 acres), this exceptional offering features productive hay and corn fields, rolling farmland, mature woodlands, and breathtaking long-range views of the Taconic Mountains and Catskills. Multiple elevated building sites provide the opportunity to create a

    Helen Murray William Pitt Sothebys Int Rlty

    317 Skunks Misery Rd, Millerton, NY 12546
  • /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
  • 30 Myrtle Ave, 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
  • /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
  • /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
  • /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
    • /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
  • /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
    • /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

  • /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
  • 34 Myrtle Ave, 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 $310,642

    Last Listing Agent Blake Michaud BHHS Hudson Valley Properties

    34 Myrtle Ave, Pine Plains, NY 12567
    • 420 Carpenter Hill Rd, Pine Plains, NY 12567

      Est $2,508,084

      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

      Last Listing Agent LINDSAY BALDWIN Houlihan Lawrence Inc.

  • /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
  • 546 Hicks Hill Rd, Stanfordville, NY 12581

    $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
    • /3

      Est $368,628

      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

      Last Listing Agent Christopher Virtuoso Keller Williams Realty HV Nort

  • /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
  • 30 N Main 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 $549,158

    Last Listing Agent Arleen Shepley Elyse Harney Real Estate

    30 N Main St, Pine Plains, NY 12567
    • /43

      Est $663,471

      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

      Last Listing Agent Audrey Winslow Houlihan Lawrence Inc.

  • /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
  • 43 Stissing Mountain Dr, 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 $597,457

    Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

    43 Stissing Mountain Dr, Pine Plains, NY 12567
    • 3088 Church St, Pine Plains, NY 12567

      Est $358,055

      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

      Last Listing Agent Richard Brenner Rich Brenner Realty, 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
  • 58 Britton St, 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
    • /16

      Est $336,667

      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

      Last Listing Agent Brad Rebillard Past Member

  • /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
  • 22-28 Ryan 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
    • /7

      Est $199,372

      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

      Last Listing Agent Libby McKee Berkshire Hathaway HomeService

  • /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
  • /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
    • 7760 S Main St, Pine Plains, NY 12567

      Est $598,864

      Not Listed For Sale

      7760 S Main St, Pine Plains, NY 12567

      • 3 Beds
      • 2 Baths
      • 1,643 Sq Ft
      • Built 1960
      7760 S Main St, Pine Plains, NY 12567

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent CHRISTINE BATES William Pitt Sotheby's Int'l

  • /14

    $220,000

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    16 Ryan Rd, Pine Plains, NY 12567

    Welcome to 16 Ryan Road, a spacious 3-bedroom, 2-bathroom home in the scenic Pine Plains area. Featuring a large kitchen with plenty of workspace, a center island, and a functional layout with generous living areas, this home offers a great foundation for your next project.The property needs some updating and is ideal for a buyer looking to add their own personal touches and build equity.

    Jasper Newman Charles Rutenberg Realty Inc

    16 Ryan Rd, Pine Plains, NY 12567
  • 37 Stissing Mountain Dr, Pine Plains, NY 12567

    $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
    • 2854 Church St, Pine Plains, NY 12567

      Est $810,271

      Not Listed For Sale

      2854 Church St, Pine Plains, NY 12567

      • 3 Beds
      • 2 Baths
      • 2,208 Sq Ft
      • Built 1911
      2854 Church St, Pine Plains, NY 12567

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Diana Bisselle William Pitt Sothebys Int Rlty

  • /49

    $975,000

    • Land
    • 37,026 Sq Ft
    • $1,147,059 per Acre

    71 Lake Shore Dr, Pine Plains, NY 12567

    The Ultimate Hudson Valley Lakefront Package: Waterfront Mainland Barn, Private Island Glamping Airbnb, Ease Side Lake Access Land & Endless Views!Welcome to a truly unprecedented real estate opportunity on the pristine waters of Twin Island Lake in beautiful Pine Plains, NY. This isn’t just a land listing; it is an extraordinary three-parcel package deal that blends rustic charm, income

    KELLY ROMANO Keller Williams Realty

    71 Lake Shore Dr, Pine Plains, NY 12567
  • 390 Carpenter Hill Rd, Pine Plains, NY 12567

    $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 $1,118,147

    Last Listing Agent Dan Kessler Compass Greater NY, LLC

    390 Carpenter Hill Rd, Pine Plains, NY 12567

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$528,750
Median Single Family Sale Price
$520,000
Median Townhouse Sale Price
$835,000
Median 2 Bedroom Sale Price
$469,000
Median 1 Bedroom Sale Price
$395,000
Average Price Per Sq Ft
$321
Number of Homes for Sale
16
Last 12 months Home Sales
20
Months of Supply
9.60
Median List Price
$591,500
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-10%
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