2,842

Pine Plains, NY Homes

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  • 8032-8060 New York 82, Pine Plains, NY 12567
    8032-8060 New York 82, Pine Plains, NY 12567
    8032-8060 New York 82, Pine Plains, NY 12567
    /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
  • 32 Town Centre Rd, Pine Plains, NY 12567
    32 Town Centre Rd, Pine Plains, NY 12567
    32 Town Centre Rd, Pine Plains, NY 12567
    /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
  • 461 Silvernails Rd, 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 $5,435,171

    Last Listing Agent Byron Anderson Compass Greater NY, LLC

    461 Silvernails Rd, Pine Plains, NY 12567
  • 280 Hall Hill Rd, Ancram, NY 12502
    280 Hall Hill Rd, Ancram, NY 12502
    280 Hall Hill Rd, Ancram, NY 12502
    /19

    $249,000

    • 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
  • 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 $746,761

    Last Listing Agent Joseph Iannibelli Keller Williams NY Realty

    546 Hicks Hill Rd, Stanfordville, NY 12581
    • 218 Mountain Rd, Stanfordville, NY 12581
      218 Mountain Rd, Stanfordville, NY 12581
      218 Mountain Rd, Stanfordville, NY 12581
      /33

      Est $800,109

      Not Listed For Sale

      218 Mountain Rd, Stanfordville, NY 12581

      • 3 Beds
      • 2.5 Baths
      • 2,486 Sq Ft
      • Built 2002
      218 Mountain Rd, Stanfordville, NY 12581

      Last Sold Summary

      • 82 Days On Market

  • Tbd Hicks Hill Rd, Pine Plains, NY 12567
    Tbd Hicks Hill Rd, Pine Plains, NY 12567
    Tbd Hicks Hill Rd, Pine Plains, NY 12567
    /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
  • 1388 Route 83, Pine Plains, NY 12567

    $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 $790,119

    Last Listing Agent Jill Rose Houlihan Lawrence Inc.

    1388 Route 83, Pine Plains, NY 12567
    • 599 Bean River Rd, Millerton, NY 12546
      599 Bean River Rd, Millerton, NY 12546
      599 Bean River Rd, Millerton, NY 12546
      /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

  • 0 Hall Hill Rd Unit KEY998490, Ancram, NY 12502
    0 Hall Hill Rd Unit KEY998490, Ancram, NY 12502
    0 Hall Hill Rd Unit KEY998490, Ancram, NY 12502
    /11

    $325,000

    • Land
    • 24.9 Acres
    • $13,052 per Acre

    0 Hall Hill Rd Unit KEY998490, Ancram, NY 12502

    Privately tucked away along one of Ancram’s most picturesque country roads, this beautiful approximately 25-acre offering presents a rare opportunity to create a secluded full-time residence or weekend retreat in the heart of the Hudson Valley. Quiet and rural, yet conveniently located just 8 minutes to Pine Plains, 15 minutes to Millerton and Copake, and under 30 minutes to Hudson, Red Hook, and

    Ann Stettner Neil Charles Real Estate, LLC

    0 Hall Hill Rd Unit KEY998490, Ancram, NY 12502
  • 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 $533,869

    Last Listing Agent Arleen Shepley Elyse Harney Real Estate

    30 N Main St, Pine Plains, NY 12567
    • 3327 Route 199, Pine Plains, NY 12567
      3327 Route 199, Pine Plains, NY 12567
      3327 Route 199, Pine Plains, NY 12567
      /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

  • 1598 Jackson Corners Rd, Red Hook, NY 12571
    1598 Jackson Corners Rd, Red Hook, NY 12571
    1598 Jackson Corners Rd, Red Hook, NY 12571
    /36

    $1,499,000

    $200K PRICE DROP Pending
    • 5 Beds
    • 3.5 Baths
    • 4,176 Sq Ft

    1598 Jackson Corners Rd, Red Hook, NY 12571

    Welcome to Fallkill Farm, an incredible 37 acre oasis with expansive meadows, wooded buffers, mountain backdrop and Roeliff Jansen Kill frontage. Historic significance and modern amenities converge with the impeccably restored circa 1800 farmhouse featuring updated kitchen w/center island, designer cabinetry, Subzero refrigerator, Wolfe range and soapstone counters. Loaded with period features

    Dan Axtmann BHHS Hudson Valley Properties

    1598 Jackson Corners Rd, Red Hook, NY 12571
  • 53 Brooks 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
  • 303 Hicks Hill Rd, Stanfordville, NY 12581
    303 Hicks Hill Rd, Stanfordville, NY 12581
    303 Hicks Hill Rd, Stanfordville, NY 12581
    /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
  • 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 $555,663

    Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

    43 Stissing Mountain Dr, Pine Plains, NY 12567
  • 71 Lake Shore Dr, Pine Plains, NY 12567
    71 Lake Shore Dr, Pine Plains, NY 12567
    71 Lake Shore Dr, Pine Plains, NY 12567
    /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
  • 100 Knob Hill Rd, Stanfordville, NY 12581

    $595,000

    Sold Feb 19, 2026

    100 Knob Hill Rd, Stanfordville, NY 12581

    • 3 Beds
    • 1.5 Baths
    • 1,725 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Above List Price
    • $345/SF
    • 27 Days On Market

    Current Estimated Value $596,664

    Last Listing Agent Kimberly Wickes R. Ferris Real Estate, LLC

    100 Knob Hill Rd, Stanfordville, NY 12581
    • 3066 Church St, Pine Plains, NY 12567
      3066 Church St, Pine Plains, NY 12567
      3066 Church St, Pine Plains, NY 12567
      /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

  • 620 Bean River Rd, Pine Plains, NY 12567
    620 Bean River Rd, Pine Plains, NY 12567
    620 Bean River Rd, Pine Plains, NY 12567
    /7

    $138,000

    $1K PRICE DROP
    • Land
    • 4.24 Acres
    • $32,547 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 (probably 10 feed are shared). Newly renovated home on North. Adjoining 8 acre vacant lot to the South available for 199,000. Both lots for 300,000. Owner financing possible.

    David Birch Barns & Farms Realty, LLC

    620 Bean River Rd, Pine Plains, NY 12567
    • 10 Academy St, Pine Plains, NY 12567
      10 Academy St, Pine Plains, NY 12567
      10 Academy St, Pine Plains, NY 12567
      /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

  • 236 South Rd, Stanfordville, NY 12581
    236 South Rd, Stanfordville, NY 12581
    236 South Rd, Stanfordville, NY 12581
    /28

    $689,000

    $10K PRICE DROP
    • 3 Beds
    • 5 Baths
    • 3,500 Sq Ft

    236 South Rd, Stanfordville, NY 12581

    Spacious legal mother-daughter ranch offering 3 bedrooms, 3 full baths, and 2 half baths—ideal for extended or multi-generational living.The upper level features two bedrooms plus a versatile office space, a bright kitchen, and a formal dining area. The primary suite includes a walk-in closet and a private full bath, with sliding glass doors off of living room leading to a secluded

    Don Maher BHHS Hudson Valley Properties

    236 South Rd, Stanfordville, NY 12581
  • 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
  • 82 Lake Rd, Pine Plains, NY 12567
    82 Lake Rd, Pine Plains, NY 12567
    82 Lake Rd, Pine Plains, NY 12567
    /38

    $485,000

    $4K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    82 Lake Rd, Pine Plains, NY 12567

    A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite

    MICHELLE FRANCESE Corcoran Country Living

    82 Lake 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
  • 284 Hall Hill Rd Unit Stop 18, Ancram, NY 12502
    284 Hall Hill Rd Unit Stop 18, Ancram, NY 12502
    284 Hall Hill Rd Unit Stop 18, Ancram, NY 12502
    /14

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,768 Sq Ft

    284 Hall Hill Rd Unit Stop 18, Ancram, NY 12502

    Discover the Charm of Country Living Escape to this authentic 3-bedroom, 2-bath log home tucked away on a peaceful private road in Ancram. Set on 5 acres, the property also includes a separate 3-acre buildable lot across the lane-perfect for maintaining privacy, creating a guest house or studio, or simply preserving your view and open space. Start your day with coffee on the front porch, or soak

    Kelly Harrison Taconic Valley Real Estate

    284 Hall Hill Rd Unit Stop 18, Ancram, NY 12502
  • 1283 County Route 7, Ancram, NY 12502
    1283 County Route 7, Ancram, NY 12502
    1283 County Route 7, Ancram, NY 12502
    /32

    $280,000

    Sold Aug 01, 2025

    1283 County Route 7, Ancram, NY 12502

    • 3 Beds
    • 1.5 Baths
    • 1,368 Sq Ft
    • Built 1880

    Last Sold Summary

    • 6% Below List Price
    • $205/SF
    • 73 Days On Market

    Current Estimated Value $323,581

    Last Listing Agent Margaret Clarke Corcoran Country Living

    1283 County Route 7, Ancram, NY 12502
    • 43 Lake Shore Dr, Pine Plains, NY 12567
      43 Lake Shore Dr, Pine Plains, NY 12567
      43 Lake Shore Dr, Pine Plains, NY 12567
      /31

      Est $814,262

      Not Listed For Sale

      43 Lake Shore Dr, Pine Plains, NY 12567

      • 1 Bed
      • 0.5 Baths
      • 936 Sq Ft
      • Built 1960
      43 Lake Shore Dr, Pine Plains, NY 12567

      Last Sold Summary

      • 155 Days On Market

  • 559 Lake Rd, Pine Plains, NY 12567
    559 Lake Rd, Pine Plains, NY 12567
    559 Lake Rd, Pine Plains, NY 12567
    /50

    $549,000

    • 2 Beds
    • 2 Baths
    • 1,456 Sq Ft

    559 Lake Rd, Pine Plains, NY 12567

    Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has a proven track record as a highly successful Airbnb. Whether you are looking for a lucrative investment, a dream summer getaway, or a year-round sanctuary, this home has it all. The entire front of the house features stunning, unobstructed lake views. Start your mornings on

    KELLY ROMANO Keller Williams Realty

    559 Lake Rd, Pine Plains, NY 12567
  • 1691 Jackson Corners Rd, Red Hook, NY 12571

    $100,000

    Sold Sep 10, 2025

    1691 Jackson Corners Rd, Red Hook, NY 12571

    • 2 Beds
    • 1.5 Baths
    • 984 Sq Ft
    • Built 1970

    Last Sold Summary

    • 47% Below List Price
    • $102/SF
    • 79 Days On Market

    Last Listing Agent Catherine Mondello Mondello Upstate Properties

    1691 Jackson Corners Rd, Red Hook, NY 12571
  • 000 New York 82, Pine Plains, NY 12567
    000 New York 82, Pine Plains, NY 12567
    000 New York 82, Pine Plains, NY 12567
    /8

    $345,000

    • Land
    • 68.33 Acres
    • $5,049 per Acre

    000 New York 82, Pine Plains, NY 12567

    This beautiful, gently sloping parcel offers the perfect canvas to create your country escape or full-time residence on 68+ private acres. Soil tests complete for two building sites. Some clearing would offer ridgeline views to the south and west. Roughed-in driveway is in place, so you're well on your way to building a home that's tailored exactly to your needs. Just 20 minutes to Hudson and Red

    Jeffries Blackerby Houlihan Lawrence Inc.

    000 New York 82, Pine Plains, NY 12567
  • 00-1 New York 82, Pine Plains, NY 12567
    00-1 New York 82, Pine Plains, NY 12567
    00-1 New York 82, Pine Plains, NY 12567
    /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

Showing Results 41 - 80, Page 2 of 18

New York Dutchess County Pine Plains

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