7

5-Bedroom Homes for Sale in Pine Plains, NY

Section Image
  • /45

    $5,600,000

    • 5 Beds
    • 4.5 Baths
    • 6,310 Sq Ft

    310 Carpenter Hill Rd, Pine Plains, NY 12567

    Nestled on top of Carpenter Hill, with unparalleled views of Stissing Mountain, the Catskills and the surrounding farmland, sits this country estate on 24.78 acres. The traditional, cedar shake 6,310 square foot home exudes elegance exhibited through the well proportioned rooms with 9’4” ceiling height, exceptional craftmanship and attention to detail found throughout the home. A dramatic double

    PAULA REDMOND Corcoran Country Living

    310 Carpenter Hill Rd, Pine Plains, NY 12567
  • /43

    $1,300,000

    • 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
  • /36

    $1,699,000

    • 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
  • /40

    $2,950,000

    • 5 Beds
    • 3.5 Baths
    • 3,264 Sq Ft

    182 Hill Top Rd, Pine Plains, NY 12567

    Luxurious modern farmhouse on 16.17 acres of pristine conservation land within a protected 660-acre viewshed, two ponds, sweeping mountain and country vistas to savor from the wraparound porch, soaring ceiling heights, clean lines and carefully crafted materials from a 2023 comprehensive design-forward renovation featured in Elle Decor.In the main house, the new chef's kitchen gleams with

    Katherine Wood Patricia A. Hinkein Realty

    182 Hill Top Rd, Pine Plains, NY 12567
  • /36

    $12,000,000

    • 5 Beds
    • 3.5 Baths
    • 6,340 Sq Ft

    118 Finkle Rd, Ancramdale, NY 12503

    Set among the beautiful rolling hills on 203 acres is this private estate that takes you back in time. The farm was built in 2008 around a c.1754 Dutch barn that was dismantled from upstate NY and transformed into an incredible great room with 34' soaring ceilings, a brick fireplace and two huge French doors to take in the view. Designed by Cynthia Filkoff with 6,340 square feet, the main house

    PAULA REDMOND Corcoran Country Living - Mill

    118 Finkle Rd, Ancramdale, NY 12503
  • /29

    $7,400,000

    • 9 Beds
    • 11 Baths
    • 9,000 Sq Ft

    255 Mill Hill Rd, Pine Plains, NY 12567

    A long driveway leads to this imposing Greek Revival style house set high on a hill on 200 + acres of prime land overlooking Hudson Valley's farm country. Open fields and woodland with1600' of frontage on the Roeliff Jansen Kill. The house has 9000 sq ft with 12' ceilings throughout, large areas for entertaining, surrounding balconies for summer living and a 5000 bottle wine cave. The kitchen

    HEATHER CRONER Heather Croner Real Estate SIR

    255 Mill Hill Rd, Pine Plains, NY 12567
  • /36

    $2,995,000

    • 6 Beds
    • 5.5 Baths
    • 4,000 Sq Ft

    53 Brooks Rd, Pine Plains, NY 12567

    Welcome to Library Valley Estate, a creative 3-home compound in Dutchess County, NY. This serene, terraced property features a lovingly restored 19th-century farmhouse, a spacious barn-style home with a vaulted ceiling and oversized sliding glass doors, and a cozy loft studio, each offering stunning views of the rolling meadows. Enjoy a heated gunite pool, mature gardens, a quaint pond, and

    Anthony D'Argenzio Houlihan Lawrence, Inc

    53 Brooks Rd, Pine Plains, NY 12567
How to Buy a Home How to Finance a Home How to Sell a Home