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Pine Plains, NY Homes for Sale with Garage

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  • /50

    $3,495,000

    • 4 Beds
    • 4 Baths
    • 4,103 Sq Ft

    476 Carpenter Hill Rd, Pine Plains, NY 12567

    Modern Minimalist Masterpiece on 19 Bucolic Acres in Dutchess County. Welcome to a rare offering in the heart of the Hudson Valley, where striking modern architecture meets timeless pastoral beauty. Completed in late 2024, this extraordinary estate sits on over 19 acres of flat, fenced farmland at the picturesque intersection of Bethel Cross and Carpenter Hill Road. Perfectly sited on a

    Agent Photo

    Rebecca Doh

    William Raveis Lifestyles Rlty

    (518) 594-8655

    476 Carpenter Hill Rd, Pine Plains, NY 12567
  • /35

    $899,900

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

    521 Hall Hill Rd Unit 18, Ancram, NY 12502

    OPEN HOUSE: Saturday, April 18th 1:00-3:00 p.m. 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,

    Agent Photo

    Tracy Boomhower

    Country Views Realty, Inc.

    (518) 299-5749

    521 Hall Hill Rd Unit 18, Ancram, NY 12502
  • /26

    $4,250,000

    • 6 Beds
    • 5 Baths
    • 6,146 Sq Ft

    468 Tripp Rd, Pine Plains, NY 12567

    We welcome this 1834 restored farm into our Luxury Collection of Hudson Valley properties. This magnificent property makes the perfect country compound. Completely updated, restored and improved to also include a new addition on the main house. This 200 acre farm has all the privacy and beauty of a true country retreat. With such amenities as a converted dairy barn to an indoor tennis court

    George Langa Houlihan Lawrence Inc.

    468 Tripp Rd, Pine Plains, NY 12567
  • /34

    $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
  • /50

    $4,395,000

    • 10 Beds
    • 6.5 Baths
    • 6,994 Sq Ft

    1515-1517 County Road 83, Pine Plains, NY 12567

    Set far back from one of the Hudson Valley’s most prestigious and scenic roads, this stunningly restored 1830s colonial farmhouse is a masterclass in combining historic charm with sophisticated living. Situated in the heart of the pastoral Shekomeko Valley on just under 10 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white

    OLIVER BROWN Houlihan Lawrence Inc.

    1515-1517 County Road 83, Pine Plains, NY 12567
  • /47

    $469,000

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

    30 Myrtle Ave, Pine Plains, NY 12567

    Welcome to the Historic Town of Pine Plains, and the Pine Plains School District! This completely renovated three bedroom home on a quiet country road will delight and intrigue you. The home dates back to the early 1900's and some of the original characteristics have been left in tact. This is most assuredly Old World Charm meets Modern Convenience. One bedroom on the first floor attached to the

    Ellen Mallet

    30 Myrtle Ave, Pine Plains, NY 12567
  • /38

    $485,000 Open Sat 12PM - 2PM

    • 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
  • /20

    $1,250,000

    • 4 Beds
    • 2.5 Baths
    • 3,360 Sq Ft

    216 North Rd, Red Hook, NY 12571

    ?? 216 North Rd, Red Hook, NY 12571 Offered on 119 Acres – A Rare Hudson Valley Retreat Experience the best of country living on this stunning 119-acre estate bordering a state park, offering endless opportunities for outdoor recreation and peaceful privacy. This completely renovated 4-bedroom, 2-bath home combines modern comfort with the beauty of nature. Every detail has been updated — move-in

    Bill Flood Houlihan Lawrence Inc.

    216 North Rd, Red Hook, NY 12571
  • /50

    $8,475,000

    • 6 Beds
    • 7.5 Baths
    • 12,418 Sq Ft

    367 Prospect Hill Rd, Ancramdale, NY 12503

    First time on the market! This magnificent 170-acre Modern Adirondack-styled estate near Millbrook, designed by architect Lloyd Taft, features a main house and three elegant guest cabins. Built by a third-generation builder of camps in upstate New York and the Thousand Islands, the cabin serves as the centerpiece of the compound. Meticulously maintained and tailor-made for year-round recreation,

    George Langa Houlihan Lawrence Inc.

    367 Prospect Hill Rd, Ancramdale, NY 12503
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