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Pine Plains, NY Houses for Sale

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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
  • /26

    $4,250,000

    • 6 Beds
    • 4 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
  • /20

    $410,000

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

    73 Meusel Rd, Pine Plains, NY 12567

    A large and roomy home is for sale in the charming Village of Pine Plains, NY. Situated in a residential neighborhood with views of the surrounding hills, the home sits well back from the road on a corner lot. On the first floor are two living rooms, a dining room, an eat-in kitchen, a powder room and a mudroom. Off the kitchen is a partially finished three season room and a deck. Upstairs is the

    David Norman Hall Houlihan Lawrence, Inc

    73 Meusel Rd, Pine Plains, NY 12567
  • /18

    $3,995,000

    • 3 Beds
    • 2 Baths
    • 5,000 Sq Ft

    3362 New York 199, Pine Plains, NY 12567

    To-Be-Built Luxury Estate with Infinity Pool & Panoramic Catskill Views – Pine Plains, NY. Elevated high above the valley floor with sweeping, unobstructed Catskill Mountain views, this to-be-built custom estate is a rare opportunity in the heart of the Hudson Valley. Set on an extraordinary piece of land—offering total privacy and dramatic natural beauty—this 5,000+ square foot residence is

    Michael Lund Corcoran Country Living

    3362 New York 199, 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
  • /44

    $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 9.6 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white clapboard

    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

    $489,000

    • 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
  • /29

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    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 ready and designed for year-round

    Bill Flood Houlihan Lawrence, Inc.

    216 North Rd, Red Hook, NY 12571
  • /22

    $315,000

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    84 North Rd, Red Hook, NY 12571

    Early 1800s Colonial loved and enjoyed by same family for over 60 years. Looking for a visionary person to restore to former glory. Many original details still intact include hand hewn beams, wide board floors, cobble fireplace in Living room etc. 3 plus Bedrooms, 1 Full Bath with possible 2nd on upper level. Large country Kitchen, Formal Dining Room with Woodstove Hook Up and access to massive

    Catherine Mondello Mondello Upstate Properties

    84 North Rd, Red Hook, NY 12571
  • /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
  • /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
  • /10

    $174,800

    • 4 Beds
    • 2.5 Baths
    • 3,444 Sq Ft

    245 Hicks Hill Rd, Stanfordville, NY 12581

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

    Ernie Acampora River Realty Services, Inc.

    245 Hicks Hill Rd, Stanfordville, NY 12581
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