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Pine Plains, NY Homes for Sale with Acreage

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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
  • /4

    $120,000

    • Land
    • 5.02 Acres
    • $23,904 per Acre

    0 Mount Ross Rd, Pine Plains, NY 12567

    Every once in a while, an exceptional opportunity like this turns up. Located in rural Pine Plains this 5.02-acres is a pair of vacant building lots that offers privacy and serenity. These two contiguous parcels are completely wooded and accessed via a shared driveway. Your dream home is only limited by your imagination these parcels will invigorate that imagination. The Town center and the

    Agent Photo

    Larry Havens

    Havens Real Estate

    (518) 672-6676

    0 Mount Ross Rd, Pine Plains, NY 12567
  • /24

    $3,600,000

    • Land
    • 228.91 Acres
    • $15,727 per Acre

    0 Skunks Misery Rd Unit KEY860535, Pine Plains, NY 12546

    Sensational vistas of the stunning and unspoiled countryside extending to the Taconic's to the East and from a hidden knoll with an elevation of 1,250' there is a magnificent private setting with incredible Catskill views. The main parcel of 157 acres is offered for the first time in generations and that parcel adjoins a 71.5-acre parcel, this was a family owned and operated farm. Both properties

    Agent Photo

    Larry Havens

    Havens Real Estate

    (518) 676-2868

    0 Skunks Misery Rd Unit KEY860535, Pine Plains, NY 12546
  • /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
  • /5

    $140,000

    • Land
    • 1.5 Acres
    • $93,333 per Acre

    25 Five Roses E, Ancram, NY 12502

    Ready to build, this 1.5-acre parcel is located on a peaceful country road in the scenic town of Ancram, Columbia County, New York. Board of Health approval is already in place for a four-bedroom residence, saving valuable time in the building process. The property is well-prepared with an installed septic system, existing well, driveway, and underground electric service run from the road to a

    Richard Brenner RICH BRENNER REALTY LLC

    25 Five Roses E, Ancram, NY 12502
  • /31

    $549,000

    • 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
  • /7

    $139,000

    • Land
    • 4.24 Acres
    • $32,783 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. Newly renovated home on North. Adjoining 8 acre vacant lot to the South available for 199,000. Owner financing possible.

    David Birch Barns & Farms Realty, LLC

    620 Bean River Rd, 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
  • /36

    $1,499,000

    • 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
  • /7

    $145,000

    • Land
    • 3.45 Acres
    • $42,029 per Acre

    66 Ryan Rd, Pine Plains, NY 12567

    Build your dream home in the heart of Pine Plains, surrounded by nature, history, and vibrant Hudson Valley living, on this exceptional 3.45 Acre elevated homesite, Board of Health approved for a 4-bedroom residence, with sweeping views of majestic Stissing Mountain. This remarkable parcel offers the perfect blend of tranquility, natural beauty, and convenience, presenting a rare opportunity to

    Vida Odescalchi Legacy Land & Homes LLC

    66 Ryan Rd, Pine Plains, NY 12567
  • /10

    $213,750

    • 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
  • /21

    $255,000

    • 3 Beds
    • 2 Baths
    • 1,037 Sq Ft

    22-28 Ryan Rd, Pine Plains, NY 12567

    Looking for a piece of property for a great low price? Looking for two homes for the price of one? Looking for a good-sized plot of land? Here is a great opportunity for you to acquire one manufactured home, and one mobile home, both on the same plot of land with 2.30 acres! Investors will consider this property for rental income or tear-down and rebuild. Currently, the main manufactured home has

    Jorge Lugo Real Broker NY LLC

    22-28 Ryan Rd, Pine Plains, NY 12567
  • /15

    $1,995,000

    • Land
    • 150.48 Acres
    • $13,258 per Acre

    1533-1539 Route 83, Pine Plains, NY 12567

    Discover a rare 150-acre estate in one of the Hudson Valley’s most coveted farmland corridors. This property offers a private building site accessed by a scenic driveway and showcases the best of Hudson Valley living where nature meets luxury. Enjoy panoramic views of protected farmland, Shekomeko Creek, and wooded mountains. Surrounded by conservation land, this estate ensures lasting privacy

    John Panzer Elyse Harney Real Estate

    1533-1539 Route 83, Pine Plains, NY 12567
  • /3

    $104,000

    • Land
    • 4 Acres
    • $26,000 per Acre

    Knob Hill Rd N Knob Hill Rd, Stanfordville, NY 12581

    Beautiful Lot. Located in an established residential area in the town of Milan. Surrounded by well maintained homes. Minutes to Taconic State Parkway for easy commute. Terrain is partially cleared and partially wooded.Topography is level with some sloping. There is a driveway roughed in.

    Peggy Santamorena Houlihan Lawrence Inc.

    Knob Hill Rd N Knob Hill Rd, Stanfordville, NY 12581
  • /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
  • /15

    $389,000

    • 2 Beds
    • 2 Baths
    • 1,336 Sq Ft

    618 Bean River Rd, Pine Plains, NY 12567

    PINE PLAINS 1400 SF 2BR/2BA RANCH with new well on 7+ acres between Millerton and Pine Plains Village on quiet road off Route 199. Subdividable or combine with 8 acre approved building lot for Family Compound for 525,000. Additional adjoining 4 acre building lot available for 100,000 at package price. Terms available with substantial downpayment.

    David Birch Barns & Farms Realty, LLC

    618 Bean River Rd, Pine Plains, NY 12567
  • /47

    $2,290,000

    • 6 Beds
    • 5 Baths
    • 3,352 Sq Ft

    729 Cold Spring Rd Unit 731, Stanfordville, NY 12581

    A Storied 1798 Farmhouse Between Millbrook & Rhinebeck Set at the end of a long, graceful gravel drive and surrounded by large estates and protected land, The George is a timeless 1798 farmhouse quietly nestled on 7.2 serene acres in the heart of the Hudson Valley. Beautifully framed by towering old-growth trees, gently rolling lawns, and a freshwater pond, this historic property offers a rare

    DOMINIQUE SHUMINOV William Pitt Sothebys Int Rlty

    729 Cold Spring Rd Unit 731, Stanfordville, NY 12581
  • /25

    $869,900

    • 5 Beds
    • 3.5 Baths
    • 5,650 Sq Ft

    19 Friendship Ln, Red Hook, NY 12571

    Welcome to your private oasis and come enjoy this 3 bedroom 2.5 bath Colonial situated on 5 plus acres. The home also features an in law unit above the garage which has 2 additional bedrooms, a full bathroom, a galley kitchen and open living room. The home is very close to the Taconic State Parkway and US Rte 199 making it an easy drive to anywhere. The town of Red Hook boasts vibrant shops and

    Jeffery Dolfinger Century 21 Hudson Valley Rlty.

    19 Friendship Ln, Red Hook, NY 12571
  • /10

    $199,000

    • Land
    • 16 Acres
    • $12,438 per Acre

    0 New York 199, Stanfordville, NY 12581

    Priced to sell! What a beautiful destination for your dream home or summer get-a-way. So close to everything yet secluded.nLand has a 500' driveway professionally installed. 4 inches crushed stone edges with larger stone for proper drainage. Land backs up to 120 acres of state land. There is a small babbling brook that can be diverted if needed. 2 possible building sites had been are located on

    MARIE MONROE BHHS Hudson Valley Properties

    0 New York 199, Stanfordville, NY 12581
  • /37

    $1,225,000

    • 4 Beds
    • 2 Baths
    • 1,888 Sq Ft

    174 County Route 11, Pine Plains, NY 12567

    Expansive 55+ Acre Multi-Home Compound. A rare opportunity to own a one-of-a-kind compound set on 57.44 private, picturesque acres—ideal for multi-generational living or a unique investment. The main residence offers 1,888 square feet of rustic charm and comfort, featuring 4 bedrooms and 2 full baths. Enjoy cozy evenings in the living room with pegged oak floors, pine paneling, and a classic

    Paula Redmond Corcoran Country Living - Mill

    174 County Route 11, Pine Plains, NY 12567
  • /47

    $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

    OLIVER BROWN Houlihan Lawrence Inc.

    1515-1517 County Road 83, Pine Plains, NY 12567
  • /13

    $4,950,000

    • 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

    Michael Lund Corcoran Country Living

    3362 New York 199, Pine Plains, NY 12567
  • /7

    $290,000

    • Land
    • 68.33 Acres
    • $4,244 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 have been done on a potential lower building site. A level area at a higher elevation could offer even more privacy and ridgeline views. Roughed-in driveway is in place, so you're well on your way to building a home that's tailored exactly to your

    Jeffries Blackerby Houlihan Lawrence Inc.

    000 New York 82, Pine Plains, NY 12567
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