20

Pine Plains, NY Homes for Sale with AC

Section Image Section Image
  • /50

    $3,995,000

    • 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
  • /28

    $475,000

    • 3 Beds
    • 1 Bath
    • 1,600 Sq Ft

    3807 Route 199, Pine Plains, NY 12567

    Nestled between the villages of Pine Plains and Millerton, in the hamlet of Pulver's Corners, this single-level home exudes country charm and a cozy vibe. The backyard features a stone patio surrounded by perennial and vegetable gardens, with a picturesque view of a pasture. Morning sunlight beautifully illuminates the rolling hills and farmland beyond. Inside, the home boasts natural wood

    Agent Photo

    Brad Rebillard

    DUTCHESS COUNTRY REALTY INC. M

    (518) 941-8819

    3807 Route 199, Pine Plains, NY 12567
  • /26

    $379,000

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    48 Woodside St, Pine Plains, NY 12567

    Whether for starting out retirement or weekend use, 48 Woodside Street is an efficient, move-in-ready home. Pine Plains offers a number of attractions from fine dining at the Stissing House, or a relaxing kayak paddle on Thompson Pond. Nearby hiking trails offer options such as the Stissing Fire Tower, a challenging local favorite, and the Thompson Preserve an easy woodland stroll around a

    Agent Photo

    Brad Rebillard

    Dutchess Country Realty, Inc.

    (518) 662-5219

    48 Woodside St, Pine Plains, NY 12567
  • /7

    $1,995,000

    • 3 Beds
    • 2.5 Baths
    • 2,267 Sq Ft

    820 Cold Spring Rd, Stanfordville, NY 12581

    (To be built) Perfectly sized upstate retreat, Zenith integrates seamlessly with its bucolic setting, minutes from Rhinebeck village. The low pitched angled roof planes intersect in the residence’s great room with clerestory windows to flood the living spaces with light.Zenith is sited on 7 private primarily wooded acres. The residence showcases interiors with natural textures and a

    DOUG MAXWELL Upstate Modernist

    820 Cold Spring Rd, Stanfordville, NY 12581
  • /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
  • /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
  • /45

    $4,950,000

    • 5 Beds
    • 5.5 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
  • /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 William Pitt Sotheby's Interna

    255 Mill Hill Rd, Pine Plains, NY 12567
  • /30

    $595,000

    • 4 Beds
    • 2.5 Baths
    • 3,180 Sq Ft

    30 N Main St, Pine Plains, NY 12567

    Grand 1880 Colonial Estate Sale - Historic Fixer-Upper with Original Features and Garden Oasis Near Town CenterThis rare 1880 Grand Colonial is a dream opportunity for restoration enthusiasts and anyone searching for a historic fixer-upper near the heart of town. Situated on a flat, tree-lined lot, this estate sale is being sold as is and is filled with authentic charm—from original

    Arleen Shepley Elyse Harney Real Estate

    30 N Main St, Pine Plains, NY 12567
  • /30

    $925,000

    • 4 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    1388 Route 83, Pine Plains, NY 12567

    This c. 1880 three-story farmhouse seamlessly blends historic charm with modern luxury, meticulously cared for and thoughtfully curated to offer both timeless elegance and contemporary comfort.Step inside and be greeted by the inviting, light-filled living room. This spacious area exudes classic sophistication, centered around a warming wood-burning fireplace and boasting large windows that

    Jill Rose Houlihan Lawrence Inc.

    1388 Route 83, Pine Plains, NY 12567
  • /36

    $995,000

    • 4 Beds
    • 3 Baths
    • 3,980 Sq Ft

    235 Knob Hill Rd, Stanfordville, NY 12581

    Nestled on 13 private acres of lush landscapes, meandering trails and impressive stone walls, you will find two very special vintage homes, outdoor sauna and shower plus small artist studio. Built in 1850 this two bedroom farmhouse combines historical character with contemporary amenities, featuring gleaming wood and wide board floors beamed ceiling, stone fireplace, central air and a gourmet

    Jeannine Simmons Corcoran Country Living

    235 Knob Hill Rd, Stanfordville, NY 12581
  • /43

    $899,000

    • 5 Beds
    • 3.5 Baths
    • 2,714 Sq Ft

    198 Sigler Rd, Pine Plains, NY 12567

    This architect designed and custom built passive solar home and guest house is sited privately on 17.90 acres with panoramic views of the of the eastern valley plains to Stissing Mountain and beyond. The tree lined driveway leads you to both houses that sit high on the land, facing south over looking the property fields & pond. Perfectly sited for the passive solar design and the solar panel

    Kimberly Baker BHHS Hudson Valley Properties

    198 Sigler Rd, Pine Plains, NY 12567
  • /39

    $415,000

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    107 Near Rd, Red Hook, NY 12571

    A true Hudson Valley treasure! Step into this enchanting 1934 Hudson Valley home, where vintage charm meets modern sophistication. Set on nearly 2 peaceful acres, this 2-bedroom, 2-bath retreat features a cozy open floor plan with an inviting fireplace/woodstove, multiple skylights, exposed beams, incredible architectural lines, and beautiful Doug fir wood floors. Offering a perfect blend of

    Margaret Niekrewicz Margaret Mondello Real Estate

    107 Near Rd, Red Hook, NY 12571
  • /49

    $699,000

    • 7 Beds
    • 5 Baths

    80 County Route 7, Pine Plains, NY 12567

    This beautifully updated legal 2-family home seamlessly blends vintage charm with modern convenience, offering exceptional flexibility for multigenerational living, rental income, or guest accommodations. Located just 7 minutes from Pine Plains Village and set on a scenic lot with sweeping countryside views and a neighboring 200-acre farm, the property features meticulously maintained grounds,

    Margaret Niekrewicz Margaret Mondello Real Estate

    80 County Route 7, Pine Plains, NY 12567
  • /16

    $539,000

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

    284 Hall Hill Rd-Stop # 18, Ancram, NY 12502

    A ''Real Deal'' log home in Ancram, New York. This listing has been reconfigured to include a separate 3 acre building parcel, across the private dead-end road. Read below the importance of this added acreage. The home has 3 BR, 2 BA, and is 1768 sf. It is surrounded by woods and meadows. There is a brick fireplace, wood stove, open floor plan, and deck out back. Fiber-optic

    Lindsay Lebrecht Copake Lake Realty Corp.

    284 Hall Hill Rd-Stop # 18, Ancram, NY 12502
  • /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
  • /37

    $1,595,000

    • 4 Beds
    • 3 Baths
    • 3,980 Sq Ft

    235 Knob Hill Rd, Stanfordville, NY 12581

    Nestled on 56 private acres of lush landscapes, meandering trails and impressive stone walls, you will find two very special vintage homes, sizeable barn, outdoor sauna and shower plus small artist studio. Built in 1850 this two bedroom cottage combines historical character with contemporary amenities, featuring gleaming wood and wide board floors, beamed ceilings, stone fireplace, central air

    Jeannine Simmons Corcoran Country Living

    235 Knob Hill Rd, Stanfordville, NY 12581
  • /35

    $18,750,000

    • 11 Beds
    • 7.5 Baths
    • 7,500 Sq Ft

    461 Silvernails Rd, Pine Plains, NY 12567

    Ingadi, the Zulu word for garden, is a true legacy compound all set within 127 acres of pristine land with a total of 11 bedrooms across four distinct residential structures. A magical journey of the senses where the Roeliff Jansen Kill and the Shekomeko Creek merge, ensuring sustainability while creating one of the most spiritually powerful and visually stunning experiences in the Hudson Valley.

    Byron Anderson Compass Greater NY, LLC

    461 Silvernails 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
  • /12

    $509,000

    • 4 Beds
    • 1.5 Baths
    • 3,072 Sq Ft

    7786 S Main St, Pine Plains, NY 12567

    You wanted charm? You got it! This vintage 1903 village home in Pine Plains, NY formerly served as both the town pharmacy and library, and many of the bookshelves and all the quaint apothecary drawers remain intact. The large 3000sq foot home on a nicely landscaped yard of nearly a half an acre is filled with period details: wooden moldings, original door knobs and intricate iron hardware, a

    David Norman Hall Houlihan Lawrence Inc.

    7786 S Main St, Pine Plains, NY 12567
How to Buy a Home How to Finance a Home How to Sell a Home