2,886

Dutchess, NY Homes

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  • 1598 Jackson Corners Rd, Red Hook, NY 12571
    1598 Jackson Corners Rd, Red Hook, NY 12571
    1598 Jackson Corners Rd, Red Hook, NY 12571
    /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
  • 97 North Rd, Red Hook, NY 12571

    $250,000 Sold Apr 01, 2025

    • 1,248 Sq Ft
    • $200/SF
    • 77 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1951

    97 North Rd, Red Hook, NY 12571

    Utilized as a weekend retreat for decades, this two-bedroom, two-bathroom home is available for the first time in a long time. The house sits on 1.8 acres and is set back off the roadway and surrounded by trees for privacy. There are two garages and two more storage sheds . A large deck welcomes you to the front door. Centrally situated between Red Hook, Rhinebeck, Pine Plains, Millbrook and

    Richard Brenner Rich Brenner Realty, LLC

    97 North Rd, Red Hook, NY 12571
  • 235 Knob Hill Rd, Stanfordville, NY 12581
    235 Knob Hill Rd, Stanfordville, NY 12581
    235 Knob Hill Rd, Stanfordville, NY 12581
    /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
  • 3088 Church St, Pine Plains, NY 12567

    $307,500 Sold Mar 20, 2025

    • 2,328 Sq Ft
    • $132/SF
    • 43 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1872

    3088 Church St, Pine Plains, NY 12567

    Located at the edge of the town center on about a third of an acre, this 3 bedroom, 2 bathroom colonial style home is waiting for a fresh start. The side entrance from the driveway finds a mud room and laundry room. From there you’ll find a spacious kitchen attached to a nicely sized dining room. Pass through the center hall to a large living room adorned by a gas fireplace. The center hall

    Richard Brenner Rich Brenner Realty, LLC

    3088 Church St, Pine Plains, NY 12567
  • 617 Bean River Rd, Millerton, NY 12546
    617 Bean River Rd, Millerton, NY 12546
    617 Bean River Rd, Millerton, NY 12546
    /34

    $1,575,000

    • 3 Beds
    • 3 Baths
    • 3,833 Sq Ft

    617 Bean River Rd, Millerton, NY 12546

    Major Update! Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This

    Diana Bisselle William Pitt Sothebys Int Rlty

    617 Bean River Rd, Millerton, NY 12546
  • 0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503

    $1,975,000 Sold Mar 17, 2025

    • 4,144 Sq Ft
    • $477/SF
    • 428 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2000

    0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503

    The options are endless for this very special 120-acre property on a spectacular country road in beautiful Ancramdale, NY. The property, which has been a family compound for multiple generations, begins with a very long private driveway that leads to the original 1850's farmhouse and guest cottage overlooking a gorgeous 4+ acre pond. As you continue down the driveway, past lovely rolling hills,

    Neil Charles Neil Charles Real Estate, LLC

    0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503
    • 6 Sheldon Dr, Pine Plains, NY 12567
      6 Sheldon Dr, Pine Plains, NY 12567
      /2

      Est $436,813 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,310 Sq Ft

      6 Sheldon Dr, Pine Plains, NY 12567

      6 Sheldon Dr, Pine Plains, NY 12567
  • 540 Hicks Hill Rd, Stanfordville, NY 12581
    540 Hicks Hill Rd, Stanfordville, NY 12581
    540 Hicks Hill Rd, Stanfordville, NY 12581
    /38

    $579,000 Open Sun 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,269 Sq Ft

    540 Hicks Hill Rd, Stanfordville, NY 12581

    Charming 3-bedroom, 2.5-bathroom Colonial nestled on 5.58 private acres. Enjoy quiet moments on your wrap-around rocking chair front porch and take in picturesque views of Stissing Mountain. This inviting home features a spacious living room, formal dining room and an eat-in kitchen that flows into a comfortable family room perfect for gatherings. Step out from the family room onto a patio ideal

    Rita Longo Howard Hanna Rand Realty

    540 Hicks Hill Rd, Stanfordville, NY 12581
  • 348 Willow Glen Rd, Red Hook, NY 12571
    348 Willow Glen Rd, Red Hook, NY 12571
    348 Willow Glen Rd, Red Hook, NY 12571
    /29

    $840,000 Sold Mar 14, 2025

    • 2,092 Sq Ft
    • $402/SF
    • 58 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1968

    348 Willow Glen Rd, Red Hook, NY 12571

    This gorgeous A-frame—featured in both Dwell and Vogue magazines—combines countryside charm with mid-century modernism in the heart of the Hudson Valley. The Red Hook home sits on six wooded acres, around the corner from a natural swimming hole, yet only minutes away from the Taconic State Parkway. A welcoming, cottage-like exterior opens into a thoughtfully designed, architectural home

    Sarah Finch The Kinderhook Group, Inc.

    348 Willow Glen Rd, Red Hook, NY 12571
  • 729 Cold Spring Rd Unit 731, Stanfordville, NY 12581
    729 Cold Spring Rd Unit 731, Stanfordville, NY 12581
    729 Cold Spring Rd Unit 731, Stanfordville, NY 12581
    /43

    $2,495,000

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

    729 Cold Spring Rd Unit 731, Stanfordville, NY 12581

    Nestled at the end of a long private drive and surrounded by large estates and protected land, “The George” is a timeless 1798 farmhouse set on 7.2 serene acres in the bucolic heart of the Hudson Valley. With a private paddock, freshwater pond, and gently rolling lawns framed by mature trees, this historic estate offers the ultimate country retreat.The main house blends contemporary

    DOMINIQUE SHUMINOV William Pitt Sothebys Int Rlty

    729 Cold Spring Rd Unit 731, Stanfordville, NY 12581
  • 599 Bean River Rd, Millerton, NY 12546
    599 Bean River Rd, Millerton, NY 12546
    599 Bean River Rd, Millerton, NY 12546
    /3

    $335,000 Sold Jan 30, 2025

    • 1,296 Sq Ft
    • $258/SF
    • 53 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1950

    599 Bean River Rd, Millerton, NY 12546

    Set on a spacious 1.69-acre parcel with captivating farm and mountain views, 3 bedrooms and 2 full baths, this cozy home also includes a cozy wood-burning fireplace and hardwood floors throughout ground floor. The upper-level hosts a 2-bedroom loft space and a second full bath. With a little TLC, this property and location make it ideal for buyers looking to create their own dream home in a

    Christopher Virtuoso Keller Williams Realty HV Nort

    599 Bean River Rd, Millerton, NY 12546
  • 30 N Main St, Pine Plains, NY 12567
    30 N Main St, Pine Plains, NY 12567
    30 N Main St, 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
  • 21 Hamlet Ln, Red Hook, NY 12571

    $415,000 Sold Jan 17, 2025

    • 1,408 Sq Ft
    • $295/SF
    • 98 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1960

    21 Hamlet Ln, Red Hook, NY 12571

    Welcome to The Red Hook Retreat. An exquisite 2 bedroom split-level home set on just under 1 acre of lush, private land. Step inside to discover an inviting living room with wood burning fireplace and an open-concept kitchen and dining area, perfect for hosting memorable gatherings with family and friends. The versatile bonus room can easily be transformed into a third bedroom, complete with its

    Jessica Hill Real Broker NY LLC

    21 Hamlet Ln, Red Hook, NY 12571
    • 3094 Church St, Pine Plains, NY 12567
      3094 Church St, Pine Plains, NY 12567
      /2

      Est $324,692 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,250 Sq Ft

      3094 Church St, Pine Plains, NY 12567

      3094 Church St, Pine Plains, NY 12567
  • 3362 New York 199, Pine Plains, NY 12567
    3362 New York 199, Pine Plains, NY 12567
    3362 New York 199, 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
  • 3066 Church St, Pine Plains, NY 12567
    3066 Church St, Pine Plains, NY 12567
    3066 Church St, Pine Plains, NY 12567
    /16

    Sold Jan 13, 2025

    • 1,416 Sq Ft
    • 52 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1870

    3066 Church St, Pine Plains, NY 12567

    Personalize it to your taste, as much of the groundwork has been laid for an ideal home or business. This property is situated in the H-MS (Hamlet - Main Street Zone), a tranquil area governed by a 35 MPH speed limit. The yard is flat and inviting, featuring a detached garage and an enclosed space perfect for pets or gardening.

    Brad Rebillard Dutchess Country Realty, Inc.

    3066 Church St, Pine Plains, NY 12567
  • 387 Skunks Misery Rd, Millerton, NY 12546
    387 Skunks Misery Rd, Millerton, NY 12546
    387 Skunks Misery Rd, Millerton, NY 12546
    /32

    $2,495,000

    • 3 Beds
    • 3 Baths
    • 4,648 Sq Ft

    387 Skunks Misery Rd, Millerton, NY 12546

    Perched high above Millerton in the Hudson Valley, this exceptional 2020-built contemporary farmhouse estate commands 53± private acres with panoramic western views spanning the Catskills and Berkshire Mountain Range, including Mount Kaaterskill. Wide red oak hardwood floors unite the main level, where abundant natural light floods through expansive windows, creating an atmosphere of seamless

    Elyse Morris Elyse Harney Real Estate

    387 Skunks Misery Rd, Millerton, NY 12546
  • 102 Hall Hill Rd, Ancram, NY 12502

    $970,000 Sold Dec 23, 2024

    • 2,268 Sq Ft
    • $428/SF
    • 147 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1988

    102 Hall Hill Rd, Ancram, NY 12502

    Calling all barndominium lovers! Welcome to this income-producing horse boarding facility with indoor arena, large 14-stall barn, hay storage capacity, training round pen, 8-stall paddock/stall building, dog kennel, chicken coop, andpastures. Unique opportunity to own an equestrian property on 26 acres, with trail on the RoeJan Kill River. Off the beaten path and nicely nestled in a quiet

    Antoinette Caruso Stonewall Realty Group LLC

    102 Hall Hill Rd, Ancram, NY 12502
  • 60 County Route 7, Pine Plains, NY 12567
    60 County Route 7, Pine Plains, NY 12567
    60 County Route 7, Pine Plains, NY 12567
    /17

    $639,000

    • 3 Beds
    • 2 Baths
    • 896 Sq Ft

    60 County Route 7, Pine Plains, NY 12567

    ACCEPTED OFFER. Available: 7.5 lush acres on the Roe-Jan! A rustic-style late mid-century three-bedroom, two bath home sits in a beautifully landscaped property with nearly 300 feet of footage on the Roeliff Jansen Kill in Gallatin, New York. You approach this quiet and serene hideaway by a long a private drive through shady woods. The home, built by a local lumber dealer, provides a warm and

    David Norman Hall Houlihan Lawrence Inc.

    60 County Route 7, Pine Plains, NY 12567
  • 88 Friar Tuck Rd, Ancramdale, NY 12503
    88 Friar Tuck Rd, Ancramdale, NY 12503
    88 Friar Tuck Rd, Ancramdale, NY 12503
    /38

    $2,000,000 Sold Dec 19, 2024

    • 3,804 Sq Ft
    • $526/SF
    • 202 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 1880

    88 Friar Tuck Rd, Ancramdale, NY 12503

    Enjoy country living at its best in this1880 Victorian located down a quiet country lane in the Ancram area which is convenient to all the Berkshire's and surrounding areas have to offer. The home features generous size rooms with high ceilings. Enter through a large foyer area that opens into the kitchen with a built-in breakfast nook, viking stove for the serious chef and an adjacent cozy

    Ann Simmons Compass Greater NY, LLC d/b/a

    88 Friar Tuck Rd, Ancramdale, NY 12503
  • 1601 Route 199, Red Hook, NY 12571
    1601 Route 199, Red Hook, NY 12571
    1601 Route 199, Red Hook, NY 12571
    /25

    $430,000

    • 3 Beds
    • 2 Baths
    • 1,097 Sq Ft

    1601 Route 199, Red Hook, NY 12571

    Charming Renovated Ranch with Scenic Views and Endless Potential, l with extra additional side lot!! Welcome to this beautifully renovated ranch-style home offering 1,200 square feet of comfortable, single-level living. Featuring 3 spacious bedrooms and 2 full baths, this thoughtfully updated home boasts a functional and versatile layout with multiple private entrances—perfect for

    Jason Schobert eXp Realty

    1601 Route 199, Red Hook, NY 12571
  • 570 Bean River Rd, Pine Plains, NY 12567

    $2,200,000 Sold Dec 19, 2024

    • 4,207 Sq Ft
    • $523/SF
    • 377 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2023

    570 Bean River Rd, Pine Plains, NY 12567

    The approach to this spectacular contemporary barn-style home takes you up a long, winding private driveway past open fields & woods that are part of this special 22+ acre property. At the top of the hill, sits this incredibly private, recently completed, custom, stick built, 3-bedroom, 3.5-bath, contemporary home boasting approximately 4,000 sf of total square footage. This stunning home is

    Ann Stettner Neil Charles Real Estate, LLC

    570 Bean River Rd, Pine Plains, NY 12567
  • 3778 New York 82, Ancramdale, NY 12503
    3778 New York 82, Ancramdale, NY 12503
    3778 New York 82, Ancramdale, NY 12503
    /42

    $2,850,000

    • 3 Beds
    • 3.5 Baths
    • 4,247 Sq Ft

    3778 New York 82, Ancramdale, NY 12503

    An artist's delight, a gardener's dream and a naturalist's paradise. A thoughtfully designed and exceptionally well-built home set on 78 acres of woodlands and farmland with agricultural exemptions in place. This 4,250 SF architect designed home features multiple structures centered around a landscaped courtyard. Connected to the main home, by way of a covered portico, is a private guest suite

    Michael Stasi Corcoran Country Living

    3778 New York 82, Ancramdale, NY 12503
  • Unlisted Address

    $285,000 Sold Dec 19, 2024

    • 750 Sq Ft
    • $380/SF
    • 52 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1950

    Unlisted Address

    Fully updated and renovated cottage sitting back on a long beautiful driveway on 3 acres this modern NYC loft style house is perfect for someone who loves privacy and a scenic view. This property was originally part of a winery with limitless potential for landscaping and views. Brand new vinyl siding, roof, floors, windows, quartz countertops, appliances, tile work and more this is move in

    Lorraine Little LITTLE LORRAINE ML

    Unlisted Address
  • 66 Ryan Rd, Pine Plains, NY 12567
    66 Ryan Rd, Pine Plains, NY 12567
    66 Ryan Rd, Pine Plains, NY 12567
    /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
  • 1420 Route 83, Pine Plains, NY 12567
    1420 Route 83, Pine Plains, NY 12567
    1420 Route 83, Pine Plains, NY 12567
    /33

    $407,500 Sold Dec 18, 2024

    • 2,456 Sq Ft
    • $166/SF
    • 55 Days On Market
    • 5 Beds
    • 2.5 Baths

    1420 Route 83, Pine Plains, NY 12567

    Surrounded by rolling hills in the Pine Plains hamlet of Shekomeko sits this beautiful, spacious colonial house with preserved original detail and tasteful recent updates that fuse a modern feeling with original character. Built in 1865, the home has 5 bedrooms and 2.5 baths, a large living room, separate family room and a formal dining area. The kitchen was recently updated with stainless

    Adam Ecker ECKER ADAM D

    1420 Route 83, Pine Plains, NY 12567
  • 367 Prospect Hill Rd, Ancramdale, NY 12503
    367 Prospect Hill Rd, Ancramdale, NY 12503
    367 Prospect Hill Rd, Ancramdale, NY 12503
    /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
  • 182 Silvernails Rd, Pine Plains, NY 12567
    182 Silvernails Rd, Pine Plains, NY 12567
    182 Silvernails Rd, Pine Plains, NY 12567
    /36

    $2,578,000 Sold Dec 17, 2024

    • 4,724 Sq Ft
    • $546/SF
    • 313 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 1980

    182 Silvernails Rd, Pine Plains, NY 12567

    Fly into this private, hilltop country estate with its own airstrip. This five bedroom, five and one half bath home has stunning bucolic views to Stissing Mountain and provides a layout that has an airy and elegant ambiance. The cathedral living room is centered around a soaring stone fireplace and leads to a cozy library and the formal dining room. Top of the line appliances, marble countertops,

    Paula Redmond Corcoran Country Living - Mill

    182 Silvernails Rd, Pine Plains, NY 12567

Showing Results 41 - 80, Page 2 of 18

New York Dutchess County Pine Plains

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