Pleasant Valley, NY Homes for Sale

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  $499,000

  $51K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,738 Sq Ft

  8 Trillium Rd, Pleasant Valley, NY 12569

  Welcome to this amazing weekend retreat or year-round sanctuary, privately set on 4.71 beautiful acres with a peaceful babbling brook. Surrounded by nature’s beauty, this special property offers the perfect blend of privacy, comfort, and tranquility. Step inside to a dramatic living room featuring a vaulted ceiling, a wall of glass with southern exposure, and an abundance of natural light. The

  Blake Michaud BHHS Hudson Valley Properties

  8 Trillium Rd, Pleasant Valley, NY 12569
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  $1,195,000

  $180K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,820 Sq Ft

  101 Drake Rd, Pleasant Valley, NY 12569

  Historic Barn Conversion Meets Modern Luxury in the Hudson Valley Tucked away along a quiet country road in Pleasant Valley, this extraordinary estate offers a rare opportunity to own a meticulously restored 19th-century barn conversion that seamlessly blends historic character with modern luxury. Originally two separate barns, the property has been thoughtfully reimagined into a one-of-a-kind

  Jake Garay Serhant LLC

  101 Drake Rd, Pleasant Valley, NY 12569
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  $179,900

  • Land
  • 5.04 Acres
  • $35,694 per Acre

  0 Creek Rd Unit KEY981346, Pleasant Valley, NY 12569

  Build your dream home on this beautiful 5-acre Board of Health approved parcel in Pleasant Valley, where privacy, natural beauty, and opportunity come together. This exceptional property offers a rare chance to create a custom home or private retreat in a peaceful Hudson Valley setting.Surrounded by mature trees and scenic countryside, the land provides the perfect backdrop for your vision.

  Robert Villone RE/MAX Classic Realty

  0 Creek Rd Unit KEY981346, Pleasant Valley, NY 12569
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  $699,999

  • 4 Beds
  • 2.5 Baths
  • 2,434 Sq Ft

  185 Rombout Rd, Pleasant Valley, NY 12569

  STOP THE SEARCH! THIS IS THE ONE! INCREDIBLE PROPERTY! ENTERTAINER'S DREAM HOME! Welcome to your own private Hudson Valley retreat, where every day feels like a vacation. Tucked away at the end of a long private driveway and nestled on just over six beautifully wooded acres in the highly sought after Arlington School District, this exceptional Colonial offers the perfect balance of privacy,

  Frank Muccari Cronin & Company Real Estate

  185 Rombout Rd, Pleasant Valley, NY 12569
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  /23

  $799,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,166 Sq Ft

  991 Freedom Rd, Pleasant Valley, NY 12569

  TO BE BUILT – The Vanderbilt Model Colonial on Over 3 Acres!This stunning 4-bedroom, 2.5-bath colonial offers the perfect blend of elegance and functionality. The thoughtfully designed main level features a formal living room and dining room, a spacious family room that showcases a gas fireplace and a wall of windows, seamlessly opening to the kitchen with quartz counters, a center island,

  John Gabriel Jr KW MidHudson

  991 Freedom Rd, Pleasant Valley, NY 12569
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  $1,495,000

  Open Sat 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 3,920 Sq Ft

  49 Barkit Kennel Rd, Pleasant Valley, NY 12569

  Rare and extraordinary custom built private estate nestled on 43 private acres in the heart of Pleasant Valley. Surrounded by rolling woodlands and breathtaking natural beauty, this exceptional residence offers an unparalleled blend of timeless elegance, refined craftsmanship, and resort-style living. Whether you're seeking a luxurious full-time residence, an executive retreat, or a secluded

  Justin Phillips United RE Hudson Valley Edge

  49 Barkit Kennel Rd, Pleasant Valley, NY 12569
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  $439,000

  • 4 Beds
  • 3 Baths
  • 1,764 Sq Ft

  179 Hibernia Rd, Salt Point, NY 12578

  Welcome to Your Private Creekside Oasis in Pleasant Valley, NY - 4 Bedrooms | 3 Full Baths | 1 Acre | w/Mother-Daughter Suite. Set far back from the road, this beautifully maintained 4-bedroom, 3-full-bath home offers the perfect blend of total privacy, natural beauty, and flexible living space. Minutes from Millbrook, Pleasant Valley, Hyde Park, Rhinebeck and many other Hudson Valley hot-spots.

  Christopher Virtuoso KW Hudson Valley North

  179 Hibernia Rd, Salt Point, NY 12578
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  $699,000

  • 4 Beds
  • 2.5 Baths
  • 3,106 Sq Ft

  100 Rockledge Dr, Pleasant Valley, NY 12569

  Roof is brand new. Perfectly positioned just two miles from the Taconic State Parkway, this exceptional home offers an easy commute north or south while being only five minutes from Overlook Elementary School and nine minutes from Arlington High School.Designed with both comfort and functionality in mind, the home features hardwood floors and elegant crown molding throughout, hydro-air

  Peggy Santamorena Houlihan Lawrence Inc.

  100 Rockledge Dr, Pleasant Valley, NY 12569
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  $695,000

  $100K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,019 Sq Ft

  41 Meddaugh Rd, Pleasant Valley, NY 12569

  Welcome to 41 Meddaugh Road, a beautifully transformed 4 bedroom, 2.5 bathroom contemporary home with Hudson Valley historic farmhouse charm. Setback from the road, this turnkey home is sited on 1.84 acres and has undergone an extensive ground-up renovation. This property was previously under contract. The buyer was unable to close due to a contingency on their own home sale -- not any issue with

  Kyle Irwin Corcoran Country Living

  41 Meddaugh Rd, Pleasant Valley, NY 12569
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  $1,100,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 4,300 Sq Ft

  129 Clinton Corners Rd, Salt Point, NY 12578

  Set behind a sweeping driveway canopied by pear trees in bloom, this extraordinary post-and-beam contemporary is a study in what privacy truly looks like — 18.5 acres of curated landscape, forest trails, and open sky, ten minutes from the Taconic State Parkway. The architecture announces itself immediately: soaring 25-foot cathedral ceilings, a commanding central stone fireplace, and grand

  Ryan Arket Compass Greater NY, LLC

  129 Clinton Corners Rd, Salt Point, NY 12578
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  $724,900

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  394 Smith Rd, Hyde Park, NY 12538

  Welcome to 394 Smith Rd. A sprawling Mid-Century Ranch on Nearly 10 Acres with Pond & Panoramic Views. Set on nearly 10 private acres, this picturesque sprawling ranch offers true one-level living with breathtaking 360-degree views, including stunning sunrises and sunsets. Tucked back from the road and elevated for maximum privacy, this special property blends natural beauty and charm.The

  LISA WOHLMUTH KW MidHudson

  394 Smith Rd, Hyde Park, NY 12538
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  $549,500

  Open Sun 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 2,469 Sq Ft

  34 Contour Ln, Salt Point, NY 12578

  Welcome to 34 Contour Lane. Situated on a small cul-de-sac and nestled on almost 4 private acres in the heart of Salt Point, equidistant between the Villages of Rhinebeck and Millbrook. This beautifully maintained 4-bedroom, 2.5-bath Colonial offers the perfect blend of timeless charm, modern updates, and peaceful country living. Offering almost 2500 finished SQFT, this home welcomes you with

  Justin LaFalce KW MidHudson

  34 Contour Ln, Salt Point, NY 12578
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  /2

  $119,000

  • Land
  • 2.86 Acres
  • $41,608 per Acre

  5 Bower Rd, Poughkeepsie, NY 12603

  2.86 Acre lot with board of health approval for a 4 bedroom home. Perfect to build your dream home, bring your own builder or use ours! We can help and assist the first time homebuyer build their dream home through the whole process.

  Bliss Voutsinas Hillside Realty & Development

  5 Bower Rd, Poughkeepsie, NY 12603

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