4,497

Pleasant Valley, NY Homes

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  • 103 Hibernia Heights Dr, Salt Point, NY 12578

    $450,000

    Sold Oct 08, 2025

    103 Hibernia Heights Dr, Salt Point, NY 12578

    • 3 Beds
    • 1 Bath
    • 1,388 Sq Ft
    • Built 1982

    Last Sold Summary

    • $324/SF
    • 86 Days On Market

    Current Estimated Value $456,721

    Last Listing Agent Thomas Hennerty

    103 Hibernia Heights Dr, Salt Point, NY 12578
  • 8 Trillium Rd, Pleasant Valley, NY 12569
    8 Trillium Rd, Pleasant Valley, NY 12569
    8 Trillium Rd, Pleasant Valley, NY 12569
    /32

    $550,000

    • 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
  • 63 Parksville Rd, Pleasant Valley, NY 12569

    $390,000

    Sold Mar 31, 2026

    63 Parksville Rd, Pleasant Valley, NY 12569

    • 4 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1962

    Last Sold Summary

    • 2% Below List Price
    • $271/SF
    • 38 Days On Market

    Current Estimated Value $399,233

    Last Listing Agent STEVEN WROBEL JR. Serhant LLC

    63 Parksville Rd, Pleasant Valley, NY 12569
  • 101 Drake Rd, Pleasant Valley, NY 12569
    101 Drake Rd, Pleasant Valley, NY 12569
    101 Drake Rd, Pleasant Valley, NY 12569
    /47

    $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
  • 33 Whiteford Dr, Pleasant Valley, NY 12569

    $495,000

    Sold Sep 09, 2025

    33 Whiteford Dr, Pleasant Valley, NY 12569

    • 3 Beds
    • 2 Baths
    • 1,712 Sq Ft
    • Built 1964

    Last Sold Summary

    • 1% Above List Price
    • $289/SF
    • 102 Days On Market

    Current Estimated Value $496,338

    Last Listing Agent Ann Scarano Realty Center Hudson Valley

    33 Whiteford Dr, Pleasant Valley, NY 12569
  • 88 Rymph Rd, Pleasant Valley, NY 12569
    88 Rymph Rd, Pleasant Valley, NY 12569
    88 Rymph Rd, Pleasant Valley, NY 12569
    /28

    $450,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,760 Sq Ft

    88 Rymph Rd, Pleasant Valley, NY 12569

    A peaceful ranch across from a working orchard, with all the big-ticket updates done. Few homes in this price range offer the same combination of comfort, convenience, and long-term value. Set on a level acre directly across from a working apple orchard, 88 Rymph Road brings open skies, seasonal orchard views, and genuine quiet to your everyday backdrop, all while staying just minutes from

    Anthony Flores Upstate Down

    88 Rymph Rd, Pleasant Valley, NY 12569
  • 38 Marshall Rd, Hyde Park, NY 12538

    $325,000

    Sold Feb 24, 2026

    38 Marshall Rd, Hyde Park, NY 12538

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1965

    Last Sold Summary

    • $339/SF
    • 63 Days On Market

    Current Estimated Value $341,822

    Last Listing Agent STEVEN WROBEL JR. Serhant LLC

    38 Marshall Rd, Hyde Park, NY 12538
  • 0 Creek Rd Unit KEY981346, Pleasant Valley, NY 12569
    0 Creek Rd Unit KEY981346, Pleasant Valley, NY 12569
    0 Creek Rd Unit KEY981346, Pleasant Valley, NY 12569
    /4

    $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
  • 29 Mcallister Dr, Pleasant Valley, NY 12569

    $475,000

    Sold May 27, 2026

    29 Mcallister Dr, Pleasant Valley, NY 12569

    • 3 Beds
    • 1.5 Baths
    • 1,701 Sq Ft
    • Built 1956

    Last Sold Summary

    • $279/SF
    • 59 Days On Market

    Current Estimated Value $468,166

    Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

    29 Mcallister Dr, Pleasant Valley, NY 12569
  • 991 Freedom Rd, Pleasant Valley, NY 12569
    991 Freedom Rd, Pleasant Valley, NY 12569
    991 Freedom Rd, Pleasant Valley, NY 12569
    /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
  • 57 Whiteford Dr, Pleasant Valley, NY 12569

    $508,000

    Sold Jul 08, 2025

    57 Whiteford Dr, Pleasant Valley, NY 12569

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Above List Price
    • $318/SF
    • 41 Days On Market

    Current Estimated Value $535,716

    Last Listing Agent Susan Feit BHHS Hudson Valley Properties

    57 Whiteford Dr, Pleasant Valley, NY 12569
  • 34 Contour Ln, Salt Point, NY 12578
    34 Contour Ln, Salt Point, NY 12578
    34 Contour Ln, Salt Point, NY 12578
    /38

    $550,000

    $49K PRICE DROP
    • 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
  • 4 Mcallister Dr, Pleasant Valley, NY 12569

    $452,100

    Sold Jun 30, 2026

    4 Mcallister Dr, Pleasant Valley, NY 12569

    • 4 Beds
    • 2.5 Baths
    • 1,988 Sq Ft
    • Built 1964

    Last Sold Summary

    • 8% Below List Price
    • $227/SF
    • 219 Days On Market

    Current Estimated Value $454,268

    Last Listing Agent Kaye Saglibene

    4 Mcallister Dr, Pleasant Valley, NY 12569
  • 316 Forest Valley Rd, Pleasant Valley, NY 12569
    316 Forest Valley Rd, Pleasant Valley, NY 12569
    316 Forest Valley Rd, Pleasant Valley, NY 12569
    /39

    $574,900

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    316 Forest Valley Rd, Pleasant Valley, NY 12569

    Welcome to this beautifully maintained Colonial, proudly offered by its original owner and set on 1.43 private acres with an exceptional backyard retreat in the Valley Dale area. Combining timeless charm with thoughtful updates, this 4-bedroom, 2.5-bath home is designed for comfortable everyday living and effortless entertaining. The inviting living room features hardwood floors and a classic

    Bonnie Massa BHHS Hudson Valley Properties

    316 Forest Valley Rd, Pleasant Valley, NY 12569
  • 1824 Route 44, Pleasant Valley, NY 12569

    $220,000

    Sold Apr 15, 2026

    1824 Route 44, Pleasant Valley, NY 12569

    • 1 Bed
    • 1 Bath
    • 708 Sq Ft
    • Built 1910

    Last Sold Summary

    • 10% Above List Price
    • $311/SF
    • 37 Days On Market

    Current Estimated Value $214,791

    Last Listing Agent Jennifer Amicucci

    1824 Route 44, Pleasant Valley, NY 12569
  • 44 Eleanor Dr, Salt Point, NY 12578
    44 Eleanor Dr, Salt Point, NY 12578
    44 Eleanor Dr, Salt Point, NY 12578
    /49

    $799,000

    • 4 Beds
    • 3 Baths
    • 2,438 Sq Ft

    44 Eleanor Dr, Salt Point, NY 12578

    Tucked away on 3.66 private acres in the heart of Salt Point, this custom contemporary home offers a rare combination of seclusion, character, and functionality. Surrounded by mature trees and natural landscape, the property provides a peaceful setting while remaining conveniently located to nearby amenities and commuter routes. Designed with a unique architectural style, the home features 2,438

    STEVEN WROBEL JR. Serhant LLC

    44 Eleanor Dr, Salt Point, NY 12578
  • 69 Brown Rd, Pleasant Valley, NY 12569

    $830,000

    Sold Feb 13, 2026

    69 Brown Rd, Pleasant Valley, NY 12569

    • 3 Beds
    • 3.5 Baths
    • 2,567 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Below List Price
    • $323/SF
    • 140 Days On Market

    Current Estimated Value $828,560

    Last Listing Agent Susan Whalen George T Whalen Real Estate

    69 Brown Rd, Pleasant Valley, NY 12569
  • 41 Meddaugh Rd, Pleasant Valley, NY 12569
    41 Meddaugh Rd, Pleasant Valley, NY 12569
    41 Meddaugh Rd, Pleasant Valley, NY 12569
    /37

    $750,000

    $45K 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
  • 41 Mountain Dr, Pleasant Valley, NY 12569

    $485,000

    Sold Jun 01, 2026

    41 Mountain Dr, Pleasant Valley, NY 12569

    • 3 Beds
    • 2.5 Baths
    • 1,840 Sq Ft
    • Built 1970

    Last Sold Summary

    • 3% Below List Price
    • $264/SF
    • 34 Days On Market

    Current Estimated Value $493,967

    Last Listing Agent JENNIFER HOYE BHHS Hudson Valley Properties

    41 Mountain Dr, Pleasant Valley, NY 12569
  • 56 Water Loop, Pleasant Valley, NY 12569
    56 Water Loop, Pleasant Valley, NY 12569
    56 Water Loop, Pleasant Valley, NY 12569
    /4

    $120,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    56 Water Loop, Pleasant Valley, NY 12569

    3 BR mobile home in Pleasant Valley NY. Arlington School DIstrict. SGD to deck.Applianes included, range, ref, dw. $800 fee includes taxes. Great location Minutes to Taconic Parkway. Country atmosphere. Shopping, hospitals, trains only short car ride. 15 minutes to Poughkeepsie and Hudson River mansions in Hyde Park NY.

    ED DELFORNO DelForno Associates real estate Agency, Inc

    56 Water Loop, Pleasant Valley, NY 12569
  • 104 S Quaker Ln, Hyde Park, NY 12538

    $710,000

    Sold Apr 27, 2026

    104 S Quaker Ln, Hyde Park, NY 12538

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft
    • Built 1870

    Last Sold Summary

    • 5% Below List Price
    • $459/SF
    • 77 Days On Market

    Current Estimated Value $665,826

    Last Listing Agent Luis Gordillo Schunk Realty Group

    104 S Quaker Ln, Hyde Park, NY 12538
  • 129 Clinton Corners Rd, Salt Point, NY 12578
    129 Clinton Corners Rd, Salt Point, NY 12578
    129 Clinton Corners Rd, Salt Point, NY 12578
    /41

    $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
  • 2 English Way, Pleasant Valley, NY 12569

    $640,000

    Sold Mar 18, 2026

    2 English Way, Pleasant Valley, NY 12569

    • 3 Beds
    • 2.5 Baths
    • 2,636 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Below List Price
    • $243/SF
    • 34 Days On Market

    Current Estimated Value $642,393

    Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

    2 English Way, Pleasant Valley, NY 12569
  • 53 Tyrrel Rd, Pleasant Valley, NY 12569
    53 Tyrrel Rd, Pleasant Valley, NY 12569
    53 Tyrrel Rd, Pleasant Valley, NY 12569
    /35

    $549,990

    • 4 Beds
    • 1.5 Baths
    • 2,424 Sq Ft

    53 Tyrrel Rd, Pleasant Valley, NY 12569

    Nestled at the top of a meandering driveway, this charming four bedroom ranch offers privacy, and scenic views in an ideal location. Situated on six serene acres within the desirable Arlington School District, this home combines comfort, space and solitude. Cherished by the same family for over 30 years, where countless memories were created hosting large joyful gatherings and small intimate

    Janet Myer Houlihan Lawrence Inc.

    53 Tyrrel Rd, Pleasant Valley, NY 12569
  • 404 Gretna Rd, Hyde Park, NY 12538

    $630,000

    Sold Mar 19, 2026

    404 Gretna Rd, Hyde Park, NY 12538

    • 5 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • Built 1956

    Last Sold Summary

    • 3% Below List Price
    • $210/SF
    • 112 Days On Market

    Current Estimated Value $636,808

    Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

    404 Gretna Rd, Hyde Park, NY 12538
  • 1666 Main St, Pleasant Valley, NY 12569
    1666 Main St, Pleasant Valley, NY 12569
    1666 Main St, Pleasant Valley, NY 12569
    /30

    $375,000

    • 3 Beds
    • 2 Baths
    • 2,232 Sq Ft

    1666 Main St, Pleasant Valley, NY 12569

    Welcome to 1666 Main Street, a beautifully renovated classic early-1900s home in the heart of Pleasant Valley. This move-in ready property offers 3–4 bedrooms, 2 full baths, and over 2,000 square feet of living space on a low-maintenance .20-acre lot in the Arlington School District with low taxes. Inside, you’ll find refinished 100+ year-old Maple and Douglas Fir hardwood floors, upgraded

    Kiyoshi Henson RE/MAX Town & Country

    1666 Main St, Pleasant Valley, NY 12569
  • 106 Stream Ln, Pleasant Valley, NY 12569

    $600,000

    Sold Jul 22, 2025

    106 Stream Ln, Pleasant Valley, NY 12569

    • 3 Beds
    • 2.5 Baths
    • 2,678 Sq Ft
    • Built 1964

    Last Sold Summary

    • 6% Below List Price
    • $224/SF
    • 137 Days On Market

    Current Estimated Value $621,724

    Last Listing Agent Sharon Pehush HomeSmart Homes & Estates

    106 Stream Ln, Pleasant Valley, NY 12569

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