11

Pleasant Valley, NY Homes for Sale with Pool

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  • /43

    $1,300,000

    • 5 Beds
    • 3.5 Baths
    • 4,841 Sq Ft

    498 Rossway Rd, Pleasant Valley, NY 12569

    Looking for a private getaway or country full time home with Mother and daughter unit or additional income to pay the mortgage? Enter into a long driveway that takes you to the top of the hill to a sight of a beautiful contemporary home with 18 x 36 Inground Pool, Very unique and totally secluded! Nestling on 16.05 wooded acres, this custom appointed u-shape home is one of a kind! The main

    Arlene Campbell BHHS Hudson Valley Properties

    498 Rossway Rd, Pleasant Valley, NY 12569
  • /35

    $1,525,000 Open Sun 1PM - 3PM

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

    101 Drake Rd, Pleasant Valley, NY 12569

    CONVERTED BARNS WITH POOL. This charming getaway offers fun lofty spaces to gather, entertain and enjoy the countryside, while conveniently located to the TSP and Millbrook Village. This 19th century converted barn was beautifully preserved and showcases the exposed beams and wide board floors. Upon entering, one is enamored by the soaring vaulted ceilings with exposed beams in the center of the

    PAULA REDMOND Corcoran Country Living

    101 Drake Rd, Pleasant Valley, NY 12569
  • /35

    $1,179,000

    • 3 Beds
    • 2 Baths
    • 2,700 Sq Ft

    129 Clinton Corners Rd, Salt Point, NY 12578

    129 Clinton Corners Road, Salt Point, NYA rare and exceptional offering—this private 18.5-acre estate blends natural beauty, architectural charm, and modern updates, all in a prime location just off the Taconic Parkway for easy commuting.This stunning post-and-beam 4,300 sq ft contemporary home features soaring 25-foot cathedral ceilings, a central stone wood-burning fireplace, and

    Ginalea Healy K. Fortuna Realty, Inc.

    129 Clinton Corners Rd, Salt Point, NY 12578
  • /45

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 3,888 Sq Ft

    27 Gallagher Dr, Pleasant Valley, NY 12569

    Set amid the rolling hills of Pleasant Valley, The Gallagher offers a harmonious blend of financial opportunity and country tranquility, boasting nearly 200K in annual rental revenue. Designed for gatherings and getaways, this 5-BR, 3.5-BA home unfolds across an open, light-filled layout. The heart of the home is the expansive chef's kitchen - outfitted with dual convection ovens, a gas range and

    Angelica Ferguson Houlihan Lawrence Inc.

    27 Gallagher Dr, Pleasant Valley, NY 12569
  • /50

    $1,179,000

    • 4 Beds
    • 4.5 Baths
    • 6,085 Sq Ft

    37 Patricia Dr, Pleasant Valley, NY 12569

    Welcome to this stunning contemporary masterpiece, featuring a resort-style indoor pool and exquisitely designed spaces to suit every lifestyle. Offering over 6,000 square feet of beautifully finished living space, designed for those who appreciate modern style, open spaces, and effortless entertaining. Set on a private, tranquil property, yet just minutes from the vibrant Eastdale Village, this

    Jake Garay Serhant LLC

    37 Patricia Dr, Pleasant Valley, NY 12569
  • /44

    $1,250,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 2,433 Sq Ft

    93 Clinton Corners Rd, Salt Point, NY 12578

    Modern Contemporary Retreat in Salt Point - Welcome to this newly renovated modern contemporary home, where clean lines and thoughtful design meet comfort and functionality. Nestled in the heart of Salt Point, this 3-bedroom, 3-bath residence offers an open and airy floor plan accentuated by striking architectural details throughout.The first floor features a versatile bonus room—perfect

    Robin Bermudez Compass Greater NY, LLC

    93 Clinton Corners Rd, Salt Point, NY 12578
  • /50

    $815,000

    • 6 Beds
    • 4.5 Baths
    • 3,974 Sq Ft

    82 Thornhill Dr, Pleasant Valley, NY 12569

    Stunning Pleasant Valley Colonial in park-like setting: This wonderful 6 bedroom home can be your personal oasis; close enough to civilization to have convenience, yet just rural enough to also have serenity. The acre and a half property features stately, landscaped front & side yards with walkways & mature trees - and a more private, fenced & wooded backyard that is all about relaxing and/or

    Christopher Hanson Hanson Real Estate Partners

    82 Thornhill Dr, Pleasant Valley, NY 12569
  • /32

    $550,000

    • 3 Beds
    • 2.5 Baths
    • 2,094 Sq Ft

    27 Woodland Dr, Salt Point, NY 12578

    Enjoy this Sunlit Salt Point retreat with pool and custom charm! Welcome to this dream escape in the heart of Salt Point! this beautifully crafted 3-bedroom, 2.5 bath home offers the perfect blend of natural beauty and thoughtful design. Nestled on a peaceful property the home features a heated inground pool, ideal for summer relaxation, and a blue stone driveway that adds timeless charm from

    LAUREN VONDERAU Inspire Realty

    27 Woodland Dr, Salt Point, NY 12578
  • /44

    $999,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 4,024 Sq Ft

    12 Wolf Ln, Pleasant Valley, NY 12569

    Tucked away on over 14 acres of total privacy and tranquility, 12 Wolf Lane is a contemporary retreat offering 4,000+ square feet of beautifully designed living space and every amenity you could ask for. From the moment you arrive, you’ll feel the calm, surrounded by nature, fieldstone walls built with stone from the land itself, and the kind of seclusion that’s increasingly hard to

    Jake Garay Serhant LLC

    12 Wolf Ln, Pleasant Valley, NY 12569
  • /26

    $900,000

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

    104 S Quaker Ln, Hyde Park, NY 12538

    Modern Farmhouse Retreat - Discover this beautifully reimagined 1870 farmhouse, set on over 25 private secluded acres in the heart of the Hudson Valley. Fully renovated in 2025 with modern finishes throughout, this 3-bedroom, 2-bath residence is a rare blend of historic charm and today’s design sensibility—perfect as a second home or peaceful weekend retreat.Tucked away down a long drive,

    Curtis Darragh Legacy Land & Homes LLC

    104 S Quaker Ln, Hyde Park, NY 12538
  • /50

    $2,995,000

    • 4 Beds
    • 7 Baths
    • 6,412 Sq Ft

    165 Drake Rd, Pleasant Valley, NY 12569

    Welcome to Timber Lake Farm, a stunning property in the heart of Dutchess County horse country. This Adirondack-style estate offers a harmonious blend of rustic elegance and modern luxury, set on 33.26-acre lot with a pristine 9-acre pond that flows over a waterfall at one end. The bespoke stone and wood home boasts 6,412 square feet of living space sited at the highest elevation point on the

    Kyle Irwin Corcoran Country Living

    165 Drake Rd, Pleasant Valley, NY 12569

Home Trends in Pleasant Valley, NY

Housing Trends

Median Sale Price
$485,000
Median Single Family Sale Price
$485,000
Median Townhouse Sale Price
$475,000
Average Price Per Sq Ft
$267
Number of Homes for Sale
27
Last 12 months Home Sales
74
Months of Supply
4.40
Median List Price
$500,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
15%
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