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Philipstown, NY Homes for Sale with Pool

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  • /19

    $574,999

    • 4 Beds
    • 2 Baths
    • 1,994 Sq Ft

    11 Hustis Rd, Cold Spring, NY 10516

    Tucked away in a serene setting, this inviting property offers a wonderful blend of comfort and outdoor enjoyment. The private backyard is perfect for relaxing or entertaining, complete with an in-ground pool that creates your own summer retreat. Inside, a wood-burning fireplace adds warmth and character, creating a cozy focal point for cooler seasons. A two-car garage provides convenience along

    Elijah Hoskins Redfin Real Estate

    11 Hustis Rd, Cold Spring, NY 10516
  • /40

    $3,200,000

    • 5 Beds
    • 4.5 Baths
    • 6,216 Sq Ft

    20 S Mountain Pass Spur, Garrison, NY 10524

    Just 60 minutes from Manhattan, this exceptional Hudson Highlands retreat offers a rare combination of architectural character, protected natural surroundings, and direct access to some of the region’s most celebrated outdoor destinations. Set on 13 private acres across two separate lots—including a second vacant, buildable parcel—the property is tucked away on a quiet dirt road known for its

    Annabel Taylor Four Seasons Sothebys Intl

    20 S Mountain Pass Spur, Garrison, NY 10524
  • /39

    $2,900,000

    • 4 Beds
    • 3.5 Baths
    • 2,967 Sq Ft

    37 Paulding Ave, Cold Spring, NY 10516

    An architectural crown jewel in the heart of Cold Spring village, The Chestnut Estate is a masterfully restored 1865 Gothic Victorian. Beneath a hand scalloped slate roof, this property delivers grand proportions befitting a true historic compound. Inside soaring ornate ceilings, wide-plank floors, hand-carved arches and heirloom-quality wood work welcome you. The expansive four-bedroom layout

    Melissa Carlton Houlihan Lawrence Inc.

    37 Paulding Ave, Cold Spring, NY 10516
  • /33

    $659,999

    • 4 Beds
    • 2.5 Baths
    • 2,214 Sq Ft

    21 E Mountain Rd S, Cold Spring, NY 10516

    Welcome to 21 East Mountain Road South in Cold Spring, NY — a beautifully maintained 4-bedroom, 2.5-bath ranch set on 1.1 flat private acres in the highly sought-after Haldane Central School District. This warm and inviting home offers effortless single-level living with original hardwood floors, skylights, central air, 3-zone heating, and a bright open-concept layout designed for everyday

    Jake Rotger Real Broker NY LLC

    21 E Mountain Rd S, Cold Spring, NY 10516
  • /47

    $8,950,000

    • 6 Beds
    • 5.5 Baths
    • 6,252 Sq Ft

    61 Evarts Hill Unit 41, Garrison, NY 10524

    Set upon a private rise within the Hudson Highlands, Evarts Hill is a restored 1929 French Normandy style estate distinguished by its provenance, craftsmanship, and natural and formal landscapes. Encompassing 53.65 acres and bordered by conserved lands of the Hudson Highlands Land Trust, the property offers exceptional privacy and an unspoiled natural setting just 50 miles from New York

    Anthony Cutugno William Pitt Sothebys Int Rlty

    61 Evarts Hill Unit 41, Garrison, NY 10524
  • /2

    $698,000

    $3K PRICE INCREASE Coming Soon
    • 2 Beds
    • 2 Baths
    • 1,974 Sq Ft

    10 Maggie May Way Unit 3366, Cold Spring, NY 10516

    If you have been patiently waiting for the perfect Hudson Valley home that checks every single box—from effortless one-floor living and high-end barefoot luxury to a vibrant, resort-style social scene—your wait is officially over! Welcome to 10 Maggie May Way, an exceptional single-level residence that seamlessly pairs next-generation green technology with an unparalleled lifestyle. Offering the

    Christine Hamilton Keller Williams Realty Partner

    10 Maggie May Way Unit 3366, Cold Spring, NY 10516
  • /47

    $4,995,000

    • 8 Beds
    • 7 Baths
    • 10,626 Sq Ft

    1070 Route 9d, Garrison, NY 10524

    Gothic Revival Country House.Welcome to the Hurst-Pierrepont Estate. This Gothic beauty, situated in the picturesque Hudson Valley is truly a one of a kind offering. The house completed in 1867, designed by Alexander Jackson Davis for Edwards Pierrepont as a country home, sits on almost 20 verdant acres with pool, patio, pond, perennial gardens and specimen trees. Preserving the home's rich

    Heather Fitzgerald Coldwell Banker Realty

    1070 Route 9d, Garrison, NY 10524
  • /24

    $775,000

    • 3 Beds
    • 2 Baths
    • 1,868 Sq Ft

    17 Fowler Ave, Cortlandt Manor, NY 10567

    Beautiful ranch-style home built in 2019 offering the perfect blend of modern comfort and country charm! This well-maintained home features an inviting open layout, a cozy pellet stove, and an attached 2-car garage. Enjoy outdoor living with a spacious, flat yard and a beautiful above-ground pool — perfect for entertaining, relaxing, or enjoying summer days at home. The home also offers a huge

    Crystal Colombo Compass Greater NY, LLC

    17 Fowler Ave, Cortlandt Manor, NY 10567
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