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Millbrook, NY Homes for Sale with Pool

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  • /33

    $11,500,000

    • 5 Beds
    • 6.5 Baths
    • 6,054 Sq Ft

    129 W Meadow Ln, Millbrook, NY 12545

    Set in the hills above Millbrook, West Meadow is encircled as far as the eye can see by endless, heart-stopping views of the entire Hudson Valley. The house and pool sit on a beautifully landscaped plateau above a sloping lawn that gives way to a prolific cutting garden, rose beds, tennis court wrapped in wisteria vines, and groomed meadows. A fruit orchard and abundant vegetable garden enhance

    Candy Anderson Compass Greater NY, LLC

    129 W Meadow Ln, Millbrook, NY 12545
  • /50

    $5,500,000

    New Construction
    • 4 Beds
    • 5.5 Baths
    • 6,244 Sq Ft

    3585 Route 82, Millbrook, NY 12545

    Welcome to Sunset Ridge Farm. A discreet tree-lined drive with expansive views of two aerated ponds and rolling hills leads to this breathtaking modern farmhouse estate. Set on 10 exquisitely manicured acres with mountain vistas, a heated in-ground pool, spa, and gardens reminiscent of the English countryside, 3585 Route 82 is a truly rare offering — a perfect full-time residence or refined

    Jordan Vaccaro Serhant LLC

    3585 Route 82, Millbrook, NY 12545
  • /20

    $4,495,000

    New Construction
    • 4 Beds
    • 5 Baths
    • 5,679 Sq Ft

    101 N Tower Hill Rd, Millbrook, NY 12545

    **TO BE BUILT** Prepare to be impressed. Nestled on nearly 8 private acres in the heart of Millbrook, this exceptional custom-built estate offers nearly 6,000 square feet of thoughtfully designed living space, blending timeless craftsmanship with modern efficiency and luxury. Featuring 4 spacious bedrooms, 5 full baths and oversized 3 car garage, the home provides an ideal balance of comfort,

    Ronald Green KW MidHudson

    101 N Tower Hill Rd, Millbrook, NY 12545
  • /50

    $1,800,000

    • 7 Beds
    • 7 Baths
    • 11,222 Sq Ft

    3893 Route 82, Millbrook, NY 12545

    Set on 11.1 private acres in the heart of Millbrook, this stately brick Colonial estate offers over 11,222 square feet of refined living space, combining timeless elegance with exceptional versatility. A true legacy property, it delivers the scale, design, and amenities expected by the most discerning buyers.A dramatic two-story granite foyer welcomes you with a sweeping double staircase and

    Howard Payson RE/MAX Town & Country

    3893 Route 82, Millbrook, NY 12545
  • /49

    $4,250,000

    • 4 Beds
    • 5 Baths
    • 4,253 Sq Ft

    296-302 Stanford Rd, Millbrook, NY 12545

    Completely reimagined and renovated in 2026, this exceptional Millbrook compound offers an extraordinary blend of timeless architecture, modern luxury, and refined craftsmanship. Set on 18.92 private acres, the property encompasses a beautifully updated four or five bedroom, three full and two half bath main residence and a separate two bedroom, two and a half bath guest house. A dramatic formal

    Paula Redmond Corcoran Country Living - Mill

    296-302 Stanford Rd, Millbrook, NY 12545
  • /39

    $599,900

    Open Sun 1PM - 3PM $49K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,576 Sq Ft

    6 Route 343, Millbrook, NY 12545

    Welcome to this warm and inviting 3-bedroom, 1.5-bath home nestled in the heart of Dutchess County, just minutes from the Village of Millbrook and the Taconic State Parkway. From the moment you step into the entry foyer, you'll feel the character and comfort this home has to offer.The sun-filled living room impresses with a beamed ceiling and wood-burning fireplace — the perfect gathering

    Rebecca Marino Corcoran Country Living

    6 Route 343, Millbrook, NY 12545
  • /36

    $729,000

    • 3 Beds
    • 2 Baths
    • 2,556 Sq Ft

    580 Oak Summit Rd, Millbrook, NY 12545

    Charming country Cape Cod style home located minutes from the Village of Millbrook. This home offers an open floor plan with wood flooring, custom built kitchen cabinets, granite countertops, and stainless steel appliances. Dining room has slider to deck. Primary bedroom on first floor with full bath, including washer & dryer. Two large bedrooms are located on the second floor with a second full

    George Whalen III George T Whalen Real Estate

    580 Oak Summit Rd, Millbrook, NY 12545
  • /50

    $2,799,999

    $950K PRICE DROP
    • 3 Beds
    • 5 Baths
    • 4,134 Sq Ft

    97 Valley Farm Rd, Millbrook, NY 12545

    New, never lived in, move in ready, almost 20 acres, just outside the Village of Millbrook, stunning, fully remodeled total renovation (both inside and out), country property with the most gorgeous sweeping Catskill Mountain Views. No expense was spared. Pure luxury inside and out. Inside: All brand new: windows, doors, heating & cooling system, plumbing and electrical, water purification system,

    Susan Whalen George T Whalen Real Estate

    97 Valley Farm Rd, Millbrook, NY 12545
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