5-Bedroom Homes for Sale in Dutchess County NY

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  $3,900,000

  • 6 Beds
  • 7.5 Baths
  • 7,460 Sq Ft

  259 Woodstock Rd, Millbrook, NY 12545

  Peace and tranquility await at this sprawling country retreat. A stream meanders through the 15.37 acre property forming two waterfalls and flows into a deep water pond creating a beautiful lush landscape viewed from many vantage points. This amazing and expansive 7,460 square foot home is comprised of three 18th century structures that were dismantled and brought together. At the center of the

  PAULA REDMOND Corcoran Country Living

  259 Woodstock Rd, Millbrook, NY 12545
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  /43

  $1,150,000

  • 5 Beds
  • 3.5 Baths
  • 3,664 Sq Ft

  3715 Route 44 Unit 37, Millbrook, NY 12545

  This historic 1800s home of James Mabbett sits on 4 plus acres with a pristine pond and extensive outbuildings. The main house with its fine architectural details has been newly renovated and updated with new baths and kitchen, appliances, fixtures, mechanicals, gleaming hardwood floors, moldings and coffered ceilings. Enter the high ceiling elegant foyer which leads to a living room with a

  ANN WILKINSON Compass Greater NY, LLC

  3715 Route 44 Unit 37, Millbrook, NY 12545
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  $6,785,000

  • 5 Beds
  • 5.5 Baths
  • 5,162 Sq Ft

  47 Crescent Rd, Millbrook, NY 12545

  Exquisitely restored 1822 farmhouse on 50+ acres in Millbrook, NY, blending historic charm and modern luxury. This stunning home features sun-filled rooms, original hardwood floors, and six fireplaces. The gourmet kitchen is equipped with marble countertops, high-end appliances, a butler's pantry, and a fireplace. A beautiful sunroom with floor-to-ceiling windows and marble floors connects

  William Melnick Elyse Harney Real Estate

  47 Crescent Rd, Millbrook, NY 12545
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  /36

  $8,000,000

  • 6 Beds
  • 8 Baths
  • 8,933 Sq Ft

  Unlisted Address

  Perched on the crest of a plateau overlooking panoramic, protected views, West Wind Hill, a bespoke country estate on 389± acres, straddles Kent, CT and Amenia, NY. Experience this truly magnificent classic stone and shingle manor house sited perfectly to experience lush sunsets and fairytale mists with the upmost in privacy. Only eight minutes from the center of Kent and less than two

  Joseph Lorino Brown Harris Stevens HV LLC

  Unlisted Address
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  /36

  $630,000

  • 6 Beds
  • 2.5 Baths
  • 3,402 Sq Ft

  10 Greenwood Dr, Beacon, NY 12508

  This expansive (3,400 sq. ft.) split-level ranch is on 1.6 acres and features 6 bedrooms, 2.5 baths, and a 2-bedroom accessory apartment with a private entrance bordering numerous hiking trails. THREE additional adjoining lots are sold separately and require BOHA approval although municipal water is provided by the town (.58 acres MLS 6321787, .57 acres MLS 6321777, & 1.02 acres MLS 6325550).

  TIMOTHY TURNER Keller Williams Hudson Valley

  10 Greenwood Dr, Beacon, NY 12508
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  $6,995,000

  • 12 Beds
  • 8 Baths
  • 7,084 Sq Ft

  20 Smithfield Way, Amenia, NY 12501

  Set on 118 Bucolic acres in the heart of the Hudson Valley, Smithfield Farm is an exquisite estate, offering breathtaking, sweeping western views of the Smithfield Valley and the Catskill mountains. The centerpiece of the estate is a meticulously preserved 1790 Colonial main house with a stately brick exterior and a grand center hall. Inside, you will find four woodburning fireplaces, central air

  OLIVER BROWN Houlihan Lawrence Inc.

  20 Smithfield Way, Amenia, NY 12501
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  /31

  $65,000,000

  • 10 Beds
  • 8 Baths
  • 14,706 Sq Ft

  45 Hitchcock Ln, Millbrook, NY 12545

  The Hitchcock Estate is an exceptional property in size, location and history. The property has 2078 acres intact since the first owner assembled it from 5 area farms in 1889. Located in the heart of Millbrook, NY it has remained undeveloped, shrouded in mystique, the subject of curiosity and imagination providing now and then a glimpse into its elegant and storied past. Beginning as a summer

  HEATHER CRONER William Pitt Sothebys Int Rlty

  45 Hitchcock Ln, Millbrook, NY 12545
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  $10,500,000

  • 5 Beds
  • 5.5 Baths
  • 5,170 Sq Ft

  292 Wood Duck Rd, Amenia, NY 12501

  In a coveted position on the lake, 292 Wood Duck Road presents an extraordinary opportunity to own a turnkey property just two hours from Manhattan. The pristine estate spans approximately 5,000+ square feet of interior space, complimented by more than 1,800+ square feet of outdoor terrace and covered porch.The home includes five beautifully appointed ensuite bedrooms and two half baths.

  Jonathan Stein Douglas Elliman Real Estate

  292 Wood Duck Rd, Amenia, NY 12501
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  $495,000 Open Sat 1PM - 3PM

  • 6 Beds
  • 3.5 Baths
  • 2,916 Sq Ft

  19 Bennett Rd, Poughkeepsie, NY 12601

  Perfectly suited for siblings, a young family, or multigenerational living, this unique property offers the privacy of separate homes with the convenience of proximity—ideal for shared meals and babysitting. Located in a tranquil rural neighborhood, this charming property presents an exceptional opportunity for family living or investment.The main home exudes warmth and character, offering three

  Alan Arnfield Century 21 Alliance Rlty Group

  19 Bennett Rd, Poughkeepsie, NY 12601
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  /30

  $2,995,000

  • 6 Beds
  • 6 Baths
  • 6,118 Sq Ft

  644 Tower Hill Rd, Millbrook, NY 12545

  Experience the charm of country living in Millbrook with this 110-acre estate. As you wind your way along the quaint country road and up the circular driveway, you're greeted by manicured lawns, lush pastures, and majestic oak trees, setting the stage for the grandeur that awaits. The main residence, a masterpiece of architectural design, boasts over 6,000 sqft of traditional elegance blended

  OLIVER BROWN Houlihan Lawrence Inc.

  644 Tower Hill Rd, Millbrook, NY 12545
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  $849,000

  • 5 Beds
  • 4.5 Baths
  • 3,820 Sq Ft

  67 Myers Corners Rd, Wappingers Falls, NY 12590

  Welcome To 67 Myers Corners Rd...This Unique Meticulously Cared For One Of A Kind Colonial Home Sprawled Out In A Country Setting Awaits You To Call Home. Nestled On More Than 2 Acres Is Guaranteed To Provide Peace & Tranquility. Step Inside To A Boasting 3800sqft Of Living Space That Has Plenty Of Charm And Character. Tastefully Updated Throughout With Hardwood Floors, Granite/Marble

  Owais Khan OXM Realty Group LLC

  67 Myers Corners Rd, Wappingers Falls, NY 12590
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  $650,000

  • 5 Beds
  • 2 Baths
  • 2,304 Sq Ft

  22 Hunns Lake Rd, Stanfordville, NY 12581

  Charming country farm house, circa 1772, in the heart of Stanfordville Ny. Spacious 5 bedroom, 2 bath with bonus room for your office/studio. Picturesque views. Close to Wineries, dining, antiques and Polo. Close to Taconic State Parkway and trains. Additional Information: Amenities:Pedestal Sink,Stall Shower,HeatingFuel:Oil Above Ground,

  Christina Coughlin Hudson Valley Home Connection

  22 Hunns Lake Rd, Stanfordville, NY 12581
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  $5,500,000

  • 17 Beds
  • 13 Baths
  • 15,000 Sq Ft

  618 Quaker Hill Rd, Pawling, NY 12564

  25.5-acre equestrian estate with a 43-room Elizabethan Style manor house, two caretaker homes, a carriage house with groom’s quarters, a yoga studio, a 12,000 sq. ft. stable, greenhouse and more. Situated on the crest of Quaker Hill, Elmwood Farm has stunning views and endless possibilities. The 3-story, 17-bedroom (7 of which are in the nursery wing and the caretakers' wing) 9-bath (plus 4

  Harriet Norris Douglas Elliman Real Estate

  618 Quaker Hill Rd, Pawling, NY 12564
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  /12

  $2,100,000

  • Land

  5 Homestead Farm Ln, Millerton, NY 12546

  Once in a lifetime opportunity to acquire one of the last remaining unrestricted working farms in Northern Dutchess County, NY. Choice building sites, panoramic views and seclusion yet convenient to New York City, Metro North commuter train and nearby area amenities including Millerton, NY, Litchfield County, CT, Troutbeck Inn, Millbrook, NY and Silo Ridge. This property is totally unrestricted

  Andrew Gates Houlihan Lawrence, Inc.

  5 Homestead Farm Ln, Millerton, NY 12546
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  /2

  $649,000 Coming Soon

  • 5 Beds
  • 3 Baths
  • 1,900 Sq Ft

  11 Queen Anne Ln, Wappingers Falls, NY 12590

  Charming Home with Income Potential in the Heart of East FishkillWelcome to this beautifully maintained 4-bedroom, 2-bathroom home nestled on a level, landscaped one-acre parcel. From the moment you step onto the inviting covered front porch, you’ll picture yourself enjoying coffee at sunrise or relaxing with evening sunsets.Inside, you’ll find warm and welcoming living spaces, including a cozy

  Bernadette Smyth Coldwell Banker Realty

  11 Queen Anne Ln, Wappingers Falls, NY 12590

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