26

Homes for Sale near Millbrook School

Section Image
  • /33

    $8,900,000

    • 5 Beds
    • 7 Baths
    • 5,175 Sq Ft

    292 Wood Duck Rd, Amenia, NY 12501

    Refined Luxury. Rare Direct Lakefront Home within the Coveted Silo Ridge Community. 5 Luxurious En-suite Bedrooms Including 2 on Main Level. Jaw Dropping Great Room with Fireplace & Access out to Large Covered Porch with Major Lake & Mountain Views. Extremely High Quality Construction with Numerous Luxury Appointments Including: Lutron 1-Touch Lighting; Multi-Zone Sound System; 4-Season In Ground

    Graham Klemm GRAHAM T. KLEMM LIC. RE BROKER

    292 Wood Duck Rd, Amenia, NY 12501
  • /34

    $5,500,000

    • 7 Beds
    • 5 Baths
    • 6,019 Sq Ft

    20 Smithfield Way, Amenia, NY 12501

    Welcome to Smithfield Farms! Set on 53+ Bucolic acres in the heart of the Hudson Valley, Smithfield Farms 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

    OLIVER BROWN Houlihan Lawrence Inc.

    20 Smithfield Way, Amenia, NY 12501
  • /25

    $5,900,000

    • 3 Beds
    • 4 Baths
    • 4,247 Sq Ft

    1135 Duell Rd, Stanfordville, NY 12581

    Perched atop 40.9 private acres, this exceptional custom-built estate offers unrivaled privacy and sweeping panoramic views of the Catskill Mountains. Blending timeless craftsmanship with modern luxury, this hilltop retreat embodies refined living in a breathtaking natural setting. Inside, antique teak flooring flows throughout the home, adding warmth and character to every space. The open floor

    PATRICIA McNAMEE William Pitt Sothebys Int Rlty

    1135 Duell Rd, Stanfordville, NY 12581
  • /40

    $8,800,000

    • 8 Beds
    • 10 Baths
    • 8,224 Sq Ft

    406 Shunpike, Millbrook, NY 12545

    Linley House Estate - A Once-in-a-Generation Hudson Valley Opportunity. Perhaps only once in a generation does such a rare opportunity arise to acquire one of the most private, historically significant, and visually commanding estates in the heart of the Hudson Valley. Welcome to The Linley House Estate, an extraordinary Greek Revival Center Hall Colonial set on over 113 pastoral acres across

    Andrew Gates Houlihan Lawrence, Inc.

    406 Shunpike, Millbrook, NY 12545
  • /35

    $1,400,000

    • 3 Beds
    • 8 Baths
    • 10,689 Sq Ft

    4258 Route 44, Millbrook, NY 12545

    This distinctive property in the heart of Dutchess County combines historic character with over 10,000 square feet of versatile residential and commercial potential. Originally built in the 19th century as a Congregational church, the building has enjoyed a rich history and now offers endless possibilities for its next chapter. The expansive main level features multiple gathering areas, soaring

    Stephen Pener William Pitt Sothebys Int Rlty

    4258 Route 44, Millbrook, NY 12545
  • /26

    $2,379,000

    • Land
    • 206.14 Acres
    • $11,541 per Acre

    0 Cascade Mt Perrys Corners Rd Unit KEYH6310518, Amenia, NY 12501

    An opportunity to own a magnificent combination of two rural properties. Explore this enchanting yet tranquil 206.14 acres of rolling hills, mature forests and ample meadow that is currently in organic crop production. There are a couple of steep slopes that contribute to buffering a few captivating and extremely private home sites. The terrain is ideal for a retreat and multiple dwellings. Maybe

    Larry Havens Havens Real Estate

    0 Cascade Mt Perrys Corners Rd Unit KEYH6310518, Amenia, NY 12501
  • /50

    $11,750,000

    • 5 Beds
    • 6 Baths
    • 9,684 Sq Ft

    147 Moadock Rd, Millerton, NY 12546

    Exquisite Shekomeko Estate with Panoramic Catskill Mountain views. Nestled on 50 private acres in the heart of the Hudson Valley, this country estate offers timeless sophistication, refined comfort, and breathtaking views of the Catskills. Designed by architect Jimmy Crisp and completed in 2004, the residence spans over 9,684 finished square feet of thoughtfully curated living space. A tree-lined

    PAULA REDMOND Corcoran Country Living

    147 Moadock Rd, Millerton, NY 12546
  • /36

    $525,000

    • 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
  • /15

    $479,000

    • Land
    • 49.63 Acres
    • $9,651 per Acre

    0 Cascade Mountain Rd Unit 419986, Amenia, NY 12501

    Discover the perfect spot for your modern or log home - a private parcel perched on a hill, embraced by the tranquility of the forest. These idyllic home sites provide an ideal retreat from the hustle and bustle of city life. Just minutes away from the Wassaic Train Station and the Harlem Valley Rail Trail, this location invites you to plan your escape. Lace up your hiking boots and schedule a

    Larry Havens Havens Real Estate

    0 Cascade Mountain Rd Unit 419986, Amenia, NY 12501
  • /23

    $599,000

    • 9 Beds
    • 4 Baths
    • 3,952 Sq Ft

    276 Old Route 22, Wassaic, NY 12592

    Whether you’re seeking an investment property, multi-generational living, or the opportunity to live in one unit while generating rental income from the other two, this versatile property is ready to meet your needs. This well-designed triplex features three townhome-style apartments, each offering three bedrooms, a welcoming front porch, a private rear patio, and a one-car attached garage. Every

    Stacey Cronin Houlihan Lawrence Inc.

    276 Old Route 22, Wassaic, NY 12592
  • /25

    $800,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    247 N Mabbettsville Rd, Millbrook, NY 12545

    Set on a landscaped acre just minutes from the Village of Millbrook, this cottage offers a comfortable, well-planned layout with a sense of privacy and ease. The main level is bright and welcoming, with wood floors throughout and a living room centered around a gas fireplace. Windows bring in natural light and views of the surrounding lawn, giving the space a relaxed, connected feel.The

    Jill Rose Houlihan Lawrence Inc.

    247 N Mabbettsville Rd, Millbrook, NY 12545
  • /14

    $1,900,000

    • Land
    • 156.51 Acres
    • $12,140 per Acre

    0 Perrys Corners Rd Unit KEYM419993, Amenia, NY 12501

    Indulge in breathtaking privacy, featuring a couple of extraordinary homesites harmoniously integrated into the enchanting landscape of meadows and woodlands. This premium land offering maintains a commitment to organic farming, ensuring a connection to nature. Tucked away from the road, this is an optimal setting for those desiring a distinguished location with ample space for exploration,

    Larry Havens Havens Real Estate

    0 Perrys Corners Rd Unit KEYM419993, Amenia, NY 12501
  • /40

    $2,500,000

    • 13 Beds
    • 7 Baths
    • 7,076 Sq Ft

    18 Stagecoach Ln, Amenia, NY 12501

    Step into a turn key investment with 9 years of profitable short term rental history and a business backed by a long standing, proven financing track record! This exceptional 1790 Georgian style estate comes with three standalone cottages, all fully renovated and operating as highly sought after vacation rentals. With commercial zoning already in place, this property blends historic charm, modern

    Dominick DiFilippo Keller Williams Realty Partner

    18 Stagecoach Ln, Amenia, NY 12501
  • /38

    $975,000

    • 5 Beds
    • 2 Baths
    • 1,960 Sq Ft

    37 Sheffield Rd, Amenia, NY 12501

    This vintage 1780 Salt Box with an ADU (Accessory Dwelling Unit) Second house/Barn is approximately 2,000 sq. ft.(commercial, electric for barn) sits high on 3.9 private acres in a peaceful quiet area just a few minutes from the Wassaic train station which is the last stop on the Metro-North Harlem Line & two hours to Grand Central Terminal. The property abuts the rail trail and is 5 miles from

    Susan Spivak Houlihan Lawrence Inc.

    37 Sheffield Rd, Amenia, NY 12501
  • /9

    $129,000

    • Land
    • 33,976 Sq Ft
    • $165,385 per Acre

    0 Route 343 Unit KEY896113, Amenia, NY 12501

    Rare opportunity to own vacant land in a Hamlet Mixed Use area. We have a detailed plan for a proposed build that would be 60x 28 and ample parking. The exposure on Route 343 is exceptional.Any building is subject to planning and zoning approval.

    Larry Havens Havens Real Estate

    0 Route 343 Unit KEY896113, Amenia, NY 12501
  • /44

    $600,000

    • 3 Beds
    • 2 Baths
    • 1,705 Sq Ft

    287 Hunns Lake Rd, Stanfordville, NY 12581

    There's a quiet sense of arrival at 287 Hunns Lake Road, where the pace softens and the setting begins to shape the rhythm of the day. Tucked along nearly three acres of lawn and woodland in the heart of Dutchess County, this thoughtfully updated home offers something increasingly rare in the Hudson Valley: room to breathe, a layout that just works, and a location that puts the countryside and

    Alex Mashkin Keller Williams Realty Partner

    287 Hunns Lake Rd, Stanfordville, NY 12581
  • /16

    $420,000

    • 3 Beds
    • 3 Baths
    • 1,296 Sq Ft

    126 Perrys Corners Rd, Amenia, NY 12501

    Offered for the first time ever, this beloved home has been a cherished sanctuary for one family since 1963. Featuring 3 bedrooms and 3 baths, it’s thoughtfully designed to adapt to today’s busy lifestyle. Hardwood floors lie beneath the carpeting, ready to shine. The finished lower-level family room is perfect for an office, music studio, or playroom—your options are endless. This is a

    Larry Havens Havens Real Estate

    126 Perrys Corners Rd, Amenia, NY 12501
  • /11

    $199,000

    • 3 Beds
    • 1.5 Baths
    • 1,866 Sq Ft

    64 Depot Hill Rd, Amenia, NY 12501

    Multiple Offers The seller has request highest and best offers by 2:00 PM Friday May 8, 2026.Septic pumped July 2021. 1000 gallons.Thank you Larry Perched on Depot Hill Road with commanding views and radiant sunsets, this Amenia property is brimming with potential. The flexible layout allows for a variety of living arrangements, but the home is in need of a complete overhaul. A full

    Larry Havens Havens Real Estate

    64 Depot Hill Rd, Amenia, NY 12501
  • /7

    $229,000

    • Land
    • 5 Acres
    • $45,800 per Acre

    Lot # 5 Smithfield Rd, Millerton, NY 12546

    Welcome to Smithfield Road—where open meadows, gentle woodlands, and sweeping pastoral views create the perfect setting for your dream home. With BOHA approval already in place on this 5-acre parcel, you're one step closer to building your own Hudson Valley retreat.A bit of strategic clearing will unlock even more beauty and possibilities. This peaceful location feels worlds away, yet it's

    Larry Havens Havens Real Estate

    Lot # 5 Smithfield Rd, Millerton, NY 12546
  • /9

    $70,000

    • Land
    • 24,829 Sq Ft
    • $122,807 per Acre

    5019 Route 22, Amenia, NY 12501

    Located at 5019 Route 22 in the Town of Amenia, this 24,829 sq ft lot offers a great opportunity to build. Previously had a structure that was removed after a 2014 fire, and is now a blank canvas. Enjoy a highly desirable location within walking distance to local shops, dining, and everyday amenities, making it perfect for those seeking a central and accessible setting. Whether you're looking to

    Theresia Schoonmaker Epique Realty

    5019 Route 22, Amenia, NY 12501
  • /27

    $899,000

    • 8 Beds
    • 4 Baths
    • 3,478 Sq Ft

    762 Old Route 22, Amenia, NY 12501

    Whether you're seeking a property with positive cash flow, a multigenerational living setup, or the ability to live on-site while generating rental income, this unique offering delivers exceptional versatility. The property features two separate duplex buildings along with an adjacent lot, providing added privacy and future expansion possibilities. Each duplex consists of two well-appointed

    Stacey Cronin Houlihan Lawrence Inc.

    762 Old Route 22, Amenia, NY 12501
  • /4

    $250,000

    • Land
    • 3.3 Acres
    • $75,758 per Acre

    8 Yellow City Rd, Amenia, NY 12501

    8 Yellow City Rd offers a rare opportunity to build your dream home in a prime location. This residential lot is fully approved for four bedroom home and already has underground pow installed, making it truly ready to build Enjoy an incredible setting with great views, just minutes from town and steps from the rail trail-perfect for walking, biking, and out door living.well has been drilled

    Bill Flood Houlihan Lawrence Inc.

    8 Yellow City Rd, Amenia, NY 12501
  • /20

    $365,000

    • 3 Beds
    • 1 Bath
    • 1,976 Sq Ft

    24 Wilson Eaton Rd, Amenia, NY 12501

    Situated on 2.45 acres of land in the Town of Amenia, you will find this three-bedroom ranch style home. The grounds are lovely, with a private, mostly level yard. The home provides single level living and the property includes a detached three bay garage with a one-bedroom apartment on the second floor. Perfect property for a first-time home buyer or an investor. Conveniently located minutes

    Susan Whalen George T Whalen Real Estate

    24 Wilson Eaton Rd, Amenia, NY 12501
  • /7

    $129,000

    • Land
    • 33,976 Sq Ft
    • $165,385 per Acre

    0 Route 343 Unit 20253568, Amenia, NY 12501

    Hamlet Mixed Use Zoning. The only vacant parcel in that Zone that is available for sale.There is great visibility on Route 343 and this parcel has a well in place.The seller has a sketch plan for a building that also shows parking. This plan has not been approved or filed but simply shows the possibilities.An extraordinary opportunity !

    Larry Havens Havens Real Estate

    0 Route 343 Unit 20253568, Amenia, NY 12501
  • /25

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    54 Midway Ave, Amenia, NY 12501

    Motivated sellers! True move-in condition. Nicely updated 3 bedroom/2 bath home with a lovely front porch. Both the front and rear entrances feature a mudroom with plenty of storage for coats, shoes, etc. Washer/dryer on first floor, along with a full bath featuring a shower. Cozy living room with a pellet stove. Eat-in kitchen/dining area. First floor bedroom can also be used as flex space.

    Melinda Torres eXp Realty

    54 Midway Ave, Amenia, NY 12501
  • /31

    $1,179,000

    • 4 Beds
    • 4 Baths
    • 3,661 Sq Ft

    5-15 Old Depot Way, Stanfordville, NY 12581

    If you crave a truly unique property, love history or dream of hosting short term rentals, this property might be your ticket to ride. Built in 1889, the historic Train Station in the hamlet of Stanfordville is the only existing station remaining along the original former P&C line that ran alongside Wappinger Creek (known as one of the top 10 trout streams in NYS). Originally, the buildings

    George Langa Houlihan Lawrence Inc.

    5-15 Old Depot Way, Stanfordville, NY 12581
How to Buy a Home How to Finance a Home How to Sell a Home