2,059

Millbrook, NY Homes

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  • /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
  • /27

    $12,000 Per Month

    • 6 Beds
    • 6 Baths
    • 7,872 Sq Ft
    • House for Rent

    6-8 Old Killearn Rd, Millbrook, NY 12545

    Privately tucked away at the end of its own road on just over seven picturesque acres, this exceptional barn conversion offers the kind of country lifestyle most dream about—where crisp autumn mornings begin with coffee overlooking rolling hills, winter evenings are spent gathered around the fire, and every window frames the quiet beauty of the changing seasons. Rich in character and thoughtfully

    Elyse Morris Elyse Harney Real Estate

    6-8 Old Killearn Rd, Millbrook, NY 12545
  • Lot 748535 Hollow Crest Ln, Millbrook, NY 12545

    $130,000

    Sold Mar 12, 2026

    Lot 748535 Hollow Crest Ln, Millbrook, NY 12545

    • Land
    • 6.2 Acres
    • $20,968 per Acre

    Last Sold Summary

    • 31% Above List Price
    • 19 Days On Market

    Last Listing Agent Thomas Santore Coldwell Banker Realty

    Lot 748535 Hollow Crest Ln, Millbrook, NY 12545
  • /9

    $995,000

    • Land
    • 23.49 Acres
    • $42,358 per Acre

    Parcel 1 - TBD Woodstock Rd, Millbrook, NY 12545

    Located just outside the Village of Millbrook on a scenic gravel country road, Old Oaks Woods is a 23.49-acre parcel offering a picturesque setting for your dream retreat. The land features a mix of old-growth forest and walking trails, bordered by charming stone walls and highlighted by a pair of peaceful ponds. A large barn and chicken coop remain on the property. Build your private weekend

    OLIVER BROWN Houlihan Lawrence Inc.

    Parcel 1 - TBD Woodstock Rd, Millbrook, NY 12545
  • /27

    $1,500

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft
    • Condo for Rent

    11 Washington Ave Unit 1, Millbrook, NY 12545

    Bright Large 1 bedroom apartment on first floor of a small apartment house in beautiful village of Millbrook. Walking distance to all shops. Apartment has been newly renovated. Rent is $1500.00 per month. One months rent and one months security required. Interested applicants please describe present employment and how long you have been at the same position. Good credit is required. No pets are

    11 Washington Ave Unit 1, Millbrook, NY 12545
  • 786 N Clove Rd, Millbrook, NY 12545

    $640,000

    Sold Jun 19, 2026

    786 N Clove Rd, Millbrook, NY 12545

    • 4 Beds
    • 2.5 Baths
    • 3,446 Sq Ft
    • Built 1954

    Last Sold Summary

    • 2% Below List Price
    • $186/SF
    • 163 Days On Market

    Current Estimated Value $647,142

    Last Listing Agent Diana Wiemer Houlihan Lawrence Inc.

    786 N Clove Rd, Millbrook, NY 12545
  • /39

    $8,800,000

    Pending
    • 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 in three

    Andrew Gates Houlihan Lawrence

    406 Shunpike, Millbrook, NY 12545
  • /30

    $22,000 Per Month

    • 3 Beds
    • 3 Baths
    • 2,264 Sq Ft
    • House for Rent

    692 Bangall Rd Unit 696, Millbrook, NY 12545

    Enjoy the summer in this furnished rental home in Millbrook. Available Memorial Day to Labor Day 2026 at $22,000 per month. Just 90 minutes north of NYC, come to enjoy the many activities this area has to offer: County Fairs, horseback riding events, local farm markets, wineries and breweries, hiking and rail trails, fantastic dining experiences and so much more. The 2,200+ square foot house has

    Susan Whalen George T Whalen Real Estate

    692 Bangall Rd Unit 696, Millbrook, NY 12545
  • 33 Upper Ln, Millbrook, NY 12545

    $775,000

    Sold Jun 29, 2026

    33 Upper Ln, Millbrook, NY 12545

    • 3 Beds
    • 3 Baths
    • 1,914 Sq Ft
    • Built 1988

    Last Sold Summary

    • 19% Above List Price
    • $405/SF
    • 34 Days On Market

    Current Estimated Value $652,815

    Last Listing Agent Susan Whalen George T Whalen Real Estate

    33 Upper Ln, Millbrook, NY 12545
  • /23

    $645,000

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft

    3875 Route 82, Millbrook, NY 12545

    Exceptionally well maintained home with many upgrades including new siding, newer roof, new hard-wired generator, new windows, new flooring on first level, newly paved driveway.Private first level includes bedroom, full eat in kitchen, living room, full bath, laundry room and separate entrance. It's the perfect for extended family living.Upstairs includes full, eat in kitchen, dining

    Valerie Foster K. Fortuna Realty, Inc.

    3875 Route 82, Millbrook, NY 12545
  • /40

    $5,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • House for Rent

    209 Route 343, Millbrook, NY 12545

    A great opportunity to escape to your own private retreat in Millbrook. This property is for rent on an annual basis and offers 3200 sq ft of living space on 10 acres of beautiful land. Featuring 3 bedrooms, 2 full baths, and 1 half bath, this residence provides ample room for comfortable living. The first floor creates an inviting atmosphere for gatherings, with spacious formal and informal

    Susan Whalen George T Whalen Real Estate

    209 Route 343, Millbrook, NY 12545
  • 4408 Route 82, Millbrook, NY 12545

    $599,000

    Sold Sep 23, 2025

    4408 Route 82, Millbrook, NY 12545

    • 3 Beds
    • 3 Baths
    • 2,436 Sq Ft
    • Built 1973

    Last Sold Summary

    • $246/SF
    • 32 Days On Market

    Current Estimated Value $613,856

    Last Listing Agent Carey Whalen Compass Greater NY, LLC

    4408 Route 82, Millbrook, NY 12545
  • /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
  • /22

    $3,500 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,277 Sq Ft
    • House for Rent

    559 Shunpike, Millbrook, NY 12545

    Charming cottage for rent in Millbrook. The light-filled interior features beautiful hardwood floors. A lovely kitchen, dining room, spacious living room, and a powder room complete the first floor. Upstairs, there are three bedrooms and a full bath. The front covered porch overlooks the beautiful yard and pond. The house is set well off the road and offers privacy. The tenant is responsible for

    Susan Whalen George T Whalen Real Estate

    559 Shunpike, Millbrook, NY 12545
  • 53 Bennett Common, Millbrook, NY 12545

    $435,000

    Sold Oct 24, 2025

    53 Bennett Common, Millbrook, NY 12545

    • 2 Beds
    • 2 Baths
    • 1,410 Sq Ft
    • Built 1965

    Last Sold Summary

    • 1% Above List Price
    • $309/SF
    • 26 Days On Market

    Current Estimated Value $423,900

    Last Listing Agent SHARON MAHAR Compass Greater NY, LLC

    53 Bennett Common, Millbrook, NY 12545
  • /24

    $895,000

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,136 Sq Ft

    35 Appaloosa Ln, Millbrook, NY 12545

    Perfectly situated at the end of a long driveway and enjoying complete privacy is this four bedroom Ranch on 8.94 +/- acres offering a picturesque setting and located only minutes to the Village of Millbrook. The lovely interior features an open floor plan with many fine details throughout such as Anderson windows, custom trim and hardwood floors. The spacious open country Kitchen is fully

    Carey Whalen Compass Greater NY, LLC

    35 Appaloosa Ln, Millbrook, NY 12545
  • /25

    $14,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • House for Rent

    11 Sutton Rd, Millbrook, NY 12545

    Set on 1.5 private acres along one of Millbrook’s most picturesque country roads, this 1950s cottage offers a quintessential Hudson Valley summer experience; equal parts relaxed, refined, and quietly beautiful. The heart of the property is the sun-filled gunite pool, perfectly sited and surrounded by leafy, pastoral views. Days unfold effortlessly here; morning swims, long afternoons in the sun,

    Ashley Whittaker Spence Compass Greater NY, LLC

    11 Sutton Rd, Millbrook, NY 12545
  • 3598 Route 82, Millbrook, NY 12545

    $1,900,000

    Sold Dec 19, 2025

    3598 Route 82, Millbrook, NY 12545

    • 3 Beds
    • 2.5 Baths
    • 4,548 Sq Ft
    • Built 1994

    Last Sold Summary

    • 12% Below List Price
    • $418/SF
    • 61 Days On Market

    Current Estimated Value $1,847,248

    Last Listing Agent Rachel Hyman-Rouse Rouse + Co Real Estate LLC

    3598 Route 82, Millbrook, NY 12545
  • /9

    $1,050,000

    • Land
    • 28.43 Acres
    • $36,933 per Acre

    TBD Woodstock Rd, Millbrook, NY 12545

    Quiet Meadow South – A rare offering of 28.43 acres of open land at the corner of Stanford Road and Woodstock Road. Bucolic field, a corner pond, and distant views create a stunning backdrop for a future homestead or agricultural endeavor. Located just outside the Village of Millbrook, this scenic parcel offers easy access with the feel of wide-open countryside. Additional land available.

    OLIVER BROWN Houlihan Lawrence Inc.

    TBD Woodstock Rd, Millbrook, NY 12545
  • /23

    $20,000 Per Month

    • 3 Beds
    • 3 Baths
    • 2,690 Sq Ft
    • House for Rent

    20 Taintor Way, Millbrook, NY 12545

    SUMMER Rental – Available August & September 2026 at $20,000 per month. This historic 1920 converted barn exudes charm and is the perfect location for a country getaway close to the Village of Millbrook. Once featured in Elle Decor Magazine, the home is tastefully furnished with primitive antique furniture and folk and modern art. A great room with soaring ceilings and fireplace, chef’s kitchen

    PAULA REDMOND Corcoran Country Living

    20 Taintor Way, Millbrook, NY 12545
  • 644 Tower Hill Rd, Millbrook, NY 12545

    $2,300,000

    Sold Apr 07, 2026

    644 Tower Hill Rd, Millbrook, NY 12545

    • 6 Beds
    • 8 Baths
    • 6,100 Sq Ft
    • Built 1909

    Last Sold Summary

    • 19% Below List Price
    • $377/SF
    • 160 Days On Market

    Current Estimated Value $2,923,398

    Last Listing Agent Byron Anderson Compass Greater NY, LLC

    644 Tower Hill Rd, Millbrook, NY 12545
  • /16

    $950,000

    • 4 Beds
    • 2 Baths
    • 3,005 Sq Ft

    41 Flint Rd, Millbrook, NY 12545

    Welcome to The Flint Road Retreat!! Beautifully maintained one-owner ranch situated on 3.53 private acres along a quiet country road, this property offers a peaceful and serene setting with plenty of room to enjoy the surrounding natural beauty, while remaining just minutes from local shops, restaurants and area amenities. The home features stunning hardwood floors, custom cherry cabinetry,

    AURA QUARTARARO William Pitt Sothebys Int Rlty

    41 Flint Rd, Millbrook, NY 12545
  • /14

    $3,850 Per Month

    • 4 Beds
    • 2 Baths
    • House for Rent

    3716 Route 44 Unit 37, Millbrook, NY 12545

    Welcome to this spacious 4-bedroom, 2-bath home set in the heart of Millbrook, just a 90 second walk to the Town Park & Pool, and in the Millbrook School District. Offering generous living spaces, hardwood floors, abundant natural light, and a large eat-in kitchen with a center island, this home provides a comfortable and functional layout for everyday living. Multiple gathering spaces,

    Joshua Schwadron CASABODE GROUP LLC

    3716 Route 44 Unit 37, Millbrook, NY 12545
  • 56 Hoof Print Rd, Millbrook, NY 12545

    $580,000

    Sold Nov 24, 2025

    56 Hoof Print Rd, Millbrook, NY 12545

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • Built 1974

    Last Sold Summary

    • 4% Above List Price
    • $276/SF
    • 26 Days On Market

    Current Estimated Value $593,119

    Last Listing Agent Jennifer Enloe Four Seasons Sothebys Intl

    56 Hoof Print Rd, Millbrook, NY 12545
  • /50

    $725,000

    $150K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    568 Oak Summit Rd, Millbrook, NY 12545

    Millbrook Modern Log Retreat sited on Nearly 3.5 Secluded Acres. Set quietly amid rolling landscape and enveloped by nature, this exquisitely restored log residence offers a rare blend of rustic authenticity and modern refinement. Perched on a knoll, the home unfolds as a serene escape—thoughtfully reimagined to deliver both comfort and understated luxury. From the moment you enter, the interiors

    Nicole Porter

    568 Oak Summit Rd, Millbrook, NY 12545
  • /9

    $2,800 Per Month

    • 1 Bed
    • 1 Bath
    • 615 Sq Ft
    • Apartment for Rent

    32 New York 343 Unit 6, Millbrook, NY 12545

    An incredible opportunity to rent a ground level completely renovated, newly FURNISHED 1-bedroom, 1 bath apartment, with private entrance and mudroom, spacious living room and lovely new kitchen within walking distance to the quaint village of Millbrook, with all its shops and restaurants, and across the road from the beautiful new Bennett Park. This charming, light-filled apartment as well as

    Ann Stettner Neil Charles Real Estate, LLC

    32 New York 343 Unit 6, Millbrook, NY 12545
  • 47 Crescent Rd, Millbrook, NY 12545

    $6,250,000

    Sold Dec 22, 2025

    47 Crescent Rd, Millbrook, NY 12545

    • 5 Beds
    • 5.5 Baths
    • 5,162 Sq Ft
    • Built 1822

    Last Sold Summary

    • 8% Below List Price
    • $1,211/SF
    • 391 Days On Market

    Last Listing Agent William Melnick Elyse Harney Real Estate

    47 Crescent Rd, Millbrook, NY 12545
    • /2

      Est $521,717

      Not Listed For Sale

      663 Shunpike, Millbrook, NY 12545

      • 3 Beds
      • 3 Baths
      • 1,540 Sq Ft
      • Built 1970
      663 Shunpike, 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
  • 1168 Bangall Amenia Rd, Millbrook, NY 12545

    $875,000

    Sold Jul 30, 2025

    1168 Bangall Amenia Rd, Millbrook, NY 12545

    • 4 Beds
    • 3 Baths
    • 2,151 Sq Ft
    • Built 1870

    Last Sold Summary

    • 7% Below List Price
    • $407/SF
    • 339 Days On Market

    Current Estimated Value $945,000

    Last Listing Agent Steve Bruman Corcoran Country Living

    1168 Bangall Amenia Rd, Millbrook, NY 12545
  • /35

    $1,295,000

    • 3 Beds
    • 2.5 Baths
    • 2,237 Sq Ft

    44 Merrit Ave, Millbrook, NY 12545

    A rare village offering on one of Millbrook’s prettiest streets, this beautifully updated three-story Victorian blends timeless character with thoughtful modern upgrades, The main residence features three bedrooms and 2.5 baths across three spacious light-filled levels, with hardwood floors throughout and classic architectural details that reflect the home’s historic roots. The welcoming living

    OLIVER BROWN Houlihan Lawrence Inc.

    44 Merrit Ave, Millbrook, NY 12545

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