1,975

Millbrook, NY Homes

Section Image
  • /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
  • /10

    $1,350

    Total Monthly Price

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

    11 Washington Ave Unit 3, Millbrook, NY 12545

    Bright 1 bedroom apartment on second floor of a small apartment house in beautiful village of Millbrook. Walking distance to all shops. Apartment has been newly renovated. Rent is $1350 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 allowed.

    11 Washington Ave Unit 3, 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
    • 29 Merrit Ave, Millbrook, NY 12545

      Not Listed For Sale

      29 Merrit Ave, Millbrook, NY 12545

      • 5 Beds
      • 3.5 Baths
      • 2,584 Sq Ft
      • Built 1930
      29 Merrit Ave, Millbrook, NY 12545

      Last Sold Summary

      • 265 Days On Market

      Last Listing Agent Lydia Hendricks Weichert Realtors

  • /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
  • /15

    $1,850 Per Month

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Apartment for Rent

    22 Washington Ave 2nd, V. Millbrook, NY 12545

    GREAT 2ND FLOOR APARTMENT IN THE HEART OF THE VILLAGE OF MILLBROOK. IT FEATURES A BRIGHT LIVING ROOM, KITCHEN, TWO BEDROOMS, FULL BATH AND LAUNDRY ROOM WITH FULL SIZE WASHER AND DRYER. WITHIN WALKING DISTANCE OF ALL THE VILLAGE HAS TO OFFER. ONE CAR GARAGE SPACE IS INCLUDED. PETS ARE NOT PERMITTED. TENANT IS RESPONSIBLE FOR ALL UTILITIES.

    George Whalen III George T Whalen Real Estate

    22 Washington Ave 2nd, V. 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 $664,471

    Last Listing Agent Diana Wiemer Houlihan Lawrence Inc.

    786 N Clove Rd, Millbrook, NY 12545
    • 60-62 Old Route 82, Millbrook, NY 12545

      Not Listed For Sale

      60-62 Old Route 82, Millbrook, NY 12545

      • 4 Beds
      • 4.5 Baths
      • 2,982 Sq Ft
      • Built 1900
      60-62 Old Route 82, Millbrook, NY 12545

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Liza Reiss Elyse Harney Real Estate

  • /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
  • /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
  • 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 $611,779

    Last Listing Agent Susan Whalen George T Whalen Real Estate

    33 Upper Ln, Millbrook, NY 12545
    • 296 Stanford Rd Unit 302, Millbrook, NY 12545

      Not Listed For Sale

      296 Stanford Rd Unit 302, Millbrook, NY 12545

      • 5 Beds
      • 6 Baths
      • 5,514 Sq Ft
      • Built 1986
      296 Stanford Rd Unit 302, Millbrook, NY 12545

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Brian Smith River Realty Services, Inc.

  • /36

    $615,000

    $80K 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
  • /21

    $9,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 4,746 Sq Ft
    • House for Rent

    72 N Mabbettsville Rd, Millbrook, NY 12545

    This contemporary farmhouse on a sprawling property offers extreme privacy just minutes from the village of Millbrook. North Mabbettsville Road is a coveted location, and this property offers trails for hiking and cross country skiing as well as proximity to a range of outdoor activities. Enjoy peaceful pastoral views from the home's wrap-around porch or relax in the heated pool. This graciously

    Candy Anderson Compass Greater NY, LLC

    72 N Mabbettsville Rd, 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 $558,587

    Last Listing Agent Carey Whalen Compass Greater NY, LLC

    4408 Route 82, Millbrook, NY 12545
    • 4318 Route 44, Millbrook, NY 12545

      Est $2,158,821

      Not Listed For Sale

      4318 Route 44, Millbrook, NY 12545

      • 3 Beds
      • 3.5 Baths
      • 3,598 Sq Ft
      • Built 1930
      4318 Route 44, Millbrook, NY 12545

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Candy Anderson Compass Greater NY, LLC

  • /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
  • /16

    $1,500 Per Month

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

    12 Alden Place Unit 2, Millbrook, NY 12545

    Renovated one bedroom apartment in the charming Village of Millbrook. The apartment has been completely repainted. This is a first floor unit in a multi-family home. Off street parking is available from this convenient village location that is within walking distance to grocery store, shops, restaurants, parks, public tennis courts and library. No smoking unit. No pets allowed. Shared laundry in

    Susan Whalen George T Whalen Real Estate

    12 Alden Place Unit 2, 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 $434,270

    Last Listing Agent SHARON MAHAR Compass Greater NY, LLC

    53 Bennett Common, Millbrook, NY 12545
    • 1215 Shunpike, Millbrook, NY 12545

      Est $794,026

      Not Listed For Sale

      1215 Shunpike, Millbrook, NY 12545

      • 4 Beds
      • 4 Baths
      • 3,516 Sq Ft
      • Built 1940
      1215 Shunpike, Millbrook, NY 12545

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Brian Smith River Realty Services, Inc.

  • /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
  • /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
  • 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 $1,843,176

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

    3598 Route 82, Millbrook, NY 12545
    • 26 Trebor Trail, Millbrook, NY 12545

      Est $606,711

      Not Listed For Sale

      26 Trebor Trail, Millbrook, NY 12545

      • 2 Beds
      • 2 Baths
      • 1,932 Sq Ft
      • Built 1988
      26 Trebor Trail, Millbrook, NY 12545

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent PAULA REDMOND Corcoran Country Living

  • /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
  • /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 $2,468,146

    Last Listing Agent Byron Anderson Compass Greater NY, LLC

    644 Tower Hill Rd, Millbrook, NY 12545
    • 128 Bangall Rd, Millbrook, NY 12545

      Est $913,751

      Not Listed For Sale

      128 Bangall Rd, Millbrook, NY 12545

      • 4 Beds
      • 2.5 Baths
      • 2,520 Sq Ft
      • Built 1980
      128 Bangall Rd, Millbrook, NY 12545

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Susan Whalen George T Whalen Real Estate

  • /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
  • /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
  • 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 $601,788

    Last Listing Agent Jennifer Enloe Four Seasons Sothebys Intl

    56 Hoof Print Rd, Millbrook, NY 12545
    • 59 Bangall Rd, Millbrook, NY 12545

      Est $2,017,377

      Not Listed For Sale

      59 Bangall Rd, Millbrook, NY 12545

      • 4 Beds
      • 5 Baths
      • 5,086 Sq Ft
      • Built 1999
      59 Bangall Rd, Millbrook, NY 12545

      Last Sold Summary

      • 101 Days On Market

      Last Listing Agent Susan Whalen George T Whalen Real Estate

  • /35

    $1,295,000

    Pending
    • 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
  • 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
    • 620 Route 343, Millbrook, NY 12545

      Est $766,276

      Not Listed For Sale

      620 Route 343, Millbrook, NY 12545

      • 2 Beds
      • 1.5 Baths
      • 1,500 Sq Ft
      • Built 1930
      620 Route 343, Millbrook, NY 12545

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Kyle Irwin Corcoran Country Living

  • /6

    $1,098,500

    New Construction $154K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 2,993 Sq Ft

    37 Maple Hill Dr, Millbrook, NY 12545

    Under Construction - Mayfair model with popular upgrades throughout, located in Hidden Glen, Millbrook's newest Luxury Community. Featuring eight custom residences set on gorgeous one+ acre, level, tree-lined homesites. This floor plan and design offers 2,993 square feet of beautifully crafted living space and upscale finishes throughout. A grand two-story entry foyer leads to an open kitchen and

    TINA TOWNSEND BHHS Hudson Valley Properties

    37 Maple Hill Dr, Millbrook, NY 12545
  • 611 N Clove Rd, Millbrook, NY 12545

    $849,000

    Sold Aug 13, 2026

    611 N Clove Rd, Millbrook, NY 12545

    • 3 Beds
    • 3 Baths
    • 2,033 Sq Ft
    • Built 1950

    Last Sold Summary

    • 9% Below List Price
    • $418/SF
    • 79 Days On Market

    Current Estimated Value $834,185

    Last Listing Agent PAULA REDMOND Corcoran Country Living

    611 N Clove Rd, Millbrook, NY 12545
    • 309 Route 343, Millbrook, NY 12545

      Est $2,340,844

      Not Listed For Sale

      309 Route 343, Millbrook, NY 12545

      • 4 Beds
      • 4 Baths
      • 2,790 Sq Ft
      • Built 1970
      309 Route 343, Millbrook, NY 12545

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl

  • /47

    $1,069,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,001 Sq Ft

    45 Maple Hill Dr, Millbrook, NY 12545

    Introducing the first home in Hidden Glen, Millbrook's Newest Luxury Community, featuring eight custom residences set on gorgeous one+ acre, level tree-lined homesites. This Millbrook Design offers 3,001 square feet of expertly crafted living space, featuring custom design and upscale finishes throughout. Located within the highly regarded Millbrook School District, this elegant new construction

    TINA TOWNSEND BHHS Hudson Valley Properties

    45 Maple Hill Dr, Millbrook, NY 12545
  • /39

    $5,775,000

    Sold Mar 11, 2026

    465 Shunpike, Millbrook, NY 12545

    • 6 Beds
    • 9 Baths
    • 8,177 Sq Ft
    • Built 1900

    Last Sold Summary

    • 14% Below List Price
    • $706/SF
    • 0 Days On Market

    Current Estimated Value $5,692,377

    Last Listing Agent Kyle Irwin Corcoran Country Living

    465 Shunpike, Millbrook, NY 12545

Showing Results 1 - 40, Page 1 of 18

How to Buy a Home How to Finance a Home How to Sell a Home