Homes for Sale near Dutchess Day School

• 

  

  

  /31

  $2,850,000

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

  644 Tower Hill Rd, Millbrook, NY 12545

  A true country retreat on 109 picturesque acres on one of Millbrook’s most coveted roads, Tower Hill. This extraordinary country estate offers a rare blend of elegance, comfort, and timeless charm. The main residence, originally built in 1909 and remodeled in 2002, features five or six bedrooms, four full bathrooms, and three half bathrooms, designed for both everyday living and grand

  Byron Anderson Compass Greater NY, LLC

  644 Tower Hill Rd, Millbrook, NY 12545
• 

  Explore Dutchess Day School

• 

  

  

  /50

  $1,999,999

  • 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

  Howard Payson RE/MAX Town & Country

  3893 Route 82, Millbrook, NY 12545
• 

  

  

  /39

  $1,895,000

  • 4 Beds
  • 3 Baths
  • 3,488 Sq Ft

  425 Camby Rd, Verbank, NY 12585

  When beauty, history, tradition, and ease intersect in one lovely home, it’s 425 Camby Road. Located minutes to the Village of Millbrook on 20 private acres including two barns, two ponds, manicured and landscaped lawns, sweeping meadows, and walking paths. Classic New England charm dates back to the mid-1800s with 21st century updates, this center hall colonial conveys the warmth of generations

  Candy Anderson Compass Greater NY, LLC

  425 Camby Rd, Verbank, NY 12585
• 

  

  

  /42

  $2,850,000

  • 7 Beds
  • 6.5 Baths
  • 5,486 Sq Ft

  20 Orchard Hill Dr, Millbrook, NY 12545

  Modern Country Retreat with Iconic Hudson Valley Views Proven Investment or Private Escape Seconds from MillbrookExperience refined country life in this beautifully updated Hudson Valley home, nestled on 12+ private acres with sweeping views of the Catskill Mountains. Surrounded by lush lawns, open meadows and a fenced paddock, the property offers a sense of serenity, space, and

  Kathryn Johnson William Pitt Sotheby's Interna

  20 Orchard Hill Dr, Millbrook, NY 12545
• 

  

  

  /29

  $1,950,000

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

  3598 Route 82, Millbrook, NY 12545

  Just a mile and a half south of Millbrook Village, along the scenic stretch of Route 82 where farmland unfolds and county views stretch for miles, a tree-lined driveway winds back from the road to reveal a distinguished country estate. Built in the mid-1990s yet styled with timeless character, this Second Empire Victorian home showcases a sweeping wraparound porch, a classic mansard roof, and

  Rachel Hyman-Rouse Rouse + Co Real Estate LLC

  3598 Route 82, Millbrook, NY 12545
• 

  

  /36

  $3,500,000

  • 5 Beds
  • 4.5 Baths
  • 4,972 Sq Ft

  0 Wing Rd, Washington, NY 12545

  The artistry of Coole Park is in the way it unfolds from the center. Two gracious wings on either side of the original 1888 house create an architectural triptych that conveys elegance and comfort in equal measure. Warm wide board floors, soaring French doors, six working fireplaces, and numerous demi-lune windows create a sense of space and style as well as history. To the right of the entryway,

  Candy Anderson Compass Greater NY, LLC

  0 Wing Rd, Washington, NY 12545
• 

  

  /50

  $5,500,000

  • 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
• 

  

  /39

  $5,900,000

  • 6 Beds
  • 9 Baths
  • 8,117 Sq Ft

  465 Shunpike, Millbrook, NY 12545

  Be transcended into refined elegance. This stately home is an entertainer's dream. Set at the end of a picturesque, tree-lined drive on 40 serene acres, it offers a harmonious blend of historic elegance and contemporary living. The main house, which dates back to the late 1800s, has been thoughtfully updated and retains much of its period detail and charm with an updated twist. The four barns

  Kyle Irwin Corcoran Country Living

  465 Shunpike, Millbrook, NY 12545
• 

  

  /13

  $4,675,000

  • 4 Beds
  • 4.5 Baths
  • 4,024 Sq Ft

  114 Brush Hill Rd, Millbrook, NY 12545

  Brush Hill Contemporary is a to-be-built masterpiece in the Hudson Valley with an inviting and expansive floor plan designed to allow freedom to roam with absolute comfort and luxury. Huge southerly views of the Clove Valley, and beyond, through floor to ceiling windows in the public spaces allow for maximum light and an indoor/outdoor flow that enhances every season. The home will consist of

  Byron Anderson Compass Greater NY, LLC

  114 Brush Hill Rd, Millbrook, NY 12545
• 

  /2

  $625,000

  28 On the Green, Verbank, NY 12585

  Prime Four-Unit Investment Opportunity, cash Flow Positive 4-Plex with Significant Value-Add Potential.Invest in a fully-occupied, turn-key four-unit building offering immediate income and substantial long-term value. This is a rare opportunity to acquire a stabilized asset in a rapidly appreciating neighborhood with predictable cash flow from day one. There are two- 2 bedroom apartment, one

  Diana Lenz Houlihan Lawrence Inc.

  28 On the Green, Verbank, NY 12585
• 

  

  /3

  $445,000

  3406 Route 82, Verbank, NY 12585

  Discover the ideal investment opportunity or live-in-and-rent scenario with this well-maintained two-family home. Offering reliable cash flow and a prime location, this property is perfect for savvy investors or those looking to offset their mortgage with rental income. This home consists of one - 2 bedroom apartment and a studio. Previously a three family there is an additional area that used

  Diana Lenz Houlihan Lawrence Inc.

  3406 Route 82, Verbank, NY 12585
• 

  

  /45

  $900,000

  • 4 Beds
  • 6.5 Baths
  • 5,050 Sq Ft

  3534 Route 82, Millbrook, NY 12545

  Discover a truly unique Millbrook estate set on over 6 acres with a private pond, fruit trees, and beautiful natural surroundings. This expansive stone and brick residence offers remarkable craftsmanship and imported finishes, including marble and other materials brought in directly from Italy. Designed for both elegance and comfort, the home features multiple kitchens, two formal dining rooms,

  Christian Baez Keller Williams Hudson Valley

  3534 Route 82, Millbrook, NY 12545
• 

  

  /50

  $875,000

  • 3 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  568 Oak Summit Rd, Millbrook, NY 12545

  Millbrook Modern Log Home on Nearly 3.5 Private AcresTucked away on rolling, private property, this bright and airy genuine log home has been completely reimagined and restored from top to bottom—inside and out.Step inside to find a floor-to-ceiling wood-burning fireplace, an open-concept layout, and abundant natural light throughout. Every room has been fully renovated, with reinforced

  Nicole Porter

  568 Oak Summit Rd, Millbrook, NY 12545
• 

  

  /27

  $11,995,000

  • 9 Beds
  • 9.5 Baths
  • 13,737 Sq Ft

  121-125 Butts Hollow Rd, Millbrook, NY 12545

  Perched above the bucolic rolling hills of Millbrook Hunt Country, framed by panoramic views of the Catskill mountains sits an idyllic country retreat and extraordinary equestrian estate encompassing 185 ultra-private acres. Once the cherished estate of Margaret Carnegie, only child of Andrew Carnegie, a rich legacy of elegance and prestige is preserved and embraced throughout this iconic

  John Oliveira Douglas Elliman Real Estate

  121-125 Butts Hollow Rd, Millbrook, NY 12545
• 

  

  /23

  $375,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  54 Bennett Common, Millbrook, NY 12545

  Welcome to Bennett Commons, the new “In” place to live! Now surrounded by the beautiful 35 acre Bennett Park. Enjoy an abundance of nature with breathtaking views right in your backyard. This 2 bedroom, 2 bath condo features hardwood floors, an eat-in-kitchen and formal dining room. The living room offers an elegant wood burning fireplace with sliding glass doors leading to a spacious deck

  THERESA MAGGIACOMO Theresa A. Maggiacomo

  54 Bennett Common, Millbrook, NY 12545
• 

  

  /39

  $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 in three

  Andrew Gates Houlihan Lawrence

  406 Shunpike, Millbrook, NY 12545
• 

  

  /25

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 1,886 Sq Ft

  11 Sutton Rd, Millbrook, NY 12545

  Tucked away on 1.5 acres along one of Dutchess County's most scenic roads, this 1950’s Millbrook cottage is the definition of charm and style. A true designer’s dream. The home blends storybook character with sophisticated updates, offering both warmth and polish in every room.Inside, light-filled spaces invite gathering and quiet retreat alike. The home offers 3 bedrooms and 2 full

  Ashley Whittaker Spence Compass Greater NY, LLC

  11 Sutton Rd, Millbrook, NY 12545
• 

  

  /41

  $510,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,230 Sq Ft

  487 Chestnut Ridge Rd, Dover Plains, NY 12522

  Located in Dover Plains, this charming 3-bedroom, 2-bath Colonial offers 2,230 sq. ft. of living space on a 1.27-acre corner lot and includes a detached 2-car garage. Inside, you’ll find an inviting open-concept layout. The main level is perfect for entertaining or everyday living and features a spacious living room with hardwood floors, a large dining room that flows seamlessly to an eat-in

  Robert Washburn RE/MAX Ace Realty

  487 Chestnut Ridge Rd, Dover Plains, NY 12522
• 

  

  /33

  $315,000

  • 3 Beds
  • 1 Bath
  • 1,476 Sq Ft

  40 Glen Ave, Dover Plains, NY 12522

  Welcome to 40 Glen Avenue, a lovingly maintained 3 bedroom, 1 bath single family home located on a low-traffic, dead-end road in Dover Plains, NY. Offering 1,476 square feet of comfortable one level living on nearly half an acre, this home blends charm, thoughtful updates, and great potential. Inside, you'll find hardwood floors, an updated bathroom, a large mudroom, and a flexible den currently

  Robert Brestovansky eXp Realty

  40 Glen Ave, Dover Plains, NY 12522
• 

  

  /50

  $1,399,999

  • 6 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  57 Cedar Berry Ln, Dover Plains, NY 12522

  Just 90 miles from New York City, at the end of a winding, tree-lined drive, a world unfolds where time slows down, and life takes on a different rhythm. This is the Hudson Valley escape you’ve been waiting for. A custom-built home with detached workshop on nearly five private acres, where every detail was designed to bring comfort, inspiration, and beauty into daily living.The moment you

  Lindsay Stevens eXp Realty

  57 Cedar Berry Ln, Dover Plains, NY 12522
• 

  

  /40

  $599,000

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  89 Deer Pond Rd, Verbank, NY 12585

  Privately situated on 4 acres and at the end of a quiet cul-de-sac, find this custom contemporary. Complete with stocked pond, inground pool & massive three bay barn, this unique property will surely impress. Attractive floor plan features kitchen w/sunroom annex overlooking the expansive backyard. Living room w/fireplace flows seamlessly to secondary sunroom & family room w/bar. Huge first floor

  Dan Axtmann BHHS Hudson Valley Properties

  89 Deer Pond Rd, Verbank, NY 12585
• 

  

  /42

  $13,500,000

  • 5 Beds
  • 8 Baths
  • 5,867 Sq Ft

  1190 Chestnut Ridge Rd, Dover Plains, NY 12522

  A singular and exceedingly rare residence, this exquisite home was masterfully designed by renowned AD100 architect Gil Schafer, featuring interiors by Antony Todd and landscape architecture by Warren Byrd, all set against panoramic views of the Hudson Valley and Catskill Mountains. This home is a Greek Revival masterpiece that blends timeless elegance with modern sophistication. As featured in

  OLIVER BROWN Houlihan Lawrence Inc.

  1190 Chestnut Ridge Rd, Dover Plains, NY 12522
• 

  

  /34

  $990,000

  • 4 Beds
  • 4 Baths
  • 3,506 Sq Ft

  121 Valley Farm Rd, Millbrook, NY 12545

  This unique timberframe home is welcoming, spacious, and awaiting your personal touch! Tucked back off the road on 7 private acres, this property has so many special features, including an outdoor, covered patio with kitchen, pizza oven and fireplace, a traditional red barn, and another large outbuilding with heat and electricity - the perfect place for your special hobby - whether it be cars,

  THERESA GILL Legacy Land & Homes LLC

  121 Valley Farm Rd, Millbrook, NY 12545
• 

  

  /23

  $110,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  151 Scott Dr, Dover Plains, NY 12522

  Beautiful Home in the Tally Ho Senior Community!Nestled on a premium lot, this charming and spacious home offers comfortable living in the desirable Tally Ho 55+ community. Step into the bright and open living room, dining area, and kitchen, all featuring vaulted ceilings that enhance the sense of space and light. The large kitchen is a chef’s dream, boasting abundant cabinetry and

  Blake Michaud Serhant LLC

  151 Scott Dr, Dover Plains, NY 12522
• 

  

  /31

  $665,000

  • 3 Beds
  • 4 Baths
  • 3,633 Sq Ft

  30 Eddy Rd, Verbank, NY 12585

  Welcome to 30 Eddy Road, a stunning contemporary residence nestled on a generous 1.17-acre lot in the serene Town of Union Vale. This meticulously maintained home boasts gleaming hardwood floors throughout, creating a warm and inviting atmosphere from the moment you step inside.The open-concept living and dining areas feature soaring ceilings accented by rustic wooden beams and expansive

  Robert Chiappone Century 21 Hire Realty

  30 Eddy Rd, Verbank, NY 12585
• 

  

  /3

  $79,000

  • Land
  • 1.49 Acres
  • $53,020 per Acre

  0 Tinker Town Rd, Dover Plains, NY 12522

  Escape the NYC and come to see THIS MIX USE 1.49 acre lot in Amenia, NY. Nestled in the beautiful Dutchess County, this level plot offers endless possibilities for those looking to build a custom home or business or both. This property provides a canvas for your dreams . A Natural Haven Just Minutes from Modern Conveniences, The lots proximity to the Taconic State Parkway and the Dover Plains

  Adnane Chahi Keller Williams Realty Partner

  0 Tinker Town Rd, Dover Plains, NY 12522
• 

  

  /27

  $1,150,000

  • 2 Beds
  • 1 Bath
  • 1,216 Sq Ft

  447 Butts Hollow Rd, Dover Plains, NY 12522

  It seems to be a human instinct to define utopia as a garden, and this Millbrook property on Butts Hollow Road unequivocally deserves that designation. Not only gardens—which have been lovingly created and curated—but meadows and forest glens, falling water and meandering paths. Regardless of season, there is always something unexpected and lovely to greet you—a rippling sea of red poppies,

  Candy Anderson Compass Greater NY, LLC

  447 Butts Hollow Rd, Dover Plains, NY 12522
• 

  

  /51

  $19,995,000

  • 7 Beds
  • 9 Baths
  • 11,970 Sq Ft

  309 Woodstock Rd, Millbrook, NY 12545

  Presenting Canoe Hill, a remarkable 63-acre estate and vineyard in the heart of Millbrook, New York. This extraordinary property stands as a testament to architectural evolution, where a storied mid-1700s colonial core has been thoughtfully expanded to create a remarkable 12,650 SF main residence that seamlessly marries Colonial, Georgian and Greek Revival influences. Two significant expansions,

  Jason Karadus Corcoran Country Living

  309 Woodstock Rd, Millbrook, NY 12545
• 

  /2

  $100,000

  • Land
  • 0.83 Acre
  • $120,482 per Acre

  9 Terbar Ct, Dover Plains, NY 12522

  Beautiful flat building lot, no clearing needed! Board of health approved for 4 bedroom home and you only need a small septic on this lot which makes building a home here more cost effective! This level lot is perfect to build your dream home. Bring your own builder or use ours! We can help and assist the first time homebuyer build their dream home through the whole process.

  Bliss Voutsinas

  9 Terbar Ct, Dover Plains, NY 12522
• 

  

  /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
• 

  

  /46

  $1,495,000

  • 4 Beds
  • 3 Baths
  • 3,228 Sq Ft

  508 Woodstock Rd, Millbrook, NY 12545

  On a country road overlooking a beautiful spring-fed pond sits a 3,228 sq ft cedar-sided traditional home. Set on 23 stunning acres of open fields, mature trees, and bucolic landscaping, just outside from the Village of Millbrook. Inside, the home features a spacious and flexible layout with 4 bedrooms, 3 full baths, central A/C, and a gas fireplace. The upper level welcomes you into an open

  OLIVER BROWN Houlihan Lawrence Inc.

  508 Woodstock Rd, Millbrook, NY 12545
• 

  

  /8

  $375,000

  • Land
  • 10.09 Acres
  • $37,166 per Acre

  519 Woodstock Rd, Millbrook, NY 12545

  Rolling Hills Farm - Set along a scenic road just minutes from Millbrook Village, this 10.09-acre parcel offers open fields, rolling hills, and a rural backdrop. With an approved building envelope and access from Stanford Road, it's an ideal setting for a future home or private retreat. Located in a highly desirable area, this property presents a rare opportunity to build in a sought-after

  OLIVER BROWN Houlihan Lawrence Inc.

  519 Woodstock Rd, Millbrook, NY 12545
• 

  

  /9

  $1,050,000

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

  521 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.

  521 Woodstock Rd, Millbrook, NY 12545
• 

  

  /32

  $1,750,000

  • 5 Beds
  • 4 Baths
  • 4,410 Sq Ft

  645 Tyrrel Rd, Millbrook, NY 12545

  This historic home was originally built in Millbrook, New York in 1733 by one of the nine partners of the early English land grant. The carefully maintained original architectural features reflect its heritage. On 10 ½ acres the property is a mixture of meadows and woods and bordered on 2 sides by a year round running stream. Clipped lawns surround the house and a privately situated

  HEATHER CRONER William Pitt Sothebys Int Rlty

  645 Tyrrel Rd, Millbrook, NY 12545
• 

  

  /47

  $750,000

  • 4 Beds
  • 4.5 Baths
  • 3,895 Sq Ft

  17 Washington Ave, Millbrook, NY 12545

  Timeless Elegance for Exceptional Living in this Expansive Home crafted by Italian Stone Masons in 1910, previously known as the Porter House Inn in the Heart of Millbrook Village.This imposing 4,000 sf home lives even larger with a walk-up windowed attic on the third floor and full walk-out basement below, and further still with gracious covered porches on the front of the house and

  Norm Mackay

  17 Washington Ave, Millbrook, NY 12545
• 

  

  /33

  $12,500,000

  • 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
• 

  

  /43

  $20,000,000

  • 4 Beds
  • 8 Baths
  • 7,500 Sq Ft

  365-381 Tower Hill Rd, Wassaic, NY 12592

  A Private Architectural Masterpiece on 165 AcresNestled along the border of Amenia and Millbrook, NY, this extraordinary 165-acre estate offers unparalleled privacy and breathtaking panoramic views of the Hudson Valley. Designed by the acclaimed Resolution: 4 Architecture and completed in 2019, the 7,500-square-foot modern residence harmonizes seamlessly with its natural

  Noble Black Douglas Elliman Real Estate

  365-381 Tower Hill Rd, Wassaic, NY 12592
• 

  

  /9

  $1,075,000

  • Land
  • 86 Acres
  • $12,500 per Acre

  Northrup Northrup Rd, Dover, NY 12522

  A special property for someone seeking a quiet private location to create an estate with great view potential. The property is grown over but offers approximately 4o plus or minus acres of crop land if and when reclaimed. High elevations -highest point is 1050 feet. Excellent location, conveniently situated to Millbrook Village, Amenia Village, Kent, Ct., and only two miles to the Hamlet of

  Robert D Ferris R. Ferris Real Estate, LLC

  Northrup Northrup Rd, Dover, NY 12522
• 

  

  /19

  $165,000

  • Land
  • 5.1 Acres
  • $32,353 per Acre

  565 Halls Corners Rd, Dover Plains, NY 12522

  Builder's Dream... A lot was Completed on this Property, survey, well, electric, foundation started, driveway started and more. Build your DREAMHOME on this Beautiful Magnificent Property with BOHA 5.1 acre lot. Many Permits are Completed. Well/ Septic and plans are Board of HealthApproved for a 3 Bedroom home, valid thru July 2027. Completed projects include: Survey. 1+ acre building

  Helen Sclafani World Homes Realty

  565 Halls Corners Rd, Dover Plains, NY 12522
• 

  

  /36

  $1,450,000

  • 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

Showing Results 1 - 40, Page 1 of 2