40

Homes for Sale near Dutchess Day School

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  • /12

    $3,850,000

    • 4 Beds
    • 4.5 Baths
    • 3,542 Sq Ft

    114 Brush Hill Rd, Millbrook, NY 12545

    Perched above the Clove Valley just minutes from the Village of Millbrook, this exceptional modern residence is designed to celebrate light, landscape, and elevated living in the heart of the Hudson Valley. Set on 51.38 acres of rolling countryside, the home offers breathtaking, panoramic views and a rare sense of privacy, while remaining conveniently close to village amenities. The proposed

    Byron Anderson Compass Greater NY, LLC

    114 Brush Hill Rd, 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
  • /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
  • /19

    $159,000

    • Land
    • 5.1 Acres
    • $31,176 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
  • /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
  • /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
  • /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
  • /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
  • /5

    $944,900

    • 4 Beds
    • 2.5 Baths
    • 2,829 Sq Ft

    37 Maple Hill Dr, Millbrook, NY 12545

    This to-be-built Mayfair style home will be located in Hidden Glen, Millbrook's newest Luxury Community, featuring eight custom residences set on gorgeous one+ acre, level, tree-lined homesites. This popular design offers 2,829 square feet of beautifully crafted living space and upscale finishes throughout. A grand two-story entry foyer leads to an open kitchen and breakfast area overlooking the

    TINA TOWNSEND BHHS Hudson Valley Properties

    37 Maple Hill Dr, Millbrook, NY 12545
  • /21

    $7,900,000

    • Land
    • 441.99 Acres
    • $17,874 per Acre

    1297 New York 343, Dover Plains, NY 12522

    Nestled in the heart of natural beauty, this extraordinary property offers over 440 acres of pristine land in the municipality of Washington. A rare find, this expansive tract of land is a harmonious blend of rolling hay fields, lush pastures, mature hardwood forests, three tranquil ponds and meandering stream. The property rises from east to west, providing breathtaking views across the Harlem

    Brian McGrath McGrath Realty Inc

    1297 New York 343, Dover Plains, NY 12522
  • /8

    $1,069,000

    • 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
  • /34

    $389,000

    • 5 Beds
    • 2 Baths
    • 2,100 Sq Ft

    14-16 Glen Hill, Dover Plains, NY 12522

    An affordable multifamily compound in the quiet hamlet of Dover Plains—an increasingly rare opportunity to own two homes for the price of one. This unique property features a 3-bedroom/1-bath residence and a separate 2-bedroom/1-bath home, both in solid condition with some TLC needed to make them your own. Set on a picturesque parcel at the end of a country road, the setting is peaceful, private,

    Barry Malawer Coldwell Banker Realty

    14-16 Glen Hill, Dover Plains, NY 12522
  • /5

    $954,000

    • 3 Beds
    • 2 Baths
    • 2,030 Sq Ft

    66 County House Rd, Millbrook, NY 12545

    Introducing Millbrook's newest luxury community, Hidden Glen at Millbrook, offering eight custom residences set on gorgeous one+ acre, level tree-lined homesites. The Rochester ranch-style home is positioned on a premium lot and offers 2,030 square feet of convenient one-level living. The foyer opens to a dramatic family room with volume ceilings, flowing seamlessly into the kitchen with huge

    Brian Mossey BHHS Hudson Valley Properties

    66 County House Rd, Millbrook, NY 12545
  • /8

    $375,000

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

    TBD Stanford 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.

    TBD Stanford Rd, Millbrook, NY 12545
  • /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 Millbrook Experience 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 elevated living—

    Kathryn Johnson William Pitt Sotheby's Interna

    20 Orchard Hill Dr, Millbrook, NY 12545
  • /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
  • /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
  • /11

    $190,000

    • Land
    • 1.66 Acres
    • $114,458 per Acre

    0 New York 22, Dover Plains, NY 12522

    Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /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
  • /10

    $1,200,000

    • Land
    • 51.38 Acres
    • $23,355 per Acre

    0 Brush Hill Rd Unit KEY935753, Union Vale, NY 12545

    A stunning 51+ acre parcel offering complete privacy and sweeping long views of the Clove Valley, this idyllic setting is the perfect canvas for your dream retreat. A beautiful blend of open meadow and wooded landscape, the land features both level and gently sloping terrain, highlighted by a seasonal stream and ample space to create your own trail system for recreation, exploration, or nature

    Byron Anderson Compass Greater NY, LLC

    0 Brush Hill Rd Unit KEY935753, Union Vale, NY 12545
  • /39

    $545,000

    • 2 Beds
    • 2 Baths
    • 1,598 Sq Ft

    121 Stanford Rd, Millbrook, NY 12545

    Here is a rare opportunity to acquire a slice of Millbrook history. The original Millbrook Toll House Circa 1890, built alongside the Wappingers Creek at the Arch Bridge is a true gem. The Toll House has been lovingly restored, preserved, and maintained, with an utmost respect for its grace, integrity and historical significance. Exposed beams/hardwood pristine, whimsical nooks and crannies

    Terese Mondello MONDELLO UPSTATE PROPERTIES LLC

    121 Stanford 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 Hillside Realty & Development

    9 Terbar Ct, Dover Plains, NY 12522
  • /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
  • /11

    $205,000

    • Land
    • 2.5 Acres
    • $82,000 per Acre

    0 New York 22, Dover Plains, NY 12522

    Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /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
  • /11

    $195,000

    • Land
    • 1.85 Acres
    • $105,405 per Acre

    0 New York 22, Dover Plains, NY 12522

    Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /30

    $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

    Stacey Pinkas Douglas Elliman Real Estate

    121-125 Butts Hollow Rd, Millbrook, NY 12545
  • /11

    $975,000

    • 3 Beds
    • 2.5 Baths
    • 2,426 Sq Ft

    477 Canoe Hill Rd, Millbrook, NY 12545

    Early Country Cottage on 5 acres on a quiet country road in Millbrook, 5 minutes from the village. An excellent fishing stream borders the property. 3 bedrooms, 2 ½ bathrooms. Wood burning fireplaces in kitchen, living room and dining room. Barns. Additional Information: HeatingFuel:Oil Above Ground,

    HEATHER CRONER William Pitt Sothebys Int Rlty

    477 Canoe Hill Rd, Millbrook, NY 12545
  • /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
  • /31

    $649,000

    • 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
  • /2

    $119,000

    • Land
    • 13.31 Acres
    • $8,941 per Acre

    0 Cart Rd Unit KEY833895, Dover, NY 12522

    Nice wooded property with frontage on Cart Rd and 343. Ideal for camp or your hunting cabin. Beautiful view of the town. Priced to sell. 40+ acres also for sale, next to it.

    Graziano Tassone Tassone Realty Corp.

    0 Cart Rd Unit KEY833895, Dover, NY 12522
  • /48

    $3,750,000

    • 3 Beds
    • 5 Baths
    • 4,134 Sq Ft

    97 Valley Farm Rd, Millbrook, NY 12545

    New, never lived in, move in ready, almost 20 acres, just outside the Village of Millbrook, stunning, fully remodeled total renovation (both inside and out), country property with the most gorgeous sweeping Catskill Mountain Views. No expense was spared. Pure luxury inside and out. Inside: All brand new: windows, doors, heating & cooling system, plumbing and electrical, water purification system,

    Susan Whalen George T Whalen Real Estate

    97 Valley Farm 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
  • /39

    $1,400,000

    • 5 Beds
    • 4 Baths
    • 3,306 Sq Ft

    645 Tyrrel Rd, Millbrook, NY 12545

    Step back in time and experience this historic farm house which has been renovated with great attention to period details such as restored wide board flooring, beautiful reconditioned woodwork, exposed beams and 4 fireplaces. There are 5 bedrooms, one of which is ensuite and on the first floor and 3 other full baths. With formal living and dining rooms, office, and a large light filled family

    ANN WILKINSON Compass Greater NY, LLC

    645 Tyrrel Rd, Millbrook, NY 12545
  • /51

    $19,995,000

    • 7 Beds
    • 9 Baths
    • 12,659 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
  • /41

    $480,000 Open Sun 1PM - 3PM

    • 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
  • /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
  • /42

    $319,999

    • 3 Baths

    703 Butts Hollow Rd, Dover Plains, NY 12522

    Discover an incredible investment opportunity in highly desirable Dover Plains! This multi-family property sits on a beautiful, private lot just shy of an acre, offering endless potential for expansion, added income, or future development. Surrounded by a serene landscape and located in a prime location, this property appeals to both investors and end-users alike. Whether you’re looking to

    German Nielsen Newman Realty Inc

    703 Butts Hollow Rd, Dover Plains, NY 12522
  • /44

    $2,475,000

    • 4 Beds
    • 4.5 Baths
    • 2,412 Sq Ft

    56 Northrup Rd, Dover Plains, NY 12522

    At the very end of a quiet country road, you'll find 56 Northrup — a stunning, architect-designed retreat blending 19th-century farmhouse charm with thoughtful, award-winning modern design. Originally built in 1870 and reimagined by NYC architects Neumann & Rudy, this 33-acre property includes a restored main house, a sleek single-story primary suite addition, and expansive grounds featuring a

    Adam Hade Compass Greater NY, LLC

    56 Northrup Rd, Dover Plains, NY 12522
  • /27

    $11,995,000

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

    121 Butts Hollow Rd, Dover Plains, NY 12522

    Perched above the rolling hills of Millbrook Hunt Country with sweeping Catskill Mountain views, this idyllic retreat and exceptional equestrian estate spans 185 ultra-private acres. Once the beloved property of Margaret Carnegie, only child of Andrew Carnegie, the estate preserves a rich legacy of elegance and prestige. Originally built in 1865, it has been thoughtfully expanded to blend

    John Oliveira Douglas Elliman of Connecticut

    121 Butts Hollow Rd, Dover Plains, NY 12522
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