Homes for Sale near Dutchess Day School

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  /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
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  Explore Dutchess Day School

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  /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
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  /50

  $2,200,000

  • 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 and a

  Howard Payson RE/MAX Town & Country

  3893 Route 82, Millbrook, NY 12545
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  /47

  $2,700,000

  • 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 Sothebys Int Rlty

  20 Orchard Hill Dr, Millbrook, NY 12545
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  /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
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  /45

  $3,900,000

  • 6 Beds
  • 7.5 Baths
  • 7,460 Sq Ft

  259 Woodstock Rd, Millbrook, NY 12545

  Peace and tranquility await at this sprawling country retreat. A stream meanders through the 15.37 acre property forming two waterfalls and flows into a deep water pond creating a beautiful lush landscape viewed from many vantage points. This amazing and expansive 7,460 square foot home is comprised of three 18th century structures that were dismantled and brought together. At the center of the

  PAULA REDMOND Corcoran Country Living

  259 Woodstock Rd, Millbrook, NY 12545
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  /36

  $6,785,000

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

  47 Crescent Rd, Millbrook, NY 12545

  Exquisitely restored 1822 farmhouse on 50+ acres in Millbrook, NY, blending historic charm and modern luxury. This stunning home features sun-filled rooms, original hardwood floors, and six fireplaces. The gourmet kitchen is equipped with marble countertops, high-end appliances, a butler's pantry, and a fireplace. A beautiful sunroom with floor-to-ceiling windows and marble floors connects

  William Melnick Elyse Harney Real Estate

  47 Crescent Rd, Millbrook, NY 12545
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  /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
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  /33

  $349,999

  • 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

  joe Cb eXp Realty

  40 Glen Ave, Dover Plains, NY 12522
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  /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
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  /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
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  /23

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,264 Sq Ft

  174 Horseshoe Rd, Millbrook, NY 12545

  Welcome to 174 Horseshoe Rd, Millbrook, NY | A great value opportunity.Located just minutes from the heart of Millbrook, this 2,264 sq ft raised ranch on 1.21 acres presents an exciting opportunity for buyers seeking space, functionality, and an opportunity for sweat equity. With a functional layout, hardwood floors, a partially finished basement and a two-car garage, this home is

  Curtis Darragh Legacy Land & Homes LLC

  174 Horseshoe Rd, Millbrook, NY 12545
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  /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
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  /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
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  /37

  $725,000

  • 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
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  /3

  $89,000

  • Land
  • 1.49 Acres
  • $59,732 per Acre

  0 Tinker Town Rd, Dover Plains, NY 12522

  Escape the NYC and envision your perfect getaway on this beautiful 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

  Adnane Chahi Keller Williams Realty Partner

  0 Tinker Town Rd, Dover Plains, NY 12522
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  /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
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  /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
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  /29

  $495,000

  • 3 Beds
  • 1 Bath
  • 1,656 Sq Ft

  23 Johnson Ln, Millbrook, NY 12545

  Welcome to 23 Johnson Lane in the Highly Desirable Millbrook, NY. This Private and Serene Property is calling out to you. With its old charming country feel and tranquil surroundings, this 1.8 acre property is waiting for you. This Lovely 3 Bedroom Ranch, which lives like a 4 bedroom, has a large bonus room and a bright & airy flow & layout that is ready for you and your family to come and make

  KATHERINE ROBLES DE PEREZ BHHS Hudson Valley Properties

  23 Johnson Ln, Millbrook, NY 12545
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  /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
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  /46

  $1,800,000

  • 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
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  /8

  $375,000

  • Land
  • 10 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
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  /9

  $1,150,000

  • Land
  • 28 Acres
  • $40,450 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
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  /9

  $1,075,000

  • Land
  • 23 Acres
  • $45,764 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
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  /5

  $325,000

  • Land
  • 0.28 Acre
  • $1,160,714 per Acre

  0 Reservoir Dr Unit KEY868959, Millbrook, NY 12545

  Commercial building lot in Village of Millbrook, located on lovely street directly across from the Town Hall. This is a one of a kind offering in the GB zone in the Village. Permitted uses include single family dwelling, two-family dwelling, bed & breakfast, office, retail, along with many uses with a special permit. Village water and sewer. Great investment opportunity!

  George Whalen III George T Whalen Real Estate

  0 Reservoir Dr Unit KEY868959, Millbrook, NY 12545
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  /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
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  /46

  $795,000

  • 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
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  /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
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  /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 surroundings.At the heart

  Noble Black Douglas Elliman Real Estate

  365-381 Tower Hill Rd, Wassaic, NY 12592
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  /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
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  /19

  $165,000

  • Land
  • 5 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
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  /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
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  /25

  $12,950,000

  • 4 Beds
  • 4.5 Baths
  • 6,191 Sq Ft

  123 Butts Hollow Rd, Dover Plains, NY 12522

  Welcome to a once-in-a-lifetime opportunity to own an exceptional equestrian estate sprawling over approximately 185 unrestricted acres in the heart of Millbrook hunt country. Originally built in 1865, this property has been meticulously expanded with a lavish addition spanning over 6000 sq ft, seamlessly blending antique charm with modern opulence. Enjoy miles of fenced pastures, riding trails,

  OLIVER BROWN Houlihan Lawrence Inc.

  123 Butts Hollow Rd, Dover Plains, NY 12522
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  /39

  $1,050,000

  • 5 Beds
  • 3.5 Baths
  • 3,664 Sq Ft

  3715 Route 44 Unit 37, Millbrook, NY 12545

  This historic 1800s home of James Mabbett sits on 4 plus acres with a pristine pond and extensive outbuildings. The main house with its fine architectural details has been newly renovated and updated with new baths and kitchen, appliances, fixtures, mechanicals, gleaming hardwood floors, moldings and coffered ceilings. Enter the high ceiling elegant foyer which leads to a living room with a

  ANN WILKINSON Compass Greater NY, LLC

  3715 Route 44 Unit 37, Millbrook, NY 12545
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  /21

  $7,900,000

  • Land
  • 442 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
• 

  

  /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
• 

  

  /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

  $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, and

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522
• 

  

  /11

  $205,000

  • Land
  • 2.50 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, and

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522
• 

  

  /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, and

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522

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