Homes for Sale near Dutchess Day School

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  /44

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,836 Sq Ft

  3465 Route 22, Dover Plains, NY 12522

  Experience serene country living at 3465 Route 22, Dover Plains, NY 12522! This spacious, well-maintained ranch-style home offers the perfect blend of comfort and style, set back from the road for privacy and boasting breathtaking panoramic views of the surrounding Hudson Valley landscape. Step inside to discover a bright and inviting living room, complete with a cozy fireplace—perfect for

  

  Omar Harper

  Epique Realty

  (845) 599-0147

  3465 Route 22, Dover Plains, NY 12522
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  /36

  $3,500,000

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

  97 Wing Rd Unit 101, Millbrook, 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

  97 Wing Rd Unit 101, Millbrook, NY 12545
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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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  /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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  /32

  $1,900,000

  • 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

  $2,225,000

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

  3598 Route 82, Millbrook, NY 12545

  Have you ever thought about what it would be like to live in a painting? This architecturally distinctive home built with love and craftsmanship in 1994 will appeal to all of your senses. It sits on 5.43 acres at the end of a long tree-lined driveway surrounded by working farmland providing picturesque views in all directions in all seasons. The home spans three floors of 4,548 finished square

  PAULA REDMOND Corcoran Country Living

  3598 Route 82, Millbrook, NY 12545
• 

  

  /17

  $4,995,000

  • 2 Beds
  • 2.5 Baths
  • 1,713 Sq Ft

  92 Sutton Rd Unit 114, Millbrook, NY 12545

  Discover the potential of owning 150 acres of breathtaking land with stunning views of the Catskills. This unique property features two existing structures: a charming 2-bedroom, 2-bath house perfect for cozy living or weekend getaways, and an expansive 10,000 square foot hangar building, ideal for storage, workshops, or creative projects.Imagine hosting gatherings in the enchanting

  Helen Murray William Pitt Sothebys Int Rlty

  92 Sutton Rd Unit 114, Millbrook, NY 12545
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  /47

  $2,995,000

  • 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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  /36

  $1,500,000

  • 3 Beds
  • 6 Baths
  • 2,700 Sq Ft

  4258 Route 44, Millbrook, NY 12545

  Unique residential and commercial opportunity in the heart of Dutchess County. This historic property was originally built in the 19th century as a Congregational church and has served as a livestock auction house and summer opera venue before evolving into its current beloved Charlotte's restaurant in 2006.The property offers a rare live/work opportunity. A lovely 3-bedroom apartment is

  Stephen Pener William Pitt Sothebys Int Rlty

  4258 Route 44, Millbrook, NY 12545
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  /36

  $6,750,000

  • 6 Beds
  • 9 Baths
  • 8,177 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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  /36

  $1,495,000

  • 6 Beds
  • 4.5 Baths
  • 4,110 Sq Ft

  57 Cedar Berry Ln, Dover Plains, NY 12522

  Just 90 miles north of NYC, this stunning Hudson Valley property offers the ultimate live, work, play lifestyle. Nestled on 4.08 private acres, this custom-built log home captures the vibrant essence of the area, known for its booming art and music scene, farm-to-table eateries, outdoor adventures, and local wineries. Generating over $80,000 in VRBO rental income in 2022, this turnkey estate is

  Lindsay Stevens eXp Realty

  57 Cedar Berry Ln, Dover Plains, NY 12522
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  /18

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 3,016 Sq Ft

  10 May Knoll, Dover Plains, NY 12522

  The Adirondack is YOUR Perfect Waterfront Getaway. Tranquility, endless possibilities and the warm vibes of the Hudson Valley welcome you. Situated on 1.951 acres along the majestic Ten Mile River. The home features an Old World charm with custom woodwork, built-in-cabinets, hardwood floors, a unique stone fireplace and your very own private balcony overlooking the spacious backyard. Imagine cool

  Dani Dorman Real Broker NY LLC

  10 May Knoll, Dover Plains, NY 12522
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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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  /35

  $375,000

  • 3 Beds
  • 1 Bath
  • 1,786 Sq Ft

  53 Glen Ave, Dover Plains, NY 12522

  Charming, cozy and clean, you can move right in and live low-maintenance in this perfect home.The entire back end of the property abuts Butts Hollows Brook which runs year round and flows into Ten Mile River. Enjoy summers in the above ground pool with a beautiful brand new liner. Conveniently located 2 miles from Dover Plains train station. Shopping, schools and recreation are all nearby. This

  Diana Lenz BHHS Hudson Valley Properties

  53 Glen Ave, 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
• 

  

  /19

  $795,000

  • 3 Beds
  • 3.5 Baths
  • 1,956 Sq Ft

  452 Camby Rd, Verbank, NY 12585

  This beautifully maintained, move-in-ready residence offers single-level living just 10 minutes from the Village of Millbrook. Featuring a spacious, open floor plan with soaring ceilings, a cozy gas fireplace, hardwood flooring, and a finished lower level, this home is designed for comfort. The updated kitchen is well-appointed with a generous dining area, pellet stove and sliding glass doors

  PAULA REDMOND Corcoran Country Living

  452 Camby Rd, Verbank, NY 12585
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  /25

  $749,000

  • 3 Beds
  • 1.5 Baths
  • 1,700 Sq Ft

  32 Reservoir Dr, Millbrook, NY 12545

  Nestled in the picturesque village of Millbrook, this beautifully renovated 3-bed home offers the perfect blend of original charm and modern comfort. Situated just a short walk from village amenities, this home has been thoughtfully updated with high-quality finishes and attention to detail. New Roof, Siding, New Forced Air Furnace & Central Air, as well as Updated Electrical & Plumbing with

  Kali Markowski K. Fortuna Realty, Inc.

  32 Reservoir Dr, Millbrook, NY 12545
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  /42

  $485,000

  • 2 Beds
  • 1 Bath
  • 1,240 Sq Ft

  252 Ernest Rd, Millbrook, NY 12545

  Situated on a bucolic road is this charming two bedroom, one bath cottage perfect for enjoying life in the country. This home has an inviting and comfortable interior complete with hardwood floors. Surrounded by larger estates, one can enjoy picturesque views of farmland to the east and north, and to the west spectacular winter sunsets over the Catskills. Off the front of the home, a delightful

  Susan Whalen George T Whalen Real Estate

  252 Ernest Rd, Millbrook, NY 12545
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  /32

  $299,900

  • 2 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  126 Christian Hill Rd Unit 128, Dover Plains, NY 12522

  Charming Property with Potential Overview This lovely property is nestled within a robust estate area, offering the perfect blend of tranquility and opportunity. Set on 2 acres of land, the surroundings feature mature trees, a sweeping lawn, and the privacy that creates a serene oasis. Natural Light: The home benefits from ample natural light, enhancing the open feel of the kitchen and living

  Toni Soule Bain Real Estate

  126 Christian Hill Rd Unit 128, Dover Plains, NY 12522
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  /29

  $508,000

  • 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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  /8

  $375,000

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

  TBD Stanford Rd, Millbrook, NY 12545

  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 location. Additional

  OLIVER BROWN Houlihan Lawrence Inc.

  TBD Stanford Rd, Millbrook, NY 12545
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  /9

  $1,150,000

  • Land
  • 28 Acres
  • $40,450 per Acre

  TBD Parcel 5 Woodstock Rd, Millbrook, NY 12545

  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 Parcel 5 Woodstock Rd, Millbrook, NY 12545
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  /9

  $1,075,000

  • Land
  • 23 Acres
  • $45,764 per Acre

  TBD Parcel 1 Woodstock Rd, Millbrook, NY 12545

  Located just outside the Village of Millbrook on a scenic gravel country road, this 23.49-acre parcel offers a picturesque setting for your dream retreat. The land features a mix of old wood 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 escape and explore the

  OLIVER BROWN Houlihan Lawrence Inc.

  TBD Parcel 1 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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  /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 overlooking

  Norm Mackay

  17 Washington Ave, Millbrook, NY 12545
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  /26

  $399,900

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft

  179 Horseshoe Rd, Millbrook, NY 12545

  ** PRICE REDUCED ** THIS RAISED RANCH STYLE HOME IS NESTLED ON A LEVEL 1.5 ACRE PROPERTY IN THE 'MILLBROOK HEIGHTS' NEIGHBORHOOD. ENTRY INTO THE FOYER, AND UP ONTO LEVEL ONE: A BRIGHT & AIRY LIVING ROOM WITH OAK HARDWOOD FLOORING. THE DINNING AREA HAS AMPLE ROOM, GOOD WALL SPACE, AND A SLIDING GLASS DOOR ACCESS TO THE REAR DECK. THE EAT-IN-KITCHEN HAS GOOD CABINET STORAGE, CAN SEAT FOUR

  Greg Kane Kane & Associates

  179 Horseshoe Rd, 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
• 

  

  /20

  $415,000

  • 3 Beds
  • 1.5 Baths
  • 1,300 Sq Ft

  3889 Route 82, Millbrook, NY 12545

  Welcome to this beautiful brick ranch, ideally situated on a level one-acre lot just outside the charming Village of Millbrook.This well-maintained 3-bedroom, 2-bath home offers easy, one-level living with hardwood floors throughout, a cozy living room with a wood-burning fireplace, and an enclosed porch perfect for relaxing or entertaining. The spacious eat-in kitchen flows nicely and

  Ginalea Healy K. Fortuna Realty, Inc.

  3889 Route 82, Millbrook, NY 12545
• 

  

  /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 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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  /39

  $895,000

  • 4 Beds
  • 2.5 Baths
  • 3,398 Sq Ft

  147 Verbank Village Rd, Verbank, NY 12585

  This circa 1910, handsome Hudson Valley farmhouse on 19+ acres is a wonderful country retreat, perfect for entertaining family and friends. It boasts beautiful wood flooring, attractive high ceilings, and ample windows that provide an abundance of natural light and take full advantage of picturesque views of the outdoors. A fireplace adds winter warmth and the central air adds summer comfort.

  Susan Whalen George T Whalen Real Estate

  147 Verbank Village Rd, Verbank, NY 12585
• 

  

  /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
• 

  

  /14

  $135,000

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  160 Holpsapple Rd Unit 52, Dover Plains, NY 12522

  Welcome to this charming 3-bedroom, 2-bathroom mobile home in Dover! Enjoy the open floor plan with a spacious living area, perfect for gatherings. The well-appointed kitchen offers ample storage, and the primary suite comes with a private bath for added comfort. With two additional bedrooms, this home is perfect for all! Located in a great community, close to local amenities and schools. Don't

  MICHAEL SANTARPIA K. Fortuna Realty, Inc.

  160 Holpsapple Rd Unit 52, Dover Plains, NY 12522
• 

  

  /36

  $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
• 

  

  /43

  $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
• 

  

  /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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