Dutchess, NY Homes

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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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  Explore Washington

• 

  

  

  /31

  $2,950 per month

  • 2 Beds
  • 1 Bath
  • 2,048 Sq Ft
  • House for Rent

  72 Christian Hill Rd, Dover Plains, NY 12522

  Peaceful Living on Over 5 Acres – Versatile 2–3 Bedroom Home Enjoy privacy, space, and comfort in this charming 2–3 bedroom, 2-bath home nestled on over 5 serene acres at the end of a quiet cul-de-sac. Featuring over 2,000 finished square feet across the main and upper levels, this home offers a flexible layout full of potential. The main floor includes beautiful hardwood floors throughout, with

  Blake Michaud Serhant LLC

  72 Christian Hill Rd, Dover Plains, NY 12522
• 

  $745,000 Sold Jul 23, 2025

  • 2,686 Sq Ft
  • $277/SF
  • 98 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1968

  16 Shunpike, Clinton Corners, NY 12514

  You will fall in love with this spacious, open layout in this cape style home that is overflowing with natural light and brand new hardwood floors throughout. This home has an outstanding flow and surreal views (that include your pond) and just call for you to relax and unwind. The main level offers an open floor plan with a beautiful kitchen, dining, and living space with sliding glass doors

  Monica Whitney Exit Realty Connections

  16 Shunpike, Clinton Corners, NY 12514
• 

  Est $507,658 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,946 Sq Ft

  1402 Route 343, Washington, NY 12522

  1402 Route 343, Washington, NY 12522
• 

  

  

  /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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  /18

  $1,550 per month

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

  2582 Route 44 Unit 1, Salt Point, NY 12578

  Located in the highly sought-after town of Millbrook, this fully furnished 1-bedroom apartment offers a clean, comfortable living space with both heating and air conditioning for year-round comfort. Thoughtfully outfitted with everything you need to settle in right away, the unit combines convenience and ease in a peaceful setting. Just a short drive from the village, local shops, and scenic

  Kason Fearon Serhant LLC

  2582 Route 44 Unit 1, Salt Point, NY 12578
• 

  $700,000 Sold Jul 18, 2025

  • 1,500 Sq Ft
  • $467/SF
  • 18 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1930

  620 Route 343, Millbrook, NY 12545

  Introducing the Millbrook Farmhouse. This beautifully updated cedar shake farmhouse blends idyllic charm with modern upgrades on a landscaped one-acre parcel just minutes from the Village of Millbrook. Fully gut-renovated in 2015, every detail of the property was thoughtfully rebuilt, from the house and garage to the expansive landscaping. Extensive yard work—including tree removal and clearing

  Kyle Irwin Corcoran Country Living

  620 Route 343, Millbrook, NY 12545
• 

  Est $642,284 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,060 Sq Ft

  1046 New York 343, Dover Plains, NY 12522

  1046 New York 343, Dover Plains, NY 12522
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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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  /10

  $1,500 per month

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

  12 Alden Place Unit 3, Millbrook, NY 12545

  Cozy one bedroom apartment in the charming Village of Millbrook. The apartment is move-in ready! This second floor unit in a multi family home offers a shared entrance in the back. Off-street parking. Convenient village location to walk to the grocery store, shops, parks, public tennis courts, and the library. Enjoy village living!

  Susan Whalen George T Whalen Real Estate

  12 Alden Place Unit 3, Millbrook, NY 12545
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  $1,340,000 Sold Jun 30, 2025

  • 2,630 Sq Ft
  • $510/SF
  • 16 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1920

  11 Haight Ave, Millbrook, NY 12545

  Nestled in the heart of Millbrook’s charming village, this fully remodeled center-hall Colonial offers the perfect blend of timeless elegance and modern comfort. Set on 1.27 acres of beautifully landscaped grounds, the home has been thoughtfully reconfigured into a spacious three-bedroom layout to suit today’s lifestyle. A brand-new chef’s kitchen anchors the home, outfitted with top-of-the-line

  Ashley Whittaker Spence Compass Greater NY, LLC

  11 Haight Ave, Millbrook, NY 12545
• 

  Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,584 Sq Ft

  29 Merrit Ave, Millbrook, NY 12545

  29 Merrit Ave, 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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  /21

  $9,500 per month

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

  72 N Mabbettsville Rd, Millbrook, NY 12545

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

  Candy Anderson Compass Greater NY, LLC

  72 N Mabbettsville Rd, Millbrook, NY 12545
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  $1,375,000 Sold Jun 18, 2025

  • 3,318 Sq Ft
  • $414/SF
  • 99 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1987

  817 Stanford Rd, Clinton Corners, NY 12514

  Millbrook Country House. Located just outside the village on a beautiful rural road is this renovated 3,318 square foot home accessed through beautiful stone pillared gates. There is a solar heated, 18’ x 40’ inground saltwater pool with three steps that span the width of the pool, a perfect place for lounging in the water. Offering four bedrooms and three full and two half baths with oak floors

  PAULA REDMOND Corcoran Country Living

  817 Stanford Rd, Clinton Corners, NY 12514
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  Est $596,563 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 3,180 Sq Ft

  109 N Mabbettsville Rd, Millbrook, NY 12545

  109 N Mabbettsville 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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  /43

  $8,750 per month

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • House for Rent

  699 Tower Hill Rd, Millbrook, NY 12545

  Available August 1, 2025 - June 1, 2026. Hidden on five private acres, is a fully furnished home that has been transformed to a contemporary. The view from the expansive living room windows is of a serene landscape, complete with a stone wall, babbling brook and pond. On the main level the living room boasts a wood burning fireplace and soaring ceilings. The home has a chef's kitchen with

  Susan Whalen George T Whalen Real Estate

  699 Tower Hill Rd, Millbrook, NY 12545
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  $1,100,000 Sold Jun 17, 2025

  • 3,188 Sq Ft
  • $345/SF
  • 109 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1970

  5282 Route 82, Salt Point, NY 12578

  Looking for 1 level living in a private secluded wooded area? Situated on 35 acres,this massive 3,188 square foot 3 bedroom custom built California Ranch is just what you are looking for.The floor to ceiling windows allow tons of natural light to permeate throughout the entire open floor plan.Hardwood flooring glistens throughout living area.Stay toasty warm in your family room on those chilly

  Ernie Acampora River Realty Services, Inc.

  5282 Route 82, Salt Point, NY 12578
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  Not Listed For Sale

  0 Milewood Rd Unit KEYH6305719, Washington, NY 12545

  0 Milewood Rd Unit KEYH6305719, Washington, NY 12545
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  /50

  $2,225,000

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

  3598 Route 82, Millbrook, NY 12545

  This architecturally distinctive Millbrook home was authentically built in the Second Empire / Victorian period style in 1994. Constructed with modern living in mind and extraordinary craftsmanship, this Millbrook residence is absolutely turn-key and offers incomparable privacy. Sited on 5.43 pristine acres at the end of a long, private tree-lined driveway, the property is surrounded by working

  PAULA REDMOND Corcoran Country Living

  3598 Route 82, Millbrook, NY 12545
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  /17

  $1,850 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  152 Church St, Millbrook, NY 12545

  Yearly Rental. Enjoy living in the heart of the Village of Millbrook with easy access to restaurants, shops and more. This second floor one bedroom, one bath apartment is located above a restaurant. It was recently refreshed with new paint, refinished floors and a new stove. The living room/dining room is light filled and spacious with 8'7" high ceilings. The galley kitchen has a pass through to

  PAULA REDMOND Corcoran Country Living

  152 Church St, Millbrook, NY 12545
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  $530,000 Sold Jun 11, 2025

  • 1,950 Sq Ft
  • $272/SF
  • 192 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1900

  8 Alden Place, Millbrook, NY 12545

  This classic, 1,950 Sq ft, 3 bedroom, 1.5 bath charming Victorian home built circa 1900, sits in the heart of desirable Millbrook Village, convenient to all the restaurants, shops and galleries, yet set on a quiet and private street. With its beautifully landscaped gardens, fabulous large back yard, and plenty of space for recreation and for pets to play, this lovely home is the perfect place to

  Neil Charles Neil Charles Real Estate, LLC

  8 Alden Place, Millbrook, NY 12545
• 

  Est $424,593 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  998 Route 343, Dover Plains, NY 12522

  998 Route 343, Dover Plains, NY 12522
• 

  

  /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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  /16

  $3,500 per month

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  422 Stanford Rd, Millbrook, NY 12545

  Renovated three bedroom ranch in country setting, 5 minutes from the Village of Millbrook. Living room with brick fireplace, eat in kitchen, family room, two full bathrooms, laundry room, mud room, beautiful hardwood floors. Enjoy the sunsets on the deck, the tranquil setting and the scenic country road in Millbrook! Tenant responsible for lawn care, snow removal, garbage and all utilities. A

  George Whalen III George T Whalen Real Estate

  422 Stanford Rd, Millbrook, NY 12545
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  $340,000 Sold Jun 09, 2025

  • 1,300 Sq Ft
  • $262/SF
  • 73 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1965

  54 Bennett Common, Millbrook, NY 12545

  Welcome to this charming 2-bedroom, 2-full bath, second-floor unit located in the Bennett Common Community. This home offers both comfort and convenience with a newer chairlift installed for easy 2nd floor access. As you step inside, you'll be captivated by the stunning hardwood floors, the abundance of natural light and spacious layout. The living room features a beautiful fireplace and sliding

  Michael Dunstan RE/MAX Town & Country

  54 Bennett Common, Millbrook, NY 12545
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  Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 5,958 Sq Ft

  221 Shunpike Unit 231, Clinton Corners, NY 12514

  221 Shunpike Unit 231, Clinton Corners, NY 12514
• 

  

  /47

  $2,900,000

  • 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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  /28

  $3,100 per month

  • 2 Beds
  • 1 Bath
  • 1,480 Sq Ft
  • House for Rent

  358 Verbank Rd, Millbrook, NY 12545

  Charming home located on a scenic country road in Millbrook. The house features a lovely new eat-in kitchen. The interior has been freshly painted and the beautiful hardwood floors have been refinished. The spacious living room room has a wood stove. A stylish, new full bathroom and den/home office complete the first floor. Upstairs, there are two bedrooms and attic space for storage. The front

  Susan Whalen George T Whalen Real Estate

  358 Verbank Rd, Millbrook, NY 12545
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  $115,000 Sold May 23, 2025

  • 1,728 Sq Ft
  • $67/SF
  • 173 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1972

  4 Neighborly Ln, Dover Plains, NY 12522

  Nestled between the charming villages of Millbrook and Dover is the perfect investment opportunity. Easy commuter access via Rt 22, Taconic Parkway and minutes from the Metro-North Harlem line station. Legal rental property on-sight to help offset the cost of living. Come turn this home into the home of your dreams! Additional Information: HeatingFuel:Oil Below Ground,

  Jessica Chutka-Pelletier

  4 Neighborly Ln, Dover Plains, NY 12522
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  /2

  Est $841,219 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,465 Sq Ft

  288 Shunpike, Clinton Corners, NY 12514

  288 Shunpike, Clinton Corners, NY 12514
• 

  

  /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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  /9

  $2,200 per month

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

  92 Maple Ave, Millbrook, NY 12545

  Newly constructed one bedroom apartment situated in a beautiful and tranquil location in the Village of Millbrook. Open floor plan with light-filled living room and well-appointed kitchen, complete with a dishwasher. A spacious corner bedroom and an inviting bathroom that includes a walk-in shower, soaking tub and heated floors. Central air, a washer/dryer, generous closet space, shared

  Susan Whalen George T Whalen Real Estate

  92 Maple Ave, Millbrook, NY 12545
• 

  $625,000 Sold May 16, 2025

  • 1,749 Sq Ft
  • $357/SF
  • 39 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1997

  20 North Ave, Millbrook, NY 12545

  WELCOME HOME AND ENJOY LIVING AT ITS BEST IN THE BEAUTIFUL VILLAGE OF MILLBROOK! THIS IS A LOVELY CONTEMPORARY COLONIAL WHICH IS CONVENIENTLY LOCATED WALKING DISTANCE INTO TOWN TO TAKE ADVANTAGE OF RESTAURANTS, LIBRARY, FARMERS MARKET, TENNIS COURTS AND MORE. THIS HOME HAS A LARGE FAMILY ROOM W/ FIREPLACE, HW FLOORS & VAULTED CEILINGS. OPEN CONCEPT TO KITCHEN WHICH ALSO HAS LAUNDRY SET UP.

  Christine Ryan

  20 North Ave, Millbrook, NY 12545
• 

  Est $247,637 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  26 Balsam Ct, Dover Plains, NY 12522

  26 Balsam Ct, Dover Plains, NY 12522
• 

  

  /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
• 

  

  /28

  $4,200 per month

  • 4 Beds
  • 3 Baths
  • 4,570 Sq Ft
  • House for Rent

  79 Camby Rd, Verbank, NY 12585

  A wonderful Colonial home with pastoral views in Millbrook. This home includes a spacious interior, featuring many original details. Four bedrooms and three full baths, along with a formal dining room, living room, family room, office, and two kitchens. Situated on a working dairy farm with beautiful farmland views. Convenient to Route 82 and just minutes to the village of Millbrook. The tenant

  Susan Whalen George T Whalen Real Estate

  79 Camby Rd, Verbank, NY 12585
• 

  $454,900 Sold May 16, 2025

  • 2,496 Sq Ft
  • $182/SF
  • 190 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  41 Horseshoe Rd, Millbrook, NY 12545

  Welcome to 41 Horseshoe Road, a delightful residence located in Millbrook, New York. With approximately 2500 square feet of living space, this home offers a perfect blend of comfort and potential, making it an ideal choice for a full-time residence, weekend getaways, or anyone looking to immerse themselves in the beauty of the Hudson Valley. As you step inside, you’ll immediately feel the warmth

  Ellen 'Ellie' Savoy

  41 Horseshoe Rd, Millbrook, NY 12545
• 

  Est $231,618 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,380 Sq Ft

  9 Wayne Dr, Dover Plains, NY 12522

  9 Wayne Dr, Dover Plains, NY 12522

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