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309 Woodstock Road

Millbrook, NY 12545
  • $19,995,000
  • STATUS: Active
  • MLS #: 20252447
UPDATED: 167 min ago
$19,995,000
  • 7
    BEDS
  • 63.46
    ACRES
  • 7
    BATHS
  • 2
    1/2 BATHS
  • 12,659
    SQFT
  • $1,580
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1987
County:
Area:

School Ratings & Info

Description

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, designed by renowned architect Jimmy Crisp, create a magnificent home around the original core and seamlessly introduce contemporary luxury without compromising the home's historic integrity. Canoe Hill is approached through a gated entry and winding half-mile private drive through established vineyard rows and majestic trees. The rolling landscape presents a tapestry of meticulously maintained formal gardens, productive vegetable plots, heritage fruit trees, and pristine spring-fed pondscreating an environment of pastoral perfection and offering unparalleled privacy and natural splendor. Entered through a gracious foyer with a dramatic curved staircase and double-height ceiling, the center corridor leads you through the heart of the historic part of home into an expansive family wing featuring an immense chef's kitchen with dining area and stone fireplace. The adjacent family room is highlighted by vaulted ceilings, original beams and a stone fireplace. Upstairs are five thoughtfully appointed bedrooms, including a palatial primary suite featuring a fireplace and dressing room, plus two en-suite bedrooms, one with fireplace. Two additional bedrooms on the third floor share a full bath. The finished basement reveals a professional wine cellar with tasting rooms, a children's playroom, laundry and abundant storage. The West Wing presents entertaining at its finest, featuring a 12-seat dining room, a sun-drenched morning room, and a spectacular formal living room with 22-foot ceilings, a stone fireplace and private veranda with an additional outdoor fireplace. The East Wing is the latest expansion and includes a library also serving as a second dining room and an office suite. The crown jewel of this wing is the remarkable Tartan House, accessed through a doorway concealed by a Tartan painting an entertainer's paradise featuring a grand Tartan gathering room with full bar, billiards and stone fireplace, complemented by two distinct Tartan bedroom suites above, and below, a glamourous, tiered 12-seat movie theater that indulges the senses and is an entertainer's showpiece. The outdoor amenities rival the finest resort destination and feature a fully landscaped pool area enhanced by two covered pergolas - one housing a complete outdoor kitchen with pizza oven, while the adjacent boasts a full bar for seamless entertaining. Other exterior features include a sculptured rose garden entertaining area, walking trails, a golf hole and gorgeous six spring-fed ponds that keep the grounds lush and vineyard irrigated. The standalone guest house presents a private retreat with generous living spaces with terrace, a full kitchen, a bedroom suite and additional full bathroom and pantry. A professionally equipped gymnasium and three-car garage complete this impressive structure. At the heart of this exceptional compound lies Elysabeth Vineyards, a fully operational boutique winery and bottling facility offering, high-quality wines produced from estate grapes. Varietals include Cabernet Sauvignon, Pinot Noir, Cab Franc, Merlot, Chardonnay, Reisling and Gewrztraminer. Current production is 600+ cases annually. The winery includes a turnkey 2,700 SF residence complete with a private tasting room, terrace and catering kitchen offering both commercial potential and intimate entertaining possibilities for the discerning oenophile. Canoe Hill represents a unique opportunity to own a piece of Hudson Valley history while enjoying the finest contemporary amenities and endless possibilities. This is a Co-Listing with The Corcoran Group.

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© 2025 by Hudson Valley Catskill Region MLS. All Rights Reserved. The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS. Real estate listings held by brokerage firms other than This Old Hudson Team at Houlihan Lawrence are marked with IDX logo and the detailed information about them includes the name of the listing broker. All information provided is deemed reliable but is not guaranteed and should be independently verified. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data Last Updated:2025-11-09T23:53:14.62
www.thisoldhudsonrealestate.com/homes/165199530
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309 Woodstock Road Millbrook, NY 12545

  • Price: $19,995,000
  • Status: Active
  • On Site: Days
  • Updated: 167 min ago
  • MLS #: 20252447
7
Beds
7
Baths
2
½ Baths
63.46
Acres
12,659
SQFT
$1,580
$/SQFT
1987
Built
Neighborhood:
Millbrook
County:
Dutchess
Area:
Millbrook
School District:
Millbrook Central School District
Property Description
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, designed by renowned architect Jimmy Crisp, create a magnificent home around the original core and seamlessly introduce contemporary luxury without compromising the home's historic integrity. Canoe Hill is approached through a gated entry and winding half-mile private drive through established vineyard rows and majestic trees. The rolling landscape presents a tapestry of meticulously maintained formal gardens, productive vegetable plots, heritage fruit trees, and pristine spring-fed pondscreating an environment of pastoral perfection and offering unparalleled privacy and natural splendor. Entered through a gracious foyer with a dramatic curved staircase and double-height ceiling, the center corridor leads you through the heart of the historic part of home into an expansive family wing featuring an immense chef's kitchen with dining area and stone fireplace. The adjacent family room is highlighted by vaulted ceilings, original beams and a stone fireplace. Upstairs are five thoughtfully appointed bedrooms, including a palatial primary suite featuring a fireplace and dressing room, plus two en-suite bedrooms, one with fireplace. Two additional bedrooms on the third floor share a full bath. The finished basement reveals a professional wine cellar with tasting rooms, a children's playroom, laundry and abundant storage. The West Wing presents entertaining at its finest, featuring a 12-seat dining room, a sun-drenched morning room, and a spectacular formal living room with 22-foot ceilings, a stone fireplace and private veranda with an additional outdoor fireplace. The East Wing is the latest expansion and includes a library also serving as a second dining room and an office suite. The crown jewel of this wing is the remarkable Tartan House, accessed through a doorway concealed by a Tartan painting an entertainer's paradise featuring a grand Tartan gathering room with full bar, billiards and stone fireplace, complemented by two distinct Tartan bedroom suites above, and below, a glamourous, tiered 12-seat movie theater that indulges the senses and is an entertainer's showpiece. The outdoor amenities rival the finest resort destination and feature a fully landscaped pool area enhanced by two covered pergolas - one housing a complete outdoor kitchen with pizza oven, while the adjacent boasts a full bar for seamless entertaining. Other exterior features include a sculptured rose garden entertaining area, walking trails, a golf hole and gorgeous six spring-fed ponds that keep the grounds lush and vineyard irrigated. The standalone guest house presents a private retreat with generous living spaces with terrace, a full kitchen, a bedroom suite and additional full bathroom and pantry. A professionally equipped gymnasium and three-car garage complete this impressive structure. At the heart of this exceptional compound lies Elysabeth Vineyards, a fully operational boutique winery and bottling facility offering, high-quality wines produced from estate grapes. Varietals include Cabernet Sauvignon, Pinot Noir, Cab Franc, Merlot, Chardonnay, Reisling and Gewrztraminer. Current production is 600+ cases annually. The winery includes a turnkey 2,700 SF residence complete with a private tasting room, terrace and catering kitchen offering both commercial potential and intimate entertaining possibilities for the discerning oenophile. Canoe Hill represents a unique opportunity to own a piece of Hudson Valley history while enjoying the finest contemporary amenities and endless possibilities. This is a Co-Listing with The Corcoran Group.
Exterior Features

Architectural Style Greek Revival Attached Garage YN Yes Exterior Features [] Fencing [] Foundation Details [] Garage YN Yes Lot Features AgriculturalMeadowPrivate Parking Features Additional Parking Patio And Porch Features [] Pool Features [] Road Frontage Type [] Road Surface Type [] Roof [] View Vineyard Waterfront Features [] Window Features []

Interior Features

Appliances [] Basement Finished Construction Materials [] Cooling Central Air Cooling YN Yes Door Features [] Electric [] Fireplace Features [] Flooring [] Heating [] Interior Features [] Laundry Features [] Levels [] Rooms Total 0

Property Features

Association Amenities [] Association Fee Includes [] Community Features [] General Tax 36695 Listing Terms [] New Construction YN No Other Equipment [] Other Structures Guest HouseOutdoor KitchenPergolaPool House Property Condition [] Property Sub Type Single Family Residence School Tax 101506 Security Features [] Sewer [] Special Listing Conditions [] Structure Type [] Tax Annual Amount 138201 Tax Assessed Value 6375495 Tax Block 6-666 Tax Legal Description 35.25 AC (S) 1903 0500 1800 0751 28.21 AC (S) 1911 0020 1707 0597 Tax Lot 568487 Township Washington Utilities [] Water Source Well

[Hudson Valley Catskill Region MLS] logo© 2025 by Hudson Valley Catskill Region MLS.
Listing # 20252447 provided courtesy of Jason Karadus of Corcoran Country Living: .
© 2025 by Hudson Valley Catskill Region MLS. All Rights Reserved. The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS. Real estate listings held by brokerage firms other than This Old Hudson Team at Houlihan Lawrence are marked with IDX logo and the detailed information about them includes the name of the listing broker. All information provided is deemed reliable but is not guaranteed and should be independently verified. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data Last Updated:2025-11-09T23:53:14.62
 
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