David E. Cornwell
Licensed Real Estate Salesperson
REALTOR®
Walton, NY
Office: (607) 865-7000 (607) 437-8941

309 Woodstock Road, Millbrook, NY 12545

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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 homes 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 pondsâ??creating 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 chefs 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 childrens 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 â?? an entertainers 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 entertainers 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 Gewürztraminer. Current production is 600+ cases

309 Woodstock Road | MLS# 20252447

This single family home located at 309 Woodstock Road, Millbrook, NY 12545 is currently listed for sale with an asking price of $19,995,000. This property was built in 1987 and has 7 bedrooms and 7 full and 2 partial baths with 12659 sq. ft. Woodstock Road is located within the Millbrook Central School District school district. Search Millbrook real estate on david-cornwell.timberlandproperties.com today.

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Property Features

Property Type: Residential - Single Family
Basement: Yes
Cooling: Central Air
Garage: 3 car attached
Home Style: Greek Revival
Lot Size: 63.46 Acres
Taxes: $138,201
Year Built: 1987

Feature Descriptions

Days on Site: 254
Lot: Agricultural, Meadow, Private
Parcel #: 135889-6666-00-568218-0000
Parking: Additional Parking
SQFT Total: 12659
Water: Well

Local Schools

School District: Millbrook Central School District

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Estimated Payment

$ 61,848.83 per month $44,500.20 Principal & Interest $11,516.75 Property Tax $5,831.88 Homeowner's Insurance

Change Payment Information

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years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Corcoran Country Living

Shown By

Agent Name: David E. Cornwell
Agent Phone: (607) 437-8941
Agency Title: Timberland Properties

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All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 03/05/2026. The listing information on this page last changed on 03/05/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 03/05/2026 2:59:39 AM EST) or Global MLS (last updated Thu 03/05/2026 1:21:58 AM EST) or New York State Alliance MLS (last updated Thu 03/05/2026 2:34:30 AM EST) or Hudson Valley Catskill Region MLS (last updated Thu 03/05/2026 12:11:15 AM EST) or OneKey MLS (last updated Thu 03/05/2026 1:45:06 AM EST). Real estate listings held by brokerage firms other than Timberland Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless.

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