309 Woodstock Rd

Millbrook, NY 12545

$19,995,000
Price
7
Beds
12,659 Sq. Ft.
$1,580 / Sq. Ft.
12,659
Sq. Ft.
$1,580
per Sq. Ft.
a view of swimming pool from a backyard
a front view of a house with a yard
a front view of a house with lots of green space
a view of a livingroom with furniture stairs a fireplace and a chandelier
a view of bathroom with a potted plant and a sink
a living room with furniture and windows
a living room with furniture and a large window
a front view of a house with a yard
a kitchen with stainless steel appliances granite countertop a stove and a wooden floors
a view of a closet with storage
a view of a hallway with a living room
a living room with furniture and a large window
a view of a livingroom with furniture
a bedroom with a bed and a walk in closet with wooden floor
a spacious bedroom with a bed and a chandelier
a bathroom with a sink and a mirror
a living room with furniture and a fireplace
a living room with furniture and a flat screen tv
a bathroom with a sink and a mirror
a front view of a house with garden
a living room with furniture a fireplace and a flat screen tv
a bathroom with a bathtub a sink and a shower
a bedroom with a bed a flat screen tv and a fireplace
a white bed sitting in a room next to a window
a view of entryway
a view of a wine cellar
a view of a dining room with furniture and chandelier
a small garden covered with tall trees
a view of a house with sitting area and swimming pool
swimming pool view with a seating space and a garden
a view of a patio with couches table and chairs with garden view
a view of a kitchen with stainless steel appliances granite countertop a stove and a sink
a view of swimming pool with outdoor seating and plants
a view of a backyard with sitting area and garden
a view of a patio with table and chairs potted plants and palm tree
a front view of a house with a yard and trees
a living room with large couches chandelier and a large window
a kitchen with a sink stove and cabinets
a bathroom with a sink and a mirror
a front view of a house with a yard
a living room with furniture and a glass door
a view of a dining room with furniture window and outside view
a kitchen with stainless steel appliances granite countertop a sink a stove and wooden floors
a bedroom with a bed couch and window
a close view of light fixtures and a bathroom
47 309WR_102
a picture of flowers
a view of a city

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...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 ponds—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 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 Gewürztraminer. 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.
  1. Listed by Jason Karadus • Corcoran Country Living
    P: (917)-685-8575 C: (917)-685-8575 jason.karadus@corcorancl.com

Property Details for 309 Woodstock Road

Zoning
RL5
Basement YN
Yes
LISTING UPDATED: 08/21/2025 01:08 PM

Property Details for 309 Woodstock Road

StatusActive
MLS #20252447
Days on Market191
Taxes$138,201 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1987
Lot Size63.46 AC / 2,764,317 SF
CountyDutchess County

Location

Listing Courtesy of Corcoran Country Living
Add your commute

Building Information for 309 Woodstock Road

Stories-Year Built1987Building Size-Lot Size63.46 AC / 2,764,317 SF

Payment Calculator

$110,319 per month

30 year fixed, 6.28% Interest

Principal and Interest

$98,802

Property Taxes

$11,517

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 309 Woodstock Road

Summary
Location and General Information
  • Directions: Route 44 to North on Stanford Rd. Left onto Woodstock Rd to #309.
  • Township: Washington
  • MLS Area Major: Millbrook
  • County: Dutchess
  • Latitude: 41.817969
  • Longitude: -73.725704
  • MLS Area Major: Millbrook
  • Sign On Property YN: No
  • Vineyard: Yes
Taxes and HOA
  • Association Fee: $.00
  • Parcel Number: 135889-6666-00-568218-0000
  • Tax Block: 6-666
  • Tax Legal Description: 35.25 AC (S) 1903 0500 1800 0751 28.21 AC (S) 1911 0020 1707 0597
  • Tax Annual Amount: $138,201.00
Parking
  • Attached Garage YN: Yes
  • Garage YN: Yes
  • Garage Spaces: 3.0
  • Garage YN: Yes
  • Attached Garage YN: Yes
  • Garage Spaces: 3.0
  • Additional Parking: Yes
Property
Lot Information
  • New Construction YN: No
  • Lot Size Acres: 63.46
  • Above Grade Finished Area: 11970.0
  • Below Grade Finished Area: 689.0
  • Living Area: 12659.0
  • Lot Size Area: 63.46
  • Lot Size Units: Acres
  • Lot Size Square Feet: 2764317.6
  • Above Grade Finished Area: 11970.0
  • Below Grade Finished Area: 689.0
  • Lot Size Acres: 63.46
  • Greek Revival: Yes
  • Agricultural: Yes
  • Meadow: Yes
  • Private: Yes
Property and Assessments
  • Owner Name: MN Woodstock Assoc LLC
  • Total Floor Plans Count: 0
  • Property Type: Residential,Single Family Residence
  • Year Built: 1987
  • Property Sub Type: Single Family Residence
  • New Construction YN: No
  • Page: 5776
  • Section: 6-666
Taxes and HOA
  • Tax Assessed Value: 6375495.0
  • Tax Lot: 568,487
Utilities
  • Well: Yes
Interior and Exterior Features
Exterior Features
  • Guest House: Yes
  • Pergola: Yes
  • Pool House: Yes
Interior Features
  • Basement YN: Yes
  • Room Total: 0
  • Bathrooms Total (Integer): 9
  • Bathrooms Total (Decimal): 8.0
  • Bathrooms Total (Notational): 7.2
  • Cooling: Yes
  • Bedrooms Total: 7
  • Bathrooms Full: 7
  • Bathrooms Half: 2
  • Bathrooms Half: 2.0
  • Finished: Yes
  • Central Air: Yes
Mobile Home
Mobile Home Information
  • Sign On Property YN: No
Rental
Rental Information
  • Occupant Type: Owner
  • Occupant Type: Owner

Public Records for 309 Woodstock Road

Taxable ValueLand$514,200Additions$3,858,895Total$4,373,095
Tax Record2024$69,625 ($5,802 / month)
Home Facts
Beds5Baths4.5Total Finished SqFt13,348 SqFtAbove Grade Finished SqFt12,659 SqFtFinished Basement SqFt689 SqFtStories2Lot Size1,535,490 SqFtStyleMiscellaneous ResidentialYear Built1987Year Renovated2011ZoningRL5CountyDUTCHESSAPN135889 6666-00-568218-0000Fireplace TypeHas Fireplace

Schools near 309 Woodstock Road

This home is within Millbrook Central School District.
Rating
School
Type
Grades
Distance
Elm Drive Elementary School
Public - PK to 2
Alden Place Elementary School
Public - 3 to 5
Millbrook Middle School
Public - 6 to 8
Millbrook High School
Public - 9 to 12
Rating
School
Distance
Elm Drive Elementary School
PublicPK to 2

Alden Place Elementary School
Public3 to 5

Millbrook Middle School
Public6 to 8

Millbrook High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 309 Woodstock Road, Millbrook, NY 12545

309 Woodstock Road is a single family home for sale in Millbrook, NY 12545. This property was listed for sale on June 23, 2025 by Corcoran Country Living, it's currently listed at $19,995,000. This listing's school district is Millbrook Central School District. Nearby schools include Elm Drive Elementary School, Alden Place Elementary School and Millbrook Middle School. 309 Woodstock Road is a 7-bed, 9-bath, 12,659 sqft single family home built in 1987.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Corcoran Country Living

The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale or lease on this webpage comes from the the IDX Program of OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. Real estate listings held by brokerage firms other than Compass are marked with a OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS or Ulster County Board of REALTORS Logo. Use of these search facilities other than by a consumer seeking to purchase or lease real estate is prohibited. The accuracy of all information is deemed reliable but not guaranteed and should be verified through personal inspection by and/or with appropriate professionals. The data contained herein is copyrighted by the IDX Program of OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Information Copyright 2026, OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. All rights reserved. Data last updated: 08/21/2025 01:08 PM