4258 Highway 44

Millbrook, NY 12545

$1,450,000
Price
3
Beds
10,689 Sq. Ft.
$136 / Sq. Ft.
10,689
Sq. Ft.
$136
per Sq. Ft.
a view of a house with a backyard and chairs
front view of a house with a yard
a view of a house with a yard
an aerial view of a house with a yard and a large tree
an aerial view of a house with a yard large trees
a view of a house with a big yard potted plants and large tree
a view of a chair and table on the garden
a front view of a house with garden
a view of a big dining room with furniture window and outside view
a view of a dining room with furniture
a dining room with furniture and a large window
a view of a dining room with furniture window and outside view
an outdoor space with seating
a living room with furniture and a fireplace
a view of a chairs and tables in patio with a barbeque grill
a dining room with furniture and wooden floor
a view of a dining room with furniture window and wooden floor
a living room with furniture fireplace and a large window
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture
a living room with furniture a fireplace and a chandelier
a view of a dining room with furniture window and outside view
a dining room with furniture and a chandelier
a view of balcony with two chairs and wooden fence
a kitchen with a stove and cabinets
a kitchen with refrigerator and cabinets
a view of a house with a yard
a backyard of a house with table and chairs
a living room with furniture and a floor to ceiling window
a living room with furniture a flat screen tv and a floor to ceiling window
a living room with furniture a rug and a flat screen tv
a dining room with wooden floor a chandelier a wooden table and chairs
a kitchen with a large window appliances and cabinets
a bedroom with a bed a couch and a flat tv screen on dresser
a living room with furniture a bookshelf and a window
a sign on the side of a building

Description

This distinctive property in the heart of Dutchess County combines historic character with over 10,000 square feet of versatile residential and commercial potential. Originally built in the 19th century as a Congregational church, the building has enjoyed a rich history and now offers endless possibilities for its next chapter. The expansive main level features multiple gathering areas, soaring ceilings, and striking architectural details that create a unique backdrop for a wide range of uses—whether...This distinctive property in the heart of Dutchess County combines historic character with over 10,000 square feet of versatile residential and commercial potential. Originally built in the 19th century as a Congregational church, the building has enjoyed a rich history and now offers endless possibilities for its next chapter. The expansive main level features multiple gathering areas, soaring ceilings, and striking architectural details that create a unique backdrop for a wide range of uses—whether hospitality, creative ventures, or professional space. Complementing the generous interior, outdoor gardens and landscaped grounds provide space for events or a serene setting for relaxation. Above the main level, a private three-bedroom apartment offers comfortable living with a deck overlooking the surrounding countryside. This rare combination of historic charm, substantial square footage, and adaptable layout makes the property ideal for a live/work arrangement, an investment opportunity, or a visionary redevelopment. With its rich character and flexible design, it presents a truly exceptional opportunity in one of the Hudson Valley’s most desirable locations.

Property Details for 4258 Highway 44

City/Township
Washington
View
Mountain(s), Open
Architectural Style
Colonial, Other, Traditional
Waterfront
No
LISTING UPDATED: 09/25/2025 04:09 PM

Property Details for 4258 Highway 44

StatusActive
MLS #809427
Days on Market346
Taxes$19,423 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built1962
Lot Size1.90 AC / 82,764 SF
CountyDutchess County

Location

Listing Courtesy of William Pitt Sothebys Int Rlty
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Building Information for 4258 Highway 44

Stories-Year Built1962Building Size-Lot Size1.90 AC / 82,764 SF

Payment Calculator

$8,784 per month

30 year fixed, 6.28% Interest

Principal and Interest

$7,165

Property Taxes

$1,619

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 4258 Highway 44

Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: Yes
  • Structure Type: true
  • Levels: Two
  • State Or Province: NY
School Information
  • School District: Millbrook
  • Elementary School District: Millbrook
  • Elementary School: Elm Drive Elementary School
  • Middle Or Junior School District: Millbrook
  • Middle Or Junior School: Millbrook Middle School
  • High School District: Millbrook
  • High School: Millbrook High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 135889-6966-00-333432-0000
  • Tax Assessed Value: $906,400.00
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: Colonial, High Ceilings, Mountain(s), Open, Other, Traditional, Well
  • Interior Features: High Ceilings
  • Appliances: Dishwasher, Range, Refrigerator
  • Total Rooms: 17
  • Basement: Unfinished
  • Attic Description: Finished,Partially Finished,Storage,Unfinished
  • Fireplaces Total: 3
  • Location Amenities: Other/See Remarks, High Ceilings, Mountain Views
  • Basement: Yes
Exterior Features
  • Exterior Property Features: Driveway, Off Street, Private
  • Elevation Certificate: No
  • Construction Materials: Frame
  • Pool Private: No
Lot Information
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway, Off Street, Private
  • Garage: No
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Oil
  • Heat Fuel Type: Oil
  • Sewer: Septic Tank
  • Water Source: Well
  • Utilities: Cable Connected, Electricity Connected, Phone Connected
Green Features
  • Green Features: Dishwasher, Range, Refrigerator, Oil
Agent
Payment and Rate
  • Down Payment Resource: No

Public Records for 4258 Highway 44

Taxable ValueLand$76,100Additions$830,300Total$906,400
Tax Record2024$14,431 ($1,203 / month)
Home Facts
Total Finished SqFt10,689 SqFtAbove Grade Finished SqFt10,689 SqFtUnfinished Basement SqFt7,896 SqFtStories2Lot Size82,764 SqFtStyleRestaurantYear Built1962ZoningRR10CountyDUTCHESSAPN135889 6966-00-333432-0000

Schools near 4258 Highway 44

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 4258 Highway 44, Millbrook, NY 12545

4258 Highway 44 is a single family home for sale in Millbrook, NY 12545. This property was listed for sale on January 3, 2025 by William Pitt Sothebys Int Rlty, it's currently listed at $1,450,000. 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. 4258 Highway 44 is a 3-bed, 8-bath, 10,689 sqft single family home built in 1962.

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 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 William Pitt Sothebys Int Rlty

Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 12/15/2025 07:30 PM. All data is obtained from various sources and may not have been verified by broker orMLS GRID. Supplied Open House Information is subject to change without notice. All informationshould be independently reviewed and verified for accuracy. Properties may or may not be listed bythe office/agent presenting the information.