Date
Details
Price
Change
Source
5/08/2026
Listed
$1,400,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property 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 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.
Full Property Details
Full Property Details for 4258 Route 44
General
- Price: $1,400,000
- Taxes: $19,422
- Status: Active
- Type: Single Family
- Source: Long_Island
- MLS ID: 996782
- Updated: 5/8/2026
- Added to Site: 19 day(s) ago
Interior
- Number of Rooms: 17
- Interior Features: High Ceilings
- Number of Fireplaces: 3
- Appliances: Dishwasher, Range, Refrigerator
Rooms
Bathrooms
- Total Bathrooms: 8
- Full Bathrooms: 4
- Half Bathrooms: 4
Bedrooms
- Total Bedrooms: 3
Parking
- Parking Features: Driveway, Off Street, Private
Location
- County: Dutchess County
School Information
- High School District: Millbrook
- Elementary School: Elm Drive Elementary School
- Middle School: Millbrook Middle School
- High School: Millbrook High School
Heating & Cooling
- Central air: Yes
- Cooling Type: Central Air
- Heating Type: Oil
Utilities
- Sewer: Septic Tank
- Water: Well
- Utility Description: Cable Connected, Electricity Connected, Phone Connected
Structural Information
- Architectural Style: Colonial, Other, Traditional
- Detached/Attached: Attached
- Construction: Frame
- Basement: Yes
- Basement Desc.: Unfinished
- Unfinished Attic: Yes
- Building Size: 10689
- Square Feet: 10,689
- Sq. Ft. Source: Public Records
- Year Built: 1962
Lot Features
- Property View: Mountain(s), Open
- Mountain views: Yes
- Lot Size (Acres): 1.9
- Lot Size (Sq. Ft.): 82,764
Financial Considerations
- Tax Amount: $19,422.82
Disclosures and Reports
- Special Conditions: None
- Property ID: 135889-6966-00-333432-0000
Listed by William Pitt Sothebys Int Rlty
We Value Your Privacy
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Listing agent
— 4258 Route 44 —
William Pitt Sothebys Int Rlty
203-644-1471
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 4258 Route 44
School District:Millbrook Central School District
| Name | Grades | Distance |
|---|---|---|
Alden Place Elementary School 41 Alden Place, Millbrook, NY 12545 | 3-5 | 4.2 mi |
Elm Drive Elementary School 12 Elm Drive, Millbrook, NY 12545 | K-2 | 4.3 mi |
Millbrook Middle School 43 Alden Place, Millbrook, NY 12545 | 6-8 | 4.2 mi |
Millbrook High School 70 Church Street, Millbrook, NY 12545 | 9-12 | 4.3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 4258 Route 44
Tax History
Tax History for 4258 Route 44
Year
Property Taxes
Change
Tax Assessment
Change
2025
$19,819
37%
$906,400
—
2024
$14,431
-23%
$906,400
—
2016
$18,706
-5%
$906,400
—
2020
$19,767
4%
$906,400
—
2018
$19,022
2%
$906,400
—
2017
$18,640
1%
$906,400
—
2016
$18,403
-2%
$906,400
—
2015
$18,772
3%
$906,400
—
2015
$18,201
4%
$906,400
—
2013
$17,522
—
$906,400
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 4258 Route 44
4258 Route 44, Millbrook, NY 12545 (MLS# 996782) is a Single Family property with 3 bedrooms, 4 full bathrooms and 4 partial bathrooms. 4258 Route 44 is currently listed for $1,400,000 and was received on May 08, 2026. Want to learn more about 4258 Route 44? Do you have questions about finding other Single Family real estate for sale in Millbrook? You can browse all Millbrook real estate or contact a Coldwell Banker agent to request more information.