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4258 Route 44, 
Millbrook, NY 12545

$1,400,000


3

Beds


8

Baths


10,689

Sq Ft


Single Family

Active

Listed by

Stephen M. Pener

William Pitt Sothebys Int Rlty

Last updated:

May 16, 2026, 10:48 AM

MLS#

996782

Source:

OneKey MLS

About This Home

4258 Route 44

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.

Home Facts

Single Family

8 Baths

3 Bedrooms

Built in 1962

Price Summary

1,400,000

$130 per Sq. Ft.

MLS #:

996782

Last Updated:

May 16, 2026, 10:48 AM

Added:

10 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

8

Full Bathrooms:

4

Interior

Living Area:

10,689 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial, Traditional

Building Area:

10,689 Sq. Ft.

Year Built:

1962


Lot

Lot Size (Sq. Ft):

82,764


Finances & Disclosures

Finances

Price:

$1,400,000

Price per Sq. Ft:

$130 per Sq. Ft.

Source:OneKey MLS
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.