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4258 Route 44, Millbrook, photo 1
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4258 Route 44

$1,400,000

Est. $8,715/mo

Millbrook, NY 12545 · Dutchess County

Beds
3
Baths
6
Sqft
10,689
Status
Active
On site
132 days

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About this home

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.

Listed with William Pitt Sothebys Int Rlty · Stephen M. Pener · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 3:09 PM ET. ©2026 One Key MLS.

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Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and Private Mortgage Insurance.

$8,714.62Total / mo

Estimated Monthly Payment

Principal & interest
$6,896.03 (79.1%)
Taxes
$1,618.58 (18.6%)
Insurance
$200.00 (2.3%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

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Market Insights

The market around Millbrook, NY

Current Listings

New in the last 30 days

9

Sep 2026

Average Price

Active listings

$3,639,242

Sep 2026

Average Days on Market

Active listings

148 days

Sep 2026

Computed from 43 active OneKey MLS listings in Millbrook, NY.

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