4258 Route 44 Millbrook, NY $ 1,450,000
4258 Route 44
$ 1,450,000
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4258 Route 44

Millbrook, NY, 12545
$ 1,450,000
Bedrooms3 Baths4.4 Sq 10,689

Monthly Estimate*

$ 9,046

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Single Family Home for sale in Millbrook, NY

for $1,450,000 with 3 bedrooms and 4 full baths, 4 half baths. This 10,689 square foot home was built in 1962 on a lot size of 1.9.

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.

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Single Family Active

Price

$ 1,450,000

Bedrooms

3

Full Bath

4

Half Bath

4

Property Type

Single Family

Taxes

$ 19,422

Style

Colonial,,Traditional

Lot Size

1.9

Year Built

1962

Town/City

Millbrook

County/Region

Dutchess

MLS | Web ID

809427

Features
Interior
Interior Amenities High Ceilings
Basement Unfinished
Total Fireplaces 3
Basement Features Unfinished
Basement (Y/N) Y
Half Baths 4
Total Bedrooms 3
Total Baths 8
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General
Sewer Septic Tank
Heating Oil
Cooling Central Air
Utilities Cable Connected Electricity Connected Phone Connected
Appliances Dishwasher Range Refrigerator
Architectural Style Colonial Other Traditional
Construction Materials Frame
Year Built 1962
View Mountain(s) Open
Property Subtype Single Family Residence
Tax Year 2024
Parcel Number 135889-6966-00-333432-0000
County Dutchess County
Property Type Residential
HOA N
Garage Y/N N
Total Rooms 17
Full Baths 4
High School Millbrook High School
City Washington
Senior Community Y/N N
High School District Millbrook
Carport Y/N N
Elementary School Elm Drive Elementary School
Property Attached Y/N Y
Tax Annual Amount 19422.82
Showing Instructions Advanced notification required
Middle/Junior High School Millbrook Middle School
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Millbrook
Elementary School District Millbrook
Tax Assessed Value 906400
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Exterior
Parking Features Driveway Off Street Private Driveway Off Street Private
Water Source Well
Building Area Total 10689
Waterfront Y/N N
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Internal Only
Street Number 1 4258
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* Excluded Features
List By
Stephen M. Pener

Listing Agent

William Pitt Sothebys Int Rlty

Broker

203-644-1471

Contact

Affordability Calculator

$10,665
Per Month
85%
15%
0%
Monthly Principal & Interest
$9,046
Monthly Property Taxes
$1,619
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4099747 Elementary School
4098829 Middle School
Millbrook High School High School
Pricing History
DatePricePrice ChangeDescription
9/4/2025$1,450,000 -3.33% Price Down
1/4/2025$1,500,000 Listed Price

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4258 Route 44, Millbrook, NY, 12545 is a Single Family Home for sale at $1,450,000 with 10,689 sqft and a lot size of 1.9. 4258 Route 44 has 3 bedrooms, 4.4 baths, and was built in 1962. The property's zip code is 12545 which is in Millbrook, NY