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.
For sale
$1,400,000
4258 Route 44, Millbrook, NY 12545
3beds
10,689sqft
Single Family Residence, Residential
Built in 1962
1.9 Acres Lot
$-- Zestimate®
$131/sqft
$-- HOA
What's special
Private three-bedroom apartmentStriking architectural detailsOutdoor gardensMultiple gathering areasSoaring ceilingsExpansive main levelHistoric character
- 115 days
- 462
- 14
Zillow last checked:
Listing updated:
Listed by:
William Pitt Sothebys Int Rlty 203-644-1471,
Stephen M. Pener 860-927-1141
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 996782
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 8
- Full bathrooms: 4
- 1/2 bathrooms: 4
Heating
- Oil
Cooling
- Central Air
Appliances
- Included: Dishwasher, Range, Refrigerator
Features
- High Ceilings
- Basement: Unfinished
- Attic: Finished,Partially Finished,Storage,Unfinished
- Number of fireplaces: 3
Interior area
- Total structure area: 10,689
- Total interior livable area: 10,689 sqft
Property
Parking
- Parking features: Driveway, Off Street, Private
- Has uncovered spaces: Yes
Features
- Levels: Two
- Has view: Yes
- View description: Mountain(s), Open
Lot
- Size: 1.9 Acres
Details
- Parcel number: 1358896966003334320000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Other,Traditional
- Property subtype: Single Family Residence, Residential
- Attached to another structure: Yes
Materials
- Frame
Condition
- Year built: 1962
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Connected, Electricity Connected, Phone Connected
Community & HOA
HOA
- Has HOA: No
Location
- Region: Millbrook
Financial & listing details
- Price per square foot: $131/sqft
- Tax assessed value: $906,400
- Annual tax amount: $19,422
- Date on market: 5/8/2026
- Cumulative days on market: 96 days
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/8/2026 | Listed for sale | $1,400,000-3.4%$131/sqft |
Source: | ||
| 1/1/2026 | Listing removed | $1,450,000$136/sqft |
Source: | ||
| 9/4/2025 | Price change | $1,450,000-3.3%$136/sqft |
Source: | ||
| 1/3/2025 | Listed for sale | $1,500,000$140/sqft |
Source: | ||
Public tax history
Tax history is unavailable.
Monthly payment
Climate risks
Neighborhood: 12545
Nearby schools
Schools provided by the listing agent
- Elementary: Elm Drive Elementary School
- Middle: Millbrook Middle School
- High: Millbrook High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.








