About 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.
Features of 4258 Route 44
| MLS® # | 996782 |
|---|---|
| Price | $1,400,000 |
| Bedrooms | 3 |
| Bathrooms | 8.00 |
| Full Baths | 4 |
| Half Baths | 4 |
| Square Footage | 10,689 |
| Acres | 1.90 |
| Year Built | 1962 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Colonial, Other, Traditional |
| Status | Active |
Community Information
| Address | 4258 Route 44 |
|---|---|
| City | Millbrook |
| County | Dutchess County |
| State | NY |
| Zip Code | 12545 |
Amenities
| Utilities | Cable Connected, Electricity Connected, Phone Connected |
|---|---|
| Parking | Driveway, Off Street, Private |
| View | Mountain(s), Open |
| Is Waterfront | No |
| Has Pool | No |
Interior
| Interior Features | High Ceilings |
|---|---|
| Appliances | Dishwasher, Range, Refrigerator |
| Heating | Oil |
| Cooling | Central Air |
| Has Basement | Yes |
| Basement | Unfinished |
| Fireplace | Yes |
| # of Fireplaces | 3 |
Exterior
| Construction | Frame |
|---|
School Information
| District | Millbrook |
|---|---|
| Elementary | Elm Drive Elementary School |
| Middle | Millbrook Middle School |
| High | Millbrook High School |
Additional Information
| Date Listed | May 8th, 2026 |
|---|---|
| Days on Market | 121 |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | William Pitt Sothebys Int Rlty |
|---|