
4258 Route 44 Overview
- Time on Site:
- 52 days
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.
4258 Route 44 Facts & Features
- Type Single Family
- Sq. ft. 10,689
- Price/Sq.ft. $131
- Lot 1.90 Acres
Details
General
Association/HOA
- Association: No
School Information
- School District: Millbrook
- Elementary School: Elm Drive Elementary School
- Middle Or Junior School: Millbrook Middle School
- High School: Millbrook High School
Building Information
- Year Built: 1962
Location/Region
- County Or Parish: Dutchess County
- Postal City: Millbrook
Rent/Lease Information
- Lease Considered: No
Tax Information
- Tax Annual Amount: 19422.82
- Tax Assessed Value: 906400
- Tax Year: 2024
General Information
- Parcel Number: 135889-6966-00-333432-0000
- Property Sub Type: Single Family Residence
- Property Type: Residential
- Senior Community: No
- Special Listing Conditions: None
Interior
Parking Information
- Garage: No
Beds/Baths
- Bathrooms Full: 4
- Bathrooms Half: 4
- Bathrooms Total: 8
- Bedrooms Total: 3
Building Interior
- Building Area Source: Public Records
- Building Area Total: 10689
- Building Area Units: Square Feet
General Information
- Appliances: Dishwasher,Range,Refrigerator
- Cooling: Central Air
- Fireplaces Total: 3
- Heating: Oil
- Interior Features: High Ceilings
- Levels: Two
- Living Area: 10689
- Living Area Source: Public Records
- Rooms Total: 17
Exterior
Parking Information
- Parking Features: Driveway,Off Street,Private
Lot Information
- Lot Size Acres: 1.9
- Lot Size Square Feet: 82764
- Water Source: Well
Waterfront/View
- View: Mountain(s),Open
- Waterfront: No
Building Exterior/Construction
- Architectural Style: Colonial,Other,Traditional
- Construction Materials: Frame
- Property Attached: Yes
General Information
- Carport: No
- Pool Private: No
- Sewer: Septic Tank
- Utilities: Cable Connected,Electricity Connected,Phone Connected
4258 Route 44 Monthly Cost
4258 Route 44 Market Data
Based on the last 30 days in this zip code
4258 Route 44 History
| Date | Value | Agent |
|---|---|---|
| 5/8/2026Source: OneKey MLS | May 08, 2026 |
|
| 5/8/2026Source: OneKey MLS | May 08, 2026 |
|
| 5/9/2025Source: Hudson Valley Catskill Regional MLS | May 09, 2025 |
Contact Information: 203-644-1471







































