4258 Route 44Millbrook, NY 12545

Single Family · 3 Beds · 4 Full Baths · 4 Half Baths · 10,689 Sq. ft. | 1.90 Acres
$1,400,000 Active

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.

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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

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

4258 Route 44 Market Data

Based on the last 30 days in this zip code

$2,220,378
Average List Price
$600
Average Price per Square Foot
3
Properties Sold
123
Average Days on Market
42
Properties for Sale
Calculations provided by Reliance Network

4258 Route 44 History

Date Event Value Agent
5/8/2026Source: OneKey MLS Added to Database
May 08, 2026
5/8/2026Source: OneKey MLS Added to Database
May 08, 2026
5/9/2025Source: Hudson Valley Catskill Regional MLS Added to Database
May 09, 2025
Listing provided courtesy of William Pitt Sothebys Int RltyStephen M. Pener- MLS# 996782MLS ProviderContact Information: 203-644-1471