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395 Boston Post Road, 
Madison, CT 06443

$1,450,000


4

Beds


5

Baths


3,779

Sq Ft


Single Family

Pending

Listed by

Laurie Mazzeo, (203) 641-6837

William Pitt Sotheby'S Int'L, (203) 245-6700

(203) 245-6700

Last updated:

April 1, 2026, 03:38 PM

MLS#

24158296

Source:

CT

About This Home

395 Boston Post Road

Introducing the historic Ebenezer Dudley Home, circa 1828, a beautifully preserved residence set along the iconic stretch of Boston Post Road in the charming shoreline town of Madison, Connecticut. Situated on nearly an acre of picturesque grounds, this special property seamlessly blends early New England character with thoughtful modern updates, offering both historic charm and everyday comfort. During the past five years of ownership, the current homeowners have undertaken extensive improvements and updates throughout the property. Among them are the addition of a spectacular wraparound screened porch with bluestone flooring, a birch board ceiling and wood burning stove, the conversion to natural gas heat and tankless hot water, installation of a new 50-year architectural shingle roof, an updated kitchen, and a beautifully renovated first-floor bathroom, are just a few of the many thoughtful enhancements made to the home. A significant addition completed in 2003 expanded the home's living space to include the kitchen, family room, and a spacious primary bedroom suite designed for modern living. The private primary suite features a generous full bath, a dressing room and walk-in closet, creating a comfortable and elegant retreat. Two additional ensuite bedrooms complete the second floor, along with a large, gracious landing that connects the three bedrooms and enhances the sense of space.

Home Facts

Single Family

5 Baths

4 Bedrooms

Built in 1828

Price Summary

1,450,000

$383 per Sq. Ft.

MLS #:

24158296

Last Updated:

April 1, 2026, 03:38 PM

Added:

14 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

5

Interior

Living Area:

3,779 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial

Building Area:

3,779 Sq. Ft.

Year Built:

1828


Lot

Lot Size (Sq. Ft):

40,075


Finances & Disclosures

Finances

Price:

$1,450,000

Price per Sq. Ft:

$383 per Sq. Ft.

Source:CT
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.