SoldMay 1, 2026

Bought with Steven Elek

Source: SmartMLS Connecticut #24158296

395 Boston Post Rd, Madison Center, CT, 06443

$1,400,000

4
5
5
3779 sq. ft.
0.92 ac.

SingleFam

1 day on the market

Sold: May 1, 2026

What's around 395 Boston Post Rd

About this property

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.

Looking for more information on 395 Boston Post Rd?

Explore comparables, sales history and growth for this property.
Learn more

Similar properties sold nearby

SoldJul 8, 2026
$805,000
60 Bradley Corners Road
New Haven County CT 06443
4
3
2
Single-Family
Listing courtesy of William Pitt Sotheby's Int'l and Betsy Grauer Realty, Inc
SoldJul 7, 2026
$1,000,000
125 Wildcat Road
New Haven County CT 06443
4
3
10
Single-Family
Listing courtesy of Coldwell Banker Realty and William Pitt Sotheby's Int'l
SoldJul 2, 2026
$735,000
40 Harkness Drive
Madison CT 06443
4
3
2
Single-Family
Listing courtesy of Coldwell Banker Realty and Berkshire Hathaway NE Prop.

Other properties sold by Steven Elek

SoldJun 18, 2026
$1,050,000
95 Chestnut Hill Rd
Middlesex County CT 06419
3
3
4
Single-Family
Listing courtesy of William Pitt Sotheby's Int'l and REMAX Heritage | Madison
SoldJun 16, 2026
$920,000
111 Acorn Road
Madison CT 06443
3
3
5
Single-Family
Listing courtesy of Coldwell Banker Realty and REMAX Heritage | Madison
SoldMay 13, 2026
$120,000
15 Cutlery Avenue
Meriden CT 06451
Land
Listing courtesy of Advise Realty Services and REMAX Heritage | Madison

Browse properties sold in nearby areas

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Email
© 2026 RateMyAgent