Movoto Real Estate
Sold on 05/04/2026
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395 Boston Post Rd, Madison, CT 06443

  • $1,400,000

    Last sold 05/04/2026 after 46 Days

  • 4

    bed

  • 5

    bath

  • 3,779

    Sqft ($370/Sqft)

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About 395 Boston Post Rd

Property type House
Year built 1828
HOA fee $0/month
Lot size 0.92 Acre
Movoto estimate
Parking 2 garage spaces
Property description
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.
Listed by
Listing Agent - Laurie Mazzeo
Listing Office - William Pitt Sotheby's Int'l
Source: CONNECT MLS mls logo
MLS#24158296 • last updated 2 months ago
Movoto checked CONNECT MLS for data 3 minutes ago
Overview
Cooling/AC Central Air
Heating Hot Water, Gas In Street
Levels/Style Colonial
Type Single Family For Sale
SqFt 3779
Status Closed
MLS # 24158296
Lot Size (Acres) 0.92
Property Tax 17816
Property Condition No/Resale
Interior
Total # of Bathrooms 5
# of Full Baths 5
Total # of Bedrooms 4
Laundry Upper Level
Total # of Rooms 9
Exterior
Roofing Asphalt Shingle
# Parking Spaces 5
# Garage Spaces 2
Parking Detached Garage, Paved, Driveway
Amenities / Utilities
Sewer/ Septic Septic
Location
Waterfront Not Applicable
Elementary School Neck River
Intermediate School Per Board Of Ed
High School Daniel Hand
Middle School Per Board Of Ed
APN 1155692
Directions North Side Of Boston Post Road On West Side Of Town. Look For Sign.
$1.44M
Range: $1.04M-$1.84M
Last 30 days 
  • May 2026
    mls logo MLS # 24158296
  • May 4, 2026 Sold
    $1,400,000 (-3.4%)
  • Apr 6, 2026 Under Contract
  • Apr 1, 2026 Under Contract - Continue To Show
  • Mar 19, 2026 Listed
    $1,450,000 (+106.3%)
  • Feb 2021
    mls logo MLS # 170300921
  • Feb 26, 2021 Sold
    $703,000
  • Jan 20, 2021 Deposit
  • Dec 6, 2020 Show
  • Jun 3, 2020 Listed
    $745,000
  • Feb 2021
    Public Records
  • Feb 26, 2021 Sold
    $703,000 (-5.6%)
  • Jan 2020
    mls logo MLS # 170183288
  • Jan 3, 2020 Price Change
    $745,000 (-6.3%)
  • Apr 23, 2019 Listed
    $795,000
  • Aug 2016
    mls logo MLS # N10159192
  • Aug 11, 2016 Listed
    $795,000 (+3.9%)
  • Aug 2003
    mls logo MLS # M9074700
  • Aug 11, 2003 Closed
    $765,000
  • Apr 21, 2003 Listed
    $799,000
  • Aug 2003
    Public Records
  • Aug 8, 2003 Sold
    $765,000 (-4.3%)
  • 395 Boston Post Rd
    $1.4M
  • 06443
    $998K +26% y/y
  • Madison
    $930K 0% y/y
No chart available
Statistics calculated by Movoto

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9/10
Source: GreatSchools.org © 2026. All rights reserved.

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