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$1,450,000
7 Days On Site

395 Boston Post Road
Madison, CT 06443

For Sale|Single Family Residence|Coming Soon
4
Beds
5
Total Baths
5
Full Baths
3,340
SqFt
$434
/SqFt
1828
Built
County:
New Haven
Listing courtesy of Laurie Mazzeo of William Pitt Sotheby's Int'l Office Phone: (203) 245-6700 Broker Contact: (203) 641-6837
Call Now: 203-641-3233
Is this the listing for you? We can help make it yours.
203-641-3233
395 Boston Post Road395 Boston Post Road395 Boston Post Road395 Boston Post Road
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Mortgage Calculator

Monthly Payment (Est.)

$6,615
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

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Listing Snapshot
Price 
$1,450,000
Days On Site 
7 Days
Bedrooms 
4
Inside Area (SqFt) 
3,340 sqft
Total Baths 
5
Full Baths 
5
Partial Baths 
N/A
Lot Size 
0.92 Acres
Year Built 
1828
MLS® Number 
24158296
Status 
Coming Soon
Property Tax 
$17,816
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
2 days agoListing updated with changes from the MLS®
a week agoListing first seen on site
General Features
Acres 
0.92
Foundation 
StoneConcrete Perimeter
Garage 
Yes
Garage Spaces 
2
Parking 
AsphaltPavedGarage Door OpenerPrivateDriveway
Parking Spaces 
5
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
SqFt Total 
3779
Style 
Colonial
Water Source 
Public
Zoning 
R-1
Interior Features
Appliances 
DishwasherElectric CooktopDryerMicrowaveRefrigeratorOvenWasherGas Water HeaterRange Hood
Basement 
PartialUnfinished
Cooling 
Central Air
Fireplace 
Yes
Fireplaces 
1
Heating 
Hot Water
Studio Apt 
Dimensions - 25 x 19Level - Upper
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Exterior Features
Construction Details 
Vinyl SidingFrameClapboard
Fencing 
Wood
Lot Features 
Level
Other Structures 
Shed(s)
Patio And Porch 
PatioPorchScreened
Roof 
Asphalt
Windows/Doors 
French Doors
Community Features
Community Features 
GolfTennis Court(s)
Schools
School District
Unknown
Elementary School
Neck River
Middle School
Per Board of Ed
High School
Daniel Hand
Listing courtesy of Laurie Mazzeo of William Pitt Sotheby's Int'l Office Phone: (203) 245-6700 Broker Contact: (203) 641-6837



The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.
Last checked: 2026-03-26 09:59 PM UTC.

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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