$1,450,000

395 Boston Post Road, Madison, CT 06443

  • 4 beds |
  • 5 baths |
  • 3,779 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1828
  • Property Lot Size Icon0.92acre lot
  • Property Parking Icon 2 car garage
  • Property Price Per Square Feet Icon $384/sqft
  • Property List Date Icon Listed 8 days ago

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.

Listing Status:
Coming Soon
Date Added:
March 19, 2026
Data Last Updated:
March 28, 2026 at 12:50AM
Listing Office:
William Pitt Sotheby's Int'l : (203) 245-6700
Listing Agent:
Laurie Mazzeo : (203) 641-6837
MLS ID:
24158296
  • General: Auto Garage Door OpenerCable - Available
  • Appliances: Electric CooktopWall OvenMicrowaveRange HoodRefrigeratorDishwasherWasherElectric Dryer
  • Laundry: Upper Level
  • Basement: PartialUnfinished
  • A/C: Central Air
  • Heating: Hot WaterGas In Street
  • Fireplace: Fireplaces: 1
  • General: Porch-Wrap AroundPorch-ScreenedShedPorchStone WallFrench DoorsPatio
  • Style: Colonial
  • Parking: Parking spaces: 5
  • Roofing: Asphalt Shingle
  • County: New Haven
  • Driveway: PrivatePavedAsphalt
  • Zoning: R-11155692
  • Water: Public Water Connected
  • Sewer: Septic

This listing courtesy of Laurie Mazzeo , William Pitt Sotheby's Int'l

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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Location

Schools Nearby

J

J. Milton Jeffery Elementary School

331 Copse Rd, Madison, CT, 06443

Grades KG-3

1.13 miles away

W

Walter C. Polson Middle School

302 Green Hill Rd, Madison, CT, 06443

Grades 6-8

1.18 miles away

D

Daniel Hand High School

286 Green Hill Rd, Madison, CT, 06443

Grades 9-12

1.00 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.

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