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$1,450,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 5 Full Baths
  • 3,779 Sq. Ft.
  • 2 Car Garage
  • Updated 2 days ago
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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.

Full Property Details for 395 Boston Post Rd

General

  • Price: $1,450,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24158296
  • Updated: 3/29/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 9
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Electric Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 5

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: Cathedral Ceiling, Ceiling Fan, Dressing Room, Full B, 15 x 25, Upper
  • Bedroom 1: Bedroom - Full Bath, Wide Board Floor, 8 x 19, Main
  • Bedroom 2: Bedroom - Built-Ins, Full Bath, Wide Board Floor, 14 x 16, Upper
  • Bedroom 3: Bedroom - Full Bath, Walk-In Closet, Wide Board Floor, 14 x 16, Upper

Other Rooms

  • Living Room: Living Room - French Doors, Wide Board Floor, 14 x 12, Main
  • Family Room: Family Room - Gas Log Fireplace, Wide Board Floor, 15 x 25, Main
  • Eat In Kitchen: Eat-In Kitchen - Remodeled, Granite Counters, French Doors, Island, Pantry, Tile, 15 x 20, Main
  • Dining Room: Dining Room - French Doors, Wide Board Floor, 19 x 15, Main
  • Laundry: Upper Level

Exterior

  • Exterior Features: Porch-Wrap Around, Porch-Screened, Shed, Porch, Stone Wall, French Doors, Patio
  • Color: Sage

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 5
  • Parking: Detached Garage, Paved, Driveway

Location

  • County: New Haven
  • Driving Directions: North side of Boston Post Road on West side of town. Look for Sign.

School Information

  • Elementary School: Neck River
  • Middle School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • High School: Daniel Hand

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water, Gas In Street
  • Heating Fuel: Gas In Street
  • Water Heater: Natural Gas, Tankless Hotwater

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Vinyl Siding
  • Basement Desc.: Partial, Unfinished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,779
  • Above Ground: 3,779 Sq. Ft.
  • Year Built: 1828

Lot Features

  • Lot Size (Acres): 0.92
  • Driveway/Sidewalk: Private, Paved, Asphalt
  • Zoning: R-1
  • Lot Description: Fence - Wood, Fence - Partial, Level Lot

Financial Considerations

  • Assessment Amount: $794,300
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1155692

Listed by William Pitt Sotheby's Int'l, Laurie Mazzeo

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Listing agent

— 395 Boston Post Rd —

  • Laurie Mazzeo

    William Pitt Sotheby's Int'l

Agent Contact: (203) 641-6837 Office Contact: (203) 245-6700

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 395 Boston Post Rd

School District:Madison School District
NameGradesDistance
J. Milton Jeffrey Elementary School
331 Copse Road, Madison, CT 06443
K-31.1 mi
Dr. Robert H. Brown Middle School
980 Durham Road, Madison, CT 06443
4-54.3 mi
Walter C. Polson Upper Middle School
302 Green Hill Road, Madison, CT 06443
6-81.2 mi
Daniel Hand High School
286 Green Hill Road, Madison, CT 06443
9-121 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 395 Boston Post Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/29/2026
Listed
$1,450,000
106.26%
MLS
2/25/2021
Sold
$703,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 395 Boston Post Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$17,816
2%
$794,300
—
2023
$17,475
15%
$794,300
57%
2023
$15,186
3%
$506,700
1%
2022
$14,690
2%
$499,500
—
2021
$14,411
2%
$499,500
—
2020
$14,164
—
$499,600
—
2019
$14,164
5%
$499,600
4%
2018
$13,487
3%
$481,000
—
2017
$13,131
3%
$481,000
—
2016
$12,742
3%
$481,000
—
2015
$12,391
2%
$481,000
—
2014
$12,107
11%
$481,000
-10%
2010
$10,911
—
$535,100
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by William Pitt Sotheby's Int'l, Laurie Mazzeo

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395 Boston Post Road, Madison, CT 06443 (MLS# 24158296) is a Single Family property with 4 bedrooms and 5 full bathrooms. 395 Boston Post Road is currently listed for $1,450,000 and was received on March 29, 2026. Want to learn more about 395 Boston Post Road? Do you have questions about finding other Single Family real estate for sale in Madison? You can browse all Madison real estate or contact a Coldwell Banker agent to request more information.

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