395 Boston Post Road, Madison, CT 06443 - Photo 1

1/1

$1,400,000

Sold
Closed
Single Family
4 Beds
5 Full Baths
3,779 Sq. Ft.
2 Car Garage

1/1

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.

Full Property Details

Full Property Details for 395 Boston Post Rd

General

Sold For: $1,400,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24158296
Added to Site: 61 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
Sold by RE/MAX Heritage, Steven Elek

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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

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Schools

Schools serving 395 Boston Post Rd

School District:Madison School District

Name	Grades	Distance
J. Milton Jeffrey Elementary School 331 Copse Road, Madison, CT 06443	K-3	1.1 mi
Dr. Robert H. Brown Middle School 980 Durham Road, Madison, CT 06443	4-5	4.3 mi
Walter C. Polson Upper Middle School 302 Green Hill Road, Madison, CT 06443	6-8	1.2 mi
Daniel Hand High School 286 Green Hill Road, Madison, CT 06443	9-12	1 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

Date

Details

Price

Change

Source

5/01/2026

Sold

$1,400,000

-3.45%

MLS

3/29/2026

Listed

$1,450,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Active
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4
Beds
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Beds
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395 Boston Post Road, Madison, CT 06443 (MLS# 24158296) is a Single Family property that was sold at $1,400,000 on May 01, 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.

395 Boston Post Rd Madison, CT 06443