395 Boston Post Rd

Madison, CT 06443

$1,450,000
Price
4
Beds
3,779 Sq. Ft.
$384 / Sq. Ft.
3,779
Sq. Ft.
$384
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Coming Soon
Coming Soon
Welcome to 395 Boston Post Road!
The Ebenezer Dudley House
Newly paved driveway-2021
Charming entry with white picket fence.
Beautiful 2-story foyer flooded with natural light.
Wide plank hardwood floors throughout most of the home!
Light and bright. French doors leading to the formal living room.
The living room is in the front of the house connected to the front door entry foyer.
French doors lead to the dining room.
First floor bedroom with connecting full bath. This room can be also used as an office or study.
First floor full bath, beautifully renovated and connecting to the first floor bedroom/office and the hallway.
The hub of the home! Open to the kitchen, 2-story foyer and dining room. This space is perfect for gatherings or just enjoying the new natural gas fireplace.
Beautiful hardwood floors.
New natural gas fireplace added in 2023.
Spacious updated eat-in kitchen with generous pantry and Island with wood countertop.
New appliances include-Bosch dishwasher, Bosch microwave drawer, Double wall ovens, 36" induction cooktop as well as granite countertops and a new double stainless steel sink.
Heated tile flooring in the kitchen.
French doors lead to the gorgeous screened wrap around porch added in 2022.
This space is so special! Bluestone flooring, birch board ceiling and wood burning stove. What a wonderful place to relax and enjoy the stunning yard as well as a wonderful gathering space for friends and family!
Wood burning fireplace with chimney.
Dining on the porch! What could be better?
Great view of the wrap around screened porch and lush yard.
Mature landscaping and established gardens create a private and colorful setting.
Large primary bedroom suite with full bath, a dressing room as well as a walk-in closet.
Beautiful hardwood floors and natural light throughout.
Luxurious primary bath with double vanity, large tile shower and claw foot tub.
There is an additional water closet complete with toilet and sink as well as a window.
Ensuite with full bath.
Ensuite with full bath and built-ins.
Studio above garage.
What a bonus space to use as a guest suite, gym, office, you name it!
Light and bright complete with a full bath and heat and air conditioned.
Gorgeous!
The shed is located behind the detached garage.
Private new outdoor shower.
A short walk or bike ride to Long Island Sound, downtown Madison and Surf Club Beach.
1st floor
2nd Floor
Studio above garage

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...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.
  1. Listed by Laurie Mazzeo • William Pitt Sotheby's Int'l
    P: (203)-641-6837 C: (203)-641-6837 lmazzeo@wpsir.com

Property Details for 395 Boston Post Road

Basement Description
Partial, Unfinished
Direct Waterfront
No
Expected Active Date
03-27-2026
Garages Number
2
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Detached Garage, Paved, Driveway
Swimming Pool
No
LISTING UPDATED: 03/20/2026 04:05 PM

Property Details for 395 Boston Post Road

StatusComing Soon
MLS #24158296
Days on Market-
Taxes$17,816 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1828
Lot Size0.92 AC / 40,075 SF
CountyNew Haven County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of William Pitt Sotheby's Int'l, Laurie Mazzeo
Add your commute

Building Information for 395 Boston Post Road

Stories-Year Built1828Building Size-Lot Size0.92 AC / 40,075 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$8,522 per month

30 year fixed, 6.11% Interest

Principal and Interest

$7,037

Property Taxes

$1,485

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 395 Boston Post Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: North side of Boston Post Road on West side of town. Look for Sign.
  • Elementary School: Neck River
  • Flood Zone: No
  • High School: Daniel Hand
  • Intermediate School: Per Board of Ed
  • Latitude: 41.278594
  • Longitude: -72.61488
  • Middle Jr High School: Per Board of Ed
  • Neighborhood Amenities: Golf Course, Health Club, Library, Medical Facilities, Private School(s), Public Rec Facilities, Shopping/Mall, Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 5
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $17,816
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch-Wrap Around, Porch-Screened, Shed, Porch, Stone Wall, French Doors, Patio
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Electric Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer
  • Attic Description: Unfinished, Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Home Automation: Lock(s), Thermostat(s)
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Laundry Room Info: Upper Level
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: French Doors,Wide Board Floor
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 12.0
Room 2
  • Room Entry Order: 2
  • Room Features: French Doors,Wide Board Floor
  • Room Length: 19.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 15.0
Room 3
  • Room Entry Order: 3
  • Room Features: Remodeled,Granite Counters,French Doors,Island,Pantry,Tile Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 20.0
Room 4
  • Room Entry Order: 4
  • Room Features: Gas Log Fireplace,Wide Board Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 25.0
Room 5
  • Listing Key: 4C8E61923E2D3B0FE0631A01100A5C33
  • Room Entry Order: 5
  • Room Features: Full Bath,Wide Board Floor
  • Room Length: 8.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 19.0
Room 6
  • Room Entry Order: 6
  • Room Features: Cathedral Ceiling,Ceiling Fan,Dressing Room,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 25.0
Room 7
  • Room Entry Order: 7
  • Room Features: Built-Ins,Full Bath,Wide Board Floor
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 16.0
Room 8
  • Room Entry Order: 8
  • Room Features: Full Bath,Walk-In Closet,Wide Board Floor
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 16.0
Room 9
  • Listing Key: 4C8E61923E2D3B0FE0631A01100A5C33
  • Room Entry Order: 9
  • Room Features: Full Bath,Tub w/Shower,Wall/Wall Carpet,Laminate Floor
  • Room Length: 25.0
  • Room Level: Upper
  • Room Type: Studio Apt
  • Room Width: 19.0
Property
Property and Assessments
  • Color: Sage
  • Construction Description: Frame
  • Driveway Type: Private, Paved, Asphalt
  • Exterior Siding: Clapboard, Vinyl Siding
  • Foundation Type: Concrete, Stone
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1828
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Detached, Second Floor
  • In Law Apartment: Possible
  • Sq Ft Description: The house is 3340 square feet The Studio above the detached garage is 439 square feet
  • Living Area SQFT Per Public Records: 3340
Lot Information
  • Lot Description: Fence - Wood, Fence - Partial, Level Lot
  • Parcel Number: 1155692
  • Sq Ft Est Heated Above Grade: 3779.0
  • Sq Ft Total: 3779.0
  • Zoning: R-1
Utilities
  • Heat Fuel Type: Gas In Street
  • Hot Water Description: Natural Gas, Tankless Hotwater
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 395 Boston Post Road

DateEvent & SourcePriceAppreciation
Feb 25, 2021

Closed (Public Record)

Public Record #1453151750

$703,000

+447.9% / yr

Mar 28, 2013

Closed (Public Record)

Public Record #350953802

$1—
Jul 18, 2011

Closed (Public Record)

Public Record #327141795

$1

-81.8% / yr

Aug 8, 2003

Closed (Public Record)

Public Record #126310095

$765,000

+11.6% / yr

Sep 5, 1997

Closed (Public Record)

Public Record #92238866

$399,900—
Sep 5, 1997

Closed (Public Record)

Public Record #92238865

$125,000—
Jul 1, 1996

Closed (Public Record)

Public Record #92239315

$125,000—
DateEvent & SourcePrice
02/25/2021

Closed (Public Record)

Public Record #1453151750

$703,000

+447.9% / yr

03/28/2013

Closed (Public Record)

Public Record #350953802

$1
07/18/2011

Closed (Public Record)

Public Record #327141795

$1

-81.8% / yr

08/08/2003

Closed (Public Record)

Public Record #126310095

$765,000

+11.6% / yr

09/05/1997

Closed (Public Record)

Public Record #92238866

$399,900
09/05/1997

Closed (Public Record)

Public Record #92238865

$125,000
07/01/1996

Closed (Public Record)

Public Record #92239315

$125,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 395 Boston Post Road

Taxable ValueLand$313,500Additions$480,800Total$794,300
Tax Record2024$17,816 ($1,485 / month)
Home Facts
Beds3Baths4.5Total Finished SqFt3,340 SqFtAbove Grade Finished SqFt3,340 SqFtStories2Lot Size40,075 SqFtStyleSingle Family ResidenceYear Built1828ZoningR-1CountyNEW HAVENAPNMADI M:37 B:2

Schools near 395 Boston Post Road

This home is within Madison School District.
Rating
School
Type
Grades
Distance
Kathleen H. Ryerson Elementary School
Public - K to 3
Walter C. Polson Upper Middle School
Public - 6 to 8
Daniel Hand High School
Public - 9 to 12
Dr. Robert H. Brown Middle School
Public - 4 to 5
Rating
School
Distance
Kathleen H. Ryerson Elementary School
PublicK to 3

Walter C. Polson Upper Middle School
Public6 to 8

Daniel Hand High School
Public9 to 12

Dr. Robert H. Brown Middle School
Public4 to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

Explore Nearby Homes

More information about 395 Boston Post Road, Madison, CT 06443

395 Boston Post Road is a single family home Coming Soon in Madison, CT 06443. This property is currently priced at $1,450,000. This listing's school district is Madison School District. Nearby schools include Kathleen H. Ryerson Elementary School, Walter C. Polson Upper Middle School and Daniel Hand High School. 395 Boston Post Road is a 4-bed, 5-bath, 3,779 sqft single family home built in 1828.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Laurie Mazzeo

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.