395 Boston Post Road, Madison, CT 06443
SOLD
MAY 1, 2026

$1,420,300

Trulia Estimate
  • 4 Beds
  • 5 Baths
  • 3,779 sqft (on 0.92 acres)

395 Boston Post Road, Madison, CT 06443

Madison Center
Est. Refi. Payment $10,110/mo*
Refinance Your Home
Currently Off Market - Sold May 1, 2026 for $1,400,000 (3% below list price)

Home Value

Trulia Estimate
$1.42M
Since last month
Increased$7K (+0.5%)
Since last year
Increased$67K (+5%)
Since last sale
Increased$20K (+1.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +85% in the last 10 years
MonthEstimated value
2026
August 2026$1.42M
August 2026$1.42M
July 2026$1.41M
June 2026$1.41M
May 2026$1.4M
April 2026$1.49M
March 2026$1.49M
February 2026$1.42M
January 2026$1.34M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
31 Stony Lane Lot 6 Road, Madison, CT
0.23
Single-Family Home
$2,001,250
01/28/26
4
3.5
3,400
31 Stony Lane Lot 3 Road, Madison, CT
0.27
Single-Family Home
$1,875,000
06/29/26
4
3.5
4,565
37 Lantern Hill Road, Madison, CT
0.30
Single-Family Home
$2,700,000
09/01/26
5
5.5
7,139
513 Boston Post Road, Madison, CT
0.48
Single-Family Home
$1,100,000
12/18/25
4
2.5
3,031
519 Boston Post Road, Madison, CT
0.51
Single-Family Home
$895,000
02/02/26
4
2.5
2,691
43 Burcam Drive, Madison, CT
0.38
Single-Family Home
$941,000
10/01/25
3
3
2,393
55 Island Avenue, Madison, CT
0.86
Single-Family Home
$1,400,000
07/17/26
4
3
3,046
584 Boston Post Road, Madison, CT
0.80
Single-Family Home
$1,525,000
10/01/25
5
5.5
6,278
24 Cherry Lane, Madison, CT
0.46
Single-Family Home
$1,186,900
05/08/26
3
2.5
1,712

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
374 Boston Post Road, Madison, CT 06443
0.11
$1,525,800
5
3.5
3,060
Off Market
31 Stony Lane Lot 6 Road, Madison, CT 06443
0.23
$2,001,250
4
3.5
3,400
Recently Sold
27 Sterling Park, Madison, CT 06443
0.23
$937,100
3
2.5
2,458
Off Market
348 Boston Post Road, Madison, CT 06443
0.23
$1,679,900
3
2.5
2,100
Off Market
30 Overlook Drive, Madison, CT 06443
0.22
$1,242,000
4
2.5
2,855
Off Market
31 Stony Lane Lot 3 Road, Madison, CT 06443
0.27
$1,875,000
4
3.5
4,565
Recently Sold
33 Overlook Drive, Madison, CT 06443
0.25
$1,825,000
6
4.5
4,903
Off Market
37 Lantern Hill, Madison, CT 06443
0.29
$2,102,800
4
4.5
5,400
Off Market
23 Lantern Hill, Madison, CT 06443
0.30
-
-
-
-
Off Market
37 Lantern Hill Road, Madison, CT 06443
0.30
$2,700,000
5
5.5
7,139
Recently Sold
26 Rockledge Drive, Madison, CT 06443
0.30
$1,216,500
4
2.5
2,786
Off Market

Local Information

  • Map ViewExplore the area around 395 Boston Post Road.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1828
0.92 acre lot
3,779 sqft
$370/sqft
Garage

About this House

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. Wide original floorboards run throughout much of the home, while abundant windows fill the rooms with beautiful natural light. The interior offers a flexible layout, including a first-floor office and the beautiful new full bath that allows for a convenient guest suite or potential fourth bedroom. The bright, updated eat-in kitchen includes granite counters, an island, double ovens, a large pantry and heated tile flooring. French doors open to the home's newest and most spectacular addition: the wraparound screened porch designed for relaxed shoreline living. This inviting space is perfect for summer dining, morning coffee, or evening gatherings while enjoying views of the beautiful grounds. The property itself is nothing short of enchanting. Mature landscaping and established gardens create a private and colorful setting that changes with the seasons. In bloom, the grounds overflow with peonies and daffodils, while morning glories, an arbor of wisteria, graceful Japanese maples, and a magnificent magnolia tree add layers of beauty and character to the landscape. A detached two-car garage with a studio above includes a full bath, offering wonderful flexibility for guests, a home office, gym, or creative space. An outdoor shower adds a classic shoreline touch after a day at the nearby beach, walking distance away. Ideally located, the home is just a short walk or bike ride to the historic Madison Green, where residents gather for summer concerts, weekend antique shows, and the popular Friday farmer's market. Madison's beautiful beaches, charming shops, restaurants, and coastal attractions are all close by. Rich in history, filled with light, and surrounded by beautiful gardens, the Ebenezer Dudley Home offers a rare opportunity to own a piece of Madison's past while enjoying the comfort and lifestyle of shoreline living today. A truly special property ideal as a full-time residence or a cherished coastal retreat.
395 Boston Post Road, Madison, CT 06443 is a 4 bedroom, 5 bathroom, 3,779 sqft single-family home in Madison Center, built in 1828. It last sold for $1,400,000 on May 1, 2026 (3% below the $1,450,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,420,300, with a rent estimate of $6,685/month.
Last check for updates: about 11 hours ago
Listed by Laurie Mazzeo, (203) 641-6837
William Pitt Sotheby's Int'l, (203) 245-6700
Bought with: Steven D. Elek, (203) 843-6767, RE/MAX Heritage, (203) 646-2380
Source: Smart MLS, MLS#24158296

Home Details for 395 Boston Post Road

Interior Features

Interior Details
Basement: Partial,UnfinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Studio Apt
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 5
Dimensions and Layout
Living Area: 3779 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Electric Cooktop, Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Gas Water Heater, Tankless Water HeaterDishwasherDryerLaundry: Upper LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,Gas In StreetHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Wrap Around, Screened, Porch, PatioFencing: Wood, PartialOther Structures: Shed(s)Exterior: Stone WallFoundation: Concrete Perimeter, StoneNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 5Parking: Detached,Paved,Driveway,Garage Door Opener,Private,Asphalt
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 3779 Square Feet

Property Information

Year Built
Year Built: 1828
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Clapboard, Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1155692

Price & Status

Price
List Price: $1,450,000Price Per Sqft: $370/sqft
Status Change & Dates
Off Market Date: Mon Mar 30 2026Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Madison
School Information
Elementary School: Neck RiverJr High / Middle School: Per Board of EdHigh School: Daniel Hand

Building

Building Area
Building Area: 3779 Square Feet

Community

Community Features: Golf, Health Club, Library, Medical Facilities, Private School(s), Public Rec Facilities, Shopping/Mall, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 0.92 acres

Miscellaneous

BasementMls Number: 24158296Attic: Pull Down StairsAttribution Contact: (203) 641-6837Above Grade Unfinished Area: 3779Activation Date: Sun Mar 29 2026

Additional Information

GolfHealth ClubLibraryMedical FacilitiesPrivate School(s)Public Rec FacilitiesShopping/MallTennis Court(s)

Price and Tax history

DateEventPrice
May 1, 2026
Source: Smart MLS #24158296
Sold
$1,400,000
Apr 6, 2026
Source: Smart MLS #24158296
Pending
$1,450,000
Mar 29, 2026
Source: Smart MLS #24158296
Listed For Sale
$1,450,000
Feb 25, 2021
Source: Smart MLS #170300921
Sold
$703,000
Dec 6, 2020
Source: Agent Provided
Pending
$745,000

Market trends in Madison

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$716K
$6.67KMoM
Sale-to-List Price
101.8%
0.2%MoM
Price per sq ft
$337
$3MoM
Available listings
59
4MoM

Around this home

Neighborhood Overview

Madison Center
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Madison Center

At least 1 Trulia users voted on each feature.

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's walkable to restaurants

  • 100 % Say it's dog friendly

  • 100 % Say there's wildlife

  • 100 % Say neighbors are friendly

  • 50 % Say there are community events

  • 50 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Nancy Bussiere
    "My commute to work is under 15mins. I love the easy access to highways. There is public transportation available but I haven’t used it as of yet"
    0
    Flag

LGBTQ Local Legal Protections

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 395 Boston Post Road

  • What is 395 Boston Post Road estimated to be worth?
    Trulia's estimated value for 395 Boston Post Road in Madison, CT is $1,420,300.
  • What is the price history for 395 Boston Post Road?
    395 Boston Post Road in Madison, CT last sold for $1,400,000 in May 2026.
  • Is Madison a buyer's or seller's market?
    Madison is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Madison?
    The median sale price in Madison is $716K. That is up $6.67K from the prior month.
  • Does 395 Boston Post Road have air conditioning?
    Yes, 395 Boston Post Road in Madison, CT has air conditioning.
  • Does 395 Boston Post Road have laundry facilities?
    Yes, 395 Boston Post Road in Madison, CT has in-unit laundry.

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