566 Boston Post Rd, Madison, CT 06443
Property image
Property image
OFF MARKET

$1,250,800

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 2,241 sqft (on 1.30 acres)

566 Boston Post Rd, Madison, CT 06443

Madison Center
Est. Refi. Payment $8,739/mo*
Refinance Your Home
Currently Off Market - Sold Feb 12, 2016 for $615,000

Home Value

Trulia Estimate
$1.25M
Since last month
Increased$81K (+6.9%)
Since last year
Increased$46K (+3.8%)
Since last sale
Increased$636K (+103.4%)
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 +105% in the last 10 years
MonthEstimated value
2026
August 2026$1.25M
August 2026$1.25M
July 2026$1.17M
June 2026$1.35M
May 2026$1.24M
April 2026$1.23M
March 2026$1.18M
February 2026$1.2M
January 2026$1.19M
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
52 Copse Road, Madison, CT
0.30
Single-Family Home
$799,000
11/25/25
3
1
1,382
519 Boston Post Road, Madison, CT
0.21
Single-Family Home
$895,000
02/02/26
4
2.5
2,691
43 Burcam Drive, Madison, CT
0.48
Single-Family Home
$941,000
10/01/25
3
3
2,393
55 Island Avenue, Madison, CT
0.23
Single-Family Home
$1,400,000
07/17/26
4
3
3,046
43 Fort Path Road, Madison, CT
0.57
Single-Family Home
$503,000
01/30/26
3
1.5
1,346
513 Boston Post Road, Madison, CT
0.24
Single-Family Home
$1,100,000
12/18/25
4
2.5
3,031
162 Yankee Peddler Path, Madison, CT
0.59
Single-Family Home
$580,000
04/30/26
3
2.5
1,300
58 Railroad Avenue, Madison, CT
0.79
Single-Family Home
$420,000
12/02/25
4
1
1,253
40 Puritan Lane, Madison, CT
0.77
Single-Family Home
$625,000
03/02/26
4
3.5
2,656
24 Cherry Lane, Madison, CT
0.34
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
584 Boston Post Road, Madison, CT 06443
0.09
$1,585,600
5
5.5
6,278
Off Market
45 Island Avenue, Madison, CT 06443
0.19
$3,495,000
5
5
5,657
For Sale
30 Meeting House Lane, Madison, CT 06443
0.17
$1,695,000
5
3.5
3,912
For Sale
55 Island Avenue, Madison, CT 06443
0.23
$1,400,000
4
3
3,046
Recently Sold
519 Boston Post Road, Madison, CT 06443
0.21
$895,000
4
2.5
2,691
Recently Sold
513 Boston Post Road, Madison, CT 06443
0.24
$1,100,000
4
2.5
3,031
Recently Sold
37 Copse Road, Madison, CT 06443
0.24
$852,100
3
2.5
2,241
Off Market
34 Windward Lane, Madison, CT 06443
0.27
$1,913,600
3
2.5
2,756
Off Market
57 Island Avenue, Madison, CT 06443
0.28
$1,660,700
4
3.5
3,006
Off Market
4 Cambridge Drive #4, Madison, CT 06443
0.29
$1,055,600
2
2.5
2,358
Off Market
6 Cambridge Drive #6, Madison, CT 06443
0.31
$965,200
2
2.5
2,258
Off Market
24 Windward Lane, Madison, CT 06443
0.32
$1,785,400
3
3.5
3,628
Off Market

Local Information

  • Map ViewExplore the area around 566 Boston Post Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1675
Lot Size
1.3 acres
Living Area
2,241 sqft
Price/Sqft
$558
Parking
Garage

About this House

General George Washington was served lunch here! Long believed to be the oldest home in Madison (c.1675) recent research reveals the possibility of a slightly later birthdate, (c.1720). Add your own history to this fascinating landmark property across from the Town Green on this LARGE, 1.3 acre site. A perfect example of the Colonial saltbox style this home has been featured in many books & articles on period homes. A true piece of New England history yet very warm & liveable. When the locally prominent Dudley family owned the property they entertained George Washington. That was the Spring of 1776 -the home was operated as a tavern and reputedly offered the best food in then "East Guilford". For the purist, there is plenty to love. For modern use, the house is remarkably comfortable and easily adapts to improvements and updates. Original fireplaces, corner cupboards, wide plank floors, paneling, beams, and hand wrought hardware are just some of the original touches lovingly respected and preserved down through the generations. This is the beautiful white, wood roofed house with the charming decorative fence that defines the south side of Route One, bordered by picturesque Island Avenue. Be a part of the New England village experience-the 4th of July parade route will come just by your front gate, and you are only steps to all that downtown has to offer. Find yourself walking to everything, including LI Sound!
566 Boston Post Rd, Madison, CT 06443 is a 3 bedroom, 1 bathroom, 2,241 sqft single-family home in Madison Center, built in 1675. It last sold for $615,000 on Feb 12, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,250,800, with a rent estimate of $3,551/month.

Home Details for 566 Boston Post Rd

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Interior Details
Number of Rooms: 7Types of Rooms: Dining Room
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: OtherExterior: WoodGarden
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1675
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1.30 acres

Price and Tax history

DateEventPrice
Feb 12, 2016
Source: Smart MLS #N10020145
Sold
$615,000
Dec 16, 2015
Source: Agent Provided
Pending
$689,000
Jul 2, 2015
Source: Agent Provided
PriceChange
$689,000
Price decreased by 5%
Feb 12, 2015
Source: Agent Provided
Listed For Sale
$729,000
Oct 15, 2014
Source: Agent Provided
ListingRemoved
$750,000

Market trends in Madison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$710K
$53.67KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$334
$7MoM
Available listings
63
8MoM

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

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Frequently asked questions about 566 Boston Post Rd

  • What is 566 Boston Post Rd estimated to be worth?
    Trulia's estimated value for 566 Boston Post Rd in Madison, CT is $1,250,800.
  • What is the price history for 566 Boston Post Rd?
    566 Boston Post Rd in Madison, CT last sold for $615,000 in February 2016.
  • 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 $710K. That is down $53.67K from the prior month.
  • How big is the lot at 566 Boston Post Rd?
    The lot at 566 Boston Post Rd in Madison, CT is about 1.3 acres.
  • Does 566 Boston Post Rd have a garage?
    Yes, 566 Boston Post Rd in Madison, CT has a garage.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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