Skip main navigation
Off market
  • $1,225,500

    566 Boston Post Rd, Madison, CT 06443

    3beds
    2,241sqft
    SingleFamily
    Built in 1675
    1.3 Acres Lot
    $1,225,500 Zestimate®
    $547/sqft
    $2,897 Estimated rent

    Home value

    $1,225,500

    $1.09M - $1.38M

    $2,897/mo

    Zestimate® history
    Loading...

    Owner options

    List your home for rent

    $2,897/mo

    Rent Zestimate®

    Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.

    Learn more

    $2,897/mo

    Rent Zestimate®

    Refinance and save

    $8,753/mo

    Est. payment

    Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.

    See today's rates

    $8,753/mo

    Est. payment

    Explore your selling options

    Work with a Zillow partner agent

    Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.

    Get started

    List with your own agent

    Get your home in front of millions of buyers by listing it on Zillow.

    Learn how to do it

    Sell it yourself

    Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).

    List your home

    What's special

    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!

    This property is off market, which means it's not currently listed for sale or rent on Zillow. This may be different from what's available on other websites or public sources.

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 1
    • Full bathrooms: 1
    Heating
    • Other, Oil
    Appliances
    • Included: Dishwasher, Range / Oven, Refrigerator
    Features
    • Flooring: Hardwood
    • Has fireplace: Yes
    Interior area
    • Total interior livable area: 2,241 sqft

    Property

    Parking
    • Parking features: Garage - Detached
    Features
    • Exterior features: Wood
    Lot
    • Size: 1.30 Acres
    Details
    • Parcel number: MADIM38B127

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Colonial
    Materials
    • Roof: Other
    Condition
    • Year built: 1675

    Community & neighborhood

    Location
    • Region: Madison

    Price history

    DateEventPrice
    2/12/2016Sold$615,000-10.7%$274/sqft
    Source: Smart MLS #N10020145 Report a problem
    12/16/2015Pending sale$689,000$307/sqft
    Source: William Pitt and Julia B. Fee Sotheby's International Realty #N10020145 Report a problem
    7/2/2015Price change$689,000-5.5%$307/sqft
    Source: William Pitt and Julia B. Fee Sotheby's International Realty #N10020145 Report a problem
    2/12/2015Listed for sale$729,000-2.8%$325/sqft
    Source: William Pitt Sotheby's Int'l #N10020145 Report a problem
    10/15/2014Listing removed$750,000$335/sqft
    Source: Berkshire Hathaway HomeServices New England Properties #M9145947 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$16,605 +2%$740,300
    2024$16,287 +17.7%$740,300 +60.3%
    2023$13,840 +1.9%$461,800

    Find assessor info on the county website

    Neighborhood: Madison Center

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Island Avenue
    • Middle: brown
    • High: Daniel Hand

    Source: The MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

    Get pre-qualified for a loan
    At Zillow Home Loans, we can pre-qualify you in as little as 5 minutes with no impact to your credit score.

    An equal housing lender. NMLS #10287.

    Sell for more on Zillow
    Get a free Zillow Showcase℠ listing and you could sell for .
    $1,225,500
    2% more+ $24,510
    With Zillow Showcase(estimated)
    $1,250,010