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!
Off market
$1,269,800
566 Boston Post Rd, Madison, CT 06443
3beds
2,241sqft
SingleFamily
Built in 1675
1.3 Acres Lot
$1,269,800 Zestimate®
$567/sqft
$3,253 Estimated rent
What's special
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
Services availability

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