566 Boston Post Rd
Madison, CT 06443
Madison Center
3 Beds
1 Bath
2,241 sqft (on 1.30 acres)
3 Beds
1 Bath
2,241 sqft
(on 1.30 acres)
Local Information
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Description
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 Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 566 Boston Post Rd
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Heating & Cooling Heating: Other, OilAir ConditioningHeating Fuel: Other |
Interior Details Number of Rooms: 7Types of Rooms: Dining Room |
Appliances & Utilities DishwasherRefrigerator |
Fireplace & Spa Fireplace |
Levels, Entrance, & Accessibility Floors: Hardwood |
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Exterior Home Features Roof: OtherExterior: WoodGarden |
Parking & Garage GarageParking: Garage Detached |
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Year Built Year Built: 1675 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Lot Area: 1.30 acres |
Price History for 566 Boston Post Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 02/12/2016 | $615,000 | Sold | Smart MLS #N10020145 |
| 12/16/2015 | $689,000 | Pending | Agent Provided |
| 07/02/2015 | $689,000 | PriceChange | Agent Provided |
| 02/12/2015 | $729,000 | Listed For Sale | Agent Provided |
| 10/15/2014 | $750,000 | ListingRemoved | Agent Provided |
| 03/11/2014 | $750,000 | Listed For Sale | Agent Provided |
Market trends in Madison
Last updated April 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
73 19MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $16,605 |
| Assessment | $740,300 |
Home facts updated by county records
Comparable Sales for 566 Boston Post Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.30 | Single-Family Home | $799,000 | 11/25/25 | 3 | 1 | 1,382 | |
0.21 | Single-Family Home | $895,000 | 02/02/26 | 4 | 2.5 | 2,691 | |
0.48 | Single-Family Home | $941,000 | 10/01/25 | 3 | 3 | 2,393 | |
0.74 | Single-Family Home | $505,000 | 06/12/25 | 3 | 1 | 1,196 | |
0.57 | Single-Family Home | $503,000 | 01/30/26 | 3 | 1.5 | 1,346 | |
0.24 | Single-Family Home | $1,100,000 | 12/18/25 | 4 | 2.5 | 3,031 | |
0.40 | Single-Family Home | $1,225,000 | 06/19/25 | 4 | 3 | 2,340 | |
0.59 | Single-Family Home | $580,000 | 04/30/26 | 3 | 2.5 | 1,300 | |
0.79 | Single-Family Home | $420,000 | 12/02/25 | 4 | 1 | 1,253 | |
0.49 | Single-Family Home | $475,000 | 07/07/25 | 3 | 2 | 1,125 |
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Assigned Schools
These are the assigned schools for 566 Boston Post Rd.
- J. Milton Jeffrey Elementary School
- K-3
- Public
- 362 Students
10/10GreatSchools RatingParent Rating AverageExcellent. Jeffrey school IS the place to be!Parent Review8y ago - Daniel Hand High School
- 9-12
- Public
- 828 Students
10/10GreatSchools RatingParent Rating AverageI feel very unsafe when in the presence of many school administrators. I wouldn’t wish the experience I’ve had here on my worst enemy. I feel constantly harassed by some teachers but more namely the school administrators, including the Vice principal. Every day I try to come in with a positive attitude about this place, but someone has to ruin it. There are however some teachers that do a great job teaching and making everyone feel safe, but the negatives outweigh this way too much.Student Review1y ago - Dr. Robert H. Brown Middle School
- 4-5
- Public
- 354 Students
9/10GreatSchools RatingParent Rating AverageThe school is great. The teachers help you as much as they can and they want you to have as much fun as possible. At the end of every trimester some related arts classes let parents come to the school to watch there kid (in Xylorythems, Theater arts, Music and Art.) There is some bullying but you can quicky report if someone is bullying you and they will quickly handle it.Student Review2y ago - Walter C. Polson Upper Middle School
- 6-8
- Public
- 520 Students
9/10GreatSchools RatingParent Rating AverageMy kids are currently attending Polson MS and are receiving an excellent education that is preparing them for high school and beyond. The course work is challenging and homework is not lacking, however, the teachers are readily available to the students for extra help before and after school. But even with all the hard work the school has great spirit and the kids have fun either in sports, theater, music or what ever their area of interest is. The schools drew us to Madison and the location has kept us! GREAT TOWN! I believe the parent involvement in the school system is a primary driver for why the school system is so successful.Parent Review14y ago 
Check out schools near 566 Boston Post Rd.
Neighborhood Overview
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.
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566 Boston Post Rd, Madison, CT 06443 is a 3 bedroom, 1 bathroom, 2,241 sqft single-family home built in 1675. 566 Boston Post Rd is located in Madison Center, Madison. This property is not currently available for sale. 566 Boston Post Rd was last sold on Feb 12, 2016 for $615,000. The current Trulia Estimate for 566 Boston Post Rd is $1,308,400.