LHD boundaries as described are approximate and subject to change. Consult the LHD Study Report on file with the relevant local district commission or municipal authority to verify district boundaries and whether a specific property, particularly one in proximity of a boundary line, is within the district. Also note that LHD boundaries may differ from those of State or National Register Districts.
The district includes the Green, the former town hall, a school, an historic house museum, two churches and twenty-three houses.
Colonial, Classical Revival, Federal, Greek Revival, Italianate, Queen Anne.
Madison historic district is located along the Boston Post Road in the area flanking the town's Green. It includes the traditional center of the town and the properties along the roads that form the northern, southern, eastern and western borders of the Green. The story of Madison's historic district before the town was established and the Green was laid out. Madison began as part of the town of Guilford, which was settled by a group of colonists under the leadership of the Reverend Henry Whitfield in 1639. Guilford was enlarged to the east twice in its early years. In 1641 it grew through the purchase of land, much of which is the western part of modern-day Madison, from the local Native Americans. Then in 1650 it was expanded again, this time by the gift of land from George Fenwick of the neighboring community of Saybrook. This land makes up the eastern half of the town. While little remains from the earliest days of Madison, the historic district does include a house from this era, the c. 1675 Grave house at 581 Boston Post Road. 
For more than three centuries, The Green has been the center of the community life in the town of Madison. It dates from the earliest days of the community when it was used as common pasture and the site for the first meetinghouse. While the geographic center of the population, the economic center of the community, and the civic center of the town have all moved away from the Green, it retains a symbolic place in the heart of the community. The Green and the buildings that surround it have the added value of providing a visible reminder of the growth of the community, as the District contains representatives of many of the architectural styles employed through out the town. These examples are especially powerful sine many of them retain significant architectural integrity. The buildings in the district represent many of the architectural styles that have been popular since the community was settled. From the earliest houses in the area to its most recent buildings, the district serves as a catalogue of the community's architectural trends. The Green remains the focal point of the residential neighborhood that developed around it and continues to be the civic and religious center of town. Its broad expanse is still used as a public gathering place for community events. [2 & 3]
 District information retrieved from the town website http://www.madisonct.org/. Madison Historic District, Report of the Historic District Study Committee, 2006, SHPO Library, Hartford.  Significance of the Green adopted from the website www.towngreens.com. Assessors information and Parcel IDs retrieved from the study committee report .