Simon Wilmer was the first owner of Water Lot No.8 In the early days of Chestertown. the house was center-hall, 2 story building and ONE room deep This is important because in about 1764 William Ringgold bought the property for 600 pounds.  It was he who doubled the size to a TWO rooms DEEP house. Unusual because we think of additions being made in 18th. by adding wings to either side. 
Ringgold also filled in a cove shown on an early town plat and terraced the entire yard down to the Chester River. This is the only known instance of terracing or falles, in Chestertown.  
Ringgold was a member of the Committee of Safety during the Revolutionary War and also a member of the convention who drafted Maryland's constitution in 1776. This was the beginning of a long important history contributing to Chestertown's distinguished designation as a National Historic Landmark. Chestertown's Historic District is on the National Register of Historic Places.

SMITH-RINGGOLD HOUSE. 
This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort. Originally a merchant’s home in the heart of historic Chestertown, the Smith-Ringgold house has been modified representing four defined periods and enlarged over the course of its 250-year history. The present owner took two years to restore the home’s structural integrity from the foundation to the attic, adding a river-side addition and porch, replacing the cedar shingle roof, and completely redoing the plumbing, wiring, heat and A/C systems. The wood floors throughout the house have been beautifully restored.  Modern storm windows are energy efficient and all but eliminate street noise. Aside from your own personal touches, this house is move-in-ready.

The ground floor has a large double parlor, cozy sitting room, formal dining room, breakfast room, and a stunning chef’s kitchen.  An important feature is the hand painted dining room mural by noted artist Jack Schroeder. The front hall, redesigned in about 1860, replaced a steep stairway with a grand and gracefully curving staircase. The second floor contains three large en-suite bedrooms and a laundry room that is also accessible from the kitchen via a “secret” staff stairway. The third floor has a large sitting room, bathroom, and bedroom, with part of the home’s original c. 1759 roof forming a unique design element. The backyard was extensively terraced, probably in the late 1700s, in descending levels down to the Chester River. The free-standing brick garage dates from the early 20th century, when car garages replaced horse barns. This structure could easily be repurposed as an artist’s studio or home workshop. A wide driveway area provides additional off-street parking.

Truly an inviting residence for intimate family evenings or grand parties. Perfect setting for one's collection of antiques or for the simplicity of contemporary furniture which emphasizes the wonderful architecture.

CHESTERTOWN IN THE COUNTY OF KENT

Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities.  Chestertown is home to a surprisingly large number of elegant, historical Georgian homes as well as Victorian “painted ladies.” With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City. 

Centrally located Washington College (founded in 1782 with the personal support of George Washington) provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers.  The town boasts a weekly Farmers Market, excellent coffee bars, restaurants, and art galleries—but no big box stores. The Chester River Yacht & Country Club offers an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party, commemorating a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. Today Chestertown is a vibrant mix of old families, newcomers, college students, full time residents with children, and involved weekenders.  

Truly an inviting residence for intimate family evenings or grand parties. Perfect setting for one's collection of antiques or for the simplicity of contemporary furniture which emphasizes the wonderful architecture.

CHESTERTOWN IN THE COUNTY OF KENT

Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities.  Chestertown is home to a surprisingly large number of elegant, historical Georgian homes as well as Victorian “painted ladies.” With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City. 

Centrally located Washington College (founded in 1782 with the personal support of George Washington) provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers.  The town boasts a weekly Farmers Market, excellent coffee bars, restaurants, and art galleries—but no big box stores. The Chester River Yacht & Country Club offers an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party, commemorating a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. Today Chestertown is a vibrant mix of old families, newcomers, college students, full time residents with children, and involved weekenders.