8184 Rock Hall Road, Chestertown.
Hot House: Become the Next Steward of Tulip Forest Estate in Chestertown. 4 Beds/3 Baths. 2,330 Square Feet. $38.2M
What: Caulk’s Field, the main house at Tulip Forest was built in 1743, and the surrounding 1,000(!) acres played a role in the war of 1812. This historic brick house, built in the Flemish bond pattern with glazed headers that make it look like basketweave, has the date of its origin inlaid into the bricks.

The interior of the house retains much of its original details, including secret staircases, wood-paneled rooms, 12+ inch thick walls, and two additional buildings telescoping out from the original. In addition, there is a care-takers house on the property, as well as two other residences, numerous out-buildings and barns.

The remarkable thing about this property is that its 1,045 acres have been intact for generations. Out of the acreage, 680 are farmland, 272 are timberland, and 27 are wetlands that are currently being restored. There are 45 acres in a crop replacement program, taking the land out of farming and replacing it with land conservation cover crops. Additionally, there are five ponds and almost four miles of internal roads. Seven acres are zoned for commercial purposes, and there is room for small development opportunities along the main road.

The property can also be used for hunting, with the ample wildlife and waterfowl hunting that the has made the Upper Eastern Shore famous.
There is a monument to the Battle of Caulk’s Field on the property, along the main road. The Battle took place after the British had burned Washington, D.C. but before they launched the attack on Fort McHenry.
From Kent County’s website: A contingent of around 140 Royal Marines and sailors, led by Captain Sir Peter Parker, launched a surprise raid inland—only to be met by well-positioned local militia under Lt. Col. Philip Reed. The clash was intense and strategically fought, with militia riflemen drawing the British into an ambush before artillery opened fire, ultimately forcing the invaders to retreat after Parker was mortally wounded.
Though often overshadowed by larger battles, Caulk’s Field became a rare American victory during a campaign marked by British dominance. The engagement not only boosted local morale following the burning of Washington, D.C., but also left a legacy preserved in surviving battlefields and historic markers.

Where: Tulip Forest is located west of Chestertown in Kent County. It’s about a mile from the Eastern Shore of the Chesapeake, and close to Fairlee Creek and Tolchester. It’s perfect if you have children at Washington College.

Final Appraisal: It you are looking for a working farm, full of the historical aspects of the Upper Eastern Shore, private hunting property and loads of land, Tulip Forest would be a great place for you. The listing for the house is here.
All photographs from the listing.
