The Your
Sep 01, 2026
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Historic Tulip Forest Estate in Chestertown Offers 1,045 Acres for $38 Million

Chestertown, MD – A piece of American history is on the market. Tulip Forest Estate, also known as Caulk’s Field, sits on 1,045 acres west of the town in Kent County and is listed for $38.2 million. The main house, built in 1743, showcases classic Flemish bond brickwork with glazed headers that form a basket‑weave pattern, and the year of construction is inlaid in the masonry.

Historic features and original details

The 4‑bedroom, 3‑bath, 2,330‑square‑foot residence retains many of its original elements, including secret staircases, wood‑panelled rooms, and walls over 12 inches thick. Two additional structures extend from the original footprint, and a caretaker’s house, two other residences, numerous out‑buildings and barns complete the property.

Land composition and conservation

Of the total acreage, 680 acres remain active farmland, 272 acres are timberland, and 27 acres of wetlands are currently being restored. A 45‑acre parcel participates in a crop‑replacement program that removes the land from production and replaces it with conservation cover crops. The estate also includes five ponds, nearly four miles of internal roads, and seven acres zoned for commercial use, offering modest development potential along the main road.

Recreational and hunting opportunities

The property’s abundant wildlife supports waterfowl and upland game hunting, a long‑standing tradition on Maryland’s Upper Eastern Shore. Families can enjoy private hunting experiences while preserving the natural habitat.

Historical significance

A monument on the grounds commemorates the Battle of Caulk’s Field, a 1814 engagement that occurred after the British burned Washington, D.C. and before the attack on Fort McHenry. According to Kent County records, roughly 140 Royal Marines and sailors under Captain Sir Peter Parker were repelled by local militia led by Lt. Col. Philip Reed. The militia’s riflemen drew the British into an ambush, and artillery fire forced the invaders to retreat after Parker was mortally wounded. The battle remains a point of local pride and a reminder of the area’s role in the War of 1812.

Location and community ties

Located about a mile from the Eastern Shore of the Chesapeake Bay and near Fairlee Creek and Tolchester, the estate is conveniently close to Washington College, making it an attractive option for families seeking both educational resources and a historic setting.

Potential uses

Beyond its historic charm, Tulip Forest offers a working farm, timber production, conservation opportunities, and limited commercial development. The blend of heritage, natural resources, and flexible land use makes it a unique acquisition for those who value tradition, family stewardship, and the freedoms afforded by private property ownership.

Interested buyers can view the full listing and additional photographs through the provided real‑estate link.


Original reporting: Baltimore Fishbowl — read the source article.

OBBM Network Editorial Staff

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Editorial team behind OBBM Network — independent, hyper-local journalism syndicated through HyperLocalLoop and OBBM Network TV.

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