North of Robert Ober's home stood Rolling Ridge, a wealthy merchant's one-and-a-half-story brick Georgian-style residence approached by a long tree-lined drive. This Tidewater architectural style is rarely found in Montgomery County, and the house featured a five-bay facade, paired gable-end chimneys, a broad sloping roof, and four chimneys serving ten fireplaces. Rolling Ridge was perhaps one of the earliest farming operations in Laytonsville, an area of fertile, well-drained soil. The farmstead continued under the later ownership of the Warfield, Christopher, Small, and Jones families, and its once-significant formal landscape elements are attributed to landscape architect John H. Small III.