6. 158 Montgomery Street (Newburgh)

What to know:
Circa 1870
Address: 158 Montgomery Street, Newburgh, New York, 12550
Price: $399,000
Style: Queen Anne

The Stockbridge Ramsdell House, located in the Newburgh’s historic district, was once the family home of Homer Stockbridge Ramsdell, the president of the Erie Railroad. Today, it overlooks the Hudson River, operating as a bed & breakfast. Newburg itself is frequently the subject of urban design and architecture classes at Columbia University, which is usually the sign of a city or neighborhood on the cusp of attracting hefty attention from real estate folks.