Hampton, Virginia
Average home price: $253,911
Sandwiched between the Chesapeake Bay and Hampton Roads Harbor, this coastal Virginia hideaway is bursting with history. Not only was it the first continuously English-speaking settlement in the State (yes, that amount of history), it also gave rise to the country’s first-ever free public education system, and served as the training ground for NASA’s very first astronauts. That, plus local monument Fort Monroe played a huge role in the Civil War. Thousands of formerly enslaved peoples sought refuge there after Major General Benjamin Butler’s 1861 ruling that they were “contraband of war” and thus couldn’t be sent back, kicking off the first step on the road to emancipation. Later, Confederate president Jefferson Davis was imprisoned inside the same fort—dubbed Freedom’s Fortress—after his 1865 capture. You can learn all about both turning points at the Casemate Museum at Fort Monroe National Monument.
But, of course, the beach. It’s swell, with sandy public access points scattered along the sloping Chesapeake and culminating in the pristine Grandview Nature Reserve to the north. Between exploring the harbor on the 65-foot Miss Hampton II, fishing off the Downtown Hampton Public Pier, and lazy waterfront hangs, you can take advantage of award-winning programming at the Virginia Air & Space Center, Hampton History Museum, Hampton Coliseum (home to the annual Hampton Jazz Festival), Langley Speedway, and more. Come for the culture, stay for the vibes (and the refreshingly affordable real estate).