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- From the antebellum mansions of Natchez, Mississippi, to the battlefields of Gettysburg, Pennsylvania, these five cities surround you with history.
- Each destination has a deep cultural heritage as well as below-average costs of living, making them suitable for retirees and history lovers alike.
While tourist accommodations in cities like Boston command high prices due to their colonial charm, dozens of other American places offer equally compelling heritage, such as Revolutionary War battlefields, Spanish missions, and antebellum architecture, all for a fraction of the cost.
Using the Zillow Home Value Index and cost of living data from the Institute for Economic Research, we found five places where you can walk cobblestone streets, tour centuries-old landmarks, and live inside an American story without breaking your retirement budget.
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Natchez, Mississippi
After walking in Natchez in 1852, the famous landscape architect Frederick Law Olmsted suggested that the geometry of “a sudden precipice above the river, with a public park upon it…on the edge of an immense precipice” could not be improved upon. Look out from Natchez Bluff just before dusk, with its shield of purple and orange across the horizon, and you’d have to agree. At approximately 200 feet above the water, the view stretches for miles in both directions, with riverboats drifting by year-round.
In the decades before the Civil War, Natchez had the largest number of millionaires per capita in the United States When Natchez surrendered to Union forces in 1862, its mansions were saved, meaning Natchez can now claim more antebellum mansions than anywhere else in the South, as well as more than 1,000 buildings on the National Register of Historic Places.
At $115,132, Natchez has the most affordable median home value on our list. It is located in a county with the lowest median housing value among attractive American retirement locations that provide affordable housing. This affordability reflects the low cost of living in Natchez, which is 21% lower than the national average. Mississippi also doesn’t tax Social Security or retirement income, saving you even more.
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San Antonio, Texas
The skyscrapers of downtown San Antonio surround the Alamo, the famous site where Davy Crockett and hundreds of others died defending the fort. Walk south from the Alamo along the river, and you’ll pass four other missions that together make up a UNESCO World Heritage Site.
Mission San Jose, dubbed the “Queen of Missions,” is the largest, with Texas limestone walls and elaborate Spanish Colonial architecture. The history of these missions is not over: all four churches are active Catholic parishes, and parishioners are known for their volunteer work along the U.S.-Mexico border.
In downtown, the River Walk runs through town 20 feet below street level, an urban waterway lined with cypress trees, restaurants, bars, and live music venues. There are festivals throughout the year, such as Fiesta San Antonio in April and Dead River Parade Day in the fall.
At approximately $247,152, the median home value in San Antonio is well below the national average of $360,7273, and the cost of living is 6% lower than the national average. Texas has no state income taxes, giving you more for your buck for the fresh Mexican cuisine served along the Riverwalk.
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Located on the Gulf Coast, Pensacola features 8.5 miles of white-sand beaches just minutes from downtown.
Pensacola, Florida
The oldest European settlement in the United States, Pensacola is where Spanish explorer Tristan de Luna arrived in 1559 with 11 ships from Veracruz, Mexico. The Luna settlement precedes St. Augustine by six years and Jamestown by 48 years.
Pensacola later became a strategic military location whose ownership passed to the United Kingdom, Spain, France, and the United States History still exists in these parts: Archaeologists from the University of West Florida excavated the original Luna settlement site in 2015, discovering 16th-century Spanish ceramics, glass trade beads, and wrought iron nails in a residential neighborhood.
Downtown Pensacola’s Historic District, centered around Plaza Seville and Plaza Ferdinand VII (the original British parade ground), spans eight and a half acres and includes 28 historic buildings. Spanish Colonial architecture lines the brick piers, while the 1907 Pensacola History Museum occupies a Mediterranean-style building with a red-tile roof and an arched entry porch.
At $259,932, Pensacola’s median home value is slightly higher than San Antonio but well below popular southern Florida coastal cities like Boca Raton. The cost of living is 11% lower than the national average, and Florida’s lack of a state income tax makes the deal even better.
Savannah, Georgia
In 1733, General James Oglethorpe designed Savannah City around a grid of squares, park-like open spaces surrounded by residential and civic buildings in repeating “wings.” Twenty-two squares remain today, shaded by live oaks covered in Spanish moss. Johnson Square was the first and remains the largest.
Savannah’s history can be told through its surviving architecture, including Georgian and Federal homes from the Colonial era, Greek Revival mansions from the cotton boom, and Victorian homes featuring intricate ironwork. The historic district — 2.5 square miles bordered by the Savannah River to the north — was designated a National Historic Landmark in 1966.
At $327,947, Savannah’s median home value falls between those in Pensacola and Gettysburg, and the cost of living is just 3% higher than the national average — reasonable for a coastal city with a rich historical heritage, as well as a variety of restaurants and nightlife options.
Gettysburg, Pennsylvania
For three days in 1863, 75,000 Confederate and Union soldiers fought across hills, wheat fields and peach orchards. When the guns fell silent on July 4, more than 51,000 men were killed, wounded or missing.
Four months later, President Lincoln arrived by train to dedicate the new National Soldiers’ Cemetery. He stayed all night at David Wells’ home in Lincoln Square, where he finished his remarks. The next morning, Lincoln delivered 272 speeches in two minutes—the Gettysburg Address, perhaps the most famous in American history.
Today, Gettysburg National Military Park preserves nine square miles of the battlefield. You can hike Little Round Top, stand where Pickett’s Charge began, and follow the stone walls of Cemetery Ridge where Union soldiers held the line.
Downtown Gettysburg, centered on Lincoln Square, has its own charm, with shops, art galleries, and restaurants. Built in 1776, Dobbin House Tavern serves candlelit dinners with wandering troubadours. Founded in 1832, Gettysburg College serves 2,600 students.
At $363,038, Gettysburg’s median home value is right in line with the national average, while the cost of living is 7% lower than the national average. It’s also easily accessible from other historic cities: it’s 52 miles from Baltimore and 90 miles from Washington, D.C.
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