Key Takeaways
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From antebellum mansions in Natchez, Missippi, to the battlefields of Gettysburg, Pennsylvania, these five towns surround you with history.
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Each destination has a profound cultural heritage as well as below-average living costs, making them suitable for retirees and history lovers alike.
While tourist accommodations in cities like Boston command premium prices due to their colonial charms, dozens of other American locales offer equally compelling heritage, such as Revolutionary War battlefields, Spanish missions, and antebellum architecture, all at a fraction of the cost.
Using Zillow’s Home Value Index and the Economic Research Institute’s cost-of-living data, 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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A view of the Natchez-Vidalia bridge that connects the two cities.
Natchez, Mississippi
After walking Natchez in 1852, famed landscape architect Frederick Law Olmsted suggested the geometry of the “abrupt precipice over the river, with the public garden upon it . . . on the very edge of a stupendous cliff” could hardly be improved upon. Look out from Natchez Bluff just before dusk, with its panoply of purples and oranges across the horizon, and you’re bound to agree. Almost 200 feet above the water, the view stretches for miles in both directions, with riverboats drifting past year-round.
In the decades before the Civil War, Natchez had the most millionaires per capita in the U.S. When Natchez surrendered to Union forces in 1862, its mansions were spared, which means Natchez can now lay claim to more antebellum mansions than anywhere else in the South, as well as over 1,000 structures on the National Register of Historic Places.
At $115,132, Natchez has the most affordable average home value on our list. It is located in a county with the lowest median home value among attractive U.S. retirement locations offering affordable housing. That affordability is a reflection of Natchez’s low cost of living, which is 21% below the national average. Mississippi also doesn’t tax Social Security or retirement income, saving you even more.
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Christmas Lights along the San Antonio downtown River Walk.
San Antonio, Texas
Surrounded by skyscrapers in downtown San Antonio is the Alamo, the famed 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 more missions that collectively form a UNESCO World Heritage Site.
Mission San José, dubbed the “Queen of the Missions,” is the largest, with Texas limestone walls and an elaborate Spanish colonial architecture. History isn’t over for these missions: all four churches are active Catholic parishes, and parishioners are known for their volunteer work along the U.S.-Mexican border.
Downtown, the River Walk winds through the city 20 feet below street level—an urban waterway lined with cypress trees, restaurants, bars, and live music venues. There are festivals year-round, like the Fiesta San Antonio in April and the Day of the Dead River Parade in the fall.
At about $247,152, San Antonio’s average home value is significantly below the national average of $360,7273, and the cost of living is 6% lower than the national average. Texas doesn’t tax state income, leaving you with more of your money for the fresh Mexican fare served along the River Walk.
Pensacola sits on the Gulf Coast with 8.5 miles of sugar-white sand beaches just minutes from downtown.
While lesser known than those in New Orleans, the Mardi Gras parade in Pensacola brings in many revelers.
Pensacola, Florida
The oldest European settlement in the U.S., Pensacola is where Spanish explorer Tristán de Luna landed in 1559 with 11 ships from Veracruz, Mexico. The Luna settlement predates St. Augustine by six years and Jamestown by 48.
Pensacola later became a strategic military outpost that changed hands under the U.K., Spain, France, and the U.S. History is still being found in these parts: University of West Florida archaeologists discovered the original Luna settlement site in 2015, unearthing 16th-century Spanish ceramics, glass trade beads, and wrought-iron nails in a residential neighborhood.
Downtown Pensacola’s Historic District, centered around Seville Square and Plaza Ferdinand VII (the original British parade grounds), spans eight and a half acres with 28 historic buildings. Spanish Colonial architecture lines brick sidewalks, while the 1907 Pensacola Museum of History occupies a Mediterranean Revival building with a red tile roof and arched entry porch.
At $259,932, Pensacola’s average home value sits just above San Antonio’s but well below Florida’s famous southerly coastal cities like Boca Raton. The cost of living runs 11% below the national average, and Florida’s lack of state income tax sweetens the deal.
Savannah’s tree-lined streets add to the historical allure of the city.
Savannah, Georgia
In 1733, General James Oglethorpe designed Savannah around a grid of squares—park-like open spaces surrounded by residential and civic buildings in repeating “wards.” Twenty-two squares remain today, shaded by live oaks draped 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 houses featuring intricate ironwork. The Historic District—2.5 square miles bounded by the Savannah River to the north—was designated a National Historic Landmark in 1966.
At $327,947, Savannah’s average home value sits between those of Pensacola and Gettysburg, and the cost of living runs just 3% above the national average—reasonable for a coastal city with such a rich historical heritage, as well as a variety of restaurants and nightlife options.
Sunset at the “High Water Mark” of the Gettysburg Battlefield. The area was the site of the U.S.’s deadliest battle.
Gettysburg, Pennsylvania
For three days in 1863, 75,000 Confederate and Union soldiers fought across ridges, wheat fields, and peach orchards. When the guns fell silent on July 4, over 51,000 men were dead, wounded, or missing.
Four months later, President Lincoln arrived by train to dedicate the new Soldiers’ National Cemetery. He stayed overnight at the David Wills House on Lincoln Square, where he finalized his remarks. The next morning, Lincoln delivered 272 words in two minutes—the Gettysburg Address, perhaps the best known in American history.
Today, Gettysburg National Military Park preserves nine square miles of battlefield. You can walk Little Round Top, stand where Pickett’s Charge began, trace the stone walls at Cemetery Ridge where Union soldiers held the line.
Downtown Gettysburg, centered on Lincoln Square, offers its own charms, with boutiques, art galleries, and restaurants. The Dobbin House Tavern, built in 1776, serves dinner by candlelight with roving troubadours. Gettysburg College, founded in 1832, serves 2,600 students.
At $363,038, Gettysburg’s average home value is right at the national median, while the cost of living runs 7% below the national average. It’s also quite accessible to other historic cities: it’s 52 miles from Baltimore and 90 miles from Washington, D.C.
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