The United States is a young nation, but some of its cities have centuries of history that predate the country’s founding in 1776. These cities were once bustling trade hubs, colonial outposts, and political capitals that played a significant role in the nation’s creation. Today, they offer a unique blend of historic charm and modern convenience, which makes them attractive to homebuyers who seek character, culture, and a strong sense of history. From the cobblestone streets of Charleston to the historic landmarks of Boston, let’s walk through some of the oldest cities in the U.S. and why they are great to live in.

10. Philadelphia, PA (1682)

Median Home Sale Price: $260,000

Median Rent Price (1 Bedroom): $1,860

Philadelphia was founded by William Penn as a Quaker colony and quickly grew into a commercial and political hub. Commonly known as the birthplace of American freedom, it is the site where the Declaration of Independence was signed. Today, it blends the old with modern urban living. With historic attractions like Independence Hall and the Liberty Bell, it attracts millions of visitors, while vibrant neighborhoods and career opportunities in healthcare and technology make it an excellent city to call home. Compared to older European cities, Philadelphia offers an American historical experience with a mix of old and new.

9. Charleston, SC (1670)

Median Home Sale Price: $681,250

Median Rent Price (1 Bedroom): $1,641

Charleston was founded as an English colony and played a significant role in the American Revolution and the Civil War. With its pre-Civil War homes, gas-lit streets, and deep Southern heritage, it is one of the most picturesque cities in America. Well known for its Civil War history and well-preserved historic districts, Charleston offers the coastal lifestyle with a vibrant arts and food scene. Compared to larger cities, Charleston has a slower pace of life without giving up too much in the way of cultural activities.

8. Newport, RI (1639)

Median Home Sale Price: $870,000

Median Rent Price (1 Bedroom): $1,348

Founded by religious dissidents seeking freedom, Newport quickly developed into a thriving maritime center. One-time summer playground of America’s elite, Newport is famous for its Gilded Age mansions, sailing history, and seaside charm. The city’s walkability and festive atmosphere make it an appealing place to settle down, especially for those who appreciate a mix of oceanfront leisure and rich history. Newport’s historic preservation is comparable to that of European coastal cities, which makes it quite unique among American cities.

7. Boston, MA (1630)

Median Home Sale Price: $842,500

Median Rent Price (1 Bedroom): $3,732

One of the key cities of the American Revolution, Boston was the launching point for the Boston Tea Party and Paul Revere’s ride. A living museum of the Revolution, the city boasts the Freedom Trail, Boston Common, and Faneuil Hall. Along with history, Boston is a robust hub for education, healthcare, and technology, so it’s a great place for professionals as well as history buffs. Boston possesses an intellectual vibrancy unlike other American cities, due to its world-class universities and research centers.

6. Salem, MA (1626)

Median Home Sale Price: $597,500

Median Rent Price (1 Bedroom): $2,090

A former major trading and fishing port, Salem became famous for the Salem Witch Trials of 1692. Today, it has capitalized on its colonial past with attractions like the Witch House, Peabody Essex Museum, and a thriving tourism industry centered around its colonial history. With an active waterfront, historic homes, and a lively arts community, Salem offers a more low-key alternative to Boston without giving up cultural cache. Unlike other cities on this list, Salem has a unique mystical appeal that draws visitors and residents.

Click here to learn more and subscribe to the newsletter

5. New York City, NY (1624)

Median Home Sale Price: $807,703

Median Rent Price (1 Bedroom): $4,636

New York City was first established by the Dutch as a significant trading center known as New Amsterdam. It later was taken over by the British and renamed. It has evolved over the centuries to become a global leader in finance, culture, and immigration. The housing in the city varies from older brownstones in Brooklyn to modern skyscrapers in Manhattan. Unlike most older cities that are centered around preservation, New York is always reinventing itself without ever losing its deeply rooted history.

4. Plymouth, MA (1620)

Median Home Sale Price: $650,000

Median Rent Price (1 Bedroom): $2,566

Plymouth is famous as the Pilgrims’ point of arrival and was the first permanent English settlement in New England. It retains colonial charm with attractions like Plymouth Rock and Plimoth Patuxet Museums. While its historic roots are strong, Plymouth also has a scenic coastal setting and contemporary amenities, so it is a balanced community to live in.

3. Santa Fe, NM (1610)

Median Home Sale Price: $537,500

Median Rent Price (1 Bedroom): $1,935

Santa Fe was established by Spanish colonists and is the oldest state capital in the United States. It was a key trade and Spanish government hub in the region. Today, it is known for its distinctive adobe architecture, vibrant arts community, and Native American and Spanish cultural blend. Unlike the East Coast historic cities that are mainly dominated by European colonial history, Santa Fe’s history is marked by indigenous peoples and Spanish colonization, making it distinct as a cultural hub in the Southwest.

2. Jamestown, VA (1607)

Median Home Sale Price (Williamsburg): $355,000

Median Rent Price (1 Bedroom, Williamsburg): $1,598

America’s first permanent English settlement, Jamestown, fought extreme hardship in its early years. Its rich history is preserved through archaeological digs and museum displays. Its peaceful atmosphere and close proximity to nearby Williamsburg make it a desirable choice for those who appreciate history but would prefer a more low-key lifestyle than city living.

1. St. Augustine, FL (1565)

Median Home Sale Price: $492,500

Median Rent Price (1 Bedroom): $1,550

Founded by Spanish explorers, St. Augustine is the oldest continuously inhabited city in the U.S. It played a significant city in colonial-era wars between Spain, Britain, and finally, the United States. Today, its Spanish colonial architecture, historic fortifications, and coastal locale make it a lovely city to call home. In contrast to the other cities on this list, St. Augustine provides richly ingrained history along with a warm, tropical climate, perfect for anyone who desires both culture and coastal living. 

Get your free guide “Passive Real Estate Investing For Busy Professionals”

Conclusion 

To call one of America’s oldest cities home is to embrace a lifestyle rich in history, culture, and architectural beauty. Each city has its own unique character—Boston’s intellectual energy, Charleston’s Southern charm, and Santa Fe’s artsy vibe all contribute to the nation’s diverse urban landscape. Buyers seeking a balance between old and new will find these historic cities full of charm and possibilities.

From colonial facades to grand Art Deco masterpieces, these cities showcase a rich architectural tapestry that tells the story of their past. As city skylines evolve, these old cities prove that while modernization is inevitable, history is an invaluable part of their enduring appeal.

Share this: