A Neighborhood Just Above Downtown
Chestnut Hills sits immediately north of downtown Asheville, close enough to walk to Pack Square yet tucked into a leafy rise of land that feels distinctly residential. Its streets extend roughly from East Chestnut Street and Merrimon Avenue north toward Hillside Street, with Washington Street, Julia Street, Annandale Avenue, Cornelia Street, and nearby Charlotte Street helping define the neighborhood’s historic setting. Much of the area is included within Asheville’s larger Chestnut Hill Historic District, listed in the National Register of Historic Places in 1983.
For longtime residents, the appeal is easy to understand. Chestnut Hills has the convenience of an in-town neighborhood but the atmosphere of an older village: mature trees arch over brick sidewalks, front porches face the street, and houses from several generations stand comfortably alongside one another.
The name is a simple one, rooted in the neighborhood’s geography and its principal street. Chestnut Hill is located on a prominent knoll north of Asheville’s original center, while East and West Chestnut streets have long served as the area’s most recognizable routes. The historic district’s name reflects both that elevated terrain and the street that bisects it.
From Rural Edge to Streetcar-Era Suburb
Before the neighborhood filled with houses, this land lay beyond Asheville’s compact nineteenth-century town center. The city’s growth accelerated after the railroad reached Asheville in the late nineteenth century. New arrivals, investors, physicians, attorneys, merchants, and seasonal visitors all helped create demand for housing on the hills surrounding downtown.
A major step came in 1884, when Alice T. Connally of Fernihurst purchased and subdivided land that became known as the Connally Addition. The property covered much of the area between Merrimon Avenue and Charlotte Street, with Murdock Street—now Hillside Street—and Chestnut Street marking important edges. The subdivision helped open Chestnut Hills to residential development during Asheville’s land boom of the 1880s and 1890s.
The earliest houses were often substantial farmhouses or country residences, reminders that the neighborhood began as an outlying district rather than a fully urban subdivision. By the 1890s and early 1900s, however, Chestnut Hills had become one of Asheville’s most fashionable residential areas. Some homes were built for year-round residents, while others served as summer or winter “cottages” for visitors drawn to Asheville’s climate and growing reputation as a health resort.
Architecture with Asheville Character
One of the great pleasures of walking Chestnut Hills is seeing how many architectural styles share the same blocks. Along East Chestnut Street and the surrounding side streets are Queen Anne-influenced houses, Colonial Revival residences, bracketed Victorian homes, cottages, and early twentieth-century bungalows. Many properties combine shingles, pebbledash stucco, stone, and painted wood in ways that feel especially suited to the mountains.
Two architects are particularly important to the neighborhood’s story. Richard Sharp Smith, supervising architect for George Vanderbilt’s Biltmore House and later a prominent Asheville architect, designed several Chestnut Hill residences. His work often blends English-influenced forms with local materials and picturesque rooflines. Architect James A. Tennent, known for designing several of Asheville’s major civic buildings, also made his home in the district.
Among the notable residences is Beaufort Lodge, the former Theodore Davidson House at 61 North Liberty Street. Davidson served as North Carolina’s attorney general and was one of the prominent citizens associated with Asheville’s development. Another important figure was Swiss physician J. E. David, whose homes and cottages on East Chestnut Street remain associated with the neighborhood’s architectural heritage.
The property histories also reflect the city’s larger network of civic and business leaders. George Pack, a major Asheville philanthropist, once lived at Many Oaks, a large home near Merrimon Avenue and West Chestnut Street. The house no longer stands; its former site is now associated with commercial development. Even so, Many Oaks remains part of the neighborhood’s remembered landscape.
Churches, Schools, and Community Life
Chestnut Hills was never only a collection of impressive houses. It developed as a lived-in community with churches, schools, professional offices, apartments, and neighborhood businesses.
St. Mark’s Lutheran Church, St. Paul’s United Methodist Church, and Beth Ha-Tephila Congregation all contribute to the area’s institutional history. Their presence illustrates the variety of religious communities that helped shape Asheville during the late nineteenth and early twentieth centuries. Claxton Elementary School adds another important layer, connecting the neighborhood to generations of Asheville children and families.
The neighborhood’s proximity to downtown also gave residents easy access to markets, doctors’ offices, hotels, theaters, and civic buildings. In the early twentieth century, Chestnut Hills occupied a useful middle ground: private and peaceful, yet not isolated from the energy of central Asheville.
Midcentury Change and the Expressway
Like many older urban neighborhoods, Chestnut Hills faced major changes after World War II. Automobile travel reshaped Merrimon Avenue and other nearby corridors, while downtown Asheville experienced commercial and population shifts. In the 1960s, construction of the downtown expressway created a powerful physical boundary between Chestnut Hill and the central business district. The highway occupied the low area between the downtown plateau and the neighborhood’s higher ground, changing familiar walking and driving routes.
Yet the neighborhood retained much of its historic fabric. Large homes were divided into apartments or offices, older houses were renovated, and bungalows from the 1910s and 1920s continued to fill in the spaces between Victorian-era residences. The result is a neighborhood with mixed density and a wide range of household types—one reason Chestnut Hills still feels more like a real community than a preserved museum district.
Preservation and the Present Day
The National Register designation helped recognize Chestnut Hill’s architectural and historical importance. It also placed the neighborhood within Asheville’s broader preservation story, alongside Montford, Grove Park, and other historic areas. A National Register listing does not automatically prevent alterations or demolition, but it documents the district’s significance and may support preservation incentives for qualifying rehabilitation projects.
Today, Chestnut Hills continues to evolve. Merrimon Avenue brings increasing traffic and commercial activity, while nearby streets remain primarily residential. Residents have long emphasized the importance of maintaining brick sidewalks, granite curbs, mature trees, gardens, and the walkable relationship between homes, schools, churches, and businesses. Those details are more than attractive scenery; they are the physical record of how the neighborhood grew.
What makes Chestnut Hills special is not a single mansion or landmark. It is the layering of Asheville history in one compact place: farmhouses beside Queen Anne homes, bungalows beside professional offices, churches near schools, and old brick sidewalks leading toward downtown. A walk along East Chestnut, North Liberty, or Washington Street can still reveal the ambitions of railroad-era Asheville—and the care of later residents who chose to keep those streets alive.