Winston-Salem, North Carolina

Old & Lovely

Looklyloo Score: 80

View Full Profile


Young Professionals

Downtown Winston-Salem has gone through a huge transformation. Tobacco warehouses and knitting mills have been converted into beautiful urban lofts, art galleries and businesses. Downtown holds the Arts District, many of the music theaters, and plenty of cool restaurants and bars, which make the day and nightlife jumping around here. Cool loft living within walking distance of all of this fun makes this the starting point for most young professionals.

  • Downtown
  • Holly Avenue

Holly Avenue


Holly Avenue is a cool option for those who want to live within shouting distance of Downtown but get a bit of a break. Just southeast, this neighborhood has seriously fun, colorful bungalows and rejuvenated duplexes for anyone who wants walking access to a social scene but wants it at arm’s-length.

  • Holly Avenue

Sherwood Forest


Sherwood Forrest is a great starting point for a search for families. Classic brick homes fill tree-lined streets with huge lots, great walkable public schools and plenty of parks and sports fields for the little ones to recreate. It also has a great neighborhood pool that acts as a bit of a community center in warmer months. South Fork/Country Club is a posher spot for families, although the housing mix includes everything from massive to ranch-style and condos. Of course it houses a great Country Club but also includes great public schools, a Community Center and a beautiful public park.

  • Sherwood Forest
  • South Fork/Country Club
  • Washington Park

Homestead Hills


Winston-Salem is rated one of the nation’s best places to retire by US News. Some of this is mild weather, some is its low cost of living relative to the more popular cities in North Carolina, and some is due to the quality of healthcare, high safety-ranking, and active foodie and cultural scene. In addition to great neighborhoods, both suburban and city-centric, Winston-Salem has plenty of popular 55+ communities including: Homestead Hills, Arbor Ridge and a Bermuda Village, located just outside the city limits.

  • Homestead Hills
  • Arbor Ridge
  • Bermuda Village