Holly Avenue Historic District Real Estate

Welcome to the Holly Avenue Historic District, a captivating neighborhood nestled in the heart of Winston-Salem, North Carolina. This charming subdivision is a treasure trove of architectural beauty and rich history, making it a sought-after locale for those who appreciate the allure of bygone eras.

Established in the early 20th century, the Holly Avenue Historic District showcases a stunning collection of homes that reflect various architectural styles, including Craftsman, Colonial Revival, and Bungalow. As you stroll down the tree-lined streets, you’ll be enchanted by the intricate details and unique character of each residence, many of which have been lovingly preserved or restored.

The community is not just about beautiful homes; it’s also steeped in a vibrant history that tells the story of Winston-Salem’s growth and development. The district is listed on the National Register of Historic Places, underscoring its significance and charm. Residents enjoy a strong sense of community, with neighborhood events and gatherings that foster connections among neighbors.

Conveniently located, the Holly Avenue Historic District offers easy access to downtown Winston-Salem, where you can explore an array of dining, shopping, and cultural experiences. Nearby parks and recreational areas provide ample opportunities for outdoor activities, making it an ideal spot for families and individuals alike.

Whether you’re looking to settle down in a historic home or simply wish to immerse yourself in a community rich with character and charm, the Holly Avenue Historic District is a perfect choice. Discover the beauty and history waiting for you in this enchanting neighborhood!

Newest Listings in Holly Avenue Historic District

$409,900

3 Beds ⋅ 4 Baths ⋅ 1223191 MLS

Rare find in Winston-Salem's historic Holly Avenue neighborhood-this beautifully updated 1923 bungalow delivers character, flexibility & income potential. Live in it as a stunning single-family home or make it a live-in investment w/built-in rental income. Main level shines with soaring ceilings, hardwoods, gas FP, separate dining room & sun drenched updated kitchen. Primary suite features a freestanding soaking tub & separate tile shower. Half bath & laundry w/W&D included. Upstairs: a fully self-contained apartment w/private entrance, living room, kitchen, 2 bedrooms, full bath w/clawfoot tub & washer & dryer-ready to rent from day one, host guests, or convert to a 4th bedroom. Ample storage in the large closets, bsmt & shed out back. Wide rocking chair front porch, fenced yard & off street parking-genuine rarities this close to downtown. Live next to W-S's best restaurants, coffee shops, shops, event spaces & parks. Historic charm, modern updates & a location that can't be beat!

523 W First Street, Winston-Salem

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Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .