Holly Avenue Historic District Homes for Sale

Welcome to the Holly Avenue Historic District, a charming enclave nestled in the heart of Winston-Salem, North Carolina. This vibrant neighborhood is steeped in history and character, showcasing a delightful array of architectural styles that reflect the rich heritage of the area. From stately Victorian homes to quaint Craftsman bungalows, the Holly Avenue Historic District offers a picturesque setting that captures the essence of Southern charm.

As you stroll through the tree-lined streets, you'll be enchanted by the meticulously maintained gardens and the warm sense of community that permeates the air. The district is not just a feast for the eyes; it’s a lifestyle choice for those who appreciate the blend of history and modern living. Residents enjoy easy access to local parks, cultural attractions, and a plethora of dining and shopping options that Winston-Salem has to offer.

Currently, there are a variety of homes for sale in this sought-after district. Whether you’re a first-time homebuyer or looking to downsize, you’ll find an array of options that cater to different tastes and budgets. Each home tells its own story, waiting for the right owner to add their personal touch. With the perfect mix of historic charm and contemporary amenities, the Holly Avenue Historic District is more than just a place to live; it’s a community where memories are made.

Come explore the possibilities of calling this enchanting neighborhood home. Discover your dream residence in the Holly Avenue Historic District today!

Newest Holly Avenue Historic District Homes for Sale

$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 .