Fifth Street Historic Homes for Sale in Winston-Salem NC
The one Winston-Salem street where you can buy a 1925 downtown loft, a Craftsman bungalow, or a Neo-Classical mansion on the same walking route.
Fifth Street by the Numbers
Lifestyle Along Fifth Street
The Downtown Loft End (Blocks 1 through 100 West)
The eastern anchor of Fifth Street is the Charles Building at 1 W Fifth Street, a 1925 department store converted to condominiums in 2003. The building sits at Fifth and Main and looks straight into the Innovation Quarter across the street. Walk Score is 86. From your front door, you can be at Bailey Park in under two minutes, Trade Street restaurants in five, and the Arts District in seven. This end of Fifth Street lives like a genuine urban neighborhood in a way no other Winston-Salem address does. The new $25 million downtown amphitheater breaking ground in 2026 sits within a five-minute walk. The Grounds $250 million mixed-use project targeting August 2027 sits two blocks north.
The Historic Mansion Corridor (Blocks 400 through 1000 West)
Cross Broad Street and Fifth Street changes character. This is the West End Historic District proper, listed on the National Register of Historic Places in 1986. The 500, 600, 700, 800, and 900 blocks of West Fifth Street are lined with Neo-Classical Revival, Colonial Revival, Queen Anne, and Craftsman homes built between the 1880s and 1930. Locals call the grandest stretch Millionaires Row. The Rosenbacher House at 848 W Fifth (1909) is one of the finest Neo-Classical Revival dwellings in Winston-Salem. The Agnew Hunter Bahnson House at Fifth and Spring Streets (1920, Willard C. Northup architect) is on the National Register individually.
The Craftsman Bungalow End (1000 Block West and Beyond)
West of 1000 W Fifth, the street settles into a rhythm of 1920s Craftsman bungalows with tapered columns, exposed rafter tails, and deep front porches. These are the more accessible entry points into the West End Historic District. Prices in the 1000 through 1400 blocks typically sit $200,000 to $400,000 below the mansion corridor, giving character-preservation buyers a real path in.
What You Walk To From Any Point on Fifth
- Bailey Park and Innovation Quarter — the Wake Forest tech and life-sciences campus, two to seven minutes east depending on your block
- Grace Court and Restaurant Row — the walkable West End dining cluster around West End Boulevard
- Hanes Park — 40 acres of green space at the northern edge of the district
- Downtown Winston-Salem Arts District and Trade Street — galleries, breweries, and independent shops
- Historic Old Salem and Salem College — ten to fifteen minutes south by car
About Fifth Street Historic
Fifth Street is the residential spine of the West End Historic District, and it is genuinely three neighborhoods pretending to be one street. That is what makes it worth its own guide rather than a footnote in the West End write-up.
At the east end, the Charles Building at 1 W Fifth Street holds roughly forty converted downtown condominiums with 16-foot ceilings, original hardwood floors, and exposed brick. Recent 2026 listings include a 790-square-foot one-bedroom top-floor loft at $299,900, a 1,224-square-foot two-bedroom at $369,900, and larger two-bedroom lofts at $449,900. Monthly HOA runs about $614 and covers building security, elevator, and secured parking. This is the youngest and most active resale product on the street.
The middle stretch, from about Broad Street west to the 1000 block, is the historic mansion corridor. The Rosenbacher House at 848 W Fifth sits atop a terraced lawn, dominated by a monumental two-story central portico with Corinthian columns. The Bahnson House at Fifth and Spring is a stuccoed English Cottage variant designed in 1920 by Willard C. Northup. The Taylor Houses at 1000, 1012, and 1014-1016 W Fifth are prime examples of stuccoed early-twentieth-century domestic architecture. This corridor rarely turns inventory. When these homes list, they land in the $700,000 to $1.4 million range depending on lot size, condition, and whether historic tax credits have already been used.
Beyond the 1000 block, the street settles into Craftsman bungalows. These are the entry points, sometimes trading $340,000 to $500,000, sometimes closer to $600,000 if a full restoration has been done. First-time character-home buyers land here regularly. Preservation-minded downsizers do too.
The through-line across all three sections is the West End Historic Overlay District, a local designation administered by the Forsyth County Historic Resources Commission that regulates exterior changes visible from the street. Exceptions apply to the 1 W Fifth lofts because they operate under a building HOA rather than the overlay commission. Understanding which rule set applies to a specific address on Fifth Street matters more than most Winston-Salem buyers realize the first time through, and it can meaningfully affect renovation timelines and cost.
Current Fifth Street Homes for Sale
Live MLS listings updated every 15 minutes for downtown Winston-Salem and the West End corridor including all of West Fifth Street, powered by IHF Kestrel. Call directly for private-office and pre-list inventory not shown here.
Schools Serving Fifth Street Historic
Fifth Street residents in zip 27101 are typically zoned to Winston-Salem/Forsyth County Schools below. Verify current assignment with WS/FCS before purchase because the district uses a choice-based enrollment overlay on some blocks.
Grades K-5. Downtown-area elementary with Title I resources and a robust arts program. Draws from downtown loft residents, West End historic homes, and Northeast Winston-Salem.
Grades 6-8. Located on Northwest Boulevard within a short drive of Fifth Street residents. Solid arts and STEM programming with an established feeder relationship into R.J. Reynolds High.
Grades 9-12. One of the top-rated public high schools in the Triad with strong AP and IB offerings, competitive athletics, and a robust arts program. R.J. Reynolds High is a legitimate school-quality reason many families prioritize the West End and Fifth Street.
Frequently Asked Questions
West Fifth Street is the residential spine of the West End Historic District, running from downtown at 1 W Fifth Street west through Millionaires Row to the 1400 block. The street contains three distinct product types in one walkable corridor: converted downtown lofts at 1 W Fifth (Charles Building, 1925), Neo-Classical Revival mansions from 1900-1930 including the Rosenbacher House and Bahnson House, and Craftsman bungalows on the western blocks. All are inside the West End National Register Historic District listed in 1986.
The Fifth Street residential median in 2026 sits around $385,000, though the range is unusually wide. Downtown lofts at 1 W Fifth trade $275,000 to $660,000 depending on square footage. Historic homes on the western blocks range $340,000 to $700,000 for mid-sized restored houses. Grand Neo-Classical mansions on Millionaires Row trade $900,000 to $1.4 million or more, depending on condition and lot size.
Yes. The Charles Building at 1 W Fifth Street was built in 1925 as a downtown Winston-Salem department store, converted to condominiums in 2003, and typically has three to six active listings at any given time. Recent 2026 comparables include a 790-square-foot one-bedroom at $299,900, a 1,224-square-foot two-bedroom at $369,900, and larger 2,000-plus-square-foot two-bedroom units at $449,900. Monthly HOA runs about $614.
Yes. West Fifth Street forms the primary residential axis of the West End Historic District, listed on the National Register of Historic Places in 1986 with 508 contributing buildings dating from 1887 to 1930. Some Fifth Street properties are additionally landmarked, including the Rosenbacher House at 848 W Fifth (1909) and the Agnew Hunter Bahnson House at Fifth and Spring Streets (1920). National Register listing qualifies certain renovations for North Carolina historic preservation tax credits offsetting 15 to 30 percent of qualifying work.
Fifth Street residents in zip 27101 are typically zoned to Brunson Elementary, Wiley Middle School, and Richard J. Reynolds High School under Winston-Salem/Forsyth County Schools. Verify assignment with WS/FCS before purchase because the district uses a choice-based enrollment overlay for some blocks. R.J. Reynolds High is one of the highest-rated public high schools in the Triad.
The eastern half of Fifth Street is one of the most walkable residential addresses in the Triad. The 1 W Fifth building has a Walk Score of 86 and sits within a two-block walk of Bailey Park, Innovation Quarter, Trade Street restaurants, and the Arts District. Historic homes on Millionaires Row further west are a longer walk but still under 15 minutes to downtown, with sidewalks the entire route.
Fifth Street works for three very different buyer profiles. Young professionals and empty-nesters who want the loft-and-walkability lifestyle land at 1 W Fifth or similar downtown-edge condominiums. Historic-home enthusiasts who want architectural character with tax credits land in the 400 through 1000 blocks. Higher-net-worth buyers who want a legacy home with grand-scale architecture and lot size land on Millionaires Row proper. All three share the same walkable neighborhood energy.
Yes for most of Fifth Street west of downtown. The West End Historic Overlay District is a local designation administered by the Forsyth County Historic Resources Commission that applies to most Fifth Street residential properties. Exterior changes visible from the street require a Certificate of Appropriateness. Interior work is not regulated. Downtown lofts at 1 W Fifth are governed by the building HOA rather than the overlay commission, so they have different rules.
Keep Reading
- About Teresa Overcash — 30 years of NC selling
- Moving to Winston-Salem NC — complete relocation guide
- NC Real Estate Glossary — every term defined
- West End Winston-Salem full neighborhood guide — the historic district that surrounds Fifth Street
- Downtown Winston-Salem 2026 development guide — The Grounds, amphitheater, and Northeast redevelopment
- All Winston-Salem homes for sale
- All NC neighborhoods
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