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$299,900
1 Beds ⋅ 1 Baths ⋅ 1225988 MLS
Experience historic charm with modern updates in this top-floor 1-bedroom, 1-bath loft in the iconic Charles Building. This open-concept home features exposed brick walls, wood beams, hardwood floors, soaring ceilings, and a skylight that fills the space with natural light. Recent updates include all new windows and new kitchen appliances. The updated bathroom offers a large tiled walk-in shower, while the secured building includes a covered entrance, elevator access, and one parking space in the attached enclosed garage. Enjoy the shared rooftop deck with breathtaking views of the Innovation Quarter, downtown Winston-Salem, and the historic Reynolds Building. Located just one block from the Arts District, you'll be within just minutes of restaurants, shopping, and entertainment.

1 W 5th Street Unit #302, Winston-Salem
$369,900
2 Beds ⋅ 1 Baths ⋅ 1225452 MLS
Stunningly beautiful!  Experience urban living at its finest in this stylish loft at historic One West Fifth Street.  This 1925 building was thoughtfully converted to condominiums in 2003 and is ideally located in the heart of downtown Winston-Salem — just steps from Bailey Park, the Innovation Quarter, Trade Street, restaurants, entertainment, and cultural attractions. The open-concept interior blends modern convenience with historic character and features exposed brick, 16' ceilings, many built-ins, hardwood floors, and abundant natural light provided by new, oversized windows [2025] with remote-control shades! The spacious great room includes a lovely kitchen with bar seating, and a flexible living/dining space, while the primary suite features a generous, well-appointed, walk-in closet. Secure-access building with elevator, common areas, and a secure, private parking space.

1 W 5Th Street Unit #204, Winston-Salem
$399,900
2 Beds ⋅ 2 Baths ⋅ 1224190 MLS
Superb 2BR/2BA one-level residence near Bailey Park and the Innovation Quarter -- located in one of downtown's most charming buildings! Home to the Charles Department Store for decades, this iconic building was renovated into condominiums in 2003 and features a lobby with the original grand staircase leading up to a mezzanine-level common area; Inside, the open/airy interior offers all modern amenities combined with original exposed brick walls and high ceilings; Art gallery-style hallway leads to the great room -- containing the island-style kitchen, dining and living areas; Lovely primary suite with private bathroom and lots of closets; Second bedroom with skylight has direct access to the hall bathroom -- complete with tile shower; Large new windows (2025) overlook the Innovation Quarter and feature electric remote-control shades; Parking space within building's secure garage is included; Close to WFU, WSSU, UNCSA and Salem College and all that downtown Winston-Salem has to offer!

1 W 5th Street Unit #207, Winston-Salem
$449,900
2 Beds ⋅ 2 Baths ⋅ 1211994 MLS
List price includes a $25,000 Enhancement Credit -- use towards customizing residence to your taste OR as a lump-sum price reduction; Exciting urban living comes to life in this New York-style loft with new (2025) oversized windows, 16-ft tall ceilings & a private parking space--located in the heart of downtown Winston-Salem; Close to Innovation Qtr, Bailey Park, Aperture Cinema, Kaleideum, restaurants/bars + WFU,WSSU,UNCSA & Salem College; Granite kitchen with bar-style seating; Massive great room for living/dining; East loft caters exclusively to the primary suite with private BA + sitting area; West loft offers versatile home office; Main-level flex room/2nd BR -- complete with Murphy bed; The One West Fifth building housed the Charles Department Store for decades and was redeveloped into condominiums in 2003 -- and features a charming lobby with original grand staircase leading up to a mezzanine-level common area; The 2 areas below the lofts have ceiling heights slightly below 7-ft

1 W 5th Street Unit #102, 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 .