Winston-Salem, North Carolina, is a city steeped in history and Southern charm where cobblestone streets meet 20th-century craftsmanship. For homebuyers seeking architectural character without the high price tag, these four timeless properties offer just that. From a Cottage-Style gem to a Bungalow bursting with period details, each home on this list blends vintage elegance with lasting value. Even better? Every one of them is listed under $300,000. Let’s take a closer look.
1. 1920 Colonial Revival in Winston-Salem
This beautifully updated 1920 Colonial Revival home sits in historic Reynolds Town, just minutes from downtown Winston-Salem, NC. Priced at $216,000, it offers 1,560 sq ft of finished space on a 0.14-acre lot. Notable features include original hardwoods, new HVAC, updated light fixtures, and a refreshed kitchen with new appliances. A spacious semi-finished basement adds flexible potential. This timeless brick home blends classic architecture with thoughtful modern upgrades.
Where is Winston-Salem?
Winston-Salem lies in the heart of North Carolina’s Piedmont Triad, near Greensboro and High Point. Founded by Moravians in the 1700s, the city grew through tobacco and textile industries. Today, it’s known for arts, history, and innovation, home to Old Salem, Wake Forest University, and vibrant neighborhoods. Its historic architecture and cultural depth make it a destination for heritage lovers and modern homeowners alike.
Living Room
This sunlit living room features gleaming hardwood floors, soft gray walls, and crisp white trim for a refined yet cozy feel. A classic white fireplace serves as the focal point, flanked by two tall windows that bring in natural light. A large front window brightens the space further, creating a warm, welcoming atmosphere. The open layout offers plenty of room for comfortable seating and easy entertaining.
Kitchen
The kitchen features warm natural wood cabinets and durable laminate countertops, offering ample storage and workspace. New stainless appliances, including a refrigerator and electric range, provide modern convenience. Vinyl plank flooring complements the soft gray walls, giving the room a fresh, updated look. A wide window above the sink invites daylight into the space, enhancing its functional and airy feel. Perfect for home chefs and family meals alike.
Breakfast Nook
This charming breakfast nook is nestled beside the kitchen, ideal for casual dining. A bright window provides soft natural light, while neutral gray walls and white trim create a clean, cheerful tone. Matching vinyl flooring ties it into the adjacent spaces. Compact yet inviting, this nook is perfect for morning coffee or quick meals, and its open connection to the kitchen enhances the flow of the main level.
Den
The den offers classic character with painted beadboard walls, a paneled ceiling, and built-in bookshelves for storage and display. A ceiling fan adds comfort, while vinyl plank floors give the room a modern touch. Light enters through a side window and a rear door with glass paneling, brightening the space. Ideal as a home office, library, or creative studio, this room blends period charm with everyday functionality.
Primary Bedroom
The spacious primary bedroom features rich hardwood floors, soft gray walls, and crisp white trim for a calming, elegant aesthetic. A central white fireplace adds historic charm and warmth, while three large windows allow for excellent natural light throughout the day. A ceiling fan provides comfort and airflow. With its generous layout and serene atmosphere, this upstairs retreat perfectly combines modern comfort with early 20th-century character
Source: Mundy Realty Inc. Via Zillow
2. 1925 Bungalow Cottage in Winston-Salem
This 1925 Stick-Built Bungalow in the Washington Park Historic District offers timeless charm with thoughtful updates. Priced at $289,900, the 1,041-square-foot home sits on a 0.17-acre lot and is fully furnished as a turnkey Airbnb. Recent renovations include refinished hardwood floors, fresh paint, and luxury vinyl plank flooring throughout. Its single-story layout and welcoming façade make it ideal for short-term rental or cozy full-time living in a prime location.
Where is Winston-Salem?
Winston-Salem is in the north-central region of North Carolina, part of the culturally rich Piedmont Triad. Just west of Greensboro, the city blends historic charm with modern energy. Known for its Moravian roots and the legacy of R.J. Reynolds, Winston-Salem now thrives with arts, universities, and revitalized historic districts like Washington Park. Residents enjoy proximity to downtown shops, nature trails, and one of the state’s most vibrant food scenes.
Side Porch
The side porch offers a cozy outdoor retreat framed by classic white lattice railings and sheltered beneath a wide overhang. Two Adirondack chairs create an inviting spot to relax, enjoy morning coffee, or take in views of the wooded neighborhood. Vinyl siding and neutral tones lend a clean, fresh look, while soft natural light adds warmth to this private and peaceful space—perfect for quiet moments or casual conversation.
Dining Area
This cheerful dining area features a six-seat wood table with white frame chairs and a matching dark wood top. The soft gray walls provide a contemporary backdrop, enhanced by crisp white trim and two wide windows with blinds for adjustable light. A round, textured pendant light adds a touch of modern elegance above the table. It’s a stylish and inviting space for daily meals or entertaining guests.
Primary Bedroom
The primary bedroom exudes comfort with its muted gray walls, white ceiling fan, and refinished hardwood flooring. A plush bed dressed in crisp white linens sits beneath framed wall art, complemented by a cozy armchair and light wood nightstands. A single window with white curtains allows sunlight to softly brighten the room. This peaceful space combines traditional charm with modern comfort, ideal for restful nights and relaxed mornings.
Hallway
The central hallway connects the home with warm hardwood flooring, clean lines, and fresh neutral tones. Off-white trim defines each doorway, while soft lighting above provides clarity and warmth. Tile flooring at the entry transitions seamlessly to hardwood, giving the space both style and function. This welcoming corridor provides easy access to bedrooms and common areas, all while maintaining the home’s cohesive and polished interior design.
Entryway
The entryway blends simplicity and elegance with soft gray walls, a creamy tiled floor, and crisp white trim. A striped rug adds texture underfoot, while a decorative wall piece and clean-lined baseboards enhance the look. This small but functional space transitions smoothly into the main living area and hallway, offering a tidy and stylish welcome to the home’s inviting interior. It sets the tone for the thoughtfully updated spaces beyond.
Living & Dining
This open-concept living and dining space features gleaming refinished hardwood floors and a soft gray color palette that creates a warm, cohesive atmosphere. A large, plush sectional sofa faces a wall-mounted TV, while nearby, a six-seat dining table with white chairs adds charm and functionality. Three wide windows fill the room with daylight, and overhead, a ceiling fan and pendant light add style and comfort to this bright, welcoming area.
Source: TKG Real Estate Via Zillow
3. 1900 Cottage-Style Home in Winston-Salem
Built-in 1900, this single-story cottage-style home rests on a generous 2.74-acre lot in the Bethania area of Winston-Salem, NC. Priced at $205,000, it offers 1,620 square feet of living space and includes three bedrooms and two full baths. The property features a large detached two-car garage, ideal for a workshop or hobby space. With vintage charm and ample space, this city-lot home invites renovation and personal vision.
Where is Winston-Salem?
Located in the Piedmont Triad region of North Carolina, Winston-Salem blends deep Moravian roots with a legacy in tobacco and textiles. Surrounded by rolling hills and close to Greensboro and High Point, the city offers a mix of historic neighborhoods and modern development. Cultural landmarks like Old Salem and Reynolda House draw visitors, while parks, greenways, and a growing arts scene contribute to the city’s vibrant quality of life.
Side Yard
This wide side yard reveals the spacious layout of the 2.74-acre lot, offering ample room for gardening, outdoor activities, or future expansion. The home’s vinyl siding and multiple rooflines add character, while mature trees provide shade and seasonal beauty. A gravel driveway leads to a detached garage, giving the property functionality alongside its rural charm. The open space offers both privacy and potential in a city-close setting.
Living Area
The living area is finished in warm wood paneling, from walls to ceiling, creating a cozy, rustic ambiance. A ceiling fan centers the space, while a soft carpet adds comfort underfoot. The layout opens into the kitchen and adjacent hallway, providing easy movement throughout the home. Though dated in style, the room offers solid potential for updates while retaining its inviting, cabin-like character.
Kitchen
This L-shaped kitchen showcases custom wood cabinetry and a matching plank ceiling that extends across the room. Stainless steel appliances bring a modern touch, while solid-surface countertops and a neutral backsplash add functionality. A wide three-pane window over the sink brings in light and offers a backyard view. The kitchen’s warm tones and practical layout make it a strong foundation for future upgrades or restoration.
Small Bedroom
This modestly sized bedroom features neutral walls and carpet, offering a quiet, private space tucked near the back of the home. Built-in wall shelves provide storage or display options, while the closet offers room for everyday essentials. A single window lets in natural light, while white trim around doors and ceiling contrasts with the soft beige palette. With thoughtful updates, this room can serve as a nursery, study, or guest space.
Primary Bedroom
The primary bedroom is spacious with full wood-paneled walls and plush carpeting throughout. A set of double windows adds soft daylight to the room, while a central ceiling fixture provides warm ambient light. Connected to an en-suite bath and walk-in closet, this room is designed for comfort and convenience. With its generous footprint and classic paneling, the space invites personalization while maintaining its rustic charm.
Source: Coldwell Banker Advantage Via Zillow
4. 1922 Cottage Revival in Winston-Salem
Built-in 1922, this charming one-story Cottage Revival home has undergone a near-complete renovation. Listed at $195,000, it offers 1,330 square feet of updated living space on a 0.16-acre lot. Improvements include a new roof, electrical, plumbing, HVAC, vinyl siding, flooring, and drywall. Granite countertops, brand-new cabinetry, and stainless steel appliances modernize the interior. With a fenced backyard, detached garage, and classic curb appeal, this home blends history with move-in-ready comfort.
Where is Winston-Salem?
Winston-Salem is located in central North Carolina’s Piedmont Triad region. Once a hub for tobacco and textiles, the city is now known for its thriving arts scene, historic Moravian roots, and esteemed institutions like Wake Forest University. Situated near Greensboro and High Point, it offers cultural landmarks, restored neighborhoods, and ample green space. The city’s blend of history and innovation makes it an ideal place to live, work, and explore.
Front Porch
The front porch offers a tidy welcome with its iron railings, neutral siding, and freshly painted brick foundation. A concrete path leads to dual steps and a covered entry framed by crisp white trim. Overhead lighting adds functionality, while large shade trees frame the view. This classic Southern entryway blends historic character with modern restoration for a warm, polished first impression.
Living Room
This open and airy living room features soft green walls, wide plank laminate flooring, and a modern ceiling fan. A large window fills the space with natural light, offering a view of the front yard. The room’s clean layout flows effortlessly into the adjacent hallway, making it a versatile area for lounging or entertaining. Its updated finish balances a contemporary palette with traditional architectural simplicity.
Dining Room
The dining room is framed by smooth sage-colored walls and recessed lighting, with durable wood-look floors extending throughout. A wide doorway connects it to the adjacent living room, while a large side window brightens the space. With its neutral tones and central location, this flexible area is ideal for hosting meals or transitioning into a multi-use family zone. Its thoughtful updates create a fresh, timeless feel.
Kitchen
The kitchen has been fully reimagined with natural wood cabinetry, sleek granite countertops, and modern stainless steel appliances. A deep under-mount sink sits beneath twin windows, providing a lovely backyard view and ample daylight. Matte black fixtures and a stylish pendant light add a modern edge. Withan efficient layout and high-quality finishes, this space offers functionality and elegance for everyday cooking and entertaining.
Bedroom
This bright bedroom features warm-toned laminate flooring and soft green walls, accented by crisp white trim. Two large windows bring in abundant natural light, offering views of the neighborhood’s tree-lined streets. A ceiling fan above adds comfort, while the spacious layout allows for flexible furniture arrangement. Peaceful and private, this room serves as a restful retreat within the home’s thoughtfully updated interior.
Source: Atlas Realty Team Via Zillow