Vintage homes for sale & real estate in 27106, NC

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FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
Welcome to 4660 Tobacco Street! This cute and quaint 2-bedroom, 1-bath home offers a great opportunity for a first-time homebuyer or investor looking to add an income-producing property to their portfolio. Conveniently located near University Parkway, with quick access to Downtown Winston-Salem and US Highway 52, this home provides accessibility to many areas of the city. Previously occupied, this property has served as an income-producing rental and offers plenty of potential for its next owner. Whether you’re looking to add your own personal touches and make it home or explore its investment potential, this property is worth a look. The seller is motivated, and the property is price

$150,000

2 beds1 bath877 sq ft

4660 Tobacco St, Winston Salem, NC 27106

0.3 acre lot • Built 1955 • Listed 4 days

FOR SALE BY OWNER

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
Great opportunity in Buena Vista near Forsyth Country Club in Winston Salem. Nice, quiet neighborhood close to shopping, schools and both hospitals. With a park and walking path within walking distance Mid century Modern ranch style home with 3 Bedrooms, 3 Full Baths, Sunroom, Formal Living Room, and Dining room 2,600+/- sq. Solid concrete construction. Beautiful stone fireplace with Gas logs. With almost an acre, the yard is a hidden oasis in the city, with Outdoor courtyard and grill area. Large mature magnolia trees. Perfect set-up and plenty of room to install pool, cabana or other outdoor area.

$700,000

3 beds3 baths2,588 sq ft

730 Yorkshire Rd, Winston Salem, NC 27106

Built 1956 • Listed 12 days

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
Motivated seller! Your search ends here! Welcome to 3915 Avera, a unique ranch home in the heart of Winston-Salem. The spacious, open living room features beautiful LVP flooring and a painted brick fireplace, flowing into the dining area and fully updated kitchen with stainless appliances, soft-close cabinetry, and instant hot water. Enjoy the HUGE, fully fenced backyard, perfect for entertaining or creating your own oasis. Two-car rear-entry garage plus a huge parking pad add convenience and plenty of parking. Don’t miss this one—schedule your showing today!

$279,900

3 beds2 baths1,855 sq ft

3915 Avera Ave, Winston Salem, NC 27106

Open living room • Unique ranch home • Stainless appliances

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
Ranch Style Home has approx. 2200 sq ft. 3 spacious bedrooms and 2 full bathrooms, A Great Room, Dining Room Combo, Living Room with fireplace. Large windows to give extra light in home. Eat in Kitchen with Stainless steel appliances, Needs new refrigerator. Flooring is Wood, tile and carpet. Full Basement with epoxy floor and Washer and Dryer connections. Patio and Large fence in back yard with a place for a garden and more. Home needs some TLC and is BEING SOLD AS IS. Close to shopping and schools. A must see. Call for Appointment .

$285,000

3 beds2 baths2,125 sq ft

3841 Avera Ave, Winston Salem, NC 27106

Eat in kitchen • Full basement • Great room

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
Welcome to 2921 Bittersweet Road, offering space, flexibility, and outdoor enjoyment on approximately 1.05 acres. This property features a fenced backyard and an above-ground pool, patio space and a pallet deck creating the perfect setting for relaxing, entertaining, gardening, pets, or outdoor activities. Inside, you'll find comfortable living spaces with a functional layout and abundant natural light. The kitchen offers ample workspace and storage, and all appliances convey, making your move even easier. Upstairs bedrooms with 6'10 ceilings. An unfinished basement provides excellent storage and endless possibilities for a workshop, hobby space, home gym, or future expansion. The expansive

$274,900

4 beds2 baths1,719 sq ft

2921 Bittersweet Rd, Winston Salem, NC 27106

Expansive lot • Unfinished basement • Ample workspace

Property at 5275 Reynolda Rd, Winston Salem, NC 27106, 3 beds, 2 baths

$369,900

3 beds2 baths2,257 sq ft

5275 Reynolda Rd, Winston Salem, NC 27106

Property at 817 Clovelly Rd, Winston Salem, NC 27106, 3 beds, 3.5 baths

$550,000

3 beds3.5 baths2,901 sq ft

817 Clovelly Rd, Winston Salem, NC 27106

Property at 5441 Robinhood Rd, Winston Salem, NC 27106, 2 beds, 1 bath

$205,000

2 beds1 bath1,104 sq ft

5441 Robinhood Rd, Winston Salem, NC 27106

Property at 1039 Kenleigh Cir, Winston Salem, NC 27106, 4 beds, 3.5 baths

$795,900

4 beds3.5 baths3,197 sq ft

1039 Kenleigh Cir, Winston Salem, NC 27106

Property at 5150 Williamsburg Rd, Winston Salem, NC 27106, 3 beds, 1.5 baths

$240,000

3 beds1.5 baths1,359 sq ft

5150 Williamsburg Rd, Winston Salem, NC 27106

Property at 3563 Milhaven Rd, Winston Salem, NC 27106, 3 beds, 2 baths

$479,900

3 beds2 baths2,571 sq ft

3563 Milhaven Rd, Winston Salem, NC 27106

Property at 2832 Kensington Rd, Winston Salem, NC 27106, 4 beds, 3 baths

$634,000

4 beds3 baths2,720 sq ft

2832 Kensington Rd, Winston Salem, NC 27106

Property at 1023 Kearns Ave, Winston Salem, NC 27106, 5 beds, 2 baths

$529,900

5 beds2 baths1,989 sq ft

1023 Kearns Ave, Winston Salem, NC 27106

Property at 2701 Tudor Rd, Winston Salem, NC 27106, 4 beds, 3.5 baths

$699,000

4 beds3.5 baths2,701 sq ft

2701 Tudor Rd, Winston Salem, NC 27106

Property at 3743 Crosland Rd, Winston Salem, NC 27106, 4 beds, 2 baths

$299,900

4 beds2 baths2,044 sq ft

3743 Crosland Rd, Winston Salem, NC 27106

Property at 3340 York Rd, Winston Salem, NC 27106, 4 beds, 3.5 baths

$599,900

4 beds3.5 baths3,364 sq ft

3340 York Rd, Winston Salem, NC 27106

Property at 3759 Reynolda Rd, Winston Salem, NC 27106, 3 beds, 1 bath

$250,000

Land2.06 acres (lot)

3759 Reynolda Rd, Winston Salem, NC 27106

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NEW 26 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
Charming 2-Bedroom Home with Fenced Yard in Winston-Salem Welcome home to 1011 Manly St. in Winston-Salem, NC * * ! This inviting * * 2-bedroom, 1-bathroom home * * offers comfortable living with a practical layout and easy-to-maintain finishes. Inside, you’ll find LVP flooring throughout, providing a clean, modern look while making everyday maintenance a breeze. The home offers two comfortable bedrooms, a full bathroom, and inviting living spaces perfect for relaxing or entertaining. Step outside and enjoy the spacious back Yard, providing a private outdoor space for pets, gardening, entertaining, or simply enjoying some fresh air. Whether your looking for your next home or a

$129,900

2 beds1 bath680 sq ft

1011 Manly St, Winston Salem, NC 27105

Fenced yard • Spacious back yard • Lvp flooring

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
Welcome to 812 Holland Street, a beautifully restored 1930’s home nestled in the historic West End within walking distance to Granville Park and just minutes from downtown Winston-Salem, Old Salem, shopping, dining and hospitals. This home has a brand new air conditioning system, all new windows, new bathroom tile, refinished hardwood floors and a fresh coat of paint that brightens every room. Upstairs there is a spacious bedroom and loft space adorned in knotty pine. Outside enjoy the covered front porch or the shady back yard that includes a convenient storage shed. All move-in ready. Schedule your showing today!

$325,000

3 beds1 bath1,358 sq ft

812 Holland St, Winston Salem, NC 27101

Fresh coat of paint • Historic west end • Spacious bedroom

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
Opportunity knocks at this cute brick ranch on Glenn Ave. It features a covered porch, newer windows and storm door, hardwoods in the living room and bedrooms and plenty of space in the basement for additional gathering space. The main level bath has a walk in shower for ease of use. HVAC was installed by Webb Heating and Air and paperwork is onsite.

$99,875

2 beds1 bath1,130 sq ft

2839 N Glenn Ave, Winston Salem, NC 27105

Covered porch • Storm door • Newer windows

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
Approved NO-L Zoning! Standalone Turnkey Commercial Conversion on High-Traffic Rd. Exceptional exposure and flexible layout ideal for care home, private practice, law firm, or live-work professional. This standalone brick property features an absolute turnkey; accessible ramp leading directly from the rear parking zone to the front entrance. Inside boasts a grand reception/waiting lounge with access to a restroom, 3 sprawling executive office suites, a supply room, a dedicated conference room, full kitchen with storage pantry, and a second private full bath. Features a rare self-contained wing with independent exterior street access—perfect for corporate subleasing or passive rent inc

$495,000

3 beds2 baths1,643 sq ft

3606 Country Club Rd, Winston Salem, NC 27104

Full kitchen • Self-contained wing • No-l zoning

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
This classic 1920s home stands tall in the BV-West Highlands neighborhood, exuding historic charm & comfort inside & out! All the details have been well-preserved along w/ the classic features-tall ceilings, warm wood floors, picture moulding & more. The main level boasts a large living room w/ decorative FP, separate dining room w/ large windows & the cutest eat-in kitchen giving English cottage vibes. The covered porch beckons w/ its gorgeous slate tile floor & beadboard finishes-enjoy all the seasons here! A wonderful layout awaits upstairs w/ a spacious primary bedroom & private ensuite bath w/ a gorgeous basketweave tile floor & pink tile accen

$410,000

3 beds2.5 baths2,172 sq ft

1525 Cloverdale Ave, Winston Salem, NC 27104

Covered porch • Separate dining room • Paved driveway

ABOUT THIS HOME
Vintage Home for sale in 27106, NC:
Step back in time with this charming brick home built in 1957 offering a glimpse of its original character and craftsmanship. Featuring 2 bedrooms and 2 bathrooms, this home is ready for someone with vision to bring their ideas to life. A standout feature is the large detached work shed offering excellent space for a workshop, hobbies, projects, or additional storage. A second smaller shed provides even more space for belongings. With its classic brick exterior, spacious lot, and original condition, this property presents an opportunity to create a home that truly reflects your style while preserving its timeless charm. Bring your vision and make this classic your own!

$240,000

2 beds2 baths950 sq ft

941 Brownwood Dr, Winston Salem, NC 27105

Detached work shed • Spacious lot • Brick home

Property at 1720 Elizabeth Ave, Winston Salem, NC 27103, 3 beds, 2 baths

$375,000

3 beds2 baths1,513 sq ft

1720 Elizabeth Ave, Winston Salem, NC 27103

Property at 1409 W 4th St, Winston Salem, NC 27101, 5 beds, 4 baths

$205,000

5 beds4 baths3,652 sq ft

1409 W 4th St, Winston Salem, NC 27101

Property at 5600 Germanton Rd, Winston Salem, NC 27105, 3 beds, 2 baths

$290,000

3 beds2 baths2,042 sq ft

5600 Germanton Rd, Winston Salem, NC 27105

Property at 920 Bellview St, Winston Salem, NC 27103, 3 beds, 2 baths

$320,000

3 beds2 baths1,392 sq ft

920 Bellview St, Winston Salem, NC 27103

Property at 1445 Underwood Ave, Winston Salem, NC 27105, 2 beds, 1 bath

$189,900

2 beds1 bath860 sq ft

1445 Underwood Ave, Winston Salem, NC 27105

Property at 1224 Glade St, Winston Salem, NC 27101, 3 beds, 2.5 baths

$785,000

3 beds2.5 baths2,858 sq ft

1224 Glade St, Winston Salem, NC 27101

Property at 708 Hudson St, Winston Salem, NC 27105, 4 beds, 2 baths

$299,900

4 beds2 baths1,789 sq ft

708 Hudson St, Winston Salem, NC 27105

Property at 331 Burkewood Dr, Winston Salem, NC 27104, 2 beds, 2 baths

$322,000

2 beds2 baths1,428 sq ft

331 Burkewood Dr, Winston Salem, NC 27104

Property at 803 S Main St, Winston Salem, NC 27101, 14 beds, 14.5 baths

$1,295,000

14 beds14.5 baths6,027 sq ft

803 S Main St, Winston Salem, NC 27101

Property at 911 Taft St, Winston Salem, NC 27105, 2 beds, 1 bath

$119,900

2 beds1 bath639 sq ft

911 Taft St, Winston Salem, NC 27105

Property at 2824 Glenn Ave, Winston Salem, NC 27105, 4 beds, 2 baths

$149,900

4 beds2 baths1,810 sq ft

2824 Glenn Ave, Winston Salem, NC 27105

Property at 717 Magnolia St, Winston Salem, NC 27103, 2 beds, 1 bath

$239,000

2 beds1 bath842 sq ft

717 Magnolia St, Winston Salem, NC 27103

Property at 520 Gales Ave, Winston Salem, NC 27103, 3 beds, 2 baths

$315,000

3 beds2 baths1,520 sq ft

520 Gales Ave, Winston Salem, NC 27103

Property at 419 S Sunset Dr, Winston Salem, NC 27103, 3 beds, 1 bath

$290,000

3 beds1 bath1,431 sq ft

419 S Sunset Dr, Winston Salem, NC 27103

Based on information submitted to the MLS GRID as of Sun Oct 04 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in 27106

There are currently 17 vintage homes for sale in 27106 at a median listing price of $360K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 27106 stay on the market for 55 days and receive 1 offers. This map is refreshed with the newest listings in 27106 every 15 minutes.

In the past month, 50 homes have been sold in 27106. In addition to houses in 27106, there were also 37 condos, 17 townhouses, and 1 multi-family unit for sale in 27106 last month. 27106 is a not walkable zip code in North Carolina with a Walk Score of 19. 27106 is home to approximately 42,751 people and 15,808 jobs. Find your dream home in 27106 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 27106 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 27106. If you're looking to sell your home in the 27106 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 27106 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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