Vintage homes for sale & real estate in 27105, NC

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FOR SALE BY OWNER

ABOUT THIS HOME
Vintage Home for sale in 27105, NC:
Freshly updated, move in ready large family-friendly home. Inviting family room when you first walk in. 4 bedrooms with a laundry room off the master bedroom. Master bedroom has a private 1/2 bath. Home boasts 2 additional full bathrooms. Perfect for a busy family! Original hardwood floors. Recent updates include new Heating and Air unit, new wiring over entire home, new porch, and fresh interior paint. Spacious and private backyard. This home is a gem as your private residence or as a rental property.

$175,900

4 beds3 baths1,503 sq ft

2524 Ansonia St, Winston Salem, NC 27105

Laundry room • Private bath • Family room

ABOUT THIS HOME
Vintage Home for sale in 27105, NC:
Charming bungalow in the heart of Winston Salem! This 2 bedroom 1 bath home has been completely updated! This home features new luxury vinyl plank flooring throughtout, new kitchen cabinets & appliances and updated bathroom! you will love sitting on the back deck relaxing, overlooking the large back yard. This home is part of the CIty of Winston Salem Affordable Housing Development and buyers must qualify for the program. Agents see attachments for guidlines

$130,000

2 beds1 bath800 sq ft

2206 Dunbar St, Winston Salem, NC 27105

Large back yard • Back deck • 5,227 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in 27105, NC:
Solid brick home with room to spread out! This 3-bedroom, 3-bath home offers a flexible floor plan with plenty of living space. The main level features a spacious living room, kitchen, primary suite, and second bedroom with direct access to the screened porch. Upstairs you'll find an additional bedroom, full bath, second living area, and an additional cooking space, providing flexible space for guests, hobbies, or everyday living. The partially finished basement offers workshop space and abundant storage. Attached garage, natural gas heat, central air, and a convenient location just minutes from downtown, shopping, and US-52. Tenant occupied until end of Sept 2026. Appointment required.

$270,000

3 beds3 baths1,986 sq ft

2313 N Glenn Ave, Winston Salem, NC 27105

Workshop space • Flexible floor plan • Brick home

ABOUT THIS HOME
Vintage Home for sale in 27105, NC:
This inviting ranch with covered front porch offers an excellent opportunity for both first time homeowners and investors. Why pay rent when you can enjoy the benefits of homeownership for less. Investors have the opportunity to add an income-producing property to their rental portfolio. Currently non-owner occupied on a month-to-month lease at $1,250/month. Welcoming covered front porch adds charm and a great spot to relax. Maintenance free aluminum siding, Recent roof, AC 2024, and large backyard combined with the convenient location just minutes from shopping, dining, and quick access to major Winston-Salem corridors make this a must see! Comfortable, convenient, and full of potential -

$127,900

2 beds1 bath812 sq ft

4330 Ogburn Ave, Winston Salem, NC 27105

Covered front porch • Large backyard • Recent roof

SHORT SALE

ABOUT THIS HOME
Vintage Home for sale in 27105, NC:
Great opportunity for first-time buyer or investor. This 2 bedrooms, 2.5 baths, living room with fireplace, dining room, kitchen, and unfinished has been renovated with modern updates. The renovations include painting the exteror and interior, new flooring, modernizing bath rooms, and basement. Coveniently located to shops, restaurants, public transportation, downtown, and Wake Forest Unversity. NCHF Down Payment Assistance to qualified buyer.

$172,000

2 beds2.5 baths1,375 sq ft

2524 N Cherry St, Winston Salem, NC 27105

Modern updates • New flooring • 3,920 sq ft lot

Property at 5002 Cherry St, Winston Salem, NC 27105, 3 beds, 1 bath

$199,000

3 beds1 bath1,307 sq ft

5002 Cherry St, Winston Salem, NC 27105

Property at 31 25th St, Winston Salem, NC 27105, 3 beds, 1 bath

$135,000

3 beds1 bath1,008 sq ft

31 25th St, Winston Salem, NC 27105

Property at 1407 NE 22nd St, Winston Salem, NC 27105, 2 beds, 1 bath

$110,000

2 beds1 bath832 sq ft

1407 NE 22nd St, Winston Salem, NC 27105

Property at 5027 Old Rural Hall Rd, Winston Salem, NC 27105, 3 beds, 1 bath

$185,000

3 beds1 bath1,236 sq ft

5027 Old Rural Hall Rd, Winston Salem, NC 27105

Property at 454 24th St W, Winston Salem, NC 27105, 3 beds, 1 bath

$179,900

3 beds1 bath1,166 sq ft

454 24th St W, Winston Salem, NC 27105

Property at 5167 N Cherry St, Winston-salem, NC 27105, 3 beds, 1 bath

$235,000

3 beds1 bath1,305 sq ft

5167 N Cherry St, Winston-salem, NC 27105

Property at 1210 22nd St, Winston Salem, NC 27105, 2 beds, 1 bath

$105,000

2 beds1 bath832 sq ft

1210 22nd St, Winston Salem, NC 27105

Property at 1457 Douglas St, Winston Salem, NC 27105, 4 beds, 1.5 baths

$189,500

4 beds1.5 baths1,134 sq ft

1457 Douglas St, Winston Salem, NC 27105

Property at 938 Brownwood Dr, Winston Salem, NC 27105, 3 beds, 1 bath

$250,000

3 beds1 bath1,365 sq ft

938 Brownwood Dr, Winston Salem, NC 27105

Property at 1410 Old Hollow Rd, Winston Salem, NC 27105, 2 beds, 1 bath

$95,000

Land2.49 acres (lot)

1410 Old Hollow Rd, Winston Salem, NC 27105

Property at 1637 Sanford Dr, Winston Salem, NC 27105, 2 beds, 1 bath

$85,000

Land0.52 acre (lot)

1637 Sanford Dr, Winston Salem, NC 27105

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Based on information submitted to the MLS GRID as of Mon Oct 26 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 27105

There are currently 57 vintage homes for sale in 27105 at a median listing price of $230K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 27105 stay on the market for 60 days and receive 1 offers. This map is refreshed with the newest listings in 27105 every 15 minutes.

In the past month, 25 homes have been sold in 27105. In addition to houses in 27105, there were also 3 condos, 1 townhouse, and 2 multi-family units for sale in 27105 last month. Find your dream home in 27105 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 27105 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 27105. If you're looking to sell your home in the 27105 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 27105 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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