Vintage homes for sale & real estate in Winston-Salem, NC

178 homes

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ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Discover the potential in this charming two-bedroom, one-bath home located at 3726 North Hampton Drive in Winston-Salem. Ideal for investors or anyone looking to add to their rental portfolio. The home features a comfortable floor plan with an inviting living area, a bright kitchen, and ample yard space. What makes this listing even more appealing is the vacant lot next door, included in the sale. With a combined total of 0.37 acres (home + lot = 0.26 acres vacant land + 0.11 acres for the main parcel), there’s plenty of room for expansion, additional parking, or future development.

$230,000

2 beds1 bath— sq ft

3726 Northampton Dr, Winston Salem, NC 27105

Room for expansion • Ample yard space • 4,791 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Charming brick ranch in quiet neighborhood. Kitchen with granite countertops, refrigerator and microwave purchased 7/24, lots of unexplored potential with house and yard. Basement offers flex spaces for work or larger gatherings, seller says it stays dry. Backyard is flat, excellent for playing games or growing a garden. Circular drive which for allows several off street parking spaces.

$254,900

3 beds2 baths1,296 sq ft

200 Blake St, Winston Salem, NC 27104

Flat backyard • Circular drive • Flex spaces

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Ideal for those looking for a home in a prime location, this property offers a fantastic opportunity for renovation and customization. With three bedrooms and one bathroom, the layout is both practical and efficient. The attic provides dual heating and air conditioning units with abundant storage. The expansive yard has ample space for gardening, entertaining, and simply enjoying the outdoors. Located in a convenient Winston Salem area, near University Parkway and Reynolda Road, this home provides classic appeal with a promising investment opportunity. The seller will consider concessions toward the buyer closing costs. Ask the listing agent about available seller credits.

$200,000

3 beds1 bath1,008 sq ft

4620 Miller Rd, Winston Salem, NC 27106

Prime location • Abundant storage • 0.33 acre lot

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Excellent Investment Opportunity! Charming 3-bedroom, 1-bath home built in 1940, offering timeless character and strong investment potential. This property features a functional layout and solid structure, ideal for renovation or long-term rental. Currently occupied, providing an immediate income stream for investors. Conveniently located near local amenities, schools, and major thoroughfares. Property to be sold as-is. Showing Instructions: Property is occupied. Please email proof of funds to revecasells@gmail.com prior to scheduling showings. Photos shown are from before move-in. Please note — the condition of the home may have changed since these photos were taken.

$130,000

3 beds1 bath1,022 sq ft

530 Barbara Jane Ave, Winston Salem, NC 27101

Functional layout • Solid structure • Conveniently located

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Charming house; with a great lot , ideal for entertaining or just having the kids over; New metal Roof; New Gutters; New paved Driveway ; New Back door; Washer and Dryer Stay; Refrigerator and slide in range as well. New indoor painting; New Light Fixtures; NEw insolation; New Front Windows; Near commercial center (Walmart); Great storage with power in it. Make this dream house yours!!! Furniture in te house was added via AI.

$268,500

2 beds2 baths1,124 sq ft

1414 Jonestown Rd, Winston Salem, NC 27103

Metal roof • New back door • New indoor painting

Property at 1346 Robbins Rd, Winston Salem, NC 27107, 2 beds, 1 bath

$240,000

2 beds1 bath1,350 sq ft

1346 Robbins Rd, Winston Salem, NC 27107

Property at 1608 Sharon Rd, Winston Salem, NC 27103, 5 beds, 3 baths

$499,000

5 beds3 baths3,390 sq ft

1608 Sharon Rd, Winston Salem, NC 27103

Property at 2907 NE Bon Air Ave, Winston Salem, NC 27105, 5 beds, 2 baths

$209,000

5 beds2 baths1,858 sq ft

2907 NE Bon Air Ave, Winston Salem, NC 27105

Property at 1633 Emerald St, Winston Salem, NC 27105, 2 beds, 2 baths

$194,900

2 beds2 baths946 sq ft

1633 Emerald St, Winston Salem, NC 27105

Property at 4507 Northampton Dr, Winston Salem, NC 27105, 4 beds, 2 baths

$259,900

4 beds2 baths1,681 sq ft

4507 Northampton Dr, Winston Salem, NC 27105

Property at 3555 Transou Rd, Pfafftown, NC 27040, 3 beds, 2 baths

$300,000

3 beds2 baths1,541 sq ft

3555 Transou Rd, Pfafftown, NC 27040

Property at 411 Holiday St, Winston Salem, NC 27104, 3 beds, 2 baths

$364,900

3 beds2 baths1,152 sq ft

411 Holiday St, Winston Salem, NC 27104

Property at 2124 Konnoak View Dr, Winston Salem, NC 27127, 3 beds, 1 bath

$284,500

3 beds1 bath1,375 sq ft

2124 Konnoak View Dr, Winston Salem, NC 27127

Property at 1406 Chelsea St, Winston Salem, NC 27103, 3 beds, 1 bath

$234,000

3 beds1 bath900 sq ft

1406 Chelsea St, Winston Salem, NC 27103

Property at 101 N Chestnut St #13, Winston Salem, NC 27101, 1 bed, 1 bath

$205,000

1 bed1 bath592 sq ft

101 N Chestnut St #13, Winston Salem, NC 27101

Property at 929 Hawthorne Rd, Winston Salem, NC 27103, 4 beds, 3 baths

$575,000

4 beds3 baths2,110 sq ft

929 Hawthorne Rd, Winston Salem, NC 27103

Property at 5010 N Cherry St, Winston Salem, NC 27101, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths2,152 sq ft

5010 N Cherry St, Winston Salem, NC 27101

Property at 125 Brevard St, Winston Salem, NC 27101, 2 beds, 1 bath

$182,900

2 beds1 bath989 sq ft

125 Brevard St, Winston Salem, NC 27101

Property at 1426 Thurmond St, Winston Salem, NC 27105, 4 beds, 1.5 baths

$229,900

4 beds1.5 baths1,080 sq ft

1426 Thurmond St, Winston Salem, NC 27105

Property at 412 Corona St, Winston Salem, NC 27103, 5 beds, 2.5 baths

$425,000

5 beds2.5 baths2,671 sq ft

412 Corona St, Winston Salem, NC 27103

Property at 1 W 5th St #301, Winston Salem, NC 27101, 3 beds, 2 baths

$699,900

3 beds2 baths2,462 sq ft

1 W 5th St #301, Winston Salem, NC 27101

Property at 1280 Cloister Dr, Winston Salem, NC 27127, 3 beds, 1 bath

$211,960

3 beds1 bath1,087 sq ft

1280 Cloister Dr, Winston Salem, NC 27127

Property at 613 N Jackson Ave, Winston Salem, NC 27101, 3 beds, 1 bath

$140,500

3 beds1 bath1,330 sq ft

613 N Jackson Ave, Winston Salem, NC 27101

Property at 4535 Main St, Winston Salem, NC 27127, 3 beds, 1 bath

$341,300

3 beds1 bath1,270 sq ft

4535 Main St, Winston Salem, NC 27127

Property at 2435 Hoyt St, Winston Salem, NC 27103, 3 beds, 2.5 baths

$469,000

3 beds2.5 baths1,954 sq ft

2435 Hoyt St, Winston Salem, NC 27103

Property at 40 Evergreen Dr, Winston Salem, NC 27106, 3 beds, 1.5 baths

$255,000

3 beds1.5 baths1,180 sq ft

40 Evergreen Dr, Winston Salem, NC 27106

Property at 1110 Magnolia St, Winston Salem, NC 27103, 3 beds, 2 baths

$357,000

3 beds2 baths1,604 sq ft

1110 Magnolia St, Winston Salem, NC 27103

Property at 1823,1827, & 1831 First St W, Winston Salem, NC 27104

$850,000

— beds— baths— sq ft

1823,1827, & 1831 First St W, Winston Salem, NC 27104

Property at 1432 Miller St, Winston Salem, NC 27103, 2 beds, 1 bath

$279,900

2 beds1 bath1,090 sq ft

1432 Miller St, Winston Salem, NC 27103

Property at 2360 N Patterson Ave, Winston Salem, NC 27105, 3 beds, 1 bath

$125,000

3 beds1 bath1,266 sq ft

2360 N Patterson Ave, Winston Salem, NC 27105

Property at 2325 N Glenn Ave, Winston Salem, NC 27105, 3 beds, 2 baths

$199,900

3 beds2 baths1,131 sq ft

2325 N Glenn Ave, Winston Salem, NC 27105

Property at 434 Pennsylvania Ave, Winston Salem, NC 27104, 3 beds, 2 baths

$440,000

3 beds2 baths1,631 sq ft

434 Pennsylvania Ave, Winston Salem, NC 27104

Property at 1614 Granite St, Winston Salem, NC 27107, 3 beds, 2 baths

$200,000

3 beds2 baths1,516 sq ft

1614 Granite St, Winston Salem, NC 27107

Property at 4511 June Ave, Winston Salem, NC 27106, 3 beds, 1 bath

$195,000

3 beds1 bath1,357 sq ft

4511 June Ave, Winston Salem, NC 27106

Property at 2708 Bon Air Ave, Winston Salem, NC 27105, 3 beds, 1 bath

$169,000

3 beds1 bath1,206 sq ft

2708 Bon Air Ave, Winston Salem, NC 27105

Property at 615 Corona St, Winston Salem, NC 27103, 2 beds, 1 bath

$239,000

2 beds1 bath908 sq ft

615 Corona St, Winston Salem, NC 27103

Property at 4433 Ogburn Ave, Winston Salem, NC 27105, 3 beds, 2 baths

$279,000

3 beds2 baths1,633 sq ft

4433 Ogburn Ave, Winston Salem, NC 27105

Property at 1514 N Patterson Ave, Winston Salem, NC 27105, 3 beds, 1.5 baths

$185,000

3 beds1.5 baths1,291 sq ft

1514 N Patterson Ave, Winston Salem, NC 27105

Property at 2242 Hollyrood St, Winston Salem, NC 27127, 2 beds, 1 bath

$194,900

2 beds1 bath889 sq ft

2242 Hollyrood St, Winston Salem, NC 27127

Property at 2055 W Academy St, Winston Salem, NC 27103

$325,000

— beds— baths— sq ft

2055 W Academy St, Winston Salem, NC 27103

Property at 4720 Old Rural Hall Rd, Winston Salem, NC 27105, 5 beds, 3 baths

$375,000

5 beds3 baths2,650 sq ft

4720 Old Rural Hall Rd, Winston Salem, NC 27105

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Based on information submitted to the MLS GRID as of Sun Nov 30 2025. 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 Winston-Salem

There are currently 178 vintage homes for sale in Winston-Salem at a median listing price of $304K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winston-Salem stay on the market for 52 days and receive 3 offers. Popular neighborhoods include Old Sherwood Forest, Ardmore, West End, Southwest Meridian, and Buena Vista. This map is refreshed with the newest listings in Winston-Salem every 15 minutes.

In the past month, 260 homes have been sold in Winston-Salem. In addition to houses in Winston-Salem, there were also 90 condos, 87 townhouses, and 5 multi-family units for sale in Winston-Salem last month. Winston-Salem is a not walkable city in North Carolina with a Walk Score of 22. Winston-Salem is home to approximately 228,366 people and 143,927 jobs. Find your dream home in Winston-Salem 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 Winston-Salem are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winston-Salem. Our Winston-Salem real estate stats and trends will give you more information about home buying and selling trends in Winston-Salem. If you're looking to sell your home in the Winston-Salem area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winston-Salem with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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