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

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ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
5745 Reynolda Rd offers a versatile 3.79± acre property with dual zoning—HB (Highway Business) along Reynolda frontage and RS-9 for residential depth. Improvements include a ranch-style home with basement, attached garage, and a separate commercial garage structure. The HB district supports retail, office, and service uses benefiting from high traffic visibility, while RS-9 accommodates single-family residential or buffering/open space. Highest and best use aligns with mixed income generation—maintaining residential rentals while redeveloping the HB portion for medical, office, or small-scale retail. Assemblage with adjacent HB parcels could further enhance redevelopment

$550,000

4 beds2 baths2,631 sq ft

5755 Reynolda Rd, Winston-salem, NC 27106

Ranch style home • Dual zoning • 3.79 acre lot

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Priced reduced to below tax value! Beautiful older home on 1-1/2 acres in great location. Circular gravel drive goes around house. Lovely paneling and built-ins. Refrigerators stay. Currently bedroom 4 has small kitchenette (could be removed) such that upstairs space could be used as in-law suite or for grown children; possible rental (confirm with zoning), has own outside entrance. Square footage does not include sun room at back with original wood flooring from barn, air conditioning unit but no heat.

$299,900

4 beds2 baths2,256 sq ft

2281 Olivet Church Rd, Winston Salem, NC 27106

In-law suite • Small kitchenette • Outside entrance

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Recent Price Improvement!!! Are you looking for an investment property in highly sought after downtown Winston Salem? Look no further than 927 Apple St. Walking distance to downtown, Truist Stadium, coffee shops, bakeries, restaurants and Carolina University. Currently leased with 3 great tenants in place: 2 Occupied En-suite bedrooms at $750/month each (1Bdrm, 1 Bath) 1 En-suite bedroom transferring vacant (projected $850/month) 1 Occupied Guest suite rented long-term at $1,200/month (2Bdrm 1 Bath) Total current rent: $2,700/month, with immediate upside to $3,550/month once fully occupied. Leases are currently month to month. Several recent updates including roof, windows, and fresh

$320,000

5 beds4 baths2,130 sq ft

927 Apple St, Winston Salem, NC 27101

Spacious porch • Ample rear parking • 8,276 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
SELLER IS OFFERING A $10,000 BUYER CONCESSION!! Don’t miss this beautiful 3-bedroom, 2-bath home located less than a mile from the prestigious Forsyth Country Club and directly across from Hathaway Park. Step inside to a bright, open floor plan featuring spacious living areas designed for comfort and functionality. The home also includes a full-size basement with over 800 square feet, perfect for entertaining guests, creating a home theater, or setting up your dream recreation space. Enjoy the convenience of nearby parks, shopping, and dining, all while nestled in a convenient Winston-Salem neighborhood known for its charm and accessibility. Experience the perfect blend of location, s

$349,000

3 beds2 baths2,093 sq ft

318 Anita Dr, Winston Salem, NC 27104

New floors • Updated baths • Large basement

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Perfect Ardmore location with outstanding short term rental history totaling $65,000 in 2024. The finished basement provides a full kitchen, bathroom, bedroom, and living space, along with separate parking and a private entrance—ideal for an in-law suite or rental opportunity. Newer roof and HVAC! Beautifully updated kitchen with white shaker cabinets, quartz countertops, backsplash, under-cabinet lighting, and a built-in pantry. The spacious primary suite includes a walk-in closet and a stunning bathroom. Outside, enjoy a fenced backyard with two storage buildings. Conveniently located near shopping, restaurants, hospitals, and local parks. This one is not to be missed!

$525,000

4 beds3 baths2,287 sq ft

700 Magnolia St, Winston Salem, NC 27103

Built-in pantry • Newer roof • Finished basement

Property at 3351 Emory Dr, Winston Salem, NC 27103, 2 beds, 1 bath

$195,000

2 beds1 bath725 sq ft

3351 Emory Dr, Winston Salem, NC 27103

Property at 638 Mccreary St, Winston Salem, NC 27105, 2 beds, 1 bath

$159,900

2 beds1 bath961 sq ft

638 Mccreary St, Winston Salem, NC 27105

Property at 940 N Peace Haven Rd, Winston Salem, NC 27104, 3 beds, 2 baths

$359,900

3 beds2 baths2,761 sq ft

940 N Peace Haven Rd, Winston Salem, NC 27104

Property at 4847 Dippen Rd, Winston Salem, NC 27105, 3 beds, 2.5 baths

$265,000

3 beds2.5 baths2,122 sq ft

4847 Dippen Rd, Winston Salem, NC 27105

Property at 814 Cameron Ave, Winston Salem, NC 27101, 3 beds, 1.5 baths

$165,000

3 beds1.5 baths2,060 sq ft

814 Cameron Ave, Winston Salem, NC 27101

Property at 106 Azalea Dr, Winston Salem, NC 27105, 3 beds, 1 bath

$230,000

3 beds1 bath1,247 sq ft

106 Azalea Dr, Winston Salem, NC 27105

Property at 3924 Avera Ave, Winston Salem, NC 27106, 3 beds, 2 baths

$249,500

3 beds2 baths1,434 sq ft

3924 Avera Ave, Winston Salem, NC 27106

Property at 4037 Hilda St, Winston Salem, NC 27104, 2 beds, 1 bath

$217,000

2 beds1 bath1,088 sq ft

4037 Hilda St, Winston Salem, NC 27104

Property at 844 Bethany Church Rd, Winston Salem, NC 27107, 3 beds, 2 baths

$475,000

3 beds2 baths1,984 sq ft

844 Bethany Church Rd, Winston Salem, NC 27107

Property at 3310 Staghorn Rd, Winston Salem, NC 27104, 3 beds, 2.5 baths

$399,900

3 beds2.5 baths2,333 sq ft

3310 Staghorn Rd, Winston Salem, NC 27104

Property at 3932 Lexwin Ave, Winston Salem, NC 27107, 2 beds, 1 bath

$231,900

2 beds1 bath917 sq ft

3932 Lexwin Ave, Winston Salem, NC 27107

Property at 1365 Reynolda Rd, Winston Salem, NC 27106, 3 beds, 2.5 baths

$719,900

3 beds2.5 baths2,870 sq ft

1365 Reynolda Rd, Winston Salem, NC 27106

Property at 1121 Rich Ave, Winston Salem, NC 27101, 3 beds, 2 baths

$214,000

3 beds2 baths1,835 sq ft

1121 Rich Ave, Winston Salem, NC 27101

Property at 2400 Jefferson Ave, Winston Salem, NC 27103, 3 beds, 2 baths

$436,500

3 beds2 baths1,665 sq ft

2400 Jefferson Ave, Winston Salem, NC 27103

Property at 4656 Walcott St, Winston Salem, NC 27106, 3 beds, 1.5 baths

$157,900

3 beds1.5 baths1,234 sq ft

4656 Walcott St, Winston Salem, NC 27106

Property at 1920 Robinhood Rd, Winston Salem, NC 27104, 3 beds, 4 baths

$649,900

3 beds4 baths2,207 sq ft

1920 Robinhood Rd, Winston Salem, NC 27104

Property at 800 Brent St, Winston Salem, NC 27103, 5 beds, 2 baths

$444,900

5 beds2 baths2,086 sq ft

800 Brent St, Winston Salem, NC 27103

Property at 1433 W 4th St, Winston Salem, NC 27101, 4 beds, 2 baths

$299,950

4 beds2 baths1,914 sq ft

1433 W 4th St, Winston Salem, NC 27101

Property at 2336 Montrose Ave, Winston Salem, NC 27105, 3 beds, 1 bath

$199,900

3 beds1 bath1,372 sq ft

2336 Montrose Ave, Winston Salem, NC 27105

Property at 168 Oak Summit Rd, Winston Salem, NC 27105, 3 beds, 3 baths

$352,999

3 beds3 baths3,711 sq ft

168 Oak Summit Rd, Winston Salem, NC 27105

Property at 4798 Cherry St, Winston Salem, NC 27105, 4 beds, 2 baths

$348,000

4 beds2 baths2,008 sq ft

4798 Cherry St, Winston Salem, NC 27105

Property at 1709 N Jackson Ave, Winston Salem, NC 27105, 3 beds, 1 bath

$240,000

3 beds1 bath2,204 sq ft

1709 N Jackson Ave, Winston Salem, NC 27105

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

$199,500

4 beds1.5 baths1,134 sq ft

1457 Douglas St, Winston Salem, NC 27105

Property at 4372 Oak Ridge Dr, Winston Salem, NC 27105, 3 beds, 1 bath

$120,000

3 beds1 bath1,051 sq ft

4372 Oak Ridge Dr, Winston Salem, NC 27105

Property at 315 N Spruce St #307, Winston Salem, NC 27101, 1 bed, 1.5 baths

$229,000

1 bed1.5 baths939 sq ft

315 N Spruce St #307, Winston Salem, NC 27101

Property at 2800 Loch Dr, Winston Salem, NC 27106, 3 beds, 2 baths

$300,000

3 beds2 baths2,124 sq ft

2800 Loch Dr, Winston Salem, NC 27106

Property at 4065 Leo St, Winston Salem, NC 27105, 3 beds, 2 baths

$239,900

3 beds2 baths1,183 sq ft

4065 Leo St, Winston Salem, NC 27105

Property at 1950 Butler St, Winston Salem, NC 27107, 2 beds, 1 bath

$234,900

2 beds1 bath1,128 sq ft

1950 Butler St, Winston Salem, NC 27107

Property at 1401 Bretton St, Winston Salem, NC 27105, 6 beds, 3 baths

$249,000

6 beds3 baths2,963 sq ft

1401 Bretton St, Winston Salem, NC 27105

Property at 2841 Wesleyan Ln, Winston Salem, NC 27106, 3 beds, 2 baths

$389,000

3 beds2 baths1,817 sq ft

2841 Wesleyan Ln, Winston Salem, NC 27106

Property at 517 N Cameron Ave, Winston Salem, NC 27101, 4 beds, 2 baths

$160,000

4 beds2 baths1,753 sq ft

517 N Cameron Ave, Winston Salem, NC 27101

Property at 4613 Shattalon Dr, Winston Salem, NC 27106, 3 beds, 2 baths

$259,000

3 beds2 baths1,913 sq ft

4613 Shattalon Dr, Winston Salem, NC 27106

Property at 523 Summit St, Winston-salem, NC 27101, 5 beds, 4 baths

$990,000

5 beds4 baths4,763 sq ft

523 Summit St, Winston-salem, NC 27101

Property at 12387 Old Us Highway 52, Winston Salem, NC 27107, 2 beds, 2 baths

$207,400

2 beds2 baths1,220 sq ft

12387 Old Us Highway 52, Winston Salem, NC 27107

Property at 4420 Chebar Dr, Pfafftown, NC 27040, 3 beds, 2 baths

$279,900

3 beds2 baths1,425 sq ft

4420 Chebar Dr, Pfafftown, NC 27040

Property at 504 W Sprague St, Winston Salem, NC 27127, 5 beds, 3 baths

$450,000

5 beds3 baths2,264 sq ft

504 W Sprague St, Winston Salem, NC 27127

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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 177 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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