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

176 homes

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NEW 23 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Don’t miss out on this fantastic prime opportunity just a 5-minute walk from Wake Forest University! Discover this incredible classic ranch on a full unfinished basement offering you versatility and charm. Located in a sought-after area close to shopping, dining, and major highways, this property offers endless possibilities for homeowners or investors looking for additional rental income. — Sold As-Is - If you are looking for a home in a convenient location, with 3 bedrooms and one full bath, spacious family room, wooden kitchen cabinets, 2 decks and a patio, a full unfinished walkout basement with space for all your work hobbies with a fenced yard. Look no further! This could

$274,900

3 beds1 bath1,617 sq ft

1707 Brookwood Dr, Winston Salem, NC 27106

Fenced yard • Sought-after area • Close to dining

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Looking for land and space to ENJOY? This Charming 2 bedroom 1 bathroom home with a 2 car garage is conveniently located nearthe interstate for easy access to Winston Salem or south to Lexington. This home offers several outbuildings on 5.5 acres. Upstairs attic has been finished and offers bonus space to use, but not counted in square feet due to ceiling height. Come see all of the property and outbuildings to see how you can use this land and enjoy.

$299,000

2 beds1 bath1,288 sq ft

340 Jones Rd, Winston Salem, NC 27107

Finished attic • 5.5 acres • 5.5 acre lot

HOT HOME

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Welcome to 829 Sunset Dr in Ardmore—an updated, income-ready duplex-style home offering exceptional flexibility. Currently a successful short- and mid-term rental, this property features two fully separate living spaces, each with its own entrance, kitchen, laundry, and bath, plus an interior lockable door for use as one combined home. The upper level offers 2 bedrooms, 1 updated bath, hardwood floors, and a modern kitchen. The lower level includes 1 bedroom, 1 bath, a full kitchen, private laundry, and its own exterior entry—ideal for guests or tenants. With refreshed kitchens and baths, a dual-floor HVAC system, and classic Ardmore charm, this home is minutes from shopping, di

$249,900

3 beds2 baths1,383 sq ft

829 S Sunset Dr, Winston Salem, NC 27103

Refreshed kitchens • Income ready duplex • Private laundry

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Adorable cottage-style home in the heart of Ardmore! Enjoy mornings on the welcoming front porch and evenings on the spacious back deck overlooking a large, fully fenced backyard—perfect for pets, play, and outdoor gatherings. This charming home blends character with comfort. Just minutes from shopping, dining, hospitals, and parks. A rare Ardmore find with incredible charm and unbeatable location!

$299,000

3 beds2 baths1,364 sq ft

1043 Irving St, Winston Salem, NC 27103

Front porch • Back deck • Minutes from dining

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Great opportunity for first-time buyers or investors! This charming one-level home offers unbeatable convenience, located just minutes from Winston-Salem amenities with quick access to the beltway for easy commutes to Kernersville and Greensboro. This property also has a detached garage, perfect for a workshop or hobbies! Enjoy peace of mind with a new roof, and bring your vision—this property is being sold as-is, giving you the chance to make it your own. Perfect for anyone looking for value, potential, and a convenient location! Free appraisal or . 250% lender credit with seller's preferred lender! Agents, see agent only.

$225,000

3 beds1 bath2,052 sq ft

6101 Phelps Cir, Winston Salem, NC 27105

Convenient location • New roof • Detached garage

Property at 1456 Miller St, Winston Salem, NC 27103, 3 beds, 1 bath

$349,000

3 beds1 bath1,428 sq ft

1456 Miller St, Winston Salem, NC 27103

Property at 3937 Waddill St, Winston Salem, NC 27105, 3 beds, 1 bath

$225,000

3 beds1 bath1,396 sq ft

3937 Waddill St, Winston Salem, NC 27105

Property at 2062 K Court Ave, Winston Salem, NC 27105, 4 beds, 2 baths

$275,000

4 beds2 baths1,479 sq ft

2062 K Court Ave, Winston Salem, NC 27105

Property at 415 S Poplar St, Winston Salem, NC 27101, 4 beds, 4 baths

$350,000

4 beds4 baths2,014 sq ft

415 S Poplar St, Winston Salem, NC 27101

Property at 3632 Konnoak Dr, Winston Salem, NC 27127, 2 beds, 2 baths

$135,000

2 beds2 baths1,212 sq ft

3632 Konnoak Dr, Winston Salem, NC 27127

Property at 2828 N Glenn Ave, Winston Salem, NC 27105, 4 beds, 2 baths

$127,500

4 beds2 baths1,630 sq ft

2828 N Glenn Ave, Winston Salem, NC 27105

Property at 1020 W Kent Rd, Winston Salem, NC 27104, 6 beds, 7.5 baths

$1,800,000

6 beds7.5 baths6,619 sq ft

1020 W Kent Rd, Winston Salem, NC 27104

Property at 3627 Main St, Winston Salem, NC 27127, 2 beds, 1 bath

$167,500

2 beds1 bath870 sq ft

3627 Main St, Winston Salem, NC 27127

Property at 3014 Gilbert St, Winston Salem, NC 27107, 3 beds, 2 baths

$114,000

3 beds2 baths1,725 sq ft

3014 Gilbert St, Winston Salem, NC 27107

Property at 1421 Old Town Rd, Winston Salem, NC 27106, 4 beds, 2 baths

$298,000

4 beds2 baths2,090 sq ft

1421 Old Town Rd, Winston Salem, NC 27106

Property at 252 Lucerne Ln NW, Winston Salem, NC 27104, 3 beds, 3 baths

$569,900

3 beds3 baths2,345 sq ft

252 Lucerne Ln NW, Winston Salem, NC 27104

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 246 Piccadilly Dr, Winston Salem, NC 27104, 3 beds, 2 baths

$225,000

3 beds2 baths1,261 sq ft

246 Piccadilly Dr, Winston Salem, NC 27104

Property at 1469 Cherry St, Winston Salem, NC 27105, 3 beds, 2 baths

$197,000

3 beds2 baths1,056 sq ft

1469 Cherry St, Winston Salem, NC 27105

Property at 4630 Tobacco St, Winston Salem, NC 27106, 3 beds, 1 bath

$193,800

3 beds1 bath1,200 sq ft

4630 Tobacco St, Winston Salem, NC 27106

Property at 1101 Franklin St, Winston Salem, NC 27101, 8 beds, 2 baths

$194,900

8 beds2 baths2,916 sq ft

1101 Franklin St, Winston Salem, NC 27101

Property at 819 Madison Ave, Winston Salem, NC 27103, 4 beds, 2 baths

$320,000

4 beds2 baths1,728 sq ft

819 Madison Ave, Winston Salem, NC 27103

Property at 434 Oak Summit Rd, Winston Salem, NC 27105, 3 beds, 1.5 baths

$235,000

3 beds1.5 baths1,116 sq ft

434 Oak Summit Rd, Winston Salem, NC 27105

Property at 621 Mulberry St SW, Winston Salem, NC 27101, 3 beds, 2 baths

$300,000

3 beds2 baths1,781 sq ft

621 Mulberry St SW, Winston Salem, NC 27101

Property at 2730 Glenn Ave, Winston Salem, NC 27105, 4 beds, 2 baths

$210,000

4 beds2 baths1,790 sq ft

2730 Glenn Ave, Winston Salem, NC 27105

Property at 224 W Banner Ave, Winston Salem, NC 27127, 2 beds, 2 baths

$475,000

2 beds2 baths1,474 sq ft

224 W Banner Ave, Winston Salem, NC 27127

Property at 201 Cecil Dr, Winston Salem, NC 27105, 3 beds, 1.5 baths

$179,000

3 beds1.5 baths1,168 sq ft

201 Cecil Dr, Winston Salem, NC 27105

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 1147 Strathmore Cir, Winston Salem, NC 27104, 4 beds, 4 baths

$595,000

4 beds4 baths4,236 sq ft

1147 Strathmore Cir, Winston Salem, NC 27104

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 2801 Westridge Rd, Winston Salem, NC 27103, 3 beds, 1.5 baths

$289,000

3 beds1.5 baths1,072 sq ft

2801 Westridge Rd, Winston Salem, NC 27103

Property at 1466 Ebert St, Winston Salem, NC 27103, 3 beds, 2 baths

$295,000

3 beds2 baths1,418 sq ft

1466 Ebert St, Winston Salem, NC 27103

Property at 3915 Avera Ave, Winston Salem, NC 27106, 3 beds, 2 baths

$330,000

3 beds2 baths1,913 sq ft

3915 Avera Ave, Winston Salem, NC 27106

Property at 401 E 4th St #302, Winston Salem, NC 27101, 1 bed, 1.5 baths

$444,900

1 bed1.5 baths1,222 sq ft

401 E 4th St #302, Winston Salem, NC 27101

Property at 3606 Country Club Rd, Winston Salem, NC 27104, 3 beds, 1.5 baths

$429,900

3 beds1.5 baths1,643 sq ft

3606 Country Club Rd, Winston Salem, NC 27104

Property at 126 Mayfair Dr, Winston Salem, NC 27105, 3 beds, 1.5 baths

$210,000

3 beds1.5 baths1,714 sq ft

126 Mayfair Dr, Winston Salem, NC 27105

Property at 3868 Grayson Dr, Winston Salem, NC 27107, 2 beds, 1 bath

$179,999

2 beds1 bath1,092 sq ft

3868 Grayson Dr, Winston Salem, NC 27107

Property at 436 E Sprague St, Winston Salem, NC 27127

$275,000

— beds— baths— sq ft

436 E Sprague St, Winston Salem, NC 27127

Property at 755 Faircloth Ave, Winston Salem, NC 27106, 2 beds, 1 bath

$245,000

2 beds1 bath832 sq ft

755 Faircloth Ave, Winston Salem, NC 27106

Property at 530 Barbara Jane Ave, Winston Salem, NC 27101, 3 beds, 1 bath

$130,000

3 beds1 bath1,022 sq ft

530 Barbara Jane Ave, Winston Salem, NC 27101

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

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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 176 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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