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

176 homes

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ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
* * Open House Sunday, 11/30/25. * * Walkable Ardmore 4BR near Miller Park & the medical corridor—1,761 sf, classic 1947 charm meets updates--granite + stainless kitchen, fenced yard, and a screened patio for indoor-outdoor living. Flexible layout (work from home or guest). Prime in-town location near hospitals, WFU, and downtown corridors. Seller may contribute to buyer allowable closing costs or a temporary rate buydown with acceptable offer. Floor plan + walkability info available. Come see why Ardmore is one of Winston-Salem’s favorite neighborhoods

$389,900

4 beds2 baths1,761 sq ft

909 Knollwood St, Winston Salem, NC 27103

New vanity • New water heater • Granite countertops

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Come see this wonderful cottage, nestled front and back by flower gardens. The living room has hardwood floors & a wood burning fireplace. The light-filled office/sunroom, is ready for work or crafts. Beautifully remodeled Kitchen w/ walk-in pantry, butcher block tops, farm sink and tile floors. A spacious greenhouse window at sink is the perfect place to grow fresh herbs. The dining room has hardwood floors & an closet. Great trex-style deck perfect for grilling. 2 vintage tile baths are a real treat in a home of this era. Ask your contractor if a simple door addition could make one of them an ensuite for the primary bedroom. The primary boasts 2 closets, the 2nd contains built

$390,000

3 beds2 baths1,488 sq ft

1034 Vernon Ave, Winston Salem, NC 27106

0.26 acre lot • Garage • Built 1948

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Welcome to this charming Ardmore home that lives larger than its square footage! Featuring 4 spacious bedrooms and 2 full baths, this property offers the perfect blend of comfort and character. Step inside to a bright living room beaming with beautiful natural light from oversized windows, flowing seamlessly into the dining area and kitchen. Main level includes two generous bedrooms and a full bath, ideal for guests, a home office, or flex space. Upstairs, you’ll find another bedroom plus a spacious primary suite complete with a walk-in closet and a beautifully updated ensuite bath. Outside, enjoy the fenced yard, fire pit, and close proximity to the hospital, coffee shops, and all th

$432,000

4 beds2 baths2,016 sq ft

2025 Craig St, Winston Salem, NC 27103

Fenced yard • Walk-in closet • Fire pit

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Welcome to this charming brick ranch in the heart of Sherwood Forest! On the market for the first time in years, this family home has been lovingly maintained. With 4 bedrooms and 4 full baths, it offers comfort and flexibility for a variety of living arrangements. Updated systems, a Generac generator, and a newer roof provide peace of mind. The main-level two-car garage connects to a spacious laundry/mudroom, making daily routines and rainy-day unloading a breeze. A detached garage (not accessible by car) in the back offers excellent space for storage, a workshop, or hobby area. The finished basement, a Sherwood classic, features a full kitchen, bedroom, and bath — perfect for an in-

$595,000

4 beds4 baths4,236 sq ft

1147 Strathmore Cir, Winston Salem, NC 27104

Generac generator • Full kitchen • Newer roof

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Beautifully restored in 2025…this 1927 home is located in downtown Historic West End. This lovely 4 square is filled with light due to its large original windows and interior french doors. Fully restored while retaining the 20’s character, the custom wood trimwork, custom cabinetry in kitchen and primary bath, and freshly refinished floors are stunning. Looking thru the wavy glass windows feels magical. Excellent outdoor spaces as well with large front porch, covered porch on the back deck overlooking the trees and strawberry patch in backyard. Off street parking as well. Easy walking distance to restaurants, theaters and breweries. 2025 updates include: Kitchen, all three bath

$639,000

3 beds2.5 baths2,229 sq ft

157 West End Blvd, Winston Salem, NC 27101

Restored in 2025 • Custom wood trimwork • 0.28 acre lot

Property at 190/200 Stanleyville Manor Ave Unit 1-7, Rural Hall, NC 27045, 2 beds, 1 bath

$295,000

2 beds1 bath728 sq ft

190/200 Stanleyville Manor Ave Unit 1-7, Rural Hall, NC 27045

Property at 4761 Ader Dr, Winston Salem, NC 27105, 3 beds, 1 bath

$229,900

3 beds1 bath1,239 sq ft

4761 Ader Dr, Winston Salem, NC 27105

Property at 5008 Old Rural Hall Rd, Winston Salem, NC 27105, 4 beds, 3 baths

$350,000

4 beds3 baths2,889 sq ft

5008 Old Rural Hall Rd, Winston Salem, NC 27105

Property at 2520 Robinhood Rd, Winston Salem, NC 27106, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths2,849 sq ft

2520 Robinhood Rd, Winston Salem, NC 27106

Property at 3334 Old Greensboro Rd, Winston Salem, NC 27101, 3 beds, 1 bath

$169,000

3 beds1 bath960 sq ft

3334 Old Greensboro Rd, Winston Salem, NC 27101

Property at 1008 E Brookline St, Winston Salem, NC 27107, 3 beds, 1 bath

$199,999

3 beds1 bath912 sq ft

1008 E Brookline St, Winston Salem, NC 27107

Property at 3780 Sandalwood Ln, Winston Salem, NC 27106, 3 beds, 2 baths

$263,500

3 beds2 baths1,275 sq ft

3780 Sandalwood Ln, Winston Salem, NC 27106

Property at 425 E Sprague St, Winston Salem, NC 27127, 3 beds, 1 bath

$165,000

3 beds1 bath1 sq ft

425 E Sprague St, Winston Salem, NC 27127

Property at 4009 Fargo Dr, Winston Salem, NC 27106, 3 beds, 1.5 baths

$219,900

3 beds1.5 baths1,401 sq ft

4009 Fargo Dr, Winston Salem, NC 27106

Property at 445 E Devonshire St, Winston Salem, NC 27127, 3 beds, 2 baths

$245,000

3 beds2 baths1,380 sq ft

445 E Devonshire St, Winston Salem, NC 27127

Property at 106 N Hawthorne Rd, Winston Salem, NC 27104, 3 beds, 2.5 baths

$329,900

3 beds2.5 baths1,890 sq ft

106 N Hawthorne Rd, Winston Salem, NC 27104

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

$410,000

3 beds2 baths1,503 sq ft

520 Gales Ave, Winston Salem, NC 27103

Property at 1444 W 4th St, Winston Salem, NC 27101, 5 beds, 3 baths

$415,000

5 beds3 baths2,254 sq ft

1444 W 4th St, Winston Salem, NC 27101

Property at 335 Fairfax Dr, Winston Salem, NC 27104, 5 beds, 3.5 baths

$1,150,000

5 beds3.5 baths3,400 sq ft

335 Fairfax Dr, Winston Salem, NC 27104

Property at 1424 Belleauwood St, Winston Salem, NC 27107, 3 beds, 1 bath

$144,999

3 beds1 bath1,003 sq ft

1424 Belleauwood St, Winston Salem, NC 27107

Property at 1920 Maryland Ave, Winston Salem, NC 27101, 2 beds, 1 bath

$99,900

2 beds1 bath750 sq ft

1920 Maryland Ave, Winston Salem, NC 27101

Property at 2434 New Walkertown Rd, Winston Salem, NC 27101, 3 beds, 3.5 baths

$310,000

3 beds3.5 baths2,229 sq ft

2434 New Walkertown Rd, Winston Salem, NC 27101

Property at 5230 S Main St, Winston Salem, NC 27107, 3 beds, 2 baths

$285,000

3 beds2 baths1,638 sq ft

5230 S Main St, Winston Salem, NC 27107

Property at 2557 Alderney Ln, Winston Salem, NC 27103, 3 beds, 1.5 baths

$255,000

3 beds1.5 baths1,425 sq ft

2557 Alderney Ln, Winston Salem, NC 27103

Property at 3614 Broadsword Rd, Winston Salem, NC 27104, 4 beds, 3 baths

$520,000

4 beds3 baths2,780 sq ft

3614 Broadsword Rd, Winston Salem, NC 27104

Property at 1325 Gholson Ave, Winston Salem, NC 27107, 2 beds, 1 bath

$88,500

2 beds1 bath570 sq ft

1325 Gholson Ave, Winston Salem, NC 27107

Property at 1366 Pinebluff Rd, Winston Salem, NC 27103, 3 beds, 2.5 baths

$415,000

3 beds2.5 baths1,938 sq ft

1366 Pinebluff Rd, Winston Salem, NC 27103

Property at 700 Ontario St, Winston Salem, NC 27105, 3 beds, 1 bath

$198,999

3 beds1 bath1,333 sq ft

700 Ontario St, Winston Salem, NC 27105

Property at 311 Forest Hill Ave, Winston Salem, NC 27105, 2 beds, 2 baths

$160,000

2 beds2 baths1,382 sq ft

311 Forest Hill Ave, Winston Salem, NC 27105

Property at 2041 Bloomfield Dr, Winston Salem, NC 27107, 2 beds, 1 bath

$165,000

2 beds1 bath681 sq ft

2041 Bloomfield Dr, Winston Salem, NC 27107

Property at 4966 Red Pine Ln, Pfafftown, NC 27040, 2 beds, 1 bath

$189,000

2 beds1 bath1,042 sq ft

4966 Red Pine Ln, Pfafftown, NC 27040

Property at 4966 Yadkinville Rd, Pfafftown, NC 27040, 2 beds, 1 bath

$369,900

2 beds1 bath1,042 sq ft

4966 Yadkinville Rd, Pfafftown, NC 27040

Property at 418 W Acadia Ave, Winston Salem, NC 27127, 3 beds, 2 baths

$495,000

3 beds2 baths3,060 sq ft

418 W Acadia Ave, Winston Salem, NC 27127

Property at 2800 Lomond St, Winston Salem, NC 27127, 3 beds, 1 bath

$199,900

3 beds1 bath1,008 sq ft

2800 Lomond St, Winston Salem, NC 27127

Property at 5615 Plantation Dr, Winston Salem, NC 27105, 3 beds, 1 bath

$235,000

3 beds1 bath1,162 sq ft

5615 Plantation Dr, Winston Salem, NC 27105

Property at 2919 Susan Ln, Winston Salem, NC 27107, 3 beds, 2 baths

$194,900

3 beds2 baths1,352 sq ft

2919 Susan Ln, Winston Salem, NC 27107

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

$399,900

3 beds2 baths1,506 sq ft

1720 Elizabeth Ave, Winston Salem, NC 27103

Property at 2101 E 25th St, Winston Salem, NC 27015, 2 beds, 1 bath

$110,000

2 beds1 bath785 sq ft

2101 E 25th St, Winston Salem, NC 27015

Property at 128 Fishel Rd, Winston Salem, NC 27107, 2 beds, 2 baths

$269,000

2 beds2 baths1,472 sq ft

128 Fishel Rd, Winston Salem, NC 27107

Property at 1616 Queen St, Winston Salem, NC 27103, 2 beds, 1 bath

$219,500

2 beds1 bath1,050 sq ft

1616 Queen St, Winston Salem, NC 27103

Property at 5755 Reynolda Rd, Winston-salem, NC 27106, 4 beds, 2 baths

$550,000

4 beds2 baths2,631 sq ft

5755 Reynolda Rd, Winston-salem, NC 27106

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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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