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

147 homes

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ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
Beautifully built and rich in character, this updated home offers timeless craftsmanship with modern comfort. Perfect for professionals seeking a distinctive home office or stylish residence, it features high visibility; it’s near to Wake Forest University, hospitals, and major roads. The solid construction and thoughtful updates provide both function and charm—gleaming hardwood floors, elegant moldings, tall ceilings, and inviting natural light throughout. Recent upgrades include wheelchair-accessible ramp, no interior steps, easy upkeep flooring, spacious guest half bath, and a private full bath. The flexible layout allows seamless transition between living and working spaces.

$429,900

3 beds1.5 baths1,643 sq ft

3606 Country Club Rd, Winston Salem, NC 27104

No interior steps • Easy upkeep flooring • Private full bath

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
No HOA! Situated on 0.73 acres, this beautifully remodeled 3-bedroom, 2-bath home has it all! Updates include new drywall, electrical, plumbing, windows, roof, kitchen cabinets, flooring, HVAC, water heater, fresh interior paint, granite countertops, and stainless steel appliances—move-in ready! Enjoy the spacious living room, large bedrooms with plenty of privacy, and a relaxing back porch. The property also features new concrete parking and plenty of outdoor space. Schedule your showing today and experience the peace and privacy this home offers. Bring me an offer!

$274,000

3 beds2 baths1,633 sq ft

4433 Ogburn Ave, Winston Salem, NC 27105

Fresh paint • Stylish fixtures • New flooring

ABOUT THIS HOME
Vintage Home for sale in Winston-Salem, NC:
OPEN HOUSE SUNDAY JANUARY 4, 2026, from 2-4:00. Priced below recent appraisal! Welcome to this charming 2-bedroom, 1-bathroom cottage. This single-level home boasts an array of modern amenities including an eat-in kitchen, updated windows, light fixtures, and kitchen countertops. The enclosed back porch offers a perfect space for relaxation while the detached carport provides additional convenience. The living room and den are designed for comfort and style. The home is conveniently located near major highways, making commuting a breeze. Per seller the roof is approximately 8 years old, and the HVAC system is approximately 7 years old, adding to the home's durability and comfort. The prope

$179,500

2 beds1 bath989 sq ft

125 Brevard St, Winston Salem, NC 27101

Enclosed back porch • Detached carport • Updated windows

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

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

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

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

$209,900

3 beds2 baths1,835 sq ft

1121 Rich Ave, Winston Salem, NC 27101

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 481 David Smith Rd, Winston Salem, NC 27127, 3 beds, 2.5 baths

$329,900

3 beds2.5 baths2,798 sq ft

481 David Smith Rd, Winston Salem, NC 27127

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 137 Vogler Dr, Winston Salem, NC 27107, 3 beds, 1 bath

$185,000

3 beds1 bath1,101 sq ft

137 Vogler Dr, Winston Salem, NC 27107

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

$437,500

5 beds2 baths2,086 sq ft

800 Brent St, Winston Salem, NC 27103

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

$139,900

3 beds1 bath1,330 sq ft

613 N Jackson Ave, Winston Salem, NC 27101

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

$269,900

3 beds2 baths1,425 sq ft

4420 Chebar Dr, Pfafftown, NC 27040

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 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 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 122 Rosedale Cir, Winston Salem, NC 27106, 3 beds, 2 baths

$327,000

3 beds2 baths1,788 sq ft

122 Rosedale Cir, Winston Salem, NC 27106

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

$300,000

3 beds3.5 baths2,229 sq ft

2434 New Walkertown Rd, Winston Salem, NC 27101

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

$239,900

3 beds2 baths1,380 sq ft

445 E Devonshire St, Winston Salem, NC 27127

Property at 1414 Jonestown Rd, Winston Salem, NC 27103, 2 beds, 2 baths

$268,500

2 beds2 baths1,124 sq ft

1414 Jonestown Rd, Winston Salem, NC 27103

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 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 2025 Craig St, Winston Salem, NC 27103, 4 beds, 2 baths

$432,000

4 beds2 baths2,016 sq ft

2025 Craig St, Winston Salem, NC 27103

Property at 927 Apple St, Winston Salem, NC 27101, 5 beds, 4 baths

$320,000

5 beds4 baths2,130 sq ft

927 Apple St, Winston Salem, NC 27101

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 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 700 Magnolia St, Winston Salem, NC 27103, 4 beds, 3 baths

$525,000

4 beds3 baths2,287 sq ft

700 Magnolia St, Winston Salem, NC 27103

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 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 1143 Ebert St, Winston Salem, NC 27103, 3 beds, 2 baths

$332,900

3 beds2 baths1,313 sq ft

1143 Ebert St, Winston Salem, NC 27103

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

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Based on information submitted to the MLS GRID as of Sat Jan 03 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 Winston-Salem

There are currently 147 vintage homes for sale in Winston-Salem at a median listing price of $308K. 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 58 days and receive 5 offers. Popular neighborhoods include St. Ben's, 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, 192 homes have been sold in Winston-Salem. In addition to houses in Winston-Salem, there were also 80 condos, 85 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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