Vintage homes for sale & real estate in 27101, NC

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ABOUT THIS HOME
Vintage Home for sale in 27101, NC:
Historic character meets effortless living in the heart of Winston-Salem’s highly coveted West End Historic District. Situated on a rare and generous 0.33-acre lot, this iconic ~1920 home offers over 3,000 square feet of timeless architectural detail and generous living spaces. Step inside to discover classic hardwood flooring, soaring high ceilings, expansive windows filling the home with natural sunlight, and character-rich fireplaces that anchor the main living areas. The flexible 3-bedroom, 2-bathroom layout features spacious bedrooms and versatile bonus areas perfect for a home office, library, or main-level flex space. Outside, enjoy peaceful tree-lined views, an expansive backy

$470,000

3 beds2 baths3,090 sq ft

Hardwood flooring • Expansive windows • Flexible layout

1037 West End Blvd, Winston Salem, NC 27101

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 27101, NC:
2 BRs + separate STUDY; Penthouse-style, 2-story residence in coveted Building 3 in the Mill at Tar Branch! Other penthouse-style residences on this floor have recently sold for well over $700,000 -- this one is priced to allow a new owner to customize to their taste; Well maintained, with recent heat pump (2019); Impressive double-height great room with massive windows providing tons of natural light; Granite kitchen counters and Bosch dishwasher; Half-bath and laundry area on main level; Main-level primary suite with dual closets and large bath with tile shower/separate tub; Upstairs is a cozy loft/study with built-ins along with a second BR and a full bath; Originally a textile mill, con

$587,000

2 beds2.5 baths1,879 sq ft

Bosch dishwasher • Massive windows • Separate study

327 Indera Mills Ct, Winston Salem, NC 27101

ABOUT THIS HOME
Vintage Home for sale in 27101, NC:
Welcome to this immaculately updated three-bedroom, two-bathroom home, thoughtfully renovated with modern style & comfort! This property features numerous upgrades, including a new HVAC system, roof, water heater, energy-efficient windows & durable luxury vinyl plank flooring throughout. The kitchen has been refreshed with granite countertops & new cabinetry. Both bathrooms have new vanities & stylish tiled shower surrounds. Contemporary lighting fixtures update the home's lighting. Outside offers a charming front porch & newly refreshed landscaping with attractive greenery, plantings & professionally finished exterior details. A covered carport in the ba

$225,900

3 beds2 baths1,560 sq ft

New water heater • Granite countertops • New roof

614 N Cameron Ave, Winston Salem, NC 27101

ABOUT THIS HOME
Vintage Home for sale in 27101, NC:
Cute 3 bed 1 bath home with some recent updates. Convenient location close to downtown Winston Salem, Winston Salem State University, Interstate 40 and hwy 52.

$145,000

3 beds1 bath880 sq ft

0.3 acre lot • Garage • Built 1955

2138 Gerald St, Winston Salem, NC 27101

ABOUT THIS HOME
Vintage Home for sale in 27101, NC:
Discover the classic character and potential of this 1922 conventional-style home, situated on a spacious lot in Winston-Salem. The exterior welcomes you with a classic layout featuring an enclosed front sunroom porch providing a versatile entry space. Inside find rich, original-style hardwood floors stretching through a bright formal living room including a fireplace mantel. The formal dining room flows seamlessly into a kitchen loaded with personality, highlighting a vibrant red brick accent wall, natural wood cabinetry, and stainless steel appliances. For extra space, the separate den offers a cozy retreat lined with warm wood paneling and soft carpeting. Convenience is built-in with a d

$150,000

3 beds2 baths1,946 sq ft

Separate den • 0.61 acre lot • Garage

305 Walkertown Guthrie Rd, Winston Salem, NC 27101

Property at 702 Granville Dr SW, Winston Salem, NC 27101, 3 beds, 3 baths

$335,000

3 beds3 baths2,744 sq ft

702 Granville Dr SW, Winston Salem, NC 27101

Property at 1259 W 4th St, Winston Salem, NC 27101

$450,000

— beds— baths1,176 sq ft

1259 W 4th St, Winston Salem, NC 27101

Property at 933 West St, Winston Salem, NC 27101, 3 beds, 1.5 baths

$385,000

3 beds1.5 baths1,625 sq ft

933 West St, Winston Salem, NC 27101

Property at 509 W 1st St, Winston Salem, NC 27101, 6 beds, 2 baths

$275,000

6 beds2 baths744 sq ft

509 W 1st St, Winston Salem, NC 27101

Property at 1025 West End Blvd, Winston Salem, NC 27101

$795,000

— beds— baths— sq ft

1025 West End Blvd, Winston Salem, NC 27101

Property at 1022 Franklin St, Winston Salem, NC 27101, 4 beds, 2 baths

$154,995

4 beds2 baths1,458 sq ft

1022 Franklin St, Winston Salem, NC 27101

Property at 836 Oak St #306, Winston Salem, NC 27101, 1 bed, 1 bath

$234,900

1 bed1 bath712 sq ft

836 Oak St #306, Winston Salem, NC 27101

Property at 2163 Gerald St, Winston Salem, NC 27101, 3 beds, 1 bath

$169,900

3 beds1 bath876 sq ft

2163 Gerald St, Winston Salem, NC 27101

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

$235,000

3 beds2 baths1,429 sq ft

621 Mulberry St, Winston Salem, NC 27101

Property at 523 W First St, Winston Salem, NC 27101, 3 beds, 3 baths

$409,900

3 beds3 baths2,215 sq ft

523 W First St, Winston Salem, NC 27101

Property at 721 Mulberry St, Winston Salem, NC 27101, 2 beds, 1 bath

$229,900

2 beds1 bath1,062 sq ft

721 Mulberry St, Winston Salem, NC 27101

Property at 415 S Poplar St, Winston Salem, NC 27101, 3 beds, 4 baths

$300,000

3 beds4 baths1,752 sq ft

415 S Poplar St, Winston Salem, NC 27101

Property at 1 W 5th St #207, Winston Salem, NC 27101, 2 beds, 2 baths

$399,900

2 beds2 baths1,362 sq ft

1 W 5th St #207, Winston Salem, NC 27101

Property at 1420 W 4th St, Winston Salem, NC 27101, 5 beds, 3 baths

$175,000

5 beds3 baths2,767 sq ft

1420 W 4th St, Winston Salem, NC 27101

Property at 1 W 5th St #204, Winston Salem, NC 27101, 2 beds, 1 bath

$369,900

2 beds1 bath1,224 sq ft

1 W 5th St #204, Winston Salem, NC 27101

Property at 1024 Franklin St, Winston Salem, NC 27101, 4 beds, 2 baths

$395,000

4 beds2 baths1,978 sq ft

1024 Franklin St, Winston Salem, NC 27101

Property at 155 Tar Branch Ct, Winston-salem, NC 27101, 1 bed, 2 baths

$549,000

1 bed2 baths1,788 sq ft

155 Tar Branch Ct, Winston-salem, NC 27101

Property at 509 Washington Ave, Winston Salem, NC 27101, 2 beds, 1 bath

$259,900

2 beds1 bath1,110 sq ft

509 Washington Ave, Winston Salem, NC 27101

Property at 949 Hutton St, Winston Salem, NC 27101, 3 beds, 1 bath

$299,000

3 beds1 bath1,503 sq ft

949 Hutton St, Winston Salem, NC 27101

Property at 428 S Main St, Winston Salem, NC 27101, 5 beds, 5.5 baths

$2,395,000

5 beds5.5 baths7,113 sq ft

428 S Main St, Winston Salem, NC 27101

Property at 1 W 5th St #302, Winston Salem, NC 27101, 1 bed, 1 bath

$299,900

1 bed1 bath790 sq ft

1 W 5th St #302, Winston Salem, NC 27101

Property at 828 Ferrell Ave, Winston Salem, NC 27101, 2 beds, 1 bath

$149,900

2 beds1 bath838 sq ft

828 Ferrell Ave, Winston Salem, NC 27101

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

$200,000

1 bed1.5 baths942 sq ft

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

Property at 800 W Academy St, Winston Salem, NC 27101, 2 beds, 1 bath

$249,500

2 beds1 bath828 sq ft

800 W Academy St, Winston Salem, NC 27101

Property at 1448 W 4th St, Winston Salem, NC 27101, 4 beds, 2 baths

$149,950

4 beds2 baths902 sq ft

1448 W 4th St, Winston Salem, NC 27101

Property at 1919 Maryland Ave, Winston Salem, NC 27101, 3 beds, 2 baths

$205,000

3 beds2 baths1,140 sq ft

1919 Maryland Ave, Winston Salem, NC 27101

Property at 1224 W 1st St, Winston Salem, NC 27101, 4 beds, 2 baths

$405,000

4 beds2 baths1,896 sq ft

1224 W 1st St, Winston Salem, NC 27101

Property at 619 Laurel St, Winston Salem, NC 27101, 2 beds, 1 bath

$241,900

2 beds1 bath847 sq ft

619 Laurel St, Winston Salem, NC 27101

Property at 309 Beaumont St, Winston Salem, NC 27101, 3 beds, 1 bath

$222,000

3 beds1 bath1,258 sq ft

309 Beaumont St, Winston Salem, NC 27101

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

$380,000

5 beds3 baths2,254 sq ft

1444 W 4th St, Winston Salem, NC 27101

Property at 1 W 5th St #102, Winston Salem, NC 27101, 2 beds, 2 baths

$449,900

2 beds2 baths2,101 sq ft

1 W 5th St #102, Winston Salem, NC 27101

Property at 605 N Dunleith Ave, Winston Salem, NC 27101

$170,000

— beds— baths— sq ft

605 N Dunleith Ave, Winston Salem, NC 27101

Property at 613 N Dunleith Ave, Winston Salem, NC 27101

$290,000

— beds— baths— sq ft

613 N Dunleith Ave, Winston Salem, NC 27101

Property at 315 Spruce St N #301, Winston Salem, NC 27101, 1 bed, 1.5 baths

$214,900

1 bed1.5 baths818 sq ft

315 Spruce St N #301, Winston Salem, NC 27101

Property at 823 W 7th St, Winston Salem, NC 27101, 2 beds, 1 bath

$244,900

2 beds1 bath943 sq ft

823 W 7th St, Winston Salem, NC 27101

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

$168,600

3 beds1 bath960 sq ft

3334 Old Greensboro Rd, Winston Salem, NC 27101

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Based on information submitted to the MLS GRID as of Thu Aug 20 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 27101

There are currently 42 vintage homes for sale in 27101 at a median listing price of $275K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 27101 stay on the market for 64 days and receive 1 offers. This map is refreshed with the newest listings in 27101 every 15 minutes.

In the past month, 19 homes have been sold in 27101. In addition to houses in 27101, there were also 24 condos, 2 townhouses, and 3 multi-family units for sale in 27101 last month. Find your dream home in 27101 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 27101 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 27101. If you're looking to sell your home in the 27101 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 27101 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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