Vintage homes for sale & real estate in 27101, NC

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COMING SOONFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 27101, NC:
Gracious craftsman bungalow in the Historic West End with high ceilings, handsome moldings, and built-ins throughout. An eat-in kitchen overlooks the backyard and generous rear deck, while a porch swing awaits on the front porch. The flexible floor plan offers a potential main-level primary suite and main-level laundry, with surprising storage upstairs. A rare find for the neighborhood: a fully functioning garage. Steps from Burke Street, close to downtown and Atrium Health Wake Forest Baptist. Showings begin Thursday, October 8.

$469,000

4 beds2 baths2,323 sq ft

1225 W 4th St, Winston Salem, NC 27101

Craftsman bungalow • Eat-in kitchen • Main-level laundry

ABOUT THIS HOME
Vintage Home for sale in 27101, NC:
Convenient Location Salem Parkway, and US 52. Walking distance to WSSU and bus line, just minutes from downtown Winston Salem. Property Redone Appx 6 years ago. Property shows like new. Beautiful kitchen with granite countertops. Nice laminated flooring throughout. Large sit in shower, Spacious laundry room area great for extra storage. Matching smooth top range and refrigerator to remain. Nice covered front porch. All located on nice level back lot with lots of shades trees that is great for entertainment, cookout etc. and garden area.

$184,900

3 beds1 bath1,120 sq ft

1314 First St E, Winston Salem, NC 27101

Large sit in shower • Level back lot • 4,791 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in 27101, NC:
Spacious, turn-of-the-century, converted to quadraplex in 1980s. Priced UNDER appraised value. Three 1-bedroom units and one 2-bedroom unit. Hardwood floors throughout; period tiled fireplaces; high ceilings; common laundry in unfinished basement. Convenient location, LARGE lot connecting to Peters Creek Pkwy. Proximity to Truist Stadium. Being sold as-is. There is an adjacent vacant lot (1280 Apple Street, MLS #1236951); Sellers prefer to sell both properties together. Separate electrical meters for each unit; renters’ gas and water can be divided based on square ft. Utilities are in the process of being tuned on. Boiler heating system has not been used for some tim

$205,000

5 beds4 baths3,652 sq ft

1409 W 4th St, Winston Salem, NC 27101

Large lot • Hardwood floors • 0.33 acre lot

ABOUT THIS HOME
Vintage Home for sale in 27101, NC:
1224 Glade Street (The Carroll-Trivette House 1910) located in the West End Historic District. Close to all of your favorites . .. .. Hanes Park, Central Y, Grace Court, restaurants and shopping. Take in the view from a gorgeous wraparound front porch. High ceilings, generous room sizes, handsome dining room, living room and updated large cook's kitchen. Primary bedroom suite has tiled steam shower, heated tile floor with spacious walk in closet and permanent stairs leading to floored attic. Easy access to rear alley, 2 car detached garage and additional parking spaces.

$785,000

3 beds2.5 baths2,858 sq ft

1224 Glade St, Winston Salem, NC 27101

Heated tile floor • Tiled steam shower • Detached garage

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 27101, NC:
Welcome to 812 Holland Street, a beautifully restored 1930’s home nestled in the historic West End within walking distance to Granville Park and just minutes from downtown Winston-Salem, Old Salem, shopping, dining and hospitals. This home has a brand new air conditioning system, all new windows, new bathroom tile, refinished hardwood floors and a fresh coat of paint that brightens every room. Upstairs there is a spacious bedroom and loft space adorned in knotty pine. Outside enjoy the covered front porch or the shady back yard that includes a convenient storage shed. All move-in ready. Schedule your showing today!

$325,000

3 beds1 bath1,358 sq ft

812 Holland St, Winston Salem, NC 27101

Fresh coat of paint • Historic west end • Spacious bedroom

Property at 803 S Main St, Winston Salem, NC 27101, 14 beds, 14.5 baths

$1,295,000

14 beds14.5 baths6,027 sq ft

803 S Main St, Winston Salem, NC 27101

Property at 440 Granville Dr SW, Winston Salem, NC 27101, 3 beds, 1 bath

$315,000

3 beds1 bath1,261 sq ft

440 Granville Dr SW, Winston Salem, NC 27101

Property at 4326 Stokesdale Ave, Winston Salem, NC 27101, 3 beds, 1.5 baths

$199,900

3 beds1.5 baths1,035 sq ft

4326 Stokesdale Ave, Winston Salem, NC 27101

Property at 123 S Sunset Dr, Winston Salem, NC 27101, 3 beds, 2 baths

$434,900

3 beds2 baths2,049 sq ft

123 S Sunset Dr, Winston Salem, NC 27101

Property at 118 & 120 S Poplar St, Winston Salem, NC 27101, 2 beds, 2 baths

$225,000

2 beds2 baths— sq ft

118 & 120 S Poplar St, Winston Salem, NC 27101

Property at 4412 Reidsville Rd, Winston Salem, NC 27101, 2 beds, 1 bath

$185,000

2 beds1 bath1,038 sq ft

4412 Reidsville Rd, Winston Salem, NC 27101

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

$144,900

2 beds1 bath838 sq ft

828 Ferrell Ave, Winston Salem, NC 27101

Property at 632 S Green St, Winston Salem, NC 27101, 3 beds, 2 baths

$375,000

3 beds2 baths1,748 sq ft

632 S Green St, Winston Salem, NC 27101

Property at 719 S Green St, Winston Salem, NC 27101, 2 beds, 1 bath

$219,000

2 beds1 bath1,239 sq ft

719 S Green St, Winston Salem, NC 27101

Property at 101 N Chestnut St #4, Winston Salem, NC 27127, 1 bed, 1 bath

$319,000

1 bed1 bath967 sq ft

101 N Chestnut St #4, Winston Salem, NC 27127

Property at 327 Indera Mills Ct, Winston Salem, NC 27101, 2 beds, 2.5 baths

$587,000

2 beds2.5 baths1,879 sq ft

327 Indera Mills Ct, Winston Salem, NC 27101

Property at 220 Tar Branch Ct, Winston Salem, NC 27101, 2 beds, 2 baths

$400,000

2 beds2 baths1,498 sq ft

220 Tar Branch Ct, 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 621 Mulberry St, Winston Salem, NC 27101, 3 beds, 2 baths

$229,000

3 beds2 baths1,429 sq ft

621 Mulberry St, Winston Salem, NC 27101

Property at 725 S Green St, Winston Salem, NC 27101, 2 beds, 1 bath

$239,900

2 beds1 bath1,030 sq ft

725 S Green St, Winston Salem, NC 27101

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

$297,500

3 beds1 bath1,503 sq ft

949 Hutton St, Winston Salem, NC 27101

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

$390,000

4 beds2 baths1,978 sq ft

1024 Franklin St, Winston Salem, NC 27101

Property at 1025 West End Blvd, Winston Salem, NC 27101, 5 beds, 5 baths

$795,000

5 beds5 baths— sq ft

1025 West End Blvd, Winston Salem, NC 27101

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

$365,000

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 558 Kinard Dr, Winston Salem, NC 27101, 3 beds, 1 bath

$175,000

3 beds1 bath1,008 sq ft

558 Kinard Dr, 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 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 1259 W 4th St, Winston Salem, NC 27101, 3 beds, 2 baths

$450,000

3 beds2 baths1,176 sq ft

1259 W 4th 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 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 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 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 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 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 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 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 315 Spruce St N #301, Winston Salem, NC 27101, 1 bed, 1.5 baths

$205,500

1 bed1.5 baths818 sq ft

315 Spruce St N #301, 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 309 Beaumont St, Winston Salem, NC 27101, 3 beds, 1 bath

$219,000

3 beds1 bath1,258 sq ft

309 Beaumont St, Winston Salem, NC 27101

Property at 605 N Dunleith Ave, Winston Salem, NC 27101, 2 beds, 2 baths

$165,500

2 beds2 baths— sq ft

605 N Dunleith Ave, Winston Salem, NC 27101

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Based on information submitted to the MLS GRID as of Mon Oct 05 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 44 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 79 days and receive 1 offers. This map is refreshed with the newest listings in 27101 every 15 minutes.

In the past month, 17 homes have been sold in 27101. In addition to houses in 27101, there were also 21 condos, 3 townhouses, and 6 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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