Vintage homes for sale & real estate in 27111, NC

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NEW 23 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 27111, NC:
Charming. Quaint. Buena Vista! Special, updated, 4-bedroom home located just steps from the bustling and growing BV/ Reynolda Rd. dining and shopping area; as well as the Stuart & Emma Thomas Memorial Trail. Main level lives large, with 2 main level bedrooms plus an office. Inviting great room with masonry fireplace, updated kitchen with quartz ctops and gas range. 2nd floor primary suite/loft with full bath and walk-in closet, also offers another bedroom/nursery/office. Excellent storage in the basement! New deck, recent paint and carpet. Possession available immediately.

$625,000

4 beds2 baths2,081 sq ft

1711 Meadowbrook Dr, Winston Salem, NC 27104

Masonry fireplace • Updated kitchen • New deck

OPEN SUN, 2PM TO 4PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 27111, 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.

$469,000

4 beds2 baths2,323 sq ft

1225 W 4th St, Winston Salem, NC 27101

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

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 27111, NC:
Explore the possibilities with this 2-bedroom, 1-bath home offering approximately 816 square feet of living space. Built in 1930, this property features a covered front porch, an unfinished basement, and a 0.13-acre lot. Conveniently located near downtown Winston-Salem with easy access to shopping, dining, and major highways. With room for improvements and added value, this property is an opportunity for investors or buyers ready to bring their vision to life. Schedule your showing today!

$114,900

2 beds1 bath816 sq ft

1404 Gholson Ave, Winston Salem, NC 27107

Covered front porch • Unfinished basement • 0.13-acre lot

ABOUT THIS HOME
Vintage Home for sale in 27111, NC:
This classic 1920s home stands tall in the BV-West Highlands neighborhood, exuding historic charm & comfort inside & out! All the details have been well-preserved along w/ the classic features-tall ceilings, warm wood floors, picture moulding & more. The main level boasts a large living room w/ decorative FP, separate dining room w/ large windows & the cutest eat-in kitchen giving English cottage vibes. The covered porch beckons w/ its gorgeous slate tile floor & beadboard finishes-enjoy all the seasons here! A wonderful layout awaits upstairs w/ a spacious primary bedroom & private ensuite bath w/ a gorgeous basketweave tile floor & pink tile accen

$410,000

3 beds2.5 baths2,172 sq ft

1525 Cloverdale Ave, Winston Salem, NC 27104

Covered porch • Separate dining room • Paved driveway

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 27111, NC:
Don’t miss this rare opportunity to own a beautiful 2-bedroom, 2-bathroom condo in the heart of historic West End! Enjoy the best of both worlds with easy access to all the excitement of downtown Winston-Salem while still enjoying the peace and privacy of this tucked-away West End location. Inside, you’ll find soaring ceilings, bedrooms filled with natural light and handsome hardwood floors. Stylish kitchen with ample cabinets and stainless appliances. The cozy screened-in porch perfect for relaxing. Assigned off-street parking adds even more convenience. This charming condo is a must-see!

$259,900

2 beds2 baths936 sq ft

72 West End Blvd #5, Winston Salem, NC 27101

Historic west end • Soaring ceilings • Natural light

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

$375,000

3 beds2 baths1,513 sq ft

1720 Elizabeth Ave, Winston Salem, NC 27103

Property at 1224 Glade St, Winston Salem, NC 27101, 3 beds, 2.5 baths

$785,000

3 beds2.5 baths2,858 sq ft

1224 Glade St, Winston Salem, NC 27101

Property at 1314 First St E, Winston Salem, NC 27101, 3 beds, 1 bath

$184,900

3 beds1 bath1,120 sq ft

1314 First St E, Winston Salem, NC 27101

Property at 730 Alexander St, Winston Salem, NC 27127, 2 beds, 1 bath

$79,900

2 beds1 bath700 sq ft

730 Alexander St, Winston Salem, NC 27127

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 419 S Sunset Dr, Winston Salem, NC 27103, 3 beds, 1 bath

$290,000

3 beds1 bath1,431 sq ft

419 S Sunset Dr, Winston Salem, NC 27103

Property at 812 Holland St, Winston Salem, NC 27101, 3 beds, 1 bath

$325,000

3 beds1 bath1,358 sq ft

812 Holland St, Winston Salem, NC 27101

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 1011 Manly St, Winston Salem, NC 27105, 2 beds, 1 bath

$129,900

2 beds1 bath680 sq ft

1011 Manly St, Winston Salem, NC 27105

Property at 1523 W First St, Winston Salem, NC 27104, 4 beds, 3.5 baths

$490,000

4 beds3.5 baths3,068 sq ft

1523 W First St, Winston Salem, NC 27104

Property at 1708 Grace St, Winston Salem, NC 27103, 2 beds, 1.5 baths

$319,000

2 beds1.5 baths1,232 sq ft

1708 Grace St, Winston Salem, NC 27103

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 401 S Sunset Dr, Winston Salem, NC 27103, 4 beds, 3 baths

$379,000

4 beds3 baths1,972 sq ft

401 S Sunset Dr, Winston Salem, NC 27103

Property at 1445 Underwood Ave, Winston Salem, NC 27105, 2 beds, 1 bath

$189,900

2 beds1 bath860 sq ft

1445 Underwood Ave, Winston Salem, NC 27105

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

$315,000

3 beds2 baths1,520 sq ft

520 Gales Ave, Winston Salem, NC 27103

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 847 Lockland Ave, Winston Salem, NC 27103, 4 beds, 2 baths

$399,900

4 beds2 baths1,682 sq ft

847 Lockland Ave, Winston Salem, NC 27103

Property at 800 S Sunset Dr, Winston Salem, NC 27103, 3 beds, 2 baths

$339,000

3 beds2 baths1,224 sq ft

800 S Sunset Dr, Winston Salem, NC 27103

Property at 907 Roosevelt St, Winston Salem, NC 27105, 2 beds, 1 bath

$128,000

2 beds1 bath832 sq ft

907 Roosevelt St, Winston Salem, NC 27105

Property at 319 Lockland Ave, Winston Salem, NC 27103, 3 beds, 2 baths

$399,900

3 beds2 baths1,539 sq ft

319 Lockland Ave, Winston Salem, NC 27103

Property at 1529 Fitch St, Winston Salem, NC 27107, 2 beds, 1 bath

$169,900

2 beds1 bath856 sq ft

1529 Fitch St, Winston Salem, NC 27107

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 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 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

$299,900

1 bed1 bath967 sq ft

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

Property at 1504 Gholson Ave, Winston Salem, NC 27107, 2 beds, 1 bath

$110,000

2 beds1 bath816 sq ft

1504 Gholson Ave, Winston Salem, NC 27107

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 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 641 S Hawthorne Rd, Winston Salem, NC 27103, 2 beds, 1 bath

$320,000

2 beds1 bath1,327 sq ft

641 S Hawthorne Rd, Winston Salem, NC 27103

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

$234,900

2 beds1 bath1,030 sq ft

725 S Green St, Winston Salem, NC 27101

Property at 922 Taft St, Winston Salem, NC 27105, 2 beds, 1 bath

$109,900

2 beds1 bath639 sq ft

922 Taft St, Winston Salem, NC 27105

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 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 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 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

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Based on information submitted to the MLS GRID as of Sat Oct 10 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 27111

There are currently 60 vintage homes for sale in 27111. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. This map is refreshed with the newest listings in 27111 every 15 minutes.

Find your dream home in 27111 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 27111 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 27111. If you're looking to sell your home in the 27111 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 27111 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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