The most expensive neighborhoods in Winston-Salem
The most expensive neighborhoods in Winston-Salem
Homebuyers and sellers are navigating a slow and expensive housing market, with rising prices and stagnant demand keeping many on the sidelines. This comes amid rising economic uncertainty and growing wealth concentration. But luxury homes—multimillion-dollar estates, sleek penthouses, and one-of-a-kind custom builds—are still selling, even as most buyers pull back.
Most people can't afford high-end homes, although they're still fun to dream about. So, to highlight where luxury real estate is commanding the highest prices, Redfin analyzed the most expensive neighborhoods in the Winston-Salem metro area—and showcased a few of the area's standout listings (when possible).
Note: Redfin's analysis focused on metro areas, meaning some neighborhoods fell within smaller nearby cities. Listings and data were gathered on October 15, 2025.
#1. Salem, NC (Winston)
Median sale price: $625,000 | Median days on market: 34 days100 Muirfield Dr, Winston Salem, NC 27104
- List price: $1,299,000
- Beds: 3 | Baths: 3.5 | Square feet: 3,580
- See 100 Muirfield Dr, Winston Salem, NC 27104 on Redfin.com
248 Anita Dr, Winston Salem, NC 27104
- List price: $499,000
- Beds: 3 | Baths: 2 | Square feet: 2,954
- See 248 Anita Dr, Winston Salem, NC 27104 on Redfin.com
3021 Kinnamon Rd, Winston Salem, NC 27104
- List price: $319,900
- Beds: 3 | Baths: 2 | Square feet: 1,142
- See 3021 Kinnamon Rd, Winston Salem, NC 27104 on Redfin.com
3128 Kinnamon Rd, Winston Salem, NC 27104
- List price: $425,000
- Beds: 3 | Baths: 3 | Square feet: 2,704
- See 3128 Kinnamon Rd, Winston Salem, NC 27104 on Redfin.com
#2. Waterford (Clemmons, NC)
Median sale price: $596,500 | Median days on market: 21 days1744 Curraghmore Rd, Clemmons, NC 27012
- List price: $479,900
- Beds: 4 | Baths: 2.5 | Square feet: 2,724
- See 1744 Curraghmore Rd, Clemmons, NC 27012 on Redfin.com
1936 Waterford Village Dr, Clemmons, NC 27012
- List price: $499,900
- Beds: 6 | Baths: 3.5 | Square feet: 3,364
- See 1936 Waterford Village Dr, Clemmons, NC 27012 on Redfin.com
2023 Waterford Village Dr, Clemmons, NC 27012
- List price: $559,000
- Beds: 5 | Baths: 3.5 | Square feet: 3,571
- See 2023 Waterford Village Dr, Clemmons, NC 27012 on Redfin.com
8061 Glengarriff Rd, Clemmons, NC 27012
- List price: $499,900
- Beds: 3 | Baths: 3 | Square feet: 2,984
- See 8061 Glengarriff Rd, Clemmons, NC 27012 on Redfin.com
#3. Salem, NC (Winston)
Median sale price: $578,000 | Median days on market: 34 days1920 Robinhood Rd, Winston Salem, NC 27104
- List price: $649,900
- Beds: 3 | Baths: 4 | Square feet: 2,207
- See 1920 Robinhood Rd, Winston Salem, NC 27104 on Redfin.com
2520 Robinhood Rd, Winston Salem, NC 27106
- List price: $699,000
- Beds: 4 | Baths: 2.5 | Square feet: 2,849
- See 2520 Robinhood Rd, Winston Salem, NC 27106 on Redfin.com
2960 Reynolds Sq, Winston Salem, NC 27106
- List price: $1,375,000
- Beds: 4 | Baths: 4.5 | Square feet: 4,474
- See 2960 Reynolds Sq, Winston Salem, NC 27106 on Redfin.com
465 Sheffield Dr, Winston Salem, NC 27104
- List price: $1,695,000
- Beds: 4 | Baths: 4.5 | Square feet: 5,571
- See 465 Sheffield Dr, Winston Salem, NC 27104 on Redfin.com
#4. Salem, NC (Winston)
Median sale price: $505,000 | Median days on market: 38 days1035 Deepwood Ct, Winston Salem, NC 27104
- List price: $464,900
- Beds: 3 | Baths: 2 | Square feet: 2,157
- See 1035 Deepwood Ct, Winston Salem, NC 27104 on Redfin.com
106 N Hawthorne Rd, Winston Salem, NC 27104
- List price: $359,900
- Beds: 3 | Baths: 2.5 | Square feet: 1,890
- See 106 N Hawthorne Rd, Winston Salem, NC 27104 on Redfin.com
318 Anita Dr, Winston Salem, NC 27104
- List price: $389,900
- Beds: 3 | Baths: 2 | Square feet: 2,133
- See 318 Anita Dr, Winston Salem, NC 27104 on Redfin.com
540 N Stratford Rd, Winston Salem, NC 27104
- List price: $1,890,000
- Beds: 5 | Baths: 4.5 | Square feet: 5,465
- See 540 N Stratford Rd, Winston Salem, NC 27104 on Redfin.com
#5. Salem, NC (Winston)
Median sale price: $450,000 | Median days on market: 35 days1201 Cliffspring Ct, Winston Salem, NC 27104
- List price: $599,900
- Beds: 4 | Baths: 3.5 | Square feet: 3,678
- See 1201 Cliffspring Ct, Winston Salem, NC 27104 on Redfin.com
5005 Marble Arch Rd, Winston Salem, NC 27104
- List price: $1,200,000
- Beds: 4 | Baths: 5 | Square feet: 5,253
- See 5005 Marble Arch Rd, Winston Salem, NC 27104 on Redfin.com
813 Chancy Ln, Winston Salem, NC 27104
- List price: $352,000
- Beds: 3 | Baths: 2.5 | Square feet: 2,358
- See 813 Chancy Ln, Winston Salem, NC 27104 on Redfin.com
900 Brintonial Way, Winston Salem, NC 27104
- List price: $334,900
- Beds: 3 | Baths: 2.5 | Square feet: 2,531
- See 900 Brintonial Way, Winston Salem, NC 27104 on Redfin.com
