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.
Median sale price: $625,000 | Median days on market: 34 days
- Beds: 3 | Baths: 3.5 | Square feet: 3,580
- Beds: 3 | Baths: 3 | Square feet: 2,704
Median sale price: $596,500 | Median days on market: 21 days
- Beds: 4 | Baths: 2.5 | Square feet: 2,724
- Beds: 6 | Baths: 3.5 | Square feet: 3,364
- Beds: 5 | Baths: 3.5 | Square feet: 3,571
- Beds: 3 | Baths: 3 | Square feet: 2,984
Median sale price: $578,000 | Median days on market: 34 days
- Beds: 3 | Baths: 4 | Square feet: 2,207
- Beds: 4 | Baths: 2.5 | Square feet: 2,849
- Beds: 4 | Baths: 4.5 | Square feet: 4,474
- Beds: 4 | Baths: 4.5 | Square feet: 5,571
Median sale price: $505,000 | Median days on market: 38 days
- Beds: 3 | Baths: 2 | Square feet: 2,157
106 N Hawthorne Rd, Winston Salem, NC 27104
- Beds: 3 | Baths: 2.5 | Square feet: 1,890
- Beds: 3 | Baths: 2 | Square feet: 2,133
540 N Stratford Rd, Winston Salem, NC 27104
- Beds: 5 | Baths: 4.5 | Square feet: 5,465
Median sale price: $450,000 | Median days on market: 35 days
1201 Cliffspring Ct, Winston Salem, NC 27104
- Beds: 4 | Baths: 3.5 | Square feet: 3,678
5005 Marble Arch Rd, Winston Salem, NC 27104
- Beds: 3 | Baths: 2.5 | Square feet: 2,358
900 Brintonial Way, Winston Salem, NC 27104
- Beds: 3 | Baths: 2.5 | Square feet: 2,531