Most expensive homes for sale in Winston-Salem

Written by:
November 17, 2025
scarp577 // Shutterstock

Most expensive homes for sale in Winston-Salem

Stacker compiled a list of the most expensive homes in Winston-Salem listed for sale on realtor.com. Homes are ranked by price with ties broken by price per square foot.

#30. 3054 Scarlet Tanager Dr, Winston Salem

- Price: $1,190,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,346
- Price per square foot: $355
- Lot size: 0.3 acres
- Days on market: 44 days
- View listing on realtor.com

#29. 620 Walkertown Guthrie Rd, Winston Salem

- Price: $1,195,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,229
- Price per square foot: $191
- Lot size: 5.5 acres
- Days on market: 114 days (-$55,000 price reduction since listing)
- View listing on realtor.com

#28. 1831 Angelo St, Winston Salem

- Price: $1,199,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,123
- Price per square foot: $383
- Lot size: 1.1 acres
- Days on market: 72 days (-$100,000 price reduction since listing)
- View listing on realtor.com

#27. 5005 Marble Arch Rd, Winston Salem

- Price: $1,200,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,253
- Price per square foot: $228
- Lot size: 0.8 acres
- Days on market: 183 days
- View listing on realtor.com

#26. 3061 Scarlet Tanager Dr, Winston Salem

- Price: $1,250,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,017
- Price per square foot: $311
- Lot size: 0.4 acres
- Days on market: 326 days
- View listing on realtor.com

#25. 2960 Reynolds Sq, Winston Salem

- Price: $1,279,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,474
- Price per square foot: $285
- Lot size: 0.2 acres
- Days on market: 76 days (-$96,000 price reduction since listing)
- View listing on realtor.com

#24. 100 Muirfield Dr, Winston Salem

- Price: $1,299,000
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,580
- Price per square foot: $362
- Lot size: 0.2 acres
- Days on market: 80 days
- View listing on realtor.com

#23. 3814 Pine Wood Lake Dr, Winston Salem

- Price: $1,334,030
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,441
- Price per square foot: $300
- Lot size: 0.3 acres
- Days on market: 242 days
- View listing on realtor.com

#22. 1341 Maple Chase Ln, Winston Salem

- Price: $1,350,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,037
- Price per square foot: $334
- Lot size: 0.2 acres
- Days on market: 198 days
- View listing on realtor.com

#21. 236 Glade View Ct, Winston Salem

- Price: $1,370,400
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,818
- Price per square foot: $358
- Lot size: 0.1 acres
- Days on market: 144 days
- View listing on realtor.com

#20. 409 Brookberry Farm Cir, Winston Salem

- Price: $1,375,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,206
- Price per square foot: $326
- Lot size: 0.2 acres
- Days on market: 80 days
- View listing on realtor.com

#19. 1021 Kent Mews Ct, Winston Salem

- Price: $1,390,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,168
- Price per square foot: $268
- Lot size: 1.1 acres
- Days on market: 47 days
- View listing on realtor.com

#18. 744 Royal Jasmine Ct, Winston Salem

- Price: $1,395,000
- 5 bedrooms, 4 full bathrooms
- Square feet: 3,888
- Price per square foot: $358
- Lot size: 0.3 acres
- Days on market: 221 days
- View listing on realtor.com

#17. 2805 Old Town Club Rd, Winston Salem

- Price: $1,400,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,266
- Price per square foot: $328
- Lot size: 0.9 acres
- Days on market: 44 days
- View listing on realtor.com

#16. 1199 Maple Chase Ln, Winston Salem

- Price: $1,400,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,222
- Price per square foot: $331
- Lot size: 0.3 acres
- Days on market: 416 days (-$20,000 price reduction since listing)
- View listing on realtor.com

#15. 1223 Maple Chase Ln, Winston Salem

- Price: $1,490,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,213
- Price per square foot: $353
- Lot size: 0.4 acres
- Days on market: 66 days
- View listing on realtor.com

#14. 465 Sheffield Dr, Winston Salem

- Price: $1,495,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,571
- Price per square foot: $268
- Lot size: 0.5 acres
- Days on market: 139 days (-$200,000 price reduction since listing)
- View listing on realtor.com

#13. 1517 Audubon Village Dr, Winston Salem

- Price: $1,495,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,757
- Price per square foot: $314
- Lot size: 0.4 acres
- Days on market: 167 days
- View listing on realtor.com

#12. 2840 Reynolds Dr, Winston Salem

- Price: $1,525,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,192
- Price per square foot: $293
- Lot size: 0.6 acres
- Days on market: 5 days
- View listing on realtor.com

#11. 4009 Rolling Knoll Cv, Winston Salem

- Price: $1,579,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,123
- Price per square foot: $382
- Lot size: 1.1 acres
- Days on market: 286 days (-$8,000 price reduction since listing)
- View listing on realtor.com

#10. 774 Royal Jasmine Ct, Winston Salem

- Price: $1,589,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,094
- Price per square foot: $388
- Lot size: 0.3 acres
- Days on market: 129 days
- View listing on realtor.com

#9. 433 Brookberry Farm Cir, Winston Salem

- Price: $1,595,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,930
- Price per square foot: $323
- Lot size: 0.4 acres
- Days on market: 177 days
- View listing on realtor.com

#8. 4141 Shattalon Dr, Winston Salem

- Price: $1,649,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,900
- Price per square foot: $279
- Lot size: 6.8 acres
- Days on market: 117 days
- View listing on realtor.com

#7. 101 N Avalon Rd, Winston Salem

- Price: $1,695,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,009
- Price per square foot: $422
- Lot size: 0.3 acres
- Days on market: 46 days
- View listing on realtor.com

#6. 1020 W Kent Rd, Winston Salem

- Price: $1,800,000
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 6,619
- Price per square foot: $271
- Lot size: 2.3 acres
- Days on market: 11 days
- View listing on realtor.com

#5. 540 N Stratford Rd, Winston Salem

- Price: $1,890,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,465
- Price per square foot: $345
- Lot size: 0.4 acres
- Days on market: 246 days (-$109,000 price reduction since listing)
- View listing on realtor.com

#4. 804 Royal Jasmine Ct, Winston Salem

- Price: $1,890,000
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,654
- Price per square foot: $406
- Lot size: 0.4 acres
- Days on market: 211 days
- View listing on realtor.com

#3. 1817 Chanterelle Ct, Winston Salem

- Price: $1,899,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,408
- Price per square foot: $430
- Lot size: 0.5 acres
- Days on market: 63 days (-$50,980 price reduction since listing)
- View listing on realtor.com

#2. 762 Royal Jasmine Ct, Winston Salem

- Price: $1,931,681
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,541
- Price per square foot: $425
- Lot size: 0.4 acres
- Days on market: 27 days
- View listing on realtor.com

#1. 1067 E Kent Rd, Winston Salem

- Price: $6,500,000
- 6 bedrooms, 8 full bathrooms, 5 half bathrooms
- Square feet: 21,081
- Price per square foot: $308
- Lot size: 7.2 acres
- Days on market: 183 days
- View listing on realtor.com

Trending Now