Most expensive homes for sale in Winston-Salem

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June 16, 2025
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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. 5766 Elina Dr, Winston Salem

- Price: $1,258,000
- 5 bedrooms, 4 full bathrooms
- Square feet: 3,644
- Price per square foot: $345
- Lot size: 0.5 acres
- Days on market: 244 days
- View listing on realtor.com

#29. 239 Glade View Ct, Winston Salem

- Price: $1,295,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,101
- Price per square foot: $253
- Lot size: 0.2 acres
- Days on market: 224 days (-$80,000 price reduction since listing)
- View listing on realtor.com

#28. 322 N Avalon Rd, Winston Salem

- Price: $1,295,000
- 5 bedrooms, 4 full bathrooms
- Square feet: 3,957
- Price per square foot: $327
- Lot size: 0.3 acres
- Days on market: 39 days
- View listing on realtor.com

#27. 1009 Windalier Ln, Winston Salem

- Price: $1,300,000
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 4,465
- Price per square foot: $291
- Lot size: 1.4 acres
- Days on market: 114 days
- View listing on realtor.com

#26. 356 Candlewood Dr, Winston Salem

- Price: $1,300,000
- 5 bedrooms, 5 full bathrooms
- Square feet: 1,864
- Price per square foot: $697
- Lot size: 42.9 acres
- Days on market: 207 days (-$100,000 price reduction since listing)
- View listing on realtor.com

#25. 1984 Runnymede Rd, Winston Salem

- Price: $1,325,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,513
- Price per square foot: $293
- Lot size: 0.3 acres
- Days on market: 118 days
- View listing on realtor.com

#24. 4369 Highland Lake Dr, Winston Salem

- Price: $1,332,508
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,156
- Price per square foot: $320
- Lot size: 0.3 acres
- Days on market: 234 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: 74 days
- View listing on realtor.com

#22. 791 Linden Green Way, Winston Salem

- Price: $1,349,900
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,083
- Price per square foot: $437
- Lot size: 0.4 acres
- Days on market: 93 days
- View listing on realtor.com

#21. 4215 Penns Meadow Ln, Winston Salem

- Price: $1,350,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,090
- Price per square foot: $330
- Lot size: 0.6 acres
- Days on market: 100 days (-$25,000 price reduction since listing)
- View listing on realtor.com

#20. 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: 30 days
- View listing on realtor.com

#19. 1199 Maple Chase Ln, Winston Salem

- Price: $1,420,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,222
- Price per square foot: $336
- Lot size: 0.3 acres
- Days on market: 248 days
- View listing on realtor.com

#18. 1021 Kent Mews Ct, Winston Salem

- Price: $1,500,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,168
- Price per square foot: $290
- Lot size: 1.1 acres
- Days on market: 522 days (-$100,000 price reduction since listing)
- View listing on realtor.com

#17. 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: 118 days (-$8,000 price reduction since listing)
- View listing on realtor.com

#16. 123 S Pine Valley Rd, Winston Salem

- Price: $1,595,000
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,674
- Price per square foot: $281
- Lot size: 0.8 acres
- Days on market: 32 days
- View listing on realtor.com

#15. 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: 9 days
- View listing on realtor.com

#14. 3940 Beechridge Rd, Winston Salem

- Price: $1,600,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,964
- Price per square foot: $200
- Lot size: 2.0 acres
- Days on market: 30 days
- View listing on realtor.com

#13. 1510 Charolais Dr, Winston Salem

- Price: $1,615,000
- 5 bedrooms, 5 full bathrooms
- Square feet: 4,515
- Price per square foot: $357
- Lot size: 0.4 acres
- Days on market: 72 days
- View listing on realtor.com

#12. 4141 Shattalon Dr, Winston Salem

- Price: $1,675,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,520
- Price per square foot: $303
- Lot size: 2.0 acres
- Days on market: 234 days (-$300,000 price reduction since listing)
- View listing on realtor.com

#11. 1823 Chanterelle Ct, Winston Salem

- Price: $1,799,900
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,504
- Price per square foot: $399
- Lot size: 0.4 acres
- Days on market: 51 days
- View listing on realtor.com

#10. 2954 Reynolds Sq, Winston Salem

- Price: $1,975,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,932
- Price per square foot: $332
- Lot size: 0.4 acres
- Days on market: 6 days
- View listing on realtor.com

#9. 4620 Cherryhill Ln, Winston Salem

- Price: $1,995,000
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,783
- Price per square foot: $203
- Lot size: 1.8 acres
- Days on market: 72 days
- View listing on realtor.com

#8. 2990 Reynolds Sq, Winston Salem

- Price: $1,995,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,133
- Price per square foot: $388
- Lot size: 0.2 acres
- Days on market: 2 days
- View listing on realtor.com

#7. 540 N Stratford Rd, Winston Salem

- Price: $1,999,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,465
- Price per square foot: $365
- Lot size: 0.4 acres
- Days on market: 78 days
- View listing on realtor.com

#6. 4432 Bent Tree Farm Rd, Winston Salem

- Price: $2,000,000
- 7 bedrooms, 4 full bathrooms, 4 half bathrooms
- Square feet: 9,115
- Price per square foot: $219
- Lot size: 2.7 acres
- Days on market: 3 days
- View listing on realtor.com

#5. 1 Park Vista Ln, Winston Salem

- Price: $2,099,000
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,235
- Price per square foot: $648
- Lot size: 0.4 acres
- Days on market: 87 days
- View listing on realtor.com

#4. 3560 Kirklees Rd, Winston Salem

- Price: $2,100,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 5,829
- Price per square foot: $360
- Lot size: 1.9 acres
- Days on market: 58 days (-$50,000 price reduction since listing)
- View listing on realtor.com

#3. 1596 Yelton Ln, Winston Salem

- Price: $2,500,000
- 10 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,106
- Price per square foot: $409
- Lot size: 20.0 acres
- Days on market: 135 days
- View listing on realtor.com

#2. 2725 Windsor Rd, Winston Salem

- Price: $2,875,000
- 1 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 8,213
- Price per square foot: $350
- Lot size: 1.3 acres
- Days on market: 27 days
- View listing on realtor.com

#1. 1067 E Kent Rd, Winston Salem

- Price: $6,500,000
- 6 bedrooms, 9 full bathrooms, 5 half bathrooms
- Square feet: 21,081
- Price per square foot: $308
- Lot size: 7.2 acres
- Days on market: 15 days
- View listing on realtor.com

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