Most expensive homes for sale in Winston-Salem

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July 7, 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. 2792 Fieldwood Ct, Winston Salem

- Price: $1,300,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,694
- Price per square foot: $276
- Lot size: 0.7 acres
- Days on market: 10 days
- View listing on realtor.com

#29. 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: 228 days (-$100,000 price reduction since listing)
- View listing on realtor.com

#28. 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: 255 days
- View listing on realtor.com

#27. 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: 95 days
- View listing on realtor.com

#26. 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: 114 days
- View listing on realtor.com

#25. 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: 121 days (-$25,000 price reduction since listing)
- View listing on realtor.com

#24. 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: 51 days
- View listing on realtor.com

#23. 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: 269 days
- View listing on realtor.com

#22. 1517 Audubon Village Dr, Winston Salem

- Price: $1,495,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,296
- Price per square foot: $453
- Lot size: 0.4 acres
- Days on market: 20 days
- View listing on realtor.com

#21. 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: 543 days (-$100,000 price reduction since listing)
- View listing on realtor.com

#20. 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: 139 days (-$8,000 price reduction since listing)
- View listing on realtor.com

#19. 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: 53 days
- View listing on realtor.com

#18. 2840 Reynolds Dr, Winston Salem

- Price: $1,595,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,192
- Price per square foot: $307
- Lot size: 0.6 acres
- Days on market: 20 days (-$100,000 price reduction since listing)
- View listing on realtor.com

#17. 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: 30 days
- View listing on realtor.com

#16. 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: 51 days
- View listing on realtor.com

#15. 786 Royal Jasmine Ct, Winston Salem

- Price: $1,649,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,328
- Price per square foot: $381
- Lot size: 0.3 acres
- Days on market: 17 days
- View listing on realtor.com

#14. 4141 Shattalon Dr, Winston Salem

- Price: $1,675,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,900
- Price per square foot: $283
- Lot size: 6.8 acres
- Days on market: 6 days
- View listing on realtor.com

#13. 505 Stonegate Ln, Winston Salem

- Price: $1,695,000
- 6 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 8,603
- Price per square foot: $197
- Lot size: 2.0 acres
- Days on market: 10 days
- View listing on realtor.com

#12. 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: 72 days
- View listing on realtor.com

#11. 2990 Reynolds Sq, Winston Salem

- Price: $1,880,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,133
- Price per square foot: $366
- Lot size: 0.2 acres
- Days on market: 23 days (-$115,000 price reduction since listing)
- View listing on realtor.com

#10. 1596 Yelton Ln, Winston Salem

- Price: $1,950,000
- 10 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,106
- Price per square foot: $319
- Lot size: 20.0 acres
- Days on market: 156 days (-$550,000 price reduction since listing)
- View listing on realtor.com

#9. 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: 27 days
- View listing on realtor.com

#8. 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: 93 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: 99 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: 24 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: 108 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: 79 days (-$50,000 price reduction since listing)
- View listing on realtor.com

#3. 2725 Windsor Rd, Winston Salem

- Price: $2,875,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,213
- Price per square foot: $350
- Lot size: 1.3 acres
- Days on market: 48 days
- View listing on realtor.com

#2. 2632 Bartram Pl, Winston Salem

- Price: $3,995,000
- 3 bedrooms, 3 full bathrooms, 3 half bathrooms
- Square feet: 4,957
- Price per square foot: $805
- Lot size: 2.0 acres
- Days on market: 18 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: 19,574
- Price per square foot: $332
- Lot size: 7.2 acres
- Days on market: 36 days
- View listing on realtor.com

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