Most expensive homes for sale in Winston-Salem
Written by:
September 8, 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.
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#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: 80 days
- View listing on realtor.com
- 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: 80 days
- View listing on realtor.com
#29. 268 S Pine Valley Rd, Winston Salem
- Price: $1,320,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,240
- Price per square foot: $251
- Lot size: 0.7 acres
- Days on market: 51 days (-$65,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,240
- Price per square foot: $251
- Lot size: 0.7 acres
- Days on market: 51 days (-$65,000 price reduction since listing)
- View listing on realtor.com
#28. 791 Linden Green Way, Winston Salem
- Price: $1,324,900
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,083
- Price per square foot: $429
- Lot size: 0.4 acres
- Days on market: 18 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,083
- Price per square foot: $429
- Lot size: 0.4 acres
- Days on market: 18 days
- View listing on realtor.com
#27. 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: 325 days
- View listing on realtor.com
- 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: 325 days
- View listing on realtor.com
#26. 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: 165 days
- View listing on realtor.com
- 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: 165 days
- View listing on realtor.com
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#25. 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: 121 days
- View listing on realtor.com
- 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: 121 days
- View listing on realtor.com
#24. 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: 67 days
- View listing on realtor.com
- 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: 67 days
- View listing on realtor.com
#23. 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: 3 days
- View listing on realtor.com
- 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: 3 days
- View listing on realtor.com
#22. 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: 613 days (-$110,000 price reduction since listing)
- View listing on realtor.com
- 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: 613 days (-$110,000 price reduction since listing)
- View listing on realtor.com
#21. 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: 339 days (-$20,000 price reduction since listing)
- View listing on realtor.com
- 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: 339 days (-$20,000 price reduction since listing)
- View listing on realtor.com
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#20. 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: 90 days
- View listing on realtor.com
- 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: 90 days
- View listing on realtor.com
#19. 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
- 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
#18. 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: 209 days (-$8,000 price reduction since listing)
- View listing on realtor.com
- 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: 209 days (-$8,000 price reduction since listing)
- View listing on realtor.com
#17. 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: 52 days
- View listing on realtor.com
- 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: 52 days
- View listing on realtor.com
#16. 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: 100 days
- View listing on realtor.com
- 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: 100 days
- View listing on realtor.com
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#15. 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: 43 days
- View listing on realtor.com
- 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: 43 days
- View listing on realtor.com
#14. 505 Stonegate Ln, Winston Salem
- Price: $1,649,000
- 6 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 8,603
- Price per square foot: $191
- Lot size: 2.0 acres
- Days on market: 80 days (-$46,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 8,603
- Price per square foot: $191
- Lot size: 2.0 acres
- Days on market: 80 days (-$46,000 price reduction since listing)
- View listing on realtor.com
#13. 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: 40 days
- View listing on realtor.com
- 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: 40 days
- View listing on realtor.com
#12. 2570 Club Park Rd, Winston Salem
- Price: $1,695,000
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 4,355
- Price per square foot: $389
- Lot size: 1.4 acres
- Days on market: 4 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 4,355
- Price per square foot: $389
- Lot size: 1.4 acres
- Days on market: 4 days
- View listing on realtor.com
#11. 2990 Reynolds Sq, Winston Salem
- Price: $1,795,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,133
- Price per square foot: $349
- Lot size: 0.2 acres
- Days on market: 93 days (-$85,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,133
- Price per square foot: $349
- Lot size: 0.2 acres
- Days on market: 93 days (-$85,000 price reduction since listing)
- View listing on realtor.com
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#10. 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: 142 days
- View listing on realtor.com
- 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: 142 days
- View listing on realtor.com
#9. 465 Sheffield Dr, Winston Salem
- Price: $1,900,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,571
- Price per square foot: $341
- Lot size: 0.5 acres
- Days on market: 62 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,571
- Price per square foot: $341
- Lot size: 0.5 acres
- Days on market: 62 days
- View listing on realtor.com
#8. 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: 226 days (-$550,000 price reduction since listing)
- View listing on realtor.com
- 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: 226 days (-$550,000 price reduction since listing)
- View listing on realtor.com
#7. 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: 163 days
- View listing on realtor.com
- 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: 163 days
- View listing on realtor.com
#6. 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: 169 days
- View listing on realtor.com
- 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: 169 days
- View listing on realtor.com
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#5. 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: 94 days
- View listing on realtor.com
- 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: 94 days
- View listing on realtor.com
#4. 3560 Kirklees Rd, Winston Salem
- Price: $2,000,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 5,829
- Price per square foot: $343
- Lot size: 1.9 acres
- Days on market: 149 days (-$100,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 5,829
- Price per square foot: $343
- Lot size: 1.9 acres
- Days on market: 149 days (-$100,000 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: 118 days
- View listing on realtor.com
- 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: 118 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: 88 days
- View listing on realtor.com
- 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: 88 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: 106 days
- View listing on realtor.com
- 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: 106 days
- View listing on realtor.com
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