Most expensive homes for sale in Winston-Salem

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October 20, 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. 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: 102 days
- View listing on realtor.com

#29. 2960 Reynolds Sq, Winston Salem

- Price: $1,375,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,474
- Price per square foot: $307
- Lot size: 0.2 acres
- Days on market: 34 days
- View listing on realtor.com

#28. 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: 38 days
- View listing on realtor.com

#27. 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: 5 days
- View listing on realtor.com

#26. 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: 2 days
- View listing on realtor.com
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#25. 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: 374 days (-$20,000 price reduction since listing)
- View listing on realtor.com

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

#23. 360 N Stratford Rd, Winston Salem

- Price: $1,495,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,495
- Price per square foot: $332
- Lot size: 1.0 acres
- Days on market: 18 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: 125 days
- View listing on realtor.com

#21. 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: 40 days
- View listing on realtor.com
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#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: 244 days (-$8,000 price reduction since listing)
- View listing on realtor.com

#19. 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: 87 days
- View listing on realtor.com

#18. 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: 135 days
- View listing on realtor.com

#17. 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: 78 days
- View listing on realtor.com

#16. 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: 115 days (-$46,000 price reduction since listing)
- View listing on realtor.com
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#15. 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: 75 days
- View listing on realtor.com

#14. 465 Sheffield Dr, Winston Salem

- Price: $1,695,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,571
- Price per square foot: $304
- Lot size: 0.5 acres
- Days on market: 97 days (-$205,000 price reduction since listing)
- View listing on realtor.com

#13. 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: 39 days
- View listing on realtor.com

#12. 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: 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: 128 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: 177 days
- View listing on realtor.com

#9. 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: 204 days (-$109,000 price reduction since listing)
- View listing on realtor.com

#8. 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: 169 days
- View listing on realtor.com

#7. 768 Royal Jasmine Ct, Winston Salem

- Price: $1,895,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,931
- Price per square foot: $384
- Lot size: 0.4 acres
- Days on market: 25 days
- View listing on realtor.com

#6. 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: 198 days
- View listing on realtor.com
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#5. 1817 Chanterelle Ct, Winston Salem

- Price: $1,999,980
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,408
- Price per square foot: $453
- Lot size: 0.5 acres
- Days on market: 21 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: 184 days (-$100,000 price reduction since listing)
- View listing on realtor.com

#3. 2715 Bartram Rd, Winston Salem

- Price: $2,250,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,069
- Price per square foot: $370
- Lot size: 1.6 acres
- Days on market: 9 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: 123 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: 141 days
- View listing on realtor.com
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