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Most expensive homes for sale in Winchester
Stacker compiled a list of the most expensive homes in Winchester listed for sale on realtor.com. Homes are ranked by price with ties broken by price per square foot.
#30. 229 Taggart Dr, Winchester
- Price: $787,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,958
- Price per square foot: $198
- Lot size: 0.3 acres
- Days on market: 40 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,958
- Price per square foot: $198
- Lot size: 0.3 acres
- Days on market: 40 days
- View listing on realtor.com
#29. 237 Estate Dr, Winchester
- Price: $789,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,510
- Price per square foot: $314
- Lot size: 11.7 acres
- Days on market: 21 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,510
- Price per square foot: $314
- Lot size: 11.7 acres
- Days on market: 21 days
- View listing on realtor.com
#28. 0-A Adams Rd, Winchester
- Price: $789,900
- 3 bedrooms, 2 full bathrooms
- Square feet: 1,801
- Price per square foot: $438
- Lot size: 10.0 acres
- Days on market: 18 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 1,801
- Price per square foot: $438
- Lot size: 10.0 acres
- Days on market: 18 days
- View listing on realtor.com
#27. 439 N Braddock St, Winchester
- Price: $795,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,874
- Price per square foot: $276
- Lot size: 0.3 acres
- Days on market: 49 days (-$44,000 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,874
- Price per square foot: $276
- Lot size: 0.3 acres
- Days on market: 49 days (-$44,000 price reduction since listing)
- View listing on realtor.com
#26. 137 Regency Lakes Dr, Winchester
- Price: $799,000
- 3 bedrooms, 1 full bathrooms
- Square feet: 1,199
- Price per square foot: $666
- Lot size: 3.8 acres
- Days on market: 201 days
- View listing on realtor.com
- 3 bedrooms, 1 full bathrooms
- Square feet: 1,199
- Price per square foot: $666
- Lot size: 3.8 acres
- Days on market: 201 days
- View listing on realtor.com
#25. 504 Marion St, Winchester
- Price: $799,900
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,453
- Price per square foot: $146
- Lot size: 1.0 acres
- Days on market: 9 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,453
- Price per square foot: $146
- Lot size: 1.0 acres
- Days on market: 9 days
- View listing on realtor.com
#24. 147 Simmons Ridge Ln, Winchester
- Price: $799,900
- 5 bedrooms, 3 full bathrooms
- Square feet: 2,800
- Price per square foot: $285
- Lot size: 5.1 acres
- Days on market: 242 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms
- Square feet: 2,800
- Price per square foot: $285
- Lot size: 5.1 acres
- Days on market: 242 days
- View listing on realtor.com
#23. 283 Fishel Rd, Winchester
- Price: $799,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,700
- Price per square foot: $296
- Lot size: 2.1 acres
- Days on market: 30 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,700
- Price per square foot: $296
- Lot size: 2.1 acres
- Days on market: 30 days
- View listing on realtor.com
#22. 231 Simmons Ridge Ln, Winchester
- Price: $799,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,685
- Price per square foot: $297
- Lot size: 5.0 acres
- Days on market: 250 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,685
- Price per square foot: $297
- Lot size: 5.0 acres
- Days on market: 250 days
- View listing on realtor.com
#21. Trojan Ln Lot 14, Winchester
- Price: $802,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,211
- Price per square foot: $362
- Lot size: 7.1 acres
- Days on market: 39 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,211
- Price per square foot: $362
- Lot size: 7.1 acres
- Days on market: 39 days
- View listing on realtor.com
#20. 1910 Harvest Dr, Winchester
- Price: $826,500
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,292
- Price per square foot: $192
- Lot size: 0.2 acres
- Days on market: 73 days (-$22,500 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,292
- Price per square foot: $192
- Lot size: 0.2 acres
- Days on market: 73 days (-$22,500 price reduction since listing)
- View listing on realtor.com
#19. 192 Tuscarora Rd, Winchester
- Price: $839,000
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,662
- Price per square foot: $179
- Lot size: 14.3 acres
- Days on market: 10 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,662
- Price per square foot: $179
- Lot size: 14.3 acres
- Days on market: 10 days
- View listing on realtor.com
#18. 114 Carroll Ridge Ln, Winchester
- Price: $860,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,220
- Price per square foot: $267
- Lot size: 4.2 acres
- Days on market: 31 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,220
- Price per square foot: $267
- Lot size: 4.2 acres
- Days on market: 31 days
- View listing on realtor.com
#17. 166 Whistlewood Ln, Winchester
- Price: $865,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,260
- Price per square foot: $265
- Lot size: 2.0 acres
- Days on market: 8 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,260
- Price per square foot: $265
- Lot size: 2.0 acres
- Days on market: 8 days
- View listing on realtor.com
#16. 935 Breckinridge Ln, Winchester
- Price: $897,500
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,342
- Price per square foot: $206
- Lot size: 0.7 acres
- Days on market: 44 days (-$22,500 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,342
- Price per square foot: $206
- Lot size: 0.7 acres
- Days on market: 44 days (-$22,500 price reduction since listing)
- View listing on realtor.com
#15. 281 Fishel Rd, Winchester
- Price: $899,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $290
- Lot size: 3.1 acres
- Days on market: 227 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $290
- Lot size: 3.1 acres
- Days on market: 227 days
- View listing on realtor.com
#14. 290 Fromans Rd, Winchester
- Price: $899,900
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,500
- Price per square foot: $359
- Lot size: 20.0 acres
- Days on market: 32 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,500
- Price per square foot: $359
- Lot size: 20.0 acres
- Days on market: 32 days
- View listing on realtor.com
#13. Siler Rd, Winchester
- Price: $899,900
- 3 bedrooms, 2 full bathrooms
- Square feet: 1,762
- Price per square foot: $510
- Lot size: 29.5 acres
- Days on market: 174 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 1,762
- Price per square foot: $510
- Lot size: 29.5 acres
- Days on market: 174 days
- View listing on realtor.com
#12. 211 Whistlewood Ln, Winchester
- Price: $899,990
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,716
- Price per square foot: $190
- Days on market: 2 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,716
- Price per square foot: $190
- Days on market: 2 days
- View listing on realtor.com
#11. 191 Simmons Ridge Ln, Winchester
- Price: $900,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,185
- Price per square foot: $173
- Lot size: 5.0 acres
- Days on market: 244 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,185
- Price per square foot: $173
- Lot size: 5.0 acres
- Days on market: 244 days
- View listing on realtor.com
#10. 1018 Heth Pl, Winchester
- Price: $1,130,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,692
- Price per square foot: $198
- Lot size: 0.5 acres
- Days on market: 157 days (-$20,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,692
- Price per square foot: $198
- Lot size: 0.5 acres
- Days on market: 157 days (-$20,000 price reduction since listing)
- View listing on realtor.com
#9. 1581 Great Mountain Ln, Winchester
- Price: $1,350,000
- 5 bedrooms, 4 full bathrooms
- Square feet: 3,272
- Price per square foot: $412
- Lot size: 96.4 acres
- Days on market: 26 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms
- Square feet: 3,272
- Price per square foot: $412
- Lot size: 96.4 acres
- Days on market: 26 days
- View listing on realtor.com
#8. Rotz Ct, Winchester
- Price: $1,379,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,124
- Price per square foot: $441
- Lot size: 2.0 acres
- Days on market: 230 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,124
- Price per square foot: $441
- Lot size: 2.0 acres
- Days on market: 230 days
- View listing on realtor.com
#7. 255 White Rd, Winchester
- Price: $1,499,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,900
- Price per square foot: $254
- Lot size: 30.0 acres
- Days on market: 19 days
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,900
- Price per square foot: $254
- Lot size: 30.0 acres
- Days on market: 19 days
- View listing on realtor.com
#6. 821, Winchester
- Price: $1,500,000
- 3 bedrooms, 2 full bathrooms
- Square feet: not available
- Price per square foot: not available
- Lot size: 2.5 acres
- Days on market: 12 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: not available
- Price per square foot: not available
- Lot size: 2.5 acres
- Days on market: 12 days
- View listing on realtor.com
#5. 3372 Hunting Ridge Rd, Winchester
- Price: $1,582,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,344
- Price per square foot: $674
- Lot size: 6.6 acres
- Days on market: 207 days (-$5,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,344
- Price per square foot: $674
- Lot size: 6.6 acres
- Days on market: 207 days (-$5,000 price reduction since listing)
- View listing on realtor.com
#4. 778 Johnston Ct, Winchester
- Price: $1,600,000
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 10,500
- Price per square foot: $152
- Lot size: 1.4 acres
- Days on market: 32 days (-$50,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 10,500
- Price per square foot: $152
- Lot size: 1.4 acres
- Days on market: 32 days (-$50,000 price reduction since listing)
- View listing on realtor.com
#3. 143 Fox Meadow Ln, Winchester
- Price: $2,500,000
- 4 bedrooms, 3 full bathrooms, 3 half bathrooms
- Square feet: 8,589
- Price per square foot: $291
- Lot size: 17.3 acres
- Days on market: 5 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 3 half bathrooms
- Square feet: 8,589
- Price per square foot: $291
- Lot size: 17.3 acres
- Days on market: 5 days
- View listing on realtor.com
#2. 134 Hawthorne Dr, Winchester
- Price: $3,495,000
- 5 bedrooms, 5 full bathrooms, 5 half bathrooms
- Square feet: 9,824
- Price per square foot: $355
- Lot size: 4.1 acres
- Days on market: 30 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 5 half bathrooms
- Square feet: 9,824
- Price per square foot: $355
- Lot size: 4.1 acres
- Days on market: 30 days
- View listing on realtor.com
#1. 2361 Indian Hollow Rd, Winchester
- Price: $3,500,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,297
- Price per square foot: $814
- Lot size: 215.0 acres
- Days on market: 61 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,297
- Price per square foot: $814
- Lot size: 215.0 acres
- Days on market: 61 days
- View listing on realtor.com
