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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.
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#30. 170 Whimsy Ln, Winchester
- Price: $789,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,740
- Price per square foot: $166
- Lot size: 5.0 acres
- Days on market: 25 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,740
- Price per square foot: $166
- Lot size: 5.0 acres
- Days on market: 25 days
- View listing on realtor.com
#29. 184 Williamson Rd, Winchester
- Price: $799,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,220
- Price per square foot: $189
- Lot size: 0.4 acres
- Days on market: 10 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,220
- Price per square foot: $189
- Lot size: 0.4 acres
- Days on market: 10 days
- View listing on realtor.com
#28. 348 Retreat Ln, Winchester
- Price: $799,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 3,726
- Price per square foot: $214
- Lot size: 11.0 acres
- Days on market: 9 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 3,726
- Price per square foot: $214
- Lot size: 11.0 acres
- Days on market: 9 days
- View listing on realtor.com
#27. 518 N Braddock St, Winchester
- Price: $799,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,634
- Price per square foot: $303
- Lot size: 0.2 acres
- Days on market: 33 days (-$40,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,634
- Price per square foot: $303
- Lot size: 0.2 acres
- Days on market: 33 days (-$40,000 price reduction since listing)
- View listing on realtor.com
#26. 127 Triangle Ct, Winchester
- Price: $799,900
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,500
- Price per square foot: $177
- Lot size: 0.3 acres
- Days on market: 44 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,500
- Price per square foot: $177
- Lot size: 0.3 acres
- Days on market: 44 days
- View listing on realtor.com
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#25. 1802 Chestnut Grove Rd, Winchester
- Price: $799,900
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,792
- Price per square foot: $210
- Lot size: 5.5 acres
- Days on market: 27 days (-$30,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,792
- Price per square foot: $210
- Lot size: 5.5 acres
- Days on market: 27 days (-$30,000 price reduction since listing)
- View listing on realtor.com
#24. Oak Dr Lot 5, Winchester
- Price: $799,900
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,056
- Price per square foot: $261
- Lot size: 5.0 acres
- Days on market: 10 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,056
- Price per square foot: $261
- Lot size: 5.0 acres
- Days on market: 10 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: 233 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: 233 days
- View listing on realtor.com
#22. 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: 242 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: 242 days
- View listing on realtor.com
#21. Redbud Rd Lot 6, Winchester
- Price: $818,400
- 4 bedrooms, 4 full bathrooms
- Square feet: 2,368
- Price per square foot: $345
- Lot size: 2.6 acres
- Days on market: 48 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 2,368
- Price per square foot: $345
- Lot size: 2.6 acres
- Days on market: 48 days
- View listing on realtor.com
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#20. 105 Sundial Ct, Winchester
- Price: $825,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,464
- Price per square foot: $184
- Lot size: 0.3 acres
- Days on market: 55 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,464
- Price per square foot: $184
- Lot size: 0.3 acres
- Days on market: 55 days
- View listing on realtor.com
#19. 101 N Washington St, Winchester
- Price: $829,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,888
- Price per square foot: $287
- Lot size: 0.1 acres
- Days on market: 16 days (-$10,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,888
- Price per square foot: $287
- Lot size: 0.1 acres
- Days on market: 16 days (-$10,000 price reduction since listing)
- View listing on realtor.com
#18. 935 Breckinridge Ln, Winchester
- Price: $835,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,342
- Price per square foot: $192
- Lot size: 0.7 acres
- Days on market: 247 days (-$15,000 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: $192
- Lot size: 0.7 acres
- Days on market: 247 days (-$15,000 price reduction since listing)
- View listing on realtor.com
#17. 279 Fishel Rd, Winchester
- Price: $848,400
- 5 bedrooms, 3 full bathrooms
- Square feet: 4,056
- Price per square foot: $209
- Lot size: 2.1 acres
- Days on market: 64 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms
- Square feet: 4,056
- Price per square foot: $209
- Lot size: 2.1 acres
- Days on market: 64 days
- View listing on realtor.com
#16. 840 Carpers Valley Rd, Winchester
- Price: $875,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,888
- Price per square foot: $225
- Lot size: 5.9 acres
- Days on market: 37 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,888
- Price per square foot: $225
- Lot size: 5.9 acres
- Days on market: 37 days
- View listing on realtor.com
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#15. 115 Winterberry Ct, Winchester
- Price: $879,900
- 6 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 9,608
- Price per square foot: $91
- Lot size: 0.5 acres
- Days on market: 171 days (-$19,100 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 9,608
- Price per square foot: $91
- Lot size: 0.5 acres
- Days on market: 171 days (-$19,100 price reduction since listing)
- View listing on realtor.com
#14. 204 Roszel Rd, Winchester
- Price: $894,900
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,125
- Price per square foot: $216
- Lot size: 0.4 acres
- Days on market: 16 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,125
- Price per square foot: $216
- Lot size: 0.4 acres
- Days on market: 16 days
- View listing on realtor.com
#13. 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: 430 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: 430 days
- View listing on realtor.com
#12. 102 S Stewart St, Winchester
- Price: $925,000
- 7 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,049
- Price per square foot: $183
- Lot size: 0.4 acres
- Days on market: 33 days
- View listing on realtor.com
- 7 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,049
- Price per square foot: $183
- Lot size: 0.4 acres
- Days on market: 33 days
- View listing on realtor.com
#11. 154 Windsor Ln, Winchester
- Price: $979,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,412
- Price per square foot: $286
- Lot size: 5.0 acres
- Days on market: 73 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,412
- Price per square foot: $286
- Lot size: 5.0 acres
- Days on market: 73 days
- View listing on realtor.com
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#10. 939 Buckner Dr, Winchester
- Price: $990,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,122
- Price per square foot: $161
- Lot size: 0.4 acres
- Days on market: 9 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,122
- Price per square foot: $161
- Lot size: 0.4 acres
- Days on market: 9 days
- View listing on realtor.com
#9. 1321 Vanceright Cir, Winchester
- Price: $995,000
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,793
- Price per square foot: $262
- Lot size: 0.7 acres
- Days on market: 142 days (-$105,000 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,793
- Price per square foot: $262
- Lot size: 0.7 acres
- Days on market: 142 days (-$105,000 price reduction since listing)
- View listing on realtor.com
#8. 874 Carpers Valley Rd, Winchester
- Price: $999,900
- 4 bedrooms, 2 full bathrooms
- Square feet: 3,216
- Price per square foot: $310
- Lot size: 45.3 acres
- Days on market: 37 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms
- Square feet: 3,216
- Price per square foot: $310
- Lot size: 45.3 acres
- Days on market: 37 days
- View listing on realtor.com
#7. 1004 Heth Pl, Winchester
- Price: $1,249,000
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 5,184
- Price per square foot: $240
- Lot size: 0.4 acres
- Days on market: 191 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 5,184
- Price per square foot: $240
- Lot size: 0.4 acres
- Days on market: 191 days
- View listing on realtor.com
#6. 255 White Rd, Winchester
- Price: $1,349,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,529
- Price per square foot: $243
- Lot size: 30.5 acres
- Days on market: 222 days (-$40,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,529
- Price per square foot: $243
- Lot size: 30.5 acres
- Days on market: 222 days (-$40,000 price reduction since listing)
- View listing on realtor.com
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#5. 1960 Great Mountain Ln, Winchester
- Price: $1,350,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,434
- Price per square foot: $554
- Lot size: 96.4 acres
- Days on market: 46 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,434
- Price per square foot: $554
- Lot size: 96.4 acres
- Days on market: 46 days
- View listing on realtor.com
#4. 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: 215 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: 215 days
- View listing on realtor.com
#3. 407 S Washington St, Winchester
- Price: $1,599,999
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,474
- Price per square foot: $247
- Lot size: 1.0 acres
- Days on market: 45 days
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,474
- Price per square foot: $247
- Lot size: 1.0 acres
- Days on market: 45 days
- View listing on realtor.com
#2. 202 S Washington St, Winchester
- Price: $1,600,000
- 7 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,616
- Price per square foot: $185
- Lot size: 0.3 acres
- Days on market: 108 days
- View listing on realtor.com
- 7 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,616
- Price per square foot: $185
- Lot size: 0.3 acres
- Days on market: 108 days
- View listing on realtor.com
#1. 2361 Indian Hollow Rd, Winchester
- Price: $2,500,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,297
- Price per square foot: $581
- Lot size: 93.0 acres
- Days on market: 264 days (-$1,000,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,297
- Price per square foot: $581
- Lot size: 93.0 acres
- Days on market: 264 days (-$1,000,000 price reduction since listing)
- View listing on realtor.com
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Homes for sale in Winchester at every price point
