Most expensive homes for sale in Winchester
Written by:
January 7, 2025
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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. 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: 72 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: 72 days
- View listing on realtor.com
#29. 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: 107 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: 107 days
- View listing on realtor.com
#28. 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: 90 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: 90 days (-$30,000 price reduction since listing)
- View listing on realtor.com
#27. Fishel Rd Lot 1A, 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: 51 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: 51 days
- View listing on realtor.com
#26. 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: 73 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: 73 days
- View listing on realtor.com
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#25. Oak Dr Lot 7, Winchester
- Price: $799,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,700
- Price per square foot: $296
- Lot size: 5.0 acres
- Days on market: 51 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: 5.0 acres
- Days on market: 51 days
- View listing on realtor.com
#24. 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: 296 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: 296 days
- View listing on realtor.com
#23. 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: 305 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: 305 days
- View listing on realtor.com
#22. 303 Summerfield Dr, Winchester
- Price: $807,883
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,200
- Price per square foot: $252
- Lot size: 0.3 acres
- Days on market: 13 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,200
- Price per square foot: $252
- Lot size: 0.3 acres
- Days on market: 13 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: 111 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: 111 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: 118 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: 118 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: 79 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: 79 days (-$10,000 price reduction since listing)
- View listing on realtor.com
#18. 117 Pawn Ct, Winchester
- Price: $835,999
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,420
- Price per square foot: $189
- Days on market: 3 days (-$6,194 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,420
- Price per square foot: $189
- Days on market: 3 days (-$6,194 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: 127 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: 127 days
- View listing on realtor.com
#16. 219 Taggart Dr, Winchester
- Price: $898,400
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,675
- Price per square foot: $244
- Lot size: 0.3 acres
- Days on market: 116 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,675
- Price per square foot: $244
- Lot size: 0.3 acres
- Days on market: 116 days
- View listing on realtor.com
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#15. 102 S Stewart St, Winchester
- Price: $899,000
- 7 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,049
- Price per square foot: $178
- Lot size: 0.4 acres
- Days on market: 96 days (-$26,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,049
- Price per square foot: $178
- Lot size: 0.4 acres
- Days on market: 96 days (-$26,000 price reduction since listing)
- View listing on realtor.com
#14. 154 Windsor Ln, Winchester
- Price: $899,900
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,412
- Price per square foot: $263
- Lot size: 5.0 acres
- Days on market: 136 days (-$79,100 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,412
- Price per square foot: $263
- Lot size: 5.0 acres
- Days on market: 136 days (-$79,100 price reduction since listing)
- View listing on realtor.com
#13. Fishel Rd Lot 1B, Winchester
- Price: $899,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $290
- Lot size: 5.0 acres
- Days on market: 51 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: 5.0 acres
- Days on market: 51 days
- View listing on realtor.com
#12. 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: 493 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: 493 days
- View listing on realtor.com
#11. 610 Stonymeade Dr, Winchester
- Price: $975,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,812
- Price per square foot: $167
- Lot size: 3.7 acres
- Days on market: 24 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,812
- Price per square foot: $167
- Lot size: 3.7 acres
- Days on market: 24 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: 72 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: 72 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: 205 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: 205 days (-$105,000 price reduction since listing)
- View listing on realtor.com
#8. 3372 Hunting Ridge Rd, Winchester
- Price: $995,000
- 2 bedrooms, 2 full bathrooms
- Square feet: 2,919
- Price per square foot: $340
- Lot size: 6.6 acres
- Days on market: 31 days
- View listing on realtor.com
- 2 bedrooms, 2 full bathrooms
- Square feet: 2,919
- Price per square foot: $340
- Lot size: 6.6 acres
- Days on market: 31 days
- View listing on realtor.com
#7. 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: 109 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: 109 days
- View listing on realtor.com
#6. 407 S Washington St, Winchester
- Price: $1,375,000
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,474
- Price per square foot: $212
- Lot size: 1.0 acres
- Days on market: 108 days (-$75,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,474
- Price per square foot: $212
- Lot size: 1.0 acres
- Days on market: 108 days (-$75,000 price reduction since listing)
- View listing on realtor.com
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#5. 202 S Washington St, Winchester
- Price: $1,490,000
- 7 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,616
- Price per square foot: $172
- Lot size: 0.3 acres
- Days on market: 171 days (-$35,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,616
- Price per square foot: $172
- Lot size: 0.3 acres
- Days on market: 171 days (-$35,000 price reduction since listing)
- View listing on realtor.com
#4. 778 Johnston Ct, Winchester
- Price: $1,499,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 10,500
- Price per square foot: $142
- Lot size: 1.4 acres
- Days on market: 43 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 10,500
- Price per square foot: $142
- Lot size: 1.4 acres
- Days on market: 43 days
- View listing on realtor.com
#3. 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: 278 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: 278 days
- View listing on realtor.com
#2. 207 Westview Dr, Winchester
- Price: $1,500,000
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,600
- Price per square foot: $227
- Lot size: 6.6 acres
- Days on market: 5 days
- View listing on realtor.com
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,600
- Price per square foot: $227
- Lot size: 6.6 acres
- Days on market: 5 days
- View listing on realtor.com
#1. 908 Cedar Creek Grade, Winchester
- Price: $2,150,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 7,190
- Price per square foot: $299
- Lot size: 2.6 acres
- Days on market: 4 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 7,190
- Price per square foot: $299
- Lot size: 2.6 acres
- Days on market: 4 days
- View listing on realtor.com
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