
Most expensive homes for sale in Winchester
Written by:
February 11, 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. 206 Crossing Paths Ln, Winchester
- Price: $789,500
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,787
- Price per square foot: $283
- Lot size: 7.5 acres
- Days on market: 31 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,787
- Price per square foot: $283
- Lot size: 7.5 acres
- Days on market: 31 days
- View listing on realtor.com
#29. Covey Lot 2, Winchester
- Price: $789,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: not available
- Price per square foot: not available
- Lot size: 2.6 acres
- Days on market: 93 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: not available
- Price per square foot: not available
- Lot size: 2.6 acres
- Days on market: 93 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: 107 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: 107 days
- View listing on realtor.com
#27. 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: 142 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: 142 days
- View listing on realtor.com
#26. 181 Oak Dr, 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: 108 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: 108 days
- View listing on realtor.com
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#25. 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: 86 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: 86 days
- View listing on realtor.com
#24. 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: 86 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: 86 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: 331 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: 331 days
- View listing on realtor.com
#22. 2850 Cedar Creek Grade, Winchester
- Price: $799,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,500
- Price per square foot: $319
- Lot size: 5.0 acres
- Days on market: 128 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,500
- Price per square foot: $319
- Lot size: 5.0 acres
- Days on market: 128 days
- View listing on realtor.com
#21. 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: 48 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: 48 days
- View listing on realtor.com
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#20. 953 Redbud Rd, 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: 146 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: 146 days
- View listing on realtor.com
#19. 117 Pawn Ct, Winchester
- Price: $819,999
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,420
- Price per square foot: $185
- Days on market: 3 days (-$16,000 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: $185
- Days on market: 3 days (-$16,000 price reduction since listing)
- View listing on realtor.com
#18. 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: 153 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: 153 days
- 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: 162 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: 162 days
- View listing on realtor.com
#16. 111 Sundial Ct, Winchester
- Price: $880,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,363
- Price per square foot: $201
- Days on market: 11 days
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,363
- Price per square foot: $201
- Days on market: 11 days
- View listing on realtor.com
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#15. 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: 151 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: 151 days
- View listing on realtor.com
#14. 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: 86 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: 86 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: 528 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: 528 days
- View listing on realtor.com
#12. 939 Buckner Dr, Winchester
- Price: $940,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,122
- Price per square foot: $153
- Lot size: 0.4 acres
- Days on market: 10 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,122
- Price per square foot: $153
- Lot size: 0.4 acres
- Days on market: 10 days
- View listing on realtor.com
#11. Liza Kates Ln Lot 13, Winchester
- Price: $949,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $306
- Lot size: 11.3 acres
- Days on market: 12 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $306
- Lot size: 11.3 acres
- Days on market: 12 days
- View listing on realtor.com
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#10. 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: 59 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: 59 days
- View listing on realtor.com
#9. 270 Widener Dr, Winchester
- Price: $980,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,544
- Price per square foot: $215
- Lot size: 2.9 acres
- Days on market: 24 days
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,544
- Price per square foot: $215
- Lot size: 2.9 acres
- Days on market: 24 days
- View listing on realtor.com
#8. 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: 240 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: 240 days (-$105,000 price reduction since listing)
- View listing on realtor.com
#7. 3372 Hunting Ridge Rd, Winchester
- Price: $995,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,919
- Price per square foot: $340
- Lot size: 6.6 acres
- Days on market: 66 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,919
- Price per square foot: $340
- Lot size: 6.6 acres
- Days on market: 66 days
- View listing on realtor.com
#6. 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: 144 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: 144 days
- 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: 206 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: 206 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: 78 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: 78 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: 313 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: 313 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: 40 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: 40 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: 39 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: 39 days
- View listing on realtor.com
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