Most Expensive Homes for Sale in Winchester

#30. 422 Canyon Rd, Winchester

- Price: $769,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,132
- Price per square foot: $149
- Lot size: 0.3 acres
- Days on market: 11 days
- View listing on realtor.com

#29. 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: 38 days
- View listing on realtor.com

#28. 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: 100 days
- View listing on realtor.com

#27. 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: 114 days
- 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: 149 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: 93 days
- View listing on realtor.com

#24. 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: 115 days
- View listing on realtor.com

#23. 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: 135 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: 55 days
- View listing on realtor.com

#21. 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: 153 days
- View listing on realtor.com

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#20. 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

#19. 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: 160 days
- View listing on realtor.com

#18. Oak Dr Lot 7, Winchester

- Price: $829,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,700
- Price per square foot: $307
- Lot size: 5.0 acres
- Days on market: 93 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: 169 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: 18 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: 158 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: 93 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: 535 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: 17 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: 66 days
- View listing on realtor.com

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#10. 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: 31 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: 247 days (-$105,000 price reduction since listing)
- View listing on realtor.com

#8. 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: 73 days
- View listing on realtor.com

#7. 1960 Great Mountain Ln, Winchester

- Price: $1,295,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,434
- Price per square foot: $532
- Lot size: 96.4 acres
- Days on market: 151 days (-$55,000 price reduction since listing)
- View listing on realtor.com

#6. 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: 213 days (-$35,000 price reduction since listing)
- View listing on realtor.com

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#5. 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: 85 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: 320 days
- View listing on realtor.com

#3. 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: 47 days
- View listing on realtor.com

#2. 103 Oak Ridge Ln, Winchester

- Price: $1,699,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 9,447
- Price per square foot: $179
- Lot size: 1.6 acres
- Days on market: 4 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: 46 days
- View listing on realtor.com

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Most expensive homes for sale in Winchester