Most Expensive Homes for Sale in Winchester

#30. 373 Greenfield Dr, Winchester

- Price: $850,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,612
- Price per square foot: $235
- Lot size: 8.0 acres
- Days on market: 0:00:00
- View listing on realtor.com

#29. 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: 95 days
- View listing on realtor.com

#28. 400 Great Mountain Ln, Winchester

- Price: $890,000
- 2 bedrooms, 2 full bathrooms
- Square feet: 1,600
- Price per square foot: $556
- Lot size: 99.8 acres
- Days on market: 38 days
- View listing on realtor.com

#27. 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: 235 days
- View listing on realtor.com

#26. 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: 47 days
- View listing on realtor.com

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#25. 707 Kennedy Dr, Winchester

- Price: $899,900
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,987
- Price per square foot: $180
- Lot size: 0.8 acres
- Days on market: 71 days
- View listing on realtor.com

#24. 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: 170 days
- View listing on realtor.com

#23. 939 Buckner Dr, Winchester

- Price: $899,990
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,122
- Price per square foot: $147
- Lot size: 0.4 acres
- Days on market: 6 days
- View listing on realtor.com

#22. 270 Widener Dr, Winchester

- Price: $900,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,544
- Price per square foot: $198
- Lot size: 2.9 acres
- Days on market: 108 days (-$80,000 price reduction since listing)
- View listing on realtor.com

#21. 172 Winding Hill Rd, Winchester

- Price: $925,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,107
- Price per square foot: $297
- Lot size: 9.1 acres
- Days on market: 62 days
- View listing on realtor.com

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#20. 1A Fishel Rd, Winchester

- Price: $929,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $299
- Lot size: 5.0 acres
- Days on market: 61 days
- View listing on realtor.com

#19. 113 Shockey Cir, Winchester

- Price: $939,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,363
- Price per square foot: $279
- Lot size: 0.6 acres
- Days on market: 72 days
- View listing on realtor.com

#18. 3372 Hunting Ridge Rd, Winchester

- Price: $950,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,919
- Price per square foot: $325
- Lot size: 6.6 acres
- Days on market: 10 days
- View listing on realtor.com

#17. 1321 Vanceright Cir, Winchester

- Price: $970,800
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,793
- Price per square foot: $255
- Lot size: 0.7 acres
- Days on market: 324 days (-$24,200 price reduction since listing)
- View listing on realtor.com

#16. 304 Longview Ln, Winchester

- Price: $995,000
- 5 bedrooms, 3 full bathrooms
- Square feet: 4,700
- Price per square foot: $211
- Lot size: 5.5 acres
- Days on market: 43 days
- View listing on realtor.com

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#15. Gravenstein Ct Lot 60, Winchester

- Price: $1,045,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,750
- Price per square foot: $380
- Lot size: 2.4 acres
- Days on market: 43 days (-$75,000 price reduction since listing)
- View listing on realtor.com

#14. Gravenstein Ct Lot 62, Winchester

- Price: $1,095,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,707
- Price per square foot: $295
- Lot size: 2.4 acres
- Days on market: 7 days
- View listing on realtor.com

#13. 700 Miller Rd, Winchester

- Price: $1,165,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,058
- Price per square foot: $230
- Lot size: 2.5 acres
- Days on market: 36 days
- View listing on realtor.com

#12. 191 Old Baltimore Rd, Winchester

- Price: $1,175,000
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,414
- Price per square foot: $183
- Lot size: 2.8 acres
- Days on market: 16 days
- View listing on realtor.com

#11. 331 N Braddock St, Winchester

- Price: $1,199,997
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 6,517
- Price per square foot: $184
- Lot size: 0.2 acres
- Days on market: 13 days
- View listing on realtor.com

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#10. 788 Johnston Ct, Winchester

- Price: $1,265,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 8,070
- Price per square foot: $156
- Lot size: 0.9 acres
- Days on market: 63 days
- View listing on realtor.com

#9. 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: 228 days (-$55,000 price reduction since listing)
- View listing on realtor.com

#8. 1460 Pitcock Ln, Winchester

- Price: $1,299,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,949
- Price per square foot: $262
- Lot size: 27.6 acres
- Days on market: 27 days
- View listing on realtor.com

#7. 207 Westview Dr, Winchester

- Price: $1,359,000
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,600
- Price per square foot: $205
- Lot size: 6.6 acres
- Days on market: 124 days (-$90,000 price reduction since listing)
- View listing on realtor.com

#6. 202 S Washington St, Winchester

- Price: $1,390,000
- 7 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,616
- Price per square foot: $161
- Lot size: 0.3 acres
- Days on market: 290 days (-$100,000 price reduction since listing)
- View listing on realtor.com

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#5. 118 Saint Andrews Ct, Winchester

- Price: $1,429,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,716
- Price per square foot: $212
- Lot size: 5.0 acres
- Days on market: 53 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: 397 days
- View listing on realtor.com

#3. 291 Lake Serene Dr, Winchester

- Price: $1,595,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,754
- Price per square foot: $277
- Lot size: 1.3 acres
- Days on market: 53 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: 81 days
- View listing on realtor.com

#1. 908 Cedar Creek Grade, Winchester

- Price: $2,098,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 7,190
- Price per square foot: $291
- Lot size: 2.6 acres
- Days on market: 123 days (-$52,000 price reduction since listing)
- View listing on realtor.com

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Most expensive homes for sale in Winchester