Most expensive homes for sale in Winchester
Written by:
April 15, 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. 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: 149 days
- View listing on realtor.com
- 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: 149 days
- View listing on realtor.com
#29. 320 Angus Hill Ln, Winchester
- Price: $840,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,567
- Price per square foot: $235
- Lot size: 11.9 acres
- Days on market: 9 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,567
- Price per square foot: $235
- Lot size: 11.9 acres
- Days on market: 9 days
- View listing on realtor.com
#28. 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: 225 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: 225 days
- View listing on realtor.com
#27. 501 Princess Ct, Winchester
- Price: $859,900
- 5 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 4,242
- Price per square foot: $202
- Lot size: 0.4 acres
- Days on market: 30 days
- View listing on realtor.com
- 5 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 4,242
- Price per square foot: $202
- Lot size: 0.4 acres
- Days on market: 30 days
- View listing on realtor.com
#26. 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: 74 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: 74 days
- View listing on realtor.com
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#25. 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: 17 days
- View listing on realtor.com
- 2 bedrooms, 2 full bathrooms
- Square feet: 1,600
- Price per square foot: $556
- Lot size: 99.8 acres
- Days on market: 17 days
- View listing on realtor.com
#24. 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: 214 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: 214 days
- View listing on realtor.com
#23. 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: 26 days
- 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: 26 days
- View listing on realtor.com
#22. 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: 50 days
- View listing on realtor.com
- 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: 50 days
- View listing on realtor.com
#21. 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: 149 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: 149 days
- View listing on realtor.com
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#20. 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: 73 days (-$40,010 price reduction since listing)
- View listing on realtor.com
- 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: 73 days (-$40,010 price reduction since listing)
- View listing on realtor.com
#19. 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: 87 days (-$80,000 price reduction since listing)
- View listing on realtor.com
- 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: 87 days (-$80,000 price reduction since listing)
- View listing on realtor.com
#18. 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: 41 days
- View listing on realtor.com
- 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: 41 days
- View listing on realtor.com
#17. 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: 40 days
- View listing on realtor.com
- 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: 40 days
- View listing on realtor.com
#16. 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: 51 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,363
- Price per square foot: $279
- Lot size: 0.6 acres
- Days on market: 51 days
- View listing on realtor.com
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#15. 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: 22 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms
- Square feet: 4,700
- Price per square foot: $211
- Lot size: 5.5 acres
- Days on market: 22 days
- View listing on realtor.com
#14. 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: 303 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: 303 days (-$105,000 price reduction since listing)
- View listing on realtor.com
#13. 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: 129 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: 129 days
- View listing on realtor.com
#12. 1869 Clayton Ridge Dr, Winchester
- Price: $1,110,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,780
- Price per square foot: $232
- Lot size: 1.8 acres
- Days on market: 26 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,780
- Price per square foot: $232
- Lot size: 1.8 acres
- Days on market: 26 days
- View listing on realtor.com
#11. 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: 15 days
- View listing on realtor.com
- 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: 15 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: 42 days
- View listing on realtor.com
- 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: 42 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: 207 days (-$55,000 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,434
- Price per square foot: $532
- Lot size: 96.4 acres
- Days on market: 207 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: 6 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,949
- Price per square foot: $262
- Lot size: 27.6 acres
- Days on market: 6 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: 103 days (-$90,000 price reduction since listing)
- View listing on realtor.com
- 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: 103 days (-$90,000 price reduction since listing)
- View listing on realtor.com
#6. 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: 32 days
- View listing on realtor.com
- 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: 32 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: 269 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: 269 days (-$35,000 price reduction since listing)
- 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: 376 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: 376 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: 32 days
- View listing on realtor.com
- 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: 32 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: 60 days
- View listing on realtor.com
- 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: 60 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: 102 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: 102 days
- View listing on realtor.com
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