Most expensive homes for sale in Winchester
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March 25, 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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People from these metros are looking to buy homes in Winchester
#30. 117 Pawn Ct, Winchester
- Price: $799,999
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,450
- Price per square foot: $179
- Lot size: 0.3 acres
- Days on market: 76 days (-$20,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,450
- Price per square foot: $179
- Lot size: 0.3 acres
- Days on market: 76 days (-$20,000 price reduction since listing)
- View listing on realtor.com
#29. 100 Abrams Pointe Blvd, Winchester
- Price: $799,999
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,230
- Price per square foot: $189
- Lot size: 0.3 acres
- Days on market: 193 days (-$50,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,230
- Price per square foot: $189
- Lot size: 0.3 acres
- Days on market: 193 days (-$50,000 price reduction since listing)
- View listing on realtor.com
#28. 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: 188 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: 188 days
- View listing on realtor.com
#27. 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: 128 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: 128 days
- View listing on realtor.com
#26. 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: 204 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: 204 days
- View listing on realtor.com
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#25. 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: 9 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: 9 days
- View listing on realtor.com
#24. 3980 Middle Rd, Winchester
- Price: $865,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,504
- Price per square foot: $246
- Lot size: 4.2 acres
- Days on market: 17 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,504
- Price per square foot: $246
- Lot size: 4.2 acres
- Days on market: 17 days
- View listing on realtor.com
#23. 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: 53 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: 53 days
- View listing on realtor.com
#22. 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: 193 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: 193 days
- View listing on realtor.com
#21. 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: 5 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: 5 days
- View listing on realtor.com
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#20. 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: 29 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: 29 days
- View listing on realtor.com
#19. 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: 128 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: 128 days
- View listing on realtor.com
#18. 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: 66 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: 66 days (-$80,000 price reduction since listing)
- View listing on realtor.com
#17. 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: 20 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: 20 days
- View listing on realtor.com
#16. 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: 19 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: 19 days
- View listing on realtor.com
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#15. 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: 30 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: 30 days
- View listing on realtor.com
#14. 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: 52 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: 52 days
- View listing on realtor.com
#13. 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: 1 day
- 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: 1 day
- View listing on realtor.com
#12. 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: 282 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: 282 days (-$105,000 price reduction since listing)
- View listing on realtor.com
#11. 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: 108 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: 108 days
- View listing on realtor.com
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#10. 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: 5 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: 5 days
- View listing on realtor.com
#9. 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: 21 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: 21 days
- View listing on realtor.com
#8. 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: 186 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: 186 days (-$55,000 price reduction since listing)
- View listing on realtor.com
#7. 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: 11 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: 11 days
- View listing on realtor.com
#6. 207 Westview Dr, Winchester
- Price: $1,449,000
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,600
- Price per square foot: $219
- Lot size: 6.6 acres
- Days on market: 82 days (-$51,000 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: $219
- Lot size: 6.6 acres
- Days on market: 82 days (-$51,000 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: 248 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: 248 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: 355 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: 355 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: 11 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: 11 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: 39 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: 39 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: 81 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: 81 days
- View listing on realtor.com
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