Most Expensive Homes for Sale in Winchester

#30. 109 Jeni Ct, Winchester

- Price: $799,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,000
- Price per square foot: $199
- Lot size: 0.3 acres
- Days on market: 48 days
- View listing on realtor.com

#29. 2411 Hunting Ridge Rd, Winchester

- Price: $799,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,040
- Price per square foot: $158
- Lot size: 5.1 acres
- Days on market: 41 days (-$25,100 price reduction since listing)
- View listing on realtor.com

#28. 756 Brookneil Dr, Winchester

- Price: $815,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,942
- Price per square foot: $206
- Lot size: 9.0 acres
- Days on market: 103 days (-$34,990 price reduction since listing)
- View listing on realtor.com

#27. 601 Fall Run Ln, Winchester

- Price: $819,950
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,175
- Price per square foot: $376
- Lot size: 20.1 acres
- Days on market: 87 days (-$40 price reduction since listing)
- View listing on realtor.com

#26. 280 Graystone Ln, Winchester

- Price: $830,000
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,549
- Price per square foot: $182
- Lot size: 5.0 acres
- Days on market: 12 days
- View listing on realtor.com

You may also like: The most expensive homes sold in Winchester this year

#25. 1504 Brookdale Ct, Winchester

- Price: $849,990
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,254
- Price per square foot: $161
- Lot size: 0.3 acres
- Days on market: 128 days (-$10,010 price reduction since listing)
- View listing on realtor.com

#24. 1517 Brookdale Ct, Winchester

- Price: $869,500
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,368
- Price per square foot: $136
- Lot size: 0.4 acres
- Days on market: 102 days
- View listing on realtor.com

#23. 254 Whistlewood Ln, Winchester

- Price: $890,000
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 4,301
- Price per square foot: $206
- Lot size: 5.0 acres
- Days on market: 87 days (-$9,000 price reduction since listing)
- View listing on realtor.com

#22. 430 Saddleback Ln, Winchester

- Price: $898,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,532
- Price per square foot: $254
- Lot size: 8.5 acres
- Days on market: 66 days (-$17,000 price reduction since listing)
- View listing on realtor.com

#21. 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: 403 days
- View listing on realtor.com

You may also like: Movies and TV shows casting in Winchester

#20. 769 Seldon Dr, Winchester

- Price: $899,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,438
- Price per square foot: $202
- Lot size: 0.4 acres
- Days on market: 115 days (-$51,000 price reduction since listing)
- 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: 338 days
- View listing on realtor.com

#18. 101 Abrams Pointe Blvd, Winchester

- Price: $899,999
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,280
- Price per square foot: $210
- Lot size: 0.2 acres
- Days on market: 26 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: 229 days
- View listing on realtor.com

#16. 3328 Millwood Pike, Winchester

- Price: $935,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,624
- Price per square foot: $356
- Lot size: 20.5 acres
- Days on market: 57 days
- View listing on realtor.com

You may also like: Best restaurants for 4 cuisines in Winchester

#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: 240 days
- View listing on realtor.com

#14. 150 Ewell Dr, Winchester

- Price: $980,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,256
- Price per square foot: $156
- Lot size: 2.7 acres
- Days on market: 48 days
- View listing on realtor.com

#13. 1020 Breckinridge Ln, Winchester

- Price: $999,000
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,540
- Price per square foot: $152
- Lot size: 0.5 acres
- Days on market: 135 days (-$100,000 price reduction since listing)
- View listing on realtor.com

#12. Cedar Grv Lot 52, Winchester

- Price: $999,999
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $322
- Lot size: 7.7 acres
- Days on market: 68 days
- View listing on realtor.com

#11. Light Rd, Winchester

- Price: $1,012,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,211
- Price per square foot: $457
- Lot size: 15.0 acres
- Days on market: 53 days
- View listing on realtor.com

You may also like: Highest-rated ice cream shops in Winchester by diners

#10. 700 Miller Rd, Winchester

- Price: $1,029,900
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,058
- Price per square foot: $203
- Lot size: 2.5 acres
- Days on market: 204 days (-$45,000 price reduction since listing)
- View listing on realtor.com

#9. 1460 Pitcock Ln, Winchester

- Price: $1,095,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,949
- Price per square foot: $221
- Lot size: 27.6 acres
- Days on market: 195 days (-$30,000 price reduction since listing)
- View listing on realtor.com

#8. 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: 175 days
- View listing on realtor.com

#7. 410 Valley View Dr, Winchester

- Price: $1,148,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,426
- Price per square foot: $211
- Lot size: 9.8 acres
- Days on market: 89 days (-$22,000 price reduction since listing)
- View listing on realtor.com

#6. 207 Westview Dr, Winchester

- Price: $1,149,000
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,380
- Price per square foot: $180
- Lot size: 6.6 acres
- Days on market: 114 days (-$46,000 price reduction since listing)
- View listing on realtor.com

You may also like: Lowest-paying jobs in Winchester

#5. 2321 Cedar Grove Rd, Winchester

- Price: $1,175,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,815
- Price per square foot: $244
- Lot size: 21.0 acres
- Days on market: 38 days
- View listing on realtor.com

#4. 107 Lacosta Ct, Winchester

- Price: $1,175,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,888
- Price per square foot: $302
- Lot size: 2.2 acres
- Days on market: 4 days
- View listing on realtor.com

#3. 291 Lake Serene Dr, Winchester

- Price: $1,299,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,994
- Price per square foot: $260
- Lot size: 1.3 acres
- Days on market: 67 days
- View listing on realtor.com

#2. 731 Apple Pie Ridge Rd, Winchester

- Price: $1,495,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,304
- Price per square foot: $347
- Lot size: 11.4 acres
- Days on market: 62 days (-$255,000 price reduction since listing)
- View listing on realtor.com

#1. 821 Apple Pie Ridge Rd, Winchester

- Price: $1,999,999
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,590
- Price per square foot: $357
- Lot size: 14.5 acres
- Days on market: 22 days
- View listing on realtor.com

You may also like: Highest-paying jobs in Winchester that require a graduate degree

Most expensive homes for sale in Winchester