Most expensive homes for sale in Winchester

Written by:
December 16, 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.

#1. 1631 Back Mountain Rd, Winchester
- Price: $2,125,000
- 5 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 4,166
- Price per square foot: $510
- Lot size: 180.1 acres
- Days on market: 55 days
- View listing on realtor.com

#2. 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: 80 days
- View listing on realtor.com

#3. Honeycrisp Way Lot 18, Winchester
- Price: $1,485,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,484
- Price per square foot: $426
- Lot size: 5.0 acres
- Days on market: 27 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: 62 days
- View listing on realtor.com

#5. 207 W View Dr, Winchester
- Price: $1,115,000
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,180
- Price per square foot: $266
- Lot size: 6.6 acres
- Days on market: 26 days
- View listing on realtor.com

#6. Keval Gyan Way Lot 1, Winchester
- Price: $1,099,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,800
- Price per square foot: $189
- Lot size: 3.2 acres
- Days on market: 4 days
- View listing on realtor.com

#7. 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: 233 days
- View listing on realtor.com

#8. 410 Valley View Dr, Winchester
- Price: $1,095,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,426
- Price per square foot: $201
- Lot size: 9.8 acres
- Days on market: 147 days (-$34,000 price reduction since listing)
- View listing on realtor.com

#9. Gravenstein Ct Lot 60, Winchester
- Price: $1,045,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,875
- Price per square foot: $363
- Lot size: 2.4 acres
- Days on market: 269 days (-$75,000 price reduction since listing)
- View listing on realtor.com

#10. 2225 Cedar Grove Rd, 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: 126 days
- View listing on realtor.com

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