Most expensive homes for sale in Pittsfield
Written by:
August 25, 2025
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Most expensive homes for sale in Pittsfield
Stacker compiled a list of the most expensive homes in Pittsfield listed for sale on realtor.com. Homes are ranked by price with ties broken by price per square foot.
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#30. 35 Chapman Rd, Pittsfield
- Price: $595,000
- 2 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 1,814
- Price per square foot: $328
- Lot size: 9.8 acres
- Days on market: 13 days
- View listing on realtor.com
- 2 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 1,814
- Price per square foot: $328
- Lot size: 9.8 acres
- Days on market: 13 days
- View listing on realtor.com
#29. 24 Alpine Trl, Pittsfield
- Price: $599,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,081
- Price per square foot: $194
- Days on market: 89 days (-$30,500 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,081
- Price per square foot: $194
- Days on market: 89 days (-$30,500 price reduction since listing)
- View listing on realtor.com
#28. 68 Brookside Dr, Pittsfield
- Price: $619,900
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,646
- Price per square foot: $234
- Lot size: 1.0 acres
- Days on market: 37 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,646
- Price per square foot: $234
- Lot size: 1.0 acres
- Days on market: 37 days
- View listing on realtor.com
#27. 4 Filomena Dr, Pittsfield
- Price: $619,900
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,464
- Price per square foot: $251
- Lot size: 0.6 acres
- Days on market: 175 days (-$15,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,464
- Price per square foot: $251
- Lot size: 0.6 acres
- Days on market: 175 days (-$15,000 price reduction since listing)
- View listing on realtor.com
#26. 14 Alpine Trl Unit 14, Pittsfield
- Price: $625,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,296
- Price per square foot: $189
- Days on market: 125 days (-$67,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,296
- Price per square foot: $189
- Days on market: 125 days (-$67,000 price reduction since listing)
- View listing on realtor.com
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#25. 2 Amy Ct Unit 2, Pittsfield
- Price: $629,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,561
- Price per square foot: $176
- Days on market: 11 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,561
- Price per square foot: $176
- Days on market: 11 days
- View listing on realtor.com
#24. 225 Karen Dr, Pittsfield
- Price: $649,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,240
- Price per square foot: $289
- Lot size: 1.2 acres
- Days on market: 23 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,240
- Price per square foot: $289
- Lot size: 1.2 acres
- Days on market: 23 days
- View listing on realtor.com
#23. 10 Lillybrook Rd, Pittsfield
- Price: $724,000
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 2,748
- Price per square foot: $263
- Lot size: 1.3 acres
- Days on market: 352 days (-$20,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 2,748
- Price per square foot: $263
- Lot size: 1.3 acres
- Days on market: 352 days (-$20,000 price reduction since listing)
- View listing on realtor.com
#22. 26 Filomena Dr, Pittsfield
- Price: $725,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,491
- Price per square foot: $207
- Lot size: 0.6 acres
- Days on market: 86 days (-$24,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,491
- Price per square foot: $207
- Lot size: 0.6 acres
- Days on market: 86 days (-$24,000 price reduction since listing)
- View listing on realtor.com
#21. 33 Alpine Trl, Pittsfield
- Price: $730,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,381
- Price per square foot: $215
- Days on market: 106 days (-$35,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,381
- Price per square foot: $215
- Days on market: 106 days (-$35,000 price reduction since listing)
- View listing on realtor.com
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#20. 40 Commonwealth Ave, Pittsfield
- Price: $749,000
- 5 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 4,078
- Price per square foot: $183
- Lot size: 0.4 acres
- Days on market: 129 days (-$46,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 4,078
- Price per square foot: $183
- Lot size: 0.4 acres
- Days on market: 129 days (-$46,000 price reduction since listing)
- View listing on realtor.com
#19. 15 Cherry Hill Dr Lot 12, Pittsfield
- Price: $799,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 238 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 238 days
- View listing on realtor.com
#18. 5 Aspen Way Lot 17, Pittsfield
- Price: $799,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 240 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 240 days
- View listing on realtor.com
#17. 5 Aspen Way, Pittsfield
- Price: $799,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 240 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 240 days
- View listing on realtor.com
#16. 15 Cherry Hill Dr, Pittsfield
- Price: $799,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 238 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 238 days
- View listing on realtor.com
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#15. 127 Alpine Trl, Pittsfield
- Price: $939,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,700
- Price per square foot: $253
- Days on market: 23 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,700
- Price per square foot: $253
- Days on market: 23 days
- View listing on realtor.com
#14. 19 Aspen Way, Pittsfield
- Price: $965,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 4,024
- Price per square foot: $239
- Days on market: 107 days (-$24,000 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 4,024
- Price per square foot: $239
- Days on market: 107 days (-$24,000 price reduction since listing)
- View listing on realtor.com
#13. 68 Colt Rd, Pittsfield
- Price: $995,000
- 6 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,198
- Price per square foot: $191
- Lot size: 0.8 acres
- Days on market: 90 days (-$105,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,198
- Price per square foot: $191
- Lot size: 0.8 acres
- Days on market: 90 days (-$105,000 price reduction since listing)
- View listing on realtor.com
#12. 89 Crofut St, Pittsfield
- Price: $1,100,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,128
- Price per square foot: $179
- Lot size: 1.2 acres
- Days on market: 4 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,128
- Price per square foot: $179
- Lot size: 1.2 acres
- Days on market: 4 days
- View listing on realtor.com
#11. 619 Lakeway Dr, Pittsfield
- Price: $1,100,000
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,176
- Price per square foot: $505
- Lot size: 0.2 acres
- Days on market: 9 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,176
- Price per square foot: $505
- Lot size: 0.2 acres
- Days on market: 9 days
- View listing on realtor.com
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#10. 18 Old Farm Ln, Pittsfield
- Price: $1,189,900
- 5 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,087
- Price per square foot: $385
- Lot size: 2.1 acres
- Days on market: 164 days (-$5,100 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,087
- Price per square foot: $385
- Lot size: 2.1 acres
- Days on market: 164 days (-$5,100 price reduction since listing)
- View listing on realtor.com
#9. Westbrook Ter Lot 140, Pittsfield
- Price: $1,200,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,409
- Price per square foot: $352
- Lot size: 1.2 acres
- Days on market: 795 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,409
- Price per square foot: $352
- Lot size: 1.2 acres
- Days on market: 795 days
- View listing on realtor.com
#8. 411 E New Lenox Rd, Pittsfield
- Price: $1,359,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 4,010
- Price per square foot: $338
- Lot size: 28.2 acres
- Days on market: 23 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 4,010
- Price per square foot: $338
- Lot size: 28.2 acres
- Days on market: 23 days
- View listing on realtor.com
#7. 8 Northbrook Ln, Pittsfield
- Price: $1,399,900
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,100
- Price per square foot: $451
- Lot size: 2.8 acres
- Days on market: 102 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,100
- Price per square foot: $451
- Lot size: 2.8 acres
- Days on market: 102 days
- View listing on realtor.com
#6. Eastbrook Ln Lot 144, Pittsfield
- Price: $1,399,900
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,100
- Price per square foot: $451
- Lot size: 1.1 acres
- Days on market: 100 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,100
- Price per square foot: $451
- Lot size: 1.1 acres
- Days on market: 100 days
- View listing on realtor.com
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#5. 37 Old Farm Ln, Pittsfield
- Price: $1,450,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,978
- Price per square foot: $364
- Lot size: 1.1 acres
- Days on market: 142 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,978
- Price per square foot: $364
- Lot size: 1.1 acres
- Days on market: 142 days
- View listing on realtor.com
#4. 593 Lakeway Dr, Pittsfield
- Price: $1,595,000
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,043
- Price per square foot: $524
- Lot size: 0.8 acres
- Days on market: 23 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,043
- Price per square foot: $524
- Lot size: 0.8 acres
- Days on market: 23 days
- View listing on realtor.com
#3. 122 Blythewood Dr, Pittsfield
- Price: $1,999,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 3,091
- Price per square foot: $646
- Lot size: 1.2 acres
- Days on market: 18 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 3,091
- Price per square foot: $646
- Lot size: 1.2 acres
- Days on market: 18 days
- View listing on realtor.com
#2. 1030 West St, Pittsfield
- Price: $2,250,000
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,477
- Price per square foot: $410
- Lot size: 6.0 acres
- Days on market: 88 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,477
- Price per square foot: $410
- Lot size: 6.0 acres
- Days on market: 88 days
- View listing on realtor.com
#1. 140 Hancock Rd, Pittsfield
- Price: $5,499,500
- 8 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 6,986
- Price per square foot: $787
- Lot size: 1.1 acres
- Days on market: 102 days
- View listing on realtor.com
- 8 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 6,986
- Price per square foot: $787
- Lot size: 1.1 acres
- Days on market: 102 days
- View listing on realtor.com
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