Most expensive homes for sale in Pittsfield
Written by:
September 29, 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. 68 Brookside Dr, Pittsfield
- Price: $589,900
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,646
- Price per square foot: $222
- Lot size: 1.0 acres
- Days on market: 72 days (-$30,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,646
- Price per square foot: $222
- Lot size: 1.0 acres
- Days on market: 72 days (-$30,000 price reduction since listing)
- View listing on realtor.com
#29. 2 Amy Ct Unit 2, Pittsfield
- Price: $599,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,561
- Price per square foot: $168
- Days on market: 46 days (-$30,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,561
- Price per square foot: $168
- Days on market: 46 days (-$30,000 price reduction since listing)
- View listing on realtor.com
#28. 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: 210 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: 210 days (-$15,000 price reduction since listing)
- View listing on realtor.com
#27. 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: 160 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: 160 days (-$67,000 price reduction since listing)
- View listing on realtor.com
#26. 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: 58 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: 58 days
- View listing on realtor.com
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#25. 25 E New Lenox Rd, Pittsfield
- Price: $675,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,462
- Price per square foot: $274
- Lot size: 1.0 acres
- Days on market: 19 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,462
- Price per square foot: $274
- Lot size: 1.0 acres
- Days on market: 19 days
- View listing on realtor.com
#24. 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: 121 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: 121 days (-$24,000 price reduction since listing)
- View listing on realtor.com
#23. 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: 141 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: 141 days (-$35,000 price reduction since listing)
- View listing on realtor.com
#22. 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: 164 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: 164 days (-$46,000 price reduction since listing)
- View listing on realtor.com
#21. 23 Aspen Way, Pittsfield
- Price: $749,900
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,600
- Price per square foot: $208
- Days on market: 17 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,600
- Price per square foot: $208
- Days on market: 17 days
- View listing on realtor.com
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#20. 103 Alpine Trl, Pittsfield
- Price: $759,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,381
- Price per square foot: $318
- Days on market: 17 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,381
- Price per square foot: $318
- Days on market: 17 days
- View listing on realtor.com
#19. 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: 275 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 275 days
- View listing on realtor.com
#18. 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: 273 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 273 days
- View listing on realtor.com
#17. 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: 273 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 273 days
- View listing on realtor.com
#16. 5 Aspen Way, Pittsfield
- Price: $799,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 275 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 275 days
- View listing on realtor.com
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#15. 5 Crofut St, Pittsfield
- Price: $889,900
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,370
- Price per square foot: $264
- Lot size: 0.3 acres
- Days on market: 5 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,370
- Price per square foot: $264
- Lot size: 0.3 acres
- Days on market: 5 days
- View listing on realtor.com
#14. 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: 58 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: 58 days
- View listing on realtor.com
#13. 19 Aspen Way, Pittsfield
- Price: $965,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 4,024
- Price per square foot: $239
- Days on market: 142 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: 142 days (-$24,000 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: 39 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: 39 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: 44 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: 44 days
- View listing on realtor.com
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#10. 1020 Cascade St, Pittsfield
- Price: $1,170,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,662
- Price per square foot: $439
- Lot size: 19.2 acres
- Days on market: 7 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,662
- Price per square foot: $439
- Lot size: 19.2 acres
- Days on market: 7 days
- View listing on realtor.com
#9. 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: 199 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: 199 days (-$5,100 price reduction since listing)
- View listing on realtor.com
#8. 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: 830 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: 830 days
- View listing on realtor.com
#7. 65 Crofut St, Pittsfield
- Price: $1,350,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,948
- Price per square foot: $272
- Lot size: 2.5 acres
- Days on market: 2 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,948
- Price per square foot: $272
- Lot size: 2.5 acres
- Days on market: 2 days
- View listing on realtor.com
#6. 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: 58 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: 58 days
- View listing on realtor.com
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#5. 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: 137 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: 137 days
- View listing on realtor.com
#4. 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: 135 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: 135 days
- View listing on realtor.com
#3. 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: 58 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: 58 days
- View listing on realtor.com
#2. 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: 53 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: 53 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: 137 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: 137 days
- View listing on realtor.com
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