Most expensive homes for sale in Pittsfield
Written by:
November 17, 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. 39 Lexington Pkwy, Pittsfield
- Price: $559,000
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,574
- Price per square foot: $217
- Lot size: 0.2 acres
- Days on market: 66 days (-$15,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,574
- Price per square foot: $217
- Lot size: 0.2 acres
- Days on market: 66 days (-$15,000 price reduction since listing)
- View listing on realtor.com
#29. 57 Palomino Dr, Pittsfield
- Price: $569,000
- 5 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,907
- Price per square foot: $195
- Lot size: 1.0 acres
- Days on market: 11 days
- View listing on realtor.com
- 5 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,907
- Price per square foot: $195
- Lot size: 1.0 acres
- Days on market: 11 days
- View listing on realtor.com
#28. 35 Chapman Rd, Pittsfield
- Price: $570,000
- 2 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 1,814
- Price per square foot: $314
- Lot size: 9.8 acres
- Days on market: 83 days (-$10,000 price reduction since listing)
- View listing on realtor.com
- 2 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 1,814
- Price per square foot: $314
- Lot size: 9.8 acres
- Days on market: 83 days (-$10,000 price reduction since listing)
- View listing on realtor.com
#27. 847 West St, Pittsfield
- Price: $574,900
- 3 bedrooms, 1 full bathrooms, 1 half bathroom
- Square feet: 2,076
- Price per square foot: $276
- Lot size: 0.4 acres
- Days on market: 16 days
- View listing on realtor.com
- 3 bedrooms, 1 full bathrooms, 1 half bathroom
- Square feet: 2,076
- Price per square foot: $276
- Lot size: 0.4 acres
- Days on market: 16 days
- View listing on realtor.com
#26. 100 Northumberland Rd, Pittsfield
- Price: $579,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,008
- Price per square foot: $192
- Lot size: 0.4 acres
- Days on market: 24 days (-$38,100 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,008
- Price per square foot: $192
- Lot size: 0.4 acres
- Days on market: 24 days (-$38,100 price reduction since listing)
- View listing on realtor.com
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#25. 14 Alpine Trl Unit 14, Pittsfield
- Price: $589,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,296
- Price per square foot: $178
- Days on market: 195 days (-$36,000 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: $178
- Days on market: 195 days (-$36,000 price reduction since listing)
- View listing on realtor.com
#24. 4 Filomena Dr, Pittsfield
- Price: $599,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,464
- Price per square foot: $243
- Lot size: 0.6 acres
- Days on market: 245 days (-$20,900 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: $243
- Lot size: 0.6 acres
- Days on market: 245 days (-$20,900 price reduction since listing)
- View listing on realtor.com
#23. 2 Amy Ct, Pittsfield
- Price: $599,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,561
- Price per square foot: $168
- Days on market: 9 days
- 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: 9 days
- View listing on realtor.com
#22. 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: 81 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: 81 days (-$30,000 price reduction since listing)
- View listing on realtor.com
#21. 1136 Barker Rd Unit 18, Pittsfield
- Price: $599,900
- 3 bedrooms, 1 full bathrooms, 1 half bathroom
- Square feet: 2,044
- Price per square foot: $293
- Days on market: 18 days
- View listing on realtor.com
- 3 bedrooms, 1 full bathrooms, 1 half bathroom
- Square feet: 2,044
- Price per square foot: $293
- Days on market: 18 days
- View listing on realtor.com
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#20. 304 Dalton Division Rd, Pittsfield
- Price: $600,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,464
- Price per square foot: $243
- Lot size: 6.3 acres
- Days on market: 24 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,464
- Price per square foot: $243
- Lot size: 6.3 acres
- Days on market: 24 days
- View listing on realtor.com
#19. 10 Lillybrook Rd, Pittsfield
- Price: $699,900
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 2,748
- Price per square foot: $254
- Lot size: 1.3 acres
- Days on market: 15 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 2,748
- Price per square foot: $254
- Lot size: 1.3 acres
- Days on market: 15 days
- View listing on realtor.com
#18. 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: 176 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: 176 days (-$35,000 price reduction since listing)
- View listing on realtor.com
#17. 1136 Barker Rd Unit 11, Pittsfield
- Price: $750,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,204
- Price per square foot: $340
- Days on market: 33 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,204
- Price per square foot: $340
- Days on market: 33 days
- View listing on realtor.com
#16. 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: 52 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: 52 days
- View listing on realtor.com
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#15. 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: 308 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 308 days
- View listing on realtor.com
#14. 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: 310 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 310 days
- View listing on realtor.com
#13. 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: 308 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 308 days
- View listing on realtor.com
#12. 5 Aspen Way, Pittsfield
- Price: $799,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 310 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 310 days
- View listing on realtor.com
#11. 69 Gravesleigh Ter, Pittsfield
- Price: $888,800
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,005
- Price per square foot: $295
- Lot size: 0.8 acres
- Days on market: 8 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,005
- Price per square foot: $295
- Lot size: 0.8 acres
- Days on market: 8 days
- View listing on realtor.com
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#10. 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: 40 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: 40 days
- View listing on realtor.com
#9. 619 Lakeway Dr, Pittsfield
- Price: $1,025,000
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,176
- Price per square foot: $471
- Lot size: 0.2 acres
- Days on market: 79 days (-$75,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,176
- Price per square foot: $471
- Lot size: 0.2 acres
- Days on market: 79 days (-$75,000 price reduction since listing)
- View listing on realtor.com
#8. 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: 74 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: 74 days
- View listing on realtor.com
#7. 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: 42 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: 42 days
- View listing on realtor.com
#6. 8 Northbrook Ln, Pittsfield
- Price: $1,199,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,100
- Price per square foot: $386
- Lot size: 2.8 acres
- Days on market: 172 days (-$160,900 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,100
- Price per square foot: $386
- Lot size: 2.8 acres
- Days on market: 172 days (-$160,900 price reduction since listing)
- View listing on realtor.com
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#5. 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: 37 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: 37 days
- View listing on realtor.com
#4. 61 Tor Ct, Pittsfield
- Price: $1,395,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 1,728
- Price per square foot: $807
- Lot size: 1.3 acres
- Days on market: 55 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 1,728
- Price per square foot: $807
- Lot size: 1.3 acres
- Days on market: 55 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: 93 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: 93 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: 88 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: 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: 172 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: 172 days
- View listing on realtor.com
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