Most expensive homes for sale in Pittsfield
Written by:
August 11, 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. 121 Wendell Ave, Pittsfield
- Price: $539,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,145
- Price per square foot: $251
- Lot size: 0.2 acres
- Days on market: 91 days (-$50,000 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,145
- Price per square foot: $251
- Lot size: 0.2 acres
- Days on market: 91 days (-$50,000 price reduction since listing)
- View listing on realtor.com
#29. 144 Bromback St, Pittsfield
- Price: $565,900
- 8 bedrooms, 3 full bathrooms
- Square feet: 4,034
- Price per square foot: $140
- Lot size: 0.3 acres
- Days on market: 76 days
- View listing on realtor.com
- 8 bedrooms, 3 full bathrooms
- Square feet: 4,034
- Price per square foot: $140
- Lot size: 0.3 acres
- Days on market: 76 days
- View listing on realtor.com
#28. 25 Alpine Trl, Pittsfield
- Price: $609,900
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 2,994
- Price per square foot: $203
- Days on market: 71 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 2,994
- Price per square foot: $203
- Days on market: 71 days
- View listing on realtor.com
#27. 304 Dalton Division Rd, Pittsfield
- Price: $610,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,464
- Price per square foot: $247
- Lot size: 6.3 acres
- Days on market: 158 days (-$5,000 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: $247
- Lot size: 6.3 acres
- Days on market: 158 days (-$5,000 price reduction since listing)
- View listing on realtor.com
#26. 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: 9 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: 9 days
- View listing on realtor.com
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#25. 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: 147 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: 147 days (-$15,000 price reduction since listing)
- View listing on realtor.com
#24. 24 Alpine Trl, Pittsfield
- Price: $629,500
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,081
- Price per square foot: $204
- Days on market: 61 days (-$45,500 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: $204
- Days on market: 61 days (-$45,500 price reduction since listing)
- View listing on realtor.com
#23. 24 Alpine Trl Unit 24, Pittsfield
- Price: $629,500
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,081
- Price per square foot: $204
- Days on market: 33 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,081
- Price per square foot: $204
- Days on market: 33 days
- View listing on realtor.com
#22. 83 Hancock Rd, Pittsfield
- Price: $650,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 1,978
- Price per square foot: $328
- Lot size: 2.2 acres
- Days on market: 38 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 1,978
- Price per square foot: $328
- Lot size: 2.2 acres
- Days on market: 38 days
- View listing on realtor.com
#21. 14 Alpine Trl Unit 14, Pittsfield
- Price: $692,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,296
- Price per square foot: $209
- Days on market: 97 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,296
- Price per square foot: $209
- Days on market: 97 days
- View listing on realtor.com
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#20. 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: 58 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: 58 days (-$24,000 price reduction since listing)
- View listing on realtor.com
#19. 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: 78 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: 78 days (-$35,000 price reduction since listing)
- View listing on realtor.com
#18. 10 Lillybrook Rd, Pittsfield
- Price: $744,000
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 2,748
- Price per square foot: $270
- Lot size: 1.3 acres
- Days on market: 324 days (-$15,000 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: $270
- Lot size: 1.3 acres
- Days on market: 324 days (-$15,000 price reduction since listing)
- View listing on realtor.com
#17. 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: 101 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: 101 days (-$46,000 price reduction since listing)
- View listing on realtor.com
#16. 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: 210 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 210 days
- View listing on realtor.com
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#15. 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: 212 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 212 days
- View listing on realtor.com
#14. 5 Aspen Way, Pittsfield
- Price: $799,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 212 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 212 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: 210 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 210 days
- View listing on realtor.com
#12. 1 Pheasant Way, Pittsfield
- Price: $859,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,800
- Price per square foot: $226
- Lot size: 1.0 acres
- Days on market: 180 days (-$36,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,800
- Price per square foot: $226
- Lot size: 1.0 acres
- Days on market: 180 days (-$36,000 price reduction since listing)
- View listing on realtor.com
#11. 19 Aspen Way, Pittsfield
- Price: $965,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 4,024
- Price per square foot: $239
- Days on market: 79 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: 79 days (-$24,000 price reduction since listing)
- View listing on realtor.com
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#10. 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: 62 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: 62 days (-$105,000 price reduction since listing)
- View listing on realtor.com
#9. 18 Old Farm Ln, Pittsfield
- Price: $1,195,000
- 5 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,087
- Price per square foot: $387
- Lot size: 2.1 acres
- Days on market: 136 days (-$94,900 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: $387
- Lot size: 2.1 acres
- Days on market: 136 days (-$94,900 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: 767 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: 767 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: 74 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: 74 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: 72 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: 72 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: 114 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: 114 days
- View listing on realtor.com
#4. 15 Westbrook Ter, Pittsfield
- Price: $1,549,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,830
- Price per square foot: $226
- Lot size: 3.3 acres
- Days on market: 79 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,830
- Price per square foot: $226
- Lot size: 3.3 acres
- Days on market: 79 days
- View listing on realtor.com
#3. 593 Lakeway Dr, Pittsfield
- Price: $1,650,000
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,043
- Price per square foot: $542
- Lot size: 0.8 acres
- Days on market: 62 days (-$150,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,043
- Price per square foot: $542
- Lot size: 0.8 acres
- Days on market: 62 days (-$150,000 price reduction since listing)
- 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: 60 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: 60 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: 74 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: 74 days
- View listing on realtor.com
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