Most expensive homes for sale in Pittsfield
Written by:
June 30, 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. 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: 29 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: 29 days
- View listing on realtor.com
#29. 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: 116 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: 116 days (-$5,000 price reduction since listing)
- View listing on realtor.com
#28. 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: 90 days (-$20,000 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: $176
- Days on market: 90 days (-$20,000 price reduction since listing)
- View listing on realtor.com
#27. 4 Filomena Dr, Pittsfield
- Price: $634,900
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,464
- Price per square foot: $257
- Lot size: 0.6 acres
- Days on market: 105 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,464
- Price per square foot: $257
- Lot size: 0.6 acres
- Days on market: 105 days
- View listing on realtor.com
#26. 22 Kathy Way, Pittsfield
- Price: $660,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,020
- Price per square foot: $218
- Lot size: 1.0 acres
- Days on market: 54 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,020
- Price per square foot: $218
- Lot size: 1.0 acres
- Days on market: 54 days
- View listing on realtor.com
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#25. 24 Alpine Trl Unit 24, Pittsfield
- Price: $675,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,081
- Price per square foot: $219
- Days on market: 19 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,081
- Price per square foot: $219
- Days on market: 19 days
- View listing on realtor.com
#24. 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: 55 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: 55 days
- View listing on realtor.com
#23. 1136 Barker Rd Unit 66, Pittsfield
- Price: $739,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,124
- Price per square foot: $347
- Days on market: 292 days (-$1,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,124
- Price per square foot: $347
- Days on market: 292 days (-$1,000 price reduction since listing)
- View listing on realtor.com
#22. 26 Filomena Dr, Pittsfield
- Price: $749,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,491
- Price per square foot: $214
- Lot size: 0.6 acres
- Days on market: 16 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,491
- Price per square foot: $214
- Lot size: 0.6 acres
- Days on market: 16 days
- View listing on realtor.com
#21. 10 Lillybrook Rd, Pittsfield
- Price: $759,000
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 2,748
- Price per square foot: $276
- Lot size: 1.3 acres
- Days on market: 282 days (-$40,000 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: $276
- Lot size: 1.3 acres
- Days on market: 282 days (-$40,000 price reduction since listing)
- View listing on realtor.com
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#20. 33 Alpine Trl, Pittsfield
- Price: $765,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,381
- Price per square foot: $226
- Days on market: 36 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,381
- Price per square foot: $226
- Days on market: 36 days
- View listing on realtor.com
#19. 40 Commonwealth Ave, Pittsfield
- Price: $795,000
- 5 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 4,078
- Price per square foot: $194
- Lot size: 0.4 acres
- Days on market: 59 days (-$30,000 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: $194
- Lot size: 0.4 acres
- Days on market: 59 days (-$30,000 price reduction since listing)
- 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: 170 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 170 days
- View listing on realtor.com
#17. 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: 168 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 168 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: 168 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 168 days
- View listing on realtor.com
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#15. 5 Aspen Way, Pittsfield
- Price: $799,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 170 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 170 days
- View listing on realtor.com
#14. 979 West St, Pittsfield
- Price: $874,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,880
- Price per square foot: $303
- Lot size: 0.9 acres
- Days on market: 75 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,880
- Price per square foot: $303
- Lot size: 0.9 acres
- Days on market: 75 days
- View listing on realtor.com
#13. 1 Pheasant Way, Pittsfield
- Price: $895,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,800
- Price per square foot: $235
- Lot size: 1.0 acres
- Days on market: 138 days (-$30,000 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: $235
- Lot size: 1.0 acres
- Days on market: 138 days (-$30,000 price reduction since listing)
- View listing on realtor.com
#12. 229 High St, Pittsfield
- Price: $989,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,170
- Price per square foot: $160
- Lot size: 1.0 acres
- Days on market: 39 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,170
- Price per square foot: $160
- Lot size: 1.0 acres
- Days on market: 39 days
- View listing on realtor.com
#11. 19 Aspen Way, Pittsfield
- Price: $989,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 4,024
- Price per square foot: $245
- Days on market: 37 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 4,024
- Price per square foot: $245
- Days on market: 37 days
- 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: 20 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: 20 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: 94 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: 94 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: 725 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: 725 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: 32 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: 32 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: 30 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: 30 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: 72 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: 72 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: 37 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: 37 days
- View listing on realtor.com
#3. 593 Lakeway Dr, Pittsfield
- Price: $1,800,000
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,043
- Price per square foot: $591
- Lot size: 0.8 acres
- Days on market: 20 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,043
- Price per square foot: $591
- Lot size: 0.8 acres
- Days on market: 20 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: 18 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: 18 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: 32 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: 32 days
- View listing on realtor.com
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