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.

#30. 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: 97 days
- View listing on realtor.com

#29. 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: 6 days
- View listing on realtor.com

#28. 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: 82 days (-$30,500 price reduction since listing)
- View listing on realtor.com

#27. 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: 30 days
- View listing on realtor.com

#26. 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: 168 days (-$15,000 price reduction since listing)
- View listing on realtor.com

#25. 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: 118 days (-$67,000 price reduction since listing)
- View listing on realtor.com

#24. 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: 4 days
- View listing on realtor.com

#23. 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: 16 days
- View listing on realtor.com

#22. 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: 345 days (-$20,000 price reduction since listing)
- View listing on realtor.com

#21. 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: 79 days (-$24,000 price reduction since listing)
- View listing on realtor.com

#20. 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: 99 days (-$35,000 price reduction since listing)
- View listing on realtor.com

#19. 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: 122 days (-$46,000 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: 233 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: 231 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: 233 days
- View listing on realtor.com

#15. 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: 231 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: 16 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: 100 days (-$24,000 price reduction since listing)
- View listing on realtor.com

#12. 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: 83 days (-$105,000 price reduction since listing)
- 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: 2 days
- View listing on realtor.com

#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: 157 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: 788 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: 16 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: 95 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: 93 days
- View listing on realtor.com

#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: 135 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: 16 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: 11 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: 81 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: 95 days
- View listing on realtor.com

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