Most expensive homes for sale in Pittsfield
Written by:
February 18, 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. 15 Winesap Rd, Pittsfield
- Price: $429,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 1,368
- Price per square foot: $313
- Lot size: 0.3 acres
- Days on market: 31 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 1,368
- Price per square foot: $313
- Lot size: 0.3 acres
- Days on market: 31 days
- View listing on realtor.com
#29. 4 Loumar Dr, Pittsfield
- Price: $429,900
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,604
- Price per square foot: $165
- Lot size: 0.5 acres
- Days on market: 141 days (-$5,000 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,604
- Price per square foot: $165
- Lot size: 0.5 acres
- Days on market: 141 days (-$5,000 price reduction since listing)
- View listing on realtor.com
#28. 25 Hubbard Ave, Pittsfield
- Price: $449,000
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,530
- Price per square foot: $177
- Lot size: 0.8 acres
- Days on market: 184 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,530
- Price per square foot: $177
- Lot size: 0.8 acres
- Days on market: 184 days
- View listing on realtor.com
#27. 47 Gale Ave, Pittsfield
- Price: $449,000
- 3 bedrooms, 1 full bathrooms, 1 half bathroom
- Square feet: 1,456
- Price per square foot: $308
- Lot size: 0.3 acres
- Days on market: 163 days
- View listing on realtor.com
- 3 bedrooms, 1 full bathrooms, 1 half bathroom
- Square feet: 1,456
- Price per square foot: $308
- Lot size: 0.3 acres
- Days on market: 163 days
- View listing on realtor.com
#26. 40 Leroi Dr, Pittsfield
- Price: $459,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,013
- Price per square foot: $152
- Lot size: 0.4 acres
- Days on market: 24 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,013
- Price per square foot: $152
- Lot size: 0.4 acres
- Days on market: 24 days
- View listing on realtor.com
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#25. 59 Mountain Dr, Pittsfield
- Price: $464,500
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,262
- Price per square foot: $205
- Lot size: 0.4 acres
- Days on market: 13 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms
- Square feet: 2,262
- Price per square foot: $205
- Lot size: 0.4 acres
- Days on market: 13 days
- View listing on realtor.com
#24. 9 Hawthorne Ave, Pittsfield
- Price: $470,000
- 3 bedrooms, 1 full bathrooms
- Square feet: 1,482
- Price per square foot: $317
- Lot size: 0.2 acres
- Days on market: 163 days (-$70,000 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 1 full bathrooms
- Square feet: 1,482
- Price per square foot: $317
- Lot size: 0.2 acres
- Days on market: 163 days (-$70,000 price reduction since listing)
- View listing on realtor.com
#23. 43 Chapman Rd, Pittsfield
- Price: $499,000
- 2 bedrooms, 2 full bathrooms
- Square feet: 1,521
- Price per square foot: $328
- Lot size: 0.1 acres
- Days on market: 3 days
- View listing on realtor.com
- 2 bedrooms, 2 full bathrooms
- Square feet: 1,521
- Price per square foot: $328
- Lot size: 0.1 acres
- Days on market: 3 days
- View listing on realtor.com
#22. 1136 Barker Rd Unit 25, Pittsfield
- Price: $510,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,044
- Price per square foot: $249
- Days on market: 41 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,044
- Price per square foot: $249
- Days on market: 41 days
- View listing on realtor.com
#21. 139 Ann Dr, Pittsfield
- Price: $548,000
- 6 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 2,927
- Price per square foot: $187
- Lot size: 0.6 acres
- Days on market: 193 days (-$27,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 2,927
- Price per square foot: $187
- Lot size: 0.6 acres
- Days on market: 193 days (-$27,000 price reduction since listing)
- View listing on realtor.com
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#20. 469 Pecks Rd, Pittsfield
- Price: $579,000
- 4 bedrooms, 1 full bathrooms, 1 half bathroom
- Square feet: 1,610
- Price per square foot: $359
- Lot size: 0.5 acres
- Days on market: 3 days
- View listing on realtor.com
- 4 bedrooms, 1 full bathrooms, 1 half bathroom
- Square feet: 1,610
- Price per square foot: $359
- Lot size: 0.5 acres
- Days on market: 3 days
- View listing on realtor.com
#19. 11 Brookside Dr, Pittsfield
- Price: $589,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,448
- Price per square foot: $240
- Lot size: 0.8 acres
- Days on market: 31 days (-$46,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,448
- Price per square foot: $240
- Lot size: 0.8 acres
- Days on market: 31 days (-$46,000 price reduction since listing)
- View listing on realtor.com
#18. 13 Cherry Hill Dr, Pittsfield
- Price: $599,999
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,030
- Price per square foot: $295
- Days on market: 19 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,030
- Price per square foot: $295
- Days on market: 19 days
- View listing on realtor.com
#17. 46 Glory Dr, Pittsfield
- Price: $634,900
- 5 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,572
- Price per square foot: $246
- Lot size: 0.5 acres
- Days on market: 13 days
- View listing on realtor.com
- 5 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,572
- Price per square foot: $246
- Lot size: 0.5 acres
- Days on market: 13 days
- View listing on realtor.com
#16. 32 Brunswick St, Pittsfield
- Price: $649,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,386
- Price per square foot: $272
- Lot size: 0.7 acres
- Days on market: 6 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,386
- Price per square foot: $272
- Lot size: 0.7 acres
- Days on market: 6 days
- View listing on realtor.com
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#15. 1136 Barker Rd Unit 48, Pittsfield
- Price: $660,000
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,826
- Price per square foot: $233
- Days on market: 266 days (-$39,000 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,826
- Price per square foot: $233
- Days on market: 266 days (-$39,000 price reduction since listing)
- View listing on realtor.com
#14. 6 Lori Ct, Pittsfield
- Price: $729,000
- 5 bedrooms, 3 full bathrooms
- Square feet: 4,275
- Price per square foot: $170
- Lot size: 1.1 acres
- Days on market: 117 days (-$11,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms
- Square feet: 4,275
- Price per square foot: $170
- Lot size: 1.1 acres
- Days on market: 117 days (-$11,000 price reduction since listing)
- View listing on realtor.com
#13. 1136 Barker Rd Unit 66, Pittsfield
- Price: $740,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,124
- Price per square foot: $348
- Days on market: 159 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,124
- Price per square foot: $348
- Days on market: 159 days
- View listing on realtor.com
#12. 41 Meadow Ridge Dr, Pittsfield
- Price: $749,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,451
- Price per square foot: $217
- Lot size: 0.5 acres
- Days on market: 52 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,451
- Price per square foot: $217
- Lot size: 0.5 acres
- Days on market: 52 days
- View listing on realtor.com
#11. 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: 149 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: 149 days (-$40,000 price reduction since listing)
- View listing on realtor.com
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#10. 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: 37 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 37 days
- View listing on realtor.com
#9. 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: 35 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 35 days
- View listing on realtor.com
#8. 5 Aspen Way, Pittsfield
- Price: $799,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 37 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 37 days
- View listing on realtor.com
#7. 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: 35 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,000
- Price per square foot: $399
- Days on market: 35 days
- View listing on realtor.com
#6. 20 Spadina Pkwy, Pittsfield
- Price: $849,000
- 5 bedrooms, 4 full bathrooms
- Square feet: 4,170
- Price per square foot: $203
- Lot size: 0.6 acres
- Days on market: 124 days (-$41,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms
- Square feet: 4,170
- Price per square foot: $203
- Lot size: 0.6 acres
- Days on market: 124 days (-$41,000 price reduction since listing)
- View listing on realtor.com
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#5. 1136 Barker Rd Unit 33, Pittsfield
- Price: $879,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,094
- Price per square foot: $214
- Days on market: 57 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,094
- Price per square foot: $214
- Days on market: 57 days
- View listing on realtor.com
#4. 1 Pheasant Way, Pittsfield
- Price: $925,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,800
- Price per square foot: $243
- Lot size: 1.0 acres
- Days on market: 5 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,800
- Price per square foot: $243
- Lot size: 1.0 acres
- Days on market: 5 days
- View listing on realtor.com
#3. 1120 Churchill St, Pittsfield
- Price: $999,900
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,968
- Price per square foot: $251
- Lot size: 1.7 acres
- Days on market: 37 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,968
- Price per square foot: $251
- Lot size: 1.7 acres
- Days on market: 37 days
- View listing on realtor.com
#2. 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: 592 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: 592 days
- View listing on realtor.com
#1. 8 Northbrook Ln, Pittsfield
- Price: $1,500,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,100
- Price per square foot: $483
- Lot size: 2.8 acres
- Days on market: 590 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,100
- Price per square foot: $483
- Lot size: 2.8 acres
- Days on market: 590 days
- View listing on realtor.com
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