Another healthy year in Hillsborough's high-end, despite market volatility in other price sectors. Seven of the top fifteen sales featured representation of buyer or seller by Cashin Company, In addition, there was a good handful of non-MLS high-end Hillsborough sales this year that do not appear on this list.
| Address | List Price | Sale Price | Sq. Ft. | Lot | DOM | List Date |
| 3250 RALSTON AV | $10,900,000 | $11,000,000 | 9,660 | 80,600 | 2 | 1/28/2008 |
| 125 ROBIN RD | $10,990,000 | $10,900,000 | 10,340 | 120,196 | 14 | 2/22/2008 |
| 660 W SANTA INEZ AV | $8,995,000 | $8,258,333 | 8,445 | 41,184 | 157 | 2/22/2008 |
| 25 ASTER AV | $6,995,000 | $6,500,000 | 7,491 | 26,967 | 52 | 4/11/2008 |
| 440 PULLMAN RD | $6,800,000 | $5,990,000 | 11,040 | 114,954 | 20 | 4/10/2008 |
| 2510 SKYFARM DR | $5,500,000 | $5,500,000 | 6,700 | 1.52 ac | 3 | 2/15/2008 |
| 809 IRWIN DR | $4,995,000 | $4,785,000 | 4,450 | 39,204 | 19 | 1/4/2008 |
| 50 BAYWOOD AV | $4,950,000 | $4,700,000 | 4,360 | 60,418 | 168 | 9/10/2007 |
| 605 BREWER DR | $4,990,000 | $4,450,000 | 6,570 | 39,204 | 84 | 12/10/2007 |
| 194 BRIDGE RD | $4,599,000 | $4,325,000 | 6,150 | 27,000 | 35 | 2/11/2008 |
| 20 LONGVIEW CT | $4,529,000 | $4,300,000 | 4,110 | 35,449 | 3 | 7/18/2008 |
| 745 BROMFIELD RD | $3,395,000 | $4,005,000 | 4,180 | 40946 | 9 | 2/4/2008 |
| 2125 GERI LN | $4,495,000 | $4,000,000 | 3,830 | 17780 | 99 | 5/9/2008 |
| 125 ROBLAR AV | $3,999,000 | $3,949,000 | 4,516 | 16,095 | 10 | 3/31/2008 |
| 45 GLENBROOK DR | $3,950,000 | $3,900,000 | 5,640 | 50,948 | 58 | 2/2/2008 |