In most national real estate publications, you will read that people buy in the spring and move in the summer. This is largely tied to the school calendar, and buyers want their children to get settled before the new school year starts. If you back that up, the best time to list a property would therefore be late March or April. That also coincides, in the Northeast, with better weather for open houses and showings in April and May.
There are some deviations from that, even in our area. For example, Branford has a big supply of condos, and only 1 in 30 units sends a child to the public schools. Thanks in large part to the big proportion of condos, there is a relatively smaller pool of single-family homes, and so a lower percentage of spring sales and summer closings. Since condos are often investment properties, and since investments are influenced heavily by tax considerations, we see a jump in condo closings in the last quarter of the year, in part for tax reasons, and partially just because there isn't a school-based reason to prefer summer.
Yale is, of course, the region's biggest employer. Therefore, the Yale calendar is very important in the decision of when to buy and sell, especially in New Haven and closely contiguous towns. While offers are made to new employees year-round, and while promotions and local hires can occur at any time, we see a big uptick after the first of the year, especially with the Medical School and Hospital, where July 1st is a traditional starting date. This moves the optimal time to list up into late January or February, even though there can be weather issues in those months.
If you are a local buyer, therefore, you should consider buying before you have to compete with Yale buyers on short time frames. In case you haven't done the math on that, you need to be buying now!