Any realtor that has been in the business for more than 5 minutes has been asked that question. I think it is the most frequently asked real estate question after "how's the market?"

Frankly, I hate answers that are convoluted. However, in this case there is no right or wrong answer. If you think about the answer from a seasonal point-of-view, most realtors will tell you that the Spring market generally produces the most buying activity. (Even though, the transactions may not occur until the Summer). This is often generated by families looking to keep their children uninterrupted by a move until the school year has finished. Although many new listings come into the marketplace at that time, prospective sellers should understand that the downfall to this timing is the extensive competition they will have to contend with.
In my market of Fairfield County CT, specifically Norwalk, the last two Winter markets turned out to be excellent for home sellers. The reason: exactly the opposite of the Spring market--there just wasn't much inventory to compete with. As a result, homes that were on market sold quickly, often with multiple offers and at excellent prices. In some cases, better sale prices than what we were seeing in the Spring. However, it should be noted that Winter can be a bit more difficult on the seller in harsh climates. Contending with snow and ice are just a couple of the additional inconveniences in having their home on the market.
Summer is a traditionally slower time with activity as buyers prioritize vacations and getting ready for back-to-school. However, I feel the Summer is a great time to list a house that needs the help of mother nature. Whether that is showing off beautiful landscaping, ensuring lush trees fill-in for privacy from close by neighbors, highlighting a wonderful in-ground pool or patio, boasting central air conditioning or other aspects that can only be appreciated in those precious months.
Finally there is the Fall market. The Fall market in Fairfield County Connecticut is lovely. Colorful landscaping shows beautifully and temperatures are more mild. Buyer activity picks up as their motivation is to secure a new home before the end of the year (for tax purposes) as well as be settled in before the start of nasty winter weather.
Of course not just seasons effect the "best time" to sell a home. Current interest rates, projected interest rate changes, the stock market, local economies and jobs and world news and events also play a significant role.
Lastly, there should also be considered whether a house will be vacant or occupied when it goes to market. In the northeast, Winter is a tough time for sellers who leave a home vacant. Monthly carrying costs are higher not just from the heating cost (as it is important to present a warm and cozy feeling even if it is vacant), but the home owner still needs to be diligent in keeping the house safe from snow and ice for visitors. This often requires hiring outside companies to get to the home promptly after every snowfall.
In conclusion, trying to pin-point the perfect time to sell a home is much like trying to the time the stock market. Instead, sellers should evaluate the pros and cons of their specific situationand get the advice and guidance of a realtor
Personally, I think the best answer to the question "When is the best time to sell?" is: "when you are ready and motivated to get the home sold!"

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