Middlesex is a thriving and dynamic school because of the talented teachers and students involved in carrying out its mission—and because of the generous people who support them and provide the foundation for this important work to happen.

A Case for Endowment

A capital gift toward endowment is a gift that helps secure the future of the School by facilitating significant projects that cannot be covered by the Annual Fund.

A gift toward our endowment allows us to provide faculty and students with a learning and living environment that is equivalent to the excellence of their work here, to assure that the generations to come will have the opportunity to find their  promise.

In 1996, Middlesex established The Frederick & Mary Winsor Society to honor those alumni, parents, and friends of the School who have included Middlesex in their estate plans or who have established life income gifts like those described here. Middlesex’s founder Frederick Winsor and his wife Mary devoted their lives to building and strengthening the young school. 

After her husband’s death, Mary continued to support the School financially and, in fact, provided generously for Middlesex in her own estate plans. Today several endowed funds, which support scholarship, faculty salaries, and general needs, are the direct result of Mary’s plans.


A bequest from either a will or living trust is one of the most popular and easiest ways to support Middlesex in the future. A bequest enables you to gift any amount you wish to Middlesex, free of estate tax. 

You can give cash, property, or a percentage of your estate, with or without restrictions. A bequest to Middlesex can be made by creating a new will, adding a codicil to your present will, or including Middlesex in your revocable trust.

Retirement plans
(ira /401k)

Retirement funds can be costly to inherit, as these assets often face double taxation. Because assets remaining in retirement plans are often funded with pre-tax dollars, they are considered “income in respect of a decedent.” As a result, not only is the amount diminished by estate taxes, but the recipient must also pay income taxes on the assets once they receive them.

Through estate planning, however, you can take advantage of the charitable gift option.

Through a financial advisor, estate planner, or plan administrator, you can designate Middlesex as the beneficiary of your retirement plan, avoiding all income and estate taxes while supporting an area of the School that is important to you.

Life Insurance

If you make Middlesex the owner and beneficiary of your policy, you will typically receive an income tax deduction for the policy’s fair market value or cost basis. In addition, you will receive an estate tax deduction for the insurance proceeds.

Another option is to use life insurance to replace the value of a different gift. For example, you could donate appreciated securities to Middlesex—taking advantage of the tax benefits that go along with such a gift— and purchase life insurance to “replace” the assets. This can allow you to bequeath an equivalent amount to your heirs, as if you had left them the stock.

Real Estate

Real estate, whether a primary residence or a vacation or business/commercial property, can often be an optimal charitable gift. Donating real estate that has been held for over a year generally entitles the donor to an income tax deduction equal to the full fair market value of the contributed property. 

The donor can also avoid capital gains taxes on the appreciated portion of the property that would have been taxed if it were sold.