Empowering bright children who think and learn differently is a daunting but rewarding journey. It takes the resources of our entire community to guide these students to achieve academic and personal success. Join us in helping every child at Oakland unlock his or her potential with a financial or in-kind donation.

Oakland School students strike a pose.

Financial sustainability is an important issue for all independent and private schools today. Tuition income does not fully cover the total cost of our unique learning environment and proven teaching methods.

To bridge the gap, Oakland School relies on the voluntary financial support of its parent and grandparent body, alumni parents and grandparents, friends of the school, and community members. Voluntary charitable contributions help fuel Oakland’s tuition assistance, staff development, and annual operations to create an extraordinary academic experience.

Without these donations, Oakland would need to dramatically boost its annual tuition cost, thus placing a quality Oakland education beyond the reach of many prospective and current families. Your financial support of the school is crucial to the success of the school.

Donate Through Amazon

Each month, Oakland teachers make requests for supplies, resources, and student rewards. Please consider purchasing an item (or two!) off our Amazon wishlist.

A portion of your everyday purchases on AmazonSmile can benefit Oakland School! Using the button below, you can select Oakland as your charity of choice.

The Annual Fund

The Oakland Annual Fund provides tuition assistance to families who may not be able to fully afford an Oakland education. Families may apply for assistance upon acceptance. Approximately 20 percent of year-round Oakland students benefit from this important fund. While the bulk of annual funds support tuition assistance, a small percentage also augments the general fund which provides for a variety of student, program, and staffing needs. Giving levels that provide donor recognition are as follows:

  • Founder’s Circle: $5,000 and above

  • Brightleaf Society: $2,500-$4,999

  • Director’s Circle: $1,000-$2,499

  • Oakland Stalwarts: $500-$999

  • Oak Tree Club: $100-$499

  • Acorn Club: $1-$99

  • Oakland 1950 Club: For Alumni, $19.50 and above

All contributions to the school qualify as charitable contributions which are fully deductible consistent with federal and state laws. Online donation system by Smart Tuition.

The students in riding gear smile beside one of Oakland's kind horses.

Appreciated Assets

Please contact our Finance Director, Karin Holtz, if you have any questions about what might be the best manner to dispose of any appreciated assets, the value of which can be directed to the school as a charitable contribution. These assets include cash, stock, personal property, real estate, and planned gifts.


To make a cash contribution to Oakland, you may send a personal or business check to the Oakland School, 128 Oakland Farm Way, Troy, VA 22974, or you may use Smart Tuition to securely pay online with your credit card.

real estate

Real estate may be donated to the school, both as an outright gift or through a charitable trust (see below) as a planned gift. Various giving options exist for real estate that do not apply to paper assets. Some of these options permit the owner to continue to live in and use the property for a certain number of years or for the donor’s lifetime, while taking advantage of the tax advantages during their lifetime. Other arrangements offer special tax advantages and a lifetime income opportunity based on the appreciated value of the property. Gifts of real estate, such as undeveloped land, a residence, a vacation home, a farm or a commercial property, should be arranged through the donor and the School. Oakland requires the donor to obtain a written appraisal to determine the fair market value, prior to the transfer of the property to the school.

Planned gifts

There are numerous ways that one can make a planned gift to Oakland School. The easiest is by including the school as a bequest in your will, therein indicating a level of assets that you would like to see the school receive from your estate as a measure of your appreciation for the school’s contribution to the educational and personal growth of your child, of your grandchild or of yourself. The more involved planned gifts center on the creation of a trust that positions your assets to look after the best interests of your beneficiaries while it also makes a valuable contribution to the welfare of Oakland School.

Stocks and bonds

Stock market conditions may preclude the number of stocks in your portfolio that qualify for significant capital gains. However, as asset classes are reorganized and investment vehicles are switched to take advantage of market conditions, there may be stocks and bonds you are holding whose value to your bottom line is greater in being contributed than in being sold and utilized in your portfolio. Should you wish to consider donating any stock or bonds to the school, please contact us first so we are alerted to the impending transfer of assets and can pass along the appropriate bank transfer information to you in advance.

Personal Property and Gifts-in-Kind

Contributions of personal property, including works of art, manuscripts, rare books, antique furnishings, and automobiles, help underwrite both excellence in teaching at Oakland and tuition assistance for eligible students. Items with valuations under $1,000 may be used at the discretion of the school in the annual auction. Any non-automotive gifts with an estimated value of $5,000 or more must have an appraisal documented in writing by an outside expert. Donated automobiles must be deemed safe, drivable, and have passed VA state inspection before they will be accepted by the school.

Contributing personal property to Oakland School has three main benefits. (1) You may receive a charitable deduction for the appraised value at the time of the donation. (2) The value of your charitable contribution will be larger than if you sold the personal property, paid capital gains taxes on any appreciated value and then contributed the cash value to the school. (3) The value of the personal property is removed from your estate, which lowers your estate taxes. For any gifts valued at more than $500, the donor will need to fill out IRS Form 8283, “Non-Cash Contributions.”