Tuition and Financial Aid

Winsor’s tuition for the 2025–26 school year is $65,599.

Winsor’s commitment to maintaining its community of students from diverse backgrounds, experiences, and viewpoints is central to the mission of our need-based financial aid program, which ensures equitable access to Winsor’s academic and co-curricular program regardless of a family’s financial circumstance. Winsor’s $6-million financial aid budget supports 24% of the student body by providing financial aid grants that range from $1,000 to the full cost of tuition. These grants meet 100% of those families’ demonstrated need related to their student’s education at Winsor.

The Winsor School offers a variety of named scholarships to students applying for admission. All scholarships require the family to have demonstrated financial need (as determined by completing the Clarity financial aid application); Winsor does not award merit scholarships. 

The LEAD Scholarship for Boston Residents

Awarded to new students entering grades 5 or 6, the LEAD Scholarship is a comprehensive 7 or 8-year scholarship covering all the costs of attendance at Winsor. Eligible students must live in the City of Boston and demonstrate significant leadership potential. To be considered, applicants must complete all the steps of the LEAD Application for Admission in Ravenna and submit the Clarity financial aid application by January 15, 2026.

Hynes-Condon Family Scholarship 

Awarded annually to new students entering Winsor in grades 5, 6, 7, and 9, the Hynes-Condon Family Scholarship was conceived to help students from middle-income families access a Winsor education. The Hynes-Condon Family Scholarship will cover 20-80% of tuition costs for every year of a student’s Winsor journey until graduation. 

Applicants for the scholarship can self-identify or be referred by a member of the extended Winsor community. 

To be eligible for the Hynes-Condon Family Scholarship, students must meet one of the following criteria:

• Would be the first person in their immediate family to attend an independent school
• Has a parent who works in public service (i.e. civil service, non-profit organization, education, public health)
• Has a parent who works in the skilled trades (i.e. plumbing, electrical, carpentry, HVAC) 

All applicants for the scholarship must submit the regular Winsor admission application, the Hynes-Condon Family Scholarship Eligibility Form, and the Clarity financial aid application by January 15, 2026.

Additional Named Scholarships

All applicants for Fall 2026 entry who complete the admission application and Clarity financial application will be automatically considered for other named comprehensive and partial scholarship opportunities. No additional forms or steps are required for the other named scholarships. 

We know that affordability is a big consideration in a school search process. Winsor’s unique Tuition SneakPeek Program (TSP) supports families by offering transparency about cost early on in the admission process.

From September 8 to December 1, 2025, families may opt into our Tuition SneakPeek Program (TSP) to gauge their eligibility for need-based financial aid. The TSP gives families the opportunity to request a sneak peek of their financial aid award and remaining tuition obligation should their student be admitted to Winsor. Participating in the TSP does not have any impact on a student’s likelihood of admission.

1. Complete the Clarity financial aid application, add The Winsor School to the recipient list, and pay the $60 application fee (Clarity automatically applies fee waivers for families below a certain income and asset threshold). You will know you have successfully submitted your application if you see confetti!
2. Upload your most recent pay stub into Clarity.
3. Register for the Tuition SneakPeek Program by filling out this Google form no later than December 1, 2025.
4. Wait 10–14 days for your Clarity application to process.
5. A Winsor staff member will reach out via email to schedule a short 10–15 minute TSP phone call. Calls are only offered from September 10 to December 15.
6. During this short conversation, we will ask additional questions about your application, answer your questions about our need-based financial aid process, and provide a financial aid award estimate. Our goal is to give you an early and accurate estimate to help you determine the financial feasibility of a Winsor education.

Winsor’s financial aid application season runs from September 8, 2025 to January 15, 2026.

Step 1: Complete the 2026–27 Clarity Financial Aid Application by January 15, 2026
After September 8, create an account or log in to an existing one in Clarity Tuition and complete an application for the 2026–27 academic year. List Winsor as a recipient of your application. The application should take no more than 30 minutes to complete.

Only one application per household is required, regardless of the number of applicant children or the number of schools you are applying to.

Have your most recent tax returns available to make entering your income information more efficient and accurate.

Step 2: Upload your most recent pay stub
This is the only document that Winsor requires you to manually upload to your Clarity application. If you are self-employed, omit this step.

Step 3: Submit the Clarity application fee if prompted
Submit the $60 Clarity application fee if prompted to do so. Clarity uses your income and asset information within your application to assess your family’s financial situation and automatically applies a waiver if your family qualifies for one. Qualifying families will bypass all payment screens when their Clarity application form is complete.

You will know you successfully submitted your application if you see confetti on your Clarity screen!

Additional Information:

• Your financial aid application will not be considered complete until all parts have been submitted. When completing your application, you will be asked to electronically sign and submit the IRS Form 4056-C, which gives Clarity permission to pull your prior year tax returns. This means you will not need to manually upload any tax documents yourself.
• In order to adhere to best practices and allow us to offer a comprehensive review of all submissions for financial aid, Winsor requires applicants to submit financial information from all living parents. Divorced or separated families should each complete a separate Clarity financial aid application. No information will be shared between parties. Single parents need to provide proof of single-parent status. A copy of a birth certificate or a letter from an attorney, clergy person or school counselor with an understanding of your situation should be emailed to admission@winsor.edu.

Clarity Assistance
If you need support while completing your application, there is in-app support available through the “Get Help” button in the bottom left of the Clarity screen. If you have any trouble navigating the Clarity website or if you have further questions, please contact Clarity customer service at 800-344-8328 or email support@claritytuition.com for the most prompt response. Alternatively, please email admission@winsor.edu.