The Winsor School Assets Climbed 9.2% to $256.7 Million, Operating Revenues Outpaced Expenses and More Than Doubling Prior Year's Surplus
By Data Team | Published October 29, 2026
The Winsor School's total assets climbed 9.2% to $256.7 million in fiscal year 2025, anchored by a $143.6 million endowment whose $4.41 million annual draw funds 10.5% of the Boston day school's $41.94 million gross operating budget (and 12.5% of its $35.35 million net GAAP expense budget), according to its latest IRS Form 990 filing. That capital base enables Winsor to spend $65,595 per student on direct program services ($87,731 per student in total institutional expenditures) while awarding $5.63 million in need-based financial aid.
Winsor's financial profile demonstrates how an urban grades 5–12 day school deploys endowment returns and annual philanthropy to exceed tuition-driven constraints. While gross tuition and fees average $63,486 across its 478 students ($51,702 net of financial aid), the school's $300,364 endowment per student and $10.08 million in annual contributions subsidize every student by $2,109 in direct program services and $24,245 in total institutional operations—supporting the small-cohort STEM instruction, Independent Learning Experiences (ILE), and need-based access behind Winsor's #3 standing in the Boston Private High School Elite College Placement Index (ECPI).
Combining disciplined operating surpluses ($1.51 million in FY25) with $16.22 million in unrealized investment gains expanded Winsor's net assets by 9.4% to $206.03 million. That balance-sheet expansion insulates instructional budgets and financial aid grants supporting 25.1% of the student body against broader economic fluctuations.
Institutional & Governance Profile
Located at 103 Pilgrim Road in Boston's Longwood Medical and Academic Area, The Winsor School operates as a 501(c)(3) college-preparatory day school educating girls in grades 5 through 12. Its governance structure pairs a 27-member Board of Trustees with a senior administrative team overseeing $256.7 million in institutional assets.
Institutional Scale and Board Structure
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Founding & Workforce Scale: Established in 1886 and legally incorporated in Massachusetts in 1908 (EIN 04-2105842), Winsor issued 245 Form W-2s in calendar year 2024, filed 87 Forms 1096 for independent vendors, and engaged 100 active volunteers.
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Executive Leadership: Head of School Sarah Pelmas leads the administration alongside Chief Operating Officer Karen Geromini, Associate Head of School Kate M. Caspar, Head of Lower School Sharon Jones Phinney, and Senior Controller Elizabeth McNeil.
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Governing Board (Part VI & VII): The corporation is governed by 27 voting trustees, 25 of whom are independent. Board officers include President Allison Kaneb Pellegrino, Vice President Larry Cheng, Treasurer Lori Whelan, Assistant Treasurer David E. Goel, and Clerk Elizabeth Bennett Carroll.
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Fiduciary & Conflict Oversight (Schedule O): All trustees submit annual conflict-of-interest certifications reviewed by the Clerk and Board officers, and the full return is posted to a secure trustees-only portal prior to IRS filing (prepared with CBIZ Advisors LLC).
Top-Line Financials
During fiscal year 2025 (July 1, 2024 through June 30, 2025), Winsor expanded its total assets by $21.64 million (+9.2%) to $256.71 million while growing total net assets by $17.73 million (+9.4%) to $206.03 million. Operating revenues outpaced functional expenses by $1.51 million, more than doubling the prior year's operating surplus.
Balance Sheet Strength
- Total Assets $256,707,059 (+9.2%)
- Total Liabilities $50,679,775 (+8.4%)
- Total Net Assets $206,027,284 (+9.4%)
- Donor-Restricted Net Assets $108,781,301 (52.8% of Total Net Assets)
- Unrestricted Net Assets $97,245,983 (47.2% of Total Net Assets)
Operating Performance
- Total Revenue $43,443,149 (+5.5%)
- Total Expenses $41,935,264 (+3.6%)
- Operating Surplus $1,507,885 (+112.9%)
- Unrealized Gains (Excluded) $16,218,918
Note: The $1.51 million operating surplus reflects Form 990 revenue less expenses; combining this surplus with $16.22 million in net unrealized investment gains (Part XI, Line 5) accounts for the full $17.73 million increase in Winsor's net assets.
Revenue Breakdown
While tuition and fees provide 69.9% of Winsor's $43.44 million in total Form 990 revenue, philanthropic gifts and realized investment income supply the remaining 30.1% ($13.10 million). Contributions exceeded $10.0 million for the fourth consecutive year, while realized investment income jumped 61.7% year-over-year.
Primary Revenue Streams
FY25 Revenue Distribution
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Program Service Revenue Up 4.8% YoY$30,346,420 (69.9%)
- Gross Tuition & Fees (478 Students) $30,346,420
- Net Tuition After Financial Aid ($5.63M) $24,713,525
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Contributions & Grants Down 0.6% YoY$10,078,163 (23.2%)
- Endowment Contributions (Schedule D) $8,883,662
- Annual Fund & Operating Gifts $1,194,501
- Noncash Public Stock Gifts (33 Donations) $548,145
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Investment Income Up 61.7% YoY$2,253,555 (5.2%)
- Dividends & Interest (Net of -$118K UBI Loss) $1,237,310
- Net Realized Gains on Asset Sales $1,016,245
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Other Revenue Up 11.0% YoY$765,011 (1.8%)
- Net Facility Rental Income ($637,036 Gross) $636,437
- Miscellaneous Program Revenue $128,574
Endowment Performance and Asset Allocation
Winsor manages $155.18 million in total investment holdings on its balance sheet, encompassing its $143.57 million endowment ($300,364 per student) alongside working capital reserves. Rather than relying solely on public index funds, Winsor allocates 78.7% ($122.06 million) of its investment portfolio to Limited Liability Partnerships and Companies, including $27.39 million deployed through offshore investment vehicles in Central America and the Caribbean.
This alternative-heavy allocation requires Winsor to file federal foreign investment disclosures (Forms 926, 5471, 8621, and 8865) and generated -$83,514 in net unrelated business loss from partnership K-1s on Form 990-T. Because federal law classifies Winsor as a secondary school rather than a college, the institution remains exempt from the IRC Section 4968 endowment excise tax on net investment income.
Portfolio Performance & Asset Allocation ($155.2M Total Holdings)
Part X & Schedule D/F Allocation
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Endowment Balance (EOY): $143,574,185 (up 9.4% YoY), representing $300,364 per student across 478 students in Grades 5–12.
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Endowment Return & Total Portfolio Gains: $7,895,443 in net endowment investment earnings (Schedule D, Part V), while total balance-sheet investments generated $18,472,473 in combined realized/unrealized gains and income ($2.25M realized income/gains plus $16.22M unrealized gains).
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Alternative & Offshore Capital: 78.7% ($122.06M) of the $155.18M investment portfolio sits in Limited Liability Partnerships and Companies, including $27.39M in Central American and Caribbean offshore fund structures, managed for $950,441 in external investment management fees (61 bps).
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Annual Endowment Payout: $4,412,004 distributed for facilities, scholarships, and academic programs—covering 10.5% of Winsor's $41.94M gross Form 990 operating budget (12.5% of its $35.35M net GAAP budget).
Detailed Asset Mix
5-Year Endowment History
Schedule D, Part V tracks the 74.9% growth of Winsor's endowment over five fiscal years. Starting at $82.09 million at the beginning of FY21, the endowment absorbed $34.00 million in direct donor gifts and $45.35 million in net investment gains while distributing $17.86 million to annual school operations. By the close of FY25, the fund reached $143.57 million, split between 72.578% permanent donor-restricted endowment and 27.422% board-designated quasi-endowment.
FY25 Endowment Waterfall (Schedule D, Part V)
Visualizing the bridge from Beginning of Year (1a) to End of Year (1g) in millions.
5-Year Historical Endowment Balances (Line 1g)
End of year balance progression in millions (FY21 - FY25).
| IRS Line Item | FY25 (Current) | FY24 (Prior) | FY23 (2 Yrs Back) | FY22 (3 Yrs Back) | FY21 (4 Yrs Back) |
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| 1a. Beginning of year | $131,207,084 | $112,502,938 | $100,892,893 | $111,189,502 | $82,085,921 |
| 1b. Contributions | $8,883,662 | $6,685,937 | $4,595,017 | $4,064,608 | $9,768,946 |
| 1c. Net investment earnings | $7,895,443 | $15,953,213 | $10,620,028 | ($11,281,703) | $22,158,819 |
| 1d. Grants or scholarships | $0 | $0 | $0 | $0 | $0 |
| 1e. Other expenditures | ($4,412,004) | ($3,935,004) | ($3,605,000) | ($3,079,514) | ($2,824,184) |
| 1f. Administrative expenses | $0 | $0 | $0 | $0 | $0 |
| 1g. End of year balance | $143,574,185 | $131,207,084 | $112,502,938 | $100,892,893 | $111,189,502 |
Per-Student Spending and True Cost
Evaluating Winsor's Form 990 functional expenses against its 478-student enrollment shows that direct program service expenditures ($31,354,314) average $65,595 per student—surpassing the $63,486 per student generated in gross tuition and fees ($51,702 net of financial aid). Even full-pay families receive a direct programmatic subsidy of $2,109 per student before accounting for administrative and institutional overhead.
When factoring in $7.58 million in management and general expenses and $3.00 million in advancement operations, Winsor's overall total spend reaches $41,935,264, or $87,731 per student ($24,245 per student above gross tuition). That expenditure funds a 7:1 student-to-faculty ratio across eight academic departments, 13 AP courses (including four in science, four in world languages, and post-calculus mathematics), over 50 student clubs, 14 interscholastic sports with over 80% student participation, and senior Independent Learning Experiences (ILE).
Operations vs. Revenue
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Direct Program Service Spend (Primary Per-Student Metric): $31,354,314 across 478 students in Grades 5–12 ($65,595 gross program spend per student; $53,810 net regular-session instructional spend excluding $5.63M in financial aid grants).
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Overall Total Institutional Spend: $41,935,264 ($87,731 total spend per student), including $7,581,879 (18.1%) in Management & General overhead and $2,999,071 (7.2%) in Fundraising expenses.
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Tuition & Fee Revenue: $30,346,420 gross ($63,486 per student before financial aid; $51,702 net per student). Endowment payouts ($4.41M) and annual philanthropy cover the $2,109 per-student direct program gap ($24,245 per-student total spend gap).
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Instructional & Co-Curricular Infrastructure: Supports 268 Upper School and 210 Lower School students taking 5–6 courses per semester, plus $974,762 in campus food services, $860,921 in instructional supplies, and $458,405 in information technology.
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Campus Rental & Auxiliary Offset: Winsor generated $636,437 in net real estate rental income and $128,574 in auxiliary program fees to help offset campus operating costs.
Financial Aid: How Winsor Spends $5.63M on Access
In FY25, Winsor disbursed $5,632,895 in need-based financial aid grants (up 3.2% from $5,458,563 in FY24) to 120 domestic students, supporting 25.1% of the 478-student body. Grants range from 5% to 100% of tuition and average $46,941 per aided student—covering 73.9% of average gross tuition and fees.
All financial aid is awarded strictly on demonstrated family need through the Financial Aid Office and credited directly to student tuition accounts (Schedule I, Part IV). That commitment to socioeconomic access underpins an Upper School community in which 53% of students identify as multiracial or students of color, while over $2.2 million of Winsor's aid budget directly supports families residing within the City of Boston.
Internal Student Support (Schedule I)
- Aided Student Share 25.1% (120 students)
- Need-Based Tuition Grants $5,632,895
- Average Grant per Aided Student $46,941
- Grant Coverage Range 5% to 100% of Tuition
- Schedule L Interested-Person Aid $36,499 (1 recipient)
Boston Access & Community Partnerships
- City of Boston Resident Scholarships ($2.22M+) Need-based tuition grants dedicated to families residing in Boston neighborhoods, reported as Winsor's primary municipal community benefit.
- Local Public School & Youth Outreach Ongoing tutoring and facility partnerships with the Sarah Greenwood K–8 School, Big Sisters of Boston, Ellis Memorial, Boston ABCD, and the Ucal McKenzie Breakaway Foundation soccer camp.
Executive and Administrative Compensation
Unlike billion-dollar boarding schools that employ in-house chief investment officers, Winsor outsources portfolio management ($950,441 in external investment fees) and concentrates its executive payroll on academic and operational leadership. Head of School Sarah Pelmas is the school's highest-compensated employee at $746,815 in total FY25 compensation, followed by Chief Operating Officer Karen Geromini ($355,713) and Associate Head of School Kate M. Caspar ($271,067).
Total employee compensation across Winsor's 245 W-2 staff members rose 7.6% year-over-year to $20.17 million, accounting for 48.1% of all institutional expenditures. Sixty-nine employees (28.2% of the workforce) received more than $100,000 in reportable compensation during calendar year 2024, reflecting competitive salary benchmarks in the Greater Boston independent school market.
Payroll Scale and Compensation Governance
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Total Institutional Payroll: Winsor paid $20,170,683 in total salaries, retirement contributions, and employee benefits in FY25 (48.1% of total expenses) across 245 W-2 employees, with 69 staff members earning over $100,000.
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Top Executive Packages: Head of School Sarah Pelmas received $746,815 in total compensation (including $614,140 base salary and $40,000 in non-taxable Section 457(f) deferred compensation), while COO Karen Geromini earned $355,713 and Associate Head Kate M. Caspar earned $271,067.
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Board Compensation Governance (Schedule J & Schedule O): The full Board of Trustees sets and votes on the Head of School's compensation using an independent compensation consultant, peer Form 990s, compensation surveys, and a written employment contract. The Board's Finance Committee reviews comparability data for other officers and key employees before submitting recommendations for full Board approval.
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Form 990, Schedule J, Part II: Compensation Breakdown (FY25)
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| Name & Title (A) | Base Comp (B-i) | Bonus (B-ii) | Other (B-iii) | Retirement & Deferred (C) | Nontaxable Benefits (D) | Total (E) | Prior Deferred (F) |
| Sarah PelmasHead of School | $614,140 | $0 | $13,812 | $74,500 | $44,363 | $746,815 | $0 |
| Karen GerominiChief Operating Officer | $310,194 | $0 | $1,032 | $30,172 | $14,315 | $355,713 | $0 |
| Kate M. CasparAssociate Head of School | $250,818 | $0 | $520 | $18,353 | $1,376 | $271,067 | $0 |
| Erika McMahonDir. of Advancement, Campaign Dir. | $197,236 | $0 | $183 | $10,579 | $30,253 | $238,251 | $0 |
| John CromptonDir. of Facilities & Construction | $195,100 | $0 | $2,199 | $19,668 | $19,466 | $236,433 | $0 |
| Martha BrowningDirector of Strategic Communications | $191,671 | $0 | $266 | $14,809 | $13,796 | $220,542 | $0 |
| Marcus YoungDirector of Technology | $175,018 | $0 | $240 | $13,965 | $29,100 | $218,323 | $0 |
| Sharon Jones PhinneyHead of Lower School | $191,241 | $0 | $1,057 | $18,580 | $1,060 | $211,938 | $0 |
Facilities, Debt, and Municipal Relations
Winsor's urban campus in Boston's Longwood neighborhood carries a gross book value of $143.55 million ($93.41 million net of accumulated depreciation), anchored by the Lubin-O'Donnell Center for Performing Arts and Wellness and modern STEM laboratories. To preserve endowment liquidity while modernizing its facilities, Winsor refinanced its capital debt through the Massachusetts Development Finance Agency in December 2021.
In its municipal relationship with the City of Boston, Winsor reports $0 in direct cash grants to domestic governments on Form 990 Schedule I, Part II. Instead, the school participates in the City of Boston's Payment in Lieu of Taxes (PILOT) framework via documented Community Benefits credits—leveraging over $2.2 million in financial aid for Boston resident students and local public school partnerships—and entered into a new written PILOT agreement with the City of Boston in FY26.
Capital Debt & Municipal Engagement
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Physical Plant & Campus Operations: Winsor holds $143,554,343 in gross land, buildings, and equipment ($93,411,665 net book value after $50.14M in accumulated depreciation), recording $4,441,238 in annual depreciation, $1,647,948 in occupancy expenses, and $778,219 in equipment maintenance.
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Tax-Exempt Bond Refinancing (Schedule K): Winsor carries $38,055,874 in tax-exempt bond liabilities (down from $38.29M in FY24). Issued on December 13, 2021 via the Massachusetts Development Finance Agency ($38,866,134 issue price) to refund its Series 2013A and 2013B revenue bonds, the debt required $898,157 in FY25 loan expenses.
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Schedule I Town-Gown PILOT Payments & Municipal Relations: Winsor recorded $0 on Form 990 Schedule I, Part II for direct municipal cash grants. Under the City of Boston's PILOT program for tax-exempt institutions holding over $15 million in property, Winsor satisfies its municipal participation through Community Benefits credits—led by $2.22M+ in financial aid to Boston residents, facility sharing, and tutoring partnerships with Boston public schools—and formalized a new written PILOT agreement with the City of Boston in FY26.
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Top Independent Contractors (Part VII, Section B): Across 24 independent contractors paid over $100,000, the five largest disbursements went to FLIK Compass Group USA ($787,847 for dining services), McDonald Electrical Corporation ($525,357 for HVAC), Goody Clancy & Associates ($518,893 for architectural/campus consulting), First Student Inc. ($448,343 for bus transportation), and Allied Universal ($433,814 for campus security).
Editorial Note
All financial figures in this report derive from The Winsor School's FY25 IRS Form 990 (covering July 1, 2024 through June 30, 2025 across 478 enrolled students in Grades 5–12) and have been verified by the data team.
While Winsor spends $65,595 per student in direct program services ($87,731 in overall institutional expenditures), Chicardgo School does not imply that financial expenditure mathematically causes higher placement into Ivy+, Top 25 National University, or Top 15 Liberal Arts College tiers. Rather, these financial resources support the faculty, need-based financial aid, and academic curriculum that operate alongside Winsor's historical college matriculation outcomes.
Accounting Reconciliation (Schedule D, Parts XI & XII): Readers comparing Winsor's GAAP audited financial statements to IRS Form 990 will observe differences in reported revenue and expenses. Audited financial statements report $53,079,330 in total revenue and $35,352,527 in total expenses, whereas Form 990 reports $43,443,149 in revenue and $41,935,264 in expenses. Form 990 excludes $16,218,918 in net unrealized investment gains from operating revenue, nets $599 in direct rental expenses against gross rents, and records $5,632,895 in student financial aid grants and $950,441 in investment management fees as gross operating revenues and expenses rather than netting them against tuition and investment returns.
Frequently Asked Questions: The Winsor School's Form 990 Financials
As of Fiscal Year 2025, The Winsor School's endowment stands at $143.57 million ($300,364 per student), up 9.4% year-over-year. Its $4.41 million annual payout funds 10.5% of the school's $41.94 million gross Form 990 operating budget and 12.5% of its $35.35 million net GAAP expense budget.
Winsor spends $65,595 per student annually in direct program services ($31.35 million across 478 students, or $53,810 net of financial aid grants), which exceeds the $63,486 generated per student in gross tuition and fees. When including management and fundraising overhead, total institutional spending reaches $87,731 per student ($41.94 million total expenses).
Winsor awarded $5,632,895 in need-based financial aid grants in FY25 to 120 domestic students, supporting 25.1% of the student body. Grants range from 5% to 100% of tuition and average $46,941 per aided student.
Head of School Sarah Pelmas is the highest-compensated employee, receiving $746,815 in total compensation in FY25 ($614,140 in base compensation, $13,812 in other reportable pay, $74,500 in retirement and Section 457(f) deferred compensation, and $44,363 in nontaxable benefits).
Yes. Because federal law classifies Winsor as a grades 5–12 secondary school rather than an institution of higher education, the school is exempt from the federal IRC Section 4968 excise tax on net investment income.
The Winsor School's total assets reached $256.71 million in fiscal year 2025, anchored by $155.18 million in total investment securities and $93.41 million in net campus land, buildings, and equipment.
Further Reading
High School
July 8, 2026STEM and Urban Need-Blind Access - The Winsor School Claims #3 Position in Boston Private High School Elite College Placement Index
Analysis of The Winsor School's college placement, examining its Harvard and MIT pipelines, need-blind financial aid, the ILE program, and its overall standing as #3 in the Boston Private High School ECPI.
Data Analysis
September 8, 2026Top Private Feeder Schools
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