Circle Square Foundation
Circle Square Foundation is a private foundation focused on Recreation & Sports, based in Ocala, FL. IRS filing data is available from 2021 through 2025. As of 2025, the organization holds $105.1M in total assets. In 2025, it awarded 2 grants totaling $2.8M. Net investment income was $2.0M.
Circle Square Foundation at a glance
In short: Circle Square Foundation gave $2.8M across 2 grants in 2025 (avg $1.4M), mostly in Florida. Source: 2025 IRS Form 990-PF.
- Annual giving (2025)
- $2,757,405
- +36.9% vs 2024
- Grants made (2025)
- 2
- -60.0% vs 2024
- Average grant
- $1,378,703
- +242.3% vs 2024
- Median grant
- $1,378,703
- Total assets
- $105,112,520
- -3.7% vs 2024
- Primary geography
- Florida (100% of itemized 2025 grant dollars)
- Latest 990 filing
- Form 990-PF, 2025 View filing
Data from IRS Form 990-PF, 2025; updated September 2026.
Who Circle Square Foundation funds
How this funder distributes its grants
Top Recipients
Top 2 recipients in 2025
The largest 2025 recipient was Colen Family Charitable Trust ($2.7M). Together the top 2 received $2.8M.
Grant Size Distribution
12 grants across all recorded years
The most common grant size was under $50K: 8 grants of 12 (67%).
Geographic Focus
Where this funder awards grants
Grant Distribution by State
Share of 2025 grant dollars across all 2 itemized grants.
States
Cities
How Circle Square Foundation gives
- Giving fell 84% from 2022 to 2025. Method
From the foundation's IRS Form 990-PF filings. Methodology.
Giving History
Giving Over Time
Total grant dollars and number of grants per year
From 2022 to 2025, annual grant giving ranged from $2.0M (2024) to $17.2M (2022). In 2025 it made 2 grants totaling $2.8M.
Grants by year
Grant recipients and amounts by year
| Recipient | Purpose | Amount |
|---|---|---|
| Colen Family Charitable Trust Ocala, FL | Charitable Contribution | $2,731,905 |
| Community Foundation for Ocala Ocala, FL | Charitable Contribution | $25,500 |
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Financial History
Multi-year comparison from IRS filings
| Filing year | Total Assets | Revenue | Expenses | Grants paid | Grants | Qualifying Distributions | Net Investment Income |
|---|---|---|---|---|---|---|---|
| 2025 | $105,112,520 | $4,682,208 | $8,696,284 | $2,757,405 | 2 | $5,401,833 | $2,017,906 |
| 2024 | $109,140,604 | $4,918,853 | $7,908,867 | $2,013,844 | 5 | $4,053,582 | $2,321,432 |
| 2023 | $112,078,755 | $5,469,192 | $17,487,593 | $11,975,671 | 3 | $18,496,461 | $4,418,331 |
| 2022 | $124,141,413 | $8,724,488 | $18,968,585 | $17,187,095 | 2 | $47,799,803 | $8,190,501 |
| 2021 | $134,059,414 | $6,537,062 | $906,307 | — | — | — | $3,189,044 |
Leadership & Key People
Officers and directors from IRS filings
Circle Square Foundation is led by Rebecca Rogers, Executive Director on every filing since 2021; 1 of 2 officers listed in 2025 is compensated.
Officers on the 2025 filing
Rebecca Rogers
Executive Director
On filings since 2021
25 hrs/week
$67K (2021) → $98K (2025)
Kenneth D Colen
Trustee
On filings since 2021
20 hrs/week
No compensation reported
Data from IRS Form 990 filings, 2021–2025. "On filings since" is the earliest filing we hold that lists the person; hours are average hours per week as reported.
Compensation Overview
From 2025 IRS filing
The highest reported compensation on the 2025 filing was $98K, to Rebecca Rogers (Executive Dir.).
Frequently asked questions about Circle Square Foundation
How much does Circle Square Foundation give each year?
Circle Square Foundation gave $2.8M across 2 grants in 2025, according to its 2025 IRS Form 990-PF. In 2024 it gave $2.0M across 5 grants.
How large is Circle Square Foundation?
Circle Square Foundation reported $105.1M in total assets on its 2025 IRS Form 990-PF. Its revenue that year was $4.7M.
What is Circle Square Foundation?
Circle Square Foundation is a private foundation focused on Recreation & Sports, based in Ocala, FL. It holds $105.1M in total assets as of 2025.
Where does Circle Square Foundation operate?
Circle Square Foundation has awarded grants in Florida.
What is Circle Square Foundation's EIN?
Circle Square Foundation's EIN (Employer Identification Number) is 83-6900931. IRS Form 990 filing data is available on this page for 2021–2025.
Data last updated September 2026. Sourced from IRS Form 990-PF filings.
Data update history
(6)
When this profile's IRS filing data changed on Grantable
- Updated Form 990-PF for fiscal year 2021 (received by the IRS February 15, 2022)
- Updated Form 990-PF for fiscal year 2022 (received by the IRS March 15, 2023)
- Updated Form 990-PF for fiscal year 2023 (received by the IRS February 13, 2024)
- Updated Form 990-PF for fiscal year 2024 (received by the IRS May 1, 2025)
- Updated Form 990-PF for fiscal year 2025 (received by the IRS February 13, 2026)
- IRS filings on file for fiscal years 2021–2025
Live grants for the work Circle Square Foundation funds
Recreation & Sports Open opportunities, soonest deadline first.
Explore Open Grants
Browse active grant opportunities in Circle Square Foundation's focus areas in our free grants database
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Figures come from Circle Square Foundation's IRS filings (methodology). AI-written summaries, news items and logos are not covered by the open licence. Spot an error? Email hello@grantable.co.
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