Circle Square Foundation

Private foundation · Grantmaker Ocala, FL EIN: 83-6900931

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

Colen Family Charitable Trust: $2.7MColen Family Charitable Trust$2.7MCommunity Foundation for Ocala: $26KCommunity Foundation for Ocala$26K

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

8<$50K$50–100K$100–250K$250–500K$500K–1M2$1–5M2$5M+

The most common grant size was under $50K: 8 grants of 12 (67%).

Geographic Focus

Where this funder awards grants

Grant Distribution by State

1state

Share of 2025 grant dollars across all 2 itemized grants.

States

Cities

Ocala

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

$0$5M$10M$15M$20M0 grants2021 2 grants2022 3 grants2023 5 grants2024 2 grants2025

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

RecipientPurposeAmount
Colen Family Charitable Trust Ocala, FLCharitable Contribution$2,731,905
Community Foundation for Ocala Ocala, FLCharitable Contribution$25,500
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Financial History

Multi-year comparison from IRS filings

Figures from IRS filings, by filing year
Filing yearTotal AssetsRevenueExpensesGrants paidGrantsQualifying DistributionsNet Investment Income
2025$105,112,520$4,682,208$8,696,284$2,757,4052$5,401,833$2,017,906
2024$109,140,604$4,918,853$7,908,867$2,013,8445$4,053,582$2,321,432
2023$112,078,755$5,469,192$17,487,593$11,975,6713$18,496,461$4,418,331
2022$124,141,413$8,724,488$18,968,585$17,187,0952$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

Rebecca Rogers — Executive Dir.: $98KRebecca RogersExecutive Dir.$98K

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

  1. Updated Form 990-PF for fiscal year 2021 (received by the IRS February 15, 2022)
  2. Updated Form 990-PF for fiscal year 2022 (received by the IRS March 15, 2023)
  3. Updated Form 990-PF for fiscal year 2023 (received by the IRS February 13, 2024)
  4. Updated Form 990-PF for fiscal year 2024 (received by the IRS May 1, 2025)
  5. Updated Form 990-PF for fiscal year 2025 (received by the IRS February 13, 2026)
  6. IRS filings on file for fiscal years 2021–2025

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The filing figures on this page are open data under CC BY 4.0. About GrantGraph Open

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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