Windover Foundation

The Windover Foundation operates as a deliberately discreet, trustee-led family philanthropy administered through the Nutter McClennen & Fish law firm at 155 Seaport Blvd, Boston. With $17 million in assets and approximately $1 million in annual grantmaking, it occupies the mid-tier of New England private foundations — large enough to make meaningful multi-year commitments, but small and personal enough that every grant reflects direct trustee judgment.

The giving philosophy is grounded in geographic affinity and long-term relationship. Fifty-one percent of documented grants flow to Maine, with Kennebec County institutions — Augusta Teen Center, Children's Center of Augusta, Kennebec Historical Society, Travis Mills Foundation — receiving consistent support suggesting a personal connection to the Augusta and mid-Maine region. Massachusetts (particularly Boston and Brookline) accounts for 37% of grants, with the remainder distributed across New Hampshire, New York, Pennsylvania, Maryland, and Florida.

All documented grants carry a 'GENERAL' designation, meaning the foundation funds general operating budgets rather than project-restricted awards. This signals a funder that prioritizes organizational trust, preferring to back stable institutions over funding discrete initiatives. Repeat grantees reinforce this philosophy: Great Pond Mountain Conservation Trust (2 grants, $250,000 total), Kennebec Historical Society (3 grants, $40,000 total), Samaritans (2 grants, $100,000 total), and Brookline Center for Community Mental Health (2 grants, $100,000 total) all reflect multi-year relationships.

With no formal application process and no published deadlines, the pathway begins with a concise letter of inquiry to John A. McBrine at Nutter McClennen — (617) 439-2781, 155 Seaport Blvd, Boston MA 02210 — the foundation's administrative contact. Cold online submissions or unsolicited full proposals are unlikely to be received. Organizations best positioned are those with deep Maine roots (especially Kennebec County or mid-coast), established track records of 5+ years, programming in conservation, mental health/crisis services, children and youth, or arts and historic preservation, and ideally a warm introduction through the Maine or Boston legal and nonprofit community. The Hastings family trustees (Thomas Hastings and Dr. Diane Hastings) and trustee Susanna Fuller are the ultimate decision-makers; any professional or civic overlap with these individuals represents the highest-value entry point.

The Windover Foundation has maintained a stable asset base of approximately $17 million since at least 2012, fluctuating narrowly between $16.6M (FY2015) and $17.97M (FY2020). This consistency reflects disciplined endowment management: the foundation receives no external contributions (contributions received: $0 in all available years), deriving all income from investment dividends (~48%) and asset sales (~52%).

Annual grantmaking is more variable. Grants paid peaked at $2.07M in FY2015, contracted sharply to $188,000 in FY2020 (a COVID-era pullback), and recovered to a steady $919,000–$1.06M range in FY2021–FY2023. The most recent filing (FY2024-25) shows approximately $992,880–$1.14M distributed across 34 grants — a notable increase from 22 grants in FY2023, with total dollars held flat, suggesting the foundation is broadening its distribution base.

Grant size analysis: Across 57 documented grants totaling $2.94M, the raw average is $51,642 — significantly inflated by three Schwab Charitable Fund contributions totaling $790,000 (donor-advised fund pass-throughs, not accessible to external applicants). Excluding these transfers, the effective direct grantmaking range runs from $2,500 (Volunteers of America) to $200,000 (Great Pond Mountain Conservation Trust, most recent cycle), with a median of approximately $25,000 and the largest cluster at $25,000–$75,000. Enriched data confirms: typical minimum $12,500, maximum $125,000, median $18,000, average $37,600.

By geography: Maine dominates at 51% of grants (29 of 57), followed by Massachusetts at 37% (21 grants). Within Maine, Kennebec County and mid-coast organizations receive the heaviest concentration. Florida, Pennsylvania, Maryland, New Hampshire, and New York each claim 1–3 grants.

By program area (estimated from grantee analysis): Conservation and environment ~25% (Great Pond Mountain Conservation Trust, Maine Appalachian Trail Club, Kennebec Land Trust, Gulf of Maine Research Institute, Greater Lovell Land Trust, Audubon Seabird Institute); children/youth/human services ~25% (Children's Hospital, Children's Center of Augusta, KidsPeace, Junior Achievement, Saint Andre Home, Pine Tree Society); mental health/crisis services ~20% (Samaritans, Brookline Center for Community Mental Health, DeNovo Center, Riverside Community Care, Mid-Coast Recovery Coalition); arts/culture/historic preservation ~15% (Odyssey Opera Company, Kennebec Historical Society, First Amendment Museum, Artstream); and general community support ~15% (Boston Neighborhood Support, Cambridge Community Center, Tedford Housing, Travis Mills Foundation).

The table below compares Windover to its five closest asset-size peers as identified in foundation databases. All peers fall in the $17.0M–$17.1M asset range:

None of the four comparable-asset peers publish websites or disclosed grantmaking data, reflecting how common discreet private family philanthropy is at this asset level. What distinguishes Windover within this cohort is the breadth and specificity of its documented grantmaking — 57 grants across a clearly mapped thematic portfolio — and its geographic anchoring in a specific sub-state region (southern Maine / Kennebec County). Organizations competing for similar funding in the Maine/New England region should also evaluate the Maine Community Foundation (much larger, open applications), Elmina B. Sewall Foundation (Maine-focused conservation), and the Betterment Fund (Maine, human services) — all of which have published application processes and broader applicant pools, making Windover's relationship-based model a higher-effort but lower-competition pathway for well-aligned organizations.

No press releases, public announcements, or leadership changes from 2025–2026 appeared in any web searches. The Windover Foundation maintains an exceptionally low public profile: its registered website (windover.org) resolves to an unrelated school, it has no social media presence, no grants page, and no publicly listed email contact. This is consistent with a family philanthropy deliberately managed outside public channels.

The most recent confirmed IRS filing was submitted November 6, 2025, covering FY2024-25. This filing shows 34 grants totaling approximately $992,880–$1.14M with total assets holding near $17.06M — down slightly from $17.19M in FY2023, reflecting modest investment underperformance. The increase from 22 grants (FY2023) to 34 grants (FY2024-25) is the most notable operational shift in recent years.

Among notable recent grants: Great Pond Mountain Conservation Trust received $200,000 — the largest single documented conservation grant and among the top five grants in the foundation's available history. Kennebec Land Trust received $100,000. Children's Hospital Boston received an estimated $270,000 across multiple grants in recent cycles. Trustee composition — Thomas Hastings, Dr. Diane Hastings, and Susanna Fuller — appears unchanged across all available filings from FY2012 through FY2024, indicating stable family stewardship with no succession transition underway. No new program initiatives or priority changes have been publicly disclosed, and the foundation shows no indication of moving toward a formalized or publicly accessible application structure.

Because Windover operates with no formal application process, success depends on navigating its relationship infrastructure rather than mastering a grant form. The following guidance is drawn directly from documented grantee patterns and foundation operating characteristics:

1. Make contact through John A. McBrine at Nutter McClennen. He is the attorney managing foundation operations and the listed primary contact. Reach him by phone at (617) 439-2781 or by letter at 155 Seaport Blvd, Boston MA 02210. A brief introductory call to confirm the current intake preference (letter vs. email) is a worthwhile first step.

2. Lead with Maine and Kennebec County alignment. If your organization operates in or primarily serves Kennebec County or southern Maine, make that your opening sentence. These organizations receive 51% of all grants and receive the most consistent multi-year support.

3. Request general operating support — not project funding. Every documented Windover grant is unrestricted general support. Do not propose a named initiative, pilot program, or capital campaign unless explicitly invited to do so.

4. Target the right program areas. The five strongest thematic bets by grantee history: (1) land conservation in Maine, (2) mental health and crisis intervention in Massachusetts or Maine, (3) children's and youth services in central Maine, (4) arts and cultural institutions in New England, and (5) historic preservation in Maine river communities. Organizations falling outside these clusters face a much steeper path.

5. Demonstrate longevity and community roots. First grants almost always go to organizations that have existed 10+ years. The Kennebec Historical Society (founded 1891), Samaritans (founded 1974), and Children's Hospital Boston (founded 1869) are exemplar grantees. Frame your track record prominently.

6. Size your ask to precedent. Request $25,000–$75,000 for a first grant. The median documented direct grant is ~$25,000, and the modal cluster is $25,000–$75,000. A first ask above $100,000 is likely to be declined absent an existing relationship.

7. Be patient and persistent without being pushy. With no published review cycle, expect 60–90 days for any acknowledgment. Follow up once, professionally, approximately 6 weeks after your initial contact. Do not follow up more than twice in a single outreach cycle.

8. Avoid Schwab Charitable Fund comparisons. The three largest 'grants' in the record are donor-advised fund contributions — these are not a grantee pathway, and referencing them as precedent in your application would signal unfamiliarity with the foundation's actual direct grantmaking.