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Highland Street Connection

Private foundation · Grantmaker Newton, MA EIN: 04-3048298 Website

Highland Street Connection, which operates as the Highland Street Foundation, is a private foundation based in Newton, Massachusetts. Its stated mission is to address pressing needs and concerns for children and families in Massachusetts and California, providing access and opportunities in areas including education, housing, mentorship, health care, the environment, and the arts.

Key facts about Highland Street Connection

In short: Highland Street Connection gave $4.4M across 410 grants in 2024 (avg $11K), mostly in Massachusetts. 22% of 2024 grantees were new. Source: 2024 IRS Form 990-PF.

EIN
04-3048298
Latest 990 filing
Form 990-PF, 2024
Annual giving (2024)
$4,400,675
Grants made (2024)
410
Average grant
$10,733
Median grant
$5,000
New grantees (estimate)
22% first-time grantees (67 of 303, 2024)
Total assets
$60,381,854
Primary geography
Massachusetts (79% of itemized 2024 grant dollars)
Accepts unsolicited proposals
No
How to apply
The foundation does not accept unsolicited requests. Full details ↓

Data from IRS Form 990-PF, 2024; updated September 2026. New grantees are estimated by matching recipient names across years (methodology). Application details from Grantable's research on the foundation's public materials; confirm on its website before applying.

Financial Overview

From 2024 IRS Form 990-PF · View filing

Total Assets

$60.4M

-9.6% YoY

Annual Giving

$4.4M

+11.2% YoY

Grant Count

410

+51.3% YoY

Avg Grant Size

$11K

-26.5% YoY

Under IRS private-foundation payout rules, Highland Street Connection reported a distributable amount of $3.5M for 2024 — the minimum it must pay out in qualifying distributions.

Is Highland Street Connection open to new grantees?

22%

first-time grantees, 2024

In 2024, 67 of 303 grantees (22%) were first-time recipients. First grants averaged $9K; repeat grants $16K. How we count

Medians: $3K first-time, $8K repeat.

  • 66% of 2024 grantees were also funded in 2023. Method
  • Giving grew 25% from 2021 to 2024. Method
  • In 2024 it paid out 190% of its IRS minimum distribution (the 5% rule). Method

Estimate from itemized grant lists in IRS Form 990-PF filings (2020–2024). Recipient names are matched across years, so a renamed or misspelled grantee can look new; grants to individuals are left out. Methodology.

Research compiled by Grantable AI from public sources. Last updated September 2026.

Mission & Focus Areas

The foundation’s mission is to address the most pressing needs and concerns for children and families in Massachusetts and California. Its stated areas of interest include education, youth programming and mentoring, housing and homelessness prevention, the environment, health care, and the arts.

Examples of supported organizations illustrate the range of grantees. The Boston Symphony Orchestra describes its mission as making music and providing educational and training programs. The Boston Public Library Fund says it supports the Boston Public Library so it can remain viable, engaging, accessible, and free. English for New Bostonians describes its work as ensuring access to high-quality English classes for adult immigrants. Crossroads says it provides people with disabilities training and experience in employment, residential, and community involvement.

Grantmaking

In 2024, the foundation reported 410 grants totaling $4,400,675. Awards ranged from $400 to $100,000, with a median of $5,000.

Open Grants

1 open opportunity from Highland Street Connection

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Geographic Focus

Where this funder awards grants

The foundation says it primarily funds programs within Massachusetts and also supports a limited number of organizations outside the state at trustees’ request. It does not fund organizations based outside the United States. In 2024, 79% of grant dollars went to recipients in Massachusetts, 16% to California, 2% to Nevada, and 1% each to Maine and Colorado.

Grant Distribution by State

20states

Share of 2024 grant dollars across all 410 itemized grants.

Cities

BostonPalm DesertWorcesterNew BedfordLawrenceJamaica PlainWestonDenmarkDorchesterNeedhamRancho MirageCambridgePalm SpringsNatickBraintreeIndioRoxburyBrightonHolyokeWaltham

Giving Over Time

Total grant dollars and number of grants per year

$0$2M$4M$6M306 grants2020 220 grants2021 242 grants2022 271 grants2023 410 grants2024

From 2020 to 2024, annual grant giving ranged from $3.5M (2021) to $4.9M (2020). In 2024 it made 410 grants totaling $4.4M.

Grant Insights

How this funder distributes its grants

Top Recipients

Top 10 recipients in 2024

Camp Harbor View: $187K across 6 grantsCamp Harbor View$187K · 6 grantsYMCA of Greater Boston: $184K across 7 grantsYMCA of Greater Boston$184K · 7 grantsLiving Desert: $157K across 5 grantsLiving Desert$157K · 5 grantsBoston Symphony Orchestra: $116K across 3 grantsBoston Symphony Orchestra$116K · 3 grantsCity of Boston Scholarship Fund City of Boston: $110K across 2 grantsCity of Boston ScholarshipFund City of Boston$110K · 2 grantsEisenhower Health Foundation: $110K across 2 grantsEisenhower Health Foundation$110K · 2 grantsBPS Foundation: $100KBPS Foundation$100KPalm Springs International Film Society: $75KPalm Springs InternationalFilm Society$75KSquashbusters: $70K across 3 grantsSquashbusters$70K · 3 grantsXavier College Preparatory High School: $70K across 2 grantsXavier College PreparatoryHigh School$70K · 2 grants

The largest 2024 recipient was Camp Harbor View ($187K across 6 grants). Together the top 10 received $1.2M.

Grant Size Distribution

1,449 grants across all recorded years

1344<$50K66$50–100K36$100–250K3$250–500K$500K–1M$1–5M$5M+

The most common grant size was under $50K: 1,344 grants of 1,449 (93%).

Giving History

Grant recipients and amounts by year

RecipientPurposeAmount
Boston Symphony Orchestra Boston, MAFor Arts and Culture.$100,000
BPS Foundation Las Vegas, NVFor Educational Programs.$100,000
Camp Harbor View Boston, MAFor Youth Programming.$100,000
City of Boston Scholarship Fund City of Boston Boston, MAFor Arts and Culture.$100,000
Eisenhower Health Foundation Rancho Mirage, CAFor Healthcare.$100,000
Living Desert Palm Desert, CAFor Arts and Culture.$100,000
YMCA of Greater Boston Boston, MAFor Community.$100,000
Palm Springs International Film Society Palm Springs, CAFor Arts and Culture.$75,000
Xavier College Preparatory High School Palm Desert, CAFor Educational Programs.$60,000
Be Like Brit Foundation Worcester, MAFor Empowerment.$50,000

Financial History

Multi-year comparison from IRS filings

Filing year Assets Revenue Expenses Grants Grant count
2024 $60,381,854 $6,706,408 $8,160,981 $4,400,675 410
2023 $66,830,483 $6,029,075 $7,928,618 $3,959,100 271
2022 $72,739,346 $2,828,124 $7,425,387 $3,918,739 242
Revenue
Expenses
Qualifying Distributions
Net Investment Income
$0$2.5M$5M$7.5M$10M2020 2021 2022 2023 2024
Metric202420232022
Total Assets$60,381,854$66,830,483$72,739,346
Revenue$6,706,408$6,029,075$2,828,124
Expenses$8,160,981$7,928,618$7,425,387
Qualifying Distributions$6,745,145$6,584,697$6,092,167
Net Investment Income$5,417,546$4,756,192$1,576,261
Distributable Amount$3,547,048$1,199,349$3,812,678

Data update history

When this profile's IRS filing data changed on Grantable

  1. IRS filings on file for fiscal years 2020–2024

Leadership & Key People

Leadership team and compensation from IRS filings

The 2024 filing lists JoAnn McGrath, David J. McGrath III, Sean P. McGrath, and Michael Keating as trustees, and Blake Jordan as executive director.

Highland Street Connection is led by Blake Jordan, Executive Director on every filing since 2020; 1 of 5 officers listed in 2024 is compensated.

Officers on the 2024 filing

  • Blake Jordan

    Executive Director

    On filings since 2020

    40 hrs/week

    $416K (2020) → $494K (2024)

  • David J. McGrath III

    Trustee

    On filings since 2020

    8 hrs/week

    No compensation reported

  • Joann McGrath

    Trustee

    On filings since 2020

    8 hrs/week

    No compensation reported

  • Michael Keating

    Trustee

    On filings since 2020

    8 hrs/week

    No compensation reported

  • Sean P. McGrath

    Trustee

    On filings since 2020

    8 hrs/week

    No compensation reported

Data from IRS Form 990 filings, 2020–2024. "On filings since" is the earliest filing we hold that lists the person; hours are average hours per week as reported.

Compensation Overview

From 2024 IRS filing

Blake Jordan — Executive Director: $494KBlake JordanExecutive Director$494K

The highest reported compensation on the 2024 filing was $494K, to Blake Jordan (Executive Director).

Contact

Mailing address: 2223 Washington Street 104, Newton, MA 02462
Phone: (617) 969-8900
Website: https://www.highlandstreet.org

Frequently asked questions about Highland Street Connection

How much does Highland Street Connection give each year?

Highland Street Connection gave $4.4M across 410 grants in 2024, according to its 2024 IRS Form 990-PF. In 2023 it gave $4.0M across 271 grants.

What is Highland Street Connection's typical grant size?

Highland Street Connection's median grant in 2024 was $5,000, and its average grant was $10,733, across 410 grants on its 2024 IRS Form 990-PF. Organizations receiving their first grant from Highland Street Connection that year got $9K on average.

Where does Highland Street Connection give grants?

Highland Street Connection gives mostly in Massachusetts: 79% of the grant dollars itemized on its 2024 IRS Form 990-PF went to recipients there. The next largest state was California (16%). The most frequent recipient cities were Boston, MA (151 grants), Palm Desert, CA (26 grants), New Bedford, MA (19 grants) and Worcester, MA (14 grants).

Does Highland Street Connection give general operating support?

Not in 2024: none of the 410 grants with a stated purpose on Highland Street Connection's 2024 IRS Form 990-PF were described as general or operating support. Recurring purposes include "For Community." (131 grants), "For Arts and Culture." (102 grants) and "For Educational Programs." (53 grants).

Who are Highland Street Connection's largest grantees?

Highland Street Connection's largest 2024 grantees include Camp Harbor View ($186,500 across 6 grants), YMCA of Greater Boston ($183,500 across 7 grants) and Living Desert ($156,500 across 5 grants), according to its 2024 IRS Form 990-PF. Together they received 12% of its itemized 2024 grant dollars.

How large is Highland Street Connection?

Highland Street Connection reported $60.4M in total assets on its 2024 IRS Form 990-PF. It paid out $6.7M in qualifying distributions that year, against a required minimum of $3.5M (roughly 5% of its investment assets).

What does Highland Street Connection fund?

The foundation’s mission is to address the most pressing needs and concerns for children and families in Massachusetts and California. Its stated areas of interest include education, youth programming and mentoring, housing and homelessness prevention, the environment, health care, and the arts. See mission & focus areas ↑

How do I apply for a grant from Highland Street Connection?

The foundation does not accept unsolicited requests. Eligibility and process details are in the grantmaking section of this profile. See how to apply ↑

What is Highland Street Connection's EIN?

Highland Street Connection's EIN (Employer Identification Number) is 04-3048298. IRS Form 990 filing data is available on this page for 2020–2024.

Does Highland Street Connection accept unsolicited proposals?

No, according to Grantable's research on the foundation's published guidelines. See how to apply ↑

Data last updated September 2026. Sourced from IRS Form 990-PF filings. Research dossier generated September 2026.

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