Investor profile - MA
Cheryl Penn
Cheryl Penn is a real estate investor and operator based in Boston-Worcester, MA-NH. Public filings show activity across 3 properties held through 17 holding companies. Recent mortgage relationships include Walker & Dunlop, 200300 NORTH END AVENUE CAPITAL, and Northwestern Mutual.
Cheryl's Activity
As of December 2025, public records show approximately $372.5M in recorded mortgage exposure linked to this investor across at least 11 mortgage filings and 3 properties held through 17 holding companies. Activity appears concentrated in commercial and multifamily assets recorded between 2011 and 2025.
Primary Geography
Boston-Worcester, MA-NH
ZIP codes: 02127, 02476, and 01821
Most recorded activity for this investor appears in BOSTON, ARLINGTON, and BILLERICA.
Property Type Breakdown
Associated Entities (17)
MA · 0 properties · 4 mortgages
MA · 0 properties · 3 mortgages
MA · 0 properties · 2 mortgages
+14 more not shown
Mortgages (11)
Top Lenders
$132.4M · 3 loans
$78.7M · 1 loan
$49.0M · 1 loan
| Date | Amount | Status | Lender | Borrower | Address |
|---|---|---|---|---|---|
| 11/19/2025 | $37.1M | Open | Walker & Dunlop | 929 MASS AVE OWNER LLC | 929 MASSACHUSETTS AVE, ARLINGTON, MA 02476 |
| 09/14/2023 | $49.0M | Open | Northwestern Mutual | VAL OWNER LLC | 164 LEXINGTON RD, BILLERICA, MA 01821 558 |
| 10/28/2020 | $9.8M | Open | Walker & Dunlop | CHELSEA PLACE APARTMENTS LLC | - |
+8 more not shown
Owned Properties (3)
| Address | Deeded owner | Status | Consideration |
|---|---|---|---|
| 929 MASSACHUSETTS AVE, ARLINGTON, MA 02476 | 929 MASS AVE OWNER LLC | Owns - 1 mo | $53.6M |
| 164 LEXINGTON RD, BILLERICA, MA 01821 558 | VAL OWNER LLC | Owns - 2.3 yrs | $92.5M |
| 26 W BROADWAY, BOSTON, MA 02127 | RESIDENCES AT TWENTY SIX WEST BROADWAY LLC | Owns - 6.8 yrs | $25.0M |
+0 more not shown
FAQ
What type of real estate does this investor focus on?
Associated mortgages and deeds show activity in commercial and multifamily properties across Boston-Worcester, MA-NH.
What companies is Cheryl Penn associated with?
Cheryl Penn is associated with 17 entities based on extracted signatures from public records. Key entities include ANDOVER COMMONS LLC, SHREWSBURY COMMONS LLC, RESIDENCES AT FIFTY WEST BROADWAY LLC, CORCORAN SKYLINE LLC, and FIRST STONE RUN EAST LLC.
How many properties are associated with this investor?
At least 3 properties are associated with Cheryl Penn and the entities they control, based on signatures extracted from recorded documents connecting Cheryl Penn to the entities.
Which lenders has this investor worked with?
Recent mortgage activity references Walker & Dunlop, 200300 NORTH END AVENUE CAPITAL, and Northwestern Mutual, indicating a mix of lending relationships.
How recent is their activity?
Records show activity from 2011 through 2025, with the most recent mortgage recorded in 2025.
How is associated activity determined?
Elementix uses AI to extract signatures from recorded documents. These signatures are used to determine the relationships between people and entities. This is a novel approach that goes beyond looking at corporate filings and skip-tracing.
The information displayed on this page is compiled from recorded real estate documents, business filings, and other lawfully available sources. Elementix summarizes and analyzes public record activity related to investment real estate and associated business entities. Any contact indicators shown (such as email domain references or partial phone digits) are provided solely as unverified signals and may be incomplete or outdated.
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