Investor profile - MA
David Pennybaker
David Pennybaker is a real estate investor and operator based in Boston-Worcester, MA-NH. Public filings show activity across 270 properties held through 43 holding companies. Recent mortgage relationships include The Village Bank, VILLAGE BANK, and Cardinal Capital Group.
David's Activity
As of December 2025, public records show approximately $76.9M in recorded mortgage exposure linked to this investor across at least 90 mortgage filings and 270 properties held through 43 holding companies. Activity appears concentrated in residential and multifamily assets recorded between 2014 and 2025.
Primary Geography
Boston-Worcester, MA-NH
ZIP codes: 02465, 02458, 02464, 02493, and 02459
Most recorded activity for this investor appears in NEWTON, WALTHAM, WESTON, NEWTON HIGHLANDS, and NATICK.
Property Type Breakdown
Associated Entities (43)
MA · 2 properties · 14 mortgages
MA · 1 property · 13 mortgages
MA · 0 properties · 9 mortgages
+40 more not shown
Mortgages (90)
Top Lenders
| Date | Amount | Status | Lender | Borrower | Address |
|---|---|---|---|---|---|
| 10/27/2025 | $600k | Open | Guaranteed Rate Affinity, LLC | IMPERIAL HOME DEVELOPMENT LLC | 10 FOUNDRY AVE, WALTHAM, MA 02453 |
| 03/07/2025 | $3.0M | Open | The Village Bank | PINK CHERRIES LLC | - |
| 10/11/2024 | $200k | Closed | Winchester Savings Bank | 73 CLOVERDALE ROAD REALTY LLC | 71 CLOVERDALE RD, NEWTON, MA 02461 |
+87 more not shown
Owned Properties (270)
| Address | Deeded owner | Status | Consideration |
|---|---|---|---|
| 10 FOUNDRY AVE, WALTHAM, MA 02453 | IMPERIAL HOME DEVELOPMENT LLC | Owns - 2 mos | $800k |
| 25 JOHNSON PL, AUBURNDALE, MA 02466 | ELIZABETH HERBERT | Sold | $1.8M |
| 130 NONANTUM RD, NEWTON, MA 02458 | CROSS COUNTRY MORTGAGE LLC | Sold | $1.5M |
+267 more not shown
FAQ
What type of real estate does this investor focus on?
Associated mortgages and deeds show activity in residential, multifamily, and commercial properties across Boston-Worcester, MA-NH.
What companies is David Pennybaker associated with?
David Pennybaker is associated with 43 entities based on extracted signatures from public records. Key entities include VESUVIUS REALTY DEVELOPMENT LLC, CORSI REALTY LLC, 956 WALNUT STREET LLC, 24 YALE ROCCO LLC, and FOUR CORNERS GROUP LLC.
How many properties are associated with this investor?
At least 270 properties are associated with David Pennybaker and the entities they control, based on signatures extracted from recorded documents connecting David Pennybaker to the entities.
Which lenders has this investor worked with?
Recent mortgage activity references The Village Bank, VILLAGE BANK, and Cardinal Capital Group, indicating a mix of lending relationships.
How recent is their activity?
Records show activity from 2014 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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