Investor profile - MA
Jacob Dewey
Jacob Dewey is a real estate investor and operator based in Boston-Worcester, MA-NH. Public filings show activity across 9 properties held through 9 holding companies. Recent mortgage relationships include Cape Cod Five, Rockland Trust, and BARNSTABLE AFFORDABLE HOUSING GROWTH AND DEVELOPMENT TRUST FUND.
Jacob's Activity
As of December 2025, public records show approximately $19.5M in recorded mortgage exposure linked to this investor across at least 24 mortgage filings and 9 properties held through 9 holding companies. Activity appears concentrated in vacant and residential assets recorded between 2016 and 2025.
Primary Geography
Boston-Worcester, MA-NH
ZIP codes: 02601, 02670, and 02673
Most recorded activity for this investor appears in HYANNIS, WEST DENNIS, and WEST YARMOUTH.
Property Type Breakdown
Associated Entities (9)
MA · 5 properties · 5 mortgages
MA · 3 properties · 5 mortgages
MA · 1 property · 4 mortgages
+6 more not shown
Mortgages (24)
Top Lenders
$17.8M · 19 loans
$1.2M · 2 loans
$500k · 1 loan
| Date | Amount | Status | Lender | Borrower | Address |
|---|---|---|---|---|---|
| 09/12/2025 | $2.0M | Open | Cape Cod Five | CROCKER STREET HOLDINGS LLC | 24 CROCKER ST, HYANNIS, MA 02601 |
| 11/15/2024 | $500k | Open | BARNSTABLE AFFORDABLE HOUSING GROWTH AND DEVELOPMENT TRUST FUND | CCR HOLDINGS LLC | - |
| 05/24/2024 | $2.5M | Open | Cape Cod Five | CCR HOLDINGS LLC | 50 YARMOUTH RD, HYANNIS, MA 02601 |
+21 more not shown
Owned Properties (9)
| Address | Deeded owner | Status | Consideration |
|---|---|---|---|
| 394 MAIN ST, WEST DENNIS, MA 02670 | ALL CAPE PROPERTY LLC | Owns - 20 mos | $779k |
| 10 PINE GROVE AVE, HYANNIS, MA 02601 | PINE GROVE HOLDINGS LLC | Owns - 3.4 yrs | $207k |
| 24 CROCKER ST, HYANNIS, MA 02601 | CROCKER STREET HOLDINGS LLC | Owns - 3.6 yrs | $1.3M |
+6 more not shown
FAQ
What type of real estate does this investor focus on?
Associated mortgages and deeds show activity in vacant, residential, and multifamily properties across Boston-Worcester, MA-NH.
What companies is Jacob Dewey associated with?
Jacob Dewey is associated with 9 entities based on extracted signatures from public records. Key entities include MIDPOINT PROPERTY LLC, PINE GROVE HOLDINGS LLC, ALL CAPE PROPERTY LLC, CCR HOLDINGS LLC, and LEOS DOGHOUSE LLC.
How many properties are associated with this investor?
At least 9 properties are associated with Jacob Dewey and the entities they control, based on signatures extracted from recorded documents connecting Jacob Dewey to the entities.
Which lenders has this investor worked with?
Recent mortgage activity references Cape Cod Five, Rockland Trust, and BARNSTABLE AFFORDABLE HOUSING GROWTH AND DEVELOPMENT TRUST FUND, indicating a mix of lending relationships.
How recent is their activity?
Records show activity from 2016 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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