Investor Profile - MD
Kevin Oleary
Kevin Oleary is a real estate investor and operator based in Washington-Baltimore, DC-MD-VA. Public filings show activity across 40 properties held through 4 holding companies. Recent mortgage relationships include Bank of Charles Town, REVERE BANK, and CNB Bank.
Kevin's Activity
As of June 2026, public records show approximately $1.1M in recorded mortgage exposure linked to this investor across at least 22 mortgage filings and 40 properties held through 4 holding companies. Activity appears concentrated in residential and exempt assets recorded between 2016 and 2025.
Associated People
Primary Geography
Washington-Baltimore, DC-MD-VA
ZIP codes: 21740, 21742, 21733, 21767, and 21782
Most activity in HAGERSTOWN, FAIRPLAY, SHARPSBURG, and MAUGANSVILLE.
Property Type Breakdown
Associated Entities (4)
MD · 8 properties · 12 mortgages
MD · 12 properties · 10 mortgages
+2 more entities not shown
Mortgages (22)
Top Lenders
| Date | Amount | Status | Lender | Borrower | Address |
|---|---|---|---|---|---|
| 02/01/2024 | $85k | Closed | Bank of Charles Town | TRD HOLDINGS LLC | 316 E FRANKLIN ST, HAGERSTOWN, MD 21740 |
| 09/03/2020 | $58k | Open | Bank of Charles Town | HIGH GROUND HOLDINGS LLC | 716 MARYLAND AVE, HAGERSTOWN, MD 21740 |
+20 more not shown
Owned Properties (40)
| Address | Deeded owner | Status | Consideration |
|---|---|---|---|
| 437 N MULBERRY ST, HAGERSTOWN, MD 21740 | HIGH GROUND HOLDINGS LLC | Sold | $90k |
| 424 GEORGE ST, HAGERSTOWN, MD 21740 | HIGH GROUND HOLDINGS LLC | Sold | $78k |
+38 more not shown
FAQ
What type of real estate does this investor focus on?
Associated mortgages and deeds show activity in residential, exempt, and vacant properties across Washington-Baltimore, DC-MD-VA.
What companies is Kevin Oleary associated with?
Kevin Oleary is associated with 4 entities based on extracted signatures from public records. Key entities include HIGH GROUND HOLDINGS LLC, TRD HOLDINGS LLC, KO MOVE INC, and DOUBLE TROUBLE VENTURES LLC.
How many properties are associated with this investor?
At least 40 properties are associated with Kevin Oleary and the entities they control, based on signatures extracted from recorded documents connecting Kevin Oleary to the entities.
Which lenders has this investor worked with?
Recent mortgage activity references Bank of Charles Town, REVERE BANK, and CNB Bank, 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 2024.
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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