Investor Profile - FL
Jay Sheppard
Jay Sheppard is a real estate investor and operator based in Pensacola, FL. Public filings show activity across 32 properties held through 7 holding companies. Recent mortgage relationships include Trustmark Bank, SmartBank, and THE LAWRENCE N KLINE REVOCABLE TRUST.
Jay's Activity
As of June 2026, public records show approximately $1.0M in recorded mortgage exposure linked to this investor across at least 9 mortgage filings and 32 properties held through 7 holding companies. Activity appears concentrated in residential and commercial assets recorded between 2016 and 2025.
Associated People
Primary Geography
Pensacola, FL
ZIP codes: 32505, 32507, 32506, 32526, and 32533
Most activity in PENSACOLA, CANTONMENT, and NEPTUNE BEACH.
Property Type Breakdown
Associated Entities (7)
FL · 14 properties · 5 mortgages
FL · 2 properties · 2 mortgages
+5 more entities not shown
Mortgages (9)
Top Lenders
$364k · 1 loan
$244k · 2 loans
$185k · 1 loan
| Date | Amount | Status | Lender | Borrower | Address |
|---|---|---|---|---|---|
| 08/19/2024 | $200k | Open | SmartBank | CSS LLC | 2402 HWY 297A, CANTONMENT, FL 32533 |
| 10/04/2021 | $364k | Open | Trustmark Bank | CSS LLC | 6506 CHICAGO AVE, PENSACOLA, FL 32526 |
+7 more not shown
Owned Properties (32)
| Address | Deeded owner | Status | Consideration |
|---|---|---|---|
| 5708 CLEARWATER AVE, PENSACOLA, FL 32505 | CSS LLC | Sold | $81k |
| 100 PACE PKWY, CANTONMENT, FL 32533 | CSS LLC | Owns - 4.6 yrs | $51k |
+30 more not shown
FAQ
What type of real estate does this investor focus on?
Associated mortgages and deeds show activity in residential, commercial, and vacant properties across Pensacola, FL.
What companies is Jay Sheppard associated with?
Jay Sheppard is associated with 7 entities based on extracted signatures from public records. Key entities include CSS LLC, DOWNTOWN PROPERTY INV LLC, PENSACOLA PROPERTY INVESTMENTS LLC, 18KINGSFIELD LLC, and MHPARKS LLC.
How many properties are associated with this investor?
At least 32 properties are associated with Jay Sheppard and the entities they control, based on signatures extracted from recorded documents connecting Jay Sheppard to the entities.
Which lenders has this investor worked with?
Recent mortgage activity references Trustmark Bank, SmartBank, and THE LAWRENCE N KLINE REVOCABLE TRUST, 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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