Investor profile - MA
Gilbert Winn
Gilbert Winn is a real estate investor and operator based in Boston-Worcester, MA-NH. Public filings show activity across 119 properties held through 37 holding companies. Recent mortgage relationships include MassHousing, Bank of America, and BOSTON HOUSING AUTHORITY.
Gilbert's Activity
As of December 2025, public records show approximately $984.8M in recorded mortgage exposure linked to this investor across at least 96 mortgage filings and 119 properties held through 37 holding companies. Activity appears concentrated in residential and misc assets recorded between 2010 and 2025.
Primary Geography
Boston-Worcester, MA-NH
ZIP codes: 01852, 02124, 02128, 02116, and 02445
Most recorded activity for this investor appears in BOSTON, LOWELL, DORCHESTER CENTER, BROOKLINE, and HYANNIS.
Property Type Breakdown
Associated Entities (37)
MA · 2 properties · 11 mortgages
MA · 0 properties · 10 mortgages
MA · 2 properties · 8 mortgages
+34 more not shown
Mortgages (96)
Top Lenders
$381.5M · 27 loans
$135.5M · 4 loans
$103.1M · 3 loans
| Date | Amount | Status | Lender | Borrower | Address |
|---|---|---|---|---|---|
| 12/17/2025 | $22.5M | Open | MassHousing | NEWTON GARDENS LLC | 83 FARWELL ST, NEWTON, MA 02460 |
| 12/17/2025 | $6.6M | Open | Massachusetts Department of Housing and Community Development | NEWTON GARDENS LLC | - |
| 09/23/2025 | $5.0M | Open | MassHousing | NEWTON GARDENS LLC | 83 FARWELL ST, NEWTONVILLE, MA |
+93 more not shown
Owned Properties (119)
| Address | Deeded owner | Status | Consideration |
|---|---|---|---|
| 83 FARWELL ST, NEWTON, MA 02460 | NEWTON GARDENS LLC | Owns - 3 mos | $38.0M |
| 440 TREMONT ST, BOSTON, MA 02116 | EVA WHITE REDEVELOPMENT LP | Owns - 12 mos | $5.4M |
| 72 WAYLAND ST, BOSTON, MA 02125 | PHILLIPS BROOKS II LP | Owns - 14 mos | $10 |
+116 more not shown
FAQ
What type of real estate does this investor focus on?
Associated mortgages and deeds show activity in residential, misc, and multifamily properties across Boston-Worcester, MA-NH.
What companies is Gilbert Winn associated with?
Gilbert Winn is associated with 37 entities based on extracted signatures from public records. Key entities include HEADING HOME INC, ADDEN REDEVELOPMENT LLC, WATSON REDEVELOPMENT LP, BRIGHTON MARINE HOUSING LP, and CLIPPERSHIP APARTMENTS LP.
How many properties are associated with this investor?
At least 119 properties are associated with Gilbert Winn and the entities they control, based on signatures extracted from recorded documents connecting Gilbert Winn to the entities.
Which lenders has this investor worked with?
Recent mortgage activity references MassHousing, Bank of America, and BOSTON HOUSING AUTHORITY, indicating a mix of lending relationships.
How recent is their activity?
Records show activity from 2010 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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