Tenant Representation
Guiding retail and commercial tenants into the right markets and locations across the region.
Caribbean commercial real estate
James
de Winter
Dorset International Realty, Inc.
Four decades of commercial real estate brokerage — the last thirty focused wholly on the Caribbean, across twenty-six islands and the only firm covering the entire region.
40+
Years in commercial
real estate brokerage
30
Years focused solely
on the Caribbean
26
Islands covered
across the region
'96
Founded Dorset
International Realty
About Jim
A single point of expertise for the entire Caribbean.
James de Winter has more than forty years of commercial real estate brokerage experience across both U.S. and international markets. For the past thirty years he has worked exclusively in the Caribbean, providing commercial transaction brokerage throughout a region spanning twenty-six islands.
In 1996 he founded Dorset International Realty, Inc. — recognizing the need for a firm that could represent international companies seeking expansion or investment in the Caribbean, alongside companies and property owners with existing interests in the region.
Dorset has since become a leading commercial real estate firm working solely in the Caribbean — and the only one that covers the entire region.
“Having traveled these markets for more than sixteen years, I saw the opportunity before the region did — and built a firm to serve it end to end.”
The Region
The only firm covering
the whole Caribbean.
From the Bahamas to Trinidad, Jim advises on single-market and multi-market assignments across the entire archipelago — the depth of a specialist with the reach of the region itself.
The Bahamas
Turks & Caicos
Cayman Islands
Jamaica
Dominican Republic
Puerto Rico
U.S. & British Virgin Islands
St. Maarten
Anguilla
St. Kitts & Nevis
Antigua & Barbuda
Barbados
Trinidad & Tobago
Aruba · Curaçao · Bonaire
St. Lucia
Grenada
+ 9 more territories
Services
Transaction brokerage &
advisory, end to end.
Owner & Landlord Advisory
Representing property owners in leasing, disposition and positioning of commercial assets.
Investor Services
Advising international investors on expansion, acquisition and entry into Caribbean markets.
Transaction Brokerage
Executing deals for regional and international firms on single and multi-market assignments.
Market Research
Commercial and retail-specific market reports, drawing on decades of on-the-ground knowledge.
Multi-Market Strategy
Coordinated programs for companies expanding across several Caribbean territories at once.
Experience
Four decades, one region mastered.
A career spanning the industry's leading global firms — always with the Caribbean at its center.
-
2026 — Present
Dorset International Realty, Inc.
Director of Real Estate — Caribbean · Founder
-
2019 — 2026
JLL
Vice President — Caribbean
-
1999 — 2019
CBRE
Director of Real Estate — Caribbean · Latin America & Caribbean
-
1996 — 1999
Dorset International Realty, Inc.
Founder & Director of Real Estate — Caribbean
Get in touch
Let's talk about
your next move.
Whether you're entering the Caribbean or repositioning existing assets, Jim brings the whole region to the table.