Chesnee Cogswell was born on Tortola, BVI and raised on the water sailing throughout the Caribbean with his family as well as in Cocoa Beach, Florida where he caught the fishing bug. He has lived aboard many boats over his lifetime and has been involved in extensive refit projects of varying scope and complexity. Now back living full time in the BVI for over a decade, Chesnee is raising a family of his own.
He joined the team in 2018 as BVI Yacht Sales re-expanded its sales force following Hurricane Irma in 2017. Before joining the company, Chesnee was a very active charter captain for numerous charter operators in the BVI, giving him firsthand experience sailing a wide range of charter yachts across many makes and models. His experience also extends into the sportfishing world, having participated in numerous sportfishing tournaments as well as private and charter fishing programs over the years. These experiences have given him a strong advantage in the powerboat market.
Since joining BVI Yacht Sales, Chesnee has fully committed himself to his role, and his results reflect that dedication. He has consistently outperformed other brokerages in the Caribbean as an individual broker and, in 2025, acted as buyer’s broker on the largest sale in BVI Yacht Sales history to date. His hard work and long-term commitment have placed him among the top-performing yacht brokers in the Caribbean year after year. This track record, combined with his leadership and experience, earned him the role of Yacht Sales Director, where he now shares his knowledge and helps guide the team in serving clients and selling more boats!
Sold Listings
2021 Fountaine Pajot My Ty
$3,300,000
67 ft
2012 Beneteau Erocribar II
$179,000
54 ft
2019 Hanse Chill Time
$682,500
54 ft
Nanny Cay Marina
2023 Hanse VaVaVoom
$699,000
51 ft
Nanny Cay Boatyard
1997 Feeling Long Reach
$65,000
48 ft
Cruising
2002 Beneteau Nanito II
$88,000
47 ft
Nanny Cay
2012 Naval Yachts Sea Wolf
$275,000
45 ft
1987 Gulfstar Gallivant
$99,000
45 ft
2019 Leopard Judine
$499,000
45 ft
Tortola
2008 Cabo LALALAND
$349,000
45 ft
2015 Hanse Valhalla
$219,000
45 ft
Charleston South Carolina
2018 Aquila Jewel Box
$549,000
44 ft
Nanny Cay Marina
2002 Jeanneau Options
$119,000
43 ft
Fajardo
2021 Neel Anegada III
$339,000
43 ft
Nanny Cay Marina
1981 Tartan Receta
$99,500
42 ft
Chaguaramas
2011 Beneteau Libertas
$69,500
40 ft
Nanny Cay, Tortola
2016 Broadblue A'R Mor Dirion
$249,000
40 ft
Nanny Cay
2006 Bavaria Life Aquatic
$99,000
39 ft
Salinas
2017 Axopar Silver Fox
$115,000
37 ft
Nanny Cay
2021 Custom Indigo Lander
$275,000
36 ft
Fajardo Puerto Rico
2006 Albin Drifter
$79,000
35 ft
2022 Hanse ASTUR
$149,000
34 ft
Tortola
2019 NauticStar
$69,000
26 ft
Manuel Reef, Tortola
2001 Twin Vee Blue Fin
$55,000
26 ft
Humacao Puerto Rico
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