About Us

Nick’s Advantage

Born and Raised in the Virgin Islands

Nick Bailey

St. Thomas - For over 70 years the Bailey family has held a position of prominence in business as well as social goings on in St. Thomas. Nicks father, William, known as “Lawyer Bailey”, was a towering figure in Island courtroom proceedings. His mother Kay, was a well-loved, colorful personality, holding court as well with her “Top o’ the Morning” radio show on WSTA.

St. John – In the 1950s the Bailey family spent many summers in Cruz Bay, St. John where, as children, Nick, his brothers, sisters and friends played with St. Johnians shooting marbles and bustin’ tops.

St. Croix – After graduating Colgate University, Nick returned to the V.I. and got a job working for Hess Oil in St. Croix as a shipping agent. While living in St. Croix, he found the time to study and earn a private air pilot’s license. Nick currently holds a multi-engine pilot rating.

NOBODY knows the Virgin Islands more than Nick Bailey. 

25 Years of Real Estate Experience in the Virgin Islands

Nick began his real estate career with John Foster Real Estate in 1985. John Foster Real Estate has been servicing the U.S. Virgin Islands since 1972 and is recognized as the premier brokerage of the Virgin Islands. In 1997, Nick became co-owner and partner of the firm. He currently oversees approximately 20 brokers, agents and support staff.

Nick’s Secret Weapon – his wife, Joyce!

For new property owners, the ins and outs of the USVI Tax landscape can be a daunting proposition. The good news is that there are a myriad of tax benefits and exemptions available for businesses and property owners. Nick’s wife Joyce Bailey has been a CPA in the Virgin Islands for over 25 years. She specializes in tax matters, working through the years with an extensive variety of Virgin Island businesses and individuals as well. Joyce was president of a multimillion EDC company for 5 years. Her knowledge and experience in the field of taxation makes Joyce a valuable tax consultant for Nick’s clients. For more about Tax benefits and exemptions in the Virgin Islands

Nick Bailey

Nick is a true Virgin Islander being born and raised on St Thomas, one of six children, Nick has traveled extensively throughout the globe with his family and is convinced, there is no place better to live and work, than the Virgin Islands.

A frigid several years at Colgate University in upstate New York has been enough winter for him except for the yearly ski trip with his family to Park City Utah. Nick has been with John Foster Real Estate since 1985. Prior to that, he owned and managed a successful sail loft and raced internationally.

Consistently one of the highest producers within the St Thomas Board of Realtors Multiple Listing system, Nick is committed to community involvement through service in local and Territorial Board of Realtors.  He is also an active member of Rotary International. Family is now Nick’s leisure priority with his wife, Joyce, a CPA, daughter Andi and son William.  International travel, sailing and sailboat racing are all activities the family enjoys together.

Nick's first hand knowledge of the Caribbean is merely one way he is able to assist his clients in finding the "perfect property". His goal is to assist his customers in finding their "Caribbean home" and making sure his clients are satisfied should they decide to sell their property in the Virgin Islands. He is more than willing to share his knowledge of island acquisitions and of island living. Nick is your Caribbean contact for real estate.

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