Company Overview

Trophy Properties Caribbean is Anguilla’s premier, full-service real estate brokerage and vacation rental agency with over $3.3 billion in closed real estate sales across Anguilla, the Caribbean and United States. We market, rent and manage many of Anguilla's most successful vacation rental properties.

Using our comprehensive approach, global network and market mastery, we help you manage every facet of your Anguilla real estate transaction. 

Whether you are a family looking to buy your island dream home, or a developer or investor seeking an income-producing vacation rental property, larger land or resort acquisition, or master planning, Trophy Properties Caribbean is your single-point of accountability from choosing a site to move-in to management.

Sold Anguilla's most iconic luxury villas and 5-star resort properties:

• Four Seasons Anguilla, Zemi Beach House and Aurora Anguilla Resort & Golf Club (formerly Cuisinart)
• Altamer, Beaches Edge, Zebra Villa and other private villas
• Condominiums at Tranquility Beach Resort on Meads Bay Beach

Exclusive broker for Four Seasons Anguilla residence resales and Tranquility Beach Resort condominium sales. Closed Anguilla's largest single-family-home transaction.

Secured over $10 billion in financing for properties across the US and Caribbean including the world-ranked Waldorf Astoria hotel, The Roosevelt Hotel New Orleans and Anguilla’s Malliouhana and Zemi Beach hotels, as well as the development of Anguilla’s Villa Alegria, Long Bay Villas, Santosha Villa Estate and Tranquility Beach Resort.

Hold 15 to 45 years of individual experience in real estate sales, financing, development and rentals, including specialized expertise in cultivating institutional and private equity relationships that will help you accelerate deal flow and maximize value.

Trophy Properties Caribbean was founded by top-producing Anguilla real estate broker Steve Haines (who helmed Trophy Properties Caribbean’s predecessor, Trophy Properties Ltd.); the Caribbean’s leading hospitality real estate broker, Paul Weimer; and expert financier, Tranquility Beach co-developer and Aries Capital founder, Neil Freeman. Also at your service are skilled broker, Lisa DeLong and rental management specialist, Leanna Harris.

Our Anguilla-based international team provides unmatched access, insight, and personalized service for buying, selling, developing, or renting residential, resort, commercial properties, and land in Anguilla and the Caribbean.

We’ve sat on every side of the deal — as real estate brokers, buyers, sellers, developers, financiers, renters and managers. This broad perspective, along with our proven track record, has made us the trusted representatives for selling Anguilla’s most prestigious properties.

Our clients return to us because we listen and use our neighborhood-level insight and transparent, data-driven pricing to effectively execute strategies tailored to your life goals.

Our Anguilla-based team also works within the United States, giving us powerful connections with investors, luxury brands, developers, referral partners, vacation rental agencies and capital sources around the world. This unique blend of local roots and international reach gives you a strategic edge.

Trophy Properties Caribbean is headquartered in Anguilla. We live here, work here, and even raise our families here—and we’ve personally bought, sold, rented, and developed our own properties on the island. With real skin in the game, our team knows exactly how to navigate the Anguilla real estate landscape and deliver results for you. We've been in your shoes.

Curated property matching based on your detailed needs analysis.

Access to off-market and pre-launch real estate opportunities and our exclusive listings.

Full transaction coordination, including due diligence, permitting and financing.

Support after you close, including interior design referrals, property management and rental marketing.

Strategic valuation and pricing advice.

Targeted global marketing campaigns and VIP broker tours.

Skilled negotiation to maximize sale price and ensure favorable terms.

Pre-sale programs for new developments and fractional offerings.