Company Overview

$5B
Sold in Anguilla & Caribbean
$100M+
Closed in Anguilla by Each Principal Individually
$10B
Financed in Anguilla, Caribbean & US
100
Anguilla Villa & Condo Closings
4 of 5
of Anguilla's Luxury Resorts Sold or Financed
45
Years in Real Estate
1
Who We Are
2
Why Work With Us
3
How We Are Different
4
Markets We've Served
5
Where We Live
6
How We Help Buyers
7
How We Help Sellers & Developers

Who We Are

Anguilla's Most Experienced Real Estate Team

Trophy Properties Caribbean is Anguilla’s go-to team for both real estate and vacation rentals. We’ve closed over $5 billion in real estate sales in Anguilla and the wider Caribbean. We also market, rent and manage many of the island’s most sought-after vacation homes.

We take care of the big picture and the fine details. With our global network, deep local knowledge and hands-on approach, we guide you through every step of your Anguilla real estate journey.

Whether you’re a family searching for your dream island home, a developer planning a new project or an investor looking for a high-performing vacation rental or resort property, we’re here as your single point of contact — from finding the perfect site to move-in day, and even ongoing management.

Why Work With Us

A Track Record of Trust

We help clients buy and sell villas, land, condominiums, commercial property and resorts of all sizes and price ranges. Our sales include iconic resorts Four Seasons Anguilla, Zemi Beach House and Aurora Anguilla Resort & Golf Club (formerly Cuisinart).

We are also the exclusive broker for Four Seasons Anguilla residence resales and Tranquility Beach Resort condominium sales.

Beyond just real estate sales, we’ve secured over $10 billion in financing for U.S. and Caribbean properties, plus Anguilla’s Malliouhana and Zemi Beach hotels, and the development of Villa Alegria, Long Bay Villas, Santosha Villa Estate and Tranquility Beach Anguilla Resort.

With decades of combined experience in real estate sales, financing, development, and rentals, plus strong institutional and private equity relationships, we know how to move deals forward and maximize value for you.

How We Are Different

Comprehensive Expertise, All Under One Roof

Trophy Properties Caribbean was founded by top Anguilla broker Steve Haines of company predecessor Trophy Properties Anguilla Ltd., leading Caribbean hospitality broker Paul Weimer, and expert financier and Tranquility Beach co-developer Neil Freeman. They’re joined by skilled broker Lisa DeLong and rental management specialist Leana Harris.

Based in Anguilla, our international team offers unmatched access, insight, and personal service for buying, selling, developing or renting residential, resort, commercial properties and land across the Caribbean.

We’ve sat on all sides of the table as brokers, buyers, sellers, developers, financiers, renters and managers. This 360° view combined with our experience and proven results, is why we’re trusted to represent Anguilla’s most prestigious properties.

Our clients come back to us because we listen, share local-level insight, and use a transparent, data-driven approach to create strategies that truly fit their goals.

Markets We've Served

Local Knowledge With Global Reach

While we’re based in Anguilla, our work extends across the United States and beyond, connecting us with investors, travelers, luxury brands, developers, referral partners, vacation rental agencies and capital sources worldwide. This combination of deep local roots and global reach gives our clients a powerful advantage.

Where We Live

Invested in Anguilla's Future

Trophy Properties Caribbean is headquartered in Anguilla. We live here, work here, and some of us 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. 

How We Help Buyers

Expertise from Start to Close and Beyond

Trophy Properties Caribbean provide buyers with:

Personalized property matches based on your wish list and needs.

Insider access to off-market, pre-launch, and exclusive listings.

Seamless transaction support from due diligence and permitting to financing.

Ongoing care after closing, with help finding designers, managing your property, and marketing rentals.

How We Help Sellers & Developers

Full-Service Expertise & First-Hand Experience

Trophy Properties Caribbean provides sellers and developers with:

Smart valuation and pricing guidance to position your property for success.

Targeted global marketing and exclusive VIP broker tours.

Expert negotiation to secure the best price and terms.

Pre-sale programs tailored for new developments and fractional ownership opportunities.

 

Meet The Team

Guide to Buying Anguilla Real Estate

Example Closed Sales

Client Reviews

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  • “Buying a condo at Tranquility Beach Anguilla was the perfect choice for us — and Lisa DeLong made the entire process seamless. She knew the ins and outs of the property, explained the rental potential clearly, and connected us with all the right people. Now we have a beautiful place in Anguilla that practically pays for itself when we’re not using it!”
    — Bonner Family, Purchased Resort Condominium
  • Thank you Trophy Team you guys were so helpful and professional in helping me find my dream home in paradise on the island of Anguilla. I will stay in touch during my time on the island and again, thank you!
    — Dave, Purchased Home
  • “Lisa made the whole process so easy. From our first conversation to the final Closing, she guided us through every step of buying our 5-bedroom oceanfront villa in Anguilla with professionalism, warmth, and deep local knowledge. She handled everything with care, patience, and honesty. We trusted her completely — and we’re so glad we did.”
    — Jones Family, Purchased Villa
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Contact Details

Trophy Properties Caribbean

Phone

+1 (264) 476-4321

Email

[email protected]

Email

[email protected]

Address

South Hill Plaza Anguilla BWI AI2640

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