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Private Client · Invite Only

One Engagement.
Multiple Properties.
Fully Managed.

Acquire a portfolio of Sint Maarten properties across the island's best-positioned developments. Hold title directly. We operate everything — sourcing through stabilization through ongoing management — under one integrated platform.

Modern Sint Maarten resort property with ocean-facing balconies
Execution Lifecycle

Structured Execution

A defined execution sequence from structuring through operational stabilization. Not a sales pipeline — a controlled operational workflow.

Scope

Discovery & Engagement Structuring

amp; Deployment Structuring

We define the engagement scope: acquisition budget, target segments, ownership structure, operating strategy, and timeline. Nothing moves until the framework is agreed and formalized.

Sourcing

Sourcing & Diligence

amp; Underwriting

Curated inventory is evaluated against your engagement criteria. Every candidate undergoes title verification, structural assessment, zoning review, operational feasibility analysis, and building governance review before presentation.

Execution

Closing & Setup

amp; Stabilization

Title transfer, furnishing, licensing, insurance placement, and systems integration — coordinated through a single operational workflow. Your property is brought to full operational readiness before entering the management platform.

Platform Integration

Your asset enters the management platform: guest operations, preventative maintenance, vendor coordination, calendar optimization, and financial controls — all active from day one.

Oversight

Ongoing Stewardship

amp; Reporting

Monthly operating statements, expense controls, capital improvement tracking, calendar utilization reporting, and periodic strategic reviews. You retain full ownership and control. We execute operations under defined oversight parameters.

Clarity

What This Is

Leeward Acquisitions is an acquisition and management services company. We source, close, furnish, and operate residential properties in Sint Maarten on behalf of private clients who hold title directly.

We are not a fund, syndication, REIT, or pooled investment vehicle. We do not hold client assets, pool capital, or issue securities of any kind. Each engagement is a bilateral service agreement between the client and our firm.

We are not a licensed broker-dealer or investment advisor. We provide operational services — not investment advice.

Risk Factors

What You Should Know

Real property is illiquid. Caribbean markets carry specific risks including hurricane exposure, insurance cost variability, tourism cycle sensitivity, construction and permitting delays, and regulatory changes.

Operating performance depends on market conditions, guest demand, property condition, and management execution. Past results in this or any market are not indicative of future outcomes. We do not guarantee occupancy, revenue, appreciation, or exit pricing.

Prospective clients should conduct independent due diligence and consult qualified legal, tax, and financial advisors before engaging. Full disclosures →

The Market

Why Sint Maarten

US-dollar economy. No annual property tax. Direct flights from major US cities. Post-Irma construction built to modern hurricane-resistant standards. A finite island with structural supply constraints and sustained tourism demand.

Sint Maarten coastline and marina market setting
Engagement Scope

Typical Engagement Ranges

Each engagement is structured to your objectives. The figures below represent typical scope ranges. Portfolio composition — number, type, and segment of properties — is determined during structuring based on availability and operating strategy.

$2M
Foundation
  • Typically 1–3 properties
  • Studio to 2BR segments
  • Single development or mixed
  • Full management included
$10M+
Premier
  • Multi-segment portfolio
  • Potential standalone villas
  • Dedicated operations contact
  • Custom reporting cadence
  • Strategic advisory included

Sample economics and detailed engagement structures are available in the Private Deck after intake and NDA.

Asset Operations

Operational Modes

Each asset is operated under a defined strategy. The platform supports multiple modes simultaneously — calibrated to your objectives, risk tolerance, and market conditions.

Resort pool and guest-ready property operations setting

Short-Term

Revenue-optimized guest operations across distribution channels. Dynamic pricing, guest screening, concierge coordination, and quality-controlled turnover — managed through centralized oversight.

Mid-Term

Furnished monthly placements for extended-stay professionals and seasonal residents. Reduced operational intensity with predictable calendar utilization.

Long-Term

Annual lease placements with structured tenant screening, lease administration, and ongoing property preservation. Lowest operational overhead with stable occupancy.

Owner Integration

Owner Access

Your Property, Your Calendar

amp; Control

You hold title and retain full control over the asset. The engagement agreement defines how personal-use allocation integrates with the operating calendar — preserving flexibility without disrupting operational continuity.

Personal-use blocks are scheduled in advance according to the calendar governance terms established in your engagement. We handle pre-arrival preparation, provisioning, and post-stay reset — so your property is always ready.

House rules, guest policies, and maintenance standards are defined collaboratively and enforced consistently.

Reporting & Controls

  • Monthly operating statements
  • Expense transparency & approval thresholds
  • Occupancy & revenue reporting
  • Capital expenditure review process
  • Year-end summary package
  • Direct principal access
Local Advantage

Favorable Holding Environment

Sint Maarten currently does not impose annual property tax on residential real estate, based on current local practice. This is subject to change and should not be relied upon as permanent. Clients are encouraged to verify with qualified local counsel.

NDA available upon request. Delivered via email after intake. Detailed economics, sample pro formas, and development-level data are shared only under NDA.
Your Point of Contact

Led by Danielle Gaines

Fifteen years between Sint Maarten and Fort Lauderdale. Background in business operations, property acquisition, and asset management. Danielle is the direct point of contact for every client — from engagement structuring through ongoing operational oversight.

No sales team. No call center. One principal who knows your properties, your objectives, and the island.

Common Questions

Frequently Asked Questions

Leeward Acquisitions is led by Danielle Gaines, who has spent the past fifteen years between Sint Maarten and Fort Lauderdale building businesses and managing properties on-island. She is the direct point of contact for every client. There is no sales team — when you engage with Leeward Acquisitions, you work with Danielle and the operations team she has built locally. Learn more about our principal and approach.
You do. Clients take title directly — either in their personal name or in an entity they control (typically their own LLC). There is no pooled ownership, no fund structure, and no shared equity. You own the deed; we execute and manage under a clearly defined engagement.
An engagement is a defined service agreement between you and Leeward Acquisitions. It covers: acquisition criteria, operational strategy, reporting cadence, expense approval thresholds, owner-use scheduling, and exit coordination. It is a structured operating agreement — not a listing contract or investment offering.
Yes. Owner-use weeks are scheduled according to the calendar governance terms in your engagement. We handle pre-arrival preparation and post-stay reset. You simply arrive.
Potential lending pathways may be available through our lending affiliate or partners, subject to underwriting, collateral review, local legal considerations, and lender terms. Not all properties qualify. Details are discussed during the engagement structuring phase.
Sint Maarten currently does not impose annual property tax on residential real estate, based on current local practice. This is subject to change at any time and should not be relied upon as a permanent condition. We strongly recommend verification with qualified local counsel.
Sample economics, pro formas, and development-level data are available in the Private Deck, shared only after intake and NDA. Submit an inquiry below to begin the process.
We onboard a limited number of new engagements per quarter to ensure each client receives dedicated attention during the critical first 90 days of acquisition and operational setup. If current capacity is fully committed, we will let you know transparently and discuss timing for the next available window.
The Private Deck

What You'll Receive

After intake, qualified clients receive the Private Deck under NDA. Here's what's inside:

Market Data

Occupancy benchmarks, ADR ranges, seasonal demand patterns, and supply pipeline for Dutch-side developments.

Operating Models

Unit-level operating expense models, cost structures, and scenario analysis across different management strategies.

Fee Schedules

Management fee structure, acquisition coordination fees, setup cost ranges, and engagement agreement frameworks.

Development Profiles

Detailed profiles on available developments including unit mix, construction quality, HOA structure, and location analysis.

Governance Framework

Engagement agreement templates, reporting samples, expense approval thresholds, operational oversight parameters, and owner-use governance models.

Peer Comparisons

How SXM stacks against Turks & Caicos, Bahamas, Puerto Rico, and other Caribbean acquisition markets.

Get Started

Client Inquiry

Share your name and objectives. Danielle will respond personally, typically within one business day.

By submitting, you agree to our Privacy Policy. This is not a solicitation or offer. See Disclosures.

Prefer to skip the form? Email danielle@leewardacquisitions.com or WhatsApp +1 (721) 555-1234 directly.

Resources

Download the Overview

A summary of our engagement structure, management capabilities, and engagement process.

Download Overview (PDF)