307B Jolly Harbour, St Mary's, Antigua, WI

Sint Maarten's property market data tells a story in two parts: a listings-based price picture that shows a properly liquid, moderately-priced market overall, and a rental performance picture, at least for one of its most established neighbourhoods, that shows real income potential for well-positioned properties specifically.
As of May 2026, the median asking price for an apartment on the island sits at $490 per square foot, with houses running slightly lower at $447 per square foot, based on currently active listings. These figures reflect what sellers are asking rather than confirmed completed transaction prices, so they are best read as a general positioning indicator for the market rather than a precise average of what buyers are actually paying, a distinction worth keeping in mind before treating either figure as a firm benchmark for a specific negotiation.
Current luxury development activity concentrates in a handful of corridors: Cupecoy, described by a long-established local agency as the island's leading corridor for upscale condominium development, alongside Mullet Bay, Indigo Bay, Simpson Bay and Pointe Blanche. Simpson Bay in particular continues to draw strong interest for waterfront condos and luxury residences specifically because of its marina lifestyle, dining scene and consistent year-round rental demand, a combination that keeps it active even as newer corridors like Cupecoy attract more of the newest supply.
Simpson Bay offers some of the more detailed, independently-verified short-term rental data available anywhere in this series. Across the twelve months to July 2026, active Simpson Bay listings on AirROI's tracked data averaged US$56,287 in annual host revenue, at an average nightly rate of $449 and a Revenue Per Available Room (RevPAR) of $212, with average occupancy at 47.4% across 106 active listings. These figures describe the typical revenue environment for active listings, not the ceiling the best-performing, best-positioned properties can reach, and Simpson Bay itself is described as a boutique market, meaning a well-differentiated listing has genuine room to outperform the average shown here.
Available data on Simpson Bay's short-term rental sector points to low regulation and minimal formal registration activity, with one analytics provider finding no licensed listings among those it analysed, a markedly different regulatory posture from the licence-and-tax systems covered elsewhere in this series for the US Virgin Islands or Antigua. This does not mean no rules exist, and anyone entering the short-term rental market should still verify current requirements directly with local government authorities before hosting, since a light current regulatory footprint is not the same as a guarantee that the situation will stay that way.
Separately from the general condo and villa market described above, Terres Basses on the French side represents a wholly distinct, scarcity-driven segment, where homes rarely trade as casual purchases and pricing depends heavily on factors beyond simple size and bedroom count, view quality, beach access and specific legal jurisdiction among them. This segment does not move in line with the broader Sint Maarten market described above, and comparing a Terres Basses villa directly against Cupecoy or Simpson Bay condo pricing on a straightforward price-per-square-foot basis would understate how differently that top tier of the market actually behaves.
Sint Maarten in 2026 offers a market with real transparency at the general listings level and, in Simpson Bay specifically, some of the better-documented short-term rental performance data available in this series. This supports the case made elsewhere in this series for the island's open property market and lighter tax structure: genuine liquidity in the mid-market, concentrated new development in a handful of well-identified corridors, and a scarcity-priced luxury segment that plays by its own rules entirely.

Investment Strategies

Investment Strategies

Investment Strategies
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