My office sits inside the Four Seasons Resort on Nevis, so take the conflict first rather than find it in the footnotes: I sell one of these two properties and have no listings at the other. What makes the question answerable is that the brand is held constant — same operator, same standard, two islands. Strip the flag out and what remains is the real decision: price, carrying cost, and what you may do with the unit once you own it.
The short answer
For most buyers weighing the two, I land on Four Seasons Nevis — and not out of loyalty. A four-bedroom beachfront villa at Four Seasons Anguilla is listed at US$7,950,000 for 403 square metres: roughly US$1,830 a square foot on my own arithmetic. A whole beachfront villa at the Villas at Pinney's Beach on Nevis is US$4,150,000 for 365 square metres, roughly US$1,055. That is about 1.7 times the price per square foot and nearly twice the cheque for the same flag over the door. My read across branded units in the two markets is a premium of roughly 1.5 to 2 times, and the one directly comparable pair I can cite sits inside that band. Anguilla earns part of it — better beach, newer buildings, everything finished rather than rendered — but not all of it, once the annual assessment enters the model. Buy Anguilla anyway if the sand and the water are the asset, if you refuse to sign for anything unbuilt, and if a second passport plays no part in your thinking. Otherwise Nevis is the better-priced version of the same idea, with a citizenship option Anguilla cannot offer at any price.
Two properties, one flag, almost nothing else in common
Four Seasons Resort Nevis has run under the flag since February 1991 — the brand's first Caribbean property — on roughly 350 acres of former sugar plantation running from the lower slopes of Nevis Peak down to Pinney's Beach, with an 18-hole Robert Trent Jones II course threaded through it and privately owned villas across the fairways. It is a resort you drive around, and at thirty-five it is a legacy property being rebuilt around its own edges.
Four Seasons Anguilla is the opposite on every axis: a rocky point at the island's west end, Barnes Bay on one side and Meads Bay on the other, across roughly 35 acres — a tenth of the Nevis footprint. It did not open as a Four Seasons. The brand took over management in October 2016 of a resort built under a different flag, and it runs today as 181 accommodations: 70 guest rooms, 50 suites, 24 villas, 4 townhomes and 33 residences. Density is not a criticism — Anguilla's compactness is why the service feels tight and the finishes current, while Nevis's sprawl is why a family of nine can take a villa with its own pool and never see another guest.
The case for Anguilla, made properly
The beach and the water are better. Not close, and I will not pretend otherwise. Anguilla is a low coral island with 33 beaches and no cruise terminal, no casinos and no high-rises, and the west end holds arguably the finest run of white sand in the region. Pinney's is a good beach on a volcanic island; Meads Bay is a great beach on a sand island.
Everything is built. You can sleep in the unit you are considering before you wire a dollar — a real advantage in a region where much of what is sold to overseas buyers exists only as a rendering. The resort also passed to a single, well-capitalised investment and development group in July 2022, which is the best available structure for an asset whose brand, amenities, rental engine and homeowners' association all sit with one counterparty.
There is a scene. The dining, the beach bars and the resident international community give the island a social life Nevis does not attempt, and the feel is more formal, more dressed. That is my read rather than a statistic, but a consistent one across a lot of client trips, and for some families it decides the question outright.
And there is no program entanglement. Freehold, no seven-year hold, no approved-development list, no government policy between you and your buyer. Anguilla levies no personal income tax, no capital gains tax and no inheritance tax — standing policy, not a promotional scheme — and the High Value Resident route offers tax residency for a flat annual worldwide-income payment of US$75,000 against property worth at least US$400,000. A separate residence-by-investment route from US$750,000 opens a pathway to British Overseas Territory Citizenship after five years of lawful residency, which no Caribbean citizenship program replicates.
One correction before anyone gets excited. If you are American — and about 95% of my clients are — none of that tax architecture does what the brochure implies. The United States taxes citizens and green-card holders on worldwide income wherever they live, whatever else they hold. An Anguillian tax residency sits alongside your US filing obligations, not instead of them.
What the price difference actually is
The one named Four Seasons Anguilla listing I can cite is a four-bedroom beachfront villa of 403 square metres — about 4,340 square feet — at US$7,950,000, or roughly US$1,830 a square foot. The closest structural comparable on Nevis is a whole beachfront villa at the Villas at Pinney's Beach, 365 square metres or about 3,930 square feet, at US$4,150,000 — roughly US$1,055.
Widen it to branded Four Seasons Nevis inventory and the band runs from about US$1,030 a square foot at Nevis Peak Residences, where a one-bedroom of 135 square metres is listed at US$1,499,000, up to about US$1,425 at Ouje Mango Rif House, a 570-square-metre estate home at US$8,750,000. Mahogany Hill, a 295-square-metre hillside villa at US$4,250,000, sits near US$1,340. Against that band the Anguilla villa prices at about 1.3 times the top and 1.8 times the bottom.
Two qualifications. Those per-square-foot figures are my own division of asking price by stated interior area, and area conventions vary between developments — a band, not a valuation. And one Anguilla comparable is a data point, not a market; what I can add is that the multiple I see across branded units sits consistently in the 1.5 to 2 range.
The gap is wider at the entry. A deeded one-tenth fractional interest in a Four Seasons villa on Nevis is listed at US$325,000, carrying five weeks a year; a one-sixth carries eight. Nothing at Four Seasons Anguilla is sold in fractions, and the cheapest whole-ownership figures I have seen there are a 662 sq ft studio at US$700,000 and a 991 sq ft one-bedroom at US$1,025,000.
The carrying cost is where the gap stops being arguable
The Four Seasons Anguilla residences' own rental-program FAQ puts the annual Homeowner Assessment Fee at approximately US$33 per interior square foot per year. Against the published unit sizes that stops being abstract: roughly US$76,000 a year on a 2,300 sq ft two-bedroom, close to US$118,000 on a 3,567 sq ft penthouse. It is fixed whether you visit or not.
In fairness, it is not pure overhead. The association pays, on the owner's behalf, all utilities, taxes, property, casualty and liability insurance including hurricane cover, common-area maintenance, amenity access and telecom. Against running a standalone villa, the gap narrows considerably.
Set it beside Nevis anyway. Full club membership on a one-tenth fractional share, including unlimited golf and tennis, is quoted at US$2,610 a year; US$4,350 on a one-sixth. The assessment on one Anguilla two-bedroom is more than twenty-five years of those dues. They are not equivalent products and the Nevis figure covers far less — which is why I tell whole-ownership buyers on Nevis to demand a dues schedule with three years of actuals and every special assessment before exchange. The estate publishes none, and that is a genuine weakness on my side of the argument.
The rental terms deserve equal scrutiny. Participation at Anguilla is optional — not true of every branded residence in the region — and it is not a pool: you are paid on what your own unit earns. But the split reads 50% of the net rental income, after 12.75% of the gross goes to the resort as a service charge, with a further 5% of your rental income into a furniture reserve. Most units cap owner usage at 90 days a year, of which up to 60 may fall in high season — if the plan is a Caribbean winter in your own house, that plan and that program are in tension. Nevis fractions are simpler, five or eight defined weeks in the deed rather than at anyone's discretion, while Nevis whole-ownership rental economics are not published at all, which is its own problem.
The comparison, side by side
| Four Seasons Nevis | Four Seasons Anguilla | |
|---|---|---|
| Site | ~350 acres, Pinney's Beach to the slopes of Nevis Peak | ~35 acres on a point between Barnes Bay and Meads Bay |
| Feel | Low-density estate, golf, separate villas | Compact, modern, higher density, more formal |
| Entry ticket | Deeded 1/10 fractional from US$325,000, five weeks a year | Whole ownership only; no fractions |
| Implied US$/sq ft, branded | ~1,030–1,425 across current listings | ~1,830 on the one named villa listing |
| Named villa comparable | Beachfront villa, Pinney's Beach, 365 m², US$4,150,000 | Four-bed beachfront villa, 403 m², US$7,950,000 |
| Annual fixed cost | Fractional dues US$2,610 (1/10) / US$4,350 (1/6); whole-ownership dues unpublished | HOA ~US$33 per interior sq ft — about US$76,000 on a 2,300 sq ft two-bed |
| Owner use if you rent | Five or eight defined weeks on a fraction | Most units capped at 90 days a year, 60 in high season |
| Citizenship | Yes — from US$325,000, seven-year hold, 155 destinations | None at any price; residency only |
| Foreign-buyer licence | ~10% — not required on an approved CBI purchase | Required; published rates conflict |
| Golf | 18-hole Robert Trent Jones II course on the estate | None on site |
| Final leg | Fly to St Kitts, then ferry or water taxi | Fly to St Maarten, then ferry or short hop |
| Suits | Citizenship, space, golf, a lower entry, a market with capital arriving | Buyers for whom the beach is the asset, who want finished product and will use it lightly |
| Does not suit | Anyone refusing construction risk, or who wants the region's best sand | Americans expecting a tax outcome, winter-long users, the price-sensitive |
What Nevis is buying you that Anguilla cannot
A passport, if you want one. Four Seasons Resort Estates appears on the government's approved-developments list. The minimum qualifying investment is US$325,000 for a condominium unit or a share in a designated development, and US$600,000 for a single-family home designated as approved private real estate, with a seven-year hold before resale. The passport carries visa-free or visa-on-arrival access to 155 destinations. Approval attaches to specific units rather than the estate's postcode, so get written confirmation from the Citizenship by Investment Unit before a deposit moves.
A six-figure saving at closing. A non-citizen buying an ordinary Nevis property needs an Alien Landholding Licence at about 10% of value; a purchase inside an approved citizenship development does not. On a US$1.5 million house that is US$150,000. Anguilla has no equivalent exemption, and its published rates disagree — government guidance notes dated April 2004 put stamp duty on the licence at 12.5% of freehold value plus 5% on the transfer, while the residences' own rental FAQ refers to an 11.5% fee waived for buyers who join the rental program. Budget off neither without written confirmation from an Anguillian attorney.
A market with capital arriving rather than one already priced. Nevis Peak Residences is 58 new-build one-, two- and three-bedroom homes from 1,725 to 3,730 square feet across six low-rise buildings along the 7th and 8th fairways, with my brokerage as exclusive sales agent — declare that too. The island broke ground on 1 July 2026 on an airport expansion extending the runway toward roughly 6,000 feet from about 4,000. Neither makes a market alone, but they are the shape of an island in transformation, and the wider Nevis market beyond the resort gates still trades at a fraction of the branded band: unbranded condominium stock on the same coast runs roughly US$435 to US$565 a square foot.
The risks on my own side of the argument
Nevis is a 1991 property mid-renovation, and part of what you are shown is a rendering. Nevis Peak was announced as welcoming homeowners in 2025 and I have found no independent confirmation of handover; every image in circulation is a rendering rather than a photograph. Confirm the completion status of your building, the deposit schedule, and what protects your money if handover slips. Anguilla's answer is simply better: it is standing, and you can walk it.
The resort has gone dark before, for a long time. Hurricane Omar closed it in October 2008 and it reopened in mid-December 2010 — two years and two months — after roughly US$120 million of spending, US$80 million of it reconstruction. Underwrite a closure, not just a storm. The counterpoint is that an institutional owner absorbed it and rebuilt; the resort is owned by Bill and Melinda Gates Investments. Anguilla sits in the same hurricane belt on a low coral island, with hurricane cover inside the assessment — confirm the limits and the deductible, not just that cover exists.
Nevis's land tax is asymmetric. Residential land is taxed at 0.75% and residential buildings at 0.156% of assessed value, due annually by 30 June — so on a large lot with a modest house, the land line dominates.
Program risk prices your exit. The seven-year hold means your resale window opens under rules that may look nothing like today's, and a property that has already carried one citizenship application generally cannot support another without substantial further investment — so your exit buyer is usually not the next applicant. The IMF's 2025 Article IV consultation found St Kitts & Nevis CBI revenue had fallen to roughly 8% of GDP in 2024, from about 22% the year before.
Anguilla's own exit is slower still, and its paperwork is looser. The resort's two published price lists carry a near-identical two-bedroom at US$3,725,000 on one and US$2,457,056 on the other, so work from a dated written offer and never a portal page. Its history belongs here too: the original developer filed for Chapter 11 in Delaware in 2011, the property sold at auction that July to its lender's affiliate as the only bidder, and purchasers who had paid deposits in that era had to litigate to recover money. None of that describes today's asset — built, operating, consolidated under one owner — but it should shape how you handle deposits, escrow and title.
Where I land
If a client tells me the beach is the point — that they are buying water, will use the house lightly, will not sign for anything unbuilt, and have no interest in a second citizenship — I tell them to buy Anguilla and I mean it. They should go in knowing the assessment is a serious permanent number, the rental program will cap their winter, and the exit is slow.
For everyone else, and that is most of the people who ask me, Nevis is the better-priced version of the same brand promise. Roughly 1.7 times the price per square foot is a great deal of money for a beach upgrade and a livelier evening, asked on top of a heavier carrying-cost structure. What Nevis gives back is a citizenship option Anguilla cannot offer at any price, an entry point at US$325,000 rather than seven figures, an exemption from a licence fee that would otherwise cost six figures, a golf course, ten times the land, and a market mid-change rather than at the end of one.
Underwrite either as a place you want to own for twenty years, and treat rental income as an offset to carrying cost rather than a return. If you want the real numbers on whichever you are leaning toward, my door at the resort is open.
Key takeaways
- On the one comparable pair I can cite, Four Seasons Anguilla prices at roughly US$1,830 a square foot against roughly US$1,055 for a whole beachfront villa at the Villas at Pinney's Beach — about 1.7 times per square foot, 1.9 times on the cheque.
- Anguilla's homeowner assessment runs at approximately US$33 per interior square foot, roughly US$76,000 a year on a 2,300 sq ft two-bedroom — fixed whether you visit or not, though it covers utilities, taxes and hurricane insurance.
- Nevis offers a deeded one-tenth fractional from US$325,000 with five weeks a year; Anguilla sells whole ownership only, and most units in its rental program cap owner use at 90 days.
- Only Nevis carries citizenship — from US$325,000 under a seven-year hold, with 155 visa-free or visa-on-arrival destinations — and a CBI-approved purchase skips the roughly 10% Alien Landholding Licence entirely.
- Anguilla wins on beach, condition and the fact that everything is built; Nevis wins on price, entry ladder, land and golf. For Americans, neither changes US worldwide taxation.
Frequently asked questions
Is Four Seasons Anguilla really twice the price of Four Seasons Nevis? Close to it on a whole villa: US$7,950,000 for 403 square metres in Anguilla against US$4,150,000 for 365 square metres at the Villas at Pinney's Beach on Nevis — 1.9 times the cheque, about 1.7 times per square foot. My read across branded units in the two markets is a premium of roughly 1.5 to 2 times, and that pair sits inside it.
Can I get a passport by buying at Four Seasons Anguilla? No. Anguilla is a British Overseas Territory and runs no citizenship-by-investment program at any price. It offers residency: a High Value Resident tax route at a flat US$75,000 a year against property worth at least US$400,000 and 45 non-consecutive days on the island, and a residence-by-investment route from US$750,000 covering up to four family members, with a pathway to British Overseas Territory Citizenship after five years of lawful residency. Four Seasons Nevis sits on the St Kitts & Nevis approved list at a US$325,000 minimum with a seven-year hold.
Which one is easier to sell later? Neither is liquid, and both need patience. Anguilla is thinner — one recent review tracked 22 active island-wide listings through a single international brokerage, and your buyer must clear an Alien Land Holding Licence. Nevis carries a seven-year hold, and a unit that has already supported one citizenship application generally cannot support another, so your buyer is usually someone who simply wants the real estate.
Which one is the better rental investment? Neither should be underwritten as a yield play. Anguilla's program is optional and pays you on your own unit's earnings, but the split is 50% of net after 12.75% of gross goes to the resort, plus 5% into a furniture reserve, and most units cap owner use at 90 days a year. Nevis fractions give five or eight defined weeks, while whole-ownership rental economics there are not published at all. Ask for two years of actual owner statements on the specific unit.
I am American. Does buying in Anguilla cut my tax bill? No. The United States taxes its citizens and green-card holders on worldwide income regardless of where they live or what other residency they hold, and no Caribbean passport or residency changes that. An Anguillian tax residency sits alongside your US filing obligations, not instead of them. Take US tax advice before you buy, not after.
