The Honest Measure
Every market report, ours included, leans on medians across different houses. A repeat sale removes the mix problem entirely: the same walls, the same land, two prices. Across 84 such pairs on the island corridor since 2016, houses and condos together, the median annualized return is 17 percent, and only 5 pairs closed lower the second time. For comparison, the island's official median sale roughly quadrupled over the same decade. The repeat-sale record says that rise was real, not a trick of bigger and better houses selling later.
Timing Was Almost Everything
Split the pairs by when the first purchase happened and the decade's whole shape appears. Owners who bought between 2016 and 2019, before anyone was watching, resold at a median of 17 percent a year. Owners who bought in the frantic 2020 and 2021 window did even better, 25 percent a year, because they caught the repricing at its steepest. Owners who bought at the new prices, 2022 and later, have resold at a median of 8 percent a year, a normal luxury-market pace. The island repriced once. It has not needed to do it twice.
Source: BeachesMLS via Flexmls, repeat sales on the island corridor since 2016
Source: BeachesMLS via Flexmls. The public record does not show what owners spent in between
The Repeat-Sale Ledger
The ledger's top rows are condos near the inlet, modest purchases in 2020 and 2021 that doubled by 2022, the fastest repricing on the corridor. The houses climb more slowly in percentage terms and enormously in dollars. The estate pair everyone cites, $26M to $40M in under five years, is the record book's cleanest proof that the 2021 prices held and compounded. Several other pairs on the ledger carry a quiet asterisk. A gut renovation or rebuild sits between the two closings, and the public record cannot say how much of the gain was built rather than earned.
How to Read It Without Fooling Yourself
Three honest cautions. First, renovations are invisible here, so the top of the ledger overstates pure appreciation. Second, sellers choose when to sell, and owners sitting on losses often simply do not, which flatters every repeat-sale record. Third, the 2020 and 2021 cohort's 25 percent a year was a one-time repricing, not a run rate, and the 2022-and-later cohort's 8 percent is the sober trend. What survives all three cautions is the floor: 79 of 84 pairs resold higher across a decade, on an island whose supply cannot grow. That consistency, more than any single gain, is the record's real finding, and the record book shows where it tops out.
Bottom Line
Since 2016, 84 island properties have sold twice. The median pair gained 17 percent a year, 79 of 84 resold higher, and the gains ran steepest for owners who bought before the 2021 repricing. Since 2022 the pace has settled to a normal luxury market's.
For anyone weighing the island as a hold: Trust the pairs, respect the cautions, and buy the island for the land and the life. The appreciation record is the byproduct, not the promise.
A repeat sale here is the same street address, with the unit where applicable, closing twice in the deduplicated MLS record. The window is January 2016 through August 2026, with at least nine months between the closings. Annualized gain is the compound rate between the two closed prices. Renovation and construction between sales are invisible to the record, so no adjustment is made. Sales below two million dollars are included in every statistic but omitted from the example table.
This report describes realized past results on specific properties. It is not a projection and not investment advice. No owner is named.
BeachesMLS via Flexmls, the island corridor, 2016 through August 2026.
