Hamptons Market Guide
Local replacement-property planning and deadline coordination for investment owners in Amagansett.
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Montauk 1031 exchange planning for owners of motels, fishing-related, and seasonal hospitality property at the eastern tip.
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Wainscott 1031 exchange support built around the hamlet's single commercial-industrial zone, where turnover is real but rare.
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Water Mill 1031 exchange planning that separates the hamlet's visible Montauk Highway retail from what actually qualifies as stabilized income.
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Sagaponack 1031 exchange planning for the smallest incorporated village on the South Fork, where farmland easements limit what qualifies as.
ExploreMost 1031 pitches aimed at Amagansett sellers treat the hamlet as generic Hamptons acreage. It is not. Amagansett is a narrow strip between the ocean and Napeague Bay with a handful of retail blocks and very little else zoned for commercial use, and that shortage changes how a START EXCHANGE REVIEW actually has to run.
The relinquished property in an Amagansett exchange is rarely a large asset. It is more often a small mixed-use building near Main Street or Indian Wells Highway, a seasonal rental package, or a family-held lot that finally sold after decades. The gain can still be large even when the building is modest, because land near the ocean here carries pricing that has little to do with square footage.
That mismatch between building size and tax exposure is where a lot of exchange planning goes wrong. A seller who assumes a small building means a small problem can end up underestimating the identification work required.
An identification list built without local knowledge tends to miss what actually functions as commercial ground here.
Everything on that list is small by acreage but expensive by the foot, and none of it trades often enough to assume a backup option will appear on short notice.
Because Amagansett itself rarely offers three genuinely distinct commercial candidates at once, sellers who want to stay local usually end up leaning on the 200% rule instead of the standard three-property list, naming more properties by count but staying under 200% of the relinquished value in total. That approach only holds up if the value math is checked against real asking prices, not optimistic ones.
The 45-day identification window does not stretch for a thin market. Sellers who wait to see what comes on the market lose weeks they cannot get back, and a qualified intermediary cannot extend that clock for anyone.
A lot of DST wholesaler decks that get emailed to Amagansett sellers show diversified portfolios and skip the sponsor load, the hold period, and the fact that the investor gives up control entirely. That is not a reason to avoid a DST when local inventory is this thin, but it is a reason to ask what the total fee drag looks like before signing anything, and to get that answer in writing rather than in a slide.
Because relinquished proceeds have to sit with the qualified intermediary and never touch the seller's account, constructive receipt is the detail that trips up first-time Amagansett exchangers most often, usually through a title company mix-up rather than intent. Boot exposure shows up when a seller trades down in either price or debt, so the replacement side needs a debt and value target before the 45 days start running, not after.
A one-page engagement letter that just says exchange coordination for Amagansett is not a scope of work, it is a placeholder. A seller should expect the letter to name who is responsible for confirming replacement value against actual comparable sales, not asking prices, whether the sourcing party will flag DST sponsor fees before recommending an allocation, and who signs off on the boot calculation before the identification list is filed. None of that is unusual to ask for, and any broker or coordinator who treats the question as an imposition is telling the seller something about how the rest of the engagement will go. Amagansett's thin inventory makes this more important than it would be in a market with backup options on every block, because there is often no time to switch advisors mid-search if the first engagement letter turns out to be vague about who does what.
Commercial-zoned parcels in Amagansett are limited to a few small clusters, so sellers who want local START EXCHANGE REVIEW often name several candidates and rely on the 200% rule to stay compliant rather than a clean three-property list.
Yes, a Delaware Statutory Trust interest qualifies as like-kind real property, and it is a common fallback when a thin local market makes finding enough qualifying replacement property difficult within 45 days.
Boot usually appears when the replacement property carries less debt or a lower price than the relinquished property, or when any cash is taken at closing instead of being reinvested through the exchange.
Yes, the intermediary holds and controls the proceeds between closings; the seller cannot take receipt of the funds at any point without breaking the exchange.
Given how few active listings exist locally at any time, most advisors recommend lining up a tax advisor and qualified intermediary well before the relinquished property goes under contract, not after.
It should name the fee schedule, the deadline for delivering exchange documents, and confirm in writing that the intermediary will not release funds to anyone but escrow or the replacement closing.
That confirmation should come from the seller's broker or appraiser using actual comparable sales, not the qualified intermediary, whose role is limited to escrow and documentation.