Most Hamptons purchases are second homes — which changes the financing, insurance, structure, and strategy. Here's how to get each one right.
Plan Your PurchaseThe Hamptons is fundamentally a second-home market — the majority of buyers Luke represents are acquiring a weekend and summer residence to complement a primary home in Manhattan, Brooklyn, or beyond. That changes the purchase in ways first-home instincts miss: lenders underwrite differently, insurers price differently, taxes treat the property differently, and the right house is defined by how you'll actually use it — which weekends, which months, how many guests, and how much upkeep you want to own.
Second-home mortgages typically require larger down payments and carry modestly higher rates than primary-residence loans, and lenders draw a sharp line between "second home" and "investment property" classification — plan to rent significantly and the underwriting changes. Many Hamptons buyers at higher price points use securities-based lines or cash with delayed financing instead. Luke coordinates with private bankers who know East End collateral, and walks through the mechanics in the Hamptons Home Buying Guide.
Coastal insurance deserves early attention: wind deductibles, flood positioning (see the waterfront buying guide if you're near water), and unoccupied-home provisions all affect cost and claims. Many buyers take title through an LLC or trust for liability and privacy — a decision to make with counsel before contract, not after. And budget the carry honestly: property taxes (mercifully moderate by New York standards), closing costs including the Peconic Bay transfer tax, insurance, and the landscaping-pool-caretaking stack that keeps a Hamptons house ready for Friday arrival.
Many second-home owners rent for part of the season — August alone can carry a meaningful share of annual costs. But Hamptons rentals are regulated: rental registries, permit requirements, and minimum-stay rules vary by town and village. If offset income is part of your math, read Hamptons investment properties and buy in a community whose rules fit the plan.
Luke Cawley helps second-home buyers define the use case first, then match it to community, property, and structure — including off-market inventory. Start with how you want your summers to feel; Luke will handle the rest.
Tell Luke how you'll actually use the house — he'll match the community, the property, and the structure to it.
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