Exchange Into the Lakes Region

Named after Section 1031 of the Internal Revenue Code, a 1031 exchange (also called a "like-kind exchange" or "Starker exchange") allows you to sell an investment or business-use property and defer all capital gains taxes by reinvesting the proceeds into another qualifying property. The tax isn’t eliminated — it’s deferred until you eventually sell without exchanging. Many investors chain 1031s for decades, deferring gains across multiple properties.

The definition is broader than most people expect. Any real property held for investment or business use can be exchanged for any other real property held for the same purpose. An apartment building in Boston can be exchanged for raw land in Moultonborough, a commercial storefront in Wolfeboro, or a waterfront vacation rental on Winnipesaukee — as long as both properties are held for investment or business use (not as a primary residence).

There are two strict, non-extendable deadlines once you close on the sale of your relinquished property. 45 days — you must identify up to three potential replacement properties in writing to your Qualified Intermediary. 180 days — you must close on one or more of those identified properties. No extensions, even if the 180th day falls on a holiday.

Yes — this is one of the most popular 1031 strategies in the Lakes Region. A lakefront property rented out on a weekly basis qualifies as investment property. The key is that the replacement property must be held primarily for investment or rental income, not primarily for personal use. You can use the property yourself for a limited number of days per year (the IRS safe harbor is 14 days or 10% of the days it’s rented, whichever is greater), but the primary purpose must be rental income.

Yes. The IRS requires that a Qualified Intermediary (QI) hold the proceeds from the sale. You cannot touch the money at any point during the exchange — if the funds pass through your hands or your agent’s, the exchange is disqualified. The QI must be set up before you close on the sale of your current property. Your real estate attorney, CPA, or our office can refer you to established QIs who handle Lakes Region transactions regularly.

Eventually, yes — but not right away. The IRS expects you to hold the replacement property for investment use for a reasonable period (most tax advisors recommend at least two years of active rental). After that holding period, you may convert it to a primary residence. If you live in it for 2 of the 5 years before a future sale, you may also qualify for the Section 121 capital gains exclusion ($250K single / $500K married). This "1031-to-121" strategy is a legitimate way for people to eventually retire to the lake.

New Hampshire has no state income tax on wages or rental income, no sales tax, and no capital gains tax at the state level. That means a 1031 exchange into NH real estate only needs to satisfy federal requirements — there’s no additional state-level recapture to worry about. For investors exchanging out of high-tax states like Massachusetts, Connecticut, or New York, this can mean significant additional savings beyond the federal deferral.

The biggest risk is the timeline. If you can’t identify or close on a replacement property within the deadlines, the exchange fails and you owe capital gains on the original sale. There are also "boot" rules — if the replacement property costs less than what you sold, or you take cash out, the difference is taxable. Additionally, the replacement property carries over the original cost basis, so depreciation recapture builds up over time. None of these are deal-breakers, but they require planning.