One of the most common questions we’re hearing right now is:
“Can we buy before we sell — without taking on too much risk?”
On Martha’s Vineyard, that question carries more weight than it does in most markets. Inventory is limited. Seasonality matters. Ferry schedules, summer rentals, school calendars, contractors — it’s rarely just a simple transaction. And for many homeowners, the idea of carrying two mortgages — even temporarily — feels uncomfortable.
The good news? There isn’t just one way to structure a move. Let’s break down the options.
The Real Stress Isn’t the Loan — It’s the Timing
Most buyers aren’t panicking about interest rates. They’re stressed about coordinating two closings, moving decades of belongings, avoiding a “double move,” and making sure they don’t lose out on the home they really want.
On Martha’s Vineyard, where desirable properties can move quickly when they’re priced correctly, hesitation can cost you the opportunity. But rushing without a plan creates a different kind of stress. Strategy matters.
Option 1: The Bridge Loan
A bridge loan allows you to tap into the equity of your current home to purchase your next property before selling.
Pros: Compete strongly as a buyer; avoid sale contingencies; move quickly when the right property appears.
Cons: You may need to qualify while carrying two mortgage obligations; it increases short-term financial exposure; it’s not ideal for everyone’s comfort level.
Bridge loans can absolutely be the right tool — especially for financially strong buyers with significant equity. But they’re not the only solution.
Option 2: Home Equity Line (HELOC)
In some cases, homeowners may use a HELOC to access equity before listing. This can provide flexibility, offer lower upfront costs than a bridge, and help with down payment structuring. However, qualification and timing need to be carefully planned — ideally before your current home is listed.
Option 3: The 60-Day Rent Back (Often the Most Elegant Solution)
This is the strategy we’re seeing work beautifully in our market.
After closing, seller rents the home back from the buyer for up to 60 days. That means you close on your sale, access your equity, purchase your next property, gain up to two months to move, and avoid qualifying with two full mortgage obligations.
No double move. No storage shuffle. No frantic ferry reservations.
Why This Is Especially Powerful for Second-Home Buyers
On Martha’s Vineyard, many purchases are second homes — and second-home buyers often have something incredibly valuable: flexibility.
Unlike primary homeowners, they typically don’t need to move in immediately. That means they can offer a seller a 30- to 60-day rent back without disrupting their own life. In competitive situations, that flexibility can be just as attractive as price.
We’ve seen cases where a slightly lower offer wins because it includes a generous rent-back period. Sellers often choose the buyer who makes their transition easier. Negotiations can improve because the buyer offers time instead of just dollars.
On the Vineyard — where many sellers are relocating off Island — giving them breathing room can add real value. Sometimes flexibility is currency. In the right situation, it can mean a smoother negotiation, stronger offer acceptance, or even a better purchase price. It’s not about overpaying. It’s about structuring intelligently.
Why Planning Early Matters on Martha’s Vineyard
In many areas, housing inventory has been gradually improving year-over-year. But Martha’s Vineyard doesn’t behave like the mainland. We’re geographically limited, seasonally influenced, and heavily driven by second-home demand.
When inventory increases even slightly, prepared buyers win — especially those who’ve already mapped out their financing structure. Waiting until you “find the house” is usually too late to optimize strategy.
Working With the Right Lending Partner
Structuring a simultaneous buy and sell requires coordination between agent, lender, and sometimes attorneys. We often collaborate with trusted lending partners like Meryl and Lauren at Leader bank to evaluate bridge scenarios, ARM versus fixed-rate strategy, equity timing, and overall qualification structure.
The right solution is highly personal. What works for one homeowner may not make sense for another.
The Bottom Line
If you’re thinking about upsizing, downsizing, transitioning from seasonal to year-round, or purchasing your first Martha’s Vineyard property while selling elsewhere, there are multiple ways to make the timing work.
The key is planning before you need to. On Martha’s Vineyard, smooth moves don’t happen by accident — they happen because the strategy was built early.
If you’re considering a move this year, let’s map it out. Even if it’s months away, clarity now creates leverage later.
