The Leverage Game: How to Win When Selling on Martha’s Vineyard

Jen Hawkins O'Hanlon, REALTOR®

06/24/25

The Leverage Game: How to Win When Selling on Martha’s Vineyard

If you're preparing to sell your home on Martha’s Vineyard, three key factors will determine your success: location, condition, and price.

Let’s break each one down.


📍 Location: Fixed, But Foundational

Your home’s location is what it is—whether it’s close to the beach, tucked into the woods, or walking distance to town. You can’t change it, but you can understand how it plays into buyer expectations and pricing. A prime location will naturally carry more value, but even if your location is less central, the right pricing and presentation can make a big difference.


🛠️ Condition: Your Decision

Some sellers make strategic improvements—like fresh paint, updated lighting, or simple landscaping—to boost appeal. Others list as-is. Either approach is fine, but it’s important to remember that today’s buyers expect clean, well-maintained, move-in ready homes. If your home needs work, the price needs to reflect that.


💲 Price: The Factor You Control Most

Location is fixed. Condition is flexible. But price?
That’s where your strategy—and your leverage—comes in.

Buyers today are highly informed. They’re not just browsing listings—they’re studying the market. They're looking at what has sold, not what’s sitting unsold. Active listings may look like comps, but most buyers know better. If they think a home is overpriced, they’ll scroll right past it.


💼 Price Smart to Keep the Leverage

Here’s the truth: if you price your home with “negotiation room,” you’re giving away leverage from the start.

Today’s buyers—especially on Martha’s Vineyard—are watching the market closely. Most are looking for second homes and are carefully weighing long-term costs. They factor in:

  • The 2% Land Bank fee

  • The potential cost of future real estate commissions

  • Whether the home will appreciate enough to justify the investment

If they don’t see immediate value or upside, they’re not making offers—they’re moving on.

Overpricing in hopes that someone “loves it enough” to negotiate down just doesn’t work anymore. These buyers are savvy, selective, and strategic.

But when you price at market value—or even slightly below—you flip the dynamic. Now you have the leverage:

  • You drive showings and generate interest

  • You create urgency

  • You may even attract multiple offers

And that puts you in control.


🕐 Timing Matters: Don’t Miss the Window

Martha’s Vineyard is a seasonal market. Roughly 90% of buyers are looking for second homes, and once fall hits, many pause their search until the following spring. Your strongest window to sell is from late spring through the summer, when buyers are here and ready to make decisions.

Some sellers “test the market” by listing high, then pull the home if it doesn’t sell after 6 to 12 months. This strategy contributes to the higher Average Days on Market on Martha’s Vineyard compared to other areas. But just because longer timelines are common here doesn’t mean they don’t matter. Unless you're comfortable holding onto the property or renting it out for another season, pricing too high from the start can lead to missed opportunities—and delay your ability to move forward.


Key Takeaways for Sellers on Martha’s Vineyard

  • Price is your power tool. Use it strategically to keep control of your sale.

  • Buyers are smart. They’re calculating every cost—now and down the road.

  • Condition matters. You don’t have to make every upgrade, but your pricing needs to reflect reality.

  • Seasonal timing is everything. Don’t let the window close while you’re “feeling it out.”


🏁 From The O’Hanlon Group: Smart Pricing Starts with Strategy

At The O’Hanlon Group, we work with sellers to price homes for today’s market—based on data, buyer behavior, and timing. We understand that your home carries emotional value, but our job is to bring objectivity, strategy, and clarity to help you achieve your goals.

Want to know where your home stands and how to price it right? Let’s talk.
We’ll look at the comps, your timeline, and what today’s buyers are really willing to pay.

WORK WITH THE O'HANLON GROUP

As a team, we work in harmony for the benefit of our clients. We handle multiple transactions at once and are able to execute a complex marketing strategy by leveraging team resources. We can be in several physical locations at once to ensure showings are always possible for our buyers and sellers. Our clients benefit from the combined experience of our agents and administrative staff.

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