Every year, I sit at a kitchen table or on a screened porch overlooking the water with someone who asks me the same quiet question:
“Did we miss the best time to sell?”
Usually the house has been loved for decades.
There are pencil marks in a closet, a dock that has hosted more crab feasts than anyone can count, and a view the owners still pause to look at every evening.
They are not unhappy.
They are uncertain.
They are using the home differently now than when they bought it. Travel is harder. Maintenance feels heavier. Stairs feel steeper. The children visit, but they have homes and lives of their own. And the owners begin to wonder if they are holding onto a memory more than a lifestyle.
Then the real question appears:
Should we sell… or should we wait?
Most people think this is a market question.
It usually isn’t.
Waterfront Homes Do Not Follow the Normal Market
Waterfront property behaves differently than almost any other real estate.
Typical homes are influenced heavily by interest rates and inventory. Buyers compare dozens of similar houses.
Waterfront buyers don’t shop that way.
They are not just buying a structure. They are buying a setting, a feeling, and a daily experience. A specific shoreline, a certain sunset direction, proximity to a marina, protected water for a boat, or a view they have wanted for years.
That means something important:
There are almost always buyers for the right waterfront home, regardless of the headlines.
I have seen waterfront homes sell quickly in slow markets and sit in strong markets. The difference is rarely timing. It is preparation, presentation, and clarity of decision.
Waiting for a “perfect market” is usually less important than understanding whether the home still fits your life.
Five Questions Every Waterfront Owner Should Ask
Before worrying about interest rates or predictions, I encourage owners to ask themselves these questions.
1. Are you still using the home the way you imagined when you bought it?
Many families bought waterfront homes for boating, entertaining, and full summers on the water. Years later, schedules change. Health changes. Grandchildren live farther away. Sometimes the house becomes a place you maintain more than a place you enjoy.
2. Is the property beginning to manage you?
Bulkheads, docks, landscaping, flood insurance, painting, and upkeep are part of waterfront ownership. At a certain point, some owners realize they spend more time arranging service providers than sitting on the porch.
That realization matters more than any market statistic.
3. Would you choose this same house again today?
This is often the most honest question.
If you were moving to Annapolis right now, would you buy this exact property again, or would you choose something smaller, simpler, or closer to town?
Your answer tells you a great deal.
4. Are your children realistically going to keep it?
Many owners hold a property for family legacy reasons. Sometimes that is absolutely right. Other times, children love the home but live busy lives in other cities and quietly worry about the responsibility.
A conversation with them often brings clarity and relief.
5. Are you deciding from confidence or uncertainty?
The best real estate decisions come from clarity, not pressure. If you feel unsure every year but take no action, the uncertainty itself becomes the burden.
The Mistake I See Most Often
The most common decision I see is waiting for a “better market.”
Here is what typically happens instead:
Owners wait a few years, maintenance increases, and then a life event forces a quicker sale than they would have preferred. The home is still valuable, but the process feels rushed instead of thoughtful.
Waterfront buyers are lifestyle buyers. They are less sensitive to interest rates than buyers of typical homes. What they respond to is a well-prepared, properly presented property that feels ready for its next chapter.
In many cases, the cost of waiting is not market prices.
It is missed opportunity to plan the transition calmly and intentionally.
Selling Is Not the Only Option
An important part of this conversation is that selling is not always the right answer.
Some owners:
- keep the home and make strategic improvements
- transition to seasonal use
- rent for a period of time
- help family begin using the property differently
- or decide to sell later with a clear plan
My role is to help you understand your choices so you can make a decision you feel at peace with.
A good real estate decision should still feel right five years later.
So… Should You Sell in 2026?
The honest answer:
The best time to sell a waterfront home is rarely about the year.
It is about whether the home still fits your life today.
If it does, you should enjoy it fully and without second-guessing.
If it doesn’t, the right preparation and guidance can help you move forward thoughtfully instead of reactively.
If you are beginning to wonder what the next chapter might look like, I am always happy to talk through options, even if selling is not the outcome. Sometimes a conversation simply brings clarity, and clarity itself is valuable.