Your home is more than a place to live. For most couples I work with, it is often the second-largest asset (after their investment accounts). And when you’re in your 50s, starting to think about what retirement actually looks like, that house starts playing a bigger role in the conversation.

Maybe you’re considering a move closer to family. Maybe you want something smaller and easier to maintain. Or maybe you’re trying to figure out if selling now versus later changes your timeline for leaving work. Whatever the reason, the decision to sell isn’t just about real estate. It’s about cash flow, taxes, timing, and peace of mind.

That’s why I recently sat down for a conversation with Dan Mower, who leads the Mower-McLennan Team at Keller Williams Realty in Corning, New York. Dan’s been doing this for nearly two decades, and he brings a level of detail and clarity that I really appreciate. I wanted to walk through the process from a financial planning lens and get his take on what buyers and sellers should actually be paying attention to right now.

Why Your Home Matters in Your Retirement Plan

When I’m building a financial plan with a couple approaching retirement, the house almost always comes up. Sometimes it’s about freeing up equity to fund the next chapter. Sometimes it’s about reducing expenses so one person can step back from work sooner. And sometimes it’s just about simplifying life.

But here’s the thing: selling a home is a big transaction with a lot of moving parts. The timing matters. The tax implications matter. And if something goes wrong during the sale, it can throw off your whole plan.

I’ve seen clients assume their home is worth a certain amount, only to find out the market disagrees. I’ve seen deals fall apart over inspections or financing issues that could have been avoided. And I’ve seen people pick an agent based on who gave them the highest price estimate, which almost never ends well.

So before you list, it’s worth understanding what you’re getting into and who you’re working with.

How to Pick the Right Real Estate Agent

Most people pick an agent because a friend recommended them or because they’re the one who keeps mailing postcards. But Dan’s advice is simple: interview at least two agents. 

“Think of your real estate agent as a risk manager,” Dan told me. “You’re not just looking for someone to stick a sign in your yard. You’re looking for someone who’s going to mitigate risk, communicate well, and make sure nothing falls through the cracks.”

So what should you be asking? Here are a few questions that get to what actually matters:

1. What’s your average days on market? 
   This tells you how long it typically takes them to sell a home. If their average is way higher than the market norm, that’s a red flag.
   
2. What’s your list price to sale price ratio? 
   Most agents will tell you what homes sold for compared to the final list price. But Dan says you should ask about the original list price to sale price ratio. That number shows whether they’re pricing homes accurately from the start or chasing the market down with price drops.
   
3. What’s your marketing strategy? 
   You want to hear a clear plan, not just “we’ll put it online and see what happens.” Dan’s team has a structured model built around where buyers actually look and what motivates them to act. That’s the kind of intentionality you’re looking for.

And here’s the thing: the agent who suggests the highest price isn’t always the best choice. In fact, they might be telling you what you want to hear just to get the listing. Your decision should be about who’s the right person to represent you, and then you talk about price.

What Kills Deals and How to Get Ahead of It

Even when a buyer and seller agree on price, things can still fall apart. The two most common reasons? Inspections and financing.

On the inspection side, Dan recommends getting a pre-inspection before you list. “It’s a great way to know what you’re dealing with upfront,” he said. “You can address issues for pennies on the dollar before they become negotiation points. Or you can disclose them upfront so buyers go in with their eyes open.”

I love this approach because it removes surprises. Surprises freak people out. And when people get freaked out, they start questioning everything else about the deal.

On the financing side, working with a well-regarded local lender can make a big difference. Dan’s seen deals drag out or fall apart because of delays with national banks or less experienced lenders. He also mentioned that survey issues are becoming more common and can kill deals if they’re not handled early.

The other thing that helps? Making sure your agent, your attorney, and your lender are all communicating. “Be the squeaky wheel,” Dan said. “Check in regularly. Your file will move up the pile if you’re staying in touch.”

Reading Today’s Market as a Seller

Right now, in early 2026, as this is being written, the market feels a little strange. Inventory is still low compared to historical norms, but homes are sitting longer than they were a couple of years ago.

Dan explained it this way: “We’re about two-thirds of what normal inventory would be, but the market is acting balanced. Buyers are jumping on homes that are well-prepared and priced right. But they’re rejecting homes that are overpriced or not ready.”

In other words, it’s a finicky market. Buyers are being careful. They’re not bidding over asking on everything like they were in 2022. So if you’re thinking about selling, preparation and pricing matter more than ever.

That means decluttering, making small repairs, and working with an agent who knows how to position your home. It also means being realistic about what your home will actually sell for, not what you hope it will sell for.

Getting a Realistic Home Valuation

A lot of people check Zillow or look at their tax assessment and assume that’s what their home is worth. But those numbers can be way off, especially in areas with older housing stock and varied properties.

“Automated valuation models work well in places with newer developments where all the homes are similar,” Dan said. “But when you’ve got a mix of older homes, updates, and different property types, the algorithms struggle.”

So what should you do? Dan recommends looking at your tax assessment, Zillow, and maybe Homes.com, and using those as a starting point. But don’t rely on them. Get a real evaluation from an experienced local agent who knows the market and can pull actual comparable sales.

What This Means for Your Plan

If you’re a couple in your 50s and thinking about selling your home in the next few years, my advice is to start the conversation now—not just with an agent, but with your financial planner.

We need to talk about timing, tax implications, and how the proceeds fit into your bigger picture. We need to make sure you’re working with the right people and that everyone’s on the same page.

Your home is a big part of your financial life. Treating the sale with the same care and intentionality you bring to the rest of your planning makes all the difference.

If you’d like to talk through how a home sale fits into your retirement timeline, let’s set up a time to chat. I’m here to help you think it through.

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 438-2914, Ithaca, NY office at (607) 463-8400, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/ 

This material has been edited with the assistance of artificial intelligence tools. The information presented is based on sources believed to be reliable and accurate at the time of publication. This material is for educational purposes only and does not necessarily reflect the views of the author, presenter, or affiliated organizations. It should not be construed as investment, tax, legal, or other professional advice. Always consult a qualified professional regarding your specific situation before making any decisions.