Rightsizing in Portland: Options, Timeline, and Strategy

Rightsizing is one of the most personal real estate decisions someone can make. It is rarely just about square footage or price. It is about timing, lifestyle, finances, and how much change someone is comfortable navigating all at once.

As a Portland Realtor and Listing Agent, I help homeowners work through this decision every day. One of the most common questions I hear is how to sell a current home and move into the next one in a way that feels thoughtful, manageable, and aligned with real life.

There is no single right answer. The best strategy depends on the person, the market, and the moment. What works well in one season or market cycle may not make sense in another. My role is to help people understand their options clearly, evaluate tradeoffs, and choose a path that fits their priorities.

In Portland, rightsizing typically falls into three main approaches.

Option 1: Buy First, Then Sell

For some homeowners, buying first provides peace of mind. It allows them to focus on finding the right next home without the pressure of coordinating a sale at the same time.

This approach can work well when someone has the financial flexibility to carry two homes temporarily, access bridge financing, or leverage other assets to purchase before selling.

Buying first can reduce stress around timing and uncertainty. It allows people to move once, settle into their new home, and then prepare their current home for sale without living through showings, repairs, and inspections.

From a listing standpoint, this often leads to a calmer and more strategic sale because the home can be prepared properly and brought to market at the right time.

Buying first requires careful planning. Carrying costs, market conditions, and exit strategy all matter. This is where working with an experienced Portland Listing Agent is critical. I help clients evaluate the numbers, coordinate with lenders, and create a clear plan so this option feels intentional rather than risky.

Option 2: Buy and Sell at the Same Time

Buying and selling simultaneously is one of the most common rightsizing paths in Portland, and also one of the most nuanced. It requires coordination, strong communication, and realistic expectations.

This approach often involves contingent offers, strategic pricing, and thoughtful timing on both sides of the transaction.

During the peak Covid years, getting a contingent offer accepted was virtually unheard of. The market strongly favored non contingent buyers, and sellers had little reason to take on additional uncertainty.

Over the last few years, however, I am increasingly seeing contingent offers become a real possibility again when they are structured properly. This is especially true when the home being sold is well prepared, priced appropriately, and positioned strategically.

Buying and selling at the same time allows people to use equity from their current home without carrying two properties. When done thoughtfully, it can be efficient and financially practical.

A contingent offer is only as strong as the plan behind it. Pricing strategy, market conditions, preparation, and communication all play a role. As a Realtor handling both sides of the transaction, I help clients understand how contingencies work in real terms and how to position their offer and listing so expectations are clear and stress is minimized.

Option 3: Sell First, Then Buy

Selling first offers clarity and leverage. Once the sale is complete, homeowners know exactly what they have to work with financially and can move forward confidently.

This approach can work particularly well for people who value certainty or want to simplify the process.

Selling first removes financial guesswork and can make buyers more competitive when they are ready to purchase. It can also allow homeowners to take advantage of strong selling conditions without feeling rushed into a purchase decision.

Selling first is also often the best strategy when buying new construction. Builders typically want to close as soon as the home is complete. When a home is ready, they expect to close, which means having a contingency tied to selling another property can be difficult or impossible. In these situations, selling first can create a much smoother path forward.

Selling first requires a thoughtful plan for the in between period. This might include rent backs, short term rentals, or temporary housing. When planned intentionally, this phase can be surprisingly manageable and even flexible.

As a Listing Agent, I help clients think through these logistics early so there are no surprises later.

Why Timeline and Strategy Matter So Much

Rightsizing is not just about choosing an option. It is about aligning that option with current market conditions and with your personal tolerance for risk, change, and uncertainty.

The Portland real estate market shifts. Inventory levels change. Interest rates move. Buyer behavior evolves. What made sense six months ago may not be the right approach today.

This is why I spend significant time upfront helping clients understand not only what they want to do, but how and when to do it.

A clear timeline reduces stress.
A thoughtful strategy creates leverage.
Experienced guidance makes complex moves feel manageable.

How I Help Homeowners Rightsize in Portland

Last year, I helped more than 50 clients buy and sell homes across the Portland metro area. Most of them were navigating some form of life transition that required rightsizing in one way or another.

My role is not to push a single approach. It is to help people see their options clearly, understand tradeoffs, and move forward with confidence.

I help by walking through buy first, sell first, and simultaneous strategies, coordinating with lenders and other professionals, creating realistic timelines, preparing homes strategically for sale, communicating clearly throughout the process, and adjusting strategy as market conditions change.

For additional perspective, you may also find these resources helpful:

Navigating the Downsizing Journey in Portland, Oregon
https://shannonjanssenrealestate.com/blog/navigating-the-downsizing-journey-in-portland-oregon

Top 5 ROI Home Improvements Before Selling Your Portland Home
https://shannonjanssenrealestate.com/blog/top-5-roi-home-improvements-before-selling-your-portland-home

If you are starting to explore homes or want to keep an eye on opportunities, you can search listings and sign up for alerts here:
http://shannonjanssen.realscout.com/

The Right Choice Is Personal

There is no universal answer to how someone should rightsize. The right decision is personal and influenced by lifestyle, finances, comfort level, and the market at the time.

If you are thinking about a move, even in a general or long term way, a conversation can bring clarity. And if you know someone who is no longer loving where they live or feels stuck in the wrong space, an introduction is always appreciated.

You can connect with me directly here:
https://shannonjanssenrealestate.com/contact-us

Rightsizing works best when it is intentional, well planned, and aligned with real life.