Stress-Free Moving

Essential Tips For Downsizing Your Home

By Josephine D’ippolito

Photography by Marisa S White

Transitioning into a new chapter of life often involves moving and downsizing, a process that can be emotionally challenging and logistically complex. So we decided to help. In this guide, we explore how to make this transition as smooth as possible with insights from Cate Bauer, Compass agent, and Debbie and David Feldman, the owners of Home Again Transitions, a full-service specialty & senior move management company for small and large projects/moves.

Is selling your home the right move?

Bauer says the decision to sell your home isn’t always straightforward, especially when emotions and financial considerations come into play. Some homeowners, she says, feel pressure to sell, but it’s important to consider all factors to ensure it’s the best decision.

“It is important to explore what the ‘next chapter’ means for people who are considering selling their family home,” she explains. “It’s crucial to have an honest conversation with yourself and your loved ones about all the considerations.”

Some questions to ask yourself/things to consider:

• Evaluate the financial implications: Do you have a low-interest mortgage that you would need to give up for a higher rate?

• Is the upkeep of your current home becoming too much?

How will downsizing to a condo or townhome impact your cost of living?

• Are you holding onto your large home, hoping that your grown children will visit more?

The key is to analyze your financial situation, lifestyle needs, and emotional readiness before making a move. Sometimes, staying put may be the best option—but if the work and cost of maintaining your home outweigh the benefits, it might be time to consider the next chapter. And if you’re not sure what your next chapter should look like, consider renting before buying to test a new location and lifestyle without fully committing.

Step one: Get your ducks in a row

Before you begin looking for new homes or new towns, determine what you really want. “Downsizing” might not always be the answer. According to Bauer, you can also “right-size” your life.

Right-sizing is about finding a home that aligns with your current needs and lifestyle. For some, this means moving to a similarly sized home in a less expensive area (think further north or to a nearby town with lower taxes). This will allow you to maintain the comfort of a larger space while benefiting from an affordable purchase price and significantly reduced taxes.

If you’re unsure which is right for you, or even if you are, the other essential part of the first step is choosing the right real estate agent. As Bauer emphasizes, trust and comfort are essential because you’ll spend significant time working closely with this person. A good agent will listen to your needs, respect your concerns and offer tailored solutions rather than a one-size-fits-all approach. A skilled realtor will guide you through every stage, from preparing and staging your home to managing the emotional aspects of leaving a long-time residence.

“Sometimes testing the market with an exclusive or private listing is an excellent way to ease into the selling process,” Bauer suggests. “These listings aren’t posted on the MLS, which can be ideal for those who value privacy or want to test their home’s pricing. Off-market listings can simplify the process for sellers, and buyers often appreciate avoiding bidding wars.”

Building a strong relationship with your realtor early on ensures a smoother transition, making the experience less stressful and more rewarding.

Step two: Prepare your current home for sale

Once you have an idea of where you want to live and you’ve found your realtor, it’s time to begin the home staging process. You can either hire a professional stager or you can do it yourself. If hiring a professional stager isn’t ideal or within budget, Bauer says the three most important things to do are:

Advice from a real-life downsizer

Rosie and Tim Stewart moved out of their Yorktown Heights home, where they’d lived for 22 years, when Tim secured a job in Bethesda, MD, in 2024. With their children grown, they decided to downsize to a new townhouse community close to shops and restaurants. Their journey was a rollercoaster of emotions, decisions and, let’s be honest, a lot of stuff.

Rosie’s top tip for anyone thinking of downsizing? “Start decluttering now if you think you’re going to move within the next five years!”

She quickly learned that downsizing isn’t just about packing—it’s about confronting years of accumulated “stuff” and, of course, dealing with those sentimental attachments.

To tackle the project, Rosie made a list of what hadn’t been used in a while or wouldn’t fit in her new space. She donated to local charities and sold or gave away items on Facebook Marketplace. For the heavier items, she called in College Hunks (yep, that’s a real company) for junk removal.

It took her several months, but once she was finished, Rosie felt a huge sense of relief. “It felt so good to get rid of everything!” she says, adding that she’s now more intentional before buying new things. “Do I really need it?”

One key lesson Rosie learned: When you’re moving a long distance, sometimes it’s cheaper to buy new furniture than to pay a moving company to haul your old couch across state lines. While Rosie’s new low-maintenance lifestyle is a win, adjusting to a new community takes time. “The loss of space takes some getting used to,” she admits. But the payoff in easier maintenance and convenience has made it all worth it.

De-clutter: This can be the most challenging, yet impactful, task when preparing a home for sale.

Remove personal items: Family photos and memorabilia, like sports gear, can distract potential buyers. A Red Sox fan might not appreciate your Yankees collection.

Fresh paint: Giving the home a new coat of paint can make a huge difference. Bauer recommends Benjamin Moore’s China White for a clean, neutral look.

5 ways to part with your belongings

1. Give them away. Offer items to family and friends (but don’t push). This way, you’re helping loved ones and saving yourself some time.

2. Sell to your buyer. If the buyer is open to it, leave behind furniture for a small (or no) charge. Remember, people don’t want to spend much on used furniture.

3. Sell your stuff. Auction houses, online platforms like Facebook Marketplace, or an estate sale are great ways to sell items.

4. Donate to a worthy cause. Various organizations will come to your home and take items free of charge. However, those items need to be bagged and placed in front of the home. They include:

• Big Brothers
• Greendrop
• Purple Heart
• Veterans Association

To donate furniture, reach out to Furniture Sharehouse of Westchester (they support economically disadvantaged families & individuals) or Habitat for Humanity.

5. Discard the rest. Sometimes, items need to be thrown away. Here are a few options:

• Responsible disposal: Recycle old tech at Staples or dispose of old medications at CVS.
• Bulk pickup: Many towns offer bulk pickup for a nominal fee, so check with your local municipality. Note: You will need to carry the heavy items to your curb.
• Call for help: Services like 1-800-GOT-JUNK or College Hunks will come inside your home and remove heavy items for you.

Since decluttering is such a daunting task, the Feldmans recommend doing it slowly. In fact, they say you should take it one drawer at a time and don’t expect to do an entire room in one day. If the drawer-by-drawer approach seems overwhelming, then set a 15-minute timer each day and see how much progress you can make. Gradually extend it to 30 minutes, and keep going until finally it’s all done.

As you declutter, create three piles: garbage, donate/sell, and maybe. This will keep you moving along. The goal is to have your “donate/sell” pile be larger than your garbage pile.

“We measure the closet space in terms of linear inches. If the new closet is smaller, the client knows it’s time to downsize their wardrobe.”

While this step seems logical and practical, it can be the most difficult. Leaving a home filled with memories can be one of the most challenging aspects of downsizing. Both Bauer and the Feldmans stress the importance of focusing on the future.

“Think about what you’re gaining,” Bauer advises. “A simpler, more focused lifestyle and a new home that supports your current needs.”

The Feldmans say you should consider repurposing heirlooms (e.g., using a small glass or vase as a pencil holder or a special family plate as a spot to drop your keys), digitizing photos and children’s artwork and considering donating meaningful items to organizations or museums. When it comes to your fine china. If there is no room to display your fine dishware in your smaller home and you really love it, then use it! Let it become your new everyday dishware.

Step four: Consider (then dismiss) the idea of a storage unit

Storage units can seem like an easy out, but they’re only worth it if you have a clear end date—meaning you actually know when you’ll move everything out. Otherwise, you’re just delaying tough decisions. (Spoiler alert: They usually end up costing you more time and money in the long run.)

“We’ve seen clients rack up storage bills with only a small fraction of the items worth keeping,” Debbie says. “Plus, moving things in and out of storage is just more work—what starts as a $300 per month bill can quickly balloon, sometimes doubling in just a few months.”

Without a clear plan, a storage unit can quickly turn into an unexpected financial burden. Don’t fall for it! Instead, return to step two and determine what you will throw away, what you will donate and what you will sell.

Step five: Know when to call in the pros

While this guide offers tips for those moving on their own, sometimes it’s best to hire professionals.

Consider calling in the pros if:

• An estate clearing is necessary.
• You are elderly or don’t have family in the area to help.
• You need to move quickly.
• Life is too busy or hectic to handle the move yourself.
• You simply don’t have the time or desire to manage it alone.

Whether you go it alone or hire someone to help you downsize, moving, especially when downsizing from a family home, can feel overwhelming. But with the right game plan and support, the process can be smooth and even rewarding. The biggest secrets to a successful move? Preparation, organization and knowing when to ask for help

This article was published in the March/April 2025 edition of Connect to Northern Westchester.