For a homeowner who has spent twenty, thirty or forty years in the same house, deciding to move is rarely just another real estate transaction. It can mean sorting through decades of belongings, determining what furniture will fit in a smaller home, comparing a condominium with a ranch or townhome, weighing proximity to family against the pull of a familiar neighborhood, and recalculating property taxes and monthly maintenance. Sometimes it means selling a home tied to an estate or major family transition.
Winfield Cohen of Keller Williams Success Realty: North Shore Group, who has served Northbrook, Chicago’s North Shore and the Northwest Suburbs since 2004. He prefers the word “rightsizing” to “downsizing” because the goal is not necessarily to have less house, but to find the right home for the way someone wants to live now.
“Rightsizing is really about deciding what you want the next chapter of your life to look like and then building the move around that,” Cohen said. “There are financial decisions, emotional decisions and logistical decisions, and they all deserve a clear plan.”
Why Longtime Homeowners Start Thinking About a Move
According to the National Association of REALTORS® 2026 Home Buyers and Sellers Generational Trends Report, as summarized by Virginia REALTORS®, baby boomers represented 55 percent of home sellers and 42 percent of home buyers, making them the largest group in both categories for the second consecutive year.
The report found that 41 percent of sellers and 31 percent of buyers cited wanting to be near friends and family as a reason for moving. More than half of younger and older boomers used proceeds from selling a primary residence as the down payment on their next home.
Cohen says this makes planning the sale and purchase together especially important. Illinois REALTORS® reported that in July 2026, the median sale price across the nine county Chicago metro area reached $401,000, up 6.8 percent from a year earlier, while the number of homes for sale fell 11.9 percent to 13,970.
Homeowners consider rightsizing for many reasons, including reducing yard maintenance, finding a single level floor plan, moving closer to family or healthcare, and freeing up time and money for travel and hobbies. Cohen recommends starting early rather than waiting until circumstances force a rushed decision. Depending on the amount of sorting required, market conditions and the availability of a suitable next home, a transition can take several months.
Cohen’s Four Phase Rightsizing Roadmap
Phase One: Preparation and Planning, Six to Twelve Months Out
Homeowners should first consider their desired lifestyle, whether that means a condominium, an active adult community, a smaller home or living closer to family.
Cohen recommends consulting financial professionals early. The IRS allows eligible homeowners to exclude up to $250,000 in home sale gains, or $500,000 on a joint return, subject to requirements. Homeowners aged 65 and older may also qualify for the Cook County Senior Exemption, which reduces a qualifying home’s equalized assessed value by $8,000.
Planning may also involve real estate professionals, move managers, estate sale specialists, contractors, movers, cleanout services and legal representatives for probate or trust matters.
Phase Two: Sorting and Decluttering, Three to Six Months Out
Sorting decades of belongings can be challenging. Cohen recommends starting with less sentimental spaces, such as a pantry, guest room or linen closet, before tackling attics, basements and family photographs.
Homeowners can sort items into four categories: keep, sell, donate or discard. Measuring furniture against the next home’s floor plan helps avoid moving items that will not fit. For unused belongings, the one year rule can help guide decisions. Scanning photographs and important documents also preserves family history while reducing storage needs.
Phase Three: Preparing the Home for Market, One to Two Months Out
Once belongings have been reduced, attention turns to the property. Cohen cautions that an expensive remodel is not always necessary. Instead, he recommends improvements that make a home look clean, maintained and easy to understand, including fresh neutral paint where needed, working lighting, professional carpet cleaning, minor repairs, decluttering and improved curb appeal.
Packing away some family photographs and collections can help buyers picture their own belongings in the space. For older properties, a pre listing inspection may identify manageable issues involving plumbing, electrical systems, roofing or aging mechanical equipment before a buyer’s inspection. Whether an inspection makes sense depends on the property.
Phase Four: Moving Week and the First Days in the New Home
Cohen recommends preparing a first day essentials box with medications, toiletries, phone chargers, important documents, a change of clothes, bedding and other items that must remain accessible.
After arriving, setting up the bedroom and bathroom first can make the initial night more manageable. Other unpacking can wait until the essentials are in place.
Choosing the Right Home and Community
Cohen says the next residence deserves as much consideration as the property being sold. Options for Northbrook area homeowners include condominiums, townhomes, ranch and single level homes, independent living residences, and 55+ or active adult communities in areas such as Glenview, Buffalo Grove, Deerfield, Lincolnshire, Barrington, Highland Park, Lake Forest, Wilmette and Arlington Heights.
The right choice depends on priorities such as maintenance, stairs, garage space, room for visiting family, association fees, access to transportation and healthcare, community activities, and proximity to friends and family. Some homeowners want social amenities, while others simply want fewer repairs and a home that is easier to manage.
Cohen also cautions against assuming a longtime family home needs a major renovation before it can sell. The appropriate strategy depends on the property and buyer demand in its neighborhood and price range. Northbrook, Deerfield, Glenview, Highland Park, Wilmette, Winnetka and Lake Forest can differ in inventory, property types and pricing, making local comparable sales and current competition important considerations.
Probate Experience and Life Transitions
Cohen holds the Certified Probate Real Estate Specialist designation. His probate practice includes coordinating with attorneys, executors, beneficiaries and appraisers on estate property sales, including paperwork, deadlines, cleanouts and determining market value.
Probate and conventional rightsizing sales are different, but both can involve years of belongings, multiple family members, repair decisions and emotionally significant deadlines. Cohen says this experience informs his work with homeowners navigating major life transitions.
“A successful downsize should feel like you are moving toward something, not simply giving something up,” Cohen said. “The home may be smaller, but if it gives you more time, less maintenance, the right location and a lifestyle that fits where you are today, that is a successful move.”
About Winfield Cohen
Winfield Cohen is a real estate broker with Keller Williams Success Realty: North Shore Group, serving Northbrook, Chicago’s North Shore and the Northwest Suburbs since 2004. His record includes over 900 transactions and $400 million in closed sales. He holds the Certified Probate Real Estate Specialist designation and has received regional sales recognition. His services include residential sales, probate properties, rightsizing and cleanout coordination. Learn more at winfieldcohen.com, Facebook, Instagram, YouTube, LinkedIn, TikTok, Zillow, Yelp, Realtor.com, FastExpert, Google Business Profile. Email at [email protected].