Downsizing from Streeterville: What Empty Nesters Should Know Before Selling

Key takeaways:

• Empty nesters selling in Streeterville should address capital gains planning, condo-specific disclosures, and their next home strategy before listing — not after.
• The Streeterville market skews heavily toward high-rise condos, so your sale price, timeline, and buyer pool are all shaped by building-level factors unique to this neighborhood.
• Getting the sequencing right — what to prepare, when to list, and where to land next — is what separates a smooth transition from a stressful one.

Downsizing from Streeterville means navigating a condo-dominated market where building health, assessment history, and unit positioning matter as much as square footage. Empty nesters selling here typically hold significant equity, face real capital gains questions, and need a clear plan for their next chapter before the sign goes up. The good news: with the right preparation, a Streeterville sale can fund a genuinely freeing next move.

That next chapter looks different for everyone — a smaller condo in the same neighborhood, a suburban single-family, a warmer climate, or a lock-and-leave in a walkable city pocket. Whatever the destination, the steps on the selling side are largely the same, and getting them right early is what gives you control over timing and outcome.

Where Streeterville Sellers Start: Knowing What You Actually Own

Before thinking about list price, empty nesters in Streeterville need a clear picture of their unit's position within the building. High-rise condos here are not priced in a vacuum — buyers evaluate the unit, the floor, the views, the building's financial health, and the monthly assessment all at once.

A few things to get your arms around early:

• Your current monthly assessment and what it covers. Buyers will ask, and a high assessment relative to what it includes can affect how your unit is perceived against comparable listings.
• Whether any special assessments are coming. If the board has discussed a major capital project — a new roof, elevator modernization, facade work — buyers will find out during attorney review. Knowing this in advance lets you decide how to disclose and price accordingly.
• Past special assessments. If your unit carried one in the last several years, that history is relevant to a well-informed buyer.
• The reserve fund status. You won't be handing buyers a reserve study before they write an offer — that comes during attorney review — but understanding whether the building is well-funded gives you a realistic sense of how buyers will react once they're under contract.

None of this is about hiding anything. It's about going into the sale informed so you're not caught off guard by a buyer's concerns or a deal that unravels in attorney review over something you could have anticipated.

The Capital Gains Conversation You Need to Have First

This is the piece that catches the most empty nesters by surprise. If you've owned your Streeterville unit for a long time and values have appreciated substantially, the gain on the sale may be significant. The federal primary residence exclusion allows individuals and married couples to exclude a portion of that gain from taxable income — but only if you meet the ownership and use requirements, and only up to the exclusion limit. Do not assume the exclusion covers your entire gain without running the actual numbers.

Illinois also has its own income tax treatment of capital gains, which a tax professional can walk you through. The City of Chicago does not impose a local income tax, but there is a real estate transfer tax applied at closing — your attorney will confirm the current rate and which party customarily pays what portion.

The right move here is to sit down with a CPA or tax advisor before you list, not after you accept an offer. Knowing your approximate net after taxes is what lets you plan your next purchase intelligently. It also helps you decide whether timing the sale in a particular calendar year makes sense for your broader financial picture.

Pricing a Streeterville Condo in the Current Market

Streeterville's high-rise inventory means buyers have genuine comparison points. Your unit will be evaluated against other units in your building, against competing buildings along the lakefront and Michigan Avenue corridor, and against what has actually closed in the last few months — not what sellers hoped to get.

Pricing strategy here involves a few layers:

1. Comparable closed sales in your building and in competing buildings within the last three to six months. This is the foundation of any honest pricing conversation.
2. Active competition. How many similar units are on the market right now, and how long have they been sitting? Days on market in Streeterville varies by floor, view, and unit condition.
3. Unit-specific factors. High floors with lake or city views command meaningful premiums over mid-rise units in the same building. Parking — whether deeded or assigned — matters to buyers here in ways it might not in other neighborhoods.
4. Condition and presentation. Buyers in this segment are accustomed to high-quality finishes. A dated kitchen in an otherwise well-located unit will price accordingly, and buyers will calculate the renovation cost and subtract it.

Where many sellers go wrong is anchoring to what a neighbor sold for two or three years ago, or to what Zillow's estimate says. Neither reflects current buyer demand or the specific condition of your unit. A current comparative market analysis built on actual closings is where the conversation needs to start.

If you want to know how to evaluate an agent before you commit to listing with anyone, the guide on how to choose the right REALTOR® in Chicago walks through the questions worth asking.

Preparing the Unit: What Empty Nester Sellers Should Actually Do

The tendency after the kids are gone is for a home to accumulate things — furniture that was useful, items that were stored, rooms that served purposes that no longer apply. Before listing in Streeterville, the practical steps look like this:

1. Declutter aggressively. High-rise condos photograph and show best when they feel spacious. Crowded rooms photograph small, and square footage is a primary selling metric in this market.
2. Address deferred maintenance. Scratched hardwood floors, dated lighting fixtures, tired paint — these are inexpensive to fix and disproportionately affect buyer perception. A buyer doing a walkthrough is looking for reasons to negotiate.
3. Consider professional staging. Streeterville units compete online first. Professionally staged, well-photographed listings get more showing requests. Empty units, counterintuitively, often show worse than furnished ones because scale is hard to read.
4. Confirm parking and storage details. Know exactly what conveys with the unit — deeded parking space number, storage cage location — because buyers will ask and any ambiguity creates friction.
5. Pull together your condo documents. While buyers don't review the full condo packet until after going under contract, having your association contact information, the current assessment amount, and any recent correspondence from the board organized in advance saves time once you're under contract and the clock is ticking.

The Sequencing Question: Sell First or Buy First?

This is the tension most empty nesters wrestle with, and there's no universal answer — it depends on your financial position, your risk tolerance, and where you're going next.

• Approach: Sell first, then buy; Upside: Know your exact proceeds before committing to next purchase; Downside: Risk of temporary housing gap; may feel rushed on the buy side
• Approach: Buy first, then sell; Upside: No gap in housing; move directly into next home; Downside: Carrying two properties; may need bridge financing
• Approach: Contingency-linked; Upside: Ties the two transactions together; Downside: Harder to negotiate in competitive markets; sellers may reject contingent offers

For empty nesters with strong liquidity who aren't dependent on their Streeterville sale proceeds to fund the next purchase, buying first can reduce stress considerably. For those whose next home is largely financed by the sale, selling first and arranging short-term housing is often the cleaner path.

The article on downsizing sellers in Andersonville covers this sequencing question in detail and is worth reading even if you're not headed to that neighborhood — the financial logic translates.

If your next move keeps you in a Chicago high-rise, the considerations that remote workers evaluate in Streeterville buildings — including building amenities, home office setups, and unit layouts — are covered in why Streeterville keeps attracting buyers who want to own in Chicago, and the building-level evaluation points apply to any buyer in this market.

How Riley Hextell Works with Empty Nester Sellers in Streeterville

Riley Hextell is ranked number one at eXp Realty Illinois for total transactions in 2025 and is in the top 50 of more than 80,000 agents companywide. He earned the 2024 Chicago Association of Realtors Rookie of the Year award and holds 141-plus five-star Google reviews. As a U.S. Navy veteran, he brings a direct, no-pressure approach to complex transactions — which is exactly what a high-stakes, life-stage sale like this one calls for.

Working with empty nester sellers in Streeterville, Riley starts with a thorough comparative market analysis grounded in recent closings, walks through the building-specific factors that will shape buyer reception, and helps sellers think through the sequencing of their sale and their next move before committing to a timeline.

You can reach Riley at 815-545-7476, [email protected], or at rileyhextell.com.

Have a question about your situation?

Want a current comparative market analysis for your Streeterville unit — including how your building's assessment history and reserve status are likely to land with buyers? Reach out and Riley will pull the numbers together for your specific unit.

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Frequently Asked Questions

How long does it typically take to sell a condo in Streeterville?

Time on market in Streeterville varies by unit condition, floor, pricing, and current inventory levels. Well-priced, well-presented units in buildings with clean financials tend to move faster. Units priced above market or in buildings with known assessment concerns often sit longer. A current market analysis specific to your building and unit type will give you the most accurate expectation.

Do I owe capital gains tax when I sell my primary residence in Streeterville?

Potentially, yes — depending on how long you've owned the unit, how much it has appreciated, and whether you meet the IRS ownership and use requirements for the primary residence exclusion. The exclusion has limits, and gains above those limits are taxable. Illinois also taxes capital gains as ordinary income. Sit down with a CPA before you list to know your approximate net after taxes.

What happens if a special assessment is coming when I'm trying to sell?

A pending or anticipated special assessment needs to be disclosed to buyers. How it's handled — whether the seller pays it, the buyer assumes it, or it's credited at closing — is negotiated as part of the transaction. Knowing about it in advance gives you time to decide your approach rather than scrambling after you're already under contract.

Should I renovate my Streeterville condo before listing, or sell it as-is?

Minor cosmetic updates — fresh paint, refinished floors, updated fixtures — generally deliver strong returns in buyer perception relative to their cost. Major renovations rarely return dollar-for-dollar at resale, and buyers often prefer to customize finishes themselves. The right answer depends on the specific condition of your unit and what comparable listings look like right now. Your agent can walk you through what's worth doing versus what to leave alone.