Key takeaways:
- Downsizing in Chicago works best when you match the right neighborhood and property type to your actual lifestyle — walkability, amenities, and building quality matter more than square footage alone.
- Condos dominate the downsizing market in Chicago, so understanding assessments, reserve health, and special assessments before writing an offer is essential.
- Coordinating the sale of your current home with the purchase of a smaller one requires careful sequencing — an experienced agent makes that timing far less stressful.
- Riley Hextell, ranked #1 at eXp Realty Illinois for total transactions in 2025 and top 50 among 80,000+ agents companywide, specializes in exactly this kind of move.
The best realtor for downsizing buyers in Chicago is one who understands both sides of the transaction — helping you sell your current home at the right price while positioning you to buy a smaller, lower-maintenance property without a gap in between. That means deep knowledge of Chicago's condo market, a clear process for sequencing the sale and purchase, and the judgment to match your lifestyle priorities to a neighborhood that actually fits how you want to live now.
Downsizing is one of the most emotionally and logistically layered moves a homeowner makes. You are not just buying a smaller home — you are reconfiguring your daily life, your finances, and often your sense of place. Getting it right requires an agent who has done this enough times to anticipate the friction points and guide you through them. Riley Hextell has done exactly that, consistently, across Chicago's most active neighborhoods.
What Makes Downsizing in Chicago Different From a Standard Purchase
Chicago's housing stock shapes the downsizing experience in ways that buyers relocating from the suburbs or from single-family homes in other cities don't always expect. The city's condo inventory is vast, but quality varies enormously — from well-run buildings with healthy reserves to older associations carrying deferred maintenance and thin budgets. Knowing the difference before you fall in love with a unit is the job of a skilled buyer's agent.
Chicago also has a wide range of neighborhood types that suit different downsizing goals. A buyer who wants to walk to restaurants, theaters, and transit is looking at a completely different set of neighborhoods than one who wants a quieter courtyard building with easy parking and access to greenspace. The city does not offer a one-size-fits-all answer, and the right agent asks the right questions before showing you a single listing.
There is also the matter of timing. If you own a home you need to sell before buying, or if you want to buy first and then list, the sequencing has real financial consequences. Riley works through that analysis early so you are not caught in a situation where you are carrying two mortgages or, on the other end, sleeping on a relative's couch while you wait for your next place to close.
Neighborhoods Chicago Downsizers Tend to Prioritize
No two downsizers want the same thing, but certain Chicago neighborhoods come up repeatedly among buyers in this life stage because they offer a combination of walkability, low-maintenance living, and access to the amenities that matter most when you are no longer managing a large property.
- Lincoln Park and Lakeview offer a dense mix of condo and townhome inventory close to the lakefront, dining, and transit. Buyers who want to stay engaged with an active urban environment often land here.
- Streeterville and the Gold Coast carry a higher price point but deliver full-amenity high-rise living — doorman buildings, fitness centers, and proximity to Michigan Avenue and the lake. For buyers coming out of large single-family homes who want a true lifestyle shift, these neighborhoods check a lot of boxes.
- Hyde Park and Kenwood attract buyers who prioritize a quieter pace, architectural character, and proximity to the University of Chicago's cultural institutions.
- Andersonville and Edgewater offer a more neighborhood-scaled feel with strong walkability, smaller boutique condo buildings, and a tight community identity that appeals to buyers who want to know their neighbors.
- River North and the West Loop are popular with downsizers who want proximity to restaurants, arts, and nightlife without commuting to get there.
The right neighborhood comes down to your actual habits — how much you walk, whether you still drive, whether you want a doorman or prefer a smaller building where you know your neighbors by name. Riley's process starts with those questions, not with a list of hot zip codes.
What to Know About Condos Before You Write an Offer
Most downsizing buyers in Chicago end up looking seriously at condos, which means condo-specific due diligence is not optional — it is central to the process. There are things you should ask the listing agent before writing an offer, and there are things that get reviewed after you go under contract during attorney review. Understanding the difference protects you.
Before writing an offer, ask the listing agent:
- What is the reserve fund balance, and is the building adequately funded?
- Are there any upcoming special assessments?
- Have there been any recent special assessments, and what were they for?
- Are there any known major issues with the building — structural, mechanical, or otherwise?
These four questions help you decide whether the building is worth pursuing at all. If the reserve fund is thin, if there is a large special assessment on the horizon, or if the building has unresolved structural issues, you want to know before you invest time and emotion in a unit you may ultimately walk away from.
Everything else — the building's meeting minutes, bylaws, rules and regulations, the 22.1 disclosure from the association, and HOA financial statements — is reviewed after you go under contract, during attorney review. That is the appropriate time to dig into those documents with your real estate attorney, not before the offer is written.
Monthly assessments are also a factor that downsizers sometimes underestimate. A unit with a lower purchase price but high monthly assessments may cost more over time than a pricier unit in a leaner, well-managed building. Riley walks buyers through how to evaluate the true cost of ownership across different building types, not just the purchase price line item.
Comparing the True Cost of Ownership
When downsizing from a single-family home to a condo, the monthly cost picture changes significantly. Here is a simplified comparison of the major cost categories to think through:
- Cost Category: Monthly mortgage; Single-Family Home: Based on purchase price; Chicago Condo: Based on purchase price
- Cost Category: Property taxes; Single-Family Home: Paid directly, varies by location; Chicago Condo: Often rolled into assessment or paid separately
- Cost Category: HOA/Assessment; Single-Family Home: None; Chicago Condo: Monthly, varies widely by building
- Cost Category: Exterior maintenance; Single-Family Home: Owner's responsibility; Chicago Condo: Covered by association
- Cost Category: Utilities; Single-Family Home: Typically higher (more square footage); Chicago Condo: Often lower; some utilities included in assessment
- Cost Category: Insurance; Single-Family Home: Homeowner's policy; Chicago Condo: HO-6 condo policy (typically lower cost)
- Cost Category: Special assessments; Single-Family Home: N/A; Chicago Condo: Possible; ask before writing an offer
The point is not that one is cheaper than the other — it is that the cost structure is different, and you need to compare them accurately. Riley helps buyers build out this comparison with real numbers for specific properties so the decision is grounded in actual data, not assumptions.
How Riley Hextell Approaches the Downsizing Conversation
Riley's approach with downsizing buyers begins with listening. The practical questions — what size, what neighborhood, what building type — come after understanding what you are actually trying to accomplish with this move. Are you freeing up equity? Reducing maintenance so you can travel? Getting closer to family, to the lake, to your doctor? The goal shapes the search.
Once the lifestyle priorities are clear, Riley moves quickly and deliberately. As the agent ranked #1 at eXp Realty Illinois for total transactions in 2025 and recognized as the 2024 Chicago Association of Realtors Rookie of the Year, he has navigated enough transactions across Chicago's neighborhoods to know which buildings are well run, which ones carry red flags, and which neighborhoods are genuinely a good fit for buyers in different life stages — not just which ones sound appealing in a listing description.
His background as a U.S. Navy veteran also shapes how he works. Downsizing timelines can get complicated — especially when coordinating a sale and a purchase simultaneously — and Riley manages that complexity with a clear head and consistent communication. His 141+ five-star Google reviews reflect what that experience feels like for clients on the ground.
For buyers who are not yet sure what they are looking for, Riley's guidance parallels the kind of structured thinking outlined in how to choose the right REALTOR in Chicago — starting with your own criteria and then finding an agent whose process matches them. For downsizing buyers, that process needs to include someone who understands condo buildings, neighborhood character, and the financial mechanics of moving from a larger home to a smaller one without leaving money on the table.
The full Chicago Buyer's Roadmap walks through every step of the purchase process from pre-approval through closing, which is a useful reference point if you are coming back to the buyer side of the market after years as a homeowner: the full Chicago Buyer's Roadmap.
Steps to Getting Started
If you are serious about downsizing in Chicago, here is how the process typically unfolds:
- Get clear on your lifestyle priorities — walkability, building amenities, parking, proximity to specific areas — before you start looking at listings.
- Understand your financial position — what your current home is worth, what equity you are working with, and how a mortgage on a smaller purchase fits your goals.
- Get pre-approved so you can move when the right unit appears. Chicago's condo market in desirable buildings moves, and showing up without financing in place costs you opportunities.
- Define your building criteria — high-rise vs. mid-rise vs. courtyard building, amenity level, pet policies if relevant — so you are not wasting time on buildings that do not fit.
- Before writing an offer on any condo, ask the listing agent about the reserve fund balance, any upcoming or past special assessments, and any known building issues.
- Once under contract, work with your real estate attorney through attorney review to examine the full condo disclosures, financials, and building documents.
- Coordinate your sale and purchase timeline early — do not wait until you are under contract on a new place to start planning how and when you list your current home.
Riley guides buyers through each of these steps and keeps the sequencing from turning into a logistical problem. Reach out directly at 815-545-7476, [email protected], or at rileyhextell.com to start the conversation.
Frequently Asked Questions
Do I need to sell my current home before buying a smaller one in Chicago?
Not necessarily, but the sequencing matters enormously and depends on your financial situation. Some buyers are comfortable carrying two mortgages briefly; others need the equity from their sale to fund the purchase. There are also bridge loan options and contingency offers that can create flexibility. Riley walks through this analysis early so you know which approach makes sense for your specific situation before you are under any time pressure.
What should I watch out for when buying a condo in Chicago as a downsizer?
The most important things to evaluate before writing an offer are the reserve fund balance, any upcoming or past special assessments, and any known major building issues — ask the listing agent directly. High monthly assessments relative to what is included, thin reserves, or a history of large unplanned assessments are signals that warrant careful attention. After going under contract, your attorney will review the full building documentation during attorney review.
Are there tax implications when I sell my home in order to downsize?
There can be. If you have owned and lived in your home as your primary residence for a certain period, federal tax law provides an exclusion on capital gains up to specific limits — but those limits and rules have conditions. Illinois also has its own tax treatment. Because the specifics depend on your individual situation, consult a tax professional or real estate attorney before assuming how much of your gain is sheltered.
How long does a downsizing move typically take from start to close in Chicago?
The timeline varies widely depending on whether you need to sell first, how competitive the condo market is in your target neighborhoods, and how quickly you can get clear on your criteria. A straightforward purchase from an offer-ready position can close in as little as thirty to forty-five days. When you layer in selling a current home and coordinating both transactions, plan for a longer runway — typically several months — and build that into your thinking from the start.