Most homeowners treat buying and selling as a sequence problem: sell first, then buy. It's the path of least resistance, the one that feels safest. But for homeowners who've spent months or years waiting for the right property—the layout that works, the neighborhood that fits, the timeline that makes sense—finding that home creates a different kind of pressure.
The question becomes: do you let it go because your current house hasn't sold yet?
For some Chicago homeowners—those with equity, stable income, and a clear-eyed view of their finances—carrying two mortgages isn't a gamble. It's a strategic position with known costs and explicit exit strategies. For others, it's the wrong move entirely.
This article isn't about convincing you to buy before selling. It's about helping you understand what the strategy actually costs, who it tends to work for, and how to evaluate whether it fits your situation.
What You're Actually Paying For: The C-A-R-E Framework
The real cost of carrying two properties isn't just the mortgage payment. It's what we call the daily burn rate—the sum of everything required to keep both properties operational and protected while you're between homes.
Core Costs
These are your baseline obligations: principal, interest, taxes, and insurance on both properties. In Chicago, this calculation gets particular attention because of property taxes. Cook County's effective property tax rate runs around 1.89% to 2.3%—roughly double the national average. On a $365,000 home, you're looking at approximately $6,800 to $8,400 annually in property taxes alone, or about $567 to $700 per month.
For a homeowner carrying two mortgages in Chicago, this tax burden matters. It's not a variable you can negotiate down in the short term, and it doesn't pause while your house sits on the market. When you calculate your monthly burn rate, property taxes often represent a larger percentage of your total cost than they would in other markets.
Additional Maintenance
An empty house deteriorates faster than an occupied one, and it shows. Lawns grow, gutters fill, walkways develop ice in winter. In Chicago, where winters are harsh and curb appeal matters year-round, an unmaintained property signals distress to potential buyers.
Snow removal alone becomes a line item you can't ignore. If your property isn't being cleared after snowfall, you're not just risking a code violation—you're broadcasting that the house is vacant. The same applies to lawn care, basic landscaping, and ensuring the exterior looks actively managed.
Budget for regular visits or hire someone to handle it. The cost is modest compared to the impact on showing potential.
Recurring Utilities
You can't shut off the heat. In Chicago's climate, turning utilities off entirely in an empty house risks frozen pipes, water damage, and insurance complications that can cost tens of thousands to remediate.
Keep the heat set to a minimum safe temperature (typically 55°F), maintain water service to prevent pipe issues, and run occasional checks on HVAC systems. These aren't optional—they're structural requirements of maintaining the asset.
Extras
This is where homeowners often get caught off guard. If your property is part of an HOA, those dues don't stop. If you're in a condo building, assessments continue.
More critically: standard homeowner's insurance often excludes coverage for vacant properties after 30 to 60 days. If your house is empty and something happens—a break-in, a pipe bursts, storm damage—you may discover your claim is denied because the property wasn't continuously occupied.
Vacant home insurance exists specifically for this scenario. It costs more than standard coverage, but it protects the asset during the transition period. This isn't paranoia; it's cost of doing business when you're carrying two properties.
What the Lender Actually Requires: Reserves as a Safety Mechanism
When you apply for a mortgage on your new home while still owning your current one, most lenders will require you to demonstrate liquidity—typically six months of cash reserves covering both mortgages, plus taxes and insurance.
This isn't arbitrary. It's the lender's way of ensuring you can sustain both properties if your existing house takes longer to sell than expected. They're not asking if you can make the first payment; they're asking if you can handle a 90- to 180-day carrying period without financial distress.
If you don't have this cushion, you won't clear underwriting. If you do have it, the lender views you as a manageable risk. This reserve requirement also serves as a useful self-assessment tool: if you're uncomfortable holding that much liquidity in accessible accounts, carrying two mortgages may not align with your risk tolerance.
The Recasting Option: Lowering Your Payment Without Refinancing
One of the most underutilized tools in this strategy is mortgage recasting. Here's how it works:
You buy your new home with a smaller down payment—say 10% or 15%—to preserve liquidity while your current house is on the market. Once your existing home sells, you take the proceeds and make a lump-sum principal payment on the new mortgage. The lender then re-amortizes the loan over the remaining term at the same interest rate, which lowers your monthly payment without requiring a refinance.
This is different from refinancing. You're not applying for a new loan, paying closing costs, or re-qualifying. You're simply paying down the balance and asking the lender to recalculate the payment schedule. Most lenders charge a small administrative fee—often a few hundred dollars—and the process takes a few weeks.
Recasting gives you flexibility. You're not locked into a large down payment on the new house before you have certainty on the sale of the old one, but you're also not stuck with a permanently higher monthly obligation once you do sell.
Not all loan products allow recasting (FHA and VA loans typically don't), so confirm this option with your lender before structuring your purchase this way.
Exit Strategies: What Happens If the House Doesn't Sell
Carrying two mortgages works when there's a plan. But plans don't always execute on schedule. In Chicago's current market, where homes are averaging 67 days on market, most properties do sell within a reasonable timeframe—but not all of them.
If you're at 90 days and the house hasn't moved, you have options. None of them are pleasant, but all of them are manageable if you've structured the situation correctly from the beginning.
Bridge Financing
Some lenders offer short-term bridge loans that let you tap equity in your existing home to cover carrying costs or make a larger down payment on the new property. These loans are expensive—higher interest rates, short terms, fees—but they can buy you time if you're confident the sale will happen and you just need a few more months of runway.
Bridge loans aren't for everyone. They add another layer of debt and cost, and they assume the market will cooperate. But for homeowners with strong equity positions and clear timelines, they can smooth the transition.
The Rental Pivot
If your existing home isn't selling and you're financially stable enough to hold both properties longer-term, converting it to a rental is an option. This changes the entire calculation—you're no longer just covering costs, you're generating income.
Chicago's rental market has held relatively steady, and in many neighborhoods, rental demand remains strong. If the numbers work—if rent covers or nearly covers your mortgage, taxes, insurance, and management costs—this can shift from a short-term problem to a long-term asset.
This requires a different mindset. You're now a landlord, which brings tenant management, maintenance obligations, and tax implications. But it's a legitimate exit strategy if the alternative is selling at a loss or continuing to burn cash on an empty property.
Strategic Price Adjustment
The simplest lever is price. If the market isn't responding, the price isn't right. This is emotionally difficult for many homeowners—it feels like a concession, a loss—but it's often the most direct path to resolution.
Set a decision point in advance. If the house hasn't sold in 90 days, you drop the price by X%. If it hasn't sold in 120 days, you drop it again. Remove the emotion from the decision by making it a mechanical response to market feedback.
Chicago's market has shown steady appreciation—median prices are up around 4-5% year-over-year—but individual properties don't move on market trends. They move on how they're priced relative to current buyer demand in that specific neighborhood at that specific moment.
Who This Strategy Actually Fits
This approach works for a specific type of situation. Not a specific type of person—a specific type of situation.
It tends to make sense when:
You have meaningful equity in your current home—typically at least 20-30%—which gives you financial cushion and makes lenders more comfortable.
Your income is stable and high enough to qualify for both mortgages simultaneously without straining your debt-to-income ratio.
You have cash reserves that meet or exceed the lender's requirements (usually six months of combined housing costs), and you're genuinely comfortable holding that much liquidity in accessible accounts rather than investing it elsewhere.
You've found a property that represents a real opportunity cost if you lose it—not just any house, but one that genuinely fits your needs in ways that would be difficult or time-consuming to replicate.
You understand your carrying costs down to the monthly dollar amount and have a realistic sense of how long you can sustain them based on your actual spending patterns, not optimistic projections.
You have explicit exit strategies and predetermined decision points if the sale takes longer than expected, and you're willing to execute them without letting emotion override the plan.
If several of those conditions aren't true for you, this strategy probably isn't the right fit. And that's fine. Knowing what doesn't work for your situation is just as valuable as knowing what does.
The goal isn't to make this work. The goal is to make the right decision for your circumstances.
The Chicago Context: What Makes This Market Different
Chicago's real estate market carries a few specific considerations that affect this calculation.
First, property taxes. Cook County's tax burden is notably higher than most U.S. markets. Recent data shows the median Chicago homeowner saw tax bills jump 16.7% in 2025—the largest single-year increase in decades. While there's no broad property tax increase planned for 2026, individual assessments continue to shift based on neighborhood dynamics and reassessment cycles.
For homeowners carrying two properties, this means your monthly carrying costs in Chicago are structurally higher than they'd be in many other cities. It's not a reason to avoid the strategy, but it's a reason to be precise about your math.
Second, seasonality. Chicago's housing market slows notably in winter. Inventory tightens, buyer activity drops, and days on market extend. If you're planning to carry two mortgages and your existing home is going on the market in November, understand that you're likely looking at a longer timeline than if you listed in April.
This doesn't mean you can't execute the strategy in winter—plenty of homes sell year-round—but it means your carrying period assumptions need to account for seasonal patterns.
Third, inventory remains relatively tight. As of early 2026, Chicago's housing supply is still below historical norms despite recent increases. For buyers, this creates competition. For sellers, it means well-priced, well-maintained properties in desirable neighborhoods are still moving.
If your existing home is in a strong location, properly staged, and priced in line with recent comps, the odds of a reasonable sale timeline are in your favor. If it's in a softer market or needs work, the calculus changes.
What This Looks Like in Practice
Let's say you're a Chicago homeowner with a house currently worth $400,000. You owe $200,000 on your mortgage. You've found a new home listed at $500,000.
You qualify for a mortgage on the new property with 15% down ($75,000) while still carrying your existing mortgage. Your lender requires six months of reserves covering both properties—call it $30,000 in liquid savings.
You make the offer, go under contract, and close on the new house. Your old house goes on the market immediately.
Your carrying costs on the old property: $1,200/month mortgage, $650/month property taxes, $150/month insurance, $100/month utilities, $200/month lawn and snow service. Total: $2,300/month.
Your new mortgage runs $2,800/month including taxes and insurance.
Combined monthly burn: $5,100.
You budget for 90 days of carrying time. If the old house sells in 60 days, you're out $13,800 in total carrying costs (minus whatever equity you recover). If it sells in 90 days, you're at $20,700.
Once it sells, you net roughly $200,000 in proceeds (minus closing costs and remaining carrying costs). You take $150,000 of that and recast your new mortgage, which drops your payment from $2,800 to around $2,100.
You've successfully moved into your preferred home without losing it to another buyer, you've managed a defined carrying period, and you've optimized your long-term payment structure.
This is what the strategy looks like when it works. It's not effortless, but it's structured.
Final Considerations
The question isn't whether carrying two mortgages is good or bad. The question is whether it fits your situation.
For some homeowners—those with the financial foundation, clear understanding of costs, and explicit exit strategies—it's a legitimate way to secure the home they want without being held hostage by timing.
For others, it introduces unnecessary risk or doesn't align with their financial structure, risk tolerance, or life circumstances. And that's equally valid.
The value isn't in the strategy itself. It's in understanding what the strategy actually requires and whether those requirements match your reality.
If you have meaningful equity, stable income, substantial reserves, and a property worth securing—and you're comfortable with the carrying costs and have clear decision points if things don't go as planned—this approach is worth considering.
If several of those pieces aren't in place, or if the idea of holding that much liquidity in cash makes you uncomfortable, that tells you something important about fit.
The right answer is the one that matches your numbers, your risk tolerance, and your actual circumstances—not the one that sounds appealing in theory.
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This article provides general information about real estate strategies and is not intended as financial, legal, or tax advice. Individual circumstances vary significantly. Consult with qualified financial advisors, mortgage professionals, and legal counsel before making decisions about carrying multiple mortgages or real estate transactions. All Chicago market data referenced is current as of February 2026 and subject to change.
