Tax and Timing Advantages to start flipping before 2025 in Chicago can unlock key tax benefits and position your project for maximum return.
URB encourages buyers to start flipping —or at least purchase a property to flip —before year-end to lock in 2025 deductions and potentially defer capital gains through reinvestment strategies like 1031 exchanges, a powerful tax-deferral strategy used in real estate investing. It allows you to sell one investment property and reinvest the proceeds into another without immediately paying capital gains taxes.
In addition, the One Big Beautiful Bill Act signed into law in July 2025, allows real estate investors to benefit from expanded deductions on renovation expenses, interest, and business-related costs.
Start Flipping Before Year-End for Tax Wins Overview
Accelerated Expense Deductions
- Renovation costs—from contractor fees to materials—can often be deducted as business expenses if you operate under an LLC or sole proprietorship.
- Starting in 2025 means you may be able to claim eligible expenses in the same tax year, reducing your taxable income and improving cash flow.
Capital Gains Timing
- If you complete and sell the flip within the same calendar year, you can strategically time your capital gains to align with your broader tax picture.
- For investors planning multiple flips, this allows for year-by-year income smoothing, helping avoid bracket jumps or unexpected tax burdens.
1031 Exchange Prep
- Planning to reinvest profits? Starting now gives you time to prepare for a 1031 exchange, deferring capital gains taxes by rolling proceeds into another investment property. This is especially useful if you’re building a portfolio or scaling your real estate business.
Beat the Winter Slowdown
- Chicago’s real estate market typically slows in late winter, so starting your flip now positions you to list in early spring 2026, when buyer demand rebounds. That means fewer days on market and potentially higher offers.
Secure a Property Fast—Maximize 2025 Tax Benefits
With no credit check financing, a URB Chicago sales representative can help you secure a property quickly—unlocking 2025 tax advantages and boosting your flip’s resale potential.
