Keyser Blog | Commercial Real Estate Advocates

Taxes and CRE: What Business Leaders Need to Know Before Selling

Written by The Keyser Editorial Team | 4:45 PM on December 31, 2025

Taxes and CRE: What Business Leaders Need to Know Before Selling

Selling a commercial property involves more than market timing and pricing strategy. Taxes play a significant role in how proceeds are ultimately realized, making them an important consideration in any commercial disposition discussion.

 

Understanding how commercial real estate taxes may apply at a high level can help business leaders ask better questions, plan earlier, and avoid surprises late in the transaction process.

Why Commercial Real Estate Taxes Matter in a Sale

Taxes can materially impact the net outcome of a commercial property sale. While sale price often receives the most attention, tax treatment can influence:

 

  • Net proceeds received at closing

  • Timing considerations around a sale

  • Strategic decisions such as holding, refinancing, or repositioning

  • Long-term capital planning for the business or ownership group

Because commercial properties are often held for extended periods, tax exposure may be more complex than many business leaders initially expect. This is especially true when ownership decisions intersect with representation models and transaction strategy, as outlined in Keyser’s explanation of tenant representation versus traditional brokerage models in commercial real estate.

 

Common Tax Concepts That May Affect Commercial Property Sales

While every transaction is unique, several tax-related concepts frequently arise in commercial real estate sales.

 

Capital Gains Considerations

When a commercial property sells for more than its adjusted basis, the difference is generally considered a capital gain. The length of ownership and the nature of the ownership entity may influence how gains are treated.

 

Lease structure can also affect income and expense allocation over time, which may influence sale planning. Different commercial real estate lease types distribute operating costs and risk differently throughout the hold period.

Depreciation and Recapture

Commercial properties are typically depreciated over time. Upon sale, a portion of prior depreciation may be subject to recapture, which can be treated differently than other gains. This factor is often overlooked when estimating net sale proceeds.

 

Depreciation is frequently tied to build-out and capital investment decisions made earlier in the lease lifecycle, including tenant improvement allowances and their impact on long-term economics.

State and Local Tax Implications

In addition to federal considerations, state and local tax rules can affect commercial property sales. These rules vary by jurisdiction and may influence overall transaction outcomes.

 

Timing and Tax Awareness in CRE Transactions

The timing of a sale may influence tax exposure. Business leaders often consider:

 

  • Calendar-year versus fiscal-year impacts

  • Alignment with broader business or liquidity planning

  • Market conditions versus long-term holding strategies

In some cases, flexibility strategies during the hold period can affect both operational decisions and future disposition timing. This includes situations where subleasing commercial space is used to preserve flexibility or offset occupancy costs.

 

The Role of Real Estate Strategy in a Tax-Conscious Sale

While tax outcomes are determined by applicable regulations and ownership specifics, real estate strategy plays an important role in positioning a transaction effectively.

 

From a tenant- and owner-advisory perspective, commercial real estate planning often focuses on:

  • Understanding how real estate decisions support broader business objectives

  • Evaluating hold versus sell scenarios at a strategic level

  • Coordinating real estate timing with operational and capital considerations

This alignment allows business leaders to approach potential sales with clearer expectations and stronger positioning.

 

Key Takeaway

Taxes can meaningfully affect commercial property sale outcomes, often in ways that are not immediately visible at the pricing stage. A working understanding of commercial real estate taxes helps business leaders plan earlier, evaluate options more clearly, and navigate potential sales with greater confidence.


 

Disclaimer
This article is for informational purposes only. It does not provide legal, financial, or investment advice. 

Written by the Keyser Editorial Team

 

Frequently Asked Questions 

Q: How do taxes affect the proceeds from selling a commercial property?
A: Taxes can influence the net proceeds received from a commercial property sale by affecting how gains, depreciation, and prior deductions are treated at the time of disposition. While sale price is important, tax treatment can materially impact the final outcome.
Q: Do depreciation and capital gains both apply when selling commercial real estate?
A: In many cases, yes. Commercial properties are often depreciated during ownership, and a sale may involve both capital gain considerations and depreciation recapture. These components are typically evaluated separately and can affect overall tax exposure differently.
Q: Can the timing of a commercial property sale impact taxes?
A: Timing can play a role in how a transaction is treated from a tax perspective. Factors such as the length of ownership, the year of sale, and alignment with broader business planning may influence how commercial real estate taxes apply.