Real Estate Tax Advisory & Planning

Forward-looking tax strategy built around real estate and revisited throughout the year, so major moves are planned before they happen.

What This Is

Tax planning for real estate works best when it happens throughout the year. We work with investors, syndicators, fund managers, and developers to structure acquisitions, sales, and refinances with the tax consequences in mind before transactions close. The goal is to make major decisions with a clear view of the tax impact, not to scramble in April trying to reduce a bill that was already locked in months ago.

The firm’s in-house CPA handles the technical tax analysis and modeling. Matthew leads the relationship and coordinates the planning, making sure tax is part of the conversation before every major decision. This is strategy work, separate from but connected to the tax return preparation service we also provide.

Planning Around Your Deal Timeline

We schedule planning conversations before you acquire, before you sell, before you refinance, and before year-end. Quarterly estimated-tax reviews keep your payments aligned with what is actually happening in your portfolio, so there are no surprises when you file. The cadence follows your deals, not the IRS calendar.

Real Estate Tax Strategies

Cost segregation and bonus depreciation to accelerate deductions on acquisitions. 1031 exchange planning and coordination with qualified intermediaries. Real estate professional status analysis. Short-term rental structuring for operators whose participation makes losses non-passive and available to offset ordinary income. Section 199A and QBI optimization. Opportunity Zone guidance. Depreciation recapture modeling, installment sales, and exchange timing before dispositions. Estate and gift planning coordination with your attorney when ownership transitions are on the horizon.

Why This Matters

Most tax conversations happen after the fact. You close a deal, then calculate what you owe. You sell a property, then wonder if there was a better way to structure it. By that point, the significant decisions are locked in. Election deadlines have passed. The deductions you could have captured are gone. The exchange you could have completed is no longer available.

Real estate creates substantial tax consequences, and those consequences depend on choices made during the deal. How the entity is structured. When the sale closes. Whether to pursue an exchange or take the cash. How the purchase price gets allocated. All of these shape the outcome, and all of them happen before tax season.

Timing Makes the Difference

A sale that closes in December has a different tax profile than one that closes in January. A short-term rental operated with sufficient participation generates losses that offset W-2 income. A cost segregation study ordered during acquisition captures more value than one requested years later. The numbers change based on when and how decisions get made.

Quarterly Projections Keep You Current

Estimated tax payments should reflect your actual activity, not last year’s numbers rolled forward. We review each quarter, adjust for acquisitions and dispositions that have closed, and calculate payments that match what is really happening. When April comes, the balance is what you expected because the projections stayed current all year.

What Changes

When tax planning is woven into how you operate, every significant transaction gets evaluated with the full picture. Before you buy, you know whether cost segregation makes sense and what the accelerated depreciation will generate. Before you sell, you have a model showing recapture, installment options, and exchange timing. Before year-end, you know where you stand and what moves are still available.

The firm handles bookkeeping, tax planning, and return preparation under one roof. The same in-house CPA who prepares your returns is involved in modeling the strategies throughout the year. When filing time arrives, the numbers tie out because the planning was coordinated from the start.

Deals Structured with Tax in Mind

Acquisitions get evaluated for cost segregation potential, entity structure, and basis allocation. Dispositions get modeled for recapture, installment treatment, and exchange feasibility. Refinances get reviewed for their impact on debt and basis. The analysis happens while there is still time to adjust the approach.

One Firm from Planning to Filing

Tax planning feeds directly into your bookkeeping and return preparation. Your depreciation schedules, capital accounts, and entity records are built with the strategy in mind. When we prepare your returns, everything is already aligned because the same team handled it throughout the year. No handoffs between firms and no scrambling to reconstruct decisions made months earlier.

Boutique Real Estate Accounting Firm