Services · Sterling Foundations & Trusts

Real Estate Shelter Trusts

Sell your appreciated property—no capital gains tax, no depreciation recapture at the trust level. Reinvest the full proceeds in a diversified portfolio and eliminate the headaches of active management forever.

The Problem

Appreciated Property Is Both an Asset and a Trap.

Long-term real estate owners face a double tax burden on sale: capital gains on appreciation plus depreciation recapture taxed at 25%—before the 3.8% net investment income surtax. In high-tax states, the combined rate can approach 40% or more. A 1031 exchange defers the problem without solving it, and keeps you concentrated in real estate.

A §664 Real Estate Shelter Trust eliminates the tax entirely at the trust level. Contribute your property, and the trust sells it—keeping 100% of the proceeds to reinvest in any diversified portfolio your advisor selects.

  • No capital gains tax—none—at the trust level on the sale
  • No depreciation recapture at the trust level
  • Income tax deduction of at least 10% of contributed value upon funding
  • Proceeds reinvested in a diversified portfolio—not another property
  • Eliminates management hassles, tenant risk, and concentrated real estate exposure
  • Income for you, your spouse, children, and grandchildren
  • Asset protection; tax-deferred compounding for 50–60 years
0%
Capital gains tax at the trust level—including zero depreciation recapture
≥10%
Upfront income tax deduction as a percentage of property fair market value
100%
Of sale proceeds available to reinvest—not the 60–70% left after tax
50–60
Years of tax-deferred growth for you and multiple generations
Testimonial
Antonia Buban
Antonia Buban
Client
Sterling Foundations & Trusts

“As far as Assets Under Management [growth] is concerned… to give you a number: close to 30 million.”

Antonia Buban
Founder, Buban Financial Services
How It Works

From Concentrated Real Estate to Diversified Wealth in Four Steps.

1

Establish the Trust

Sterling and your legal advisors create a §664 charitable remainder trust. You name yourself and chosen family members as income beneficiaries over a 50–60 year term.

2

Contribute the Property

The real estate is transferred to the trust. The transfer itself does not trigger a taxable event. Any existing debt on the property is addressed in the structuring process.

3

The Trust Sells—Tax-Free

Because the trust is tax-exempt under §664, it sells the property and retains 100% of the proceeds. There is no capital gains tax and no depreciation recapture at the trust level.

4

Invest and Receive Income

Your financial advisor invests the full proceeds in an appropriate portfolio. You may take regular distributions or defer them for continued tax-deferred compounding.

Case Study · Appreciated Real Estate

$4 Million Apartment Building—$1.42 Million in Tax Savings.

Case Study #103 · Appreciated Real Estate

Bob’s Situation

Bob is a widower, age 79, with three adult children. He owns a 12-unit San Diego apartment building worth $4,000,000 with a basis of $180,000. Selling outright would cost $1,417,220 in combined capital gains and recapture taxes, leaving only $2,582,780. Sterling recommended three Real Estate Shelter Trusts—one for each child to receive income after Bob’s lifetime.

Capital Gains & Recapture Savings
$1,417,220 in combined tax savings
Full Proceeds to Invest
$4,000,000 reinvested (vs. $2,582,780 after tax)
Net Spendable Income
2× expected income vs. outright sale over trust term
Income Tax Deduction
$400,000 deduction in year of funding
Risk Eliminated
No longer bears risk of single-property ownership
Legacy for Three Children
Each child receives income from their own trust for life
Key Benefits

Why Real Estate Owners Choose This Strategy.

🏠

No Depreciation Recapture

Unlike a direct sale or 1031 exchange, the trust pays no depreciation recapture tax—eliminating one of the most significant hidden costs of selling long-held real estate.

🔄

True Diversification

Proceeds can be reinvested in virtually any asset class your advisor selects—not another property. You finally achieve the diversification a 1031 exchange can never deliver.

😌

Eliminate Management Burden

No more tenants, maintenance, vacancies, or liability exposure. Convert an active, illiquid asset into a professionally managed, diversified portfolio.

👨‍👩‍👧‍👦

Multi-Generational Income

Structure the trust to provide income for yourself, your spouse, and your children and grandchildren over a 50–60 year term—creating a lasting family legacy.

🔒

Asset Protection

Spendthrift provisions protect trust assets from creditor claims—giving you and your beneficiaries an added layer of security beyond the diversification itself.

📋

Better Than a 1031 Exchange

A 1031 exchange defers tax but keeps you concentrated in real estate. A Real Estate Shelter Trust eliminates the tax and lets you diversify into any investment your advisor recommends.

Comparing Your Options

Four Strategies for Selling Appreciated Property

Long-term real estate owners often face taxable gains from both increases in market value and depreciation recapture, which is taxed at 25% plus the 3.8% surtax. Here is how the four common strategies compare.

Straightforward but costly

Outright Sale

Sell the property and reinvest the after-tax proceeds. Simple and provides complete liquidity.

  • Capital gains tax of up to 30–40% (including depreciation recapture at 25% + 3.8% surtax)
  • In high-tax states, the combined effective rate can approach 40% or more
  • No asset protection; no income for children or grandchildren
Defers but doesn’t eliminate

1031 Exchange

Exchange into a like-kind property to defer capital gains tax.

  • Strict timelines; failure to complete can trigger full tax
  • Triple-net leases carry concentrated credit risk, interest rate risk, and selective lease rejection risk under §502(b)(6) of the Bankruptcy Code
  • Does not achieve diversification—you remain concentrated in real estate
  • Depreciation recapture and gain still owed eventually
Modest savings, counterparty risk

Installment Sale

Sell for a combination of cash and a qualifying note under §453, spreading gain realization over multiple years.

  • Only capital assets qualify; recapture may be taxed in year of sale regardless
  • Interest on note taxed at ordinary rates (~40.8% federal)
  • Seller becomes a creditor of the buyer
  • Risk that tax rates increase in future years
Tax-exempt · Diversified · Multigenerational

Real Estate Shelter Trust (§664)

A tax-exempt trust under §664. Contributions of appreciated real estate are tax-free, and the trust sells the property with no capital gains tax and no depreciation recapture at the trust level.

  • No capital gains tax; no recapture at the trust level
  • Income tax deduction of at least 10% of contributed value
  • Proceeds reinvested in a diversified portfolio—not another property
  • Eliminates management hassles and concentrated real estate risk
  • Income for the contributor, spouse, children, and grandchildren
  • Asset protection; tax-deferred compounding for 50–60 years

See the full side-by-side comparison: Comparing Your Options →

Ready to Sell Without the Tax Bill?

Sterling has helped property owners across the country convert decades of appreciation into lasting, diversified income streams. Schedule a conversation to explore your options.

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