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Case Study

1031 Exchange Case Study: How a DST Transformed a $2.7M Property Into Passive Income

By Stephen HaskellPartner at Anchor1031
Published:August 13, 2025
Updated:August 13, 2025

This 1031 exchange case study details how a retired engineer successfully deferred significant capital gains taxes and transitioned into passive real estate investing.

By leveraging a Delaware Statutory Trust (DST) for his 1031 exchange, he converted a high-value land asset into a diversified, professionally managed portfolio, creating a true 1031 exchange success story.

Key Takeaways

  • Successfully deferred $500K+ in capital gains taxes through strategic 1031 exchange
  • Diversified $2.7M across 20+ properties in 12+ markets with 4 different sponsors
  • Transitioned from active landowner to passive real estate investor
  • Used non-recourse financing to acquire $5.2M worth of property with $2.7M equity

The Challenge: A $2.2M Capital Gains Tax Problem

For decades, a retired engineer held a piece of land he had originally purchased for $500,000. Its value soared to $2.7 million, presenting a fantastic investment return but also a significant tax challenge. Upon selling, he faced a potential capital gains tax bill of over $500,000.

His goals were clear:

  • Defer 100% of the capital gains tax.
  • Avoid the responsibilities of being a hands-on landlord.
  • Generate reliable, passive income for a stress-free retirement.

He needed a solution that was not just tax-efficient, but completely passive. After in-depth consultations with Stephen and Tom from Anchor1031, the perfect strategy emerged: a 1031 exchange into a DST.

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The Solution: A Diversified DST Portfolio

Instead of a single replacement property, the engineer utilized a sophisticated DST diversification strategy. He invested his $2.7 million in proceeds into a portfolio of multiple DSTs, allowing him to gain fractional ownership in a variety of high-quality commercial properties.

This strategy was built on three core pillars:

1. What is a Delaware Statutory Trust (DST)?

A Delaware Statutory Trust (DST) is a legal entity that holds title to one or more investment properties. For a 1031 exchange, investors acquire a "beneficial interest" in the trust, which the IRS recognizes as a like-kind replacement property under Section 1031. This structure allows investors to own a fractional share of large, institutional-grade real estate without direct management duties.

Source: IRS Revenue Ruling 2004-86 established the framework for DST eligibility in 1031 exchanges.

2. Strategic Diversification Across Assets and Markets

The engineer's $2.7 million was spread across a diverse portfolio designed to mitigate risk:

Property Types

20+ different properties including multifamily apartments, industrial warehouses, and essential retail spaces

Geographic Spread

Assets located in 12+ different markets across the United States

Sponsor Diversity

Invested with 4 different, highly vetted sponsor groups

This multi-faceted approach is a cornerstone of a sound DST diversification strategy, protecting capital by not concentrating it in a single asset or market.

Want to see current DST investment opportunities?

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3. Leveraging Debt to Enhance Returns and Meet Exchange Requirements

A key advantage of the Delaware Statutory Trust 1031 structure is its use of pre-arranged, non-recourse financing. The engineer's $2.7 million in equity was used to acquire $5.2 million worth of property, satisfying his 1031 exchange requirement to replace both equity and debt.

Benefits of this built-in leverage include:

  • No Personal Loan Guarantees: The debt was secured by the properties themselves, with no personal liability for the engineer.
  • Increased Depreciation: The leveraged portion of the acquisition increased his potential for depreciation deductions, which can help shelter income from taxes.
  • Simplified Exchange: He avoided the complex and time-consuming process of applying for his own loans within the tight 45-day identification window of a 1031 exchange.

The Outcome: Peace of Mind and Passive Real Estate Investing

By working with Stephen and Tom at Anchor1031, the retired engineer achieved all his goals:

Tax Savings

Successfully deferred 100% of his capital gains taxes

Passive Income

Transitioned from active landowner to passive real estate investor

His wealth is now professionally managed, aligned with his goals for a hands-free retirement, and structured for long-term, tax-efficient growth.

Considering a similar strategy for your property?

Download our free 1031 Exchange Guide to learn how to defer taxes while transitioning to passive real estate investing.

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Frequently Asked Questions

Ready to Start Your 1031 Exchange Journey?

If this case study resonates with your investment goals, Anchor1031's team of specialists can help you navigate your own tax-deferral strategy. With over $1B+ in real estate syndications and 300+ completed 1031 transactions, we provide the professional knowledge and support you need for a successful exchange.

Don't let capital gains taxes erode your wealth. Contact Anchor1031 at (502) 556-1031 to discover how a 1031 exchange can help you build lasting wealth through passive real estate investing.

Stephen Haskell

Stephen Haskell

Partner at Anchor1031

Stephen Haskell is a partner at Anchor1031, bringing a unique perspective to real estate investment through his distinguished military background. With a career managing intelligence operations for elite special missions units in Afghanistan, Iraq, and Africa, Stephen developed critical expertise in strategic planning and risk mitigation - skills that were literally a matter of life or death.

Transitioning to the real estate industry, Stephen identified a critical flaw: a relaxed, unbalanced approach to risk management. For investors looking to retire, he recognized that an overlooked risk could compromise a lifetime of hard-earned wealth. This realization became the foundation of Anchor1031, where Stephen applies the same meticulous approach to risk assessment that he used in military operations.

Anchor1031's primary objective is to identify risk, educate clients on its potential impact, and build portfolios based on transparency and integrity. Stephen's military-grade discipline in strategic planning now protects investors' wealth through carefully vetted 1031 exchanges and DST investments.

Disclosure

Tax Complexity and Investment Risk

Tax laws and regulations, including but not limited to Internal Revenue Code Section 1031, bonus depreciation rules, cost segregation studies, and other tax strategies, contain complex concepts that may vary depending on individual circumstances. Tax consequences related to real estate investments, depreciation benefits, and other tax strategies discussed herein may vary significantly based on each investor's specific situation and current tax legislation. Anchor1031, LLC and Great Point Capital, LLC make no representation or warranty of any kind with respect to the tax consequences of your investment or that the IRS will not challenge any such treatment. You should consult with and rely on your own tax advisor about all tax aspects with respect to your particular circumstances. Please note that Anchor1031 and Great Point Capital, LLC do not provide tax advice.

Anchor1031

The information contained in this article is for general educational purposes only and does not constitute legal, tax, investment, or financial advice. This content is not a recommendation or offer to buy or sell securities. The content is provided as general information and should not be relied upon as a substitute for professional consultation with qualified legal, tax, or financial advisors.

Tax laws, regulations, and IRS guidance regarding 1031 exchanges are complex and subject to change. Information herein may include forward-looking statements, hypothetical information, calculations, or financial estimates that are inherently uncertain. Past performance is never indicative of future performance. The information presented may not reflect the most current legal developments, regulatory changes, or interpretations. Individual circumstances vary significantly, and strategies that may be appropriate for one investor may not be suitable for another.

All real estate investments, including 1031 exchanges, are speculative and involve substantial risk. There can be no assurance that any investor will not suffer significant losses, and a loss of part or all of the principal value may occur. Before making any investment decisions or implementing any 1031 exchange strategies, readers should consult with their own qualified legal, tax, and financial professionals who can provide advice tailored to their specific circumstances. Prospective investors should not proceed unless they can readily bear the consequences of potential losses.

While the author is a partner at Anchor1031, the views expressed are educational in nature and do not guarantee any particular outcome or create any obligations on behalf of the firm or author. Neither Anchor1031 nor the author assumes any liability for actions taken based on the information provided herein.