How to Rollover a SIMPLE IRA to a Real Estate IRA

01Executive Overview

02Eligibility Rules

Before initiating a SIMPLE IRA–to–Real Estate IRA rollover, confirm that both the source plan and the destination account meet IRS eligibility requirements.

SIMPLE IRAs are available only through employers with 100 or fewer employees who earned at least $5,000 in the preceding year. Employees are generally eligible if they earned at least $5,000 in any 2 preceding years and are expected to earn at least $5,000 in the current year. The plan must cover all eligible employees — employers cannot exclude eligible workers.

— IRS Publication 560 (Retirement Plans for Small Business)

03Step-by-Step Rollover Process

The IRS-preferred rollover method is a direct rollover (trustee-to-trustee transfer) — the check is made payable to the new custodian, not to you. This eliminates the mandatory 20% federal withholding and the 60-day deadline risk entirely.

1. 1

   Open the Real Estate IRA Account First

   Open the receiving Real Estate IRA account before contacting your SIMPLE IRA plan administrator. The distributing plan needs the receiving custodian's name, mailing address, and FBO account number to process a direct rollover. Without this information, the plan cannot complete the direct rollover and may default to an indirect rollover.

   Setup time: 10–21 business days from rollover to first real estate purchase closing

   You'll need:

   • Government-issued ID
   • SSN
   • SDIRA application
   • Rollover or transfer from existing retirement account
   • Selected property and purchase contract (for initial investment)
   • Sufficient cash reserve within the IRA for property expenses

   Select an IRS-approved SDIRA custodian (e.g., Equity Trust, Directed IRA, IRA Financial). Verify the custodian is chartered under IRC Section 408(a) before opening.
2. 2

   Request a Direct Rollover from Your SIMPLE IRA

   Contact your SIMPLE IRA plan administrator and use the words "direct rollover" explicitly. Provide:

   • The receiving custodian's full legal name
   • The FBO format: [Custodian Name] FBO [Your Full Name] Real Estate IRA
   • The receiving account number
   • The custodian's mailing address

   After the 2-year participation period, SIMPLE IRA assets roll via standard trustee-to-trustee transfer or 60-day rollover to a traditional IRA, just like any other IRA. During the 2-year period, the only permissible transfer is from one SIMPLE IRA to another SIMPLE IRA.

3. 3

   Verify the Check Payee

   When the distribution check arrives — whether mailed to you for forwarding or directly to the custodian — verify the payee before accepting or forwarding it. The check must be payable to the new custodian, not to you personally.

   ✓ Correct

   Fidelity FBO Jane Smith IRA #123456789

   ✗ Incorrect (Triggers 20% Withholding)

   Jane Smith

   If the check is made payable to you personally, contact the plan administrator immediately. Do not deposit it into a personal bank account — doing so converts it into an indirect rollover subject to 20% withholding and the 60-day deadline.

4. 4

   Deposit as a Rollover Contribution

   When delivering the check or wire to the receiving custodian, specify it as a "rollover contribution" — not a regular annual IRA contribution. This critical coding ensures the amount is not counted against your 2026 IRA contribution limit (standard annual limits).

   Open the Real Estate SDIRA account, fund via direct rollover, identify the target property, have the SDIRA custodian review the purchase contract, submit an Investment Direction Letter authorizing the purchase, and the custodian takes title in the IRA's name (e.g., 'Equity Trust Company FBO John Smith IRA'). All earnest money and closing costs must come from within the IRA.

   Posting time after receipt: Varies by property transaction. Residential closings: 14–30 days after purchase contract. Cash closes: faster. All-cash Real Estate IRA purchases avoid the non-recourse financing complexity.
5. 5

   Submit an Investment Direction Letter

   Once the cash is credited to your SDIRA, the custodian holds funds in your account but does not invest them automatically. You must submit an Investment Direction Letter (IDL) authorizing the specific alternative asset purchase.

   The SDIRA custodian takes legal title to the property on behalf of the IRA. All documents — deeds, purchase contracts, leases, management agreements — must identify the IRA as the owner (not the account holder personally). The custodian must approve all transactions in writing through a formal investment direction process.

   🔴

   Real Estate Title Vesting: All purchase documents, deeds, and closing paperwork must identify the IRA, not you personally, as the buyer. Example: Equity Trust Company Custodian FBO Jane Smith IRA. Using your personal name on the deed is a prohibited transaction that disqualifies the entire IRA.
6. 6

   Confirm Tax Documentation

   In January of the following year, verify you receive:

   • Form 1099-R from the SIMPLE IRA plan — shows the gross distribution with Distribution Code G (direct rollover). Report on Form 1040 Line 5a with $0 on Line 5b — write 'ROLLOVER' on the dotted line.
   • Form 5498 from the receiving Real Estate IRA custodian — issued by May 31, confirms the rollover contribution was received and properly coded.

04Processing Timeline

Most SIMPLE IRA–to–Real Estate IRA rollovers complete in 10–21 business days from request submission to funds credited at the receiving institution. The timeline varies significantly by plan administrator and asset type.

05Tax & Penalty Guide

SIMPLE IRAs are most commonly found in small businesses — restaurants, retail shops, medical practices, and professional service firms with under 50 employees. Many employees of small businesses are unaware of the 2-year restriction at the time of their hiring, making it a significant surprise upon departure within the first two years.

06IRS Reporting Requirements

Every retirement account rollover — including non-taxable direct rollovers — requires reporting on your federal tax return. Failing to report a rollover, even a tax-free one, triggers the IRS's Automated Underreporter (AUR) program to propose tax on the full distribution amount.

07Custodian & Compliance Rules

The Real Estate IRA requires an IRS-approved self-directed IRA custodian and strict compliance with IRC Section 4975 prohibited transaction rules. The custodian takes legal title to the assets — the account holder never holds them personally.

083 Costly Mistakes to Avoid

These are the most common — and most expensive — errors investors make when rolling over a SIMPLE IRA to a Real Estate IRA. Each is preventable with the right procedural knowledge.

09Frequently Asked Questions

What is the SIMPLE IRA 2-year rule?

The 2-year rule prohibits rolling SIMPLE IRA assets to a traditional IRA, Roth IRA, or qualified plan within the first 2 years of plan participation. If you take a distribution during this period and do not roll it to another SIMPLE IRA, the distribution is subject to a 25% early withdrawal penalty — not the standard 10%. The 2-year period starts when the first employer contribution is made to the account.

Can I roll over my SIMPLE IRA when I leave my job?

Yes — if you have participated in the SIMPLE IRA for at least 2 years, you can roll over to a traditional IRA, Roth IRA (as a conversion), or qualified plan (if the plan accepts rollovers). If you have been in the plan for less than 2 years, you can only transfer to another SIMPLE IRA. Rolling to any other account type before the 2-year period triggers the 25% penalty.

What happens to my SIMPLE IRA if my employer switches to a 401(k)?

An employer cannot terminate a SIMPLE IRA plan and establish a 401(k) in the same calendar year. The SIMPLE IRA must be terminated effective December 31, with employees notified by November 2 of that year. In the following year, the employer can establish a 401(k). At termination, employees can roll their SIMPLE IRA balances to an IRA (subject to the 2-year rule) or leave them in the account as a traditional IRA.

Can I use my IRA to buy a rental property?

Yes — a self-directed IRA (Real Estate IRA) can purchase rental properties. The IRA takes legal title to the property, and all rental income flows back into the IRA tax-deferred (or tax-free in a Roth SDIRA). The key restrictions are: you cannot personally use the property, family members cannot use or live in it, and all expenses must be paid from within the IRA.

Can I buy a house with my IRA for my child to live in?

No. Renting an IRA-owned property to your child (or any other 'disqualified person' — including your spouse, parents, grandchildren, or entities you control) is a prohibited transaction under IRC Section 4975. The consequence is that the entire IRA is deemed distributed as of January 1 of the violation year, making the full balance immediately taxable.

What happens to a Real Estate IRA when I reach RMD age at 73?

You must take Required Minimum Distributions from the IRA, including from the value of the real estate. Since you cannot distribute a fraction of a property, you have three options: (1) maintain sufficient cash in the IRA to cover the annual RMD; (2) take an in-kind distribution of a partial property interest (complex and taxable); or (3) sell the property before RMD age and hold the proceeds in cash for distribution. Proactive RMD planning for Real Estate IRAs should begin at least 5 years before age 73.

Is there a deadline to roll over a SIMPLE IRA after leaving my employer?

There is no IRS deadline to initiate a rollover after a triggering event. The 60-day rule only applies once a distribution has been issued to you. However, plan administrators may force distributions for balances under $7,000 within 12–18 months of separation. Address the rollover within 60–90 days to maintain administrative control.

Does a direct rollover count against my annual IRA contribution limit?

No. Rollover contributions are separate from and do not count against the annual IRA contribution limit ($7,000 in 2026; $8,000 for those age 50+). A $400,000 rollover into a Real Estate IRA does not affect your ability to make a regular annual contribution to the same account.