For Florida Accredited Investors Selling Investment Property in 2026
Defer Every Dollar of Federal Capital Gains Tax Without Wasting Florida's Biggest Advantage on the Wrong Replacement Property
Florida investors have no state income tax to worry about. That means a 1031 exchange here is purely about getting the federal deferral right, and putting that capital into the best possible asset. Most investors focus on completing the exchange. The ones who build real wealth focus on completing it into the right property. Even if you have already spoken to a DST sponsor and have a property in mind.
As Featured In
The Florida Opportunity
You Already Have the Best Tax Environment in the Country. Here Is How to Use It.
Florida has no state income tax. On a $500K gain, that means $119,000 in federal tax without a 1031 exchange. With a properly executed 1031 exchange, the immediate tax is zero and the full $500,000 stays invested.
No clawback provision. No withholding forms. No annual state filings. There are no state-specific requirements for a 1031 exchange in Florida. The federal rules apply cleanly and completely.
That simplicity is an advantage. It is also a trap. Investors who mistake a clean exchange for a good one.
A technically valid exchange into a weaker asset can be worse than a taxable sale. Investors who overvalue current deferral often undervalue optionality. In Florida's market, where appreciation has been strong and replacement options are plentiful, the real risk is not failing the exchange on a technicality. The real risk is completing it into the wrong property under deadline pressure.
Breakwater exists to prevent that.
The Problem Florida Investors Actually Face
Three Ways a Perfectly Valid Exchange Still Goes Wrong
The 45-Day Scramble Into Whatever Is Available
Deadline pressure converts a strategic decision into a reactive one.
Florida's market moves fast. Investors who start building their replacement shortlist after closing face a narrowing window and a shrinking set of options. The result is often a DST that fits the clock but not the portfolio.
Using a Sponsor-Captive Advisor
Most DST providers only show you what they sponsor.
If their available inventory does not match your debt replacement requirements or equity structure, you either accept partial deferral or scramble elsewhere. Investors who focus only on gross sale value can be surprised by taxable boot or lower deployable equity than expected when the match is wrong.
The Documentary Stamp Tax Surprise
A closing cost that reduces deployable equity if not budgeted in advance.
Florida imposes a documentary stamp tax on any replacement property acquired during a 1031 exchange. It is not large, but it catches investors off guard when it is not budgeted in advance.
None of these failures are dramatic. They are quiet, avoidable, and expensive. Breakwater plans around all three before your property closes.
The Solution
What a Sponsor-Agnostic 1031 Advisor Actually Does for You
Breakwater is not a DST sponsor. We are a dedicated 1031 exchange advisory firm. We work exclusively for the investor, not the sponsor, and our only job is to get your exchange right, and get you into the right asset.
Here is what that looks like in practice:
Pre-Sale Exchange Strategy
Map your requirements before the 45-day clock starts.
Get your debt and equity requirements mapped to a qualifying replacement property before your 45-day clock starts, even if you are still two months from listing your relinquished property.
Sponsor-Agnostic Inventory Access
Access every major sector, not just one sponsor's availability.
Access institutional DSTs across every major sector nationwide, even if the only options you have seen so far came from a single Florida-based sponsor with one property type.
Full-Cycle Coordination
Every closing cost modeled in advance so nothing surprises you.
Have every closing cost including Florida's documentary stamp tax modeled in advance so nothing reduces your deployable equity at the table, even if your CPA has never flagged it before.
Get Your Exchange Right in Three Steps
Start Your Free Florida Exchange Analysis
Same-day inventory match based on your position.
Tell us where you are in your transaction. Sold, under contract, or still planning. We review your debt and equity position and match you to available inventory across every sector the same day.
We Build Your Replacement Shortlist
Pre-screened DSTs matched before your 45-day clock starts.
Before your 45-day clock starts, we identify pre-screened DSTs that match your exact deferral requirements, account for the documentary stamp tax on your replacement property, and coordinate with your CPA and QI so nothing reduces your deployable equity at closing.
Close With Everything Handled
Every step managed through the finish line.
From debt replacement verification to full closing documentation, we manage every step through the finish line. You close knowing your capital is in the right asset, not just any asset that fit the clock.
No obligation. No cost to review your situation.
What You Get Access To
Institutional-Grade Replacement Properties Matched to Your Exchange
Each offering includes full due diligence documentation, debt and equity specifications, and projected cash flow. Everything you need to make a confident identification before your clock expires.
Passco Riverside DST
Sponsor: Passco Companies, LLC
ERP 1031 Industrial Portfolio IV DST
Sponsor: Energy Related Properties (ERP)
Why Not Go Direct?
Advisory-Led vs. Direct-to-Sponsor: What You Are Actually Choosing Between
Inventory
Direct-to-Sponsor
Limited to what that sponsor sells.
Advisory-Led (Breakwater)
Full marketplace across all sectors.
Debt/Equity Matching
Direct-to-Sponsor
Your responsibility.
Advisory-Led (Breakwater)
Handled and verified before identification.
Deadline Management
Direct-to-Sponsor
Your responsibility.
Advisory-Led (Breakwater)
Fully coordinated 45/180-day tracking.
Closing Cost Planning
Direct-to-Sponsor
Your responsibility.
Advisory-Led (Breakwater)
Documentary stamp and all costs modeled in advance.
CPA/QI Coordination
Direct-to-Sponsor
Your responsibility.
Advisory-Led (Breakwater)
Included. We manage the relationships.
Sponsor Alignment
Direct-to-Sponsor
Works for the sponsor.
Advisory-Led (Breakwater)
Works for you.
Portfolio Fit
Direct-to-Sponsor
One-size-fits-all.
Advisory-Led (Breakwater)
Structured to your specific exchange requirements.
| Feature | Direct-to-Sponsor | Advisory-Led (Breakwater) |
|---|---|---|
| Inventory | Limited to what that sponsor sells. | Full marketplace across all sectors. |
| Debt/Equity Matching | Your responsibility. | Handled and verified before identification. |
| Deadline Management | Your responsibility. | Fully coordinated 45/180-day tracking. |
| Closing Cost Planning | Your responsibility. | Documentary stamp and all costs modeled in advance. |
| CPA/QI Coordination | Your responsibility. | Included. We manage the relationships. |
| Sponsor Alignment | Works for the sponsor. | Works for you. |
| Portfolio Fit | One-size-fits-all. | Structured to your specific exchange requirements. |
Going direct costs less upfront. Exchanging into the wrong asset in Florida's market can cost you years of compounding on misallocated capital.
The Rules
Before You Sell, Know These
A 1031 Exchange can protect six figures in federal tax liability. One procedural mistake eliminates that protection entirely.
Qualified Intermediary Required
You cannot receive or control the sale proceeds at any point. A QI must be engaged before your relinquished property closes. Do it after and your exchange is disqualified before it begins.
The 45-Day Identification Window
From the day of sale, you have exactly 45 calendar days to identify replacement properties in writing. The IRS offers no extensions and no exceptions, regardless of circumstance.
The 180-Day Closing Rule
Your replacement property must close within 180 days of your sale date. Miss this deadline and the full capital gain becomes taxable immediately.
Full Reinvestment for Full Deferral
To defer 100% of your capital gains, your replacement property must equal or exceed both the value and the debt of your relinquished property. Any shortfall becomes taxable boot. Partial deferral is allowed but must be planned for deliberately, not discovered at closing.
Investment Use Required
The replacement property must be held for investment or business use. Exchanging into a vacation home without following strict IRS safe harbor rental rules will disqualify your exchange. Florida's vacation rental market makes this a more common trap here than in most states.
The Documentary Stamp Tax
Florida imposes a documentary stamp tax on the replacement property at closing. It cannot be deferred through the exchange and must be budgeted as a separate closing cost. It will reduce your net deployable equity if not accounted for in advance.
Most Florida investors know rules 1 through 3. Rules 4 through 6 are where exchanges quietly fail, and where Breakwater planning pays for itself.
Credibility
16+ Years. $1.1B+ In Exchanges Guided. Zero Sponsor Allegiances.
Breakwater Capital is a dedicated 1031 exchange advisory firm. We bridge the gap between selling a Florida investment property and securing a tax-deferred legacy, for accredited investors who cannot afford to waste the state's greatest tax advantage on the wrong replacement asset.
Josh Chapin
President · 200+ Seminars on 1031 Exchanges
Josh has an extensive background in financial planning, specializing in unique investments and tax planning concepts. Since founding Breakwater Capital, he has developed deep expertise working with high-net-worth individuals and business owners — delivering thoughtful, personalized advice with a common-sense approach to complex strategies.
Series 7, Series 6, Series 63, Series 65, SIE, Life & Health
Supported by a Dedicated Exchange Team
Debbie Bannister
Certified Exchange Specialist · 18+ Years
Monique Wilson Kaiser
Senior Exchange Administrator · Since 1996
Naomi Booker-Abawag
Operations Manager
Taylor Pennington
Exchange Administrator · Since 2003
Experienced Advisory
Decades of collective experience in commercial real estate and tax-advantaged structures.
Customized Portfolios
We specialize in scaling exchanges, splitting one large sale into multiple DST assets across sectors and geographies to meet your exact deferral requirements.
Client-First Philosophy
We work for you, not the sponsor. Our recommendations are built around your exchange, not around what is easiest to move.
As Featured In
Featured Offering
MCG Arden NC Multifamily DST
Sponsor: Madison Capital Group
A Class A garden-style community in a high-growth North Carolina submarket, with strong employment fundamentals and favorable supply dynamics.
Every week you wait to build a replacement shortlist is a week your 45-day window narrows. Florida's market moves fast and quality DSTs with strong debt replacement characteristics are absorbed quickly. The investors who close into the best assets are not the ones who searched hardest in week six. They are the ones who started before they sold.
Two Ways to Get Started
Still planning your sale?
Request the Breakwater DST Overview. We will walk you through current inventory, show you how debt and equity matching works, and help you build a replacement shortlist before your property ever hits the market.
Already sold or closing soon?
Your 45-day clock may already be running. Call us directly and we will prioritize your file today.
Schedule a ConsultationNo obligation. No cost to review your exchange situation. If Breakwater is not the right fit for your transaction, we will tell you clearly and point you toward who is. Florida gives you the cleanest exchange environment in the country. The only thing standing between you and a well-executed exchange is starting the conversation.
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1031 Risk Disclosure:
There is no guarantee that any strategy will be successful or achieve investment objectives; Potential for property value loss – All real estate investments have the potential to lose value during the life of the investments; Change of tax status – The income stream and depreciation schedule for any investment property may affect the property owner's income bracket and/or tax status. An unfavorable tax ruling may cancel deferral of capital gains and result in immediate tax liabilities; Potential for foreclosure – All financed real estate investments have potential for foreclosure; Illiquidity – Because 1031 exchanges are commonly offered through private placement offerings and are illiquid securities. The secondary market for these investments is very limited, and early sale is not guaranteed. Reduction or Elimination of Monthly Cash Flow Distributions – Like any investment in real estate, if a property unexpectedly loses tenants or sustains substantial damage, there is potential for suspension of cash flow distributions; Impact of fees/expenses – Costs associated with the transaction may impact investors' returns and may outweigh the tax benefits.
Real Estate Risk Disclosure:
There is no guarantee that any strategy will be successful or achieve investment objectives. Potential for property value loss – All real estate investments have the potential to lose value during the life of the investments. Change of tax status – The income stream and depreciation schedule for any investment property may affect the property owner's income bracket and/or tax status. An unfavorable tax ruling may cancel deferral of capital gains and result in immediate tax liabilities. Potential for foreclosure – All financed real estate investments have potential for foreclosure. Illiquidity – These assets are commonly offered through private placement offerings and are illiquid securities. There is no secondary market for these investments. Reduction or Elimination of Monthly Cash Flow Distributions – Like any investment in real estate, if a property unexpectedly loses tenants or sustains substantial damage, there is potential for suspension of cash flow distributions. Impact of fees/expenses – Costs associated with the transaction may impact investor's returns and may outweigh the tax benefits. Stated tax benefits – Any stated tax benefits are not guaranteed and are subject to changes in the tax code. Speak to your tax professional prior to investing.
Opportunity Zone Disclosures:
Investing in opportunity zones is speculative. Opportunity zones are newly formed entities with no operating history. There is no assurance of investment return, property appreciation, or profits. The ability to resell the fund's underlying investment properties or businesses is not guaranteed. Investing in opportunity zone funds may involve a higher level of risk than investing in other established real estate offerings. Long-term investment. Opportunity zone funds have illiquid underlying investments that may not be easy to sell and the return of capital and realization of gains, if any, from an investment will generally occur only upon the partial or complete disposition or refinancing of such investments. Limited secondary market for redemption. Although secondary markets may provide a liquidity option in limited circumstances, the amount you will receive typically is discounted to current valuations. Difficult valuation assessment. The portfolio holdings in opportunity zone funds may be difficult to value because financial markets or exchanges do not usually quote or trade the holdings. As such, market prices for most of a fund's holdings will not be readily available. Capital call default consequences. Meeting capital calls to provide managers with the pledged capital is a contractual obligation of each investor. Failure to meet this requirement in a timely manner could elicit significant adverse consequences, including, without limitation, the forfeiture of your interest in the fund. Leverage. Opportunity zone funds may use leverage in connection with certain investments or participate in investments with highly leveraged capital structures. Leverage involves a high degree of financial risk and may increase the exposure of such investments to factors such as rising interest rates, downturns in the economy or deterioration in the condition of the assets underlying such investments. Unregistered investment. As with other unregistered investments, the regulatory protections of the Investment Company Act of 1940 are not available with unregistered securities. Regulation. It is possible, due to tax, regulatory, or investment decisions, that a fund, or its investors, are unable realize any tax benefits. You should evaluate the merits of the underlying investment and not solely invest in an opportunity zone fund for any potential tax advantage.