Sign up for our newsletter
Monthly insights, tips, and exclusive offers for STR investors.
All Real Estate Services are offered through Chalet Realty (DBA of Mahalla Realty LLC).
Texas Real Estate Commission Consumer Protection NoticeTexas Real Estate Commission Information About Brokerage ServicesTREC DisclaimerChalet (“GetChalet Inc.”) provides general educational content and tools for real-estate investors. Chalet is not a law firm, CPA firm, or investment adviser, and does not provide tax, legal, or accounting advice. Nothing on this site creates a CPA-client, attorney-client, or fiduciary relationship. Tax laws change, and state rules may differ from federal rules (e.g., California decouples from federal bonus depreciation). Always consult your own qualified tax and legal professionals about your specific situation.
The term 'Airbnb' is used on our site in a colloquial sense, akin to saying 'I am going to Airbnb it.' This usage is intended to refer broadly to the concept of short-term rentals and not specifically to the Airbnb platform or services. Airbnb, Inc. is not affiliated with Chalet, nor does it endorse or sponsor our services. We use the term in this generalized manner to easily convey the idea of participating in short-term rental activities, recognizing 'Airbnb' as a term familiar to many in this context.
Affiliate & Referral Disclosure. Chalet may receive referral fees or other consideration when you engage with featured agents, lenders, cost-seg providers, or other partners referenced on this site. These relationships may influence which partners we present. We follow the FTC Endorsement Guides and aim to disclose material connections clearly and conspicuously.
Chalet (DBA of GetChalet Inc.) is not affiliated, associated, authorized, endorsed by, or in any way officially connected with Airbnb, Airbnb.com, or any of its subsidiaries or its affiliates. The official Airbnb website can be found at http://www.airbnb.com. The name "Airbnb" as well as related names, marks, emblems and images are registered trademarks of Airbnb, Inc.
66 Julia St, Saint Augustine, FL 32084
Covers its debt with margin to spare at the current price.
Investment potential
Your scenario · adjust the levers below or open advanced settings to see how returns change
$54,322
$4,527/mo · at 53% occupancy & $396/night
$13,777
$1,148/mo after costs & mortgage
Cap rate
9.8%
Cash-on-cash
12.1%
DSCR
1.64
Confidence
Your assumptions
Revenue
$54,322/yr
Market avg: $54,322/yr · 53% occ · $396 ADR
Financing
$21,574/yr
Operating costs
$18,972/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 50 properties
$226–$579
Median $399
23%–92%
Median 54%
$29.7K–$118.2K
Median $55.1K
212–365
Median 278
This property · $54.3K
Comparable properties (50)
Cash flow potential Medium · Appreciation potential Medium
293 days available · 226 days booked ·
266 days available · 206 days booked ·
253 days available · 191 days booked ·
365 days available · 256 days booked ·
336 days available · 146 days booked ·
239 days available · 170 days booked ·
282 days available · 152 days booked ·
298 days available · 182 days booked ·
293 days available · 188 days booked ·
365 days available · 272 days booked ·
281 days available · 152 days booked ·
293 days available · 242 days booked ·
265 days available · 136 days booked ·
261 days available · 155 days booked ·
251 days available · 189 days booked ·
274 days available · 202 days booked ·
284 days available · 113 days booked ·
273 days available · 149 days booked ·
264 days available · 133 days booked ·
257 days available · 170 days booked ·
212 days available · 137 days booked ·
216 days available · 141 days booked ·
291 days available · 213 days booked ·
260 days available · 143 days booked ·
296 days available · 117 days booked ·
259 days available · 125 days booked ·
316 days available · 171 days booked ·
234 days available · 154 days booked ·
319 days available · 118 days booked ·
257 days available · 124 days booked ·
286 days available · 147 days booked ·
321 days available · 109 days booked ·
278 days available · 91 days booked ·
239 days available · 177 days booked ·
241 days available · 163 days booked ·
268 days available · 132 days booked ·
249 days available · 148 days booked ·
288 days available · 122 days booked ·
302 days available · 94 days booked ·
302 days available · 138 days booked ·
329 days available · 92 days booked ·
277 days available · 124 days booked ·
226 days available · 150 days booked ·
232 days available · 99 days booked ·
286 days available · 111 days booked ·
364 days available · 110 days booked ·
326 days available · 89 days booked ·
359 days available · 127 days booked ·
264 days available · 97 days booked ·
268 days available · 120 days booked ·
Revenue and occupancy reflect Chalet's modeled estimates from observed booking activity for comparable active listings. Individual results vary with management, seasonality, and pricing.
Who this property is for
The same property is a great buy for one investor and a trap for another. Here's the honest read.
1031 / high-equity buyer
~$89.0K
Year-1 tax shield
Buying with cash or low leverage removes the debt-coverage problem entirely, so the thesis rests on appreciation plus a large first-year write-off. At roughly 25% of purchase price, the shield is substantial enough to carry the deal on its own.
DSCR cash-flow buyer
1.64
DSCR at asking
At asking price the property clears the 1.20 DSCR most lenders require, so it should qualify for DSCR financing and cover its own debt service from day one. This is the buyer this deal is built for.
Price-disciplined buyer
—
Break-even purchase price
Even a deep discount doesn't get this deal to break even within a realistic range, so there's no price anchor to negotiate toward. A price-disciplined buyer should pass unless the revenue assumptions change.
For a buyer who materially participates and qualifies for the STR tax treatment.
$89.0K
Estimated first-year deduction · range $73.9K–$101.5K
Why this matters here
At a marginal bracket, this deduction can be worth $27.3K–$37.5K in estimated federal tax saved.
This only applies if you meet the IRS material-participation tests for short-term rentals and are not using a full-service property manager.
Estimate, subject to CPA review. Cost-segregation percentages shown here are illustrative and depend on an actual study of the property.
Some states do not conform to federal bonus depreciation, so your state may not allow the same first-year treatment shown above.
Chalet can introduce a cost-segregation partner — this is not tax, legal, or financial advice.
How cash-on-cash return moves with purchase price. The marked line is break-even (1.0 DSCR).
At this price: cash-on-cash +12.1%, DSCR 1.64, cash flow $13,777/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $270,225 | 21.2% | 2.18 | Positive |
| -22% | $281,034 | 19.9% | 2.10 | Positive |
| -15% | $306,255 | 17.1% | 1.93 | Positive |
| -8% | $331,476 | 14.6% | 1.78 | Positive |
| Asking | $360,300 | 12.1% | 1.64 | Positive |
| +8% | $389,124 | 9.9% | 1.52 | Positive |
| +15% | $414,345 | 8.3% | 1.42 | Positive |
Break-even price
Out of range
This deal does not reach break-even within ±25% of asking.
Discount needed
—
The gap between asking and the price a cash-flow buyer can underwrite.
If refi to 5.5% in 24 mo
+$3,162/yr
Illustrative cash-flow improvement at asking price if rates fall. Planning figure, not a forecast.
Annual avg $4,527 · peaks at $5,727 in Jan
Annual avg 54% · peaks at 69% in Mar
$1,148/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$104,487
Return on cash:30.4%
You qualify for STR financing
Your DSCR is 1.64 · lenders typically require 1.0+.
Get matched with 2–3 vetted STR lenders, free.
What the deal returns over the hold — including the tax shield, which is the whole point for an appreciation buyer.
Levered IRR
32.0%
over 5-yr hold, with tax shield
Equity multiple
2.8×
total proceeds vs. $104,487 invested
Projected value at exit
$459,844
year 5 · 5.0% annual appreciation
Tax shield contribution
+8.7 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $92,820 | $18,015 | $46,705 | $157,540 |
| Year 2 | $95,763 | $36,931 | $61,297 | $193,991 |
| Year 3 | $98,920 | $56,792 | $76,716 | $232,427 |
| Year 4 | $102,304 | $77,647 | $92,974 | $272,925 |
| Year 5 | $105,933 | $99,544 | $110,084 | $315,561 |
Projection, not a promise.
Assumes 5.0% annual appreciation, 1.5% rent growth (operating costs held flat), and that the property qualifies for short-term-rental tax treatment. The year-1 depreciation shield depends on a real cost-segregation study and your tax situation — consult a CPA.
Appreciation is the dominant driver of this return. When cash flow is negative, the deal depends on the property gaining value — it is not paying for itself from income.
Appreciation, rent growth, and financing rates are editable under Edit financials.
STR deals turn on local rules and demand that a generalist agent misses. Chalet matches you with a vetted Saint Augustine agent who knows which properties actually cash flow — and which to avoid.
© 2026 Chalet. All rights reserved.
This analysis is generated by Chalet's Airbnb Calculator
Visit getchalet.com for more tools
Real Estate Investment Analysis & Market Insights
Disclaimer
This page and the data presented are for informational purposes only. The information provided should not be construed as financial, legal, or investment advice. Market conditions can change rapidly, and past performance does not guarantee future results. Always consult with qualified professionals before making investment decisions.
16 Ewing St a, St. Augustine, FL 32084, USA
3 bed 2 bath 8 guests
Revenue
$35,767/yr
Daily Rate
$350
Occupancy
0.5%
69 Josiah St, St. Augustine, FL 32084, USA
3 bed 2 bath 8 guests
Revenue
$45,430/yr
430 Francis St, St. Augustine, FL 32084, USA
3 bed 2 bath 8 guests
Revenue
$34,521/yr
2 Clark Street, St. Augustine, FL, USA
3 bed 2 bath 8 guests
Revenue
$50,411/yr
18 Clark St, St. Augustine, FL 32084, USA
3 bed 3 bath 8 guests
Revenue
$61,528/yr
234 RAVENSWOOD Drive, Saint Augustine, FL 32084
2 bed 2 bath 6 guests
Revenue
$36,218/yr
Daily Rate
$345
Occupancy
0.5%
Daily Rate
$275
Occupancy
0.4%
Daily Rate
$346
Occupancy
0.6%
Daily Rate
$421
Occupancy
0.6%
Daily Rate
$320
Occupancy
0.6%