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6 Lisbon St, St. Augustine, FL 32080, USA
Priced too high to cash-flow with a loan — an equity or tax play, not income.
Investment potential
Your scenario · adjust the levers below or open advanced settings to see how returns change
$55,646
$4,637/mo · at 62% occupancy & $273/night
-$17,357
-$1,446/mo after costs & mortgage
Cap rate
3.5%
Cash-on-cash
-8.5%
DSCR
0.59
Confidence
Your assumptions
Revenue
$55,646/yr
Market avg: $55,646/yr · 62% occ · $273 ADR
Financing
$42,501/yr
Operating costs
$30,502/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 50 properties
$162–$442
Median $273
40%–93%
Median 62%
$28.4K–$83.1K
Median $54.2K
178–365
Median 327
This property · $55.6K
Comparable properties (50)
Cash flow potential Low · Appreciation potential Medium
365 days available · 213 days booked ·
365 days available · 286 days booked ·
365 days available · 230 days booked ·
365 days available · 254 days booked ·
356 days available · 262 days booked ·
365 days available · 220 days booked ·
365 days available · 234 days booked ·
347 days available · 202 days booked ·
365 days available · 227 days booked ·
365 days available · 240 days booked ·
365 days available · 190 days booked ·
365 days available · 255 days booked ·
253 days available · 157 days booked ·
312 days available · 212 days booked ·
365 days available · 265 days booked ·
236 days available · 195 days booked ·
365 days available · 225 days booked ·
303 days available · 166 days booked ·
365 days available · 239 days booked ·
328 days available · 212 days booked ·
365 days available · 228 days booked ·
365 days available · 232 days booked ·
365 days available · 246 days booked ·
365 days available · 222 days booked ·
277 days available · 164 days booked ·
224 days available · 190 days booked ·
268 days available · 149 days booked ·
280 days available · 203 days booked ·
330 days available · 171 days booked ·
365 days available · 217 days booked ·
258 days available · 162 days booked ·
248 days available · 125 days booked ·
318 days available · 156 days booked ·
253 days available · 120 days booked ·
258 days available · 137 days booked ·
365 days available · 201 days booked ·
320 days available · 151 days booked ·
325 days available · 175 days booked ·
268 days available · 133 days booked ·
225 days available · 144 days booked ·
268 days available · 161 days booked ·
358 days available · 164 days booked ·
365 days available · 211 days booked ·
286 days available · 189 days booked ·
233 days available · 143 days booked ·
178 days available · 138 days booked ·
296 days available · 134 days booked ·
200 days available · 135 days booked ·
215 days available · 135 days booked ·
291 days available · 140 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
~$175.3K
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.
Price-disciplined buyer
$419.9K
Break-even purchase price
Break-even is ~41% below the Zestimate, a discount sellers in St. Augustine rarely accept. Treat the number as a walk-away line rather than an opening offer.
DSCR cash-flow buyer
0.59
DSCR at asking
At asking price the property doesn't cover its own debt service, so it won't qualify for DSCR financing as modeled. If you need cash flow from day one, look at a mid-term-rental fallback or a different St. Augustine submarket.
For a buyer who materially participates and qualifies for the STR tax treatment.
$175.3K
Estimated first-year deduction · range $145.5K–$199.9K
Why this matters here
At a marginal bracket, this deduction can be worth $53.8K–$74.0K 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 -8.5%, DSCR 0.59, cash flow -$17,357/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $532,350 | -4.2% | 0.79 | Below break-even |
| -22% | $553,644 | -4.9% | 0.76 | Below break-even |
| -15% | $603,330 | -6.2% | 0.70 | Below break-even |
| -8% | $653,016 | -7.4% | 0.64 | Below break-even |
| Asking | $709,800 | -8.5% | 0.59 | Below break-even |
| +8% | $766,584 | -9.5% | 0.55 | Below break-even |
| +15% | $816,270 | -10.2% | 0.51 | Below break-even |
Break-even price
$419,918
~41% under Zestimate. Where this property reaches 1.0 DSCR and neutral cash flow.
Discount needed
−$289,882
The gap between asking and the price a cash-flow buyer can underwrite.
If refi to 5.5% in 24 mo
+$6,229/yr
Illustrative cash-flow improvement at asking price if rates fall. Planning figure, not a forecast.
Annual avg $4,637 · peaks at $5,193 in Jun
Annual avg 62% · peaks at 77% in Mar
−$1,446/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$205,842
Return on cash:8.8%
DSCR below 1.0 — but you can still qualify
Your DSCR is 0.59 · 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
11.2%
over 5-yr hold, with tax shield
Equity multiple
1.6×
total proceeds vs. $205,842 invested
Projected value at exit
$905,905
year 5 · 5.0% annual appreciation
Tax shield contribution
+6.2 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $182,858 | $35,490 | $47,512 | $265,859 |
| Year 2 | $188,656 | $72,755 | $30,989 | $292,400 |
| Year 3 | $194,874 | $111,882 | $15,314 | $322,070 |
| Year 4 | $201,541 | $152,966 | $499 | $355,007 |
| Year 5 | $208,690 | $196,105 | -$13,443 | $391,352 |
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 St. Augustine agent who knows which properties actually cash flow — and which to avoid.
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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.
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