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3060 Pirates Retreat Ct, Kissimmee, FL 34747, 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
$36,393
$3,033/mo · at 67% occupancy & $198/night
-$14,727
-$1,227/mo after costs & mortgage
Cap rate
3%
Cash-on-cash
-9.8%
DSCR
0.51
Confidence
Your assumptions
Revenue
$36,393/yr
Market avg: $36,393/yr · 67% occ · $198 ADR
Financing
$29,939/yr
Operating costs
$21,181/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 50 properties
$117–$329
Median $198
30%–94%
Median 68%
$19.9K–$61.0K
Median $35.2K
196–365
Median 267
This property · $36.4K
Comparable properties (50)
Cash flow potential Low · Appreciation potential Medium
231 days available · 197 days booked ·
318 days available · 250 days booked ·
264 days available · 211 days booked ·
254 days available · 203 days booked ·
199 days available · 181 days booked ·
300 days available · 230 days booked ·
365 days available · 229 days booked ·
334 days available · 204 days booked ·
274 days available · 241 days booked ·
351 days available · 225 days booked ·
270 days available · 221 days booked ·
365 days available · 243 days booked ·
252 days available · 216 days booked ·
296 days available · 212 days booked ·
274 days available · 193 days booked ·
243 days available · 225 days booked ·
365 days available · 185 days booked ·
316 days available · 180 days booked ·
285 days available · 194 days booked ·
267 days available · 208 days booked ·
252 days available · 198 days booked ·
326 days available · 184 days booked ·
242 days available · 125 days booked ·
334 days available · 234 days booked ·
236 days available · 202 days booked ·
365 days available · 280 days booked ·
312 days available · 138 days booked ·
263 days available · 182 days booked ·
334 days available · 202 days booked ·
241 days available · 194 days booked ·
251 days available · 138 days booked ·
311 days available · 227 days booked ·
196 days available · 173 days booked ·
249 days available · 141 days booked ·
306 days available · 114 days booked ·
299 days available · 205 days booked ·
266 days available · 155 days booked ·
244 days available · 173 days booked ·
324 days available · 187 days booked ·
217 days available · 136 days booked ·
261 days available · 160 days booked ·
218 days available · 104 days booked ·
290 days available · 140 days booked ·
227 days available · 164 days booked ·
249 days available · 152 days booked ·
250 days available · 132 days booked ·
245 days available · 116 days booked ·
337 days available · 119 days booked ·
233 days available · 133 days booked ·
220 days available · 139 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
~$123.5K
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
$254.1K
Break-even purchase price
Break-even is ~49% below the Zestimate, a discount sellers in Kissimmee rarely accept. Treat the number as a walk-away line rather than an opening offer.
DSCR cash-flow buyer
0.51
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 Kissimmee submarket.
For a buyer who materially participates and qualifies for the STR tax treatment.
$123.5K
Estimated first-year deduction · range $102.5K–$140.8K
Why this matters here
At a marginal bracket, this deduction can be worth $37.9K–$52.1K 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 -9.8%, DSCR 0.51, cash flow -$14,727/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $375,000 | -6.2% | 0.68 | Below break-even |
| -22% | $390,000 | -6.7% | 0.65 | Below break-even |
| -15% | $425,000 | -7.8% | 0.60 | Below break-even |
| -8% | $460,000 | -8.8% | 0.55 | Below break-even |
| Asking | $500,000 | -9.8% | 0.51 | Below break-even |
| +8% | $540,000 | -10.7% | 0.47 | Below break-even |
| +15% | $575,000 | -11.3% | 0.44 | Below break-even |
Break-even price
$254,052
~49% under Zestimate. Where this property reaches 1.0 DSCR and neutral cash flow.
Discount needed
−$245,948
The gap between asking and the price a cash-flow buyer can underwrite.
If refi to 5.5% in 24 mo
+$4,388/yr
Illustrative cash-flow improvement at asking price if rates fall. Planning figure, not a forecast.
Annual avg $3,033 · peaks at $3,906 in Jan
Annual avg 67% · peaks at 76% in Feb
−$1,227/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$145,000
Return on cash:7.1%
DSCR below 1.0 — but you can still qualify
Your DSCR is 0.51 · 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
9.6%
over 5-yr hold, with tax shield
Equity multiple
1.5×
total proceeds vs. $145,000 invested
Projected value at exit
$638,141
year 5 · 5.0% annual appreciation
Tax shield contribution
+6.0 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $128,809 | $25,000 | $30,968 | $184,777 |
| Year 2 | $132,894 | $51,250 | $16,787 | $200,931 |
| Year 3 | $137,274 | $78,813 | $3,160 | $219,246 |
| Year 4 | $141,970 | $107,753 | -$9,905 | $239,819 |
| Year 5 | $147,007 | $138,141 | -$22,399 | $262,749 |
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 Kissimmee 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.