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4004 San Gallo Dr, Kissimmee, FL 34741, 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
$34,562
$2,880/mo · at 70% occupancy & $195/night
-$16,320
-$1,360/mo after costs & mortgage
Cap rate
2.7%
Cash-on-cash
-10.9%
DSCR
0.45
Confidence
Your assumptions
Revenue
$34,562/yr
Market avg: $34,562/yr · 70% occ · $195 ADR
Financing
$29,939/yr
Operating costs
$20,943/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 50 properties
$109–$322
Median $196
30%–89%
Median 71%
$20.7K–$56.7K
Median $32.9K
152–365
Median 278
This property · $34.6K
Comparable properties (50)
Cash flow potential Low · Appreciation potential Medium
335 days available · 241 days booked ·
322 days available · 211 days booked ·
305 days available · 250 days booked ·
258 days available · 212 days booked ·
361 days available · 154 days booked ·
279 days available · 233 days booked ·
326 days available · 174 days booked ·
365 days available · 207 days booked ·
365 days available · 234 days booked ·
344 days available · 236 days booked ·
297 days available · 218 days booked ·
267 days available · 162 days booked ·
214 days available · 166 days booked ·
347 days available · 293 days booked ·
308 days available · 238 days booked ·
233 days available · 187 days booked ·
365 days available · 175 days booked ·
265 days available · 192 days booked ·
192 days available · 154 days booked ·
251 days available · 191 days booked ·
185 days available · 145 days booked ·
323 days available · 205 days booked ·
268 days available · 222 days booked ·
276 days available · 168 days booked ·
365 days available · 261 days booked ·
236 days available · 141 days booked ·
257 days available · 136 days booked ·
327 days available · 251 days booked ·
291 days available · 254 days booked ·
254 days available · 154 days booked ·
365 days available · 178 days booked ·
255 days available · 170 days booked ·
342 days available · 174 days booked ·
263 days available · 161 days booked ·
159 days available · 137 days booked ·
301 days available · 189 days booked ·
286 days available · 171 days booked ·
250 days available · 187 days booked ·
322 days available · 136 days booked ·
285 days available · 174 days booked ·
273 days available · 190 days booked ·
190 days available · 142 days booked ·
262 days available · 122 days booked ·
271 days available · 134 days booked ·
258 days available · 141 days booked ·
217 days available · 163 days booked ·
152 days available · 119 days booked ·
238 days available · 154 days booked ·
318 days available · 120 days booked ·
323 days available · 99 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
$227.4K
Break-even purchase price
Break-even is ~55% 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
0.45
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 -10.9%, DSCR 0.45, cash flow -$16,320/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $375,000 | -7.5% | 0.61 | Below break-even |
| -22% | $390,000 | -8.0% | 0.58 | Below break-even |
| -15% | $425,000 | -9.1% | 0.54 | Below break-even |
| -8% | $460,000 | -10.0% | 0.49 | Below break-even |
| Asking | $500,000 | -10.9% | 0.45 | Below break-even |
| +8% | $540,000 | -11.7% | 0.42 | Below break-even |
| +15% | $575,000 | -12.3% | 0.40 | Below break-even |
Break-even price
$227,448
~55% under Zestimate. Where this property reaches 1.0 DSCR and neutral cash flow.
Discount needed
−$272,552
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 $2,880 · peaks at $3,744 in Jan
Annual avg 66% · peaks at 76% in Feb
−$1,360/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$145,000
Return on cash:6%
DSCR below 1.0 — but you can still qualify
Your DSCR is 0.45 · 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
8.6%
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
+5.9 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $128,809 | $25,000 | $29,375 | $183,184 |
| Year 2 | $132,894 | $51,250 | $13,573 | $197,717 |
| Year 3 | $137,274 | $78,813 | -$1,702 | $214,384 |
| Year 4 | $141,970 | $107,753 | -$16,443 | $233,280 |
| Year 5 | $147,007 | $138,141 | -$30,642 | $254,505 |
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.