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4633 Fairy Tale Cir, Kissimmee, FL 34746, 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
$45,356
$3,780/mo · at 68% occupancy & $246/night
-$6,929
-$577/mo after costs & mortgage
Cap rate
4.6%
Cash-on-cash
-4.6%
DSCR
0.77
Confidence
Your assumptions
Revenue
$45,356/yr
Market avg: $45,356/yr · 68% occ · $246 ADR
Financing
$29,939/yr
Operating costs
$22,346/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 50 properties
$138–$409
Median $246
38%–91%
Median 69%
$25.3K–$105.6K
Median $43.5K
176–365
Median 270
This property · $45.4K
Comparable properties (50)
Cash flow potential Low · Appreciation potential Medium
346 days available · 273 days booked ·
365 days available · 299 days booked ·
337 days available · 255 days booked ·
304 days available · 247 days booked ·
337 days available · 176 days booked ·
365 days available · 232 days booked ·
365 days available · 242 days booked ·
291 days available · 151 days booked ·
365 days available · 255 days booked ·
270 days available · 187 days booked ·
365 days available · 230 days booked ·
305 days available · 250 days booked ·
258 days available · 185 days booked ·
263 days available · 212 days booked ·
280 days available · 215 days booked ·
264 days available · 209 days booked ·
320 days available · 167 days booked ·
227 days available · 173 days booked ·
365 days available · 226 days booked ·
212 days available · 177 days booked ·
257 days available · 173 days booked ·
294 days available · 172 days booked ·
259 days available · 191 days booked ·
298 days available · 189 days booked ·
314 days available · 259 days booked ·
215 days available · 163 days booked ·
271 days available · 159 days booked ·
237 days available · 215 days booked ·
295 days available · 249 days booked ·
268 days available · 190 days booked ·
365 days available · 234 days booked ·
308 days available · 238 days booked ·
316 days available · 152 days booked ·
267 days available · 197 days booked ·
261 days available · 165 days booked ·
176 days available · 153 days booked ·
262 days available · 155 days booked ·
251 days available · 191 days booked ·
265 days available · 151 days booked ·
256 days available · 127 days booked ·
243 days available · 150 days booked ·
256 days available · 136 days booked ·
270 days available · 166 days booked ·
283 days available · 162 days booked ·
256 days available · 117 days booked ·
255 days available · 170 days booked ·
243 days available · 108 days booked ·
190 days available · 142 days booked ·
222 days available · 127 days booked ·
286 days available · 111 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
$384.3K
Break-even purchase price
Break-even is ~23% 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
0.77
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 -4.6%, DSCR 0.77, cash flow -$6,929/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $375,000 | 0.5% | 1.02 | Positive |
| -22% | $390,000 | -0.3% | 0.99 | At break-even |
| -15% | $425,000 | -1.9% | 0.90 | Below break-even |
| -8% | $460,000 | -3.2% | 0.84 | Below break-even |
| Asking | $500,000 | -4.6% | 0.77 | Below break-even |
| +8% | $540,000 | -5.8% | 0.71 | Below break-even |
| +15% | $575,000 | -6.7% | 0.67 | Below break-even |
Break-even price
$384,282
~23% under Zestimate. Where this property reaches 1.0 DSCR and neutral cash flow.
Discount needed
−$115,718
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 $3,780 · peaks at $4,507 in Dec
Annual avg 67% · peaks at 78% in Feb
−$577/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$145,000
Return on cash:12.5%
DSCR below 1.0 — but you can still qualify
Your DSCR is 0.77 · 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
14.7%
over 5-yr hold, with tax shield
Equity multiple
1.8×
total proceeds vs. $145,000 invested
Projected value at exit
$638,141
year 5 · 5.0% annual appreciation
Tax shield contribution
+6.6 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $128,809 | $25,000 | $38,766 | $192,575 |
| Year 2 | $132,894 | $51,250 | $32,517 | $216,661 |
| Year 3 | $137,274 | $78,813 | $26,959 | $243,046 |
| Year 4 | $141,970 | $107,753 | $22,102 | $271,826 |
| Year 5 | $147,007 | $138,141 | $17,956 | $303,104 |
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.