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4849 WINTON Circle, Saint Augustine, FL 32086
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
$59,862
$4,989/mo · at 61% occupancy & $367/night
$5,691
$474/mo after costs & mortgage
Cap rate
7.1%
Cash-on-cash
3.8%
DSCR
1.19
Confidence
Your assumptions
Revenue
$59,862/yr
Market avg: $59,862/yr · 61% occ · $367 ADR
Financing
$29,939/yr
Operating costs
$24,232/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 42 properties
$161–$758
Median $367
21%–78%
Median 61%
$31.7K–$144.7K
Median $58.1K
193–365
Median 275
This property · $59.9K
Comparable properties (42)
Cash flow potential Medium · Appreciation potential Medium
322 days available · 198 days booked ·
273 days available · 173 days booked ·
263 days available · 190 days booked ·
296 days available · 157 days booked ·
307 days available · 136 days booked ·
291 days available · 195 days booked ·
270 days available · 158 days booked ·
284 days available · 138 days booked ·
365 days available · 242 days booked ·
243 days available · 146 days booked ·
338 days available · 253 days booked ·
259 days available · 168 days booked ·
301 days available · 171 days booked ·
277 days available · 195 days booked ·
244 days available · 158 days booked ·
245 days available · 99 days booked ·
255 days available · 192 days booked ·
350 days available · 205 days booked ·
268 days available · 121 days booked ·
270 days available · 185 days booked ·
316 days available · 132 days booked ·
310 days available · 189 days booked ·
327 days available · 232 days booked ·
248 days available · 163 days booked ·
365 days available · 282 days booked ·
243 days available · 168 days booked ·
312 days available · 150 days booked ·
344 days available · 159 days booked ·
272 days available · 110 days booked ·
297 days available · 174 days booked ·
201 days available · 122 days booked ·
236 days available · 110 days booked ·
302 days available · 181 days booked ·
239 days available · 124 days booked ·
237 days available · 158 days booked ·
193 days available · 133 days booked ·
201 days available · 144 days booked ·
286 days available · 131 days booked ·
279 days available · 100 days booked ·
257 days available · 124 days booked ·
322 days available · 84 days booked ·
232 days available · 88 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
$595.0K
Break-even purchase price
The deal already breaks even at or above the Zestimate, so you don't need a discount to make the math work. Buy at asking and the numbers still hold — rare enough in Saint Augustine to be worth moving on.
DSCR cash-flow buyer
1.19
DSCR at asking
The property covers its debt service at asking but sits below the 1.20 most lenders want to see, so expect a larger down payment or a rate buy-down to get it financed. There's no margin for a soft season.
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 +3.8%, DSCR 1.19, cash flow $5,691/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $375,000 | 11.2% | 1.59 | Positive |
| -22% | $390,000 | 10.1% | 1.53 | Positive |
| -15% | $425,000 | 7.8% | 1.40 | Positive |
| -8% | $460,000 | 5.8% | 1.29 | Positive |
| Asking | $500,000 | 3.8% | 1.19 | Positive |
| +8% | $540,000 | 2.1% | 1.10 | Positive |
| +15% | $575,000 | 0.7% | 1.03 | Positive |
Break-even price
$595,050
~-19% under Zestimate. Where this property reaches 1.0 DSCR and neutral cash flow.
Discount needed
−$95,050
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 $4,989 · peaks at $6,343 in Feb
Annual avg 59% · peaks at 78% in Mar
$474/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$145,000
Return on cash:21.2%
You qualify for STR financing
Your DSCR is 1.19 · 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
23.0%
over 5-yr hold, with tax shield
Equity multiple
2.3×
total proceeds vs. $145,000 invested
Projected value at exit
$638,141
year 5 · 5.0% annual appreciation
Tax shield contribution
+7.6 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $128,809 | $25,000 | $51,386 | $205,195 |
| Year 2 | $132,894 | $51,250 | $57,975 | $242,119 |
| Year 3 | $137,274 | $78,813 | $65,475 | $281,562 |
| Year 4 | $141,970 | $107,753 | $73,901 | $323,624 |
| Year 5 | $147,007 | $138,141 | $83,265 | $368,412 |
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.
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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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