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335 Highland Ave, Winchester, MA 01890, 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
$62,866
$5,239/mo · at 40% occupancy & $361/night
-$176,496
-$14,708/mo after costs & mortgage
Cap rate
-1.1%
Cash-on-cash
-26.3%
DSCR
-0.18
Confidence
Your assumptions
Revenue
$62,866/yr
Market avg: $62,866/yr · 40% occ · $361 ADR
Financing
$149,723/yr
Operating costs
$89,639/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 5 properties
$318–$725
Median $361
18%–63%
Median 40%
$47.9K–$79.9K
Median $56.5K
244–365
Median 338
This property · $62.9K
Comparable properties (5)
Cash flow potential Low · Appreciation potential Medium
338 days available · 122 days booked ·
365 days available · 227 days booked ·
244 days available · 145 days booked ·
301 days available · 71 days booked ·
362 days available · 169 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
~$617.6K
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
—
Break-even purchase price
Even a deep discount doesn't get this deal to break even within a realistic range, so there's no price anchor to negotiate toward. A price-disciplined buyer should pass unless the revenue assumptions change.
DSCR cash-flow buyer
-0.18
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 Winchester submarket.
For a buyer who materially participates and qualifies for the STR tax treatment.
$617.6K
Estimated first-year deduction · range $512.6K–$704.1K
Why this matters here
At a marginal bracket, this deduction can be worth $189.7K–$260.5K 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 -26.3%, DSCR -0.18, cash flow -$176,496/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $1,875,375 | -27.4% | -0.24 | Below break-even |
| -22% | $1,950,390 | -27.2% | -0.23 | Below break-even |
| -15% | $2,125,425 | -26.9% | -0.21 | Below break-even |
| -8% | $2,300,460 | -26.6% | -0.19 | Below break-even |
| Asking | $2,500,500 | -26.3% | -0.18 | Below break-even |
| +8% | $2,700,540 | -26.1% | -0.17 | Below break-even |
| +15% | $2,875,575 | -25.9% | -0.16 | Below break-even |
Break-even price
Out of range
This deal does not reach break-even within ±25% of asking.
Discount needed
—
The gap between asking and the price a cash-flow buyer can underwrite.
If refi to 5.5% in 24 mo
+$21,945/yr
Illustrative cash-flow improvement at asking price if rates fall. Planning figure, not a forecast.
Annual avg $5,239 · peaks at $6,624 in Aug
Annual avg 46% · peaks at 73% in Aug
−$14,708/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$725,145
Return on cash:-7.1%
DSCR below 1.0 — but you can still qualify
Your DSCR is -0.18 · 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
-3.2%
over 5-yr hold, with tax shield
Equity multiple
0.8×
total proceeds vs. $725,145 invested
Projected value at exit
$3,191,342
year 5 · 5.0% annual appreciation
Tax shield contribution
+4.5 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $644,175 | $125,025 | $52,025 | $821,225 |
| Year 2 | $664,603 | $256,301 | -$123,528 | $797,376 |
| Year 3 | $686,507 | $394,141 | -$298,124 | $782,524 |
| Year 4 | $709,994 | $538,873 | -$471,749 | $777,119 |
| Year 5 | $735,180 | $690,842 | -$644,387 | $781,635 |
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 Winchester 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.
24 Brookside Avenue, Winchester, MA, USA
3 bed 2 bath 8 guests
Revenue
$67,025/yr
Daily Rate
$305
Occupancy
0.8%
60 Maynard St, Arlington, MA 02474, USA
2 bed 1 bath 6 guests
Revenue
$59,158/yr
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2 bed 2 bath 6 guests
Revenue
$55,762/yr
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3 bed 2 bath 8 guests
Revenue
$74,091/yr
285 Alewife Brook Parkway, West Somerville, MA, USA
2 bed 1 bath 6 guests
Revenue
$63,073/yr
33 Conwell Ave, Somerville, MA 02144, USA
3 bed 2 bath 8 guests
Revenue
$63,902/yr
Daily Rate
$286
Occupancy
0.9%
Daily Rate
$360
Occupancy
0.6%
Daily Rate
$321
Occupancy
0.7%
Daily Rate
$286
Occupancy
0.9%
Daily Rate
$437
Occupancy
0.7%