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REI Lense

Winchester, VA Short-Term Rental / Airbnb Analysis

Analyze rental property cap rates, cash-on-cash returns, and cashflow for short-term rental / airbnb investments in Winchester, VA. Based on 10+ datapoints.

Winchester, VA Short-Term Rental / Airbnb Investment Snapshot

Based on 10+ short-term rental / airbnb datapoints

Median Cap Rate

2.9%

Avg Cash on Cash

-14.4%

Median Cashflow

-$1,227/mo

Avg Rent Estimate

$2,575/mo

Avg Price

$463,733

Price Range

$296,100 - $598,895

Rent to Price

0.56%

low ratio

Positive Cashflow

0%

of analyzed properties

Recent real estate investor listings analysed as short-term rental / airbnb deals in Winchester, VA

Winchester, VA is a premium short-term rental market where property values drive long-term wealth. While cap rates are modest at 2.9%, the mid-to-upper tier property prices reflect strong underlying demand. STR investors here typically benefit from appreciation alongside rental income.

Across 10+ analyzed properties, Winchester, VA STR investments show a median monthly cashflow of -$1,227 with an average estimated nightly-rate-adjusted revenue of $2,575/month. These figures reflect real property data, not projections.

1960 Siler Rd, Winchester, VA 22603

Price

$491,600

Rent

$3,654

CachFlow

-$954

CoC

-9.44

Full Analysis

310 Goldenrod Rd, Winchester, VA 22602

Price

$430,000

Rent

$2,714

CachFlow

-$1,122

CoC

-12.43

Full Analysis

414 N Braddock St, Winchester, VA 22601

Price

$550,900

Rent

$2,042

CachFlow

-$2,310

CoC

-20.73

Full Analysis

2346 Welltown Rd, Winchester, VA 22603

Price

$296,100

Rent

$2,718

CachFlow

-$318

CoC

-4.76

Full Analysis

2122 Jones Rd, Winchester, VA 22602

Price

$762,100

Rent

$2,712

CachFlow

-$2,852

CoC

-19.22

Full Analysis
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Winchester, VA Airbnb Market Insights

  • Median cashflow is -$1,227/month — careful deal selection is essential here
  • 2.9% median cap rate is typical of appreciation-focused markets
  • At 0% positive cashflow rate, Winchester, VA requires selective property picks
  • Mid-to-upper tier market with properties from $296,100 to $598,895
  • Consider this market if your strategy favors equity growth with rental income covering holding costs

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