Is Winchester City, VA good for real estate investing?

Winchester City has an investment score of 59/100, rated as "Hold". The county ranks #402 nationally among 1000 counties analyzed.

What is the rent-to-price ratio in Winchester City?

The rent-to-price ratio in Winchester City is 5.42% annually, which ranks in the 36th percentile nationally. Higher ratios indicate better cash flow potential.

What is the median home price in Winchester City?

The median home price in Winchester City is $363,487. This ranks #819 in affordability among all US counties.

Can you cash flow on rental properties in Winchester City?

Based on median values with 20% down at current rates, a typical rental in Winchester City would generate negative cash flow of $838/month. Individual property performance varies based on purchase price, rent, and operating expenses.

Winchester City

VirginiaPopulation: 28,103

/100

Hold

#402 of 1,000 counties

#63 in Virginia (133 counties)

Analysis by RentalCalcs ResearchIndependent data + algorithm-driven scoring

Updated July 28, 2026Sources: Zillow ZHVI, Zillow ZORI, US Census ACS, Tax Foundation

Market Snapshot

$363,487

Median Home Price

59% above national median

$1,642/mo

Median Rent

13% above national median

5.42%

Rent-to-Price Ratio

Top 64% nationally

-$838

Est. Monthly Cash Flow

With 20% down at 6.9% rate

Scenario comparison

Same $1,642/mo rent assumption, 20% down, 6.85% rate. What changes is the acquisition price.

Scenario	Purchase price	Monthly cash flow	Cap rate	Cash-on-cash
75% of median value-add or distressed	$272,615	-$362/mo	4.7%	-6.9%
Median typical MLS deal	$363,487	-$838/mo	3.5%	-12.0%
125% of median newer / premium	$454,359	-$1,315/mo	2.8%	-15.1%

Price History

Median Home Price

Median Rent

Historical data from Zillow ZHVI/ZORI

Quick Investment Calculator

Down Payment20%

5%50%100%

Purchase

Purchase Price$363,487

Down Payment (20%)$72,697

Loan Amount$290,790

Interest Rate6.85%

Monthly Cash Flow

Gross Rent+$1,642

Monthly P&I-$1,905

Est. Expenses (35%)-$575

Net Cash Flow-$838/mo

3.5%

Cap Rate (all cash)

-12.0%

Cash-on-Cash Return

5.42%

Rent-to-Price Ratio

Negative leverage: At 6.85% rates, borrowing costs exceed the 3.5% cap rate. All-cash buyers may see better returns.

* Based on county median values. 35% expenses include taxes, insurance, maintenance, vacancy, and property management. Actual results vary by property.

Run Full Analysis Try House Hack Strategy

Score Breakdown

Overall Investment Score

59/100

Cash Flow(30%)

51/100

Based on 5.42% rent-to-price ratio. Higher ratios indicate stronger cash flow potential.

Appreciation(25%)

82/100

Based on 3.6% YoY price growth. Moderate growth (3-8%) scores highest.

Stability(25%)

50/100

Population data not available.

Affordability(20%)

52/100

Based on price relative to estimated local incomes.

Scores are calculated using real Zillow home value and rent data, Census population data, and economic indicators. The weighted average produces the overall investment score. Markets with missing rent data use estimated values based on regional averages.

Investment Outlook

Strengths

+Complete rent data available

Challenges

-Below-average rent-to-price ratio (5.42%)
-Negative cash flow at typical financing (-$838/mo)
-Negative leverage (cap rate 3.5% < mortgage rate 6.9%)

Economic Indicators

Population

28,103

Median Income

—

Data pending

Unemployment Rate

—

Data pending

Price-to-Income

—

Data pending

Who this market fits

Best for

+All-cash buyers: removing debt service flips the cap rate to actual yield

Skip if

−You need positive cash flow on day one at typical leverage
−You can't tolerate negative leverage (cap rate below mortgage rate today)

Compare to Nearby Counties

County					Verdict
Lynchburg CityVA	60	$239,431	$1,282	6.43%	Buy	View
CurrentWinchester CityVA	59	$363,487	$1,642	5.42%	Hold
Portsmouth CityVA	59	$255,109	$1,581	7.44%	Hold	View
FrederickVA	59	$419,936	$2,103	6.01%	Hold	View
NelsonVA	58	$348,365	Est. pending	—	Hold	View
Hopewell CityVA	58	$210,055	$1,137	6.49%	Hold	View

The Bottom Line

HoldWinchester City is a neutral market. Consider house hacking or targeting below-market deals.

Winchester City in Virginia scores 59/100, ranking #402 of 1,000 US counties (top 51%). At 20% down and current rates, a median-priced rental loses about $838/month; the 5.42% gross rent-to-price ratio doesn't survive debt service. The thesis here is appreciation, value-add, house hacking, or all-cash.

Monthly Cash Flow

$-838/mo

Cap Rate

3.5%

Cash-on-Cash

-12.0%