Winchester, VA-WV Investor Insights

Real estate investment activity and market trends across 3 counties in the Winchester, VA-WV metro area

3,342 active investors · 2,228 acquisitions (last 12 mo)

Data as of May 2026 · Updated monthly

Active Investors3,342ilast 12 mo
Avg Acquisition$968Kilast 12 mo
Rental Yield6.9%ifrom geo_stats
Acquisitions2,228ilast 12 mo
Value-Add-54%ipurchase vs value

Recently Active Investors in Winchester, VA-WV

Investors with purchases in the last 6 months

#iInvestoriPortfolioiPortfolio ValueiLast PurchaseiLast Addressi
1DSP RB WEST WIND LLCiLong termi89i$2158.3Mi2024-02-15i142 Lewisham Dr, Stephens Cityi
2W W P INVESTMENTS LLCiLong termi64i$1.9Mi2025-10-03i315 Brill Rd, Star Tanneryi
3MILLWOOD GATEWAY LLCiLong termi48i$2.4Mi2022-04-15i392 Millwood Ave, Winchesteri
4SUNNY MEHTA LLCiLong termi39i$4.3Mi2025-07-22i142 Underwood Ln, Winchesteri
5JENNINGS INVESTMENTS LLCiLong termi34i$3.4Mi2025-12-19i123 Early Dr, Winchesteri

Investor Value Add

✓ Live Data

Avg Purchase

$968K

i

Avg Value

$444K

i
-54%ivalue appreciation

in Winchester, VA-WV Metro

Average Rents

✓ Live Data
1 Bedroom$1,622i
2 Bedroom$1,982i
3 Bedroom$2,457i

in Winchester, VA-WV Metro

Top Recent Sales in Winchester, VA-WV

Transactions by active real estate investors

20 E Hart St, Winchester

i

$279K

i
KEE PROPERTIES LLCiBlendedi· 2026-03-31i

111 Meadowview Ct, Winchester

i

$345K

i
BOCA LLCiLong termi· 2026-03-30i

127 Shirley St, Winchester

i

$340K

i
B & N PROPERTIES LLCiLong termi· 2026-03-27i

129 Indiana Trl, Winchester

i

$385K

i
WESTVIEW CUSTOM HOMES LLCiLong termi· 2026-03-27i

2445 Bear Wallow Hollow Rd, Augusta

i

$455K

i
DOUBLE S RANCH TRUSTiLong termi· 2026-03-24i

Investing in Winchester, VA-WV?

Close your next deal with a LendingOne DSCR or bridge loan.

Get a DSCR Loan

Free Market Report: Winchester, VA-WV Metro

Get rental comps, investor activity, and DSCR data for your target zip codes.

No spam. A loan advisor may reach out with relevant opportunities.