Performance indicators for the Winchester short-term rental market based on reliable data.
Listings
Reliable / Active
Cap Rate
Middle-Earners Gross Yield
Revenue
Middle-Earners Revenue
Occupancy
Middle-Earners Occupancy
Home Value
Median Home Sale Price
Top Earners
Top-Earners Revenue
The highest-performing listings in Winchester.
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Challenging to Investors
Winchester permits STRs citywide, but imposes a 45‑day annual cap in many districts and requires primary residence in several zones (LR, MR, HR, HR‑1, B‑2, RO‑1), while B‑1/RB‑1 are limited to 5 sleeping rooms and often need a CUP. Operators must obtain a zoning use permit, a business license, comply with annual inspections, safety standards, noise/parking rules, and maintain an annual ledger—significantly increasing compliance risk for investors.
Local STR Agent
STR specialist · Winchester, VA
Winchester is the northwesternmost independent city in the Commonwealth of Virginia, United States. It is the county seat of Frederick County, although the two are separate jurisdictions. As of the 2020 census, the city's population was 28,120. It is the principal city of the Winchester metropolitan area extending into West Virginia, which is a part of the Washington–Baltimore combined statistical area. Winchester is home to Shenandoah University and the Museum of the Shenandoah Valley.