Westport

Westport is two things on the same ground, and the difference is the time of day. On a Tuesday evening the residential streets behind the commercial strip — Pennsylvania Avenue and the blocks around it — are quiet frame-and-brick houses with driveways that are really just two strips of concrete. On a Saturday at 12:40 a.m., Westport Road is a full entertainment district operating at capacity.

Both are permanent. You should see both before you buy here, and most people only see one.

The number that actually matters

Walk Score 93. The highest in Kansas City, in a city whose overall score is 35. It is not a marketing figure — a gastropub, small shops, a bookstore, a bar, and a bus stop are all inside a ten-minute walk. The fare-free streetcar stop opened at 39th and Main in October 2025, six blocks east, putting the Plaza, the art museums, Union Station and the Crossroads on a free train.

Three minutes from the Plaza. Eight from downtown. A typical home value around $276,000, up 2.5% on the year — meaningfully below the Plaza next door.

What you are buying

Old. 1880s–1920s frame and brick houses, four-squares, and apartment courts behind a 19th-century commercial main street. A house of that age has systems at or past the end of their design life, and the cost shows up in specific, inspectable places: the wiring, the panel, the sewer lateral, and the roof. Get a sewer scope, take the panel cover off, and put eyes on the roof and foundation before any contingency comes off. Those four items are where the closing-table surprises live here.

Off-street parking is scarce to nonexistent on many of these lots. You will street-park, and on a Friday night you will street-park badly.

Zillow counted 4 for-sale listings in Old Westport in May 2026. It is a small, tight, old market, and listings do not sit.

The parts nobody prints

Noise. Westport Road is a bar street. If you buy within two blocks of it, you are buying the sound of a bar street at 1:45 a.m. on Fridays, Saturdays, home-game nights, and St. Patrick's Day. That sound comes with the house and it is not going to change — the district has operated this way for generations. Go sit in a parked car on Pennsylvania Avenue at midnight on a Saturday and find out how it lands for you before you write, not after.

Taxes. The KCMO 1% earnings tax, because a Westport address is Kansas City, Missouri. And 83.882 mills against a 19% assessment ratio — roughly 1.594% of market value a year, in a county whose assessments are still in litigation.

Boundaries. What locals call "Westport," the data providers split into Old Westport and Plaza Westport. Every figure on this page is Old Westport. Check which one a listing is actually in.

Schools

Westport is served by Kansas City Public Schools (District 33). Note the general rule in this metro: school district boundaries do not follow city or neighborhood lines. Run the specific street address through the district's own boundary locator rather than trusting a neighborhood name.

A last note on the ground itself

Westport was platted in the 1850s, incorporated in 1857, and annexed by Kansas City in 1899. Kelly's Westport Inn has operated in the 1851 Ewing Brothers store — the oldest surviving building in Kansas City — since 1947. The street grid you would be buying into predates the city that surrounds it, which is also why it does not behave like a suburb: narrow lots, no setbacks to speak of, and a commercial main street running straight through the middle of it.