Is Winston Square safe?
San Antonio, Texas · safety score updated nightly
Be careful — go in daylight and stay on the busier streets.
VibeLoco rates Winston Square as “Caution”.
What makes up this score?Recent news
Gogo's take on Winston Square
“Go with care. Winston Square is a modest, working-class residential neighborhood on San Antonio's inner Westside that is generally peaceful during daylight hours. Visitors should remain aware of their surroundings after dark and avoid leaving valuables visible in parked vehicles due to elevated property crime in the broader area.”
About the area
Winston Square is an established, predominantly residential neighborhood located southwest of downtown San Antonio, bordered by major corridors like Castroville Road and Highway 90. The community is characterized by modest mid-century bungalows, local family-run eateries, and close proximity to Port San Antonio. It is primarily a residential area with limited standard tourist infrastructure.
- Residential
- Working-Class
- Car-Dependent
- Authentic Dining
Walking and biking in Winston Square
Walk score: 42/100 · Bike score: 41/100
Dedicated bike infrastructure is minimal on neighborhood streets, though cyclists can connect to the Westside Creeks trail network a short ride to the east.
Reasons to go, and reasons to think twice
Pros
- Convenient highway access to downtown San Antonio and major employment centers like Port San Antonio
- Tight-knit, multi-generational community atmosphere on interior residential blocks
- Authentic and affordable neighborhood dining options along surrounding commercial corridors
Cons
- Above-average property crime and vehicle burglary rates relative to Bexar County suburban benchmarks
- Elevated poverty rate and lower median household income compared to the metropolitan average
- Inconsistent sidewalk continuity and variable street lighting on certain secondary blocks
Homelessness: Homelessness is minimal within the interior residential blocks, though unhoused individuals and occasional panhandling are observed near major intersections along Castroville Road and Highway 90.
What Winston Square is like at each time of day
- Morning · 5a – 11a
- Active and quiet as residents commute to work and students head to local schools.
- Afternoon · 11a – 5p
- Calm residential environment with standard neighborhood traffic and customers visiting local diners.
- Evening · 5p – 10p
- Streets quiet down quickly after sunset, and basic caution is advisable along commercial edges.
- Late night · 10p – 5a
- Streets are largely deserted; walking alone late at night is discouraged due to dim lighting and opportunistic crime risks.
Transit, parking and getting around
VIA Metropolitan Transit serves the neighborhood via bus routes such as Route 62 and Route 68, providing connections along Castroville Road to Centro Plaza and downtown San Antonio.
Street parking is free and readily available throughout residential streets, and area strip centers feature open surface parking lots.
Things to do in Winston Square
- Sample authentic Mexican breakfast tacos and traditional pan dulce along Castroville Road
- Attend concerts, esports tournaments, or tech exhibits at the nearby Boeing Center at Tech Port
- Enjoy community green space and walking paths at nearby Collins Garden Park
Local favorites
- Taqueria Chapala Jalisco · Mexican Restaurant · 4.3★ (1150)A casual local staple known for hearty breakfast plates, enchiladas, and fresh salsa.
- La Popular Bakery · Bakery · 4.4★ (420)Longstanding neighborhood panaderia serving fresh conchas, empanadas, and Mexican pastries.
- Boeing Center at Tech Port · Event Venue & Arena · 4.6★ (1280)Modern entertainment complex and esports arena hosting major concerts, expos, and community events.
Neighborhoods near Winston Square
Common questions about Winston Square
Is Winston Square safe to walk at night?
Take care after dark: stick to lit main streets or take a ride.
Is Winston Square a good place to live?
On safety, Winston Square scores 61/100 — below average, so visit at different times of day before deciding to move.
How walkable is Winston Square?
Walk score 42/100 and bike score 41/100. Most trips need a car.
Which areas near Winston Square are safer?
Lackland AFB (84), Vista Point (80) score higher nearby.
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