Cheltenham vs Winchester
Which is better to live in? (2026)
Cheltenham (South West) and Winchester (South East) are two UK areas home buyers and renters frequently weigh against each other. On our overall Area Score, Cheltenham rates 67/100 (grade C) and Winchester rates 68/100 (grade B). Winchester is the safer of the two on crime (48/100 versus 41/100). Cheltenham has the stronger schools, with 93% of nearby schools rated Good or Outstanding by Ofsted. Winchester works out cheaper for typical monthly household bills (~£433 versus ~£439). The full side-by-side breakdown of crime, schools, transport, affordability, broadband, environment and healthcare is below, followed by our verdict on which area fits which kind of buyer.
Cheltenham vs Winchester: Category Comparison
Our Verdict
Winchester leads in 5 of 8 categories, scoring higher for crime safety, affordability, broadband. That said, Cheltenham has the edge in schools and transport, making it a strong option depending on what matters most to you.
Frequently Asked Questions
Is Cheltenham or Winchester better to live in?
Winchester leads in 5 of 8 categories, scoring higher for crime safety, affordability, broadband. That said, Cheltenham has the edge in schools and transport, making it a strong option depending on what matters most to you.
Is Cheltenham safer than Winchester?
Winchester scores higher for crime safety (48/100) compared to Cheltenham (41/100). Scores are based on the Index of Multiple Deprivation crime domain.
Which has better schools, Cheltenham or Winchester?
Cheltenham has 15 schools within 3km, with 93% rated Good or Outstanding by Ofsted. Winchester has 13 schools nearby, with 69% rated Good or Outstanding.
Is it cheaper to live in Cheltenham or Winchester?
Estimated monthly bills are lower in Winchester (~£433/month) compared to Cheltenham (~£439/month). Bills include council tax, energy, water, broadband, and insurance estimates.
Related Comparisons
Data sources: Scores are estimated using pre-loaded data from MHCLG Indices of Deprivation, Ofsted/GIAS school ratings, DfT Transport Connectivity 2025, MHCLG council tax data, Ofgem energy price cap, and regional averages. For full live data from 20+ government sources, view the individual town reports. Data provided under the Open Government Licence v3.0.