Wellesley vs Winchester
On the six headline livability metrics, Wellesley and Winchester split the table evenly. This is a real tradeoff, not a ranking. Median homes in Winchester run roughly $240k cheaper than in Wellesley, about 15% less.
The two towns at a glance
Wellesley
Winchester
Head-to-head: every metric
| Wellesley | Winchester | |
|---|---|---|
| Headline | ||
| Livability index | 70 ✦ | 69 |
| Economics | ||
| Median home | $1.62M ✦ | $1.38M |
| Household income | $258k ✦ | $230k |
| Price ÷ income | 6.3× ✦ | 6× |
| Tax burden | 56 | 60 ✦ |
| Schools & Safety | ||
| Schools | 97 ✦ | 96 |
| Safety | 92 | 95 ✦ |
| Getting around | ||
| Commute to Boston | 25 min ✦ | 24 min |
| Walkability | 37 | 40 ✦ |
| Transit | 26 | 29 ✦ |
| Biking | 33 | 44 ✦ |
| Lifestyle | ||
| Dining | 64 ✦ | 60 |
| Nightlife | 36 | 38 ✦ |
| Arts & culture | 56 ✦ | 50 |
| Green space | 80 ✦ | 72 |
| Community | ||
| Diversity | 70 ✦ | 68 |
| Climate | 74 ✦ | 73 |
| 5-yr trend | 71 | 73 ✦ |
Clay = wins this metric. Direction matters: lower median home and shorter commute are better; everything else, higher is better.
Compare on your terms
These winners are based on a neutral, equal weighting of every metric. Your priorities are not neutral. Open Wellesley vs Winchester in the interactive atlas to tune schools, walkability, affordability, commute, and seven more dimensions, and watch the verdict change.
Stuck between Wellesley and Winchester?
I'm Gary Fikes, a licensed real estate agent at MP Signature Realty and the curator of this site. I've walked both towns. Tell me what matters most and I'll give you a straight answer within 1 business day. No auto-dialer, no spam, no resale.
About this comparison
Bay State Atlas ranks 194 Massachusetts towns using public data (Census ACS, MA DESE schools, Walk Score, MA Department of Revenue tax data, and the FBI UCR safety index) normalized to 0–100. Every weight is editable. This page is a static, indexable snapshot. The live tool is faster and lets you customize what counts.