Median Price
$1,395,000
$529/sqft
Schools
8.8/10
Great
Appreciation
3.8/10
Growth Potential
Commute
27 min
to Boston
Live Market Snapshot
Loading…Recently Sold in Winchester
View all 19 sales$2,409,000
Curated Median
19
Total Sales on Record
$1,280,000–3,500,000
Price Range
Well Under Median
$1,280,000
2 Eaton Ct
3bd2ba2,192 sqft
$584/sqftInvalid Date
Well Under Median
$1,620,000
10 Bonad Rd
4bd3ba2,233 sqft
$725/sqftInvalid Date
Under Median
$1,750,000
24 Hinds Rd
4bd3ba2,814 sqft
$622/sqftInvalid Date
Under Median
$1,700,000
29 Pilgrim Dr
5bd3ba3,271 sqft
$520/sqftInvalid Date
At Median
$2,600,000
47 Yale St
6bd5ba4,540 sqft
$573/sqftInvalid Date
At Median
$2,150,000
22 Hollywood Rd
5bd4ba3,136 sqft
$686/sqftInvalid Date
What Drives Prices in Winchester
Full breakdownDecomposition of the $1,395,000 median price into its underlying components.
Land Value$192,751 (14%)
Structure & Quality$610,376 (44%)
School Premium$224,876 (16%)
Access & Commute Premium$185,041 (13%)
Prestige & Stability Premium$181,957 (13%)
630
School Value Score
640
Overall Value Score
The Winchester Vibe
Family-focused, well-manicured lawns, youth sports central
Prestigious suburban community with excellent schools, family-friendly neighborhoods, and strong property values
Highlights
⚽ Youth sports leagues everywhere
🍂 Picture-perfect New England vibes
🏫 Top-tier public schools
🚆 Commuter rail to North Station
Who It's For
✓ Great for
- •Families with children
- •School district seekers
- •Suburban lifestyle
- •Long-term investment
⚠ Consider elsewhere if
- •You want nightlife
- •You're under 30
- •You hate minivans
Demographics
Population22,760
Median Age43.8
Median Household Income$207,721
Work from Home27.2%
Professional Sector75.6%
Insider Tips
- 1.Myopia Hill area is the most prestigious
- 2.Town center has surprisingly good restaurants
- 3.Property taxes are high but schools are worth it