Back to Essentials

13 Price Cycles and Still Waiting: 276 High St, Winchester MA

Under 1 min read
May 17, 2026
THE BOTTOM LINE

At $2,195,000 with 13 price cycles and an ask 54% above the Winchester town median, this listing appears to be chasing a buyer who hasn't shown up yet.

WHO NEEDS THIS

Anyone considering an offer — or a list — on a large Winchester Colonial above $2M should read this.

KEY INSIGHTS
  • Ask is 54% above the Winchester town median price
  • Price-per-sqft runs 19% below the town median rate
  • 13 listing cycles signal persistent market resistance
  • 41 days on market with no price raised after prior drops
  • Assessor values the home at $2,093,500 — 4.8% below ask
DO THIS NEXT

Run a price-per-square-foot analysis against fully renovated Winchester comparables before making any move.

Want the full analysis?

Read the complete 22-minute post with detailed insights and data.

Read Full Post