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13 Price Cycles and Still Waiting: 276 High St, Winchester MA
Under 1 min read
•May 17, 2026THE 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.
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