Bought at $1.2M, Marketed at $2.5M, Asking $2.0M: Flip Post-Mortem on 6 Ivy Circle, Winchester

This is a textbook Winchester flip that mis-timed the exit: $1.2M in, ~$500K+ implied renovation spend, $2.499M anchor out of the gate, three brokerages and four MLS legs later the ask is $2.0M with no closing on the renovated product.

Investors underwriting Boston suburban flips, Winchester buyers wondering why a renovated cul-de-sac colonial keeps cutting, and agents who need a comp-anchored conversation about fresh MLS resets.

• •Jan 2024 acquisition $1,200,000 after 233 DOM and ~$249K off the 2023 list
• •Jun 2025–Apr 2026 resale: $2,499,000 → $2,000,000 (−$499K) across three brokerages
• •Finished-area syndication ranges 3,403–3,728 sf vs 2,307 sf on tax records
• •FY2025 assessment $1,545,200 — post-reno reassessment cliff for next buyer
• •Winchester closed $2.2M–$2.7M renovated colonials in 2025; subject still unsold at $2.0M