Bought at $1.2M, Marketed at $2.5M, Asking $2.0M: Flip Post-Mortem on 6 Ivy Circle, Winchester
A 1966 shell bought after 233 days on market, gut-renovated and expanded, then cycled through three brokerages and four MLS legs with $499,000 in ask cuts — while Winchester kept closing similar homes north of $2.2M.
6 Ivy Circle in Winchester's Flats neighborhood is a flip post-mortem in plain sight: bought for $1,200,000 in January 2024 after a bruising prior listing, marketed as a gut-renovated six-bedroom colonial, then launched at $2,499,000 in June 2025 and cut to $2,000,000 under a new Engel & Völkers MLS in April 2026. The market is not rejecting Winchester. It is rejecting this price ladder, this square-footage story, and this brokerage churn.
Bottom line up front — this is a flip post-mortem, not a teardown story
The current owners bought the tired house for $1,200,000 on January 19, 2024, marketed it after a gut renovation (listing copy: barn-board family room, six bedrooms, spa baths), and have spent roughly 14 months trying to resell it — without a reported closing on the renovated product as of our May 28, 2026 research.
What failed was not Winchester. Our fall 2025 Winchester sales work showed a ~$1.90M median and active $2.2M–$2.7M trades on similar renovated footage. What failed was the flip economics narrative: anchor too high ($2,499,000), brokerage and MLS resets that signal distress, and a square-footage / assessor story that still reads like two different houses.
Correction note: An earlier BMAS micromarket brief described this parcel as a full teardown and new build. MLS and syndicated listing data now consistently describe a gut-renovated 1966 shell with year renovated 2024. This post follows the reno-and-resell evidence trail.
📋Verified facts — property snapshot
| Field | Value | Source |
|---|---|---|
Address | 6 Ivy Cir, Winchester MA 01890 | MLS / Zillow |
Neighborhood | The Flats (Winchester Highlands) | MLS 73440674 syndication |
Lot | ~0.24 ac (~10,350 sf) | Listing / tax records |
Year built | 1966 | MLS / Compass tax card |
Year renovated (marketing) | 2024 | Compass listing tax card |
Prior shell (at 2024 sale) | 3 bed / 2.5 bath / ~2,307 sf | Realtor.com property history |
Current marketing | 6 bed / 5 bath / 3,403–3,728 sf | MLS 73510713 / 73440674 syndication |
Last sale | $1,200,000 — Jan 19, 2024 | MLSPIN / public deed syndication |
Current ask | $2,000,000 | MLS 73510713 — listed Apr 30, 2026 |
Current listing team | Engel & Völkers Boston (Post Advisory Group, Owen Russell) | MLS 73510713 |
FY2025 total assessment | $1,545,200 | Realtor.com / Coldwell Banker tax table |
FY2025 land / building split | $1,017,300 land + $527,900 building | Tax history syndication |
FY2025 property tax | $17,136 | Active listing |
Realtor.com AVM (stale profile) | ~$2,187,821 on 2,307 sf footprint | Realtor.com — portal lag |
Square footage is the silent deal-killer
| Source | Finished SF | Implied $/sf at $2.0M ask |
|--------|-------------|---------------------------|
| Pre-2024 sale / tax estimator | 2,307 | $867 (misleading — old footprint) |
| Engel & Völkers MLS 73510713 | 3,403 | $588 |
| Blue Ocean MLS 73440674 | 3,728 | $536 |
| Compass tax card detail | 3,134 above grade + 457 basement | ~$588 on above-grade only |
At $2.0M, a jumbo buyer's appraiser will not use Zillow's 2,307 sf profile — but they will ask whether 3,403 or 3,728 matches the occupancy permit and assessor sketch. Until that reconciles, every offer dies in underwriting.
Flip lesson: Renovators who expand GLA without locking one audited number across MLS, assessor, and permit records export their margin problem to the buyer.
🛒Act I — How the flip started (2023–2024 acquisition)
| Date | Event | Price |
|---|---|---|
May 31, 2023 | Listed | $1,449,000 |
Jun 13, 2023 | Price cut | $1,375,000 |
Aug 11, 2023 | Price cut | $1,325,000 |
Sep 6, 2023 | Price cut | $1,315,000 |
Oct 17, 2023 | Price cut | $1,265,000 |
Dec 15, 2023 | Under agreement | $1,265,000 |
Jan 19, 2024 | Sold | $1,200,000 |
233 days from first list to deed. The seller gave up $249,000 off the opening ask — classic dated-colonial discount in a strong town.
Our land-share work at the $1.2M transaction implied ~76% improvement / ~24% land — buyers were paying mostly for the 1966 structure and location, not trophy finishes. That is exactly the profile investors target for gut-renovation plays: buy the seller's exhaustion, not the seller's pride.
Verified: sale price $1,200,000 vs $1,545,200 FY2025 total assessment today — the assessment reflects post-renovation lag, not the 2024 economics. At closing, the sale was ~0.78× the then-assessed value (per our Winchester micromarket research), consistent with land-heavy pricing on a tired house.
🔨Act II — Renovation economics (directional, not audited)
We did not pull building permits or contractor invoices for this post. The renovation scope is inferred from MLS marketing (gut-renovated colonial, vaulted barn-board family room, six bedrooms, lower-level recreation with patio sliders, new kitchen with large island).
Directional all-in model for investors:
| Line item | Low | High | Notes |
|-----------|-----|------|-------|
| Acquisition (Jan 2024) | $1,200,000 | $1,200,000 | Verified deed |
| Gut reno + expansion to ~3,400–3,700 sf | $450,000 | $750,000 | Greater Boston interior-ring custom band; scope-dependent |
| Carry (26 mo @ taxes, insurance, debt service) | $80,000 | $150,000 | Illustrative — actual debt terms unknown |
| Selling costs at $2.0M (6%) | $120,000 | $120,000 | Broker + transfer friction |
| Implied breakeven band | ~$1.85M | ~$2.22M | Before profit |
Forensic read:
- At $2,499,000 (June 2025 launch), the seller was implicitly targeting ~25–40%+ gross margin over a realistic all-in — ambitious but not insane if the finish quality matched Rangeley / Harrison comps.
- At $2,000,000 (April 2026), the seller is near breakeven or underwater on a generous reading — and still not closed.
The flip did not fail on construction category. It failed on exit pricing and go-to-market sequencing.
📉Act III — Resale marketing: four legs, three brokerages, $499K in cuts
| Date | Event | Ask |
|---|---|---|
Jun 17, 2025 | Listed | $2,499,000 |
Jun 25, 2025 | Price cut | $2,399,000 |
Aug 12, 2025 | Price cut | $2,299,000 |
Sep 1, 2025 | Listing removed | $2,299,000 |
~76 days on this leg before withdrawal — the market saw $200,000 in cuts and walked away.
| Date | Event | Ask |
|---|---|---|
Oct 7, 2025 | Listed | $2,250,000 |
Nov 1, 2025 | Removed | — |
Dec 4, 2025 | Relisted | $2,250,000 |
Mar 21, 2026 | Price cut | $2,150,000 |
Apr 1, 2026 | Removed | $2,150,000 |
Third-party sites showed 127+ days on market on this MLS number — a zombie-adjacent pattern (withdraw → relist → cut) in the same family as our 276 High St and 18 Middlesex St Winchester forensics.
| Date | Event | Ask |
|---|---|---|
Apr 30, 2026 | New MLS / new brokerage | $2,000,000 |
Brokerage churn — what buyers infer
1. Coldwell Banker Realty – Lexington (Corcoran Property Advisors footprint, MLS 73392129)
2. Blue Ocean Realty, LLC — Rose Hall (MLS 73440674)
3. Engel & Völkers Boston — Post Advisory Group & Owen Russell (MLS 73510713)
Sophisticated Winchester buyers read this as strategy drift, not exclusivity: new MLS for a fresh DOM clock, new photography, same barn-board story, lower number. That can work — but only when the price finally crosses the comp cluster. So far, it has not produced a deed.
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🏘️Winchester comps — the market cleared; this address did not
| Address | Sale date | Price | SF | $/sf |
|---|---|---|---|---|
6 Ardley Pl | Mar 2025 | $2,200,000 | 3,676 | $598 |
20 Elm St | Jul 2025 | $2,200,000 | 3,901 | $564 |
4 Winslow Rd | Aug 2025 | $2,215,000 | 3,607 | $614 |
17 Harrison St | Jul 2025 | $2,500,000 | 3,719 | $672 |
7 Rangeley Rd | Apr 2025 | $2,500,000 | 3,851 | $649 |
34 Rangeley Rd | Aug 2025 | $2,700,000 | 3,708 | $728 |
6 Ivy Cir (ask) | Apr 2026 | $2,000,000 | 3,403–3,728 | $536–$588 |
Post-mortem punchline: At $2.0M, Ivy is priced below several 2025 Winchester trades on similar square footage — not because the market is generous, but because the market already rejected higher anchors on this specific renovation.
Town context: Winchester post-sale analysis (Oct–Nov 2025) · Winchester town profile.
What the flipper got right: location (Flats cul-de-sac, schools, commuter access), product type (family-sized colonial), and scope (real expansion to six bedrooms).
What the flipper got wrong:
- Opening anchor at $670/sf on marketed GLA — above many closed Winchester trades.
- Slow cuts instead of resetting near $2.1M–$2.2M after the first failed leg.
- Brokerage musical chairs instead of one disciplined pricing committee.
- Leaving square footage ambiguous across portals while assessor building value still shows $527,900.
💰Tax reassessment — the next buyer's hidden invoice
FY2025 taxes: $17,136 on $1,545,200 total assessment — but the building line is only $527,900 while land is $1,017,300.
Massachusetts buyers know what comes next: a post-sale reassessment toward market value on a $2.0M+ transaction. Budget materially higher annual taxes than the listing card shows — a common flip exit surprise that erodes the buyer pool.
Assessor research: Winchester Patriot Properties (parcel search by address).
🎓Five flip lessons from 6 Ivy Circle
- •Buy the seller's timeline, not the town's median. The $1.2M purchase followed 233 DOM and five price cuts — good entry. The exit assumed top-of-town velocity — bad read.
- •One MLS, one price committee. Fresh MLS numbers reset DOM; they do not reset buyer memory in a small town.
- •Audit GLA before you photograph. Lock permit → assessor sketch → MLS to a single finished number before spending on staging.
- •Anchor to closed $/sf, not aspirational neighbors. Harrison and Rangeley prove $650+/sf exists — but those trades closed. This address has zero matching closes at any price.
- •Winchester forgives product, not price ladders. Schools and cul-de-sacs buy you showings, not blank checks.
⚖️Verified vs speculative
| Claim | Status |
|---|---|
Jan 19, 2024 sale at $1,200,000 | Verified (MLSPIN / Realtor.com syndication) |
2023–24 prior listing timeline and cuts | Verified (Realtor.com price history) |
Jun 2025–Apr 2026 resale timeline and prices | Verified (Realtor.com / Compass / boardwalk MLS scrape) |
Three brokerages / MLS 73392129, 73440674, 73510713 | Verified (listing syndication) |
FY2025 assessment and tax figures | Verified (tax history syndication) |
Gut renovation scope and 2024 renovation year | Verified (MLS marketing / Compass tax card) |
Renovation cost $450K–$750K and carry estimates | Speculative — illustrative Greater Boston bands |
Seller underwater vs modest profit at $2.0M | Speculative — depends on actual construction and debt |
Future clearance price ($1.85M–$1.95M scenarios) | Speculative scenario only — not a prediction |
🎯If you are the buyer — discipline checklist
- •Treat $2.0M as a starting point, not a gift — the seller has already cut 20% from peak ask.
- •Demand permit history, certificate of occupancy, and assessor sketch reconciled to marketed SF.
- •Model post-close reassessment — do not underwrite to $17,136 taxes.
- •Compare closed Winchester trades at $536–$588/sf, not Campaign A's $670/sf opening.
- •Read sibling forensics: 20 Amberwood Dr · Winchester buyer field guide.
- •Run structured underwriting: Evaluate.
Verdict — flip post-mortem
The town closed six-figure renovated colonials throughout 2025. This house expanded, restaged, repriced, re-brokered — and still could not find a deed. That is the definition of a post-mortem worth reading before you write the next gut-renovation pro forma in 01890.
Until square footage, taxes, and price converge on what Winchester buyers actually paid — not what the seller needed — you are not buying a bargain. You are buying someone else's margin problem.
Stress-test your Winchester number before you write the offer
Use Evaluate and the Winchester town profile to anchor discipline before flip staging hijacks your spreadsheet.
Run EvaluateDisclaimer: This analysis uses publicly available data for educational purposes only. It does not constitute investment, legal, or tax advice. Verify all MLS timelines, square footage, permits, and valuations independently. Consult qualified professionals before making real estate decisions.
Property data sourced from: MLSPIN syndication via Realtor.com, Compass, Coldwell Banker, Carey & Giampa (MLS 73440674), Zillow, BMAS Winchester micromarket research, and internal land-share calculations. Publication date: May 28, 2026.
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