186 Closings, 206 Days, One Pattern: What Winchester's Last 12 Months of Sold Data Actually Tells Buyers
We parsed 186 Winchester single-family closings (3+ bed / 2+ bath) from June 2025 through June 2026 — $345M in volume, a $1.70M median, and a market where 80% of homes sat 60+ days before selling. Here is the buyer playbook the headlines miss.
Winchester's trailing-year sold dataset (186 closings, $345M volume, median $1.70M) reveals a patient, tiered market: 38% of sales landed between $1.2M and $1.8M, only 16% closed under $1.2M, and the median home took 206 days to sell. We built a four-factor town diagnostic (liquidity, entry affordability, price premium, assessment gap) and applied it to 01890 — with comp tables, velocity patterns, and the $/sqft spreads worth targeting.
BLUF: Winchester's trailing-year sold market in four numbers
This analysis covers every Winchester closing we captured in a Zillow sold scrape (3+ bedrooms, 2+ bathrooms, single-family) from June 2025 through June 2026. It is not a listing snapshot — it is what buyers actually paid, how long sellers waited, and where $/sqft clustered.
Method note: Sold prices were parsed from Zillow export fields (including $2.10M shorthand). Days-on-market reflects Zillow's counter at close, not MLS-only DOM. Use this as a pattern map — verify any specific comp on MLS/deed before offering.
🔍Pattern 1: Winchester is a tiered market, not a single price point
The most actionable insight from 186 closings is that Winchester transacts in distinct price bands, each with different buyer pools, $/sqft logic, and patience requirements.
Under $1.2M (16% of sales): The entry band — often smaller footprints, townhouses, or homes needing work. Median near $1.07M with $553/sf. Do not assume "Winchester" means one number; this tier is a different product than the $2M core.
$1.2M–$1.8M (38% of sales): The core family market — where most competing buyers actually live. Median $1.43M, $591/sf, 224-day DOM. This is the widest $/sqft spread in town and the best place to hunt for mispriced comps.
$1.8M–$2.5M (28%): Move-up and renovated stock. Median $2.10M but $537/sf (size starts to dilute per-foot pricing).
$2.5M+ (18%): Luxury and new construction. Five sales cleared $3.5M+; top close $4.45M on Rangeley Rd.
| Tier | Sales | Share | Median Price | Median $/Sqft | Median DOM |
|---|---|---|---|---|---|
Under $1.2M | 30 | 16.1% | $1.07M | $553 | 193 |
$1.2M–$1.8M | 71 | 38.2% | $1.43M | $591 | 224 |
$1.8M–$2.5M | 52 | 28.0% | $2.10M | $537 | 182 |
$2.5M–$3.5M | 28 | 15.1% | $2.90M | $553 | 232 |
$3.5M+ | 5 | 2.7% | $3.90M | $613 | 231 |
Buyer takeaway
⏱️Pattern 2: Liquidity is the surprise — this is not a 'seven-day close' town
Headline velocity stories (like 15 Wildwood St closing in 3 days at $2.10M) are real — but they are exceptions. Across 186 sales:
- 4.8% closed within 14 days
- 79.6% sat 60+ days before selling
- Median DOM: 206 days (~6.8 months)
That earns Winchester a liquidity grade of D in our town diagnostic model: sellers who price off aspiration rather than comps wait; buyers who can wait often win concessions.
DOM vs price (counter-intuitive): Stale listings (240+ days) did not always mean discounts — median price $1.68M vs $1.71M for fast (under 30 days) closings. Slow sales often reflect starting price too high, not weak demand. The negotiation window opens after day 90, not day 7.
| Address | Sold | DOM | $/Sqft |
|---|---|---|---|
15 Wildwood St | $2.10M | 3 days | $512 |
149 Horn Pond Brook Rd | $1.02M | 7 days | $438 |
6 Oakland Cir | $1.61M | 11 days | $488 |
12 Salisbury St | $3.10M | 11 days | $607 |
65 High St | $1.44M | 11 days | $542 |
2 Priscilla Ln | $2.65M | 14 days | $623 |
📐Pattern 3: $/sqft inverts with size — small homes carry the foot premium
Winchester's median $563/sf hides a size curve every buyer should internalize:
| Size band | Median price | Median $/sqft |
|---|---|---|
Under 2,500 sf | $1.22M | $604/sf |
2,500–3,500 sf | $1.61M | $565/sf |
3,500–5,000 sf | $2.20M | $536/sf |
5,000+ sf | $2.90M | $494/sf |
Translation: Comparing a 1,400 sf cape to a 5,500 sf new build on $/sqft alone will mislead you. The trophy $/sf outliers (30 Prospect St at $973/sf, 40 Sargent Rd at $865/sf) are small-footprint premium locations — not size-adjusted norms.
| Address | Sold | Size | $/Sqft | DOM |
|---|---|---|---|---|
30 Prospect St | $2.45M | 2,519 sqft | $973/sf | 178 DOM |
40 Sargent Rd | $1.29M | 1,492 sqft | $865/sf | 189 DOM |
82 Hillcrest Pkwy | $1.56M | 1,882 sqft | $829/sf | 158 DOM |
5 Wood Ln | $2M | 2,443 sqft | $819/sf | 143 DOM |
17 Mason St | $1.33M | 1,629 sqft | $816/sf | 350 DOM |
102 Hillcrest Pkwy | $1.43M | 1,755 sqft | $815/sf | 193 DOM |
🎯Pattern 4: Value hides in the core tier — low $/sf on large lots
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The lowest $/sqft sales in the $1.2M–$2.5M core were not "cheap houses" — they were large-footprint homes on generous lots where price divided by living area looks artificially low.
Examples from closed sales:
- 4 Aricia Ln — $1.66M on 5,361 sf ($310/sf, 224 DOM)
- 5 Azalea Rd — $2.0M on 6,232 sf ($321/sf)
- 107 Cambridge St — $2.35M on 5,824 sf ($404/sf)
These are not steals by default — they often mean older layouts, renovation backlog, or location trade-offs. But for buyers who care about land and square footage under roof, the core tier is where arithmetic diverges most from prestige-street marketing.
| Address | Sold | Size | $/Sqft | DOM |
|---|---|---|---|---|
4 Aricia Ln | $1.66M | 5,361 sqft | $310/sf | 224 DOM |
5 Azalea Rd | $2M | 6,232 sqft | $321/sf | 182 DOM |
58 Bacon St | $2.03M | 5,791 sqft | $351/sf | 193 DOM |
1 Fox Hunt Ln | $2M | 5,000 sqft | $400/sf | 226 DOM |
5 Squire Rd | $1.88M | 4,696 sqft | $400/sf | 98 DOM |
107 Cambridge St | $2.35M | 5,824 sqft | $404/sf | 287 DOM |
🏛️The Winchester Town Diagnostic Model
We codified this analysis into a four-factor town diagnostic (implemented in town-sales-diagnostic.ts for reuse on other towns). Each factor grades A–D from sold-data patterns — not vibes.
| Factor | Grade | What it means |
|---|---|---|
Liquidity | D | Median 206 DOM; 10.8% close in 30 days — patience required |
Entry affordability | C | 16% of sales under $1.2M — limited single-family entry |
Price premium | B | $563/sf median — inner-ring elite band |
Assessment gap | B | 1.15x sale-to-assessed — typical MA lag |
Composite buyer verdict: Winchester rewards buyers who anchor to closed sales, not list prices. The core $1.2M–$1.8M band drives 38% of volume with the widest $/sqft spread. Sub-$1.2M inventory is just 16% of closings — plan early or adjust to townhouse product.
📅Pattern 5: Seasonality — steady volume, softening medians in early 2026
Monthly closings held relatively steady (15–22 sales/month in full months), but median price drifted down from $1.89M (Q2 2025) to $1.52M (Q1 2026) before stabilizing near $1.66M in Q2 2026.
That is not a crash signal in a 186-sale sample — it reflects mix shift (fewer ultra-luxury closes in Q1) and buyer selectivity at the top. November 2025 logged only 7 closings (holiday thinness), not a market stop.
Practical timing: Listings that survive the winter and relist in spring often carry DOM baggage — a diligence opportunity if price finally reflects comp reality.
| Quarter | Closings | Median price |
|---|---|---|
2025 Q2 | 19 | $1.89M |
2025 Q3 | 52 | $1.67M |
2025 Q4 | 45 | $1.83M |
2026 Q1 | 30 | $1.52M |
2026 Q2 | 40 | $1.66M |
🛠️Buyer playbook: five rules from 186 closings
Five rules from 186 closings
- •Tier-first comping. Identify which price band you are in before opening Zillow photos. A $1.5M offer strategy has nothing to do with a $3.4M new build on Foxcroft.
- •Use DOM as leverage, not fear. Median 206 days means sellers who listed high are often ready to talk after 90–120 days — if you can wait.
- •Adjust $/sqft for size. Never compare a 1,500 sf sale to a 5,000 sf sale without a size curve.
- •Stress-test taxes. Median sale ran 115% of assessed value — budget for assessment catch-up after purchase.
- •Run the address, not the town. Winchester's spread from $310/sf to $973/sf in the same year proves town-level medians lie. Evaluate the specific house.
Evaluate a Winchester address against real closings
Compare any listing to sold comps, RAAM scoring, and town context — before you write the offer.
Open Property EvaluateExplore Winchester town profile
Schools, commute, demographics, and investment score — the context behind the sold-data patterns.
Winchester Town Profile_Data source: Zillow sold export for Winchester MA 01890 (3+ bed / 2+ bath filter), scraped June 12, 2026. Analysis and town diagnostic model by Boston Property Navigator. Not appraisal or legal advice — verify all figures on MLS/deed before contracting._
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