Greater Boston · Town guide
Living in Winchester, MA.
A high-end suburb with two commuter rail stations, the Mystic Lakes, a walkable town center, and one of the highest medians of the towns I cover.
Winchester at a glance
- Median single-family
- $1,750,000
- ▼ 7.2% vs. last year
- Median condo
- $770,000
- ▼ 12.7% vs. last year
- Days on market
- 35
- single-family, year to date
- Sale vs. original list
- 99.1%
- single-family, year to date
- Residential tax rate
- $11.08
- per $1,000, FY2026
- Population
- 23,953
- 2024 Census estimate, +4.3% since 2020
- To Boston
- 8 mi
- straight line to City Hall
- MBTA rail & ferry
- Commuter rail
Winchester market · August 2026 year to date
The numbers, before the opinions.
| Measure | Single-family | Condo |
|---|---|---|
| Median sale price | $1,750,000 | $770,000 |
| Change vs. last year | ▼ 7.2% | ▼ 12.7% |
| Sales closed | 121 | 43 |
| Median days on market | 35 | 49 |
| Sale price vs. original list | 99.1% | 100.5% |
| For sale at month end | 34 | 8 |
| Months of supply | 2.3 | 1.5 |
Source: Massachusetts Association of REALTORS®, Winchester Local Market Update (PDF, opens in a new tab) (MLS PIN data). Year-to-date figures except homes for sale and months of supply, which are for the latest month. A town median is a starting point; the right price is street by street.
Side by side · August 2026 year to date
How does Winchester compare with nearby towns?
| Town | Median single-family | Median condo | Days on market | Tax rate (FY2026) |
|---|---|---|---|---|
| Winchester | $1,750,000 ▼ 7.2% | $770,000 | 35 | $11.08 |
| Stoneham | $860,000 ▼ 1.1% | $430,000 | 24 | $10.06 |
| Medford | $900,000 ▼ 2.7% | $691,750 | 31 | $8.63 |
| Melrose | $989,370 ▼ 1.1% | $550,000 | 23 | $11.47 |
| Malden | $725,000 ▲ 0.7% | $430,000 | 35 | $11.40 |
| Somerville | $1,375,000 ▼ 10.7% | $865,000 | 47 | $10.98 |
Year-to-date medians from each town's MAR Local Market Update; tax rates per $1,000 from the Mass. Division of Local Services. Nearby = closest town centers among the towns I cover.
Town guide
What it's like to live in Winchester.
What is it like to live in Winchester?
Winchester is leafy and residential, with a town center built around the train and the Aberjona River, the Mystic Lakes on its southern edge, and the Middlesex Fells nearby.
It's one of the most expensive suburbs north of Boston.
What are Winchester's neighborhoods like?
A quick orientation, not a ranking:
| Area | What it's like | Worth a look if you want |
|---|---|---|
| Winchester Center | Town center with shops, restaurants, and the train | Walkability |
| Wedgemere | Residential area with its own rail stop near the lakes | Rail access and the lakes |
| West Side | Large homes on hilly, wooded streets | Space and privacy |
| Near the Fells | Neighborhoods bordering the reservation | Trails and green space |
What does housing look like in Winchester?
Winchester is dominated by single-family homes, many large and older, with some condos near the center.
How is the commute from Winchester to Boston?
Winchester has two commuter rail stations on the Lowell Line, Winchester Center and Wedgemere. I-93 is nearby for drivers.
Where do people spend time in Winchester?
- The Mystic Lakes
- Winchester Center
- The Middlesex Fells
What should buyers and sellers know about Winchester?
- Inventory is limited at every price point.
- Older large homes need careful inspections and budgets.
For public school information, see the Massachusetts Department of Elementary and Secondary Education's school and district profiles (Winchester Public Schools).
Questions people actually ask.
Does Winchester have a train to Boston?
Yes. Winchester has two commuter rail stations, Winchester Center and Wedgemere, on the Lowell Line.
Why is Winchester expensive?
Limited inventory, larger homes, and a location close to Boston with rail access all support high prices.
MBTA stations in Winchester
- Commuter rail: Wedgemere, Winchester Center (Lowell Line)
Monthly cost calculator
What would a Winchester home cost per month?
Pre-filled with Winchester's median single-family price and its FY2026 tax rate. Change anything. This is an estimate for planning, not a loan quote.
How I help in Winchester
Three ways to start.
Buy in Winchester
What homes here actually sell for, what they cost to own, and an offer strategy you can defend.
Buying with XavierSell in Winchester
A price grounded in Winchester sales, a plan for what to fix, and a clear read on every offer.
Get a home valuationInvest in Winchester
Two- and three-families run as numbers: rents, expenses, financing, and condition.
Multifamily & investingQuick answers about Winchester.
What is the median home price in Winchester, MA?
The median single-family sale price in Winchester was $1,750,000 for August 2026 year to date, compared with $1,885,950 for the same period a year earlier. The median condo sold for $770,000. Source: Massachusetts Association of REALTORS® (MLS PIN data).
How fast are homes selling in Winchester?
Single-family homes that sold in Winchester during August 2026 year to date spent a median of about 35 days on market and sold for 99.1% of their original list price on average, according to MAR.
What is the property tax rate in Winchester, MA?
Winchester's FY2026 residential property tax rate is $11.08 per $1,000 of assessed value (Massachusetts Division of Local Services). On a home assessed at the median single-family sale price, that's roughly $19,390 a year; your actual bill depends on the assessed value.
Is there public transit from Winchester to Boston?
Yes. MBTA service in Winchester: commuter rail: Wedgemere, Winchester Center (Lowell Line). Check the MBTA's current schedules for times.
MLS listings
Winchester homes for sale right now.
Active and coming-soon listings in Winchester, through my Ruuster home search. Save a search to hear about new ones as they come on.
Search provided by Ruuster via HomeBase. Open the full Winchester search in a new tab (opens in a new tab). Listing information is deemed reliable but not guaranteed.
Buying or selling here?
Interested in Winchester?
Tell me what you're weighing: a street, a price range, a timeline. I'll send the recent sales that matter and what I'd watch for in Winchester specifically.
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Sources: market figures, Massachusetts Association of REALTORS®, Local Market Update (data: MLS PIN; © ShowingTime Plus); tax rate, Massachusetts Division of Local Services, Municipal Databank, Tax Rates by Class; population, U.S. Census Bureau, Vintage 2024 population estimates for cities and towns; stations, MBTA (V3 API); distance, OpenStreetMap Nominatim (town center); miles are straight-line to Boston City Hall. Numbers retrieved 2026-09-25.