Snow plowing in Winchester, MA: reserve your season pass
- 1 car$425
- 2 cars$550
- 3 cars or 75 ft+$750
12 plows included. $100 deposit holds your spot. Per plow: $55 / $70 / $95. We plow at 2 inches.
Winchester snow rules you should know
- Parking
- Winchester has no set winter dates. The Town Manager declares a parking ban after talking with the Police Chief and Public Works Director, at least two hours before enforcement, and it lasts until canceled. It covers town roads, including state roads under town control, and municipal lots. The fine is $75 per violation and cars may be towed.
- Sidewalks
- Residential and commercial owners must clear the sidewalk in front of their property within 24 hours of the end of a storm (Town Ordinance 7). If not, the town may inspect, issue a $100 citation and charge for Public Works to clear it.
- Alerts
- The town says it shares bans by radio, TV, internet, its website and social media. Its site has a Get Notified link (Everbridge) and a notifications subscription. Sign up or check.
Checked Oct 2026. Sources: townofwinchester.org/articles/snow-emergency-par, townofwinchester.org/articles/shovel-your-share
We are not the town. Rules change, so confirm with Winchester before a storm. All 43 towns: parking ban and snow emergency rules.
What the pass covers
- 12 plows for the season. Each plow is up to 6 inches of snow.
- We plow when 2 inches or more has fallen. What a 2-inch trigger means.
- You get a text when we start and when we finish.
Cost in Winchester
| Driveway | Season pass | Per plow |
|---|---|---|
| 1 car | $425 | $55 |
| 2 cars | $550 | $70 |
| 3 cars or 75 ft+ | $750 | $95 |
The pass costs less than paying per plow once you need about 8 plows. Pay $100 now, the rest on December 1. Per push or seasonal · Cost calculator
Plowing a driveway in Winchester
Winchester is a residential town north of Boston where many homes are single-family houses on their own lots. A valley runs through the middle, and the east side climbs into the wooded Middlesex Fells while the west side rises toward the Arlington and Lexington heights. Hillside lots mean drives with a slope, and snow slides and refreezes on them.
The town does not run a fixed winter parking ban. Instead, the Town Manager declares a ban when a storm is coming, with at least two hours of notice, and it stays until canceled. In a ban the whole town road network and the municipal lots are covered, and the fine is $75 per violation, with towing possible. Cars that stay off the street let plows get to the curb, which leaves a clean edge and a smaller bank where the plow turns into your drive.
Town ordinance also makes owners clear the sidewalk in front of their property within 24 hours of the end of a storm, with a $100 citation if it is missed. On a hill, that means a long walk and a steep apron to clear, so people often want the drive and the apron done together. After the town plow goes by the plow bank is heavy and wet, and on a steep drive it is smart to clear it before the next freeze. If your drive is long or steep, tell the plow service about the slope and the turn-around space so it can plan how to clear the whole drive.
Neighborhoods and areas we serve
- Winchester Center
- Wedgemere
- The HighlandsEastern hills near the Middlesex Fells.
- Myopia Hill
- The Plains
Good to know
- The town is split by a valley and rises steeply on the east into the wooded hills of the Middlesex Fells.
- The Aberjona River, Mystic Lakes, Wedge Pond and Winter Pond are in town.
- Main Street and Washington Street are the main roads; Woburn is the longest shared border.
- The ban rule excludes 85-123 Prospect Street.
How it works
Reserve
Pick your driveway size and pay the $100 deposit.
We confirm
We text you to confirm the driveway and where snow can go.
We plow at 2 in
You get a text when we start and when we finish.
Condos, landlords and small lots in Winchester
Own a triple-decker, a condo association or a small lot in Winchester? A season pass is for single homes. For buildings and lots we walk the site and send a written price. Landlords · Condo associations · Request a proposal
Questions about snow plowing in Winchester
How much does snow plowing cost in Winchester?
A season pass is $425 for a 1-car driveway, $550 for 2 cars and $750 for 3 cars or 75 ft+. Each covers 12 plows. Or pay per plow: $55, $70 or $95. The pass costs less once you need about 8 plows.
When do you plow in Winchester?
We plow when 2 inches or more has fallen, once the snow stops. We do not promise a clock time because storms and routes vary. You get a text when we start and when we finish.
What happens after 12 plows?
Plows after the 12th are billed at the per-plow price for your driveway size: $55, $70 or $95.
Does Winchester have a set winter parking ban?
No. The town dropped fixed dates and the Town Manager declares a ban for each storm, at least two hours before enforcement. The fine is $75.
Who has to shovel sidewalks in Winchester?
Both residential and commercial property owners, within 24 hours of the storm's end under Town Ordinance 7. A missed sidewalk can mean a $100 citation plus the cost of town clearing.
Can you plow a steep Winchester driveway?
Winchester's eastern and western edges rise into hills, so slopes are common. Tell us the slope and length when you ask for a quote so we can say if it fits.
Also plowing near Winchester
- Snow plowing in Woburn and Burlington and WilmingtonShares Winchester's longest border, to the north.
- Snow plowing in StonehamBorders Winchester to the northeast near the Fells.
- Snow plowing in MedfordBorders Winchester to the southeast.
- Snow plowing in ArlingtonBorders Winchester on the south with similar hilly residential streets.
All towns we serve · Before the first storm · Roof raking and ice dams