Citywide market data
Winchester housing
market report.
Citywide CRMLS inventory, recent sales, pricing signals, days on market, and buyer/seller context for all of Winchester.
CRMLS data retrieved 10/5/2026Inventory & demand
Winchester currently has 251 active and 83 pending listings. CRMLS reports 186 closed sales over the prior 90 days.
Pricing
The 90-day median closed price is $630,750. Median sold price per square foot is approximately $277.
Price reductions
39.4% of active records in the returned market set show a current list price below the original list price.
Market speed
Median active days on market is 34; recent closed listings show a median of 34 days.
30-day trend
CRMLS reports 60 closings in the latest 30-day period versus 71 in the preceding 30 days. Median closed-price change between those periods is 2.1%.
How to read the Winchester market
Citywide statistics provide direction, but neighborhood, price range, property type, condition, lot, upgrades, HOA structure, and micro-location can produce a different competitive environment.
For buyers
Winchester buyers should compare builder incentives, special-tax and HOA structures, lot size, commute routes, school assignment, surrounding development, and how much future construction may occur nearby.
For sellers
Winchester sellers may compete with nearby builder inventory as well as resale homes. Pricing should account for incentives, upgrades, lot premiums, landscaping, condition, and total monthly ownership cost.
Data source & methodology
Current active and pending CRMLS listings plus closed residential listing records for the stated city. Price, days-on-market, price-reduction and sale-to-original-list metrics are calculated from records returned by Trestle; approximate months of supply divides current active inventory by the average monthly closed-sale count over the prior 90 days.
Source: CRMLS via Trestle. Market statistics are informational and are not an appraisal.
See the market that applies to your property
Search active homes in Winchester or request a property-specific CMA.