As of October 2026, Dempsey, Milton has 33 active properties for sale with a median list price of $619.9K, averaging 43 days on market. Inventory is low at 2.6 months of inventory, but homes are selling under their first asking price and prices aren't rising, so this is currently a balanced market.
Listings updated Oct 14, 7:02 PM EDT
Dempsey is a central-east Milton neighbourhood along Main Street East and Maple Avenue, known for its concentration of low-rise condos. Listings are about half condo apartments, with detached and semi-detached houses and townhouses on the residential streets. The listings below cover every property type.
For Sale
34
Asking Range
$349.9K–$1.4M
Median Asking
$609.9K
34 listings for sale in Dempsey
Current listings in Dempsey, Milton include 7 Detached from $834.9K–$1.4M, 5 Semi-Detached from $849K–$929K, 1 Freehold Townhouse from $809.9K, 3 Condo Townhouses from $600K–$699K, and 18 Condo Apartments from $349.9K–$695K.
Dempsey is convenient: Main Street East has shopping and services, the Milton Leisure Centre is nearby, Milton GO is a short trip west, and Highway 401 is close. It's popular with first-time buyers and downsizers who want a low-rise condo near amenities. Schools are run by the Halton public and Catholic boards.
What should buyers check?
For the low-rise condos, compare fees and reserve funds between similar buildings and check the status certificate. For houses and townhouses, check the age of roofs, furnaces and air conditioners.
Asking prices, days on market and inventory are current. Sold figures are for sales in September 2026.
Dempsey Real Estate Market
As of October 2026, Dempsey, Milton has 7 active detached homes for sale with a median list price of $1.1M, averaging 31 days on market. Inventory is low at 1.8 months of inventory, but homes are selling under their first asking price and prices aren't rising, so this is currently a balanced market.
Balanced market
1.8 months of inventory
Supply is low, but homes are selling under their first asking price and prices aren’t rising.
How we call the market
Inventory is low at 1.8 months of inventory, but homes are selling under their first asking price and prices aren't rising, so this is currently a balanced market. From July to September 2026, 12 detached homes sold, 1 seller took their home off the market without relisting and 11 came back at a lower price — a 92% sell-through. Over July to September 2026, homes sold for a median 93.1% of their first asking price, and the median sold price per square foot was down 3.4% from the same months a year earlier.
What we measure, over the last three full months
Months of inventory: homes for sale today, divided by the average number sold per month. Fewer months means less choice for buyers.
Sell-through: of the sellers whose listing ended, the share who actually sold. A seller who takes their home off the market and doesn’t list it again within 60 days counts as not selling. A home that comes off and goes back on (often a day later, at a lower price) counts as a price cut, not a seller giving up.
Sold vs. first asking price: what homes sold for, compared with the price they were first listed at. We follow a home back through any relists, because a relist starts a new MLS® listing and hides the earlier, higher price.
Price trend: the median sold price per square foot, compared with the same three months a year earlier.
How the call is made
Seller’s market: under 3 months of inventory, at least 70% sell-through, and homes selling for 98% or more of their first asking price or prices up from a year ago.
Buyer’s market: over 6 months of inventory, or under 50% sell-through (more sellers giving up than selling).
Balanced market: everything in between, including low inventory where sellers are cutting prices, relisting or pulling their homes.
Based on MLS® listings from TRREB. Area totals only. We don’t show a call when fewer than 10 homes sold in those three months. Relists are matched by address, so a home relisted under a differently written address counts as taken off the market. Private sales and listings not on MLS® aren’t included. This is a general guide to the area, not an appraisal or advice about a specific home.
Based on properties for sale & sold — rentals not included. Figures are a monthly rollup covering October 1–14, 2026 (month to date), refreshed with each MLS® sync — shown as of October 14, 2026.
Property Type
Bedrooms
Active Listings
7
Number of homes currently for sale in this area.
Median List Price
$1.1M
The middle asking price among active listings -- half are listed higher, half lower.
Median $ / Sqft
$511
Median list price divided by square footage, for comparing across different unit sizes.
Avg. Days on Market
31
Average number of days active listings have been on the market.
Dempsey, Milton market statistics, current as of October 14, 2026
Metric
Current
Active listings
7
Median asking price
$1.1M
Average days on market
31
Months of inventory
1.8 mo
Sales in August 2026
4
Sale-to-list ratio
96%
YoY median sold-price change
—
Price trend
Median asking price against median sold price, by month.
Median List Price
Median Sold Price
What actually sold
4 detached homes sold in Dempsey, Milton in August 2026 at a median of $1.0M. Sales closed at an average of 96% of asking price.
Closed sales — the figures above describe homes still on the market.
Median Sold Price (as of Aug '26)
$1M
The middle sold price among closed sales this period -- half sold for more, half for less.
Sold $ / Sqft (as of Aug '26)
$554
Median sold price divided by square footage, for comparing across different unit sizes.
Months of Inventory
1.8 mo
How long it would take to sell all current listings at the recent sales pace. Lower favors sellers, higher favors buyers.
Sales-to-New Ratio
100%
Homes sold this period as a share of new listings -- a higher ratio signals stronger demand.
Sale-to-List Ratio (as of Aug '26)
96%
Average sold price as a percentage of asking price. Above 100% means homes are selling over asking.
Based on a small number of sales (4) — figures may not reflect the broader market.
Free account. Sold prices are for registered members.
4 sold in August 2026 · median $1M · 96% of asking (based on a small number of sales — 4)
See the address, photos and exact sale price for every recent transaction, free with a registered account.
Aggregate estimates from TRREB MLS® data (PropTx feed). Deemed reliable but not guaranteed, and not an appraisal. Full terms.
Explore condos for sale in Dempsey, Milton. Browse building-level listings, pricing, amenities, suite sizes and market data for individual buildings in this neighbourhood.
Dempsey is in central-east Milton along Main Street East and Maple Avenue.
What condos are in Dempsey?
Mostly four-storey Sutherland buildings on Maple Avenue and Main Street East, plus Art on Main, a twelve-storey building.
How much do condos cost in Dempsey?
The Dempsey market report on this site shows current sold prices, updated monthly.
Miko Nalepa
Realtor® at The Condo Bar Real Estate · RECO #4737024
With 15+ years in real estate and a GTA West focus since 2016, Miko Nalepa is a Realtor® with Right At Home Realty, Brokerage, specializing in condos, townhouses, and detached homes across Mississauga, Oakville, Burlington, and Milton. The focus stays deliberately narrow -- four cities, not a Toronto-wide practice -- because that's what it takes to know individual buildings and blocks, not just neighbourhood names.
Miko Nalepa is also the creator of The Condo Bar, the data platform behind this site, tracking building-level sales history and live market reports across 450+ GTA West condo buildings so every recommendation starts with what comparable units actually closed for, not asking price.
Public, Catholic and French-language schools located in Dempsey. Your local school depends on your exact address, so check the board’s school finder before you buy.
School details come from the Ontario Ministry of Education and the school boards, and may change. Boundaries, programs and grades are set by each board and can change from year to year, so confirm with the board before you buy.
