Dempsey, Milton Neighborhood Guide
Overview text Dempsey is a centrally located and highly convenient neighbourhood in Milton, Ontario, situated near Main Street East and James Snow Parkway. Known for its proximity to shopping, transit, and major highways, Dempsey is a top choice for commuters, first-time buyers, and investors in the Greater Toronto Area. Developed in the early 2000s, the neighbourhood features a mix of detached homes, townhouses, and condos, offering a range of housing options at competitive price points. Its close proximity to Milton GO Station and Highway 401 makes commuting to Toronto and surrounding cities extremely convenient. Dempsey continues to attract strong demand due to its location, walkability to amenities, and long-term investment value. Buyers looking for convenience and accessibility consistently prioritize this area. As demand remains strong in central neighbourhoods like Dempsey, buyers and sellers are becoming more strategic. Top 1% REALTORS® at Modern Solution Realty have helped over 5,000+ clients, saving more than $20M+ in commission and providing over $8M+ in cashback incentives.
Average Home Prices in Dempsey
- Average Detached Price: $1,215,000
- Average Semi-Detached Price: $995,000
- Average Townhouse Price: $875,000
- Average Condo Price: $635,000
Source: neighbourhood averages compiled by Modern Solution Realty from MLS® sales data, last reviewed April 23, 2026. Prices are estimates for informational purposes only.
Just Listed in Dempsey
33 homes have come to market in Dempsey in the last 90 days. Here are the 8 newest.
- 1471 Maple Avenue 112, Milton — 2 bed, 2 bath, $569,888
- 276 Sherwood Road, Milton — 5 bed, 4 bath, $1,149,000
- 1350 Main Street E 105, Milton — 2 bed, 1 bath, $399,999
- 1390 Main Street E 107, Milton — 2 bed, 1 bath, $455,000
- 1491 Maple Avenue 401, Milton — 2 bed, 2 bath, $549,000
- 1311 Cartmer Way, Milton — 3 bed, 3 bath, $850,000
- 1479 Maple Avenue 102, Milton — 2 bed, 2 bath, $549,000
- 1380 Main Street E 112, Milton — 3 bed, 2 bath, $625,000
See all 33 new listings in Dempsey
Restaurants in Dempsey
Dempsey offers some of Milton’s most convenient dining options within walking distance.
- Montana’s BBQ & Bar
- Kelseys Original Roadhouse
- Swiss Chalet
- Sunset Grill
- Memphis BBQ & Wicked Wings
Shopping in Dempsey
One of Dempsey’s biggest advantages is direct access to major shopping.
- Milton Common
- Milton Mall
- Main Street East retail
Schools near Dempsey
- St. Peter Catholic Elementary School
- Chris Hadfield Public School
- Kings Christian Collegiate
Parks & Outdoors in Dempsey
Dempsey includes parks and green spaces within walking distance.
- Coates Neighbourhood Park
- Livingston Park
- Local trails
Arts & Culture in Dempsey
Residents enjoy nearby cultural and community amenities.
- FirstOntario Arts Centre Milton
- Milton Public Library
- Community events
Frequently Asked Questions
Where is Dempsey located?
Dempsey is a neighborhood located in Milton, Ontario, Canada.
What schools are in Dempsey?
Dempsey is served by schools including St. Peter Catholic Elementary School, Chris Hadfield Public School, Kings Christian Collegiate.
What parks are near Dempsey?
Popular parks near Dempsey include Coates Neighbourhood Park, Livingston Park, Local trails.
How much commission do I pay to sell a home in Dempsey?
Modern Solution Realty lists homes in Dempsey, Milton for a 1% listing commission — significantly less than the traditional 2.5% — with the same full service.
Do I get cashback when buying a home in Dempsey?
Yes. When you buy a home in Dempsey, Milton through Modern Solution Realty, you receive $5,000 cashback at closing.
Looking to buy a home in Dempsey, Milton? Browse Dempsey homes for sale or all Milton homes for sale with Modern Solution Realty's 1% listing commission and $5,000 buyer cashback.