Aerial view of homes near Derry Road and Thompson Road in Dempsey, Milton

REAL ESTATE AGENT

Dempsey

Discover homes for sale and expert real estate services in Dempsey

Dempsey Market Stats

$767K

Avg. Price

38

Active Listings

42

Avg. Days on Site

$900K - $1.8M

Local Price Range

Dempsey Market Pulse

Live Dempsey market data updated daily

Average Price

$767,480

6-month price trend

Active Listings

38

6-month inventory trend

42 days

Avg. time on market

$598

Avg. price per sqft

30

Walk Score

$900K - $1.8M

Price Range

About Dempsey

Rural Charm Meets Suburbia

Dempsey occupies Milton's semi-rural northern fringe, where suburban development meets rolling countryside and agricultural land. The neighbourhood offers larger lots, newer estate-style homes, and a peaceful atmosphere that feels far removed from the city. Country Heritage Park and surrounding natural areas provide a distinctive backdrop for residents who appreciate open space and rural character.

Who Lives Here:

Families seeking space and rural lifestyle enthusiasts. The neighbourhood attracts buyers wanting larger properties, privacy, and a quieter pace of life.

The Beaty Branch of the Milton Public Library in east Milton

Nearby Schools

  • •

    Milton District High School

    Public High School

  • •

    Bishop Reding CSS

    Catholic High School

  • •

    Hawthorne Village Public School

    Public Elementary

  • •

    St. Anthony of Padua Catholic School

    Catholic Elementary

Transit & Commuting

  • •Milton Transit bus service
  • •Highway 401 and Highway 25 access
  • •Milton GO Station within driving distance
  • •45-minute drive to Toronto Pearson Airport

Parks & Amenities

  • •Dempsey Community Park
  • •Country Heritage Park
  • •Nature trails and conservation lands
  • •Rural cycling routes
  • •Local farm markets
Joe Battaglia, Broker — Battaglia Team REMAX Realty Specialists

Joe Battaglia, Broker

30+ years in Dempsey & Mississauga · $531M+ sold · 5.0-star Google rating from 100 reviews

Market Trends

August 2026 Mississauga Market Report

Mississauga overall: avg. detached $1,275,221 · 36 days on market · -0.1% MoM

Available Listings in Dempsey

Browse the latest homes for sale in Dempsey

1379 Brandon Terrace - Townhouse for sale in Dempsey, Ontario
active
New

$849,000

1379 Brandon Terrace

3 beds3 baths1,500 - 1,999 sqft
1015 Borden Lane - Semi-Detached for sale in Dempsey, Ontario
active
New

$920,000

1015 Borden Lane

4 beds3 baths1,500 - 1,999 sqft
1050 Main Street Unit 114 - Condo for sale in Dempsey, Ontario
active
New

$499,000

1050 Main Street Unit 114

2 beds1 baths700 - 1,099 sqft
1319 Weller Cross - Detached for sale in Dempsey, Ontario
active

$1,049,900

1319 Weller Cross

3 beds4 baths1,500 - 1,999 sqft
116 Dixon Drive - Detached for sale in Dempsey, Ontario
active

$1,389,999

116 Dixon Drive

4 beds3 baths2,500 - 2,999 sqft
1491 Maple Avenue Unit 311 - Condo for sale in Dempsey, Ontario
active

$695,000

1491 Maple Avenue Unit 311

3 beds2 baths1,200 sqft
1380 Main Street Unit 210 - Condo for sale in Dempsey, Ontario
active

$579,100

1380 Main Street Unit 210

2 beds2 baths1,000 sqft
1487 Maple Avenue Unit 401 - Condo for sale in Dempsey, Ontario
active

$599,900

1487 Maple Avenue Unit 401

2 beds2 baths1,000 sqft
1471 Maple Avenue Unit 302 - Condo for sale in Dempsey, Ontario
active

$499,000

1471 Maple Avenue Unit 302

2 beds2 baths1,000 sqft
1155 Davis Lane - Semi-Detached for sale in Dempsey, Ontario
active

$929,000

1155 Davis Lane

4 beds4 baths1,500 - 1,999 sqft
1471 Maple Avenue Unit 110 - Condo for sale in Dempsey, Ontario
active

$399,000

1471 Maple Avenue Unit 110

1 beds1 baths600 sqft
187 Cooke Crescent - Detached for sale in Dempsey, Ontario
active

$1,149,900

187 Cooke Crescent

4 beds3 baths2,000 - 2,499 sqft
1460 Main Street Unit 412 - Condo for sale in Dempsey, Ontario
active

$419,000

1460 Main Street Unit 412

2 beds1 baths800 sqft
214 Ellis Crescent - Detached for sale in Dempsey, Ontario
active

$1,089,900

214 Ellis Crescent

5 beds4 baths1,500 - 1,999 sqft
169 COOKE Crescent - Detached for sale in Dempsey, Ontario
active

$1,149,000

169 COOKE Crescent

5 beds4 baths2,000 - 2,499 sqft
1340 Main Street Unit 113 - Condo for sale in Dempsey, Ontario
active

$549,900

1340 Main Street Unit 113

2 beds2 baths1,000 sqft
1239 Fox Crescent - Detached for sale in Dempsey, Ontario
active

$1,339,000

1239 Fox Crescent

4 beds4 baths2,500 - 2,999 sqft
276 Fitzgerald Crescent - Semi-Detached for sale in Dempsey, Ontario
active

$889,900

276 Fitzgerald Crescent

3 beds4 baths1,500 - 1,999 sqft
164 Panton Trail - Townhouse for sale in Dempsey, Ontario
active

$775,000

164 Panton Trail

3 beds4 baths1,500 - 1,999 sqft
1110 DAVIS Lane - Semi-Detached for sale in Dempsey, Ontario
active

$949,000

1110 DAVIS Lane

4 beds4 baths1,500 - 1,999 sqft
1471 Maple Avenue Unit 112 - Condo for sale in Dempsey, Ontario
active

$589,900

1471 Maple Avenue Unit 112

2 beds2 baths1,000 sqft
1208 Main Street Unit 103 - Condo for sale in Dempsey, Ontario
active

$648,800

1208 Main Street Unit 103

2 beds3 baths1,000 sqft
241 Featherstone Road - Detached for sale in Dempsey, Ontario
active

$834,900

241 Featherstone Road

3 beds3 baths1,500 - 1,999 sqft
71 Livingston Road - Detached for sale in Dempsey, Ontario
active

$979,000

71 Livingston Road

3 beds3 baths1,500 - 1,999 sqft
1479 Maple Avenue Unit 206 - Condo for sale in Dempsey, Ontario
active

$399,900

1479 Maple Avenue Unit 206

2 beds1 baths700 - 1,099 sqft
1208 Main Street Unit 201 - Condo for sale in Dempsey, Ontario
active

$699,000

1208 Main Street Unit 201

2 beds3 baths1,200 sqft
166 Panton Trail - Townhouse for sale in Dempsey, Ontario
active

$809,900

166 Panton Trail

3 beds4 baths1,100 - 1,499 sqft
1202 Main Street Unit 108 - Condo for sale in Dempsey, Ontario
active

$619,888

1202 Main Street Unit 108

2 beds3 baths1,000 sqft
1009 Woodward Avenue - Detached for sale in Dempsey, Ontario
active

$1,449,000

1009 Woodward Avenue

8 beds6 baths3,000 - 3,499 sqft
1487 Maple Avenue Unit 307 - Condo for sale in Dempsey, Ontario
active

$434,900

1487 Maple Avenue Unit 307

2 beds1 baths800 sqft
1479 Maple Avenue Unit 102 - Condo for sale in Dempsey, Ontario
active

$565,840

1479 Maple Avenue Unit 102

2 beds2 baths1,000 sqft
1340 MAIN Street Unit 313 - Condo for sale in Dempsey, Ontario
active

$580,000

1340 MAIN Street Unit 313

2 beds2 baths1,000 sqft
248 Pettigrew Trail - Semi-Detached for sale in Dempsey, Ontario
active

$879,900

248 Pettigrew Trail

3 beds3 baths1,500 - 1,999 sqft
1491 Maple Avenue Unit 401 - Condo for sale in Dempsey, Ontario
active

$569,000

1491 Maple Avenue Unit 401

2 beds2 baths1,000 sqft
1390 Main Street Unit 107 - Condo for sale in Dempsey, Ontario
active

$469,900

1390 Main Street Unit 107

2 beds1 baths800 sqft
1268 Newell Street - Semi-Detached for sale in Dempsey, Ontario
active

$895,000

1268 Newell Street

4 beds3 baths1,500 - 1,999 sqft
1350 Main Street Unit 301 - Condo for sale in Dempsey, Ontario
active

$560,000

1350 Main Street Unit 301

2 beds2 baths1,000 sqft
1050 Main Street Unit 405 - Condo for sale in Dempsey, Ontario
active

$459,900

1050 Main Street Unit 405

1 beds1 baths600 sqft

Frequently Asked Questions About Dempsey

Common questions about living in and buying real estate in Dempsey, Milton

Ready to Find Your Home in Dempsey?

The Battaglia Team is here to help you navigate the Dempsey real estate market with expert guidance every step of the way.

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