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Houses for Sale in 1029 - DE Dempsey Milton

Showing results 1 - 30 of 42

Uncover the perfect place to call home in 1029 - DE Dempsey, Milton with Square Yards Canada. Refine your search by filtering properties based on age, price trends, and other criteria to find your best pick. Choose from a wide range of properties across 1029 - DE Dempsey, Milton real estate, offering various square footage options for all needs. Explore a detailed brochure of all houses for sale in 1029 - DE Dempsey, and pick from a range of popular amenities like swimming pools, parking facilities, gyms and more. With over 42 properties on offer, find various residential and commercial properties across 1029 - DE Dempsey, Milton. Navigate through MLS listings to know the top pick across 1029 - DE Dempsey, Milton.

Last Updated: September 26, 2026

40 Photos

1380 Main Street E, Halton, ON , MLS #W13457204 , Image - 1

Unit-303, 1380 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13457204

Residential Condo & Other (Condo Apartment)

$489000.0

Price drop by 5.8%

2 Beds
1 Baths
700-799 sq-ft

This very desirable 2 bedroom in Milton's popular Dempsey neighbourhood! This spacious & fantastic floor plan of open concept living space is suitable

36 Photos

1193 Knight Trail, Halton, ON , MLS #W13177090 , Image - 1

1193 Knight Trail 1029 - DE Dempsey, Milton, Halton, ON MLS® W13177090

Residential Freehold (Detached)

$1089000.0

4 Beds
3 Baths
2000-2500 sq-ft

Rarely Offered 3-Level Detached Gem in Prime Milton! Welcome to this impeccably maintained 4- bedroom family home, perfectly situated on a quiet, chil

46 Photos

276 Fitzgerald Crescent, Halton, ON , MLS #W13747818 , Image - 1

276 Fitzgerald Crescent 1029 - DE Dempsey, Milton, Halton, ON MLS® W13747818

Residential Freehold (Semi-Detached )

$889900.0

3 Beds
4 Baths
1500-2000 sq-ft

Prime location! One of the biggest highlights of this home is the unbeatable convenience it offers - situated just steps from a major shopping plaza w

Open House : Sun Sep 27, 12:00 PM to 05:00 PM

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1155 Davis Lane, Halton, ON , MLS #W13819440 , Image - 1

1155 Davis Lane 1029 - DE Dempsey, Milton, Halton, ON MLS® W13819440

Residential Freehold (Semi-Detached )

$929000.0

3 +1 Beds
4 Baths
1500-2000 sq-ft

Welcome to this spacious and beautifully maintained semi-detached home in the desirable community of Milton. Offering an ideal blend of comfort, funct

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

Pre-Construction

The Laurels

6100 Regional Road 25, Milton

From $506,990 - $795,990

Project Info

7 Buildings
1768 Units
Condos

Property Mix

1 Bed(1425)
2 Bed(343)

Developer:Mattamy Homes

36 Photos

164 Panton Trail, Halton, ON , MLS #W13746410 , Image - 1

164 Panton Trail 1029 - DE Dempsey, Milton, Halton, ON MLS® W13746410

Residential Freehold (Att/Row/Townhouse)

$775000.0

Price drop by 3.1%

3 Beds
4 Baths
1500-2000 sq-ft

Beautifully Maintained 3-Bedroom + Den Townhome in Northeast Milton! This inviting home offers an ideal blend of comfort and functionality on a quiet,

Open House : Sat Sep 26, 01:00 PM to 04:00 PM

35 Photos

71 Livingston Road, Halton, ON , MLS #W13697148 , Image - 1

71 Livingston Road 1029 - DE Dempsey, Milton, Halton, ON MLS® W13697148

Residential Freehold (Detached)

$979000.0

3 Beds
3 Baths
1500-2000 sq-ft

Welcome to this beautifully maintained three bedroom bungaloft ideally situated on a desirable corner lot in the sought-after Dempsey neighbourhood.

Open House : Sat Sep 26, 01:00 PM to 03:00 PM

29 Photos

166 Panton Trail, Halton, ON , MLS #W13671298 , Image - 1

166 Panton Trail 1029 - DE Dempsey, Milton, Halton, ON MLS® W13671298

Residential Freehold (Att/Row/Townhouse)

$809900.0

3 Beds
4 Baths
1100-1500 sq-ft

Welcome to an easy place to start your next chapter. Offering 1,445 sq. ft., 3 bedrooms, 2 full baths + 2 powder rooms and a single-car garage, this D

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

36 Photos

116 Dixon Drive, Halton, ON , MLS #W13826006 , Image - 1

116 Dixon Drive 1029 - DE Dempsey, Milton, Halton, ON MLS® W13826006

Residential Freehold (Detached)

$1389999.0

4 Beds
3 Baths
2500-3000 sq-ft

Welcome to 116 Dixon Drive, ideally situated in Milton's sought after Dempsey neighbourhood. This beautiful upgraded home offers a dynamic, open conce

16 Photos

1487 Maple Avenue, Halton, ON , MLS #W13820572 , Image - 1

Unit-401, 1487 Maple Avenue 1029 - DE Dempsey, Milton, Halton, ON MLS® W13820572

Residential Condo & Other (Condo Apartment)

$599900.0

2 Beds
2 Baths
1000-1199 sq-ft

Upscale 2-bedroom, 2-bathroom top floor condo in the heart of Milton. This stylish unit features a high ceilings open-concept layout, A large roomy ki

Open House : Sat Sep 26, 01:00 PM to 03:00 PM

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1390 Main Street E, Halton, ON , MLS #W13558296 , Image - 1

Unit-107, 1390 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13558296

Residential Condo & Other (Condo Apartment)

$469900.0

Price drop by 2.1%

1 +1 Beds
1 Baths
800-899 sq-ft

Welcome to Bristol on Main Condominiums! Ground floor unit facing park with a park view. Walk out patio from kitchen. BBQ allowed. Breakfast style cou

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

40 Photos

1350 Main Street E, Halton, ON , MLS #W13595384 , Image - 1

Unit-412, 1350 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13595384

Residential Condo & Other (Condo Apartment)

$599900.0

3 Beds
2 Baths
1200-1399 sq-ft

Beautiful And Rare 3 Bedroom 2 Bathroom (Approx 1400 Sqft) Penthouse Suite With Vaulted Ceilings. Beautiful Large Kitchen With Brown Cabinets, Brand N

41 Photos

1380 Main Street E, Halton, ON , MLS #W13822814 , Image - 1

Unit-210, 1380 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13822814

Residential Condo & Other (Condo Apartment)

$579100.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to this beautifully updated Corner Unit , offering approximately 1,020 sq. ft. ofbright, functional living space in a highly sought-after, com

26 Photos

1471 Maple Avenue, Halton, ON , MLS #W13820386 , Image - 1

Unit-302, 1471 Maple Avenue 1029 - DE Dempsey, Milton, Halton, ON MLS® W13820386

Residential Condo & Other (Condo Apartment)

$499000.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to this beautifully maintained 1,057 sq. ft. condo in a highly desirable, family-friendly Milton location near James Snow Pkwy and Main St E.

37 Photos

137 Fitzgerald Crescent, Halton, ON , MLS #W13738806 , Image - 1

137 Fitzgerald Crescent 1029 - DE Dempsey, Milton, Halton, ON MLS® W13738806

Residential Freehold (Detached)

$1139000.0

4 Beds
4 Baths
2000-2500 sq-ft

High Demand Location In Milton. Walking Distance To The Theatre, Shopping And Daycares. Minutes Away From The Highway And The Go Station. This 4 Bedro

45 Photos

214 Ellis Crescent, Halton, ON , MLS #W13782732 , Image - 1

214 Ellis Crescent 1029 - DE Dempsey, Milton, Halton, ON MLS® W13782732

Residential Freehold (Detached)

$1149900.0

4 +1 Beds
4 Baths
1500-2000 sq-ft

Welcome to 214 Ellis Crescent, a beautifully appointed 4+1 bedroom, 4-bathroom home offering an ideal blend of space, comfort and functionality in a d

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

49 Photos

1050 Main Street E, Halton, ON , MLS #W13699278 , Image - 1

Unit-114, 1050 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13699278

Residential Condo & Other (Condo Apartment)

$499000.0

1 +1 Beds
1 Baths
700-799 sq-ft

WOW -HOME SWEET HOME ! Welcome to the Prestigious Art on Main, where luxury meets lifestyle in this amazing layout of 744 square foot ground-floor res

26 Photos

1050 Main Street E, Halton, ON , MLS #W13795010 , Image - 1

Unit-403, 1050 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13795010

Residential Condo & Other (Condo Apartment)

$519000.0

2 Beds
2 Baths
800-899 sq-ft

Welcome To Suite 403 At Art On Main In Milton's Dempsey Neighbourhood. This Two-Bedroom, Two-Bathroom Condo Offers Southeast Exposure, One Underground

18 Photos

169 COOKE Crescent, Halton, ON , MLS #W13761438 , Image - 1

169 COOKE Crescent 1029 - DE Dempsey, Milton, Halton, ON MLS® W13761438

Residential Freehold (Detached)

$1149000.0

4 +1 Beds
4 Baths
2000-2500 sq-ft

Welcome to this bright and spacious 4+1 bedroom detached gem, perfectly tucked away on a quiet, family-friendly crescent within another crescent - sur

33 Photos

1460 Main Street E, Halton, ON , MLS #W13783270 , Image - 1

Unit-412, 1460 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13783270

Residential Condo & Other (Condo Apartment)

$419000.0

1 +1 Beds
1 Baths
800-899 sq-ft

Welcome to Penthouse Suite 412 at 1460 Main Street East in the highly desirable Dempsey neighbourhood of Milton. This bright and beautifully upgraded

43 Photos

1350 Main Street E, Halton, ON , MLS #W13428686 , Image - 1

Unit-301, 1350 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13428686

Residential Condo & Other (Condo Apartment)

$560000.0

2 Beds
2 Baths
1000-1199 sq-ft

Beautiful and spacious 1013 sqft end-unit 'Windsor' model offering 2 bedrooms, 2 bathrooms, and plenty of thoughtfully designed living space. Complete

44 Photos

1340 Main Street E, Halton, ON , MLS #W13752974 , Image - 1

Unit-113, 1340 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13752974

Residential Condo & Other (Condo Apartment)

$549900.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to 1340 Main Street #113 - a beautifully renovated 2-bedroom, 2-bathroom suite offering 1,184 sq. ft. of bright, comfortable living space in a

34 Photos

1471 Maple Avenue N, Halton, ON , MLS #W13803982 , Image - 1

Unit-110, 1471 Maple Avenue N 1029 - DE Dempsey, Milton, Halton, ON MLS® W13803982

Residential Condo & Other (Condo Apartment)

$399000.0

1 Beds
1 Baths
600-699 sq-ft

Welcome to this beautifully Freshly painted and Upgraded one-bedroom condo located in the vibrant Dempsey neighbourhood of Milton. Offering over 650 s

46 Photos

187 Cooke Crescent, Halton, ON , MLS #W13794070 , Image - 1

187 Cooke Crescent 1029 - DE Dempsey, Milton, Halton, ON MLS® W13794070

Residential Freehold (Detached)

$1149900.0

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to this beautifully maintained family home, ideally situated on a quiet street in Milton's sought-after Dempsey Park neighbourhood. Offering t

28 Photos

1321 Cartmer Way, Halton, ON , MLS #W13769722 , Image - 1

1321 Cartmer Way 1029 - DE Dempsey, Milton, Halton, ON MLS® W13769722

Residential Freehold (Att/Row/Townhouse)

$874000.0

3 +1 Beds
4 Baths
1500-2000 sq-ft

SEPARATE ENTRANCE to a FINISHED BASEMENT featuring a KITCHEN and FULL WASHROOM -an exceptional setup for extended family, guests or flexible additiona

38 Photos

1479 Maple Avenue, Halton, ON , MLS #W13691544 , Image - 1

Unit-206, 1479 Maple Avenue 1029 - DE Dempsey, Milton, Halton, ON MLS® W13691544

Residential Condo & Other (Condo Apartment)

$399900.0

Price drop by 11.1%

1 +1 Beds
1 Baths
700-799 sq-ft

Welcome to this spacious 1-bedroom + den condo in the highly sought-after Dempsey community of Milton! This freshly painted, carpet-free unit offers a

45 Photos

1239 Fox Crescent, Halton, ON , MLS #W13749700 , Image - 1

1239 Fox Crescent 1029 - DE Dempsey, Milton, Halton, ON MLS® W13749700

Residential Freehold (Detached)

$1399000.0

4 Beds
4 Baths
2500-3000 sq-ft

Original Owners, One Family Since New! Welcome To 1239 Fox Crescent, A Spacious 2,840 Sq Ft Detached Home In Dempsey, One Of Milton's Most Established

28 Photos

1360 Main Street E, Halton, ON , MLS #W13688850 , Image - 1

Unit-212, 1360 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13688850

Residential Condo & Other (Condo Apartment)

$599000.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to this beautifully maintained and thoughtfully designed **2-bedroom, 2-bathroom corner suite** in the highly sought-after **Dempsey** neighbo

32 Photos

248 Pettigrew Trail, Halton, ON , MLS #W13597254 , Image - 1

248 Pettigrew Trail 1029 - DE Dempsey, Milton, Halton, ON MLS® W13597254

Residential Freehold (Semi-Detached )

$879900.0

Price drop by 2.2%

3 Beds
3 Baths
1500-2000 sq-ft

Presenting 248 Pettigrew Trail - A great semi-detached home in Milton's desirable Dempsey neighbourhood, within walking distance to shopping, restaura

37 Photos

1340 MAIN Street E, Halton, ON , MLS #W13609428 , Image - 1

Unit-313, 1340 MAIN Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13609428

Residential Condo & Other (Condo Apartment)

$580000.0

Price drop by 7.2%

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to Bristol on Main. This bright premium corner suite offers 1193 sqft. It has a sought-after split 2 bedroom layout, 2 full bathrooms, 2 priva

25 Photos

1487 Maple Avenue, Halton, ON , MLS #W13617838 , Image - 1

Unit-307, 1487 Maple Avenue 1029 - DE Dempsey, Milton, Halton, ON MLS® W13617838

Residential Condo & Other (Condo Apartment)

$434900.0

Price drop by 5.5%

2 Beds
1 Baths
800-899 sq-ft

Welcome to Unit 307 at 1487 Maple Avenue, where comfort and convenience come together in the heart of Milton's sought-after Dempsey neighbourhood. Thi

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