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Houses for Sale in 1029 - DE Dempsey Milton

Showing results 1 - 30 of 45

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 45 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: August 11, 2026

39 Photos

1483 Maple Avenue, Halton, ON , MLS #W13659444 , Image - 1

Unit-401, 1483 Maple Avenue 1029 - DE Dempsey, Milton, Halton, ON MLS® W13659444

Residential Condo & Other (Condo Apartment)

$550000.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to 401-1483 Maple Ave, a bright top floor condo in Milton's desirable Dempsey neighbourhood offering 1,013 sq. ft. of comfortable living space

39 Photos

1190 Fox Crescent, Halton, ON , MLS #W13663716 , Image - 1

1190 Fox Crescent 1029 - DE Dempsey, Milton, Halton, ON MLS® W13663716

Residential Freehold (Detached)

$999000.0

3 Beds
3 Baths
1500-2000 sq-ft

A Dream Home for Modern Living Steps from All the Essentials! This exquisite approx 2000sqf Detached home offers an additional fully finished basement

46 Photos

187 Cooke Crescent, Halton, ON , MLS #W13564086 , Image - 1

187 Cooke Crescent 1029 - DE Dempsey, Milton, Halton, ON MLS® W13564086

Residential Freehold (Detached)

$1174900.0

4 Beds
3 Baths
2000-2500 sq-ft

Exceptional family home located on a quiet street, in the sought-after Dempsey Park neighbourhood in Milton a perfect blend of comfort, space, and eve

34 Photos

1471 Maple Avenue N, Halton, ON , MLS #W13661770 , Image - 1

Unit-110, 1471 Maple Avenue N 1029 - DE Dempsey, Milton, Halton, ON MLS® W13661770

Residential Condo & Other (Condo Apartment)

$449888.0

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

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

49 Photos

1050 Main Street E, Halton, ON , MLS #W13419448 , Image - 1

Unit-114, 1050 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13419448

Residential Condo & Other (Condo Apartment)

$520000.0

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

WOW ! What a beautiful layout ! Welcome to the Prestigious Art on Main, where luxury meets lifestyle in this amazing layout of 744 square foot ground-

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)

$610000.0

Price drop by 2.4%

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

39 Photos

1370 Main Street E, Halton, ON , MLS #W13555576 , Image - 1

Unit-205, 1370 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13555576

Residential Condo & Other (Condo Apartment)

$515000.0

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

Open concept Hampton model, 893 sq ft, in the Heart of Milton's Dempsey neighborhood. Just steps away from shopping, entertainment, and great schools

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

23 Photos

1202 Main Street E, Halton, ON , MLS #W13651452 , Image - 1

Unit-108, 1202 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13651452

Residential Condo & Other (Condo Townhouse)

$619888.0

2 Beds
3 Baths
1000-1199 sq-ft

Truly Refined Condo Living Awaits Inside This Absolutely Stunning & Incredibly Spacious End Unit Townhome, Nestled In The Heart Of Charming Milton! Th

37 Photos

137 Fitzgerald Crescent, Halton, ON , MLS #W13650572 , Image - 1

137 Fitzgerald Crescent 1029 - DE Dempsey, Milton, Halton, ON MLS® W13650572

Residential Freehold (Detached)

$1279900.0

4 Beds
4 Baths
1500-2000 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

34 Photos

1206 Main Street E, Halton, ON , MLS #W13648422 , Image - 1

Unit-211, 1206 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13648422

Residential Condo & Other (Condo Townhouse)

$670000.0

2 Beds
3 Baths
1200-1399 sq-ft

Welcome To This Stunning 2-Bedroom, 3-Bathroom Upper-Unit Stacked Townhouse, Offering Over 1,200 Sqft Of Thoughtfully Designed Living Space. With High

42 Photos

1009 Woodward Avenue, Halton, ON , MLS #W13642046 , Image - 1

1009 Woodward Avenue 1029 - DE Dempsey, Milton, Halton, ON MLS® W13642046

Residential Freehold (Detached)

$1449000.0

5 +3 Beds
6 Baths
3000-3500 sq-ft

RARE OPPORTUNITY: Detached 5+3 Bedroom Home with Two Separate Basement Suites & Outstanding Income Potential Set on a premium 45.77 ft frontage with a

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)

$460000.0

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

33 Photos

95 Waters Boulevard, Halton, ON , MLS #W13638566 , Image - 1

95 Waters Boulevard 1029 - DE Dempsey, Milton, Halton, ON MLS® W13638566

Residential Freehold (Att/Row/Townhouse)

$829000.0

3 Beds
4 Baths
1100-1500 sq-ft

Welcome to this beautifully renovated 3-bedroom, 4-bathroom townhome nestled in one of Milton's most family-friendly neighbourhoods. Thoughtfully upda

44 Photos

1340 Main Street E, Halton, ON , MLS #W13127190 , Image - 1

Unit-113, 1340 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13127190

Residential Condo & Other (Condo Apartment)

$545000.0

Price drop by 13.5%

2 Beds
2 Baths
1000-1199 sq-ft

TOTALLY RENOVATED! Welcome to Bristol on Main in Milton's highly sought-after Dempsey neighbourhood. This spacious 2-bedroom, 2-bathroom Cambridge Mod

37 Photos

1440 Main Street E, Halton, ON , MLS #W13593760 , Image - 1

Unit-303, 1440 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13593760

Residential Condo & Other (Condo Apartment)

$499900.0

Price drop by 12.3%

2 Beds
1 Baths
800-899 sq-ft

Welcome to this beautifully maintained 2-bedroom, 1-bathroom condo in The Courtyards on Main, a sought-after building built in 2017 and ideally locate

36 Photos

40 Dills Crescent, Halton, ON , MLS #W13619304 , Image - 1

40 Dills Crescent 1029 - DE Dempsey, Milton, Halton, ON MLS® W13619304

Residential Freehold (Detached)

$899000.0

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

Tucked into Milton's sought-after Dempsey neighbourhood,this detached two-storey residence offers 4+1 bedrooms, 4 bathrooms, and approximately 2,500 s

50 Photos

1479 Maple Avenue, Halton, ON , MLS #W13613602 , Image - 1

Unit-102, 1479 Maple Avenue 1029 - DE Dempsey, Milton, Halton, ON MLS® W13613602

Residential Condo & Other (Condo Apartment)

$565840.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to 1479 Maple Avenue, where condo living meets the feel of your own private retreat. This rarely offered 2-bedroom, 2-bathroom suite boasts ov

34 Photos

1460 Main Street, Halton, ON , MLS #W13599704 , Image - 1

Unit-412, 1460 Main Street 1029 - DE Dempsey, Milton, Halton, ON MLS® W13599704

Residential Condo & Other (Condo Apartment)

$499000.0

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

27 Photos

1479 Maple Avenue, Halton, ON , MLS #W13611594 , Image - 1

Unit-405, 1479 Maple Avenue 1029 - DE Dempsey, Milton, Halton, ON MLS® W13611594

Residential Condo & Other (Condo Apartment)

$534900.0

2 Beds
1 Baths
800-899 sq-ft

Executive premium apartment located in one of the most desirable areas of Milton. A perfect opportunity for first-time buyers or downsizers looking fo

43 Photos

1245 Newell Street, Halton, ON , MLS #W13599510 , Image - 1

1245 Newell Street 1029 - DE Dempsey, Milton, Halton, ON MLS® W13599510

Residential Freehold (Detached)

$949907.0

3 Beds
3 Baths
1500-2000 sq-ft

From the moment you arrive, you'll be drawn in by the timeless curb appeal of this beautiful white home, complete with a welcoming covered front porch

19 Photos

1491 Maple Avenue, Halton, ON , MLS #W13586246 , Image - 1

Unit-401, 1491 Maple Avenue 1029 - DE Dempsey, Milton, Halton, ON MLS® W13586246

Residential Condo & Other (Condo Apartment)

$569000.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to this beautifully maintained and spacious condo in a sought-after boutique building at 1491 Maple Ave, Unit 401 in Milton. Offering over 1,0

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 )

$899900.0

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

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

31 Photos

1491 Maple Avenue, Halton, ON , MLS #W13585540 , Image - 1

Unit-111, 1491 Maple Avenue 1029 - DE Dempsey, Milton, Halton, ON MLS® W13585540

Residential Condo & Other (Condo Apartment)

$729000.0

3 Beds
2 Baths
1200-1399 sq-ft

Welcome to this beautifully updated 3-bedroom, 2- full bathroom condo offering the perfect blend of space, style, and convenience. This bright and spa

22 Photos

1370 Main Street E, Halton, ON , MLS #W13419434 , Image - 1

Unit-309, 1370 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13419434

Residential Condo & Other (Condo Apartment)

$499900.0

2 Beds
1 Baths
700-799 sq-ft

Welcome Home to 1370 Main St in Milton! This 2 bedroom, 1 bath unit is VALUE ALL DAY!! Located in a Highly Coveted Neighbourhood in Milton, this unit

41 Photos

1380 Main Street E, Halton, ON , MLS #W13579722 , Image - 1

Unit-210, 1380 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13579722

Residential Condo & Other (Condo Apartment)

$589777.0

2 Beds
2 Baths
1000-1199 sq-ft

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

19 Photos

241 Featherstone Road, Halton, ON , MLS #W13141964 , Image - 1

241 Featherstone Road 1029 - DE Dempsey, Milton, Halton, ON MLS® W13141964

Residential Freehold (Detached)

$849900.0

Price drop by 2.3%

3 Beds
3 Baths
1500-2000 sq-ft

Welcome to 241 Featherstone Road, This 3 Bed, 3 Bath Detached Home is Located in Milton's Sought After Dempsey Neighbourhood. This Inviting 2-Storey R

43 Photos

1015 Borden Lane, Halton, ON , MLS #W13574612 , Image - 1

1015 Borden Lane 1029 - DE Dempsey, Milton, Halton, ON MLS® W13574612

Residential Freehold (Semi-Detached )

$970000.0

4 Beds
3 Baths
1500-2000 sq-ft

Welcome to this beautifully maintained 4-bedroom, 2.5-bathroom corner-lot semi-detached home in the highly sought-after Dempsey neighbourhood of Milto

28 Photos

1360 Main Street E, Halton, ON , MLS #W13569128 , Image - 1

Unit-212, 1360 Main Street E 1029 - DE Dempsey, Milton, Halton, ON MLS® W13569128

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

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Houses for Sale in 1029 - DE Dempsey Milton

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