1029 - DE Dempsey Homes under $800,000

1029 - DE Dempsey Homes under $800,000

Welcome to the vibrant neighborhood of 1029 - DE Dempsey in Milton, Ontario, where charm meets convenience! Nestled in the heart of one of Canada's fastest-growing cities, this community offers an inviting atmosphere for families, young professionals, and retirees alike.

Dempsey is characterized by its picturesque streets lined with well-maintained homes, many of which are priced under $800,000. This makes it an excellent option for first-time homebuyers or those looking to downsize without sacrificing quality of life. The area boasts a mix of modern townhouses and cozy single-family homes, providing a range of choices to suit various lifestyles and budgets.

One of the standout features of Dempsey is its accessibility. With easy access to major highways and public transit, commuting to Toronto or nearby cities is a breeze. The neighborhood is also conveniently located near an array of amenities, including shopping centers, parks, and recreational facilities. Families will appreciate the proximity to reputable schools and childcare centers, ensuring that education is never far away.

For those who enjoy the outdoors, Dempsey offers numerous parks and green spaces, perfect for weekend picnics or evening strolls. The community is also known for its friendly atmosphere, making it easy to connect with neighbors and participate in local events.

In 1029 - DE Dempsey, you’ll find not just a home, but a welcoming community that embraces the best of suburban living. Discover your new beginning in this delightful neighborhood today!

Newest 1029 - DE Dempsey Homes under $800,000

1050 Main Street E Unit 405, Milton
$439,900
1 Beds ⋅ 1 Baths ⋅ W14154490 MLS
Welcome to Art on Main - Contemporary Condo Living in the Heart of Milton! Experience comfort, style, and convenience in this stunning 1-bedroom, 1-bathroom condo, perfectly situated in one of Milton's most desirable buildings. Featuring a bright and spacious open-concept layout with soaring 9+ ft smooth ceilings and laminate flooring throughout. The stylish kitchen features granite countertops, stainless steel appliances, and ample cabinetry, seamlessly overlooking the combined living and dining area. Step outside onto your oversized west-facing balcony, the perfect outdoor retreat to relax, entertain, and enjoy breathtaking sunset views. The generously sized primary bedroom features an impressive floor-to-ceiling window, filling the space with natural light while showcasing beautiful western views. Enjoy the convenience of 1 underground parking space and 1 locker. Art on Main offers an exceptional collection of boutique-style, resort-inspired amenities, including a state-of-the-art fitness centre, outdoor swimming pool, rooftop terrace with BBQ stations, library, and more!Location! Location! Location! Ideally situated within walking distance to Milton GO Station, schools, shopping, restaurants, parks, and everyday amenities, with easy access to major highways for a convenient commute. A fantastic opportunity to enjoy modern condo living, spectacular sunsets, and an exceptional lifestyle in the heart of Milton! Book your showing today!!

1050 Main Street E Unit 405, Milton
1204 Main Street E Unit 202, Milton
$499,000
2 Beds ⋅ 3 Baths ⋅ W14149794 MLS
**Location, Convenience & Modern Living - All in One!** Enjoy the best of Milton's desirable Dempsey neighborhood, just minutes from Milton GO Station, Highway 401, shopping, grocery stores, restaurants, schools, and parks. Everything you need is close by, making everyday living and commuting effortless! *** Step inside this beautifully upgraded 2-bedroom, 3-bathroom townhouse and discover a bright, spacious main floor featuring elegant upgraded flooring, stylish light fixtures, and custom window coverings. The open-concept living and dining area offers plenty of space to relax or entertain, while the modern kitchen features stainless steel appliances, ample cabinetry, and an oversized island. A convenient powder room and private balcony complete the main level. *** Upstairs, you'll find two generously sized bedrooms, including a spacious primary retreat with a walk-in closet and private 4-piece ensuite. A second full bathroom and convenient ensuite laundry add to the home's functionality. One owned underground parking space is also included. *** **Why compromise on space, style, or location?** Offering approximately 1238 sq. ft. of living space, thoughtful upgrades, and exceptional convenience, this move-in-ready home is an excellent opportunity for first-time buyers, downsizers, and investors.

1204 Main Street E Unit 202, Milton
1380 Main Street E Unit 306, Milton
$399,900
2 Beds ⋅ 1 Baths ⋅ W14141722 MLS
Fantastic Location in Milton's Dempsey Park Community! Welcome to this bright and inviting 1-bedroom plus den, 1-bathroom condo offering a functional open-concept layout designed for comfortable everyday living. The spacious combined living and dining area provides an ideal setting for relaxing or entertaining, with a walkout to a private balcony featuring convenient additional storage. The versatile den is perfect for a home office, study area, or extra living space. Enjoy the convenience of 1 underground parking space and 1 exclusive use of a locker. Ideally situated in a family-friendly neighbourhood within walking distance to schools, parks, shopping, restaurants, public transit, and everyday amenities. Just minutes to Milton GO Station and with easy access to Highway 401, this location is perfect for commuters. An excellent opportunity for first-time buyers, downsizers, or investors looking for comfort, convenience, and a desirable Milton location!

1380 Main Street E Unit 306, Milton
1471 Maple Avenue Unit 112, Milton
$569,888
2 Beds ⋅ 2 Baths ⋅ W14114164 MLS
**Main-Floor Convenience, Spacious Living & a Location That Connects You to Everything!** Discover the comfort and practicality of this bright, spacious 2-bedroom, 2-full-bathroom condo in a desirable Milton location. What makes this home stand out? The convenience of main-floor living - no elevators, no long hallways to navigate, just easy everyday access and outdoor space steps away. Step inside to a thoughtfully designed open-concept layout featuring a generous living and dining area, abundant natural light, and a cozy fireplace that adds warmth and character to the space. The functional kitchen offers ample cabinetry, generous counter space, and a convenient breakfast bar overlooking the living area - ideal for casual dining or entertaining. Both bedrooms are generously sized, including a spacious primary retreat with its own private ensuite, while a second full bathroom provides added comfort and flexibility for family members or guests. Complete with ensuite laundry and a dedicated parking space, this home offers the everyday essentials without compromise. Enjoy a location that puts convenience at your doorstep - minutes to Highway 401, Milton GO Station, parks, schools, shopping, restaurants, and a short drive to Toronto Premium Outlets. Whether you're entering the market, looking to simplify your lifestyle, or searching for an investment opportunity, this condo offers an appealing combination of space, accessibility, and location. **A wonderful opportunity to enjoy comfortable condo living without the hassle of high-rise living!** Some photos have been virtually staged to illustrate the potential of the space.

1471 Maple Avenue Unit 112, Milton
1350 Main Street E Unit 105, Milton
$399,999
2 Beds ⋅ 1 Baths ⋅ W14100656 MLS
Beautiful 898 sq ft end-unit offering a bright and spacious 1 bedroom plus den layout, perfect for comfortable everyday living or a stylish work-from-home setup. This thoughtfully designed condo features an inviting open-concept living and dining area that seamlessly connects to an eat-in kitchen equipped with stainless steel appliances and ample cabinetry. The generous primary bedroom provides excellent natural light, while the versatile den can easily function as a second bedroom, home office, guest space, or reading area. Updated hardwood flooring throughout enhances the modern feel of the unit, and in-suite laundry adds everyday practicality. The well-maintained interior makes this home truly move-in ready.Additional highlights include an owned underground parking space, a dedicated locker for extra storage, and access to a well-managed gym and clubhouse within the complex. The building offers ample visitor parking and a welcoming community atmosphere. Located in one of Milton's most desirable and commuter-friendly neighbourhoods, this home is just minutes from Milton GO Station, Hwy 401, James Snow Parkway, parks, shopping, restaurants, and everyday amenities. Whether you're a first-time buyer, down-sizer, or investor, this updated condo provides exceptional value, modern living, and an unbeatable location.

1350 Main Street E Unit 105, Milton
1390 Main Street E Unit 107, Milton
$455,000
2 Beds ⋅ 1 Baths ⋅ W14098514 MLS
Welcome to Bristol on Main Condominiums! Ground floor unit facing park with a park view. Walk out patio from kitchen. BBQ allowed. Breakfast style countertop. This is a well-established mid-rise condo community located in the Dempsey neighbourhood of Milton. Built by Sutherland Development and completed around 2012, amenities include: A Gym, The buildings share a central rec centre where residents enjoy access to a party/social room with kitchen and fireplace, fitness/exercise room and visitor parking. Den can be used as a second bedroom and is currently being used as one. An extra surface parking spot is available at no extra cost from management.Plenty of visitor parking. Minutes to HWY 401, transit at your door step. * NOTE * Unit is wheelchair accessible, wide doors on main level units.

1390 Main Street E Unit 107, Milton
1491 Maple Avenue Unit 401, Milton
$549,000
2 Beds ⋅ 2 Baths ⋅ W14094342 MLS
A stunning corner unit with an abundance of light, wonderful view and a vaulted ceiling are what seperates this unit from other condo in Milton! This Windsor model features approximately 1,020 sq ft of beautifully updated living space. This bright 2-bedroom, 2-bathroom 4th-floor unit features soaring 12-ft vaulted ceilings and has a wonderful spacious open concept floor plan and even features a cozy gas fireplace and high-end birch laminate flooring. The newly updated kitchen (2026) has new quartz counters, upgraded cabinetry, stainless steel appliances, and breakfast bar seating for four. Generous bedrooms with California shutters; primary includes a 4-piece ensuite. Additional features: ceramic flooring in entry and baths, upgraded baseboards. BONUS - enjoy peaceful pond views from your private terrace-perfect for morning coffee or evening unwind. This complex is very well-maintained and the building is quiet - amenitities include an exercise room, party room, and ample visitor parking.

1491 Maple Avenue Unit 401, Milton
1479 Maple Avenue Unit 102, Milton
$549,000
2 Beds ⋅ 2 Baths ⋅ W14086952 MLS
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 over 1,000 square feet of stylish, carpet-free living with direct walk-out access to green space, no elevators, no stairs, just effortless indoor-outdoor living. Perfect for pet owners, young families, or downsizers, enjoy the convenience of stepping right outside from your kitchen to open green space, ideal for morning coffee, kids at play, or your furry companion. Plus, no direct neighbours looking in means added privacy you don't often find in condo living. Inside, you'll find new laminate flooring throughout, updated bathrooms with modern vanities and flooring, and new window coverings that complete the fresh, move-in-ready feel. Love to entertain? BBQ with ease just steps from your door, or take advantage of the spacious party room located right across the green space. Stay active with access to the building gym, and enjoy the convenience of ample visitor parking, your own dedicated parking space, and a private locker. This is the one buyers wait for, easy living, exceptional layout, and a lifestyle upgrade all in one. Don't miss it!

1479 Maple Avenue Unit 102, Milton
1380 Main Street E Unit 112, Milton
$625,000
3 Beds ⋅ 2 Baths ⋅ W14086898 MLS ⋅ Bristol On Main BLDG.
THE CONDO THAT THINKS IT'S A BUNGALOW! Rarely Available Ground-Floor Suite In The Sought-After Bristol On Main - And It's Never Looked Better! Great Price To Enjoy The Feel Of A Bungalow But With Condo Lifestyle Peace Of Mind. This Bright And Spacious 'Stanford' Model Offers Approximately 1,350 Sq. Ft. Of Carpet-Free Living Space, Freshly Painted Throughout With A Brand New Kitchen Countertop And Updated Finishes That Make This Unit Truly Move-In Ready. The Open-Concept Living And Dining Area Is Generously Sized And Flows Seamlessly Into A Gorgeous Modern Kitchen Featuring A Breakfast Bar, Stainless Steel Appliances, Large Pantry, And Walkout To A Private Patio. Three Well-Proportioned Bedrooms Thoughtfully Laid Out - With The Primary Suite Positioned At The Opposite End Of The Unit From The Additional Bedrooms, Offering A Welcome Sense Of Privacy. The Primary Features A 4-Piece Ensuite And His & Hers Closets. A Second Full Bathroom Serves The Remaining Bedrooms With Ease. Ensuite Laundry, One Exclusive Locker, And Two Owned Underground Parking Spots Round Out This Exceptional Offering. Building Amenities Include An Exercise Room, Party/Meeting Room, Car Wash, Bbqs Allowed, And Ample Visitor Parking. Pets Permitted With Restrictions. Steps To Shops, Restaurants, Community Rec Centre, And Transit - With Quick Access To Hwy 401 And Moments To "Main St." Milton. Ideal For First-Time Buyers, Downsizers, Small Families, Or Investors. Quality Ownership Throughout - This One Won't Last!

1380 Main Street E Unit 112, Milton
1471 Maple Avenue Unit 302, Milton
$569,000
2 Beds ⋅ 2 Baths ⋅ W14034120 MLS
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. Enjoy easy access to Highway 401 and Milton GO Station, with shopping, restaurants, schools, parks, Walmart, and Real Canadian Superstore all just minutes away. The spacious open-concept layout offers comfortable living and dining areas, a modern kitchen with black appliances and breakfast bar, and a private balcony perfect for enjoying your morning coffee or evening outdoors.The generous primary bedroom features a large closet and private 4-piece ensuite, while the spacious second bedroom is ideal for a child, guest room, roommate, or home office. The unit also includes in-suite full-size laundry, an additional 3-piece bathroom, owned underground parking, and a private storage locker. Residents enjoy access to a fitness centre, spacious party/amenity room, and underground car wash. With water included in the condo fees, this is an excellent opportunity for first-time buyers, down-sizers, or investors looking for a spacious, well-maintained home in a convenient and growing Milton community.

1471 Maple Avenue Unit 302, Milton
1483 Maple Avenue Unit 414, Milton
$625,000
3 Beds ⋅ 2 Baths ⋅ W14032348 MLS ⋅ Maple Crossing Condos BLDG.
Welcome to Maple Crossing Condos, located in a family-friendly neighbourhood in Milton! This beautifully maintained 1,275 sq. ft. top-floor condo offers a wonderful combination of comfort, space, and convenience. Move-in ready and thoughtfully designed, this bright and spacious suite features an inviting open-concept layout with soaring vaulted ceilings and an abundance of windows that fill the home with natural light.The well-appointed kitchen offers ample cabinetry and plenty of storage, overlooking a generous dining area-perfect for everyday family meals and entertaining guests. The cozy living room features a charming gas fireplace and large windows showcasing peaceful views of the surrounding open green space, creating a warm and relaxing atmosphere.The spacious primary bedroom offers a private retreat complete with a walk-in closet and a 3-piece ensuite. The additional bedroom + den are generously sized, featuring lovely east-facing views and versatile space for family members, guests, or a home office. Ideally situated close to schools, parks, scenic walking trails, shopping, and everyday amenities, this fantastic location offers the perfect balance of peaceful living and urban convenience. Just minutes from Milton GO Station with easy access to major highways, commuting is a breeze. A wonderful opportunity to enjoy spacious, condo living in one of Milton's established communities. Welcome home!

1483 Maple Avenue Unit 414, Milton
1350 Main Street E Unit 301, Milton
$515,000
2 Beds ⋅ 2 Baths ⋅ W14029514 MLS
Beautiful and spacious 1013 sqft end-unit 'Windsor' model offering 2 bedrooms, 2 bathrooms, and plenty of thoughtfully designed living space. Complete with 1 owned underground parking spot (additional parking spot available for use), 1 locker, additional tenant parking, and ample visitor parking. This bright unit features a large open-concept living and dining area, ideal for both everyday living and entertaining. The eat-in kitchen is equipped with stainless steel appliances and offers a walkout to a private west-facing balcony-perfect for enjoying evening sunsets. The primary bedroom includes a private ensuite bathroom, while the second bedroom is generously sized and conveniently located near the main bath, making the layout ideal for guests, roommates, or a home office. Professionally painted (March 2026) with new luxury vinyl flooring (March 2026) and no carpet throughout, this unit is truly move-in ready. Additional highlights include in-suite laundry, Hunter Douglas window coverings, and an abundance of natural light throughout. Residents enjoy access to a well-maintained complex featuring a gym and clubhouse, providing added space for recreation and gatherings. Perfect for end users or investors alike. Unbeatable location - 2.2 km to Milton GO, 450 m to James Snow Parkway, 1.1 km to Hwy 401, 1.1 km to FirstOntario Arts Centre, Milton Public Library, and Dempsey Neighbourhood Park, 3.2 km to Milton Mall, 3.3 km to downtown Milton, 6.3 km to Milton District Hospital, and just a 9-minute drive to Toronto Premium Outlets. Surrounded by grocery stores, shops, and everyday conveniences.

1350 Main Street E Unit 301, Milton
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