1029 - DE Dempsey Homes under $800,000

1029 - DE Dempsey Homes under $800,000

Welcome to the charming neighborhood of 1029 - DE Dempsey, nestled in the vibrant city of Milton, Ontario. This delightful community is a hidden gem that perfectly balances suburban tranquility with urban convenience. Known for its friendly atmosphere and picturesque surroundings, Dempsey is a place where families thrive and individuals find their slice of paradise.

One of the standout features of the Dempsey neighborhood is its incredible accessibility. Residents enjoy proximity to major highways, making commuting to nearby cities, including Toronto, a breeze. The area is also well-served by public transit, ensuring that everything you need is just a short ride away.

Dempsey is rich in amenities, with a variety of shopping options, dining establishments, and recreational facilities nearby. Families will appreciate the abundance of parks and green spaces, perfect for weekend picnics, leisurely strolls, or outdoor activities. The community is also home to several reputable schools, making it an ideal location for families with children.

For those seeking affordable housing options, Dempsey offers a selection of charming homes under $800,000. Whether you’re a first-time homebuyer or looking to downsize, you’ll find a diverse range of properties that cater to different lifestyles and preferences. From modern townhouses to cozy single-family homes, there’s something for everyone in this welcoming neighborhood.

In summary, 1029 - DE Dempsey is more than just a location; it’s a community where you can create lasting memories and enjoy a high quality of life. Come explore the possibilities that await you in this delightful Milton neighborhood!

Newest 1029 - DE Dempsey Homes under $800,000

1050 Main Street E Unit 114, Milton
$499,000
2 Beds ⋅ 1 Baths ⋅ W13843362 MLS
HOME SWEET HOME - Welcome to the Prestigious Art on Main, where luxury meets lifestyle in this amazing layout of 744 square foot ground-floor residence. This 1+1 Bed is really like a 2 Bedroom place. The second room is very spacious and can be used as another bedroom or as your home office. This home has a rare privilege of direct outdoor access with a private large walkout patio having a gas hook for your very own BBQ unlike other units. A great addition for dining and entertaining. Carpet free through out, 10-foot ceilings and floor-to-ceiling south-facing windows with discreet privacy film bathe the space in natural light, complementing the beautiful open-concept design. The king-sized primary bedroom with a spacious layout. The enclosed den ideal as a second bedroom or executive home office. A chef inspired kitchen features quartz countertops, premium stainless-steel appliances, and a refined hardware. Custom-built dry bar with a stunning walnut waterfall counter and built-in beverage chiller. Upgrades include in-suite laundry, designer lighting, and a spa-like 4-piece bathroom. High end executive style amenities, including a pet spa, guest suites, heated outdoor pool, steam room, state-of-the-art fitness centre, rooftop terrace, library, events room with chef's kitchen, party lounge, games room, and ample visitor parking. Perfectly positioned across from the Milton Public Library and mere minutes from the GO Station, top-rated schools, parks, boutique shops, restaurants, hospital, and major highways. This exquisite suite offers an a blend of convenience, comfort, and contemporary luxury that you don't want to miss !

1050 Main Street E Unit 114, Milton
1491 Maple Avenue Unit 311, Milton
$695,000
3 Beds ⋅ 2 Baths ⋅ W13823218 MLS
Welcome to this 1,240 sq.ft. beautifully updated 3-bedroom, 2-bathroom condo offering the perfect blend of style, comfort, & convenience for low maintenance living. Step inside to discover a bright & spacious open concept living & dining area with new flooring throughout. The heart of this home is a newly renovated eat-in kitchen featuring granite countertops, stylish backsplash, sleek stainless steel appliances & ample cabinetry - ideal for home cooks & families alike! Enjoy your morning coffee or unwind at the end of the day on the oversized private balcony. Retreat to 3 generous bedrooms, including a primary suite with its own full bathroom, while a second full bathroom provides convenience for guests & family. In-suite laundry, forced air gas heat, A/C & wired for Bell Fibe plus 1 owned underground parking spot & storage locker for added convenience. Located in the vibrant, sought-after Dempsey neighborhood, this condo is just minutes from highway 401, the GO station, top-rated shopping, dining, schools & parks - offering everything you need right at your doorstep. Access to club house w/ party room, underground car wash & gym on-site. Don't miss this opportunity to own a stylish, move-in-ready home in an unbeatable location!

1491 Maple Avenue Unit 311, Milton
1380 Main Street E Unit 210, Milton
$579,100
2 Beds ⋅ 2 Baths ⋅ W13822814 MLS
Welcome to this beautifully updated Corner Unit , offering approximately 1,020 sq. ft. ofbright, functional living space in a highly sought-after, commuter-friendly community. Thiswell-maintained 2-bedroom, 2-bathroom home features an open-concept layout with large windowsthat fill the space with natural light.Recent updates include new flooring throughout (2020), tile flooring in the kitchen and frontentrance, modern kitchen cabinets (2019), newer kitchen appliances (2019), an updated sink andtoilet in the second bathroom, and new laundry machines (2025) with warranty.Ideally located just a short walk to the GO Station and less than 3 minutes to Highway 401,this home offers exceptional convenience for commuters. Enjoy being within walking distance toparks, schools, shopping, restaurants, Go Station and other everyday amenities.Whether you're a first-time home buyer, downsizer, or investor, this move-in-ready home offersoutstanding value, comfort, and location. Don't miss this fantastic opportunity to own abeautifully updated home in a desirable neighbourhood!

1380 Main Street E Unit 210, Milton
1487 Maple Avenue Unit 401, Milton
$599,900
2 Beds ⋅ 2 Baths ⋅ W13820572 MLS
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 kitchen with a breakfast counter and contemporary cabinetry and ensuite laundry. Combined living/dining room features a gas fireplace. Two spacious bedrooms and two full bathrooms. One indoor parking included. Enjoy your morning coffee on your private terrace. Building offers nice amenities: party room and gym. Located just minutes from shopping, dining, parks, and public transit, this condo offers the best of urban living with easy access to all of Milton's amenities.

1487 Maple Avenue Unit 401, Milton
1471 Maple Avenue Unit 302, Milton
$499,000
2 Beds ⋅ 2 Baths ⋅ W13820386 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, downsizers, or investors looking for a spacious, well-maintained home in a convenient and growing Milton community.

1471 Maple Avenue Unit 302, Milton
1471 Maple Avenue N Unit 110, Milton
$399,000
1 Beds ⋅ 1 Baths ⋅ W13803982 MLS
Welcome to this beautifully Freshly painted and Upgraded one-bedroom condo located in the vibrant Dempsey neighbourhood of Milton. Offering over 650 sq ft of functional living space, this home is ideal for first-time buyers, commuters, or investors. The kitchen features dark, elegant cabinetry and generous storage. The bright open-concept layout flows into a spacious living area with a walk-out to a private balcony looking over a greenery open space with a pot lights with a droop ceiling all over the living room, and upgraded light fixture with smart light switch. The primary bedroom includes a large closet and ample natural light. A full 3-piece bathroom and in-suite laundry add comfort and convenience. This well-managed building offers excellent amenities including a gym, party room/club house and visitor parking. The Maple Crossing Condominiums Sought After By Commuters & Those Seeking Convenience At Their Doorstep. You'll Be Down The Street From Hwy 401, Milton Go, Starbucks, Restaurants, Milton Cineplex Theater, Grocery Stores & More. This Ground-Floor Unit Provides Convenient Outside Access & A Private Balcony, You'll Enjoy All The Extras Here, Underground Parking With Car Wash Bays, A Separate Storage Locker - Great For All Of Your Seasonal Belongings, This Is A Wonderful Opportunity & Overall Tremendous Value For Anyone Downsizing, Investing, Or First-Time Buyers Looking For Affordable Real Estate. We're Delighted To Present You To 1471 Maple Ave & Welcome You To Visit Today!

1471 Maple Avenue N Unit 110, Milton
1460 Main Street E Unit 412, Milton
$419,000
2 Beds ⋅ 1 Baths ⋅ W13783270 MLS
Welcome to Penthouse Suite 412 at 1460 Main Street East in the highly desirable Dempsey neighbourhood of Milton. This bright and beautifully upgraded 1-bedroom plus den, 1-bathroom condo offers 810 sq. ft. of stylish, open-concept living space with soaring 10-foot ceilings and expansive windows that fill the home with natural light. The spacious kitchen is a standout feature, boasting granite countertops, stainless steel appliances, abundant cabinetry, generous counter space, and a full-size washer and dryer (new in 2026), making it perfect for everyday living and entertaining. The versatile den is ideal as a home office, guest room, nursery, or creative space, providing flexibility to suit your lifestyle. This exceptionally clean, move-in-ready penthouse includes one owned underground parking space and a large, temperature-controlled locker. Owners also have access to a second surface parking space through the building's tag system (first come, first served, subject to property management approval).Residents enjoy excellent amenities, including a fitness centre, party room with a full kitchen, car wash, visitor parking, and beautifully maintained common areas. Ideally located close to shopping, restaurants, schools, parks, walking trails, public transit, the Milton GO Station, and with quick access to Highways 401 and 407, this home offers outstanding convenience for commuters and families alike. Whether you're a first-time buyer, downsizer, or investor, this rare penthouse suite presents an exceptional opportunity to own a beautifully maintained home in one of Milton's most convenient and sought-after communities.

1460 Main Street E Unit 412, Milton
1340 Main Street E Unit 113, Milton
$549,900
2 Beds ⋅ 2 Baths ⋅ W13752974 MLS
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 peaceful first-floor private wing location. Thoughtfully updated throughout, this spacious unit features a bright open-concept layout, freshly painted interiors, and large windows with California shutters that fill the home with natural light. The renovated kitchen showcases brand-new appliances, quartz countertops, and a custom backsplash, seamlessly connecting to the dining and living areas. Both bedrooms are generously sized, with two full bathrooms offering added convenience. Enjoy your own private outdoor space with two separate terraces, perfect for morning coffee or relaxing outdoors. Additional highlights include an ensuite laundry room, dedicated storage locker, and two parking spaces - one garage parking space plus one surface parking permit. The first-floor private wing location offers a quiet setting with added peace and privacy. Ideally situated close to everyday amenities, shopping, dining, parks, schools, major highways, and Milton GO, providing convenient access to commuter routes and the GTA. A move-in-ready opportunity offering space, style, privacy, and an unbeatable combination of convenience and accessibility. Book your private showing today!

1340 Main Street E Unit 113, Milton
1471 Maple Avenue Unit 112, Milton
$589,900
2 Beds ⋅ 2 Baths ⋅ W13727334 MLS
Welcome to this bright and spacious 2-bedroom, 2-full-bathroom main-floor condo in a convenient Milton location. One of the best features of this unit is its main-floor setting - no waiting for elevators, easy in-and-out access, and a more connected, home-like feel with your outdoor space just steps away. Inside, the functional open-concept layout offers a generous living and dining area with a cozy fireplace and plenty of natural light. The kitchen provides ample cabinetry and counter space with a breakfast bar overlooking the living area. Both bedrooms are well-sized, including a spacious primary bedroom with its own ensuite, while the second full bathroom is perfect for family or guests. Ensuite laundry and one parking space add to the everyday convenience. Whether you're a first-time buyer, downsizer or investor, this is a practical, move-in-ready home with everything you need close by. Minutes to Highway 401, Milton GO, schools, parks, shopping and restaurants, with Toronto Premium Outlets just a short drive away. Some photos have been virtually staged to showcase the potential of the space

1471 Maple Avenue Unit 112, Milton
1208 Main Street E Unit 103, Milton
$648,800
2 Beds ⋅ 3 Baths ⋅ W13724296 MLS ⋅ Stax On Main BLDG.
Welcome to STAX on Main! This clean and well maintained 2-bedroom, 2.5-bath stacked townhome offers a spacious, open-concept layout designed for comfortable everyday living. First floor features hardwood floors throughout with plenty of natural light. The modern kitchen features quartz countertops, stainless steel appliances, ample cabinetry, and a large breakfast bar overlooking the combined living and dining area with views of the front yard. The lower level offers two generously sized bedrooms, including a spacious primary suite complete with a 3-piece ensuite and large walk-in closet. A well-appointed 4-piece main bathroom, convenient laundry closet, and additional under-stair storage provide plenty of functionality and extra space. Ideally located within walking distance to public transit, top-rated schools, shopping, and everyday amenities, with Milton GO just minutes away and easy access to major highways-perfect for commuters. INCLUDES 2 UNDERGROUND PARKING WITH LOCKER. A fantastic opportunity to enjoy spacious, low-maintenance living in a convenient desirable Milton neighbourhood.

1208 Main Street E Unit 103, Milton
1479 Maple Avenue Unit 206, Milton
$399,900
2 Beds ⋅ 1 Baths ⋅ W13691544 MLS
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 bright and functional layout with hardwood flooring throughout. The upgraded kitchen features quartz countertops, stylish backsplash and stainless steel appliances. The generously sized den provides excellent flexibility and can be used as a home office, study or additional sleeping space. Spacious primary bedroom with pot lights and a 4-piece bathroom featuring an upgraded quartz vanity.Conveniently located close to the elevator, this unit includes underground parking and 2 unique storage lockers - one in the basement and one on the balcony. Water is included, making this a low-maintenance and practical choice for both homeowners and investors.Enjoy excellent building amenities including a gym/exercise room, party room, car wash and ample visitor parking. Prime Dempsey location just minutes to Highway 401, Milton GO Station, Milton Library, major grocery stores, restaurants, shopping, Cineplex, parks and everyday amenities. Easy access to major routes makes commuting convenient.An excellent opportunity for first-time buyers, investors, downsizers or anyone looking for smart sizing without compromising on space. A well-maintained building, great location, practical layout and low-maintenance lifestyle - this one is a must-see!

1479 Maple Avenue Unit 206, Milton
1208 Main Street E Unit 201, Milton
$699,000
2 Beds ⋅ 3 Baths ⋅ W13673142 MLS
Welcome to Unit 201 at Stax on the Main in the vibrant Dempsey neighbourhood of Milton. This light-filled corner unit is thoughtfully designed across two well-proportioned levels. The home effortlessly adapts to various lifestyles, whether you are commuting, growing into your next chapter, or investing in a high-demand location.Boasting 1,252 SF of finished interior the main living level unfolds with intention; expansive windows draw in natural light and create a warm, inviting atmosphere throughout the open-concept living and dining spaces. At the centre, a sleek, modern kitchen with a generous granite countertop centre island anchors the home, offering both a practical workspace and a natural gathering point for daily life and entertaining. Step out to your private balcony for a quiet moment outdoors or an easy extension of your living space. Upstairs, the home transitions into a more private retreat. The primary bedroom is calm and comfortable, complete with a walk-in closet and its own ensuite. A second well-sized bedroom offers flexibility for guests, a home office, or a growing household, while upper-level laundry simplifies daily routines. Beyond the home, the location delivers on every level. With close proximity to Milton GO Station and quick access to Highway 401, commuting is seamless. Everyday essentials, shopping, and dining are just minutes away at Milton Mall and along the evolving Main Street corridor. Nature lovers and active lifestyles are equally well served. Enjoy scenic trails and green space at Mill Pond, or spend weekends exploring the breathtaking landscapes of Rattlesnake Point Conservation Area, a local favourite for hiking and panoramic escarpment views. A hidden gem buyers will love is the growing food and café scene nearby, including cozy brunch spots and bakeries that give Milton its small-town charm with a modern and sophisticated twist.

1208 Main Street E Unit 201, Milton
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