1029 - DE Dempsey Homes with 16-30 Approx Age

1029 - DE Dempsey Homes with 16-30 Approx Age

Welcome to the charming neighborhood of 1029 - DE Dempsey, nestled in the vibrant city of Milton, Ontario. This community offers a delightful blend of modern living and suburban tranquility, making it an ideal place for families, young professionals, and retirees alike.

One of the standout features of DE Dempsey is its diverse range of homes, many of which boast a rich history with an approximate age of 16 to 30 years. These residences reflect a thoughtful blend of contemporary design and practicality, providing ample space for growing families or those seeking a comfortable retreat. With well-maintained properties and lush green spaces, the neighborhood exudes a welcoming atmosphere that residents take pride in.

The area is not just about beautiful homes; it’s also about lifestyle. DE Dempsey is conveniently located near an array of amenities, including shopping centers, parks, and schools. Families will appreciate the proximity to reputable educational institutions, while nature enthusiasts can enjoy the scenic trails and parks that are perfect for weekend adventures.

Moreover, the neighborhood boasts a strong sense of community, with regular events and gatherings that bring neighbors together. Whether you’re enjoying a leisurely stroll through the tree-lined streets or participating in local festivities, you’ll quickly feel at home in DE Dempsey.

With its appealing homes and vibrant community spirit, 1029 - DE Dempsey is a neighborhood that promises not just a house, but a place to create lasting memories. Come explore all that this delightful area has to offer!

Newest 1029 - DE Dempsey Homes with 16-30 Approx Age

$949,907
3 Beds ⋅ 3 Baths ⋅ W13599510 MLS
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 that's perfect for morning coffee and evening chats. The attached garage and driveway provide excellent parking, with the added potential to widen the driveway. Nestled in Milton's highly sought-after Dempsey neighbourhood, this move-in ready home offers 3 spacious beds, 2.5 baths, and an open-concept layout filled w/natural light. Thoughtfully updated throughout, you'll appreciate the hardwood floors, elegant wood staircase, cozy gas fireplace, and a chef-inspired kitchen featuring quartz countertops, s/s appliances, and a show-stopping waterfall island that's sure to become the heart of every gathering. Upstairs, the oversized primary retreat feels like your own private getaway, complete with two walk-in closets and a beautifully upgraded 4pc ensuite. Step outside to a fully fenced backyard-perfect for summer BBQs & family get-togethers. The unfinished bsmt is a blank canvas ready for your imagination. With convenient garage access to the bsmt, it offers excellent potential for a future in-law suite, additional living space, or the ultimate entertainment hub, home gym, or kids play area. Once finished, the home has the potential to offer approx 2500 sqft. of total living space. Major updates include the roof & furnace, providing added peace of mind for years to come. Location truly sets this home apart. East Milton is one of the towns most convenient/connected communities. The Milton GO is just minutes away, making commuting effortless, while 2 major shopping centres put all your favourite big box stores, grocery stores, restaurants, cafés, and everyday essentials within easy reach. Parks, playgrounds, trails, sports fields, & recreational facilities are woven throughout the area. Even better, you'll have HIGH Walk & Bike Scores. It's the kind of neighbourhood where everyday life simply feels convenient.WATCH VIDEO

1245 Newell Street, Milton
$569,000
2 Beds ⋅ 2 Baths ⋅ W13586246 MLS
Welcome to this beautifully maintained and spacious condo in a sought-after boutique building at 1491 Maple Ave, Unit 401 in Milton. Offering over 1,000 sq ft of well-designed living space, this top-floor unit features soaring 14' cathedral ceilings that create an airy, open feel throughout and are hard to come by! The bright and functional layout includes brand new kitchen cabinetry with a breakfast bar that comfortably seats four-perfect for casual dining or entertaining. The open-concept living is highlighted by a cozy fireplace and enjoy the walkout to a private balcony where BBQs are permitted. Enjoy peaceful, unobstructed east-facing views overlooking picturesque farmland and a serene pond, providing both privacy and a quiet setting. The unit is finished with high-end laminate flooring throughout and upgraded California shutters, and it shows well.This condo offers two generously sized bedrooms and two full bathrooms, making it ideal for a variety of lifestyles. Located in a charming four-storey building with plenty of visitor parking, this property combines the best of convenience and tranquility.Situated just off James Snow Parkway, you'll have quick access to major highways, shopping, and everyday amenities-all while being surrounded by nature.

1491 Maple Avenue Unit 401, Milton
$859,990
3 Beds ⋅ 3 Baths ⋅ W13565412 MLS
Location, Location, Location Beautiful semi detached home ,very well kept, carpet free. Ideally located near top rated schools, scenic parks, shopping destinations, cineplex in a very friendly neighborhood Minutes to Milton go station and Highway 401. The main Fl Kitchen has generous cabinet space and updated fixture with a center island Spacious living room with all hardwood floor has a gas fireplace and has direct access to fully fenced backyard and Gazebo .Ideal for summer entertaining Three Spacious bedroom with hardwood flooring A great family home not to be missed

1248 Newell Street, Milton
$1,174,900
4 Beds ⋅ 3 Baths ⋅ W13564086 MLS
Exceptional family home located on a quiet street, in the sought-after Dempsey Park neighbourhood in Milton a perfect blend of comfort, space, and everyday convenience. Perfect layout for growing families, this move-in ready home is bright and inviting from the moment you step inside, featuring a grand foyer with soaring ceilings filtering in an abundance of natural light. Main floor has 9ft ceilings throughout, and a functional layout ideal for both daily living and entertaining. The kitchen is complete with a separate breakfast area, a large pantry, and a walkout to a private deck-perfect for summer BBQs and outdoor dining. The spacious living room is anchored by a cozy gas fireplace, creating the perfect setting for relaxing family evenings, while the separate dining room overlooks the kitchen, offering an ideal space for hosting gatherings and special occasions. Upstairs, you'll find four generously sized bedrooms, including a comfortable primary retreat featuring a walk-in closet and a 4-piece ensuite bath. The fully finished basement adds valuable living space with a large recreation room and an additional bedroom-perfect for a teenager, guests, or a home office setup. Stylish barn door on the main floor leads you to a main floor laundry with access to the garage. Located within walking distance to top-rated schools, parks, and shopping, and offering easy access to highways and public transit, this home delivers both lifestyle and convenience. A wonderful opportunity to settle into a vibrant, family-friendly community in Milton

187 Cooke Crescent, Milton
$849,000
3 Beds ⋅ 4 Baths ⋅ W13545520 MLS
Welcome to this beautifully renovated 3-bedroom, 4-bathroom townhome nestled in one of Milton's most family-friendly neighbourhoods. Thoughtfully updated throughout, this move-in-ready home features stylish laminate flooring, a modern renovated kitchen designed for both everyday living and entertaining, and spacious principal rooms filled with natural light. Retreat to the generous primary suite complete with a private ensuite bath and large closet, offering the perfect blend of comfort and functionality. The finished basement expands your living space and includes a convenient 2-piece bathroom, ideal for a recreation room, home office, or additional living area. Step outside to enjoy the beautifully landscaped backyard, perfect for summer gatherings, while the charming front porch provides a peaceful spot to relax with your morning coffee or unwind at the end of the day. With parking for up to 3 vehicles, this home offers exceptional convenience. Ideally located close to top-rated schools, shopping, restaurants, parks, transit, and major highways, this exceptional property puts you just moments from all the amenities and attractions that make Milton such a desirable place to call home.

95 Waters Boulevard, Milton
$920,000
3 Beds ⋅ 3 Baths ⋅ W13531894 MLS
Tucked onto a quiet street in one of Milton's most convenient locations, this move-in-ready home offers the kind of space and flexibility that makes everyday life feel easier. Just minutes to Highway 401, Milton GO, schools, parks, shopping, restaurants, and all the essentials, it is a home that truly fits real life. With approximately 1,673 sq.ft. above grade, plus the finished basement, the real value here is in how well the space lives. The main floor is bright, functional, and welcoming, with a spacious entryway, interior garage access, smooth ceilings, pot lights, laminate flooring & an open-concept layout that keeps everything connected. The kitchen has been tastefully updated with quartz countertops, white subway-tile backsplash, matte-black hardware, stainless-steel appliances, and a double undermount sink with a view of the backyard. The breakfast area opens directly to the oversized, fully fenced backyard, creating an easy extension of the living space and giving you the outdoor room so many buyers are after. Whether it is summer dinners outside, space for kids to play, or room for pets to run, this yard is a standout feature. Upstairs is where this home really separates itself from many others in its category. In addition to 3 well-sized bedrooms, there is a spacious second-floor family room that gives you options. It works beautifully as a media room, office, playroom, or an ideal space for those who want a little more room to spread out. The primary bedroom includes a walk-in closet and a private 4-piece ensuite. At the same time, the finished basement adds even more flexibility for a rec room, gym, office, or hobby space, along with storage and a bathroom rough-in. With a covered front porch, a widened interlock driveway, an upper balcony, an interlock patio, and thoughtful updates throughout, this home offers practical value in a location that is hard to beat. Some homes just make more sense in person. Walk through it and see how well this one fits.

53 Dills Crescent, Milton
$999,990
5 Beds ⋅ 4 Baths ⋅ W13502802 MLS
Tucked into Milton's sought-after Dempsey neighbourhood,this detached two-storey residence offers 4+1 bedrooms, 4 bathrooms, and approximately 2,500 square feet of combined living space, creating a home that feels both generous and deeply functional from the moment you step inside. Hardwood floors add warmth and continuity throughout, while the kitchen is beautifully appointed with granite countertops, stainless steel appliances, and an eat-in breakfast area designed for easy mornings and relaxed weekends.What makes this home especially appealing is the way the layout lives. The main floor offers a bright, welcoming living space for everyday comfort, paired with a large separate dining area that instantly elevates the home for those who love to gather, celebrate, and host with ease. It is the kind of space that invites long dinners, holiday moments, and a table full of guests without ever feeling crowded. Upstairs, the home continues to deliver with 4 spacious bedrooms, including a serene primary retreat with a walk-in closet and 4-piece ensuite, along with 2 full bathrooms on the second floor that make busy mornings feel smoother and more effortless.The finished lower level adds a whole new dimension of flexibility. With its own recreation area, bedroom, full bathroom, flexible office space, and laundry. Suitable whether for guests, extended family, a quiet work-from-home setup, or simply extra space to live and grow.And then there is the lifestyle beyond the front door. This home is positioned in one of Milton's most connected family pockets, with Top schools, parks, shopping, recreation, the Milton Leisure Centre, the Milton GO Station, and Highway 401 all within minutes away. It is a location that does more than impress on a map.It gives you back time, softens the pace of busy days, and makes the entire week feel easier.

40 Dills Crescent, Milton
$529,900
2 Beds ⋅ 1 Baths ⋅ W13463528 MLS
Beautifully renovated unit featuring a stunning custom kitchen with premium 36" upper and lower cabinetry, pot drawers, spice rack, soft-close doors and drawers, quartz countertops, quartz backsplash, under-cabinet lighting, and newer stainless steel appliances including fridge, stove, dishwasher and microwave. Freshly painted throughout in premium Benjamin Moore colours. Updated bathroom with quartz vanity, new Moen faucet, undermount sink and new toilet. Quality finishes include wide-plank premium luxury vinyl flooring throughout, new baseboards and trim, updated lighting, blackout blinds and ample closet storage. Equipped with newer washer and dryer. Enjoy central A/C. Ideally located minutes from Hwy 401 and James Snow Parkway, with Walmart Supercentre, shopping, restaurants, parks and everyday amenities just a short 7-minute drive away. Move-in ready and offering exceptional value, modern finishes and low-maintenance living.

1483 Maple Avenue Unit 409, Milton
$1,399,000
4 Beds ⋅ 5 Baths ⋅ W13438172 MLS
Step into luxury with this stunning, fully detached all-brick residence that has been impeccably maintained. With four spacious bedrooms and four and a half bathrooms, this home offers the perfect blend of comfort and elegance. As you enter, you'll be greeted by exquisite hardwood flooring that flows seamlessly throughout the main level. The gourmet kitchen is a chef's delight, featuring modern appliances and ample counter space, perfect for culinary creations and entertaining guests. The finished basement provides additional living space, ideal for family gatherings or a cozy movie night. Step outside to discover your personal oasis: a spectacular yard complete with a beautiful pool, soothing hot tub, and a charming cabana-perfect for summer relaxation and entertaining. This home also boasts a double car garage and numerous upgrades, ensuring you have everything you need right at your fingertips. Located in an attractive neighborhood, your dream next chapter awaits here! Don't miss the opportunity to make this exceptional property yours!

1228 Fox Crescent, Milton
$798,900
3 Beds ⋅ 3 Baths ⋅ W13234686 MLS
Welcome home to this beautiful 3 bed freehold townhome! Amazing location, close to amenities and backing on to Fitzgerald park. Sit out and relax on the spacious covered porch. Enter into the inviting foyer overlooking the generous living room with gorgeous barn board accent wall and newer flooring. This level also boasts a 2 piece powder room. Continue into the large, updated , eat in kitchen with quartz counters and access to the private rear yard , backing onto park space. The second level features three large bedrooms and a four piece main bath. The spacious primary bedroom also has a four piece ensuite and large walk in closet. Recent windows throughout. The unspoiled basement is waiting for your touches. Steps to schools, parks, shopping and many restaurants. Access to the 401 is minutes away. Get out and explore the spectacular Niagara escarpment, go skiing or fishing at Kelso or enjoy one of the many other conservation areas this region has to offer. You will love living at 236 Fitzgerald Cres! Shingles 2021, Windows 2024, Kitchen updated 2024

236 Fitzgerald Crescent, Milton
$579,700
2 Beds ⋅ 2 Baths ⋅ W13130364 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
$589,000
2 Beds ⋅ 2 Baths ⋅ W13127190 MLS ⋅ The Bristol On Main BLDG.
TOTALLY RENOVATED! Welcome to Bristol on Main in Milton's highly sought-after Dempsey neighbourhood. This spacious 2-bedroom, 2-bathroom Cambridge Model offers approximately 1,184 sq ft of beautifully updated living space and is rarely offered in this unique first-floor private wing location, providing exceptional privacy and quiet rarely found in condo living.Freshly painted in a soft neutral palette, the bright open-concept layout features large windows with California shutters, filling the living and dining areas with natural light. The upgraded kitchen showcases stylish two-tone cabinetry, quartz countertops, stainless steel appliances, a custom backsplash, and a functional breakfast bar perfect for everyday living and entertaining. Double patio doors lead to one of two private ground-floor terraces, creating ideal outdoor spaces for relaxing or hosting guests.The split-bedroom layout offers excellent privacy, featuring a spacious primary suite with a full ensuite bath and generous closet space. The second bedroom is perfect for guests, family, or a home office. Additional highlights include wide plank vinyl flooring throughout, in-suite laundry with storage, abundant closet space including a large storage room, two parking spaces, and a dedicated storage locker.Enjoy walking distance to parks, schools, shopping, restaurants, transit, and the Milton GO Station, with quick access to major commuter routes throughout Halton and the GTA. Nearby amenities including Dempsey Park, Sinclair Park, and Milton District Hospital further enhance the convenience of this exceptional location.With its rare layout, dual terraces, generous square footage, and private setting, this home offers a lifestyle that feels more like a bungalow than a traditional condo-an outstanding opportunity in one of Milton's most desirable communities.

1340 Main Street E Unit 113, Milton
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