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

276 Sherwood Road, Milton
$1,149,000
5 Beds ⋅ 4 Baths ⋅ W14105314 MLS
Welcome to 276 Sherwood Road! This spacious all-brick 4+1 bedroom, 4-bathroom home offers over 3,200 sq. ft. of beautifully finished living space and is ideally located on a family-friendly street just steps from the park and only 2 minutes to the 401. The inviting main floor features a formal living and dining area, an eat-in kitchen with a breakfast bar, and a warm and welcoming family room complete with gas fireplace. Generous family-sized bedrooms provide plenty of space for everyone, while thoughtful details include dual closets for added storage. The spacious primary suite offers a relaxing retreat with his-and-hers closets and a luxurious 5-piece ensuite. The finished basement extends the living space with a versatile fifth bedroom and 3-piece bathroom-perfect for guests, a teenager, a home office or additional family space. Step outside to a beautifully manicured yard featuring a stone patio and 12 x 10 gazebo, creating a wonderful setting for summer entertaining or relaxing with family and friends. Enjoy the convenience of being within walking distance to everyday amenities, schools, parks and recreational facilities. Furnace and owned water heater 2025, dishwasher 2025, spray foam attic insulation 2024, energy-saving windows 2021, owned security system, Google Home thermostat. Floor plans attached.

276 Sherwood Road, 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
1311 Cartmer Way, Milton
$850,000
3 Beds ⋅ 3 Baths ⋅ W14094118 MLS
Beautifully Updated End-unit Family Home. Welcome to this beautifully-updated family home, offering a warm and inviting layout with quality upgraded finishes throughout. The updated eat-in kitchen boasts beautiful new cabinetry, elegant quartz countertops and ample space for a large family table, making it the perfect spot for everyday meals and casual gatherings. The spacious living room offers a welcoming atmosphere, enhanced by a cozy gas fireplace and hardwood flooring, while providing plenty of room for a separate formal dining area-ideal for entertaining family and friends. A convenient two-piece powder room is located just off the main entrance, adding to the home's thoughtful layout and everyday functionality. Upstairs, the primary bedroom offers a large walk-in closet and a beautiful ensuite bathroom complete with relaxing soaker tub, separate glass-enclosed shower, and upgraded granite countertop. The second and third bedrooms are both generous with ample closet space and large windows. The additional upstairs bathroom has been beautifully finished with a bathtub with glass shower enclosure, modern vanity and attractive flat off-white tiles, creating a clean and contemporary look. The basement boasts a wonderful family room, and ample storage room for all your family needs. Step outside to enjoy the fully-fenced backyard, perfect for families, pets and outdoor entertaining. A spacious deck provides the ideal spot for your BBQ and summer gatherings, while the beautiful tiled walkway creates an attractive entrance into the backyard.

1311 Cartmer Way, 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
1491 Maple Avenue Unit 206, Milton
$349,900
2 Beds ⋅ 1 Baths ⋅ W14004300 MLS
Welcome to Milton's mid-rise condo communities in the Dempsey neighbourhood. This 1-bedroom plus den condo offers an open concept functional living space well-laid-out floor plan. The kitchen is both practical with a breakfast bar. Double glass doors leading to a covered balcony. Maple Crossing offers a friendly community atmosphere with excellent amenities, including a full gym, party room, visitor parking, an elevator, and a car wash bay in the underground garage. Condo fees include water, building insurance, and amenities. The location is hard to beat only 2 minutes to the Highway 401 entrance, close to Milton GO, and surrounded by coffee shops, restaurants, grocery stores, parks and everyday essentials.

1491 Maple Avenue Unit 206, 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
116 Dixon Drive, Milton
$1,389,999
4 Beds ⋅ 3 Baths ⋅ W13826006 MLS
Welcome to 116 Dixon Drive, ideally situated in Milton's sought after Dempsey neighbourhood. This beautiful upgraded home offers a dynamic, open concept layout featuring designer finishes, upgraded lighting, a recently renovated spiral staircase, contemporary interior railings and matching luxury flooring throughout. The impressive finished basement is designed for entertaining, complete with a bar and entertainment room, generous storage and a private workshop. Extensive exterior upgrades include a new roof, insulated garage doors, enhanced attic and above garage insulation, a lawn sprinkler system, exterior lighting, maintenance free vinyl veranda columns and railings, and a maintenance free vinyl fenced backyard. Additional conveniences include an owned hot water tank and electrical rough-in for a future hot tub. Just steps from schools, the library, sports fields, shops and restaurants, with quick access to Highway 401, this is one of Milton's most convenient locations. Move in and enjoy!

116 Dixon Drive, Milton
1487 Maple Avenue Unit 401, Milton
$569,900
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 with soaring 14ft ceilings and 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. Great for downsizers, investors and first-time buyers.

1487 Maple Avenue Unit 401, 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
187 Cooke Crescent, Milton
$1,149,900
4 Beds ⋅ 3 Baths ⋅ W13794070 MLS
Welcome to this beautifully maintained family home, ideally situated on a quiet street in Milton's sought-after Dempsey Park neighbourhood. Offering the perfect blend of comfort, space, and everyday convenience, this move-in-ready home features a bright and functional layout designed with growing families in mind. Step inside to a grand foyer with soaring ceilings and an abundance of natural light. The main floor features 9-foot ceilings and a thoughtfully designed layout ideal for both everyday living and entertaining. The spacious kitchen offers a separate breakfast area, large pantry, and walkout to a private deck-perfect for summer BBQs and outdoor dining. The inviting living room is anchored by a cozy gas fireplace, creating a warm setting for family evenings, while the separate dining room provides an elegant space for hosting gatherings and special occasions. Upstairs, you'll find four generously sized bedrooms, including a spacious primary retreat complete with a walk-in closet and private 4-piece ensuite. A stylish barn door on the main level leads to the convenient laundry room with direct access to the garage. The fully finished basement extends the living space with a large recreation room and an additional bedroom-ideal for a teenager, overnight guests, home office, or playroom. Located within walking distance to top-rated schools, parks, shopping, and everyday amenities, with easy access to public transit, Milton GO, and major highways. A wonderful opportunity to enjoy comfortable family living in one of Milton's established and family-friendly communities.

187 Cooke Crescent, Milton
214 Ellis Crescent, Milton
$1,049,900
5 Beds ⋅ 4 Baths ⋅ W13782732 MLS
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 desirable Milton neighbourhood. Thoughtfully designed with generous living and entertaining spaces, the main level features a bright, open-concept layout, built-in Bose speakers throughout and a sun-filled family room with fireplace, perfect for relaxing or hosting. The upgraded kitchen showcases stainless steel appliances, quartz countertops and a stylish tiled backsplash. Upstairs, discover four generously sized bedrooms and two modern 4-piece bathrooms, including a spacious primary retreat featuring elegant wainscoting, a walk-in closet and a beautifully updated ensuite with a modern stand-up shower. The fully finished basement offers a versatile recreation room with a wet bar and 2-piece bathroom, easily adaptable as an additional bedroom or flexible living space. A contractor sketch is attached showcasing the potential for a separate entrance and/or future conversion to a separate unit, offering excellent income potential, subject to approvals. Extensive recent improvements include a brand-new furnace, fresh paint throughout, upgraded light fixtures and chandeliers, new outdoor pot lights and exterior fixtures, and a phone-controlled illuminated LED house number. The backyard is a private oasis featuring ample space for entertaining, a hot tub and storage shed. An exceptional move-in-ready house offering stylish updates, versatile living space, incredible outdoor living and future rental potential-waiting for you to call it home.

214 Ellis Crescent, Milton
71 Livingston Road, Milton
$949,000
3 Beds ⋅ 3 Baths ⋅ W13697148 MLS
Welcome to this beautifully maintained three bedroom bungaloft ideally situated on a desirable corner lot in the sought-after Dempsey neighbourhood. Proudly offered for the first time by it's original owners, this exceptional home is one of a kind on the street. It's functional layout provides an abundance of natural light with it's main floor 9 ft. ceilings along with a dramatic vaulted ceiling in the family room and a walk-out leading to the backyard deck. The bungaloft design provides the perfect blend of main floor convenience and additional living space in the loft, while three full bathrooms add comfort and practicality for family and guests. Set on a premium landscaped lot, the property offers beautiful curb appeal and a generous sized front porch to enjoy throughout the seasons. Close to schools, parks, amenities and shopping, this is a wonderful opportunity to own a special home that has been cherished by it's owners. Come and see why this one-of-a-kind bungaloft is the one you've been waiting for. Book your private showing today!

71 Livingston Road, Milton
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