1029 - DE Dempsey Real Estate

1029 - DE Dempsey Real Estate

Welcome to the charming neighborhood of 1029 - DE Dempsey, nestled in the vibrant city of Milton, Ontario. Known for its picturesque landscapes and family-friendly atmosphere, this community offers a delightful blend of suburban tranquility and urban convenience.

Surrounded by lush parks and green spaces, residents of DE Dempsey enjoy an active lifestyle with numerous walking trails, playgrounds, and recreational facilities nearby. The neighborhood is particularly popular among families, thanks to its excellent schools and a strong sense of community. Local events and gatherings foster a friendly environment where neighbors become friends.

Shopping enthusiasts will appreciate the proximity to a variety of retail options, including local boutiques, grocery stores, and popular shopping centers. The nearby Milton Mall and the charming downtown area provide a diverse selection of dining, shopping, and entertainment choices, ensuring that there’s always something to explore.

Transportation is a breeze in DE Dempsey, with easy access to major highways and public transit options, making commuting to Toronto or surrounding areas convenient for professionals. Additionally, the neighborhood is well-connected to essential amenities, including healthcare facilities, libraries, and community centers.

For those who cherish a blend of nature and modern living, DE Dempsey is a hidden gem in Milton. With its inviting atmosphere, strong community spirit, and abundance of amenities, it’s no wonder that residents take pride in calling this neighborhood home. Come discover the warmth and charm of 1029 - DE Dempsey, where your dream home awaits!

Newest Listings in 1029 - DE Dempsey

$499,000
2 Beds ⋅ 1 Baths ⋅ W13599704 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 Unit 412, Milton
$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
$499,888
2 Beds ⋅ 3 Baths ⋅ W13597846 MLS
Finally You've Found The Perfect Move-In Ready Townhome That Truly Has It All! Here's Your Opportunity To Maximize Value And Experience A Premium Condo Lifestyle Within This Absolutely Stunning End Unit Suite, Located In The Heart Of Charming Milton! This Incredibly Spacious 2 Bedroom Corner Suite Truly Sets The Standard For Those In Search Of A Premium Condo Community, Offering A More Relaxed Change Of Pace, Without The Common Condo Compromises! 1202 Main St E Suite 108 Is Ready To Impress From The Moment You Step Inside - Immediately Your Drawn To The Abundance Of Natural Light This Truly Expansive & Ultra-Stylish Townhome Offers! Be Ready To Host Or Comfortably Unwind Within The Beautiful Main Floor Living Area, Home To A Mesmerizing Modern Kitchen With Huge Centre Island, Complete With Upgraded Lighting, Premium Appliances, Ample Storage + Bonus Balcony Retreat Perfect For Your Morning Coffee! The Lower Level Allows For Incredible Privacy, WhereYour Primary Retreat With Amazing Walk-In Closet & 4Pc Ensuite Steals The Show! Additional Oversized Secondary Bedroom With Great Sized Window, Large Closet & 2nd Full Washroom Is The Perfect Compliment To The Extremely Functional Layout! This Completely Move-In Ready Townhome Has The Dream Combination Of Size, Style & Sunlight That Doesn't Come Around Often.. Don't Miss This One!

1202 Main Street E Unit 108, Milton
$899,900
3 Beds ⋅ 3 Baths ⋅ W13597254 MLS
Presenting 248 Pettigrew Trail - A great semi-detached home in Milton's desirable Dempsey neighbourhood, within walking distance to shopping, restaurants, parks, and everyday conveniences. This 3-bedroom, 2.5 bathrooms home offers a comfortable layout with plenty of space for family living. The main floor features a bright and functional layout with a convenient powder room, while upstairs offers three bedrooms, including a spacious primary bedroom with two closets and a 4-piece ensuite with a soaker tub. The kitchen features stainless steel appliances, and the unspoiled basement provides additional storage, a cold cellar, and the opportunity to create more living space to suit your needs. Enjoy a nicely landscaped yard, plus the convenience of an attached garage with inside access. Recent updates include A/C (2020), Lennox furnace (2022), and roof (approximately 7 years new). With easy access for commuters, this home is a fantastic opportunity in one of Milton's most convenient communities.

248 Pettigrew Trail, Milton
$599,900
3 Beds ⋅ 2 Baths ⋅ W13595384 MLS
Beautiful And Rare 3 Bedroom 2 Bathroom (Approx 1400 Sqft) Penthouse Suite With Vaulted Ceilings. Beautiful Large Kitchen With Brown Cabinets, Brand New Stainless Steel Appliances, Quartz Countertops, Breakfast Bar and Eat-In Breakfast Area. Living And Dining Space With Plenty Of Natural Light. This Lovely Condo Features Laminate Flooring Throughout, Top Floor With 9Ft + Ceilings, Freshly Painted, Private Large Balcony, Ensuite Laundry, Second Bathroom Has Brand New Quartz Countertops And Much More. Huge Primary Bedroom With Room For Office Space, His And Hers Closets, Large Ensuite Bathroom With Brand New Quartz Countertops, Double Sinks and Walk In Shower. 1 Underground Parking And 1 Locker. Convenient Visitor Parking In A Spotless And Well Managed Building. Shows Beautifully, Don't Miss Out On This Meticulously Maintained Condo. Recreation Center For The Complex Includes Exercise Room, Party Room, Rec Room And Meeting Room. Close To All Amenities Schools, Restaurants And Highways.

1350 Main Street E Unit 412, Milton
$499,900
2 Beds ⋅ 1 Baths ⋅ W13593760 MLS
Welcome to this beautifully maintained 2-bedroom, 1-bathroom condo in The Courtyards on Main, a sought-after building built in 2017 and ideally located in the heart of Milton's desirable Dempsey neighbourhood. Enjoy the convenience of being just minutes from downtown, shopping, restaurants, parks, transit, and everyday amenities. This bright west-facing third-floor unit features a private open balcony, perfect for enjoying afternoon sun and evening sunsets. The open-concept layout offers a spacious living and dining area with laminate flooring, fresh paint, upgraded light fixtures, and California shutters (2024), along with direct access to the balcony. The modern kitchen overlooks the main living space and features granite countertops, warm cabinetry, a stylish glass tile backsplash, stainless steel appliances, a breakfast bar, and a separate eat-in area-ideal for both everyday living and entertaining. Both generously sized bedrooms feature laminate flooring, large windows, and double-door closets. The 4-piece bathroom is finished with solid surface countertops. Additional highlights include full-size Amana ensuite laundry, 2 parking spots (one underground parking space plus additional surface parking spot), an exclusive-use storage locker, and access to excellent building amenities including an exercise room and party room. Maintenance fees include heat, water, parking, and common elements, making this an exceptional opportunity for first-time buyers, downsizers, or investors seeking low-maintenance living in a prime Milton location.

1440 Main Street E Unit 303, Milton
$499,900
2 Beds ⋅ 2 Baths ⋅ W13593514 MLS
Welcome to penthouse living in one of Milton's most sought-after locations. This bright and beautifully designed top-floor Ashbury model offers 1,065 sq. ft. of thoughtfully planned living space with 10-foot ceilings, oversized windows, and an open-concept layout that feels both spacious and inviting. The primary bedroom is a true retreat, complete with a spacious closet and a private ensuite featuring double sinks and a walk-in shower. A generous second bedroom and a full four-piece bathroom make this home ideal for guests, a growing family, or a dedicated home office. You'll also appreciate the convenience of one underground parking space with a storage locker located directly behind it (second surface parking available through condo board application, subject to availability), making everyday living that much easier. Whether you're a first-time buyer, down sizer, or simply looking for low-maintenance living without compromising on space or style, this penthouse checks all the boxes. Located close to parks, shopping, restaurants, transit, the highway, and everything Milton has to offer, this is a rare opportunity to enjoy elevated condo living in a prime location. Updates: Laminate Flooring 2026, Thermostat/ Range Hood/ Kitchen & Bathrooms updated 2025, Dishwasher 2024, Clothes Washer & Dryer 2023, Fridge 2022

1470 Main Street E Unit 411, 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
$729,000
3 Beds ⋅ 2 Baths ⋅ W13585540 MLS
Welcome to this beautifully updated 3-bedroom, 2- full bathroom condo offering the perfect blend of space, style, and convenience. This bright and spacious unit features a modern open-concept layout, an upgraded white kitchen with stainless steel appliances, quartz countertops, ample cabinetry, and custom window bench. The renovated bathrooms and convenient ensuite laundry add to the home's appeal. Enjoy relaxing on the large south-facing covered patio, perfect for outdoor enjoyment. With two private entrances, underground parking, and a storage locker, this unit offers exceptional comfort and functionality. Ideally located just minutes from major highways, GO Transit, shopping centres, parks and schools. An excellent opportunity for downsizers, first-time buyers, or families seeking the ease of condo living that checks all the boxes!

1491 Maple Avenue Unit 111, Milton
$469,900
2 Beds ⋅ 1 Baths ⋅ W13548626 MLS
Welcome to 1450 Main St E, Milton, a bright and well-maintained condo offering a functional layout and modern finishes. The versatile den is ideal as a home office, nursery, or guest bedroom. The open-concept living and dining area features laminate flooring and walks out through double glass doors to a private balcony, creating the perfect space to relax or entertain. The kitchen is designed for everyday living with granite countertops, an eat-in breakfast bar, tile flooring, and plenty of workspace. The spacious primary bedroom boasts a large window, generous closet, and elegant coffered ceiling. A stylish bathroom includes a granite vanity with storage, tile flooring, and convenient in-suite laundry tucked behind a separate door. Ideally located close to shopping, restaurants, parks, schools, transit, and major highways-perfect for first-time buyers, downsizers, or investors. Amenities includes: Gym and Party Room

1450 Main Street E Unit 210, Milton
$589,777
2 Beds ⋅ 2 Baths ⋅ W13579722 MLS
Welcome to this beautifully updated Corner Unit , offering approximately 1,020 sq. ft. of bright, functional living space in a highly sought-after, commuter-friendly community. This well-maintained 2-bedroom, 2-bathroom home features an open-concept layout with large windows that fill the space with natural light. Recent updates include new flooring throughout (2020), tile flooring in the kitchen and front entrance, modern kitchen cabinets (2019), newer kitchen appliances (2019), an updated sink and toilet 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 to parks, 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 offers outstanding value, comfort, and location. Don't miss this fantastic opportunity to own a beautifully updated home in a desirable neighbourhood!

1380 Main Street E Unit 210, Milton
$970,000
4 Beds ⋅ 3 Baths ⋅ W13574612 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bathroom corner-lot semi-detached home in the highly sought-after Dempsey neighbourhood of Milton. Thoughtfully cared for and tastefully refreshed, this move-in-ready home offers the perfect blend of style, comfort, and convenience for today's family.Step inside to discover a bright, airy interior featuring **fresh paint throughout-including the walls, ceilings, trim, windows, front door, and garage - **giving the entire home a crisp, modern feel. The home has also been professionally deep cleaned, allowing you to move in and immediately enjoy everything it has to offer.The main floor boasts a spacious open-concept layout with hardwood flooring, abundant natural light, and seamless flow between the living, dining, and family spaces. The contemporary kitchen is complete with quartz countertops, stainless steel appliances, ample cabinetry, a breakfast bar, and overlooks the inviting family room featuring a cozy fireplace-perfect for everyday living and entertaining.Walk out to your private backyard deck, an ideal space for summer barbecues, morning coffee, or relaxing evenings with family and friends.Upstairs offers four spacious bedrooms and beautifully maintained bathrooms. Complete with a 1-car garage, 2-car driveway, and ideally located close to schools, parks, shopping, restaurants, Milton GO Station, and Highway 401. A fantastic opportunity to own a beautifully maintained family home in an unbeatable location!

1015 Borden Lane, Milton
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