1029 - DE Dempsey Homes for Sale

1029 - DE Dempsey Homes for Sale

Welcome to the charming neighborhood of 1029 - DE Dempsey, nestled in the vibrant city of Milton, Ontario. This community perfectly blends suburban tranquility with urban convenience, making it an ideal place for families, professionals, and anyone seeking a welcoming environment.

Dempsey is known for its picturesque streets lined with well-maintained homes and lush green spaces. The area features a variety of housing options, from modern townhouses to spacious single-family homes, catering to diverse lifestyles and budgets. With homes for sale in this desirable neighborhood, potential buyers will find a range of properties that suit their needs, whether they are first-time buyers or looking to upgrade.

Residents of Dempsey enjoy easy access to a wealth of amenities, including shopping centers, parks, and recreational facilities. The nearby Milton Mall and various retail outlets offer everything from grocery stores to boutique shops, making daily errands a breeze. Families will appreciate the proximity to excellent schools, ensuring quality education for their children.

Nature enthusiasts will love the abundance of parks and trails in the area, providing ample opportunities for outdoor activities such as hiking, biking, and picnicking. The scenic views and well-maintained green spaces create a serene backdrop for relaxation and leisure.

Conveniently located near major highways and public transportation, Dempsey offers easy commuting options to Toronto and surrounding areas, making it a prime location for those who work in the city but prefer the comfort of suburban living.

Discover your dream home in the delightful Dempsey neighborhood, where community spirit thrives and every day feels like a breath of fresh air!

Newest 1029 - DE Dempsey Homes for Sale

$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
$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
$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
$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
$1,050,000
3 Beds ⋅ 3 Baths ⋅ W13561464 MLS
A Dream Home for Modern Living Steps from All the Essentials! This exquisite approx 2000sqf Detached home offers an additional fully finished basement area, nestled on a serene, child-friendly street. The exceptional open-concept layout is perfect for both entertaining and everyday living. The expansive dining and living areas feature a stunning bay window, upgraded lighting, and hand-scraped engineered hardwood floors, creating a warm and welcoming atmosphere. The chef-inspired kitchen is a dream, boasting an abundance of counter space, sleek stainless steel appliances (including a gas stove), and a walkout to a custom-covered patio with ambient lighting perfect for dining al fresco. The separate family room, also adorned with hand-scraped engineered hardwood and a cozy gas fireplace, offers a peaceful retreat. Upstairs, the generous bedrooms include a luxurious primary suite complete with a spacious walk-in closet and a spa-like 4-piece ensuite. A well-appointed 3-piece bathroom and a charming second-floor balcony add to the appeal. The fully finished basement features a massive rec room, ideal for entertainment and relaxation. Outside, enjoy the convenience of a BBQ gas hookup, an extended stamped concrete driveway with space for two vehicles, and a single-car garage, providing a total of three parking spaces. Unbeatable Location: Just minutes to highways, public transit, Go Train access, restaurants, cafe, grocery stores, schools and parks this home truly has it all!

1190 Fox Crescent, Milton
$949,900
4 Beds ⋅ 4 Baths ⋅ W13559248 MLS
Welcome to this Highly Upgraded gem. The 267 Fitzgerald Crescent. Stunning Fully Upgraded Home In A Prime Location, perfectly situated within walking distance to cinemas, major anchor stores, transit, restaurants, shopping, and everyday conveniences.Step inside to discover a completely upgraded carpet-free home featuring elegant engineered hardwood flooring throughout, a gorgeous oak staircase, and a modern designer/chef kitchen equipped with high-end BI Appliances and premium finishes. The home showcases beautifully upgraded washrooms and a bright, functional layout designed for comfortable family living.The professionally finished basement offers incredible additional living space complete with an extra bedroom and washroom - perfect for extended family, guests, or a home office setup.Potential for future separate entrance.Upgraded Electrical Panel (200 Amps). Enjoy a well-maintained backyard ideal for relaxing or entertaining. Plus, with no sidewalk, the property offers parking for up to 3 vehicles in total.Features Include:* Fully renovated interior* Carpet-free with engineered hardwood floors* Elegant oak staircase* Modern upgraded kitchen with high-end appliances* Luxuriously upgraded washrooms* Finished basement with bedroom & washroom* Functional family-friendly layout* Well-maintained backyard* No sidewalk - 3 total parking spaces* Walking distance to shopping, cinemas, transit & more.A true turnkey home that combines style, comfort, and unbeatable convenience. Shows exceptionally well!

267 Fitzgerald Crescent, Milton
$1,309,900
4 Beds ⋅ 4 Baths ⋅ W13552242 MLS
High Demand Location In Milton. Walking Distance To The Theatre, Shopping And Daycares. Minutes Away From The Highway And The Go Station. This 4 Bedroom Home Offers 4 Bath, Hardwood Floors On First & Second Floors, 9 Ft Ceiling On Main Floor With Gas Fireplace, Central Vac. Fully Finished Basement With Laminate Floors & Pot Lights. Cold Cellar And Lots Of Storage. House completely renovated with a Separate Basement Apartment with Separate Entrance. Whole House Water Filter Installed!

137 Fitzgerald Crescent, Milton
$1,280,000
6 Beds ⋅ 4 Baths ⋅ W13062088 MLS
RARE OPPORTUNITY Prime Milton LOCATION is Everything: Minutes to Hwy 401, MILTON GO, MILTON LIBRARY, MILTON LEISURE CENTER top-rated schools, Cineplex, shopping... This home offers the rare trifecta of luxury finishes, absolute privacy, and proven income potential. Welcome to this carpet free 3,346 sq. ft. (total living space) all-brick detached residence, perfectly situated on a quiet street fronting a serene wooded lot. Enjoy unparalleled privacy and greenery views right from your front door. The Main Level: Designed for Entertaining The bright, layout is anchored by a gorgeous crown moulding living/ dining flowing to spacious family room with a cozy gas fireplace. The heart of the home is the custom chef's kitchen, boasting premium Quartz countertops, a double oven, and a functional layout. A rare 3-piece bathroom on the main level adds ultimate convenience for guests, that flows into the mudroom complete with a stainless steel sink and abundant storage. The Upper Level: Comfort & Style. Featuring 4 generous bedrooms, including a master retreat with ENSUITE 5 piece bath You'll find another 5-piece washroom upstairs, ensuring no morning rush for the family. The Income Generator: Ready 2-Bed Basement Suite The fully furnished, legal basement apartment is a true mortgage-helper or multi-generational suite. It features a separate side entrance, its own laundry, and a full suite of appliances (dishwasher, stove, fridge, washer/dryer, freezer)-move in ready Outdoor Oasis & Extras: Year-Round Hosting: Step out to a legal backyard deck and a permitted gazebo, complete with a gas BBQ hookup. Significant Savings: High-efficiency gas stove and gas dryer installed to keep monthly utility bills low. Premium Finishes: Identical marble counters throughout the home for a cohesive, high-end feel with premium Quartz countertops on main level custom kitchen. Total Convenience: Attached double-car garage equipped with reliable Cumberland openers. Welcome home!

1017 Woodward Avenue, 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
$895,000
4 Beds ⋅ 3 Baths ⋅ W13531880 MLS
Must See To Believe - Guaranteed To Surpass Your Every Expectation! Nestled In Milton's Highly Sought-After Dempsey Neighbourhood And Located In One Of The Top-Rated School Districts, This Impeccably Maintained And Tastefully Upgraded Semi-Detached Home Offers Exceptional Value, Style And Pride Of Ownership. This Sun-Filled, Bright And Airy Home Features A Modern Open-Concept Layout Perfect For Entertaining And Everyday Living. The Spacious Living Room Showcases Hardwood Floors, Pot Lights, A Cozy Gas Fireplace And Walk-Out To A Beautifully Landscaped, Fully Fenced Backyard With Premium Interlock And No Grass - An Ideal Low-Maintenance Space For Summer BBQs And Family Gatherings. The Modern Kitchen Features Quartz Countertops, Stylish Backsplash, Newer Stainless Steel Fridge & Stove (2023), Upgraded Kitchen Window Overlooking The Living Area And Excellent Prep Space. Generous Sized Bedrooms Offer Comfort And Flexibility, While The Upper-Level Jack & Jill Washroom Provides Direct Access From The Second Bedroom, Making It An Excellent Option As A Second Primary Bedroom. The Finished Basement Adds Valuable Living Space With A Spacious Rec Room/Workspace Featuring Professionally Installed Home Theatre Wiring, Perfect For A Home Office, Media Room, Gym Or Kids Play Area. Carpet-Free Throughout And Truly Move-In Ready, This Home Also Features Rare 4-Car Driveway Parking With No Sidewalk. Recent Upgrades Include Exposed Concrete Driveway Extension & Sidewalk, Renovated Primary Ensuite Shower Area (2025), Renovated Laundry Area (2025), Newer Washer & Dryer (2022), Approx. 2-Year-Old Furnace & Humidifier, Added Interior Garage Access, 1-Year-Old Water Softener & RO Water Filter System, Custom Closet Organizers, Pot Lights Throughout And More. Conveniently Located Minutes To Hwy 401, Walmart, Canadian Superstore, Banks, Kumon, Parks, Schools, Transit And All Amenities.

1268 Newell Street, Milton
$1,099,999
4 Beds ⋅ 3 Baths ⋅ W13520232 MLS
Welcome to this beautifully maintained full brick bungalow, perfectly situated in a quiet, family-friendly neighbourhood on a premium lot backing onto a peaceful pond.The bright, updated main floor features an open-concept layout with a modern kitchen, stylish pot lights, two spacious bedrooms, and two full bathrooms. The double-car garage adds convenience and plenty of storage.Downstairs, you'll find a legal 2-bedroom apartment complete with its own separate entrance, private laundry, full bathroom, and a huge storage room-ideal for rental income, extended family, or multi-generational living.Step outside to your own private oasis featuring a large fenced backyard, an expansive deck perfect for entertaining, and professionally landscaped front and back yards. Enjoy the serenity and privacy of having no rear neighbours, with picturesque views overlooking the pond.Whether you're looking for a family home with income potential or a smart investment opportunity, this property truly has it all. Don't miss your chance to own this exceptional home-book your private showing today!

225 Ellis Crescent, Milton
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