1029 - DE Dempsey Homes for Sale

1029 - DE Dempsey Homes for Sale

Welcome to the charming neighborhood of 1029 - DE Dempsey, nestled in the heart of Milton, Ontario. This vibrant community is a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike.

Dempsey is known for its picturesque streets, friendly neighbors, and a strong sense of community. Here, you’ll find an array of well-maintained homes that cater to diverse tastes and lifestyles. From modern townhouses to spacious single-family homes, there is something for everyone. The properties in this area are not only aesthetically pleasing but also offer a variety of amenities, ensuring comfort and convenience for residents.

The neighborhood boasts excellent access to local parks, schools, and shopping centers. Families will appreciate the proximity to top-rated educational institutions, as well as recreational facilities that promote an active lifestyle. Imagine weekend strolls through lush parks or enjoying a picnic with loved ones, all within walking distance from your front door.

For those who enjoy dining and entertainment, Dempsey offers a selection of local restaurants and cafes, perfect for a night out or a casual brunch. With easy access to major highways, commuting to nearby cities like Toronto is a breeze, making it an attractive option for professionals seeking a peaceful retreat after a busy workday.

If you're looking for homes for sale in this delightful neighborhood, you’re in luck! The market is thriving, with a variety of listings available that cater to different budgets and preferences. Don’t miss your chance to become a part of the welcoming Dempsey community—your dream home awaits!

Newest 1029 - DE Dempsey Homes for Sale

214 Ellis Crescent, Milton
$999,999
5 Beds ⋅ 4 Baths ⋅ W14164314 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
1155 Davis Lane, Milton
$889,000
4 Beds ⋅ 4 Baths ⋅ W14140550 MLS
Welcome to this spacious and beautifully maintained semi-detached home in the desirable community of Milton. Offering an ideal blend of comfort, functionality, and versatile living space, this home is perfect for families, first-time buyers, or those looking for additional space to grow. The main level features a bright and inviting layout with generous principal rooms, providing plenty of room for both everyday living and entertaining. The spacious primary bedroom offers a private retreat complete with a 4-piece ensuite, while the additional bedrooms are generously sized and offer excellent flexibility for family, guests, or a home office. The finished basement adds valuable living space and offers endless possibilities for a recreation room, home gym, office, media area, or guest accommodations. With an additional bathroom, the lower level is both practical and versatile. Located in a sought-after Milton neighbourhood close to parks, schools, shopping, restaurants, transit, and major commuter routes, this home offers the perfect combination of space, convenience, and community. A fantastic opportunity to make this spacious Milton home your own!

1155 Davis Lane, Milton
169 COOKE Crescent, Milton
$1,149,999
5 Beds ⋅ 4 Baths ⋅ W14004864 MLS
Attention Families & Investors! Unbeatable value meets high-yield potential at 169 Cooke Cres, priced for a quick sale and ready for immediate closing! This bright, detached gem sits on a highly secure, child-friendly "crescent-within-a-crescent" and boasts ~3,000 sq ft of total finished living space.This premium layout perfectly satisfies both family comfort and investor criteria. The sun-filled main floor features timeless hardwood floors, formal living and dining rooms, and a cozy family room with a gas fireplace. Upstairs, families will love the four generous bedrooms, including a massive primary suite with a walk-in closet and a 4-piece ensuite with a deep soaker tub.For investors or families looking to offset their mortgage from day one, the property features a fully finished basement suite with a separate side entrance, a 5th bedroom, a 3-piece bath, a second kitchen, and a spacious recreation room.The property is complete with a double car garage and a 4-car driveway, offering parking for 6 vehicles. Located in a high-demand Milton pocket, you are walking distance to top-tier schools, parks, shopping, and dining, and just minutes away from Highway 401/407 and the Milton GO Station.Move-in ready, income-ready, and priced to sell fast. Schedule your viewing today before it's gone! The property is Virtually Staged.

169 COOKE Crescent, Milton
1268 Newell Street, Milton
$874,888
4 Beds ⋅ 3 Baths ⋅ W13880968 MLS
Welcome to this beautiful 3-bedroom semi-detached home in the highly sought-after Dempsey neighborhood of Milton! Featuring a bright and functional layout, this home offers comfortable living spaces, generous bedrooms, and excellent potential for families, first-time buyers, or investors. Open Concept Living Room with Hardwood Floors , Pot Lights, Gas Fireplace & W/O to Yard. Nicely Fenced Backyard with Premium Interlocking & Absolutely No Grass !!!! Nice Sized Kitchen with Quartz Countertops, Backsplash & Newer Stainless Steel Appliances !!! Three Nice Sized Bedrooms!!! Upper-Level Jack & Jill Washroom Provides Direct Access From The Second Bedroom !!!!! Finished Basement with A Spacious Rec Room/Workspace Featuring Professionally Installed Home Theatre Wiring, Perfect For A Home Office, Media Room, Gym Or Kids Play Area !!!! Rare 4-Car Driveway Parking With No Sidewalk !!!! Countless Upgrades like 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 & Much more !!!! Enjoy the convenience of a desirable Dempsey location, close to schools, parks, trails, shopping, restaurants, public transit, and major highways. With Milton's growing amenities and family-friendly atmosphere, this is an excellent opportunity to own a home in one of the community's popular neighbourhoods !!!!

1268 Newell Street, Milton
1015 Borden Lane, Milton
$880,000
4 Beds ⋅ 3 Baths ⋅ W13850350 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
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
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
1239 Fox Crescent, Milton
$1,299,999
4 Beds ⋅ 4 Baths ⋅ W13749700 MLS
Corner Lot, Original Owners, One Family Since 2008! Welcome To 1239 Fox Crescent - A 2,840 Sq Ft (MPAC) Detached Home On A Wide 48 x 90 Ft Corner Lot In Dempsey, One Of Milton's Most Established Family Neighbourhoods. The Big-Ticket Items Are Already Done: Roof, Furnace And A/C All Replaced In 2025, As Per The Owners. The Main Floor Offers Separate Living And Dining Rooms With Hardwood, Crown Moulding In The Living Room, A Family Room With Fireplace, And A Kitchen With Island, Stainless Steel Appliances And A Breakfast Area Walking Out To The Yard. Upstairs You Have 4 Generous Bedrooms And 3 Full Bathrooms, Including The Primary Ensuite. The Full Unfinished Basement With An Oversized Cold Room Is A Blank Canvas - Finish It Your Way For A Rec Room, Home Gym Or Extra Bedrooms. Entry From The Garage Through The Laundry Room Leads Directly To The Basement Stairs, With A Door Separating It From The Main Living Area. The Corner Lot Also Provides Potential To Add A Separate Side Entrance (Buyer To Verify With Town Of Milton) - Great Opportunity For A Future In-Law Or Income Suite. Double Garage Plus 2-Car Driveway, Central Vac. Walk To Chris Hadfield PS And St. Peter Catholic Elementary, Minutes To Parks, Shopping, Hwy 401 And Milton GO. Exceptionally Maintained And Ready To Move In. Flexible Closing.

1239 Fox Crescent, Milton
276 Fitzgerald Crescent, Milton
$889,900
3 Beds ⋅ 4 Baths ⋅ W13747818 MLS
Prime location! One of the biggest highlights of this home is the unbeatable convenience it offers - situated just steps from a major shopping plaza with restaurants, grocery stores, cafés, banks, pharmacies, fitness, and everyday amenities within walking distance. Enjoy easy access to popular nearby destinations including Boston Pizza, Longo's, Home Depot, Tim Hortons, Starbucks, LA Fitness, Cineplex and much more. Perfect for families and busy professionals seeking a highly walkable lifestyle in one of Milton's most convenient neighborhoods. Close to schools, parks, transit, and highway 401. Stunning outdoor living! Seamless walk-out deck features an included premium hardtop gazebo with privacy curtains and custom lighting - the ultimate summer lounge!

276 Fitzgerald 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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