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

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
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
$849,000
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
1155 Davis Lane, Milton
$929,000
4 Beds ⋅ 4 Baths ⋅ W13819440 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
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
1239 Fox Crescent, Milton
$1,339,000
4 Beds ⋅ 4 Baths ⋅ W13749700 MLS
Original Owners, One Family Since New! Welcome To 1239 Fox Crescent, A Spacious 2,840 Sq Ft Detached Home In Dempsey, One Of Milton's Most Established And Family-Friendly Neighbourhoods. This Home Has Been Exceptionally Maintained And Offers The Space, Layout And Location Today's Families Are Looking For. Major Updates Have Already Been Taken Care Of, Including The Roof 2025, Furnace & A/C 2025, As Per The Owners. Step Inside To A Bright And Welcoming Main Floor Featuring 9' Ceilings, Hardwood Flooring, Separate Living And Dining Rooms, And An Inviting Family Room With Large Windows And A Gas Fireplace. The Spacious Kitchen Offers Granite Countertops, Stainless Steel Appliances And A Bright Breakfast Area With Walkout To The Fully Fenced Backyard. Main-Floor Laundry And A Powder Room Add Everyday Convenience. Upstairs, You'll Find Four Generously Sized Bedrooms And 3 Full Baths. The Primary Retreat Features His-And-Hers Closets And A 5-Piece Ensuite With A Soaker Tub And Separate Glass Shower. The Second Bedroom Offers Its Own Private Ensuite, Making It An Ideal Space For In-Laws, Older Children Or Guests. Two Additional Bedrooms Share A Full Bathroom. The Unfinished Basement, Complete With Oversized Cold Room, Offers Plenty Of Opportunity To Create Additional Living Space With Potential For A Separate Entrance And Secondary Suite. There Is An Opportunity To Accommodate Extended Family Or Explore Rental Income. Enjoy A Double Garage, Two-Car Driveway Parking, Professional Landscaping Front And Back, Interlock Walkways And A Welcoming Front Porch. The Location Makes Everyday Living Easy. Hwy 401 Is Just Minutes Away, While Grocery Stores, Restaurants, Home Improvement Stores, Fitness Facilities, The Cinema And Milton GO Are All Close By. Top-Rated Schools And Parks Are Also Within Walking Distance. Original-Owner Homes In This Neighbourhood Don't Come Up Often. Book Your Showing Today!

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
248 Pettigrew Trail, Milton
$879,900
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
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