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

$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
$1,149,900
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
$1,149,000
5 Beds ⋅ 4 Baths ⋅ W13761438 MLS
Welcome to this bright and spacious 4+1 bedroom detached gem, perfectly tucked away on a quiet, family-friendly crescent within another crescent - surrounded by amazing neighbors! Offering approximately 3,000 sq ft of total finished living space, this home provides plenty of room to live, work and play. Ideally located within walking distance to schools, parks, shopping, restaurants, and just minutes from major highways for easy commuting. A charming covered front porch welcomes you inside. The main floor features a separate formal living room, dining room and a cozy family room with gas fireplace - all with large bright windows and stylish hardwood flooring. The layout flows seamlessly, creating the perfect environment for everyday living and entertaining. Upstairs, the bright staircase leads to 4 generous bedrooms and 2 full bathrooms. The primary suite offers laminate flooring, walk-in closet and a 4-piece ensuite with separate shower, vanity and deep soaker tub. The additional bedrooms also feature laminate floors and ample closet space, while the main 4-piece bath offers an oversized vanity with tub/shower combo. Need more space? The finished basement / in-law suite with separate side entrance provides excellent versatility - complete with 5th bedroom, 3-piece bathroom, recreation room, second living space and kitchen. Perfect for extended family, home office, study area or potential rental opportunity. With a double car garage and driveway parking for 4 vehicles, this home checks all the boxes for comfort, convenience and value in one of Milton's most desirable locations.

169 COOKE Crescent, Milton
$1,399,000
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
$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
$1,139,000
4 Beds ⋅ 4 Baths ⋅ W13738806 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
$949,000
4 Beds ⋅ 4 Baths ⋅ W13734364 MLS
Welcome to this beautifully updated semi-detached home in a convenient central Milton location, offering 3 bedrooms, 2.5 bathrooms, a bonus upper-level family room, plus a finished 1-bedroom basement apartment with separate entrance and separate laundry $1500 Rent . The home features oak engineered hardwood flooring throughout, fresh paint, updated light fixtures and pot lights in the living and upper family rooms. The refreshed eat-in kitchen showcases quartz countertops, refinished cabinetry with new hardware and updated appliances including fridge, stove and dishwasher. Upstairs, the spacious primary bedroom offers a full ensuite, double closets and laundry. Major updates include upper-level triple-pane windows (2020), roof (2018). Enjoy direct garage access, parking for 4 cars, a backyard patio with storage shed and quick access to Hwy 401. Ideally located within walking distance to GO Transit, recreation centre, arena, library, arts centre, shopping and everyday amenities. A move-in-ready home offering space, upgrades and excellent flexibility for today's family!

1110 DAVIS Lane, Milton
$844,900
3 Beds ⋅ 3 Baths ⋅ W13712870 MLS
Welcome to 241 Featherstone Road, This 3 Bed, 3 Bath Detached Home is Located in Milton's Sought After Dempsey Neighbourhood. This Inviting 2-Storey Residence Offers a Functional and Family-Friendly Layout. The Main Floor Offers a Bright Open Concept Living Space Ideal For Both Everyday Living and Entertaining. A Generous Sized Eat-In Kitchen That Has Ample Cabinetry and Counter Space. Walk-out to a Private Backyard With a Covered Patio, Perfect for Summer BBQ's, Relaxing Evenings, Or Hosting Guests. Upper Level Has 3 Bedrooms, Highlighting the Primary Bedroom with a 5-Pc Ensuite Bath. Convenient Second Floor Laundry Adds Ease to Daily Routines. The Finished Basement Provides Valuable Additional Living Space - Ideal for a Family Room, Office, or Gym. Along with Extra Storage, Including a Cold Room.

241 Featherstone Road, Milton
$979,000
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
$1,449,000
8 Beds ⋅ 6 Baths ⋅ W13642046 MLS
RARE OPPORTUNITY: Detached 5+3 Bedroom Home with Two Separate Basement Suites & Outstanding Income Potential Set on a premium 45.77 ft frontage with a deep lot, this spacious 5-bedroom detached home offers a rare and highly functional layout - ideal for large or multi-generational families,with two separate basement suites, each featuring its own entrance and washroom.The main floor showcases bright, open-concept principal rooms: a formal living and dining area, a generous family room, and a versatile den with a large window, perfect as a homeoffice or study. Hardwood flooring, pot-lights, and a modern kitchen with built-in appliances complete the space, with easy flow throughout.The kitchen is designed for everyday living - extended counter and prep space, ample storage,and a bright eat-in area perfect for family gatherings.Upstairs, five bedrooms await, most with semi-ensuite access, along with a primary retreat featuring a private ensuite and walk-in closet. Every bedroom includes a closet and large windows, and second-floor laundry adds everyday convenience.The newly finished basement is where this home truly stands apart: Basement 1: A fully updated 2-bedroom suite with a separate entrance, new tile flooring,modern kitchen, living area, and updated washroom Basement 2: A second studio-style unit with its own ensuite - ideal for extended family, anin-law setup, or future rental income. Outside, a beautifully landscaped backyard with a stone patio invites outdoor entertaining,while the spacious front porch offers quiet seating with unobstructed trail views. A doublecar garage plus two additional driveway spaces provide ample parking.Located on a quiet, family-friendly street minutes from top-rated schools, parks, shopping,and Highway 401 - this is a rare combination of space, versatility, and long-term investmentvalue that won't stay on the market long.

1009 Woodward Avenue, 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
$949,500
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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