1029 - DE Dempsey Real Estate

1029 - DE Dempsey Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in 1029_-_DE_Dempsey and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

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Newest Listings in 1029 - DE Dempsey

$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

$419,000
2 Beds 1 Baths W13783270 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 E Unit 412, 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

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