1029 - DE Dempsey Condos for Sale

1029 - DE Dempsey Condos for Sale

Welcome to the vibrant neighborhood of 1029 - DE Dempsey, nestled in the heart of Milton, Ontario. This charming community is a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike. With its beautifully landscaped parks, well-maintained walking trails, and family-friendly amenities, Dempsey offers a welcoming atmosphere that fosters a strong sense of community.

One of the standout features of this neighborhood is its proximity to essential services and recreational opportunities. Residents enjoy easy access to a variety of shopping centers, restaurants, and entertainment options, ensuring that everything you need is just a stone's throw away. The local schools are highly regarded, providing excellent educational opportunities for children of all ages, while nearby parks offer ample space for outdoor activities, picnics, and leisurely strolls.

For those considering a move to this delightful area, there are fantastic condos for sale that cater to diverse lifestyles and preferences. These modern residences boast spacious layouts, contemporary finishes, and a range of amenities, including fitness centers, pools, and communal lounges. Whether you’re a first-time buyer or looking to downsize, the condos in Dempsey offer an unparalleled living experience.

With its perfect blend of comfort, convenience, and community spirit, 1029 - DE Dempsey is not just a place to live; it’s a place to thrive. Come explore the possibilities and discover why so many people are calling this neighborhood home!

Newest 1029 - DE Dempsey Condos for Sale

$499,000
2 Beds ⋅ 1 Baths ⋅ W13599704 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 Unit 412, Milton
$499,888
2 Beds ⋅ 3 Baths ⋅ W13597846 MLS
Finally You've Found The Perfect Move-In Ready Townhome That Truly Has It All! Here's Your Opportunity To Maximize Value And Experience A Premium Condo Lifestyle Within This Absolutely Stunning End Unit Suite, Located In The Heart Of Charming Milton! This Incredibly Spacious 2 Bedroom Corner Suite Truly Sets The Standard For Those In Search Of A Premium Condo Community, Offering A More Relaxed Change Of Pace, Without The Common Condo Compromises! 1202 Main St E Suite 108 Is Ready To Impress From The Moment You Step Inside - Immediately Your Drawn To The Abundance Of Natural Light This Truly Expansive & Ultra-Stylish Townhome Offers! Be Ready To Host Or Comfortably Unwind Within The Beautiful Main Floor Living Area, Home To A Mesmerizing Modern Kitchen With Huge Centre Island, Complete With Upgraded Lighting, Premium Appliances, Ample Storage + Bonus Balcony Retreat Perfect For Your Morning Coffee! The Lower Level Allows For Incredible Privacy, WhereYour Primary Retreat With Amazing Walk-In Closet & 4Pc Ensuite Steals The Show! Additional Oversized Secondary Bedroom With Great Sized Window, Large Closet & 2nd Full Washroom Is The Perfect Compliment To The Extremely Functional Layout! This Completely Move-In Ready Townhome Has The Dream Combination Of Size, Style & Sunlight That Doesn't Come Around Often.. Don't Miss This One!

1202 Main Street E Unit 108, Milton
$599,900
3 Beds ⋅ 2 Baths ⋅ W13595384 MLS
Beautiful And Rare 3 Bedroom 2 Bathroom (Approx 1400 Sqft) Penthouse Suite With Vaulted Ceilings. Beautiful Large Kitchen With Brown Cabinets, Brand New Stainless Steel Appliances, Quartz Countertops, Breakfast Bar and Eat-In Breakfast Area. Living And Dining Space With Plenty Of Natural Light. This Lovely Condo Features Laminate Flooring Throughout, Top Floor With 9Ft + Ceilings, Freshly Painted, Private Large Balcony, Ensuite Laundry, Second Bathroom Has Brand New Quartz Countertops And Much More. Huge Primary Bedroom With Room For Office Space, His And Hers Closets, Large Ensuite Bathroom With Brand New Quartz Countertops, Double Sinks and Walk In Shower. 1 Underground Parking And 1 Locker. Convenient Visitor Parking In A Spotless And Well Managed Building. Shows Beautifully, Don't Miss Out On This Meticulously Maintained Condo. Recreation Center For The Complex Includes Exercise Room, Party Room, Rec Room And Meeting Room. Close To All Amenities Schools, Restaurants And Highways.

1350 Main Street E Unit 412, Milton
$499,900
2 Beds ⋅ 1 Baths ⋅ W13593760 MLS
Welcome to this beautifully maintained 2-bedroom, 1-bathroom condo in The Courtyards on Main, a sought-after building built in 2017 and ideally located in the heart of Milton's desirable Dempsey neighbourhood. Enjoy the convenience of being just minutes from downtown, shopping, restaurants, parks, transit, and everyday amenities. This bright west-facing third-floor unit features a private open balcony, perfect for enjoying afternoon sun and evening sunsets. The open-concept layout offers a spacious living and dining area with laminate flooring, fresh paint, upgraded light fixtures, and California shutters (2024), along with direct access to the balcony. The modern kitchen overlooks the main living space and features granite countertops, warm cabinetry, a stylish glass tile backsplash, stainless steel appliances, a breakfast bar, and a separate eat-in area-ideal for both everyday living and entertaining. Both generously sized bedrooms feature laminate flooring, large windows, and double-door closets. The 4-piece bathroom is finished with solid surface countertops. Additional highlights include full-size Amana ensuite laundry, 2 parking spots (one underground parking space plus additional surface parking spot), an exclusive-use storage locker, and access to excellent building amenities including an exercise room and party room. Maintenance fees include heat, water, parking, and common elements, making this an exceptional opportunity for first-time buyers, downsizers, or investors seeking low-maintenance living in a prime Milton location.

1440 Main Street E Unit 303, Milton
$499,900
2 Beds ⋅ 2 Baths ⋅ W13593514 MLS
Welcome to penthouse living in one of Milton's most sought-after locations. This bright and beautifully designed top-floor Ashbury model offers 1,065 sq. ft. of thoughtfully planned living space with 10-foot ceilings, oversized windows, and an open-concept layout that feels both spacious and inviting. The primary bedroom is a true retreat, complete with a spacious closet and a private ensuite featuring double sinks and a walk-in shower. A generous second bedroom and a full four-piece bathroom make this home ideal for guests, a growing family, or a dedicated home office. You'll also appreciate the convenience of one underground parking space with a storage locker located directly behind it (second surface parking available through condo board application, subject to availability), making everyday living that much easier. Whether you're a first-time buyer, down sizer, or simply looking for low-maintenance living without compromising on space or style, this penthouse checks all the boxes. Located close to parks, shopping, restaurants, transit, the highway, and everything Milton has to offer, this is a rare opportunity to enjoy elevated condo living in a prime location. Updates: Laminate Flooring 2026, Thermostat/ Range Hood/ Kitchen & Bathrooms updated 2025, Dishwasher 2024, Clothes Washer & Dryer 2023, Fridge 2022

1470 Main Street E Unit 411, Milton
$569,000
2 Beds ⋅ 2 Baths ⋅ W13586246 MLS
Welcome to this beautifully maintained and spacious condo in a sought-after boutique building at 1491 Maple Ave, Unit 401 in Milton. Offering over 1,000 sq ft of well-designed living space, this top-floor unit features soaring 14' cathedral ceilings that create an airy, open feel throughout and are hard to come by! The bright and functional layout includes brand new kitchen cabinetry with a breakfast bar that comfortably seats four-perfect for casual dining or entertaining. The open-concept living is highlighted by a cozy fireplace and enjoy the walkout to a private balcony where BBQs are permitted. Enjoy peaceful, unobstructed east-facing views overlooking picturesque farmland and a serene pond, providing both privacy and a quiet setting. The unit is finished with high-end laminate flooring throughout and upgraded California shutters, and it shows well.This condo offers two generously sized bedrooms and two full bathrooms, making it ideal for a variety of lifestyles. Located in a charming four-storey building with plenty of visitor parking, this property combines the best of convenience and tranquility.Situated just off James Snow Parkway, you'll have quick access to major highways, shopping, and everyday amenities-all while being surrounded by nature.

1491 Maple Avenue Unit 401, Milton
$729,000
3 Beds ⋅ 2 Baths ⋅ W13585540 MLS
Welcome to this beautifully updated 3-bedroom, 2- full bathroom condo offering the perfect blend of space, style, and convenience. This bright and spacious unit features a modern open-concept layout, an upgraded white kitchen with stainless steel appliances, quartz countertops, ample cabinetry, and custom window bench. The renovated bathrooms and convenient ensuite laundry add to the home's appeal. Enjoy relaxing on the large south-facing covered patio, perfect for outdoor enjoyment. With two private entrances, underground parking, and a storage locker, this unit offers exceptional comfort and functionality. Ideally located just minutes from major highways, GO Transit, shopping centres, parks and schools. An excellent opportunity for downsizers, first-time buyers, or families seeking the ease of condo living that checks all the boxes!

1491 Maple Avenue Unit 111, Milton
$469,900
2 Beds ⋅ 1 Baths ⋅ W13548626 MLS
Welcome to 1450 Main St E, Milton, a bright and well-maintained condo offering a functional layout and modern finishes. The versatile den is ideal as a home office, nursery, or guest bedroom. The open-concept living and dining area features laminate flooring and walks out through double glass doors to a private balcony, creating the perfect space to relax or entertain. The kitchen is designed for everyday living with granite countertops, an eat-in breakfast bar, tile flooring, and plenty of workspace. The spacious primary bedroom boasts a large window, generous closet, and elegant coffered ceiling. A stylish bathroom includes a granite vanity with storage, tile flooring, and convenient in-suite laundry tucked behind a separate door. Ideally located close to shopping, restaurants, parks, schools, transit, and major highways-perfect for first-time buyers, downsizers, or investors. Amenities includes: Gym and Party Room

1450 Main Street E Unit 210, Milton
$589,777
2 Beds ⋅ 2 Baths ⋅ W13579722 MLS
Welcome to this beautifully updated Corner Unit , offering approximately 1,020 sq. ft. of bright, functional living space in a highly sought-after, commuter-friendly community. This well-maintained 2-bedroom, 2-bathroom home features an open-concept layout with large windows that fill the space with natural light. Recent updates include new flooring throughout (2020), tile flooring in the kitchen and front entrance, modern kitchen cabinets (2019), newer kitchen appliances (2019), an updated sink and toilet in the second bathroom, and new laundry machines (2025) with warranty. Ideally located just a short walk to the GO Station and less than 3 minutes to Highway 401,this home offers exceptional convenience for commuters. Enjoy being within walking distance to parks, schools, shopping, restaurants, Go Station and other everyday amenities .Whether you're a first-time home buyer, downsizer, or investor, this move-in-ready home offers outstanding value, comfort, and location. Don't miss this fantastic opportunity to own a beautifully updated home in a desirable neighbourhood!

1380 Main Street E Unit 210, Milton
$579,900
3 Beds ⋅ 2 Baths ⋅ W13569618 MLS
Welcome to luxury condo living in one of Milton's most sought-after communities! This beautifully appointed 2-bedroom plus full den with a closet offers the perfect blend of style, comfort, and functionality. Designed with modern living in mind, the open-concept layout showcases 9-foot smooth ceilings, laminate flooring throughout, and an abundance of natural light.The upgraded kitchen is a chef's delight, featuring granite countertops, a stylish backsplash, under-cabinet lighting, and generous counter space, making it ideal for everyday living and effortless entertaining. The spacious primary retreat boasts a walk-in closet and a spa-inspired 3-piece ensuite complete with an oversized glass shower. The second bedroom offers direct access to the private balcony, while the versatile den with a closet can easily serve as a third bedroom, nursery, or home office. Additional conveniences include in-suite laundry, one underground parking space, and a locker conveniently located on the same floor. Enjoy an exceptional lifestyle with world-class building amenities including 24-hour concierge service, security cameras, a party room with a gourmet kitchen, fitness centre, steam room, yoga studio, pet spa, guest suite, library, outdoor pool, hot tub, and a spectacular rooftop terrace complete with gas barbecues and panoramic views.Offering the ultimate "live, work, and play" lifestyle, this exceptional condominium combines luxury, convenience, and resort-style amenities in an unbeatable Milton location. A rare opportunity you won't want to miss!

1050 Main Street E Unit 226, Milton
$479,900
2 Beds ⋅ 1 Baths ⋅ W13558296 MLS
Welcome to Bristol on Main Condominiums! Ground floor unit facing park with a park view. Walk out patio from kitchen. BBQ allowed. Breakfast style countertop. This is a well-established mid-rise condo community located in the Dempsey neighbourhood of Milton. Built by Sutherland Development and completed around 2012, amenities include: A Gym, The buildings share a central rec centre where residents enjoy access to a party/social room with kitchen and fireplace, fitness/exercise room and visitor parking. Den can be used as a second bedroom and is currently being used as one. An extra surface parking spot is available at no extra cost from management.Plenty of visitor parking. Minutes to HWY 401, transit at your door step. * NOTE * Unit is wheelchair accessible, wide doors on main level units.

1390 Main Street E Unit 107, Milton
$515,000
2 Beds ⋅ 1 Baths ⋅ W13555576 MLS
Open concept Hampton model, 893 sq ft, in the Heart of Milton's Dempsey neighborhood. Just steps away from shopping, entertainment, and great schools with quick and easy access to both 401 and public transit (Milton GO). Lots of upgrades. This well -maintained home features 1 bedroom + den which has a walk-in closet...large eat-in kitchen w/French doors that lead to balcony which overlooks park. Stainless steel appliances, glass backsplash, brand new elegant quartz counters. Fresh modern paint colours. Spacious primary bedroom features sitting area, double closets & trey ceilings. The 4-pc bathroom features quartz counters, in-suite laundry and provide additional comfort & convenience. Access to excellent amenities, including a clubhouse, fitness center and a car wash bay in the underground parking garage. Ample visitor parking is also available. 1 underground parking spot and 1 locker included.

1370 Main Street E Unit 205, Milton
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