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304 Winston Road in Oakville: 1020 - WO West House for sale : MLS®# W13159190
304 Winston Road Oakville L6L 4W5 OPEN HOUSE: Jun 07, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, June 7, 2026 2:00PM - 4:00PM
$4,480,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13159190
- Bedrooms:
- 5
- Bathrooms:
- 6
Welcome to 304 Winston Rd, an exceptional custom-designed and built residence offering 5897 sq ft of total living space in one of Oakville's most prestigious neighbourhoods. Perfectly positioned on a premium lot just a few minutes walk to Appleby College, this spectacular home blends timeless transitional architecture with sophisticated finishes, modern smart-home technology, and luxurious resort-inspired living.The exceptional backyard is an outdoor retreat featuring custom infinity edge saltwater pool and hot tub surrounded by expansive entertaining areas. Enjoy indoor-outdoor living beneath the covered rear porch complete with built-in automated screens, fireplace and TV allowing for enjoyment well into the shoulder seasons. Integrated security cameras, advanced Control4 automation, and a dedicated Generator provide added convenience, comfort, and peace of mind. Inside, the home exudes warmth and sophistication. The thoughtfully designed layout offers exceptional versatility, highlighted by a rare main floor primary complete with a luxurious ensuite bath and walk-in closet. An integrated elevator provides ease with access to all levels of the home. With 4+1 bedrooms and 5.5 baths, the residence is perfectly suited for families of all sizes. Two separate laundry rooms further enhance the home's everyday practicality and convenience. The fully finished lower level has been meticulously designed for year-round enjoyment featuring radiant heated floors throughout for exceptional comfort. This impressive space includes a home theatre, gym, rec area, guest/nanny suite & ample storage. Combining luxurious amenities, timeless design, and an unbeatable South Oakville location close to top-ranked schools, parks, waterfront trails, and everyday conveniences, 304 Winston Rd. presents an extraordinary opportunity to experience refined custom living in one of the town's most sought-after communities. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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1364 Acton Crescent in Oakville: 1011 - MO Morrison House for sale : MLS®# W13141860
1364 Acton Crescent Oakville L6J 2S5 OPEN HOUSE: Jun 07, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, June 7, 2026 2:00PM - 4:00PM
$3,699,900Residential Freehold- Status:
- Active
- MLS® Num:
- W13141860
- Bedrooms:
- 5
- Bathrooms:
- 7
Situated within prestigious Morrison in South East Oakville, this exceptional modern custom residence is located in one of the area's most desirable communities, known for its mature tree-lined streets, highly regarded schools and close proximity to some of the region's finest private schools. Backing onto Wedgewood Creek ravine with prized southwest exposure, the property enjoys remarkable privacy, beautiful natural surroundings and abundant natural light throughout the day. Offering over 4,600 sq. ft. of finished living space, the home blends contemporary architecture with thoughtful everyday functionality. An impressive open-to-above foyer and staircase create a dramatic sense of arrival, while expansive windows, elegant glass railings and custom millwork establish a refined modern atmosphere throughout. Designed for family living and entertaining, the main level features bright open spaces centred around a chef-inspired kitchen with an oversized island, marble feature wall, appliance garage and premium integrated Sub-Zero, Wolf and Miele appliances. Floor-to-ceiling windows connect the interior with the surrounding landscape, while a sleek built-in gas fireplace anchors the living area. Radiant heated flooring extends throughout all three levels. The home offers five spacious bedrooms, each with its own ensuite bathroom, including a luxurious primary retreat with a spa-inspired six-piece ensuite and custom walk-in closet. The fully walk-out lower level extends the living space with expansive recreation and entertaining areas, custom wet bar and direct backyard access. Outdoor spaces include an upper terrace, covered patio areas and a private backyard setting surrounded by mature trees and ravine views. A rare opportunity to enjoy modern architecture, exceptional functionality and a remarkable natural setting in one of Oakville's most sought-after neighbourhoods. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
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1319 Greeneagle Drive in Oakville: 1007 - GA Glen Abbey House for sale : MLS®# W13223086
1319 Greeneagle Drive Oakville L6M 2N1 OPEN HOUSE: Jun 06, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, June 6, 2026 2:00PM - 4:00PM
$2,750,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13223086
- Bedrooms:
- 6
- Bathrooms:
- 4
Location! Location! Welcome to 1319 Greeneagle Drive nestled in the sought after Gated community of Fairway Hills. Quiet cul-de-sac plus granted access to 11 acres of meticulously maintained grounds. Backing onto the 5th fairway offering breathtaking views as soon as you walk in. This spectacular family home has been extensively renovated with well over 300K spent by the current owners. Painted throughout in crisp designer white, smooth ceilings, over 170 pot lights, updated 200amp panel, new shingles, skylight + insulation, stone driveway and walkway, commercial grade extensive home automation system with security/smart locks, EV ready and smart closet designs. The lower level has been professionally finished with a rec room, 5th bedroom, full washroom, gym and a fantastic pantry/storage room. The primary suite has been transformed to create his and hers closets and a spa- like ensuite with heated floors, glass curb less shower and soaker tub. Entertainers backyard with large deck and heated in ground pool. Close to top rated schools, hiking in the 16 mile trail system, shopping and highway access.Move in and enjoy! More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
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44 Head Street in Oakville: 1002 - CO Central House for sale : MLS®# W13044812
44 Head Street Oakville L6K 1L5 OPEN HOUSE: Jun 07, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, June 7, 2026 2:00PM - 4:00PM
$2,299,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13044812
- Bedrooms:
- 4
- Bathrooms:
- 5
Welcome to 44 Head St - an exceptional home in the heart of Oakville- steps from Kerr Village & downtown. Enjoy walkable access to local shops, dining & the lakefront-the perfect blend of convenience & tranquility. Offering almost 2200 sq ft plus fully finished basement ( 1015 sq ft),this remarkable residence offers timeless charm & modern functionality. Set behind pretty gardens, the Dark Slate wood siding & crisp white trim frame an inviting front porch-perfect for morning coffee or evening wine. Inside, 9' ceilings, hardwood floors, crown moulding & high baseboards create a refined, elevated feel. The entertainer's kitchen showcases granite countertops, a large island, professional-grade appliances & generous storage, seamlessly flowing into the bright, open-concept living & dining areas. A cozy gas fireplace with custom millwork adds warmth, while French doors lead to the beautifully landscaped rear garden-perfect for relaxing or hosting outdoors. A versatile room on the main floor can serve as your personal office or den; it could also be transformed into a separate dining room if desired. Upstairs are 3 spacious bedrooms, each with ensuites with heated floors & walk-in closets . The lower level (9' ceilings) includes a spacious family room plus 4thbedroom, 3pc bath & large laundry room. Storage is no issue in this home with the many custom built-in closets & cabinets. A detached garage with EV charger features a rare basement for even more storage! Plus there is parking for 6 cars on the extra long driveway. A fully fenced private rear yard, & unbeatable walkability to parks, shops, cafes & the waterfront make this turnkey property a rare offering. Meticulously maintained by the current owners, recent updates include powder room renovation (2024), driveway resurfaced (2024), exterior newly stained(2024) & insulation upgraded to R60 (2025). Ideal for empty nesters, downsizers & families. Don't miss this opportunity to experience Oakville's historic charm. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
- 1 (416) 7350120
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63 Tradewind Drive in Oakville: 1001 - BR Bronte House for sale : MLS®# W12865776
63 Tradewind Drive Oakville L6L 6K8 OPEN HOUSE: Jun 07, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, June 7, 2026 2:00PM - 4:00PM
$2,199,000Residential Freehold- Status:
- Active
- MLS® Num:
- W12865776
- Bedrooms:
- 4
- Bathrooms:
- 3
Luxury lakeside living in Bronte's coveted Schooner's Reach. Completely reimagined, this freehold townhome offers beautifully renovated, low-maintenance living just steps to the lake, marina and vibrant shops and restaurants of Bronte Village. When your home feels larger than you need and upkeep begins to take more than it gives back, the idea of change becomes compelling. Here, you have the space you want with none of the demands you don't. The main level features wide-plank flooring, expansive sightlines and a refined redesign throughout. The kitchen includes custom cabinetry, quartz surfaces, integrated wall ovens, gas cooktop and two-tone finishes. Additional windows enhance natural light in the family room, while patio doors lead to a large private terrace, ideal for outdoor dining or relaxed evenings under the stars. A rebuilt staircase across all three levels with hardwood treads and modern railings serves as a striking architectural feature. Pot lighting, contemporary fixtures and under-cabinet lighting add warmth and function. The second level offers three flexible rooms suited to bedrooms, office or living space. One larger room works well as a lounge or workspace, while still allowing for two additional bedrooms. A renovated full bath and laundry complete the level. The third floor is dedicated to a private primary retreat with a spacious bedroom, custom dressing area, three walk-in closets, a five-piece ensuite and its own balcony. A flexible lower level provides space for a home office, gym or media room, along with storage and interior access to the double garage. Membership in the Schooner's Reach Owners Association, currently $150 per month, includes lawn care, landscaping, spring and fall cleanups, snow removal and seasonal window cleaning, along with a private tennis court and shared greenspace. A lock-and-go lifestyle in a friendly, freehold lakeside community. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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1277 Old Bridle Path in Oakville: 1007 - GA Glen Abbey House for sale : MLS®# W13127566
1277 Old Bridle Path Oakville L6M 1A3 OPEN HOUSE: Jun 06, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, June 6, 2026 2:00PM - 4:00PM
$1,898,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13127566
- Bedrooms:
- 5
- Bathrooms:
- 4
This completely move in ready family home is on one of the prettiest and most desirable streets in Glen Abbey. Pride of ownership is evident in this private enclave of Arthur Blakely homes. Situated in the middle of the crescent this house backs onto treed ravine and is very private in the backyard. The four plus one bedroom family home is perfect for a growing family. Renovated kitchen with greenhouse windows overlooks the backyard/ravine/hot-tub. Family room with wood burning fireplace also overlooks the backyard. Kitchen was fully renovated with custom cabinetry, large island, granite counter tops, stainless steel appliances and built-in window seat. Main floor laundry/mudroom has custom built in cupboards, access to garage and side yard and front loading washer and dryer. Maple hardwood throughout the main and second floors. Primary bedroom has extra large walk-in closet with window and large fully renovated bathroom with soaker tub and large shower. There are 3 other spacious bedrooms and main bathroom that was fully renovated in 2023 on the second floor. Fully finished basement has large recreation area, gym area, fifth bedroom, 3 piece bathroom and loads of storage. Quiet court has quick access to Abbey Lane Park and school as well as playground and toboggan hill in winter. Amazing location close to trails, highly rated schools, parks, shopping, transit, quick access to major highways, Oakville hospital, Glen Abbey Golf course and the famous Monastery Bakery. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
- 1 (416) 7350120
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1053 Old Oak Drive in Oakville: 1022 - WT West Oak Trails House for sale : MLS®# W13238450
1053 Old Oak Drive Oakville L6M 3K5 OPEN HOUSE: Jun 06, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, June 6, 2026 2:00PM - 4:00PM
$1,838,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13238450
- Bedrooms:
- 5
- Bathrooms:
- 4
This move in ready family home is on a quiet court and its premium lot backs onto Sixteen Hollow park and playground. The home has been completely renovated and maintained by it's current owners. Backyard with salt water pool, outdoor kitchen, gazebo, and patio areas. Fully renovated kitchen over looks backyard and has custom cabinetry, high end appliances and large sit up breakfast bar. Work from home from the spacious main floor office. Hardwood and stone floors throughout. Large second story family room. Spacious primary bedroom has large ensuite with soaker tub and separate glassed in shower. Three other good sized bedrooms as well. Fully finished basement has fifth bedroom, 3 piece bathroom and large recreation room including games area, and wet bar/kitchen. Baseball diamond in Sixteen Hollow park has no lighting - so no after dark baseball games. Very close walking distance to top schools including St. Teresa, West Oak Public school and Loyola secondary school. Also, walking distance to entrance of the 16- mile creek trail system (8.5 km of trails). The new Oakville Hospital is a 9 minute drive. Quick commute to Oakville Go Station, loads of shopping and restaurants and all major highways. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
- 1 (416) 7350120
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2070 Willhaven Trail in Oakville: 1019 - WM Westmount House for sale : MLS®# W13177362
2070 Willhaven Trail Oakville L6M 5G3 OPEN HOUSE: Jun 07, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, June 7, 2026 2:00PM - 4:00PM
$1,828,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13177362
- Bedrooms:
- 5
- Bathrooms:
- 4
Welcome to 2070 Willhaven Trail - a beautifully appointed 5-bedroom, 3.5-bathroom family home in one of Oakville's most desirable communities. A welcoming foyer with an elegant wood staircase sets the tone upon entry. The formal living and dining rooms are enhanced by decorative pillars, creating a sophisticated space for entertaining. The main level features 9-foot ceilings and rich dark hardwood flooring, offering warmth and timeless appeal throughout. The chef's kitchen is thoughtfully designed with stainless steel appliances, granite countertops, abundant cabinetry, and a bright breakfast nook with walkout to the rear yard. Open to the spacious family room with a cozy gas fireplace, this layout is ideal for both everyday living and hosting gatherings. Upstairs, you'll find 8-foot ceilings and five generously sized bedrooms. The primary retreat offers a luxurious 5-piece ensuite with double sinks and a walk-in closet. Additional bedrooms are well proportioned and serviced by two additional bathrooms, providing comfort and functionality for a growing family. Convenient main level laundry adds everyday ease. The unfinished basement presents excellent potential to customize to your needs. Additional highlights include an asphalt driveway with concrete border, new garage door, and roll shutters on all doors and windows - offering low maintenance, energy efficiency, noise reduction, weather protection, and enhanced security. Ideally located close to highways, shopping, library, recreation centre, and golf course -this is an exceptional opportunity to own a spacious family home in prime Oakville. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
- 1 (416) 7350120
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2055 Blacksmith Lane in Oakville: 1007 - GA Glen Abbey House for sale : MLS®# W13159172
2055 Blacksmith Lane Oakville L6M 3A3 OPEN HOUSE: Jun 06, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, June 6, 2026 2:00PM - 4:00PMOPEN HOUSE: Jun 07, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, June 7, 2026 2:00PM - 4:00PM
$1,799,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13159172
- Bedrooms:
- 7
- Bathrooms:
- 5
A home built to last, nestled on a quiet, family-friendly street in prestigious Glen Abbey community.This impressive two-storey residence offers a timeless, functional layout with 5+2 bedrooms, 5 bathrooms, and over 5,000 sq ft of living space.Step inside and be welcomed by a spectacular Scarlet O'Hara staircase, complemented by double skylights that flood the home with natural light throughout the day. The bright living room features a picturesque window overlooking the front garden, while the formal dining room provides an elegant setting for entertaining.The kitchen showcases custom cabinetry, a central island, granite countertops, eating area, smooth ceilings, and pot lights, creating a perfect space for everyday living. The spacious family room, complete with a cozy wood fireplace, offers the ideal gathering place for family and friends. A main floor office adds flexibility for working from home space.Ascending the elegant wood staircase, the second floor features a spacious primary retreat with a reading nook, walk-in closet and 5-piece ensuite bathroom. Above the garage, an in-law suite with own private staircase offers exceptional private living space. Three additional generously sized bedrooms, each with large windows and ample closet space, share a well-appointed 4-piece bathroom.The finished lower level provides additional living space, featuring a large recreation room with enlarged windows, an extra two bedroom, a kitchen, and a full bathroom - ideal for extended family, guests, teenagers.Step outside to enjoy the private backyard retreat, complete with a wooden deck and patio stone area, perfect for outdoor entertaining and relaxing.Conveniently located near provincial parks, scenic trails, the new hospital, major highways including the QEW and 403, and award-winning golf courses, this exceptional home offers the perfect blend of space, comfort, and an unbeatable Glen Abbey lifestyle. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
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2389 Grand Oak Trail in Oakville: 1019 - WM Westmount House for sale : MLS®# W13098284
2389 Grand Oak Trail Oakville L6M 4V4 OPEN HOUSE: Jun 06, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, June 6, 2026 2:00PM - 4:00PM
$1,799,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13098284
- Bedrooms:
- 4
- Bathrooms:
- 3
A beautifully renovated family home in the heart of Westmount. Completely updated from top to bottom, this stunning 4-bedroom detached home with a double garage offers a perfect blend of style, space, and functionality. This bright, sun-filled home features a superb open-concept layout with a grand double-storey entrance, elegant living and dining areas, and a beautifully designed kitchen that flows seamlessly into the family room, ideal for both everyday living and entertaining. Upstairs, you'll find a spacious primary suite with a large walk-in closet and a fully updated 5-piece ensuite, along with three further generously sized bedrooms and a renovated main bathroom. The exterior is equally impressive, with a well-landscaped lot, a private backyard, and a large deck perfect for relaxing or hosting. Ideally located with easy access to major highways, public transit, and the GO, and within walking distance to top-rated schools, parks, and trails. A rare opportunity to own a fully renovated, move-in ready family home in one of Oakville's most desirable neighbourhoods. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
- 1 (416) 7350120
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154 Howell Road in Oakville: 1015 - RO River Oaks House for sale : MLS®# W13175470
154 Howell Road Oakville L6H 5Z2 OPEN HOUSE: Jun 07, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, June 7, 2026 2:00PM - 4:00PM
$1,730,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13175470
- Bedrooms:
- 6
- Bathrooms:
- 5
*OPEN HOUSE SUNDAY, JUNE 7th, 2-4pm - 154 HOWELL ROAD, OAKVILLE* Boasting almost 4,600 sq ft of beautifully finished living space, this spectacular executive 5-bedroom, 5-bath family home is located in the highly sought-after River Oaks neighbourhood. Immaculate and completely turn-key, this exceptional residence showcases outstanding attention to detail throughout with extensive mouldings, designer lighting, rich hardwood flooring, and upscale finishes from top to bottom.The thoughtfully designed floor plan offers spacious principal rooms, a desirable main floor office, and an ideal family layout featuring 3 bathrooms on the second level, including a stunning brand new spa-inspired ensuite in the luxurious primary retreat.The heart of the home features elegant decor, beautiful stone countertops, and exceptional spaces for both everyday living and entertaining both inside and out. The deluxe fully finished basement is an entertainer's dream complete with a wet bar, gym area, games space, full bath, fireplace and a wine cellar. Step outside to your own private backyard oasis featuring a massive cedar deck, hot tub, privacy fencing with ambient lighting, and breathtaking landscaping front and back. Shed with electricity. Exceptional curb appeal begins with the flagstone entrance. Ideally situated within walking distance to top-rated schools, parks, trails, recreation centre, shopping, and more, this outstanding home truly offers all the "bells and whistles" for the discerning buyer. Seller can accommodate a 30 day closing! A rare opportunity in one ofOakville's most desirable family communities - you will not be disappointed. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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2372 Saugeen Road in Oakville: 1015 - RO River Oaks House for sale : MLS®# W13176726
2372 Saugeen Road Oakville L6H 5X9 OPEN HOUSE: Jun 06, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, June 6, 2026 2:00PM - 4:00PM
$1,699,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13176726
- Bedrooms:
- 5
- Bathrooms:
- 4
*OPEN HOUSE SATURDAY, JUNE 6th, 2-4pm - 2372 SAUGEEN ROAD, OAKVILLE* Large 5 bedroom family home on one of River Oaks premier streets! Boasting exceptional curb appeal and meticulously landscaped front and back gardens including a pool, this beautifully maintained residence offers over 3,100 sq ft of living space. The main floor features large principal rooms including a dedicated home office. large living and dining rooms, family room with gas fireplace and hardwood flooring. The updated kitchen is filled with natural light and showcases granite countertops, newer appliances, ample white cabinetry, and ideal space for everyday living and entertaining. The second level offers 5 generous bedrooms and 3 bathrooms, including an expansive primary with renovated ensuite featuring a jacuzzi tub, oversized glass shower with multiple body jets, and large walk-in-closet. Room for everyone! Step outside to your private backyard retreat complete with a fabulous inground pool and beautifully maintained landscaping - perfect for summer entertaining and family enjoyment. New pool liner (May 2026). Ideally located within walking distance to excellent schools, parks, Sixteen Mile Trails, shopping, and more. Homes rarely come up for sale on this street -don't miss the opportunity to own a timeless family home in an exceptional neighbourhood. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- MARTHA AIMOLA
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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Data was last updated June 5, 2026 at 09:15 PM (UTC)
RE/MAX Aboutowne Realty Corp., Brokerage
Location
1235 North Service Road West #100
Oakville, ON, L6M 2W2
