Oakville Luxury Real Estate
Trying to find Luxury Oakville homes for sale? Luxury Oakville Real Estate $2.5 Million Homes.
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70 Shorewood Place in Oakville: 1017 - SW Southwest Single Family Residence for sale (1 - Oakville) : MLS®# 40848808
70 Shorewood Place Oakville L6K 3Y4 
$5,250,000Residential- Status:
- Active
- MLS® Num:
- 40848808
- Bedrooms:
- 4
- Bathrooms:
- 6
- Floor Area:
- 6,840 sq. ft.
Exceptional custom-built luxury home with approximately 4,655 sq. ft., plus the professionally finished basement on a premium 185' deep lot with west exposure, on one of Southwest Oakville's coveted lakeside streets. Steps to Lake Ontario, & a 20-minute walk to historic downtown Oakville, Oakville Harbour, trendy shops & restaurants, & close to major highways & GO Station. Outstanding curb appeal highlighting a timeless stone exterior, exposed aggregate driveway, natural stone walkways, iron fencing, irrigation system, manicured gardens & mature trees. The spectacular resort-style, dream backyard features an in-ground saltwater pool, raised hot tub, expansive stone patios, custom gazebo, covered terrace area with ceiling fans & heaters, cabana with serving bar, lush gardens, & a tranquil waterfall & creek surrounded by mature trees for exceptional privacy. The elegant interior features soaring ceilings, hardwood floors, deep crown mouldings, custom cabinetry, pot lights, built-in speakers, 4 gas fireplaces, oversized windows & walkouts, with custom blinds & draperies. Designed for both entertaining & family living, the home offers a stunning open-concept great room off the foyer, formal living room & separate private dining room, spacious family room, & a renovated chef's kitchen (2018) with premium appliances, quartz counters, a large island, breakfast bar & bright breakfast area with walkout to the backyard. Upstairs is a generous laundry room, 4 spacious bedrooms, (4th bedroom currently used as den but can be converted to 4th bedroom) & 3 full bathrooms, including a luxurious primary suite with cathedral-style ceilings, a fireplace, & a renovated 6-piece ensuite (2015). The professionally finished basement features a home theatre, recreation/games room, wet bar, gym & 3-piece bathroom. Additional updates include a new pergola & awning (2024), furnace, air conditioner, & renovated kitchen (2018), re-shingled roof & renovated ensuite bathroom (2015). More detailsListed by Royal LePage Real Estate Services Ltd.- ELENA CIPRIANO
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2458 Meadowood Crescent in Oakville: 1001 - BR Bronte Single Family Residence for sale (1 - Oakville) : MLS®# 40848426
2458 Meadowood Crescent Oakville L6L 1V6
$3,498,000Residential- Status:
- Active
- MLS® Num:
- 40848426
- Bedrooms:
- 4
- Bathrooms:
- 5
- Floor Area:
- 5,684 sq. ft.
Tucked away on a quiet dead-end crescent on one of Bronte's best streets, this custom-built home blends thoughtful design and family-friendly living. It is steps from a park and playground, and within walking distance of Bronte's renowned restaurants, waterfront, and marina.Offering over 3,500 square feet above grade, plus a newly finished basement (2026), every inch has been designed for everyday living and effortless entertaining. A formal foyer creates a beautiful first impression, opening to an elegant living room and private main floor office.The heart of the home is an impressive chef's kitchen with premium appliances, an oversized centre island, and exceptional storage. A butler's pantry seamlessly connects the kitchen to the walk-in pantry and formal dining room. A generous breakfast area flows into the inviting family room, featuring a warm gas fireplace.Designed as an extension of the living space, the professionally landscaped backyard was transformed by ProScape Land Design into a private outdoor retreat. It features a covered dining area with a built-in BBQ, tiered seating beneath a pergola, and a private putting green.Upstairs, the layout offers privacy for everyone. The primary suite is a true retreat with a spa-inspired ensuite and a spacious walk-in closet. Two secondary bedrooms share a beautifully appointed Jack-and-Jill bathroom, while the fourth bedroom enjoys its own private ensuite.The newly completed lower level expands the living space with beautifully finished recreation areas, a custom built-in bar with beverage and wine refrigerators, a wine display, extensive built-in cabinetry, a dedicated home gym, and a convenient two-piece bathroom.From its exceptional custom design and family-friendly layout to its magazine-worthy backyard and unbeatable Bronte location, this home is a fantastic opportunity in one of Oakville's most cherished neighbourhoods. More detailsListed by Century 21 Miller Real Estate Ltd.- ELENA CIPRIANO
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21 Second Street in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40850223
21 Second Street Oakville L6J 3T1
$6,975,000Residential- Status:
- Active
- MLS® Num:
- 40850223
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 2,456 sq. ft.
Lakefront home, nestled on Old Oakville's Second Street, this residence offers a blend of timeless elegance, luxury, and unparalleled waterfront living. Completely reimagined top to bottom, showcasing an aesthetic designed for both family living and comfortable downsizing. Bathed in natural light, offering breathtaking lake views from nearly every room, you will find tranquility and grandeur from the moment you enter. Glowing hardwood flooring, custom millwork and paneling, recessed lighting, and designer finishes elevate every space.The kitchen, with panoramic lake views, features custom cabinetry, integrated top-of-the-line appliances, and an oversized island with seating for four. Quartz countertops and fullheight quartz backsplash create a striking focal point, complemented by gold pendant lighting. The living room is designed for both comfort and style, featuring custom built-in cabinetry with illuminated shelving, gas fireplace, and expansive windows framing the sparkling waters of Lake Ontario. The main-floor primary suite, spacious and serene, featuring a walk-in closet. Spa-inspired ensuite with a freestanding soaker tub, glass walk-in shower, vanity, and gold fixtures and lighting. Two additional bedrooms on the upper level for family and guests, with private balcony overlooking the waterfront. Enjoy a beautifully appointed main-floor laundry room with custom cabinetry and stacked appliances. Enjoy riparian rights from a spectacular waterfront deck featuring glass railings and steps to the shoreline. Maximizing the panoramic water views, an unrivaled setting for entertaining, relaxing, and embracing Oakville's most prestigious waterfront lifestyle. Complete with a detached 2 car garage and ample private parking. Furniture by FOR living, Art by Harbour Gallery. Luxury Certified. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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1077 Bridge Road in Oakville: 1020 - WO West Single Family Residence for sale (1 - Oakville) : MLS®# 40850482
1077 Bridge Road Oakville L6L 2B6
$3,199,900Residential- Status:
- Active
- MLS® Num:
- 40850482
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 5,327 sq. ft.
1077 Bridge Road offers over 5,300 sq. ft. of finished living space on a landscaped 100' x 120' lot in sought-after West Oakville, minutes to downtown Oakville, Bronte Harbour, Lake Ontario, parks, the YMCA, top-rated schools, and Appleby College.A grand foyer with 10-foot ceilings, plaster crown moulding, and a hardwood staircase leads to a private office, formal dining room, and butler's servery with wine fridge. Wide-plank hardwood floors, 9-inch baseboards, custom millwork, coffered ceilings, and a gas fireplace complement the open-concept living space. The chef's kitchen features Sub-Zero, Wolf, and Bosch appliances, a large island, and breakfast area.The second level offers four bedrooms with ensuite access, including a primary suite with a walk-in closet and a heated-floor ensuite. A second bedroom has a private ensuite, while two others share a Jack-and-Jill bath. Second-floor laundry adds convenience.The finished lower level features heated floors, a spacious rec room with a stone gas fireplace, fifth bedroom, 3-piece bath, and flexible space for a gym, media room, or games area.Outside, enjoy a covered porch, stone patio, landscaped backyard with irrigation, Generac whole-home generator, security system, and epoxy-finished double garage. A custom-built home combining quality craftsmanship, functional design, and an exceptional West Oakville location. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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- 1 (905) 6166821
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175 Burloak Drive W in Oakville: 1001 - BR Bronte Single Family Residence for sale (1 - Oakville) : MLS®# 40850447
175 Burloak Drive W Oakville L6L 6E6
$2,699,000Residential- Status:
- Active
- MLS® Num:
- 40850447
- Bedrooms:
- 5
- Bathrooms:
- 6
- Floor Area:
- 3,200 sq. ft.
Welcome to this upscale Southwest Oakville home offering an exceptional lakeside lifestyle, steps from nature & a short drive to conveniences & highways. This sought-after neighbourhood, just 2 blocks from Lake Ontario, close to waterside parks & beaches, is perfect for outdoor enthusiasts. Extensive professionally landscaped grounds, including the private, resort-style backyard, featuring a 14’ x 28’ heated pool with a sheer descent waterfall, LED colour-changing lighting, copper filtration, a spacious concrete patio, & composite wood seating platforms, elevate summer get-togethers. Cameras monitor the building exterior, & Smart technology allows you to control the pool functions & thermostat via an app on your phone. Inside, enjoy approximately 3,200 sq. ft. of luxury living space with 4+1 bedrooms & 5.5 bathrooms, plus the professionally finished basement, & approximately $400,000 in recent upgrades. Premium finishes include 9 & 10-foot ceilings, upgraded hardwood floors, deluxe laminate in the lower level, oversized designer tile in all bathrooms, pot lights, chic light fixtures, wainscotting, a dramatic 2-storey mirrored foyer feature wall, & the floating oak staircase with glass railings is beyond impressive. The main level offers a formal living & dining area, a family room with a coffered ceiling & gas fireplace, a private office, powder room, & laundry with garage access. The chef’s eat-in kitchen features quartz countertops, deluxe white cabinetry, a butler’s pantry, a centre island, premium appliances, & walkout to the dream backyard. Upstairs, you’ll find 4 spacious bedrooms, each with walk-in closets & dedicated ensuite bathrooms, including the primary suite with a tray ceiling, an electric fireplace & spa-like five-piece ensuite. The finished lower level includes a large rec room with an electric fireplace & wet bar, a fifth bedroom, & a stylish 3-piece bath—ideal for entertaining, extended family, or guests. More detailsListed by Royal LePage Real Estate Services Ltd.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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287 Macdonald Road in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40851190
287 Macdonald Road Oakville L6J 2A6
$3,949,000Residential- Status:
- Active
- MLS® Num:
- 40851190
- Bedrooms:
- 4
- Bathrooms:
- 5
- Floor Area:
- 4,819 sq. ft.
This completely renovated contemporary residence represents the pinnacle of modern design and sophisticated living in one of Oakville's most desirable locations of Old Oakville. Every detail of this 4 Bedroom | 4+1 Bathrooms | 4,819 Sq Ft Finished Living Space has been meticulously reimagined to deliver an unparalleled standard of quality and craftsmanship.The highly functional main floor plan centers around an exceptionally sleek kitchen open to the Great Room with gas fireplace and walk out to the resort style backyard and pool.The kitchen is outfitted with luxury high-end appliances, an oversized island seating eight, and an additional peninsula for casual entertaining in the bar area. Adjacent to the kitchen, is a walk in pantry with an additional dishwasher and fridge. Not to be missed is the impressive temperature-controlled wine room accommodates approx 1,000 bottles-a striking feature for the discerning entertainer.A versatile family room/main floor bedroom with ensuite which can be used as a principal bedroom or guest suite, laundry room, walk-in main closet for storage and access to oversized double car garage.The 2nd level principal suite is a private sanctuary featuring juliette balcony, gas fireplace, two walk-in closets and a spa-inspired ensuite with heated floors, walk-in shower, and a standalone soaking tub.Two additional spacious bedrooms each with their own ensuites complete the level.Not to be missed is the finished lower level room with added storage in the pantry and crawl space area.The backyard is an entertainer's paradise, showcasing a saltwater pool, two expansive patio areas, two gazebos with a gas fire table, and premium Dutch-imported artificial turf that remains lush year-round with zero maintenance.Ideally situated steps from Whole Foods Market, Oakville GO Train, for seamless transit connectivity, and the Oakville Trafalgar Community Centre this extraordinary property offers both refined luxury & everyday convenience. LUXURY CERTIFIED More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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- 1 (905) 6166821
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201 Trelawn Avenue in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40851384
201 Trelawn Avenue Oakville L6J 4R3
$3,265,000Residential- Status:
- Active
- MLS® Num:
- 40851384
- Bedrooms:
- 4
- Bathrooms:
- 3
- Floor Area:
- 1,672 sq. ft.
Welcome to this exceptional, completely rebuilt and renovated detached bungalow nestled in one of Southeast Oakville's most sought-after neighborhoods. Set on a rare, oversized lot, one of the largest on the street, this 3+1 bedroom, 3-bathroom home offers approximately 3,000 square feet of beautifully finished living space designed for comfort, elegance, and functionality. Step inside to discover soaring cathedral ceilings, an open-concept layout filled with natural light, and a seamless blend of luxury and warmth. The custom kitchen with high-end appliances flows effortlessly into the spacious living and dining areas, perfect for entertaining or everyday living. A private primary suite with a 150 square foot addition features a spa-inspired ensuite and serene views. The fully finished walk-out basement includes a large lower-level living area, guest bedroom with walkout, full bathroom, and generous storage, ideal for extended family, a home office, or nanny/in-law suite. Step outside to your expansive deck, ideal for summer gatherings and outdoor dining. The professionally landscaped yard is equipped with a full irrigation system, making lawn and garden maintenance a breeze. Located in prestigious Southeast Oakville, this home is surrounded by top-rated schools, mature trees, and quiet, family-friendly streets, offering a rare combination of privacy and convenience. More detailsListed by The Agency- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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54 Raymar Place in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40852110
54 Raymar Place Oakville L6J 6M1
$7,249,000Residential- Status:
- Active
- MLS® Num:
- 40852110
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 7,241 sq. ft.
Welcome to 54 RAYMAR PL, OAK ON L6J 6M1, a single-family residence built in 1988 that has undergone a complete transformation. This property, fully updated from its recently refreshed exterior to its meticulously remodeled interior, offers a contemporary aesthetic designed for modern living. The heart of this home is undoubtedly the recently updated kitchen, a culinary enthusiast's dream. It features a generous island with a built-in sink, providing ample space for preparation and casual dining, complemented by a convenient wine cooler. Adjacent to this, the living room provides a comfortable gathering space, enhanced by the warmth of a fireplace. The bathrooms throughout the home offer a touch of luxury, with features such as double vanities, floating vanities, and invigorating walk-in showers. Beyond the interior, the private yard is an entertainer's paradise, offering an outdoor living space complete with a fire pit and a dedicated outdoor dining area. For ultimate relaxation, indulge in the private pool or unwind in the private outdoor hot tub. The property also includes a workshop and a patio, along with a built-in garage providing four spaces for vehicles. Discover the exceptional lifestyle this meticulously updated property offers; schedule your private viewing today. Over 7000 Square ft. of Living Space. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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2073 Deramore Drive in Oakville: 1006 - FD Ford Single Family Residence for sale (1 - Oakville) : MLS®# 40853020
2073 Deramore Drive Oakville L6J 2P7
$3,125,000Residential- Status:
- Active
- MLS® Num:
- 40853020
- Bedrooms:
- 5
- Bathrooms:
- 4
- Floor Area:
- 4,356 sq. ft.
Tucked away in prestigious Southeast Oakville, this extraordinary custom-built bungalow tells a story of timeless elegance and effortless family living. Offering 4,356 sq. ft. of beautifully crafted space on a premium lot, every corner of this home was designed for comfort, connection, and refined everyday living. Beyond the doors, a private backyard retreat and expansive deck create the perfect setting for quiet mornings, lively gatherings, and evenings under the stars. Inside, soaring 10-foot ceilings and rich hickory hardwood floors guide you through sun-filled formal living and dining spaces, warmed by a gas fireplace and framed by grand 8-foot sliding doors. At the heart of the home, the chef-inspired kitchen invites everyone to gather, featuring granite countertops, a Bertazzoni gas stove, a charming Belfast sink, and a bright breakfast area opening seamlessly to the deck for indoor-outdoor living. The main-floor primary suite is a peaceful retreat with French doors to the deck, a walk-in closet, and a spa-inspired five-piece ensuite with a clawfoot soaker tub. Two additional bedrooms on the main level offer flexibility for family or guests. Downstairs, the finished lower level extends the story with a recreation room, second gas fireplace, games area, wet bar, laundry, and two additional bedrooms ideal for extended family, guests, or a home office. Car enthusiasts will appreciate the double garage with soaring ceilings ready for a lift, wiring for an EV charger, and a double-wide driveway accommodating up to six vehicles. Designed for seamless one-level living, this home offers the perfect balance of luxury and practicality for families, professionals, and downsizers alike. Just moments from Oakville Trafalgar High School, Deer Run Park, and Sobeys Maple Grove, this move-in ready residence captures the best of Southeast Oakville living where sophistication, warmth, and memories come together. Luxury Certified. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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- 1 (905) 6166821
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2288 Chancery Lane W in Oakville: 1006 - FD Ford Residential for sale (1 - Oakville) : MLS®# 40852234
2288 Chancery Lane W Oakville L6J 6A3
$6,499,000Land- Status:
- Active
- MLS® Num:
- 40852234
Some properties simply cannot be replicated. Set along one of South East Oakville's most prestigious waterfront streets, this exceptional offering represents one of the area's last opportunities to create a truly landmark custom estate. Occupying approximately 0.59 acres with 99 feet of private pebble shoreline, Riparian Rights and nearly 300 feet of depth, the property enjoys breathtaking, uninterrupted views across Lake Ontario while mature trees provide an extraordinary sense of privacy. The property offers an exceptional backdrop for a custom residence designed to embrace every aspect of waterfront living. With the potential to build over 8,000 sqft custom home (plus basement, subject to all applicable approvals), the possibilities are endless. Grand principal rooms, seamless transitions to outdoor living spaces and resort-inspired amenities can all be thoughtfully incorporated to maximize the property's panoramic lake views. Life on the water becomes part of your everyday routine. Launch a kayak or paddleboard directly from your own shoreline, enjoy coffee overlooking the lake, or simply experience the tranquility that only true lakefront living can provide. Despite its remarkable sense of seclusion, the property is only minutes from Downtown Oakville's boutique shops, acclaimed restaurants, marinas and waterfront amenities. Located within one of Ontario's most highly regarded school districts, this is an opportunity to create not simply a home, but a lasting family legacy in one of South East Oakville's most exclusive lakefront communities. More detailsListed by Century 21 Miller Real Estate Ltd.- ELENA CIPRIANO
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- 1 (905) 6166821
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436 Willis Drive in Oakville: 1020 - WO West Single Family Residence for sale (1 - Oakville) : MLS®# 40853404
436 Willis Drive Oakville L6L 4V5
$3,258,000Residential- Status:
- Active
- MLS® Num:
- 40853404
- Bedrooms:
- 5
- Bathrooms:
- 7
- Floor Area:
- 3,400 sq. ft.
Situated on an impressive 62' x 156' lot with desirable south-west exposure in prestigious West Oakville, this exceptional custom-built smart home was crafted with an extraordinary level of detail, offering approx. 5,280 sq. ft. of luxurious finished living space (3,400 sq. ft. above grade), 5 bedrooms, 5 full bathrooms & 2 powder rooms. Premium finishes include 10' main-floor ceilings, 9' upper/lower levels, massive Velux skylight, oversized windows, crown moulding, wainscoting, heated floors, built-in speakers, smart-home automation & multiple gas fireplaces. The designer Perola kitchen showcases custom cabinetry, leathered Calcutta granite island, Caesarstone counters, JennAir appliances, 6-burner gas cooktop with pot filler, wine fridge & pantry. The stunning great room features custom built-ins, accent lighting, gas fireplace & expansive backyard views. Elegant living/dining rooms offer imported crystal chandeliers, hardwood & custom millwork, while the private office features solid wood French doors, built-ins & CAT6 wiring. Retreat upstairs to the luxurious primary suite with vaulted ceilings, picture windows, built-in speakers, custom walk-in closet & spa-inspired heated 5-piece ensuite. Additional bedrooms feature heated ensuite bathrooms & custom built-ins. The professionally finished walk-up lower level offers heated floors, home theatre, games/rec areas, gas fireplace, wine bar rough-in & additional bedroom with ensuite. Outside, enjoy Indiana limestone accents, mahogany doors, irrigation, security cameras & parking for 6. Integrated controls for lighting, security, HVAC & audio complete this meticulously crafted luxury residence. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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197 Polly Drive in Oakville: 1008 - GO Glenorchy Single Family Residence for sale (1 - Oakville) : MLS®# 40853392
197 Polly Drive Oakville L6M 5K2
$3,358,000Residential- Status:
- Active
- MLS® Num:
- 40853392
- Bedrooms:
- 6
- Bathrooms:
- 6
- Floor Area:
- 5,600 sq. ft.
Some homes make a statement the moment you arrive. Others reveal themselves gradually, each space uncovering another layer. This remarkable residence does both. Set on a premium ravine lot backing onto mature woodland and walking trails, extensive custom stone landscaping frames both the front and rear gardens, creating an arrival that offers little hint of what awaits within. Step inside and the experience begins. A sculptural floating staircase, soaring 10-foot ceilings and expansive European windows draw your attention to the wooded ravine beyond. Scandinavian-inspired interiors, wide-plank white oak floors, dramatic slab feature walls and bespoke millwork create a calm contemporary aesthetic where architecture, craftsmanship and nature exist in perfect balance. At the heart of the home, an exceptional chef’s kitchen is anchored by a dramatic natural quartzite waterfall island, beautifully crafted cabinetry, integrated appliances and thoughtful design that brings everyday living and effortless entertaining together. Upstairs, generous family accommodation gives way to a private primary retreat. A dramatic three-sided fireplace, bespoke walk-in dressing room with custom Italian cabinetry and a beautifully appointed spa-inspired ensuite create a peaceful sanctuary at the end of each day. The finished lower level expands the home’s possibilities with a private theatre and recreation lounge, together with a beautifully finished legal two-bedroom secondary suite featuring its own entrance, full kitchen, separate laundry and oversized windows. Ideal for multigenerational living, extended family, guests or supplementary income, it offers exceptional flexibility without compromise. Beautifully conceived inside and out, this is a home where exceptional design serves everyday living rather than demanding attention. Some homes are admired for their finishes. Rare ones, like this, are remembered for how they make you feel. More detailsListed by RE/MAX Aboutowne Realty Corp.- ELENA CIPRIANO
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- 1 (905) 6166821
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Data was last updated September 7, 2026 at 09:50 PM (UTC)
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