Oakville Luxury Real Estate
Trying to find Luxury Oakville homes for sale? Luxury Oakville Real Estate $2.5 Million Homes.
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116 Chartwell Road in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40784042
116 Chartwell Road Oakville L6J 3Z6 
$8,250,000Residential- Status:
- Active
- MLS® Num:
- 40784042
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 5,570 sq. ft.
Welcome to 116 Chartwell Road, a stunning Net Zero certified masterpiece in South East Oakville, blending luxury, sustainability, and wellness. Designed by David Small Designs & crafted by Troika Custom Builders, this eco-friendly gem prioritizes your health with a fully sealed envelope, advanced insulation, and a geothermal system paired with a 14.49kW solar array. This ensures clean, energy-efficient living, reducing exposure to pollutants and maintaining superior indoor air quality for a healthier, more comfortable home. Step inside to an open-concept layout bathed in natural light with floor-to-ceiling windows and a striking pyramid skylight. Beautiful wire-brushed white oak flooring with in-floor heating is throughout the home. The gourmet kitchen features a Diamante Quartzite island, custom lacquered cabinetry, and top-tier Gaggenau appliances perfect for healthy, home-cooked meals. Outdoors, a stylish covered patio with a mahogany-clad ceiling, dual Kenyon barbecues, a stainless steel hot tub and surround sound creates an inviting space for relaxation and entertaining. The main floor primary suite is a serene retreat with a walk-through dressing room and a luxurious 5-piece ensuite featuring a steam shower and oversized soaking tub, promoting relaxation and well-being. The home office with garden views and a floor-to-ceiling oak bookcase offers a calming workspace. Upstairs, two spacious bedrooms with ensuites ensure comfort for family or guests. The lower level is an entertainment hub with a fitness room for active lifestyles, a recreation room with a built-in bar and pool table, and an additional bedroom with ensuite. Smart home technology seamlessly integrates audio-visual, lighting, and security systems, controlled via intuitive apps and two master control rooms, ensuring peace of mind. A tandem four-car garage with a hydraulic lift and EV charging, plus extra outdoor parking, speaks to the car enthusiast. More detailsListed by Sotheby's International Realty Canada- ELENA CIPRIANO
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1168 Carey Road in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40784716
1168 Carey Road Oakville L6J 2E4
$3,750,000Residential- Status:
- Active
- MLS® Num:
- 40784716
- Bedrooms:
- 3
- Bathrooms:
- 4
- Floor Area:
- 3,128 sq. ft.
Nestled on over a 1/3 of an acre in prestigious Eastlake,this architecturally designed custom contemporary masterpiece redefines luxury living with its sophisticated blend of form and function.The commanding entrance welcomes you through a thoughtfully crafted foyer featuring a striking accent wall,setting the tone for design elements that unfold throughout this 3,128 sq ft sanctuary. Natural light becomes the home's greatest asset,flooding every space through expansive floor-to-ceiling windows that create breathtaking sight lines and seamless indoor-outdoor connections.The L/R showcases vaulted ceilings,gas f/p w/ a distinctive brick feature wall that serves as both warmth & artistic focal point. The kitchen offers culinary experiences w/integrated b/i appliances,skylight,breakfast nook,& walk-in pantry for the discerning chef.The adjoining F/R offers a casual place to relax by the cozy wood burning f/p.A separate D/R provides versatility for both casual sophisticated entertaining. The primary bdrm offers private yard access thru the w/o,a cathedral T&G willow ceiling,W/I closet & 4 pc ensuite.2 add’l bdrms feature dramatic floor-to-ceiling windows & dble closets for optimal storage solutions. The 4-season garden room emerges as pure enchantment,bathed in natural radiance from its wall of windows overlooking manicured patio spaces,enhanced by 3 skylights that create an almost ethereal atmosphere thru/out changing seasons. Below the LL maximizes functionality w/ rec room,oversized laundry & craft area,3 pc bath,workshop,W/I cedar storage & add’l storage areas for your organizational needs. Exterior craftsmanship shines through cedar roof,siding,& soffits.Impressive dble grg features carport area w/parking for 12 vehicles, accessed via an elegant granite cobblestone driveway.Architecturally designed landscaping. Uncompromised quality abounds!This home has been loved for 45 years by its current owner & now awaits for it to be your next home. Luxury Certified. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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115 Charnwood Drive in Oakville: 1006 - FD Ford Single Family Residence for sale (1 - Oakville) : MLS®# 40784665
115 Charnwood Drive Oakville L6J 5G8
$3,498,000Residential- Status:
- Active
- MLS® Num:
- 40784665
- Bedrooms:
- 6
- Bathrooms:
- 5
- Floor Area:
- 5,808 sq. ft.
If you have a large family, this home just may be the perfect fit! Completely renovated inside and out, offering an impressive 4,242 sq ft above grade and six spacious bedrooms, an exceptional find in any neighbourhood! Every room is generously sized, even the mudroom, a layout truly designed for family life. The timeless Cape Cod exterior features an oversized double garage and sits on a stunning 16,000+ sq ft lot, fully fenced, ultra private, and ideal for family fun. There’s an enormous pool with surrounding deck, plus a covered porch and plenty of green space for play or relaxation. Inside, the main floor sprawls with rich espresso hardwood, two staircases, and fresh paint throughout. The custom kitchen offers hardwood cabinetry, white countertops, a work station, top-tier appliances, a pantry and abundant seating, all anchored by a sun-filled breakfast area that opens to the backyard oasis. The dining room is large enough for any gathering, yet it's the even larger family room that steals the show, with wall-to-wall windows, a fireplace and room for as much seating as you could want. Upstairs, the six bedrooms offer unmatched flexibility: convert one or two into offices, playrooms, or guest suites. The primary retreat includes a vaulted ceiling, large walk-in closet and a hotel-inspired ensuite, your own private escape. The lower level features a full walk-up, home gym, full bath, sauna and an oversized rec room. With immediate occupancy available, you can enjoy summer in this one-of-a-kind home. A true rarity in both space and style. More detailsListed by Century 21 Miller Real Estate Ltd.- ELENA CIPRIANO
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PH1 300 Randall Street in Oakville: 1013 - OO Old Oakville Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40786091
PH1 300 Randall Street Oakville L6J 0G2
$5,999,900Residential- Status:
- Active
- MLS® Num:
- 40786091
- Bedrooms:
- 3
- Bathrooms:
- 4
- Floor Area:
- 3,337 sq. ft.
RESTORATION HARDWARE SHOW SUITE: Welcome to the crown jewel of The Randall Residences, Oakville's most prestigious address. This sun-filled Signature Penthouse Suite is the largest residence inside and out, offering approximately 3,337 sq. ft. of sophisticated living plus a 386 sq. ft. second-storey lounge with skylight and an expansive 1,327 sq. ft. southeast-facing terrace. Enter through a grand rotunda foyer with marble floors and an impressive RH chandelier, setting the tone for this exceptional home. The open-concept living and dining areas boast 12-foot ceilings, floor-to-ceiling wrap-around windows, custom Downsview cabinetry, top-of-the-line appliances, and a gas fireplace - an entertainer's dream. Restoration Hardware fixtures illuminate throughout the suite exuding an atmosphere of sophisticated refinement. The principal bedroom retreat is a haven of tranquility with a custom zebra-wood dressing room and a spa-inspired 6-piece ensuite, complete with heated marble floors, polished nickel fixtures, and a freestanding soaking tub. Two additional bedrooms each feature their own private ensuites for ultimate comfort and privacy. Ascend to the second-storey lounge, ideal for a home gym, office, or serene retreat, and step out to your private rooftop terrace designed for entertaining, featuring multiple lounging and dining zones with a gas BBQ hookup. Additional luxuries include a Crestron home automation system, integrated entertainment features, 3 parking spaces, and 2 storage lockers. Residents enjoy 24-hour concierge service in this award-winning development, celebrated for its impeccable craftsmanship and timeless elegance. Sotto Sotto on the ground floor. Located steps from Lake Ontario, fine dining, boutique shopping, and just minutes to major highways, this penthouse represents the pinnacle of luxury living in Oakville. If you demand the best, look no further. Luxury Certified More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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1081 Argyle Drive in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40786555
1081 Argyle Drive Oakville L6J 1A9
$7,999,000Residential- Status:
- Active
- MLS® Num:
- 40786555
- Bedrooms:
- 5
- Bathrooms:
- 7
- Floor Area:
- 10,077 sq. ft.
An architectural masterpiece by renowned Gren Weis, this exceptional residence offers over 10,000 sq. ft. of luxurious living space on more than ½ an acre in one of Oakville’s most desirable lake-influenced neighbourhoods. Showcasing soaring ceilings, extensive millwork, and superb craftsmanship, the home features spacious, elegant rooms and a seamless flow for entertaining. All bedrooms include ensuite baths, while the lower level impresses with a wine cellar and theatre. Outside, enjoy covered terraces, a built-in outdoor kitchen, luxury cabana, mature gardens, and a stream with bridge surrounded by landscape lighting. A classically inspired front fountain and spectacular landscaping enhance the property’s distinguished presence on an important street. Close to top private and public schools, this private estate blends timeless design, quality, and sophistication in a truly remarkable setting. Luxury Certified. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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- 1 (905) 6166821
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2372 Carrington Place in Oakville: 1006 - FD Ford Single Family Residence for sale (1 - Oakville) : MLS®# 40786992
2372 Carrington Place Oakville L6J 5P4
$5,999,000Residential- Status:
- Active
- MLS® Num:
- 40786992
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 3,940 sq. ft.
WATERFRONT PROPERTY! Experience the Beauty of Lakeside Living Perfectly situated on a premium 90’ x 152’ lakefront lot, this residence captures breathtaking, unobstructed water views from every principal room. Offering over 5,700 square feet of finished living space, the home seamlessly blends timeless lakeside elegance with modern comfort and functionality. Step inside to discover a light-filled interior where functionality meets everyday comfort. Rich hardwood flooring, limestone tiles, and four skylights create a warm and inviting ambiance throughout. Designed with both family living and entertaining in mind, the main level features two spacious family rooms, a private office, and a gourmet kitchen complete with granite countertops, premium appliances, and abundant cabinetry. Upstairs, four generously sized bedrooms offer space and privacy for the entire family. The primary suite is a true retreat, showcasing spectacular lake views. A convenient upper-level laundry room adds to the home’s thoughtful design and a walkout to the second-floor terrace — the perfect place to unwind and enjoy tranquil sunsets over the water The fully finished lower level extends the living space, featuring a fifth bedroom with a private ensuite — ideal for guests, in-laws, or a nanny suite. Outdoors, the backyard is an entertainer’s dream. Featuring the concrete saltwater in-ground pool, landscaped gardens, and multiple seating areas designed to make the most of the home’s stunning lakefront setting. Whether hosting summer gatherings or relaxing quietly by the water, this space offers a waterfront lifestyle experience. Additional highlights include a three-car garage, four fireplaces, an irrigation system, and ample storage throughout. This property embodies the very best of lakeside living — offering endless possibilities for its next owner to further enhance and celebrate the home’s inherent beauty, and sophisticated waterfront setting. Luxury Certified. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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- 1 (905) 6166821
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481 Chartwell Road in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40789810
481 Chartwell Road Oakville L6J 4A6
$4,695,000Residential- Status:
- Active
- MLS® Num:
- 40789810
- Bedrooms:
- 6
- Bathrooms:
- 6
- Floor Area:
- 6,720 sq. ft.
Beautifully built and impeccably finished, this custom residence offers more than 6,700 square feet of living space in one of Oakville’s most sought-after neighbourhoods. Stone construction, a solid wood entry door, heated garage floors, and timeless architectural detailing set the tone for the quality found throughout the home. Inside, the foyer features heated marble tile, plaster crown mouldings, poplar baseboards, and sightlines that lead into bright, open spaces. A dramatic dining room anchors the main level with a soaring skylight, custom wall panelling, integrated speakers, and carefully curated lighting. The chef’s kitchen is designed with extensive custom cabinetry, quartz countertops, a large island, and easy flow to the family room. The servery and mudroom connect seamlessly; each finished with thoughtful storage and heated floors. Upstairs, all four bedrooms are generously scaled and feature private ensuite baths. The primary suite includes a fireplace, custom walk-in closet, and a beautifully coordinated ensuite with heated floors, a freestanding tub, glass shower, and frosted-glass water closet. A full-size laundry room with cabinetry and folding space completes this level. The lower level offers exceptional versatility with radiant in-floor heating, two additional bedrooms, a three-piece bath with sauna, a recreation room with fireplace, a wet bar/kitchen setup, and a dedicated theatre room beneath the back porch. Wide walk-up access brings in natural light and creates an ideal in-law or extended-family space. Outdoors, the large stone terrace features a gas fireplace and outdoor kitchen with built-in BBQ, extending the home’s entertaining potential. Motorized blinds, CAT-6 wiring, solid core doors, and an oak staircase with glass panels highlight the home’s elevated craftsmanship. With top-ranked schools, shopping, GO access, and major highways nearby, this is a quality home in a prime location. More detailsListed by Century 21 Miller Real Estate Ltd.- ELENA CIPRIANO
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- 1 (905) 6166821
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38 Shorewood Place in Oakville: 1017 - SW Southwest Single Family Residence for sale (1 - Oakville) : MLS®# 40790661
38 Shorewood Place Oakville L6K 3Y4
$4,895,000Residential- Status:
- Active
- MLS® Num:
- 40790661
- Bedrooms:
- 4
- Bathrooms:
- 6
- Floor Area:
- 8,257 sq. ft.
Exclusive lakeside community on a tree-lined private court in south Oakville, just steps from downtown. This sprawling 8,257 sq.ft. of total living space custom residence, set on a 17,500 sq.ft. pie-shaped lot and only one home from the lake, is like none other! Its timeless elevation is framed by extensive natural stone hardscaping (with heated drive and walkway) gunite pool and hot tub (equipment More detailsListed by Century 21 Miller Real Estate Ltd. and Century 21 Mller Real Estate Ltd.- ELENA CIPRIANO
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- 1 (905) 6166821
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247 Douglas Avenue in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40791357
247 Douglas Avenue Oakville L6J 3S2
$3,850,000Residential- Status:
- Active
- MLS® Num:
- 40791357
- Bedrooms:
- 4
- Bathrooms:
- 3
- Floor Area:
- 4,873 sq. ft.
Century Home Updated for Modern Living. Timeless charm meets modern sophistication in Old Oakville.This meticulously maintained home sits on a premium 72’X150’ lot & spans almost 5,000 sq ft of thoughtfully designed living space,with large,light-filled rooms and a main floor layout perfect for entertaining.A generous principal bdrm retreat added in 2010,and extensive renovations by architect John Wilmott & Whitehall Construction 2020. Step inside and discover a bright entryway that flows seamlessly into an elegant living room w/wood burning f/p and a formal dining room perfect for special occasions.The stylish yet practical custom kitchen showcasing Povey cabinetry & high-end appliances that will appeal to any chef.Convenient coffee nook & sleek hidden appliance cabinets maintain a streamlined,clutter-free aesthetic.Sun-filled windows throughout the kitchen and family room overlook the expansive backyard,while the family room centers around a charming Vermont Castings wood-burning f/p.A large private office,complete w/built-in cabinetry & pocket doors,provides the ideal workspace. Upstairs,discover the luxurious primary bdrm retreat featuring walk-in closet & 5-pc ensuite w/heated floors.3 addt’l bdrms incl 1 perfect for a home gym,a full 4pc bathroom w/heated floors along with 2 generous-sized linen closets complete the upper level. The lower level offers exceptional entertainment spaces with a recreation area,a home theatre for movie nights,and craft room for your creative pursuits.A convenient laundry room with abundant storage adds practical value. Outside,the oversized detached insulated and heated 2-car garage includes 2 attached sheds for storage.The driveway accommodates 8 vehicles while a full irrig system complete w/planter drip lines maintains the lush landscaping. Located steps from vibrant downtown,Whole Foods & lake,w/convenient access to the GO & hwys,this home delivers convenience & style in Oakville's most desirable location. Luxury Certified More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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- 1 (905) 6166821
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334 Third Line in Oakville: 1020 - WO West Single Family Residence for sale (1 - Oakville) : MLS®# 40791799
334 Third Line Oakville L6L 4A4
$3,499,000Residential- Status:
- Active
- MLS® Num:
- 40791799
- Bedrooms:
- 5
- Bathrooms:
- 7
- Floor Area:
- 6,225 sq. ft.
A showpiece of refined luxury, this home sits on an impressive 77' x 147' lot, where timeless design blends seamlessly with modern sophistication. The grand circular driveway, multiple entry points, and striking stone water feature create an unforgettable arrival experience. Inside, 12-foot ceilings, expansive floor-to-ceiling windows, a custom moss feature wall, and rich hardwood flooring establish a warm yet dramatic atmosphere throughout. At the heart of the home lies a chef-inspired kitchen, thoughtfully designed with sleek quartz countertops, a 10-foot waterfall island, premium built-in stainless steel appliances, central vacuum, kitchen dustpan/sweep inlet and custom full-height cabinetry that elevates both style and function. Upstairs, 10-foot ceilings enhance the sense of space, while the primary suite offers a true private retreat with a custom fireplace, an oversized walk-in closet with tailored organizers, and a spa-like ensuite featuring dual vanities, a deep soaker tub, a glass-enclosed rain shower, and refined finishes. Each additional bedroom includes its own ensuite, ample natural light, and premium details that create individual private sanctuaries. The fully finished lower level provides exceptional versatility, functioning as a self-contained rental suite or a comfortable in-law space with two spacious bedrooms, two full bathrooms, and an open-concept kitchen equipped with upgraded appliances. Outside, the beauty continues with professionally landscaped grounds, fruit trees, a full sprinkler system, a custom deck, and a covered pergola—perfect for outdoor entertaining and year-round enjoyment. A rare offering that exemplifies superior craftsmanship, thoughtful design, and contemporary luxury living More detailsListed by RE/MAX Aboutowne Realty Corp.- ELENA CIPRIANO
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- 1 (905) 6166821
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2073 Deramore Drive in Oakville: 1006 - FD Ford Single Family Residence for sale (1 - Oakville) : MLS®# 40792445
2073 Deramore Drive Oakville L6J 2P7
$3,699,000Residential- Status:
- Active
- MLS® Num:
- 40792445
- Bedrooms:
- 5
- Bathrooms:
- 4
- Floor Area:
- 4,356 sq. ft.
Step into this extraordinary custom-built bungalow, located in prestigious Southeast Oakville, where refined elegance meets versatile, family-friendly living—perfect for discerning homeowners of all ages. With 4,356 sq. ft. of impeccably designed space on a premium lot, this home harmonizes comfort, functionality, and sophisticated style. The backyard and deck offer a private sanctuary for entertaining, relaxing, or enjoying outdoor indulgence. The main floor features soaring 10-foot ceilings and gleaming hardwood floors throughout. Formal dining and living areas welcome you with a gas fireplace and abundant natural light from 8-foot sliding doors. The open-concept kitchen is a chef’s dream, featuring granite countertops, a Bertazzoni gas stove, a distinctive Belfast sink, and a breakfast area that opens onto the deck for effortless indoor-outdoor living. Retreat to the luxurious primary suite, complete with a five-piece ensuite including a clawfoot soaker tub, a spacious walk-in closet, and French doors to the deck. Two additional main-level bedrooms provide ample space for family or guests. The finished lower level expands your living options with a recreation room featuring a gas fireplace, games area, wet bar, laundry, and two more bedrooms—perfect for extended family, a home office, or a guest suite.Car enthusiasts will appreciate the double-car garage with high ceilings ready for a car lift, alongside a double-wide driveway for six vehicles. Living on one level offers convenience, accessibility, and effortless flow, appealing to families, professionals, or anyone valuing comfort without compromise. Located in prestigious Southeast Oakville, this home is steps from top-rated schools including Oakville Trafalgar High School, Deer Run Park, Sobeys Maple Grove, and excellent transit connections. This move-in-ready bungalow delivers the ultimate Southeast Oakville lifestyle, where luxury, functionality, and timeless comfort come together. Luxury Certified. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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1483 The Links Drive in Oakville: 1007 - GA Glen Abbey Single Family Residence for sale (1 - Oakville) : MLS®# 40782483
1483 The Links Drive Oakville L6M 2P2
$3,088,000Residential- Status:
- Active
- MLS® Num:
- 40782483
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 3,414 sq. ft.
Experience the ultimate in luxury living, style, & location in this extensively renovated 4+1-bedroom, 4.5-bathroom executive home in the prestigious Fairway Hills community, bordering the world-renowned Glen Abbey Golf Course. The backyard is a private resort-style haven, featuring an inground pool, relaxing hot tub, & expansive stamped concrete patios—perfect for summer entertaining & outdoor living. Inside, the main & upper levels underwent a complete designer transformation in August 2024, with walls removed to create a sophisticated, open layout. Every detail exudes elegance with new bathrooms, white oak hardwood floors, crown mouldings, a custom staircase, designer lighting, smooth ceilings, baseboards, trim, interior & exterior doors, windows, & a show-stopping chef’s kitchen. The roof, pool liner, & cover were also newly replaced for peace of mind. Enjoy effortless entertaining in the spacious living room with an inviting fireplace, the formal dining room with custom built-ins, & the oversized family room with a fireplace. The stunning custom kitchen boasts sleek cabinetry with accent lighting, quartz countertops, a large island with a breakfast bar, high-end appliances, including a 6-burner Wolf gas range, & a walkout to your backyard retreat. Upstairs, discover 4 bright bedrooms & 3 spa-inspired bathrooms, including a serene primary suite with custom cabinetry & a luxurious 5-piece ensuite featuring a sculpted soaker tub & oversized glass shower. The fully finished lower level offers endless possibilities with a sprawling recreation room, fireplace, wet bar, games area, a private guest suite & a luxurious full bath. Start your dream life in Glen Abbey, a highly coveted Oakville community celebrated for its scenic trails, top-rated schools, & unbeatable proximity to restaurants, shopping, hospital & major highways. Fairway Hills Association fee $1000/year More detailsListed by Royal LePage Real Estate Services Ltd.- ELENA CIPRIANO
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- 1 (905) 6166821
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Data was last updated February 8, 2026 at 09:50 PM (UTC)
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