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Browse All Oakville ON Properties with Pool for Sale

3348 Skipton Lane, Oakville
$2,979,000
5 Beds ⋅ 5 Baths ⋅ W13779562 MLS
Set on approx. 0.29 acres and backing directly onto Bronte Creek Provincial Park, this fully renovated family home offers exceptional privacy and over 5,500 sq. ft. of upgraded living space in Oakville's sought-after Bronte Creek community. Tucked away on a quiet crescent on one of the neighbourhood's largest lots, the property features professional landscaping, stamped concrete walkway, porch and French curbs, plus a 3-door, 2.5-car garage with epoxy floors, Garaga cabinetry/storage systems and EV charger. The backyard oasis features a covered patio, pool, cabana with bar and change room, and plenty of green space. Inside, the open-concept design showcases hardwood flooring, crown moulding, wainscoting, pot lights and designer lighting throughout. The main level offers formal living and dining rooms with coffered ceilings, private office, hall skylight and family room with custom built-ins and gas fireplace. The chef-inspired kitchen features quartz counters and backsplash, large island, Wolf stove, Sub-Zero fridge and breakfast area with walk-out. Main-floor laundry includes custom built-ins and sink. Upstairs are 4 spacious bedrooms, including a primary retreat with custom TV built-ins, W/I closet with organizers and spa-inspired ensuite. Bedrooms 2 & 3 share semi-ensuite access, while bedroom 4 has a W/I closet and private ensuite. The finished lower level features 9' ceilings, rec/living area with custom built-ins, wet bar, gym, 5th bedroom and full bath. Updates: renovation (2020), roof (2023), front windows (2025), pool pump (2023) & liner (2025). Walk to top-rated schools, parks & amenities; minutes to highways & transit.

3348 Skipton Lane, Oakville

231 Wedgewood Drive, Oakville
$6,399,998
6 Beds ⋅ 8 Baths ⋅ W13777260 MLS
Welcome to an approx. 7,500 sq ft of exceptional living in Southeast Oakville! Set on a professionally landscaped almost half-acre lot in the prestigious Eastlake, this custom Hightower-built estate offers thoughtfully designed, luxurious space. The crown jewel of the home is a newly upgraded, million-dollar backyard oasis. Including a 600 sq ft covered patio with a built-in kitchen with a Napoleon BBQ, a gas fireplace, a saltwater pool with spillover spa, a dedicated play area, and lush perennial gardens. Retreat to an 800 sq ft primary retreat, delivering privacy and true wow factor with vaulted ceilings, two-sided fireplace, wet bar, sitting area, boutique walk-in closet, and a spa-like ensuite featuring heated floors, a soaker tub, and a glass shower. The main floor is designed for both grand entertaining and everyday comfort with natural light pouring through oversized windows. Interior features include 10-foot ceilings, chevron-patterned wide plank hardwood, LED pot lights, built-in speakers, and designer chandeliers. The chef's kitchen is finished in dual-tone lacquered cabinetry with Caesarstone counters, premium Dacor appliances, a bright breakfast area, and a butlers server that connects to the sophisticated dining room. A sleek linear fireplace anchors the family room. The home office stands out with 15-foot cathedral ceilings, a fireplace, custom built-ins, and a walkout to the gardens. Above, you'll find three generously sized bedrooms, each with radiant heated ensuite baths and custom closets. Downstairs, the walk-up lower level is built to impress with a full wet bar, wine cellar, large rec room, two guest bedrooms, a gym with cushioned flooring, cedar infrared sauna, and a new two-tiered home theatre. Additional features include a Control4 smart home system, a two-car garage with car lift potential, and a location just minutes from top-rated public and private schools, lakefront parks, downtown Oakville, and QEW access for a seamless Toronto commute.

231 Wedgewood Drive, Oakville

1081 Argyle Drive, Oakville
$7,188,000
5 Beds ⋅ 7 Baths ⋅ W13776348 MLS
Crafted by the celebrated designer Gren Weis, this extraordinary estate stands as a testament to architectural brilliance, delivering more than 10,000 square feet of refined living across an expansive half-acre property in one of Oakville's premier lakeside enclaves. Every detail reflects master-level craftsmanship, highlighted by dramatic soaring ceilings, rich custom millwork, and an effortless layout designed to host grand gatherings or intimate family moments with equal grace. The main living areas transition smoothly into generously proportioned rooms filled with natural light. On the upper level, the home features private suites for all bedrooms, each accompanied by its own dedicated luxury ensuite bath. The lower level serves as an elite entertainment retreat, thoughtfully appointed with a climate-controlled wine cellar and a private cinematic theatre room that provides an immersive movie-going experience right at home. Outdoors, the resort-style grounds unfold into a breathtaking private sanctuary. Covered stone terraces provide space for year-round alfresco dining, complete with a fully equipped built-in outdoor kitchen and a resort-inspired luxury cabana. Meandering through the lushly planted mature gardens, a picturesque bridge crosses a natural stream, all beautifully illuminated in the evenings by custom accent landscape lighting. At the front of the property, a classic tier-inspired fountain and meticulous stonework set a commanding tone, bestowing the residence with an unmistakable and distinguished street presence on a prominent Oakville avenue. Located just moments from the region's highest-ranked public and private academies, this landmark residence seamlessly harmonizes timeless architectural prestige, modern everyday comfort, and sheer sophistication in an unrivaled setting. Luxury Certified

1081 Argyle Drive, Oakville

1113 Valleywood Court, Oakville
$2,369,000
4 Beds ⋅ 5 Baths ⋅ W13774528 MLS
Welcome to one of Glen Abbey's most coveted and rarely offered court locations. Nestled on a quiet family-friendly street and backing onto a mature ravine & wooded area, this exceptional home offers the perfect blend of privacy, space, and lifestyle. Set on an impressive nearly 10,000 sq ft pie lot, well above average for the area, this home offers approx. 3,500 sq ft AG plus over 1,500 sq ft of basement space. An open staircase connects all levels, while oversized windows fill the home with natural light and showcase beautiful views of the surrounding trees. Designed for family living and entertaining, the main floor features spacious principal rooms, a living room with hardwood floors & gas fireplace open to the dining room, and a welcoming family room with a second gas fireplace overlooking the backyard. The family-sized kitchen offers abundant workspace, stainless steel appliances, and a large eat-in area ideal for gathering with family and friends. Main floor laundry with inside access to the double garage adds convenience. Upper level offers four generous bedrooms & three full bathrooms, with all bedrooms enjoying ensuite access. The oversized primary retreat features a spacious sleeping area, sitting room or office space, walk-in closet & ensuite. Numerous renos completed in late 2023 include multiple bathrooms, hardwood flooring, and carpeting. The walk-up lower level is ideal for multigenerational living & features a recreation room with gas fireplace, wet bar, games area, and two flexible spaces for bedrooms, home offices, or a gym. Summer is unforgettable in the private backyard oasis featuring an inground pool, multiple entertaining areas, space for a hot tub, mature trees & spectacular ravine views. Lovingly maintained by one family, this is a rare opportunity to own an exceptional home in a premier Glen Abbey location close to top-rated schools, parks, trails, recreation, and all that Oakville has to offer. Photos from when home was previously staged.

1113 Valleywood Court, Oakville

16 Colonial Crescent, Oakville
$3,795,000
4 Beds ⋅ 4 Baths ⋅ W13774358 MLS
An exceptional opportunity on one of Southeast Oakville's most prestigious streets. Set on a nearly half-acre lot, 16 Colonial Crescent offers approximately 100 feet of frontage and more than 210 feet of depth, with outstanding proportions for a substantial custom build. The lot's generous dimensions and mature setting allow for an impressive new residence while maintaining exceptional privacy and meaningful outdoor space. Surrounded by mature trees and distinguished homes, the property offers a sense of scale and seclusion rarely found this close to the lake. RL1-0 zoning provides the potential for more than 6,000 square feet of above-grade living space, while still allowing for generous outdoor living, a pool and landscaped gardens, subject to applicable approvals. The property is currently a spacious four-bedroom residence offering approximately 3,700 square feet above grade, plus a finished lower level, attached double garage and inground pool-providing the flexibility to lease the home while planning a future build. Colonial Crescent is a quiet, established enclave known for its large properties, mature tree canopy, and impressive custom homes. Just steps from the lake and Gairloch Gardens, the location also offers convenient access to Downtown Oakville, excellent public and private schools, parks and the waterfront. A rare opportunity to secure a significant building lot on one of Southeast Oakville's premier streets and create an exceptional custom home in an highly sought-after location.

16 Colonial Crescent, Oakville

1305 Monks Passage, Oakville
$1,598,000
5 Beds ⋅ 4 Baths ⋅ W13760100 MLS
Welcome To 1305 Monks Passage Rd - A Stunning Executive Family Home Nestled On A Rare Corner Lot In The Heart Of Prestigious Glen Abbey, One Of Oakville's Most Sought-After Communities! Surrounded By Mature Trees With Beautiful Southwest Exposure, This Is The Private Backyard Retreat You've Been Waiting For! | KEY HIGHLIGHTS: 4 Bedrooms | 3.5 Bathrooms | Over 3,000 Sq Ft Of Total Finished Living Space | Rare Corner Lot With Exceptional Space & Openness | Quiet, Family-Friendly Street | Over $48K In Recent Upgrades! | OUTDOOR LIVING: Stunning saltwater inground pool perfect for summer enjoyment. Newly built backyard deck designed for entertaining and relaxation. Beautifully landscaped yard with mature trees offering exceptional privacy and seasonal blooms. A true backyard lifestyle property - ideal for family gatherings all season long! | INTERIOR FEATURES: Large principal rooms with excellent flow and abundant natural light. Main floor den/office - ideal for working from home. Bright kitchen with newer built-in cooktop, premium range hood & refrigerator. Generously sized bedrooms with flexible usage options. Renovated second-floor main bathroom. Upgraded basement offering additional living space. | RECENT UPGRADES: Renovated Main Bath ($20K) | Premium Kitchen Appliances & Range Hood ($12K) | New Backyard Deck ($5K) | Basement Upgrade ($5K) | Pool Heating System ($4K) | Roof Insulation Enhancement ($2K) | PRIME LOCATION: Walking distance to top-ranked Ontario schools. Minutes to Glen Abbey Golf Course, parks, trails, Oakville Hospital, shopping & community centres. Quick access to QEW & Hwy 403 for effortless commuting. | The Perfect Family Home Combining Luxury, Privacy & Unmatched Lifestyle In Glen Abbey. Don't Miss This Exceptional Opportunity!

1305 Monks Passage, Oakville

16 Ennisclare Drive W, Oakville
$10,950,000
5 Beds ⋅ 7 Baths ⋅ W13754954 MLS
Experience breathtaking, panoramic views from this stately lakefront estate, a true sanctuary of elegance and tranquility. Nestled on an expansive 3/4 acre lot, this rare gem boasts an impressive 100 feet of private lake frontage with riparian rights, ensuring unobstructed access to the shimmering waters of Lake Ontario. Spanning 5,800 sq. ft. (excluding the basement), this residence is designed for those who appreciate refined living and timeless sophistication. Step through the grand foyer into an atmosphere of classic luxury, where generous principal rooms flow effortlessly, highlighted by exquisite hardwood flooring and elegant finishes. Two stunning solariums maximize the lake's mesmerizing vistas, creating sun-drenched spaces perfect for relaxation and entertaining. The gourmet kitchen is a chef's dream, featuring a sprawling marble-topped island and an open layout designed for both functionality and style. Upstairs, five spacious bedrooms await, including the lavish primary suite, a private retreat with His & Hers walk-in closets and a spa-like 6pc ensuite bath. A versatile bonus room above the garage offers the perfect hideaway for a teen retreat, nanny suite, or home office. Outdoors, the beautifully landscaped backyard is an entertainer's paradise, complete with a sparkling inground pool, a picturesque patio, and the lake's serene backdrop enhancing every moment. A private gate leads directly to the lush surroundings of Gairloch Gardens, adding to the home's enchanting setting. Located in one of Oakville's most prestigious neighbourhoods, this exceptional property is just minutes from top-rated schools, fine dining, and the boutique shopping of Downtown Oakville. A rare opportunity to own a piece of lakeside luxury.

16 Ennisclare Drive W, Oakville

2031 DUNCAN Road, Oakville
$2,190,000
6 Beds ⋅ 3 Baths ⋅ W13751404 MLS
Gorgeous, recently updated bungaloft sits on an double-sized lot surrounded by mature trees in sought-after S.E. Oakville, offering outstanding privacy and potential to sever into two lots. Offering over 3,300 sqft. of finished living space, this spacious family home features a versatile layout with 2 bedrooms on the main level and 2 additional bedrooms upstairs, along with 2 full bathrooms. The recently renovated main floor showcases a bright and airy open-concept living and dining area, solid wood doors, and a skylight that fills the home with natural light. At the heart of the home is the upgraded kitchen, featuring a large granite centre island, premium stainless-steel appliances, and plenty of space for family gatherings and entertaining. The primary bedroom offers a beautifully renovated ensuite completed in 2025. The fully finished lower level provides excellent potential for a private in-law suite, complete with a separate entrance, 2 additional bedrooms, a full renovated bathroom, an expansive recreation room anchored by a cozy gas fireplace-ideal for extended family, guests, teenagers, or a private work-from-home retreat. Step outside to an impressive private backyard oasis, highlighted by a large in-ground saltwater pool and mature landscaping. An expanded front porch enhances the home's curb appeal, while the recently upgraded interlock front walkway with integrated landscape lighting creates an inviting entrance. The repaved driveway accommodates 6+ vehicles, providing exceptional convenience for a larger household. Enjoy an exceptional family-friendly location just a short walk to top-rated Oakville Trafalgar HS and Maple Grove PS, with the lake, parks, and convenient shopping just steps away. A unique combination of space, privacy, location and future potential-enjoy this beautifully updated family home today while holding a substantial oversized property in one of South East Oakville's most desirable neighbourhoods.

2031 DUNCAN Road, Oakville

1321 Monks Passage N/A, Oakville
$2,280,000
5 Beds ⋅ 4 Baths ⋅ W13742366 MLS
Luxurious and Renovated 5 Bedrooms + Main Floor Office 3.5 Baths in Prestigious Glen Abbey! This stunning Mattamy 'Yorkshire' model features 3,791 sqft plus an additional 1,200 sqft of finished basement space. Fully transformed and meticulously maintained gem in the top-ranked Abbey Park High School district. Gorgeous dark hardwood floors flow throughout the main and upper levels. smooth ceiling and pot lights thru out main floor. The beautifully renovated dream kitchen boasts solid maple cabinets, gas stove, quartz countertops, breakfast bar, walk-in pantry and chef's desk with with illuminated display cabinets. Gorgeous family room with bow window, wainscoting,limestone fronted fireplace. convenient office on main floor with double door entry. a grand Scarlett O'Hara staircase illuminated by a large skylight leads to the upper floor, where you'll find 5 bedrooms and 3 full bathrooms. The massive primary suite includes a renovated bathroom with a free-standing bathtub, frameless glass shower, double sinks, and a massive walk-in closet. An adjoining bedroom which is open to master bedroom offers flexible and convenient space as a nursery, media room, or second office. renovated Jack-and-Jill bathroom with 2nd skylight.The finished basement, featuring new vinyl flooring, is perfect for entertainment with dedicated game, media w/ gas fireplace and exercise rooms. over 530sf unfinished storage room for all your stuff. entire house is freshly painted. Escape to your private summer retreat, featuring a refreshing 18'x36' pool with new pool heater and pump(23) and a deep diving end, an interlocking patio, a charming muskoka rock garden, and fruit trees and bushes including Raspberry, Prune and Peach. **EXTRAS** freshly painted(24),bsmt vinyl flooring(24),renewed kit.(24),W/D(23), pool pump(23),pool heater(23),Attic insulation(22), flooring & three bathrooms (16), Windows14, Roof 12, Pool Rebuilt13, Furnace W Hepa Filter 00/10, Ac 05.

1321 Monks Passage N/A, Oakville

10 Brookfield Road, Oakville
$10,900,000
5 Beds ⋅ 4 Baths ⋅ W13738344 MLS
Situated on just over half an acre on the shores of Lake Ontario, 10 Brookfield Road is a truly exceptional waterfront property offering an extraordinary combination of views, privacy, recreation and year-round enjoyment. With unobstructed vistas of Lake Ontario from virtually every angle, the setting is as captivating as it is rare. The property's exceptional waterfront experience begins with riparian rights- the ultimate in waterfront living - and is highlighted by a detached boathouse with dedicated boat storage and a marine rail. Above, a spacious viewing deck and built-in gazebo create an ideal setting for entertaining, intimate gatherings, a lakeside bar or live music, all overlooking breathtaking panoramic views of the lake. Beyond the waterfront, an in-ground swimming pool and pool house with change rooms create a private, resort-like environment for summer entertaining and relaxed days at home. A parkette immediately to the east adds an exceptional sense of privacy, openness and seclusion rarely found in such a prominent waterfront setting. The natural topography creates distinct elevations and vantage points, allowing the home and outdoor spaces to fully embrace the lake. Inside, the spacious great room is designed for both everyday living and entertaining, complemented by an updated kitchen, walkout lower level and expansive windows that flood the home with natural light and showcase the views. Multiple walkouts provide seamless access to generous decks and outdoor entertaining spaces. Ideally located in close proximity to Lakeshore and Kerr Village, the property is also only a 15-minute walk to Downtown Oakville, offering convenient access to shops, restaurants, cafes and the vibrant village atmosphere. Whether enjoying a quiet morning overlooking the water, hosting friends poolside or launching a boat from the boathouse, 10 Brookfield Road is a truly rare waterfront offering. Luxury Certified.

10 Brookfield Road, Oakville

2372 Carrington Place, Oakville
$5,399,000
5 Beds ⋅ 5 Baths ⋅ W13729598 MLS
WATERFRONT PROPERTY! Experience the Potential of Lakeside Living. Perfectly situated on a premium 90' x 152' lakefront lot, this residence offers breathtaking, unobstructed water views from every principal room. With over 5,700 square feet of finished living space, the home presents an exceptional opportunity to bring your vision to a truly remarkable waterfront setting. The existing layout offers generous space for family living and entertaining, with rich hardwood flooring, limestone tiles, four skylights, two spacious family rooms, a private office, and a large kitchen with lake views! Upstairs, four generously sized bedrooms provide excellent space and privacy, while the primary suite showcases spectacular lake views. A convenient upper-level laundry room and walkout to the second-floor terrace offer additional potential to create a beautiful retreat overlooking the water. The fully finished lower level includes a fifth bedroom with a private ensuite, ideal for guests, extended family, or a nanny suite. Outdoors, the property offers an incredible foundation for creating your own waterfront oasis. The views, privacy, and ever-changing beauty of the waterfront truly have to be experienced to be fully appreciated, as the changing seasons, light, and skies create a new view from moment to moment. Additional highlights include a three-car garage, four fireplaces, an irrigation system, and ample storage throughout. This is a rare opportunity to transform an expansive waterfront property into a spectacular lakeside home, while enjoying the privacy, scale, and extraordinary setting that cannot be replicated. Luxury Certified.

2372 Carrington Place, Oakville

244 Willowridge Court, Oakville
$1,699,000
4 Beds ⋅ 3 Baths ⋅ W13721950 MLS
Welcome to 244 Willowridge Court, a lovingly maintained home nestled on a quiet dead-end court in sought-after Southwest Oakville, just moments from the lake, Coronation Park & Bronte Village. Set on an incredible pie-shaped -acre lot with over 100 feet across the rear and no backyard neighbours, this property offers an exceptional combination of privacy, space and outdoor living. This unique raised bungalow offers approximately 1,700 sq ft on the main level plus almost 1,600 sq ft on the lower level. Bright, oversized principal rooms feature large windows and hardwood floors throughout. The inviting living room showcases a wood-burning fireplace with stone hearth, while the dining room walks out to a deck overlooking the spectacular backyard. The spacious eat-in kitchen provides plenty of room for family and entertaining. Three bedrooms and three full baths include a generous primary suite with a large 4-piece ensuite featuring a soaker tub. The lower level is an incredible extension of the home, featuring a spacious recreation room with gas fireplace and large windows, plus a separate area ideal for extended or multi-generational family living. Complete with a second recreation room, 3-piece bath, English bar with seating and an additional bedroom, along with a convenient walk-up to the backyard. Step outside to your own private oasis with a large, full-depth inground pool, multiple entertaining areas, mature gardens and garden shed. With parking for 6+ vehicles and a double car garage with inside entry, there is plenty of room for family and guests. Lovingly cared for by the same family since 1989, this is a rare opportunity to live in and enjoy this home as it is, renovate and make it your own, or add on and create the home you've always envisioned. Ideally located close to excellent schools and highly regarded Appleby College, as well as the lake, parks, shops and restaurants of Bronte Village.

244 Willowridge Court, Oakville

15 Chartwell Road, Oakville
$9,995,000
5 Beds ⋅ 6 Baths ⋅ W13707486 MLS
15 Chartwell Rd offers a lifestyle of unparalleled luxury. Drive through the gates & discover the grandeur of this palatial estate. South of Lakeshore,1 door from the lake on a HALF ACRE LOT. Painstakingly curated, the contemporary limestone masterpiece you've been waiting for. Solid iron doors lead to a grand foyer revealing the opulent book matched marble floors. Floor to ceiling wdws & French doors flood the house with light. Cascading waterfalls fank the hall.The Dining Room has statement lighting & servery making hosting a breeze. Soaring 18-ft ceilings & a grand gas f/p are focal points of the Great Room,w/captivating views of the resort style yard. Experience culinary excellence in the black lacquer& glass kitchen by NEFF that features top of the line appliances & a B/I coffee machine & butlers pantry. The intimate Living Room with f/p is the ideal retreat. A main floor office w/built-in cabinetry.2 powder & 2 laundry rooms. The backyard oasis has a gunite pool, waterfalls, fire bowls, covered terrace & outdoor kitchen & f/p.The pool house has a change room,3-pc bath & servery. Towering trees surround the home & are positioned to create privacy. A stone driveway,circular fountain & lush gardens create a breathtaking landscape.Floating marble stairs divide the 3 levels of this home or, you can take the elevator. Skylights make the upstairs airy & bright.The principal suite has nearly 13-ft ceilings, an exquisite 6-piece ensuite & 2 W/I closets. A private balcony overlooks the yard.3 add'l bdrms have 10-ft ceilings,private ensuites & W/I closets. The LL caters to all family members. A 5th bdrm/ensuite makes an ideal guest suite.Gym,R/I Golf Simulator,home theatre,Wine Cellar& doggie Spa. The Games & Rec Rooms have a 2nd kitchen & W/O.Heated garage,baths &LL flrs.Automation. Designed by Bill Hicks & features the artistic creativity of the KT Design Group. Located on Oakville's Street of Dreams, this is an iconic living space designed to impress! LUXURY CERTIFIED

15 Chartwell Road, Oakville

579 Fourth Line, Oakville
$1,780,000
4 Beds ⋅ 4 Baths ⋅ W13701108 MLS
Completely renovated, top-to-bottom, inside and out. Set on a leafy residential street, this substantial brick home combines classic curb appeal with generous living space and a private backyard with swimming pool, newer fencing and extensive hardscaping.Inside, the home is bright, meticulous and well designed. New hardwood floors run throughout the main and upper levels, complemented by a contemporary staircase, replaced windows and renovated baths. The large eat-in kitchen is the heart of the home, with bright cabinetry, updated appliances and a generous island overlooking the backyardFormal front room, complete with gas fireplace, provides a quiet retreat or home office, while the family room, with fireplace and two skylights, offers another comfortable gathering space.Upstairs, the exceptionally large primary suite features a walk-in closet and renovated ensuite with double vanity. Two additional bedrooms are generously proportioned, each with double closets, making this a particularly functional home for a growing family.The finished lower level with wide plank hardwood adds considerable living space, with two separate recreation areas with gas fireplace, a private guest bedroom with ensuite bath and a stylish laundry room with loads of storage and raised washer/dryer. Outside, the property delivers the quintessential Oakville setting: a classic red-brick exterior, professionally landscaped grounds, a large double garage and driveway and a backyard designed for summer living around the pool.Surrounded by a mix of newer custom homes and established two-storey residences, this is a neighbourhood that continues to evolve while retaining its leafy, established character. Local schools are within an easy walk, and the location offers the appeal of being south; close to the lake and downtown amenities and a lifestyle that makes this part of Oakville so coveted.

579 Fourth Line, Oakville

46 Second Street, Oakville
$7,599,000
5 Beds ⋅ 7 Baths ⋅ W13694012 MLS
Walk to downtown Oakville from this 2024 custom-built residence, just three houses from Lake Ontario on a 65' x 158' lot south of Lakeshore. A rare new-construction opportunity in Old Oakville's most walkable pocket-minutes from the harbour, the Oakville Club, Lakeshore Road dining, and waterfront trails. Offers 4,362 sq. ft. above grade plus a 2,468 sq. ft. finished lower level (6,830 sq. ft. total). Net Zero Ready with a Tarion warranty, crafted by Chatsworth Fine Homes alongside architect John Willmott and designer Jane Lockhart. Main floor features herringbone white oak floors, panel mouldings, a private office, custom mudroom, and a formal dining room. The chef's kitchen boasts Miele appliances (plumbed coffee system, dual steam/standard ovens), SubZero refrigeration, and a wine column. It opens to a great room with a linear fireplace, custom built-ins, and floor-to-ceiling garden views. The primary suite serves as a spa-inspired retreat with a freestanding tub, oversized shower, double vanity, and a dressing-island walk-in closet. Secondary bedrooms each feature private ensuites. Includes heated floors, curbless showers, and upper-level laundry with two washer/dryer sets. The lower level (10' ceilings) is built to entertain: rec room with custom bar/kitchenette, gym, theatre, full bath, additional bedroom, and walk-up access to the yard. The west-facing rear yard catches optimal afternoon sun, complete with a covered heated lounge, in-ground pool with waterfall, and a hot tub. Extras include partial lake views, a heated driveway, radiant floor heating, Crestron automation, Tesla charger rough-in, and a standby generator. A turn-key luxury home in prime Old Oakville where inventory like this rarely comes to market. LUXURY CERTIFIED.

46 Second Street, Oakville

290 Duskywing Way, Oakville
$1,799,000
5 Beds ⋅ 5 Baths ⋅ W13691492 MLS
Welcome to 290 Duskywing Way, where bright, elegant family living meets a private backyard retreat in sought-after Lakeshore Woods. Beautifully positioned on a landscaped corner lot, this impressive 4-bedroom, 5-bathroom home benefits from additional windows and abundant natural light, creating a bright and airy feel throughout. Freshly painted and thoughtfully improved, it showcases extensive upgrades inside and out.The main level features soaring ceilings, upgraded hardwood flooring, California shutters, generous living and dining areas, and a spacious family room with fireplace-an inviting gathering place for family and friends. The kitchen offers abundant cabinetry, granite counters and centre island, with a convenient butler's servery connecting to the dining room. Main-floor laundry features a new washer and dryer. Upstairs, four generous bedrooms include a spacious primary retreat with walk-in closet and ensuite. A rare highlight is 3 bathrooms on the second level, including a Jack & Jill connecting two bedrooms. The professionally finished lower level offers an expansive recreation and billiards area, wet bar, gym, bathroom and private office that could serve as an additional bedroom, with excellent potential for extended-family or in-law living. Outside, enjoy a private, maturely landscaped backyard featuring a recently maintained in-ground pool with brand-new liner, gazebo, extensive hardscaping and inviting spaces for dining, lounging and entertaining. A large, recently sealed exposed aggregate concrete driveway complements the upgraded garage with new epoxy flooring and built-in cabinetry. Further improvements include newer furnace & A/C, owned hot water tank, central vacuum and irrigation system. Ideally located in a welcoming, family-friendly neighbourhood near Lake Ontario, Bronte Harbour, parks, trails, schools, shopping, dining and highways. A beautifully cared-for Lakeshore Woods home reflecting pride of ownership throughout.

290 Duskywing Way, Oakville

235 LAKEWOOD Drive, Oakville
$4,390,000
5 Beds ⋅ 5 Baths ⋅ W13673302 MLS
Located in coveted West Harbour, come discover tranquility and elegance at 235 Lakewood Drive. Nestled on a generous .56-acre lot, embraced by majestic foliage in a private cul-de-sac, this residence epitomizes serene living mere steps from the lake. Crafted by renowned architect Gren Weis, the fusion of stone and wood siding spans over 6,200 square feet. Step into the foyer with its soaring cathedral ceilings, offering glimpses of the expansive living spaces beyond. Designed for seamless flow, this sophisticated layout effortlessly accommodates both grand and intimate gatherings. A bespoke oak staircase adorned with shimmering Schonbek chandeliers leads to the upper levels, where solid oak hardwood flooring graces much of the home. The living room boasts exquisite millwork, custom fireplace, and state-of-the-art entertainment amenities by Canadian Sound Ltd. The gourmet kitchen, recently reimagined, features top-tier appliances, quartz countertops, and abundant storage, with access to a sprawling composite, low maintenance deck. A stately maple wood-paneled study overlooks manicured gardens, providing a serene retreat. Five generous bedrooms, each with an ensuite and ample closets, offer luxurious comfort. The primary suite is a haven of indulgence, flaunting dual walk-in closets, spa-like ensuite with airy vaulted ceilings, skylights, and deluxe fixtures. The lower level is all about leisure and function, boasting a custom-painted wood-paneled rec room with lakeside vibes, alongside a gym, wine cellar, and top-notch utility room. Outside, the meticulously landscaped grounds offer a saltwater pool with waterfall, a spa, and outdoor entertainment system, perfect for alfresco movie nights. This home boasts a brand new roof with lifetime warranty! Stroll to lovely downtown Oakville, trendy Kerr Village, Tannery Park along the Lake & waterfront trails. Close proximity to highly esteemed schools.

235 LAKEWOOD Drive, Oakville

2076 GLENFOREST Crescent, Oakville
$3,590,000
5 Beds ⋅ 4 Baths ⋅ W13669660 MLS
Spectacular 2/3-acre premium lot in South East Oakville's highly coveted private crescent. Thoughtfully designed for both refined family living and multi-generational flexibility, this beautifully renovated residence blends contemporary architecture, sophisticated finishes, and an impressive resort-style setting. At the heart of the home is the sleek Top Notch kitchen, featuring high-gloss white cabinetry, marble backsplash, an oversized 12+ feet long white Caesarstone central island, and premium appliances. The elegant living room is anchored by a linear fireplace and striking glass-enclosed wine cellar, creating a sophisticated setting for entertaining. The luxurious primary suite features a spa-inspired ensuite with heated floors, floating contemporary cabinetry, and a walk-in glass shower. Heated flooring extends through all bathrooms, the mudroom, and laundry room, adding comfort and quality throughout. A rare highlight is the fully self-contained 2-bedroom in-law suite, complete with a separate entrance, private kitchen, laundry, and bathroom-ideal for extended family, guests, or live-in support. The main residence is filled with natural light, including a stunning glass-enclosed breakfast area that overlooks the expansive grounds. Outside, the extraordinary grounds offer a true private retreat with an in-ground saltwater pool, hot tub, mini-golf area, mature landscaping, and exceptional privacy. Fully renovated to create a fresh, airy, contemporary feel, this one-of-a-kind home also enjoys a functional family-friendly layout and is within walking distance to some of Oakville's top-rated schools. A rare opportunity to own a truly distinctive residence on one of South East Oakville's most coveted large estate lots.

2076 GLENFOREST Crescent, Oakville

244 Colchester Drive, Oakville
$3,088,888
6 Beds ⋅ 5 Baths ⋅ W13658672 MLS
Welcome to this bright and well-maintained home with 5-bedroom, 5-bathroom and over 4,600sf living space on a 100x151.76ft premium lot in Oakville's prestigious Eastlake community. Set on a quiet, tree-lined street surrounded by mature trees, just steps to top-ranked schools (Oakville Trafalgar High School and Maple Grove Public School)The functional main floor features formal living and dining rooms, a private office, and an open-concept kitchen, spacious breakfast area and family room with a fireplace overlooking the backyard. Multiple windows and skylights fill the space with natural light, while multiple walkouts lead to the covered porch, professionally landscaped backyard and inground pool. The kitchen features a large centre island and was refreshed in 2026 with new countertops, refrigerator, stove and range hood.Interior doors and door frames on the main and second floors were also replaced in 2026. A mudroom, laundry room and powder room complete the main level.The second floor offers a practical and well-designed layout with five bright, generously sized bedrooms and three bathrooms, including a spacious primary suite with a private ensuite and walk-in closet. The thoughtful arrangement provides excellent comfort and functionality for family living.The finished walk-up basement with a separate entrance offers exceptional flexibility and is divided into two distinct living areas. One side features a spacious recreation room with a fireplace and wet bar, while the other includes a second kitchen, bedroom, three-piece bathroom, separate laundry and direct access to the backyard. With two kitchens, two laundry areas and a flexible layout, the home is ideal for a large or multigenerational family, with excellent potential for extended family or secondary living arrangements.Additional updates include the roof in 2018 and furnace in 2025. A rare opportunity combining space, functionality, location, a premium lot and outstanding future potential. Must to see!

244 Colchester Drive, Oakville

379 River Side Drive, Oakville
$2,999,000
4 Beds ⋅ 4 Baths ⋅ W13647310 MLS
Welcome to this exceptional custom-built bungaloft, thoughtfully owner-designed and completed in 2010, where timeless craftsmanship, luxurious finishes, and an unparalleled setting backing onto Sixteen Mile Creek come together to create a truly one-of-a-kind home. Offering 3 spacious bedrooms and a highly desirable main floor primary suite, this residence has been meticulously designed with no detail overlooked. The primary retreat features a luxurious 6-piece ensuite and a walkout to a private backyard oasis, creating the perfect space to begin and end each day. The heart of the home is the stunning custom kitchen, complete with soapstone countertops, a large centre island, built-in bench seating for relaxed family breakfasts, custom cabinetry with abundant storage, elegant chandeliers, and premium finishes throughout. The kitchen flows seamlessly into the impressive family room, highlighted by soaring vaulted ceilings open to the second level, creating an inviting space for everyday living and entertaining. A walkout leads to the expansive deck overlooking the beautifully landscaped backyard and saltwater pool. Exquisite architectural details, including wrought iron railings throughout, custom millwork, and quality craftsmanship, elevate every room. Main floor laundry adds everyday convenience. The fully finished lower level is designed for entertaining and relaxation, featuring a spacious recreation room overlooked by a full wet bar, games room, exercise room, and a spa-inspired 5-piece bathroom, offering the perfect extension of the home's living space. Backing onto the natural beauty of Sixteen Mile Creek, this remarkable property provides exceptional privacy, scenic views, and a tranquil setting rarely found. Move in, relax, and enjoy luxury living with nothing left to do but unpack.

379 River Side Drive, Oakville

1472 Oakhill Drive, Oakville
$7,998,000
5 Beds ⋅ 6 Baths ⋅ W13643716 MLS
Welcome to 1472 Oakhill Drive, a newly built contemporary residence in the heart of prestigious South East Oakville, where timeless sophistication meets exceptional craftsmanship. Offering nearly 7,800 sq.ft. of exquisitely finished living space across three levels, this custom designed home delivers an elevated lifestyle defined by refined architecture, luxurious finishes and effortless indoor-outdoor living. A striking façade with a metal roof, heated driveway and walkways, professional landscaping and a triple tandem garage creates an unforgettable first impression. Inside, soaring 10-foot ceilings, a dramatic two-storey foyer, solid mahogany entry door and bespoke millwork throughout set the tone for the home's impeccable attention to detail. Designed for both elegant entertaining and everyday living, the open concept main floor features a stunning chef's kitchen appointed with premium Gaggenau integrated appliances, custom cabinetry, and seamless access to the spectacular outdoor living spaces. The covered rear porch is a true extension of the home, complete with automated retractable screens, a built-in outdoor kitchen, cedar tongue-and-groove ceiling and generous lounge and dining areas. The resort inspired backyard is centred around a 14' x 34' saltwater Gunite pool with an integrated hot tub, waterfall feature and a custom cabana. The second level offers four spacious bedrooms, each with a private ensuite and custom closet solutions, creating a luxurious retreat for every family member. The finished lower level adds exceptional versatility with a fifth bedroom, a full bathroom, and expansive recreation and entertainment space. Set on one of South East Oakville's most desirable streets, this exceptional residence combines modern design, superior construction, and resort-calibre amenities in a location renowned for its top-ranked schools, lakefront parks, and proximity to downtown Oakville. A rare opportunity to own a truly distinguished custom home.

1472 Oakhill Drive, Oakville

2380 Gladacres Lane, Oakville
$1,937,777
4 Beds ⋅ 5 Baths ⋅ W13638086 MLS
Welcome to this exceptional detached home in Oakville's sought-after Westmount neighbourhood, offering just over 5000 sq. ft. of beautifully appointed total living space including a fully finished walk-out basement. Situated on a 162' deep premium private pie-shaped lot, this impressive home combines spacious interiors with an incredible backyard retreat featuring a sparkling pool-perfect for entertaining, relaxing and enjoying summer days with family and friends. The main level is thoughtfully designed with a spacious and versatile layout, offering a separate living room, dining room, family room and dedicated office, providing plenty of space for both everyday family life and formal entertaining. The recently renovated kitchen serves as the heart of the home, offering a fresh, modern design with excellent functionality and seamless connection to principal living spaces. Upstairs, you'll find four spacious bedrooms with five walk-in closets and three full bathrooms, offering exceptional comfort and convenience. The primary bedroom is a private retreat, featuring a generous seating area and an updated ensuite bathroom. The fully finished basement provides additional living space and additional full bathroom, ideal for family gatherings or in-law suite. Step outside to your own private oasis. The premium private pie-shaped lot and inviting pool create an exceptional setting for summer entertaining and outdoor enjoyment, while the irrigation system makes maintaining the grounds effortless. Ideally located close to excellent schools, parks, trails, Oakville Hospital, shopping and much more.

2380 Gladacres Lane, Oakville

1387 Ferncrest Road, Oakville
$2,399,000
6 Beds ⋅ 6 Baths ⋅ W13624230 MLS
5 Elite Picks! Discover 5 Reasons To Make This Home Your Own: 1. Spectacular Private Backyard Oasis with Heated Salt Water Pool, Expansive Multi-Tier Patio Area, Mature Trees & Lovely Gardens. 2. Spacious Kitchen Featuring Large Centre Island with Breakfast Bar, Granite Countertops, Stainless Steel Appliances & Bright Breakfast Area with Ample Large Windows & W/O to Patio, Pool & Backyard! 3. Spacious Principal Rooms Including Stunning Family Room with Custom Coffered Ceiling, Gas Fireplace & Large Windows Overlooking the Backyard, Combined Open Concept Dining Room & Living Room with Crown Moulding & Large Windows, and Private Office with Garden Door W/O to Patio! 4. Spacious 2nd Level with Upgraded Hdwd Flooring ('24) Offering 4 Bedrooms, 3 Updated Baths ('24) & W/I Linen Closet, with Oversized Primary Suite Featuring Huge W/I Closet + 2nd Closet & Luxurious 5pc Ensuite with His & Hers Vanities, Jacuzzi Tub & Large Glass-Enclosed Shower. 5. Bright & Airy Finished Basement with Laminate Flooring Boasting 2nd Kitchen with Centre Island, Ample Cabinetry & Granite Countertops, Generous Rec Room with B/I Shelving/Entertainment Unit with Electric Fireplace, 2 Additional Bedrooms (2nd Bdrm with Semi-Ensuite Access to 4pc Bath/No Closet), 2pc Powder Room, 2nd Laundry & Abundant Storage. All This & More! 2pc Powder Room, Convenient Main Floor Laundry & Mud Room Area with Garage Access Complete the Main Level. Spacious 2nd Bedroom Boasts W/I Closet & Private 3pc Ensuite, and Good-Sized 3rd & 4th Bedrooms Share Access to 3pc Semi-Ensuite. Fabulous Space with 3,767 Sq.Ft. A/G Plus Finished Basement. Stunning Curb Appeal with Stone Driveway & Steps Leading to Lovely Covered Porch with Double Door Entry to Elegant Foyer (Updated Flooring '24). Updated Shingles '23, New Furnace & A/C '22. Fantastic Location in Prestigious Joshua Creek, Just Minutes to Top-Rated Schools, Parks & Trails, Shopping, Restaurants & Quick Hwy Access!

1387 Ferncrest Road, Oakville

2149 Alderbrook Drive, Oakville
$2,599,999
4 Beds ⋅ 5 Baths ⋅ W13622864 MLS
Welcome to 2149 Alderbrook Drive, an exceptional National Homes residence built in 2003 and proudly offered for sale by its original owners. Located in Oakville's highly sought after Westmount community, this beautifully maintained family home sits on a premium interior corner lot and offers approximately 3,350 sq. ft. above grade, plus a professionally finished basement. The home features 4 spacious bedrooms and 5 bathrooms, the home blends timeless design with outstanding functionality. The main level showcases hardwood flooring throughout the principal living areas, formal living and dining rooms, a spacious family room with gas fireplace, main-floor laundry. A beautifully appointed kitchen with natural stone flooring, quartz countertops, stainless steel appliances, 36'' Wolf gas stove, built in electric oven & microwave, center island, and abundant cabinetry. Upstairs, the primary retreat features a custom walk-in closet and luxurious 5-piece ensuite. A dedicated office provides an ideal work from home space, while 2 secondary bedrooms share a well designed bathroom with double vanities. The finished basement is designed for entertaining, complete with a custom floating media wall, wet bar with sink, wine cooler, glass-enclosed wine display, full 5-piece bathroom, and generous recreation area. Step outside to a private backyard oasis featuring a heated saltwater pool with a new liner, extensive concrete hardscaping, and storage shed. Additional highlights include a lifetime metal roof, double-car garage, and oversized driveway accommodating up to 7 vehicles. Ideally located within walking distance of schools, parks, and trails, and only minutes from Oakville Trafalgar Memorial Hospital, shopping, restaurants, transit, and major highways, and the Glen Abbey Golf Club, this exceptional home offers space, comfort, and lifestyle in one of Oakville's premier family neighbourhood's.

2149 Alderbrook Drive, Oakville

215 Burloak Drive, Oakville
$1,999,999
6 Beds ⋅ 5 Baths ⋅ W13617880 MLS
Imagine never needing a cottage again. Welcome to one of Lakeshore Woods' most exceptional properties, where luxury living meets the tranquility of a private Muskoka-inspired retreat. Set on a spectacular 50 x 180 ft lot backing onto protected greenspace, this remarkable home offers nearly 3,000 sq. ft. above grade, plus 1,280 sq. ft. of beautifully finished lower-level living space. Designed for both everyday living and effortless entertaining, the resort-style backyard is the true showpiece, featuring a saltwater pool with a stone waterfall, gazebo, cabana, professionally landscaped gardens, and complete privacy surrounded by mature trees. Inside, timeless elegance meets modern comfort with rich hardwood floors, a natural oak staircase, soaring 18-foot cathedral ceilings, and an abundance of natural light. The gourmet kitchen flows seamlessly into the breakfast area and opens directly to the backyard, while the inviting family room with a gas fireplace creates the perfect gathering space. Upstairs, you'll find four spacious bedrooms, including a luxurious primary retreat with a spa-inspired ensuite and custom walk-in closet. The fully finished lower level adds incredible versatility with two additional bedrooms, a brand-new three-piece bathroom, rough-in for a future kitchen, and potential for a separate walk-up-ideal for extended family or multi-generational living. Complete with parking for up to eight or nine vehicles and located just minutes from Lake Ontario, scenic trails, hidden beaches, top-rated schools, shopping, the GO Station, and major highways, this is more than a home-it's a lifestyle.

215 Burloak Drive, Oakville

2442 Woburn Crescent, Oakville
$1,628,000
3 Beds ⋅ 3 Baths ⋅ W13591306 MLS
Welcome to this beautifully renovated 4-level side-split detached, offering approximately 2000 sq.ft. of finished living space. Ideally situated on a premium pie-shaped lot and a quiet crescent. Featuring a spectacular resort-style backyard in one of Oakville's most desirable neighbourhoods. Boasting 3 spacious bedrooms and 3 bathrooms, including two fully renovated spa-inspired baths with heated floors, heated smart toilets, jet showers, illuminated vanity mirrors, and electric blinds, every detail has been thoughtfully designed.The stunning chef's kitchen is the heart of the home, showcasing quartz countertops, a large centre island, Bosch stainless steel appliances, built-in wine cooler, double sink with garburator and sleek custom cabinetry with abundant storage. The inviting living room with fireplace and bright dining area overlook the beautifully landscaped backyard. Step outside to your private oasis with a heated saltwater in-ground pool, newly stained deck, contemporary gas fire pit, lush landscaped gardens and no rear neighbours-backing onto open green space for exceptional privacy.The newly renovated basement features a spacious recreation room with a stylish wet bar, built-in Bosch microwave, gas fireplace, large windows, modern laminate flooring, upgraded laundry room with new sink and washer and dryer. Two crawl spaces with new laminate flooring provide ample storage. Major Updates: 2 Bathrooms & Basement (2026), Kitchen, Bosch Appliances, Laundry Room, Paint & Entryway Flooring (2025), Roof , Garage Doors (2025), Pool Filter & Heater, Furnace & A/C (Rental 2022). Ideally located just minutes from Oakville's waterfront, Bronte GO Station, Downtown Oakville, top-rated schools, parks, trails, community centres, shopping, and restaurants. Note: the garage doors in the pictures have been replaced with new doors.

2442 Woburn Crescent, Oakville

1102 Crestview Street, Oakville
$6,250,000
5 Beds ⋅ 7 Baths ⋅ W13558096 MLS
This is not your average home-it's a statement.Set on a premium, near half-acre lot, this custom masterpiece brings together the vision of Gren Weis, the craftsmanship of Bachly Construction, and the landscape artistry of Mark Pettes-creating a residence that feels as elevated as it is effortless.From the moment you step inside, the energy shifts. Soaring 10-ft ceilings and a stunning 17-ft sun-drenched family room set the tone-open, airy, and designed to impress. A dedicated main floor office offers the perfect balance of productivity and privacy, ideal for today's work-from-home lifestyle. Whether it's an intimate night in or a full house of guests, the flow is seamless. A prep kitchen keeps everything behind the scenes running smoothly, while the newly added main-floor bar invites you to pour a drink and stay awhile. The glass-encased wine room? Pure drama-in the best way.Every bedroom is its own private retreat, complete with a luxe ensuite-because comfort should never be compromised.Downstairs, the vibe continues. Think late nights at the wet bar, morning workouts in your private gym, spa-level relaxation, and a fully equipped nanny suite. A walk-out lower level leads directly to the hot tub-blurring the line between indoor comfort and outdoor indulgence. This level isn't just extra space, it's a lifestyle.And then there's the backyard. Tiered, curated, and designed to be lived in. A newly added pool sets the scene, while the covered cabana lounge and outdoor kitchen make entertaining feel like a vacation. There's even a dedicated dog run-because every detail has been considered.Sleek, bold, and undeniably fun-this is a home that doesn't just look good, it lives beautifully.

1102 Crestview Street, Oakville

1179 Carey Road, Oakville
$3,450,000
5 Beds ⋅ 5 Baths ⋅ W13548392 MLS
Exceptional contemporary family home on a premium 87x 179 southwest lot on one of Southeast Oakville's most sought-after streets, just steps to top-ranked public schools and prestigious private schools including Linbrook School & St. Mildred's-Lightbourn School. Offering over 5,000 sq. ft. of beautifully finished living space, this impressive residence offers modern design and exceptional family functionality. A generous foyer creates a stunning first impression, with sightlines extending through the home to the beautifully landscaped rear gardens. Professionally designed outdoor living features extensive hardscaping, an inground pool, hot tub, covered gazebo, fire pit zone, and landscape lighting, creating a private resort-like setting for entertaining and family enjoyment. The thoughtfully designed layout offers 4+2 bedrooms and 3+2 bathrooms. All bedrooms feature built-in closets, while the primary generous suite boasts dual walk-in closets and a spa-inspired ensuite with double vanity, soaker tub, and separate shower. The heart of the home is a stunning contemporary kitchen overlooking the spacious family room with a gas fireplace and wall of sliding glass doors opening to the private backyard oasis. Elegant principal rooms include a formal living room with fireplace and oversized windows, a separate dining room, a dedicated main floor office, and a well-appointed mudroom with inside access to the attached two-car garage.The fully finished lower level includes a spacious rec room with gas fireplace, adjoining billiards area, two additional bedrooms, a sauna, laundry room with second refrigerator, direct access to the side yard-ideal for guests, extended family, or recreation. Nestled on one of Southeast Oakville's most desirable streets, this exceptional property offers the charm and tranquility of an established neighbourhood with mature trees, beautiful parks, and convenient access to lakeside parks and Downtown Oakville.

1179 Carey Road, Oakville

127 Mayfield Drive N, Oakville
$1,289,990
4 Beds ⋅ 2 Baths ⋅ W13545806 MLS
Exceptional opportunity in the highly sought-after College Park community of Oakville! Welcome to 127 Mayfield Drive, a well-maintained, move-in-ready bungalow offering 4 spacious bedrooms, 2 full washrooms, a bright living room with fireplace, a generous dining area, and an expansive kitchen-perfect for families, investors, or builders alike. The home has just become vacant and was previously generating $4,200 per month in rental income, making it an excellent investment opportunity with immediate income potential if leased again.Situated on a premium lot, the property features parking for up to 8 vehicles, including a 6-car driveway and a 2-car attached garage. The backyard offers a full-size 16 ft x 32 ft in-ground swimming pool, creating a fantastic outdoor entertaining space. The pool is fully in place and functional but requires routine maintenance and a new liner, presenting a great opportunity for the next owner to restore it to its full potential. For builders and developers, this property comes with approved permits to construct approximately 3,400 sq. ft. above grade (approximately 5,200 sq. ft. including the basement), allowing you to build a spectacular luxury custom home in a neighbourhood surrounded by newly built multi-million-dollar residences. Ideally located just 7 minutes from Lakeshore Road, 2 minutes from the golf course, and 5 minutes from Downtown Oakville, with easy access to top-rated schools, parks, shopping, restaurants, transit, and all major amenities.Whether you're looking for a move-in-ready home, a strong investment property, or the perfect lot to build your dream custom residence, 127 Mayfield Drive presents a rare opportunity in one of Oakville's fastest-transforming luxury neighbourhoods.

127 Mayfield Drive N, Oakville

104 Whittington Place, Oakville
$2,599,999
5 Beds ⋅ 4 Baths ⋅ W13528872 MLS
Perfectly positioned in one of Southwest Oakville's most sought-after neighbourhoods, directly across from the prestigious Appleby College, this exceptional family residence offers over 5,000 square feet across all levels, blending timeless elegance with outstanding functionality. Thoughtfully designed for both everyday living and entertaining, the main level showcases expansive principal rooms filled with natural light. The chef-inspired kitchen is the heart of the home, featuring custom cabinetry, granite countertops, a large centre island, quality appliances, and an adjoining breakfast area overlooking the private backyard. The inviting family room offers seamless access to the outdoor living spaces, while the formal living and dining rooms provide refined spaces for hosting family gatherings and special occasions. A handsome wood-paneled home office creates the perfect work-from-home environment. Upstairs, the home offers 3 spacious bedrooms, highlighted by a luxurious primary retreat complete with a generous walk-in dressing room and spa-inspired ensuite with heated floors. The additional bedrooms are well-proportioned and ideal for family or guests. The finished lower level extends the living space with 2 additional bedrooms, a large recreation/media room, a custom wine cellar, ample storage, and flexible space perfect for extended family, teenagers, or a home gym. Set on a private, mature lot, the backyard features an in-ground pool, hot tub and exceptional privacy, creating the perfect setting for summer entertaining. Ideally located just moments from the lake, parks, downtown Oakville, and top-rated schools, this is an outstanding opportunity to own a distinguished family home in one of Oakville's most coveted neighbourhoods.

104 Whittington Place, Oakville

2330 Valleyridge Drive, Oakville
$1,698,000
4 Beds ⋅ 5 Baths ⋅ W13520576 MLS
Welcome to 2330 Valleyridge Drive, an exceptional move-in ready family home offering 4 bedrooms, 5 bathrooms, and 3,937 sf of finished living space in one of Oakville's most sought-after communities. Deceptively spacious & much larger than it appears, this impressive property backs onto a private ravine and features a saltwater inground pool, professionally landscaped grounds, and a backyard retreat surrounded by mature cedar trees. A 1.5-car garage with inside entry and parking for 4 cars completes the property. Ideally located close to top-rated schools, parks, walking trails, shopping & everyday amenities. Hardwood flooring extends throughout the principal rooms. The living room features 9' ceilings, a gas fireplace, and built-in surround sound. The family room flows seamlessly into the breakfast area and eat-in kitchen featuring granite countertops, custom cabinetry with soft-close drawers, pot and pan drawers, under-cabinet lighting, stainless steel appliances, pot lights, and a walkout to the backyard. A 2pc powder room completes the main level. The upper level offers four generous bedrooms, including a private primary retreat with a walk-in closet and 5pc ensuite featuring double sinks, a freestanding soaker tub, glass-enclosed shower, and separate water closet. Two additional 4pc bathrooms and upper-level laundry complete this floor. The finished lower level adds exceptional living space with a large recreation room, 3pc bathroom, and abundant storage. Outside, the private backyard showcases a saltwater pool, new deck (2025), mature cedar trees, and a peaceful ravine setting, creating an exceptional space for outdoor entertaining and relaxation. Combining generous living space, a functional family layout, move-in ready (newer roof, furnace, pool heater & pump) convenience, and an exceptional ravine setting, this Oakville home presents an outstanding opportunity in a highly sought-after neighbourhood.

2330 Valleyridge Drive, Oakville

153 Cairncroft Road, Oakville
$3,890,000
4 Beds ⋅ 5 Baths ⋅ W13512502 MLS
Nestled on an exceptional 15,511sqft mature lot in prestigious Southeast Oakville, this beautifully renovated executive residence offers timeless elegance, luxurious finishes, and an unbeatable location within walking distance to top-ranked schools, including OTHS, EJ PS etc. Offering approximately 3487 sqft. above grade plus a finished lower level, this exceptional home features 4 bedrooms, 5 bathrooms, and thoughtfully designed living spaces perfect for both family living and entertaining.Rich wide-plank hardwood floors, crown mouldings, custom millwork, wainscoting, built-ins, pot lights, stone flooring, an impressive oak staircase with iron pickets, and four gas fireplaces showcase the home's exceptional craftsmanship. The stunning renovated chef's kitchen is appointed with premium Miele appliances, custom cabinetry, and overlooks the inviting sunken family room, creating the perfect gathering space. Elegant formal living and dining rooms provide refined spaces for entertaining, with the living room easily accommodating a baby grand piano.The luxurious primary retreat features its own gas fireplace, an expansive dressing room, and a spa-inspired 4-piece ensuite with a glass shower. The finished lower level offers a spacious recreation room, exercise room, 2-piece bath, and abundant storage.Extensive updates include a complete kitchen renovation, premium Miele appliances, exterior LED lighting, renovated garage, repaved driveway, new eavestroughs, freshly painted exterior façade, new pool liner and heater, and numerous quality improvements throughout.The spectacular backyard is a private oasis featuring a sprawling stone patio, covered terrace, and sparkling in-ground pool surrounded by mature landscaping-perfect for summer entertaining. Ideally located just steps to Lake Ontario, Gairloch Gardens, parks, trails, and only a 3-minute drive to downtown Oakville's boutique shops, fine dining, and waterfront.

153 Cairncroft Road, Oakville

2212 Urwin Crescent, Oakville
$1,799,000
5 Beds ⋅ 5 Baths ⋅ W13505840 MLS
RECENTLY REIMAGINED FOR MODERN FAMILY LIVING WITH A RESORT-STYLE BACKYARD IN SOUGHT-AFTER WEST OAKVILLE! JUST MINUTES TO THE LAKE! This exceptional residence offers 4+1 bedrooms, 4.5 bathrooms, and a professionally finished lower level, seamlessly blending sophisticated design with everyday functionality. The open concept main level is enhanced by engineered hardwood flooring, expansive floor-to-ceiling windows, and light-filled principal rooms designed for everyday living and entertaining. The stunning custom kitchen features quartz countertops, oversized centre island with sink, JennAir gas range, pot filler, and access to the backyard. An open-riser staircase with glass panels creates a striking architectural focal point, while the living room is anchored by a dramatic feature wall with gas fireplace. Upstairs, engineered hardwood continues throughout. The primary retreat showcases a designer accent wall, elegant wall sconces, a walk-in closet with window and custom built-ins, and a spa-inspired five-piece ensuite with freestanding tub, glass shower with rainfall showerhead, and double vanity. A second bedroom features its own private three-piece ensuite, while two additional bedrooms share a beautifully appointed four-piece bathroom. A laundry room with sink completes the upper level. The backyard is a private oasis designed for entertaining and relaxation, featuring an inground pool with an eco-friendly, cost-effective copper ionizer system, extensive stone hardscaping, and a covered outdoor living area with gas fireplace. A dedicated BBQ station with natural gas line and convenient side-door access to the kitchen further enhances the outdoor experience. Ideally located close to parks, top-rated schools, Queen Elizabeth Park Community and Cultural Centre, shopping, transit, major highways, and the lake. This remarkable home offers an exceptional lifestyle in a coveted family-friendly neighbourhood. (certain exterior images have been digitally enhanced)

2212 Urwin Crescent, Oakville

2054 Lakeshore Road E, Oakville
$33,000,000
7 Beds ⋅ 13 Baths ⋅ W13453124 MLS
2054 Lakeshore Rd. East is one of Oakville's finest lakefront estates.Situated on 1.6 acres & 166 ft of pristine shoreline, complete with deck & stairway access to the water. Designed by renowned architect Gren Weis & brought to life by the exceptional craftsmanship of Coulson Fine Homes.This magnificent 7-bdrm, 13-bath home spans an impressive 19,210 sq ft living space.Step into the grand formal entrance where limestone cast walls create a dramatic first impression serving as a prelude to the extraordinary spaces beyond.The residence showcases 12 ft ceilings on the main level, Brazilian walnut flooring thru-out & custom cabinetry adorns this remarkable home.The estate features an expansive living & dining rm w/breathtaking water views, perfect for intimate gatherings or grand celebrations.Step outside to the covered terrace where you can relax to the sounds of the "Bellagio" inspired fountains & waterfall.The gourmet open-concept kit.flows effortlessly into the fam.rm where water views & fp create a relaxed & comfortable space.The lower-level transforms into an entertainer's paradise, w/a state-of-the-art home theater, gym w/direct access to the infinity edge pool,steam room, golf simulator, wine cellar, billiards area w/rec room & catering kit.A private 2-bdrm nanny suite w/sep. entrance. Two laundry rooms .An elevator gives you convenient access to all 5 levels of this thoughtfully designed home.The outdoors offers multiple entertaining areas nestled within the manicured landscaped grounds, the lakefront deck & poolside.The power screened sunroom offers 3 season enjoyment.His & Hers double car garages to accommodate 4 vehicles w/additional parking for 20 more on the circular driveway & auxiliary prkng areas-perfect for hosting memorable events.This waterfront estate represents more than just a home it's a lifestyle statement and every detail is curated to create an environment of uncompromising luxury and comfort. LUXURY CERTIFIED.

2054 Lakeshore Road E, Oakville

262 Maple Grove Drive, Oakville
$10,880,000
5 Beds ⋅ 7 Baths ⋅ W13448452 MLS
Set on one of Morrison's most coveted streets, this extraordinary custom-built estate offers over 10,800 sq ft of impeccably designed living space, complemented by a remarkable 3,400 sq ft two-level garage and showroom with accommodation for up to 10 vehicles. A striking stone façade introduces interiors defined by exceptional craftsmanship, soaring ceilings, expansive principal rooms, and walls of glass that seamlessly connect to the resort-inspired grounds. Designed for both grand-scale entertaining and refined family living, the main level features elegant formal living and dining rooms, a private executive office, and a spectacular chef's kitchen with bespoke cabinetry, premium appliances, an oversized island, walk-in pantry, and full servery. The adjoining family room and Muskoka-inspired lounge create an effortless indoor-outdoor lifestyle experience. The upper level is anchored by a luxurious primary retreat featuring a private balcony, fireplace, custom dressing rooms, and a spa-inspired ensuite. Additional bedroom suites offer exceptional comfort with custom finishes, walk-in closets, and ensuite bathrooms. The lower level is dedicated to recreation and wellness, featuring a state-of-the-art home theatre, games area, fitness studio, sauna, custom bar, wine display room, and expansive entertainment spaces. Outdoors, the estate transforms into a private resort oasis, featuring meticulously landscaped grounds, extensive entertaining terraces, and a spectacular pool setting that offers complete privacy and tranquility. Located in one of Oakville's most prestigious neighbourhoods, this exceptional residence is moments from top-ranked schools, downtown Oakville, lakefront parks, private clubs, and all the amenities that define this premier community. A truly remarkable family estate where architectural excellence, luxury, and lifestyle converge.

262 Maple Grove Drive, Oakville

129 WOLFDALE Avenue, Oakville
$7,470,000
5 Beds ⋅ 7 Baths ⋅ W13429066 MLS
Welcome to 129 Wolfdale Ave, a custom-designed modern craftsman estate, positioned on a premium lot in Southwest Oakville. With approximately 7,300 sq.ft. of living space, and an incredible 1,700 sq.ft. two level garage that stores 6 cars indoors, serviced by a car elevator. This exceptional home blends refined architecture resort-inspired outdoor living, surrounded by a private, tree-lined backdrop. The portico leads into a breathtaking foyer, setting the stage for the elegant interiors beyond. Considered finishes include coffered ceilings, herringbone marble flooring, and wide-plank oak throughout the principal spaces. A stylish main floor office, complete with bespoke millwork. The great room features 14' ceilings, a custom walnut media wall, and a floor-to-ceiling stone fireplace. This space flows effortlessly into the chef's kitchen, beautifully appointed with a full Thermador fridge and freezer, Gaggenau double ovens, range, steam oven, warming drawer, and quartz countertops. A fully equipped butler's pantry that keeps entertaining effortless. The upper-level hosts four spacious bedrooms, each with private ensuites with heated floors. The primary suite is a true retreat, featuring a private balcony, a spa-inspired five-piece ensuite, and a custom walk-through closet. The finished lower level offers additional living space, including a fifth bedroom, walk-up access to the rear garden, gym and home theatre. All six garage spaces, along with driveway and front walkway are radiant heated, ensuring year-round comfort and no snow buildup. Luxury Certified.

129 WOLFDALE Avenue, Oakville

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