Oakville Real Estate | Oakville Properties between $4,000,000 and $5,000,000 for Sale

A reimagined historic farmhouse that blends timeless architectural charm with warm natural finishes and a soft colour palette. This heritage home offers over 7,000 square feet of luxury living space, where timeless character and sophisticated modern design come together seamlessly. Every detail, from the craftsmanship to the carefully curated finishes, has been completed to an exceptional standard. Elegant design elements include wide oak plank flooring, black accent hardware, shiplap detailing, and a striking open staircase with tempered glass railings. The chef-inspired kitchen is designed for both everyday living and entertaining, featuring professional-grade appliances, a large centre island, custom cabinetry, and quartz countertops. The kitchen flows seamlessly into the oversized great room highlighted by expansive architectural Kolbe windows, a coffered ceiling, and a dramatic five-foot gas linear fireplace with a steel surround. Automated blinds and lighting enhance the main floor living ares. A separate living room offers inlaid herringbone oak flooring and access to the wraparound covered verandah. Upstairs, the impressive hallway showcases 14-foot ceilings and oversized skylights, leading to four spacious bedrooms, each with a private ensuite featuring heated floors. The primary retreat includes a generous walk-in dressing room and a spa-inspired five-piece ensuite complete with a freestanding tub, double vanity, heated porcelain floors, heated towel rack, and glass enclosed walk-in shower. The fully finished lower level offers a spacious recreation area with 9-foot ceilings, home gym area, wet bar, 3-piece bathroom, and roughed-in theatre room. Additional highlights include a centrally heated garage equipped with two EV chargers. Outside, the beautifully landscaped property features perennial gardens, a covered terrace, and a circular driveway. Ideally located across from Appleby College, a short walk to the lake and moments from downtown Oakville.

489 Lakeshore Road W, Oakville

$4,695,000

W13756534 MLS

183 Maurice Drive, Oakville. 12-Suite Apartment Building. Exceptional Oakville Multi-Residential Investment Opportunity. Well-maintained and extensively renovated 12-suite apartment building situated on a large 118.5' x 90.29' lot in Oakville. The property offers an attractive combination of renovated suites, strong in-place income, ample parking and significant recent capital improvements. Property Highlights: *12 Residential Suites *6 x Two-Bedroom Suites *6 x One-Bedroom Suites *Approximately $215,000 Net Income *16 Surface Parking Spaces * Comprehensive Renovations and Upgrades Throughout *Numerous custom kitchens featuring quartz countertops and stainless-steel appliances *Numerous Modernized bathrooms *3/4-inch solid oak hardwood flooring in many living areas and bedrooms *Extensive Suite and Building-System Improvements - providing a substantially upgraded asset with reduced anticipated near-term maintenance and capital-expenditure requirements * High-Efficiency Viessmann Boiler - 2024 * Large 118.5' x 90.29' Lot * Recent Phase One and Phase Two Environmental Reports Available. Investment Highlights: This property presents an excellent opportunity to acquire a substantially upgraded multi-residential asset in the established Oakville market. The suites and major building systems have been extensively updated, providing a turnkey investment with significantly reduced anticipated maintenance requirements for the foreseeable future. Combined with efficient building systems, generous parking, a large lot and strong in-place income, the property provides a strong foundation for long-term ownership and continued income growth.

183 Maurice Drive, Oakville

$4,898,000

5 Beds ⋅ 7 Baths ⋅ W13754410 MLS

Tucked away on a private road, south of Lakeshore, neighbouring distinguished Appleby College, The Enclave offers a blend of luxury, privacy, & timeless design in one of Oakville's most coveted neighbourhoods. Situated on the largest of only 5 lots of unparallelled privacy. Flanked to the west is Appleby College's soccer fields, and putting green to the south. Showcasing over 6,800sqft of exquisitely finished living space w 10' ceilings on all levels. Extensive custom millwork, & intricate wall panelling create an atmosphere of sophistication throughout. Custom 'Top Notch' Cabinetry features a 13ft island w walnut base, 2 dishwashers, 6 burner gas range with 2 ovens, & built-in work space for studies. 2nd lvl is anchored by an impressive primary retreat featuring a spacious walk-in dressing room and a luxurious spa-inspired ensuite. Three additional generously proportioned bedrooms, each appointed with their own private ensuite bathroom, provide exceptional comfort & privacy for family and guests alike. fully finished lwr lvl is the perfect extension of the home's luxurious living space & features in-floor heating, a spacious 5th bdrm/office w custom built-in shelving w/a private ensuite, a dedicated theatre room, an expansive games and entertainment area with pool table and wet bar, & a striking glass-enclosed fitness studio. Outside, a resort-inspired backyard oasis awaits. Professionally landscaped gardens surround a Gibsan swimming pool, while multiple outdoor living spaces provide the perfect setting for relaxation and entertaining. Enjoy summer evenings beneath the covered flagstone terrace featuring an outdoor television, gas BBQ, and elegant dining area. Perfectly enveloped by one of Canada's most prestigious educational institutions, the lake, downtown Oakville, renowned dining, boutique shopping, and waterfront trails, this exceptional residence offers a rare opportunity to experience luxury living at its finest. This is a home that truly stands apart.

456 Lakeshore Road W, Oakville

$4,250,000

4 Beds ⋅ 6 Baths ⋅ W13733644 MLS

Positioned on a rare 0.8-acre ravine lot in one of Southeast Oakville's most coveted neighbourhoods, this exceptional residence makes an immediate impression with its stately curb appeal and beautifully landscaped grounds. Framed by mature trees and offering exceptional privacy, the home presents a refined presence that blends seamlessly with its lush, natural surroundings. Inside, 7,000 sq. ft. of elegantly finished living space unfolds. A grand foyer sets the tone, complemented by rich hardwood flooring and soaring ceilings throughout. The home offers four spacious bedrooms, each with its own private ensuite, along with premium appliances and a custom wine cellar. A separate side entrance adds flexibility, providing a private access point with direct entry to the lower level. Designed for both elegant entertaining and relaxed everyday living, the backyard is a private resort-style retreat. A saltwater inground pool, expansive stone patio, and uninterrupted ravine views create a setting that feels more Muskoka than city. Ideally located within walking distance of Oakville's top-ranked schools and minutes from premier amenities, this home offers a rare combination of estate-scale land, striking curb appeal, and unmatched privacy in a prime urban location. Well maintained with extensive upgrades, it reflects true pride of ownership throughout.

437 Cairncroft Road, Oakville

$4,788,500

5 Beds ⋅ 6 Baths ⋅ W13730146 MLS

Introducing a truly exceptional property that redefines luxury living, elegance, and comfort! Nestled in the best location of South East Oakville, this magnificent house is a testament to sophisticated design and meticulous attention to detail. As you step into the grand foyer, you're immediately greeted by an open floor plan that seamlessly blends spaciousness and intimacy. The sprawling 7000+ square feet of living space showcases a harmonious blend of modern architecture and timeless craftsmanship, creating an atmosphere of refined opulence. The heart of this home is undoubtedly the state-of-the-art German kitchen. Equipped with the latest appliances, custom cabinetry, and high-end finishes, it's a culinary haven for the gourmet enthusiast. Whether you're entertaining guests or preparing a family meal, this kitchen is designed to elevate your culinary experience to new heights.

1286 Cambridge Drive, Oakville

$4,999,000

5 Beds ⋅ 7 Baths ⋅ W13706006 MLS

POWER OF SALE: Welcome to a true entertainer's residence - a 2023 build by Ambassador Fine Custom Homes, set on a 0.36-acre lot in one of Southwest Oakville's most coveted enclaves. Spanning 7,276 square feet across three finished levels, this estate home pairs architectural drama with impeccable craftsmanship. A 22-foot grand foyer draws you in, opening to a soaring 24-foot atrium crowned by a skylight and anchored by a sculptural circular staircase - a showpiece bathed in natural light. Radiant heated porcelain floors and near 11-foot ceilings carry that same sense of scale across the main level, complemented by a private home office, an elevator servicing all three floors, and a temperature-controlled wine cellar built for 180+ bottles. At the heart of the home, the kitchen commands attention: a 10-foot waterfall island, quartz slab backsplash, and two-toned custom cabinetry, outfitted with Wolf, Sub-Zero, and Miele appliances. It flows seamlessly into the great room and dining room - an open-concept design made for large-scale entertaining - while a tucked-away mud room, walk-in closet with custom shelving, and an elegant powder room keep daily life organized with direct access to the garage and rear yard. Upstairs, a vaulted, skylit hallway leads to a primary suite spanning the rear of the home, framed by backyard views and anchored by a spa-inspired ensuite and a skylit walk-in closet. Three additional bedrooms - each with its own ensuite - a library, and a laundry room complete the level, every space individually finished with its own character. Refined, light-filled, and built without compromise. 150 Wolfdale Avenue is a rare offering for the discerning buyer.

150 Wolfdale Avenue, Oakville

$4,248,000

7 Beds ⋅ 7 Baths ⋅ W13685756 MLS

Welcome to 1399 Willowdown Road, an exceptional custom residence inspired by Frank Lloyd Wright's iconic Prairie designs, nestled on a spectacular ravine lot with a picturesque creek in prestigious South Oakville. Offering over 6,800 sq. ft. of beautifully finished living space, this remarkable home features 5 bedrooms upstairs plus 2 additional bedrooms in the finished lower level. The main floor impresses with soaring 10' ceilings, wide-plank oak flooring, custom millwork and an open-concept layout. At its heart is a chef-inspired kitchen with an oversized island, quartz counters, JennAir Professional Series appliances, extensive cabinetry and a butler pantry, opening to the expansive great room and breakfast area. Enjoy seamless indoor-outdoor living from the covered lanai with a fireplace and skylights overlooking the ravine. The finished lower level is designed for entertaining, featuring a dedicated home theatre, billiards and recreation areas, exercise room, 2 bedrooms and a full bathroom. Additional highlights include Lutron lighting automation, remote-controlled blinds, built-in ceiling speakers, multi-camera security, illuminated stair treads, 9' upper-level ceilings and a double garage. Just steps from Coronation Park and Lake Ontario, and minutes to top schools, shopping, dining and GO Transit. A truly rare offering combining architectural distinction, exceptional space and ravine-side privacy.

1399 WILLOWDOWN Road, Oakville

$4,689,000

8 Beds ⋅ 9 Baths ⋅ W13673406 MLS

This exceptional property presents a unique opportunity for multi-generational living or income-generating potential with its fully self-contained in-law suite.Situated on a quiet tree-lined street in the highly sought-after Ford area,this impressive residence offers over 5,600 square feet of total living space,thoughtfully designed to accommodate a variety of modern lifestyles. The main house features 4+1 bedrooms and 5 baths.Step into the double-height foyer, where a statement chandelier sets the tone for the sophisticated interiors and open concept main living area with separate office area.The heart of the home is a custom-designed chef's kitchen,outfitted with premium Wolf and Sub-Zero built-in appliances,incl a beverage fridge. An oversized island,wide plank oak hardwood flooring,high-end lighting, and a spacious main floor laundry/mudroom with abundant storage complete the refined main level. Floating stairs lead you to the 2nd level.The principal bedroom features a walk in closet and 5pc spa like ensuite.3 additional bedrooms and 2x4 pc bathrooms offer comfort and privacy.The finished lower level includes an additional 5th bedroom,recreation space, a 4pc bathroom, & rough-in home theatre area. Connected via the mudroom but also offering a private separate entrance,the second dwelling home offers 2,056+ square feet of thoughtfully appointed living space.The main floor features living/dining & kitchen area with stainless steel appliances.The 2nd level with principal bedroom,walk in closet and 5 pc ensuite.2 additional bedrooms with shared ensuite access and conventiently located laundry room completes this level.Fully finished basement with wet bar and 4-piece bath.This home is perfect for extended family or tenants. Set on a large,pool-sized lot,the backyard awaits your personal touch-ideal for creating a private outdoor retreat. Don't miss the opportunity to live in one of Oakville's great neighbourhoods! Luxury Certified.

319 Beechfield Road, 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

$4,349,000

5 Beds ⋅ 6 Baths ⋅ W13670214 MLS

Set on a premium 60-foot lot in one of Oakville's most coveted pockets, this extraordinary custom residence offers over 5,800 square feet of meticulously crafted living space that redefines modern luxury through uncompromising engineering and timeless European-inspired design. Built with insulated concrete forms (ICF) extending through the second floor, the home features high-performance European windows, extensive microcement finishes, radiant heated floors throughout-including the basement and garage-and a striking architectural cantilever staircase. Highlights include a stunning main kitchen with a separate butler's pantry, an exceptional lower-level entertainment zone complete with a custom microcement bar, walk-in wine display, and private home theatre, plus a car-enthusiast garage and a backyard featuring an approved pool permit. With an estimated completion of October 2026, the purchaser still has a rare opportunity to select and customize final finishes. A masterclass in contemporary craftsmanship, delivering an unmatched standard of refined, energy-efficient living.

1387 WAVERLY Avenue, Oakville

$4,850,850

5 Beds ⋅ 6 Baths ⋅ W13664174 MLS

Perfectly Positioned Along South Oakville's Prestigious Lakeshore Road Corridor, This Custom-Built Residence Offers Approx 6,596 Sqft Of Finished Living Space In The Heart Of Bronte. A Dramatic Cathedral Foyer Introduces Interiors Finished W/ Imported Crema Marfil Marble, Custom Millwork, Architectural Wall Detailing, Designer Lighting & Integrated Ceiling Speakers Throughout. The Living & Dining Rooms Are Ideal For Both Intimate Gatherings & Large-Scale Entertaining, While The W/O Family Room Is Anchored By A Handcrafted Fluted Travertine Marble F/P. At The Centre Of The Home Is A Spectacular Chef's Kitchen Featuring Backlit Onyx Marble Countertops & B/S, An Oversized Island & A Full Suite Of Premium Sub-Zero And Miele Appliances. A Stylish Powder Room & Functional Mudroom W/ Garage Access Complete The Main Lvl. The Upper Lvls Offer 4 Luxurious Bedroom Suites, Each W/ Custom Closets, Designer Finishes, Heated Ensuite Floors, Integrated Speakers & Motorized Shades. The Third-Level Primary Retreat Is Truly Exceptional, Featuring A Boutique-Inspired Dressing Room With Illuminated Glass Cabinetry, Custom Organizers, Gold Hardware, A Pvt Sitting Area W/ F/P & A Spa-Inspired 5-Pc Ensuite. The Fully Finished Lower Lvl Provides An Expansive Rec Space W/ Theatre Speakers, Custom Wainscoting, LED Lighting & A 3-Pc Bath. A Dedicated Office Or Optional Fifth Bedroom Adds Flexibility For Growing Families Or Guests. Outside, Enjoy A Pvt, Maturely Landscaped Bkyd W/ An Expansive Stone Patio, Pergola W/ Retractable Canopy, Ambient Lighting, Irrigation System & Established Privacy Screening. The Circular Driveway Accommodates Over 12 Vehicles, While The Attached Garage Features A Dramatic Full-Glass Door And A Four-Post Vehicle Lift. Steps To Bronte Village, Bronte Harbour, Waterfront Trails, Parks, Marinas, Top-Rated Schools, Appleby College, Bronte GO & The QEW. A Rare Opportunity To Own A Truly Exceptional Family Estate In One Of Oakville's Most Coveted Waterfront Communities.

3168 Lakeshore Road W, Oakville

$4,099,000

4 Beds ⋅ 4 Baths ⋅ W13617444 MLS

An exceptional opportunity to own a luxurious family residence in one of Southeast Oakville's most prestigious lakeside neighbourhoods. Ideally situated south of Lakeshore Road and just three homes from the lake, set on a spectacular approximately 109 by 189 foot lot, the property is surrounded by extensive professional landscaping, mature trees, stonework, and a beautifully designed backyard featuring a heated saltwater pool. With more than 5,000 square feet of refined living space, the home has been thoughtfully designed for comfortable family living and sophisticated entertaining.The versatile floor plan offer 3 bedrooms on the second floor and two bedrooms on the main level. The luxurious primary suite provides a peaceful private retreat with generous closet space, a private balcony overlooking the landscaped grounds, and a spa inspired ensuite complete with heated floors, dual vanities, a glass enclosed shower, and a deep soaker tub. At the heart of the home is the impressive great room, featuring soaring coffered ceilings, a gas fireplace. The kitchen offers an inviting gathering space for everyday living and entertaining, while the separate living and dining rooms provide additional elegance and functionality. Located moments from the lake, waterfront trails, parks, shopping, dining, and major commuter routes, the home is also situated within the highly sought after Maple Grove Public School and Oakville Trafalgar High School catchments and close to several of Canada's finest private schools. This is a rare opportunity to own an exceptional estate on one of South Oakville's most desirable streets, offering an extraordinary combination of location, lifestyle, privacy, and luxury

75 Arbour Drive, Oakville

$4,450,000

5 Beds ⋅ 6 Baths ⋅ W13591888 MLS

Architect-designed. Never lived in. Statement residence in Bronte. Crafted by Ni Ni (B.C.I.N. #41885), this custom contemporary sits on a rare pie-shaped lot with exceptional rear width and privacy, minutes to Lake Ontario, Bronte Marina and waterfront trails. Not builder-grade-designed, permitted and executed to a cohesive architectural vision. The home offers 5 bedrooms, 6 bathrooms and a dedicated pet spa. A grand foyer opens to an open-concept living area anchored by a dramatic 23-ft floor-to-ceiling window wall. Premium aluminum gliding windows with German hardware, engineered white oak flooring and ambient pot lighting enhance the bright, airy feel. Chef-inspired kitchen with top-of-the-line Dacor appliances, custom cabinetry, Calacatta marble backsplash, pot filler and a waterfall island. Napoleon fireplaces in living and family rooms. Main floor guest suite with private ensuite; private office with separate backyard entrance. Cambridge hydraulic elevator to all levels. Upstairs: three bedrooms with spa-inspired ensuites, walk-in closets and 12 ft 3 in ceilings. Fully finished walkout lower level with radiant heated floors (ready), home theatre, recreation space, full kitchen/bar, guest suite, oversized cold storage and direct backyard access via premium aluminum doors. Exterior: fully fenced yard with aluminum perimeter and frameless glass railings; large inground pool with heating provisions; heated driveway permit approved. Systems and extras: Control4 automation (3 iPads), whole-home audio, security system, central vacuum, 3 fireplaces, 4 skylights, BBQ rough-in and parking for up to 8 vehicles. A rare, meticulously executed contemporary home offering luxury, functionality and proximity to Bronte's waterfront lifestyle.

468 Saville Crescent, Oakville

$4,999,369

5 Beds ⋅ 7 Baths ⋅ W13571822 MLS

Welcome to 150 Wolfdale Avenue. Entertainers dream home, built by Ambassador Fine Custom Homes in 2023 fall, on a 0.36 acres in Southwest Oakville, south of Lakeshore Road. With 7276 square feet of living space on all three levels, this home perfectly combines sophisticated luxurious design with quality construction to create the ultimate package. The main floor is beautifully designed with exquisite detail radiant heated large porcelain tiles. The near 11-foot ceilings provide an open-airy feeling throughout. No estate home would be complete without a grand foyer and and this home has just that with 22 -foot ceilings, center of the house with 24-foot ceilings with large skylight allowing the entire house to be flooded with natural light while also highlighting the stunning hanging circular staircase beneath. Built-in wine cellar storage for over 180 bottles. The kitchen is a show piece with stunning 10-foot waterfall island, quartz slab backsplash and two-toned cabinetry and top-of-the-line Wolf ,Sub-Zero & Miele appliances. The kitchen/great room combination is designed for large scale entertaining with it being open concept to the dining room. A tucked away mud room, walk in closet with custom shelving & an elegant custom powder room are the perfect spaces to keep your family organized while providing inside access to both the garage and rear yard. Main floor you find your primary home office with front yard views. Elevator besides mud area travels all 3 floors for convenience of movement. The upper hallway stops you with a beautifully vaulted ceiling, skylights. Primary bedroom is located across the rear of the home taking in the best views of the backyard with ample natural light. The open concept walk-in closet with a skylight complements the primary ensuite, is a beautiful combination of rich tones to create the ultimate spa oasis. 3 additional bedrooms, Laundry & Library are found upstairs, each one uniquely decorated & appointed with closets and ensuites.

150 WOLFDALE Avenue, Oakville

$4,399,000

4 Beds ⋅ 6 Baths ⋅ W13564032 MLS

Many homes make a wonderful first impression. The best reward your attention until you reach that quiet moment when you begin to understand what makes them truly exceptional. That is the difference between a house that is simply well built and one that has been thoughtfully conceived. It is found in the effortless flow from one space to the next, the way natural light fills the home throughout the day, and the balance between grand entertaining spaces and comfortable everyday living. Newly built by a Tarion Registered builder, this exceptional custom residence offers over 6,300 square feet of finished living space on a premium 75 x 140 foot lot just steps from the lake in Bronte. A soaring 22-foot foyer introduces 11-foot ceilings throughout the main level and a dramatic oak staircase that serves as both an architectural centrepiece and the heart of the home. Formal living and dining rooms create an elegant arrival, while the spectacular great room, expansive kitchen, chef's kitchen and servery provide a setting equally suited to intimate family evenings or entertaining on a much larger scale. Sub-Zero and Wolf appliances, a private elevator and thoughtfully integrated technology reflect the same disciplined approach to design found throughout the home. The upper level continues the same philosophy. A remarkable primary retreat with fireplace, expansive dressing room and luxurious ensuite is complemented by three additional bedroom suites, each with its own ensuite and walk-in closet. The lower level is planned with the same attention to detail, offering generous recreation space, a dedicated theatre, gym, office, bar and elevator access, creating exceptional flexibility for entertaining, extended family or everyday living. Sophisticated home automation, integrated audio and an advanced mechanical package complete a residence where every decision has been made with purpose. Perhaps that is why the finest homes are remembered long after the features fade from memory.

146 Third Line, Oakville

$4,895,000

4 Beds ⋅ 5 Baths ⋅ W13545876 MLS

Experience lakeside living in one of South Oakville's most exclusive enclaves. This luxurious custom-built executive home is situated on a premium wooded lot in a private lakeside pocket just one lot from the water, with walkway access from Shorewood to the waterfront and the secluded Shorewood Promenade Waterfront Park your private oasis on the water. Ideally located south of Lakeshore, this residence offers the perfect balance of privacy, scale, and lifestyle - only minutes from downtown Oakville's restaurants, boutique shopping, the lake, and prestigious Appleby College. Offering over 6,000 sq. ft. of total living space, this exceptional home features 4+1 bedrooms, 4.5 bathrooms, a dedicated music room, theatre room, home gym, formal living and dining rooms, a spacious family room, and a private den. The chef-inspired kitchen, designed by Bella Kitchens, serves as the centrepiece of the main floor with premium finishes, thoughtful design, and excellent flow for both everyday living and entertaining. The main floor primary retreat provides comfort and convenience, while three additional spacious bedrooms offer flexibility for family or guests. Throughout the home, you'll find hardwood floors, 10-foot ceilings, 8-foot doors on the main level, and refined architectural details that create a timeless executive feel. The walk-out lower level expands the living experience with a large recreation area, theatre room, gym, and additional bedroom space - ideal for multi-generational living, guests, or a complete lifestyle retreat. Set within a quiet, prestigious lakeside neighbourhood, this home delivers rare privacy, exceptional square footage, and direct access to one of Oakville's most desirable lifestyle settings - all just five minutes from the restaurants, shops, and amenities of downtown Oakville, with easy commuter access.

45 Shorewood Place, Oakville

$4,999,000

4 Beds ⋅ 5 Baths ⋅ W13524820 MLS

Grand Grounds. Timeless Elegance. Extraordinary Potential.An exceptional opportunity in one of Olde Oakville's most prestigious neighbourhoods. Tucked behind private gates and nestled beneath a magnificent canopy of mature trees, this beautifully landscaped and increasingly rare 0.82-acre estate offers over 7,100 square feet of living space in an irreplaceable setting just moments from Downtown Oakville.Approached by a sweeping circular drive, the timeless brick residence immediately impresses with its classic Colonial Williamsburg-inspired architecture, elegant symmetry, and commanding presence. Beyond the front entrance, peaceful views of the private pond and lush landscape create a tranquil, park-like retreat rarely found in such a coveted urban location.Custom built in 1980, this stately four-bedroom residence offers an extraordinary opportunity to reimagine an exceptional property. Offered in "as is" condition, the home presents the perfect canvas for those looking to undertake a significant renovation, thoughtfully restore its timeless character, or explore the opportunity to create a magnificent custom estate (subject to all necessary approvals). Whether preserving its enduring architectural charm or designing an entirely new vision, the possibilities are truly exceptional.The expansive grounds provide an incredible backdrop for family living, entertaining, and creating lasting memories for generations to come. Properties offering this rare combination of land, privacy, scale, and location are becoming increasingly difficult to find.Ideally situated within one of Oakville's most sought-after school districts and just a short walk to Downtown Oakville, the Oakville GO Station, public and private schools, Post Park, Whole Foods, Longo's, boutique shopping, restaurants, and the lakefront, this is more than an exceptional property-it is a rare opportunity to create a legacy estate in one of Olde Oakville's most coveted locations.

488 Macdonald Road, Oakville

$4,499,000

5 Beds ⋅ 5 Baths ⋅ W13520422 MLS

Set on a rare and private 1/2+ acre estate lot in one of South West Oakville's most coveted lakeside neighbourhoods, this stunning custom designed home offers over 6,500 sq. ft. of luxurious living space just steps from Lake Ontario and within minutes to esteemed Appleby College. Thoughtfully designed for both everyday living and grand-scale entertaining, the home features 10' ceilings on the main level, 9' ceilings on the upper and lower levels, extensive custom millwork, rich hardwood flooring, and exceptional craftsmanship throughout. The Hampton-inspired custom kitchen and butler's pantry serve as the heart of the home, complemented by luxurious ensuite bathrooms and high-end finishes at every turn. The main floor primary retreat offers the convenience of single-level living, complete with a custom walk-in closet, spa-inspired 5-piece ensuite, gas fireplace, and serene backyard views. The fully finished lower level is ideal for multigenerational living, featuring a second kitchen, two additional bedrooms, a gym, wet bar, games area, and expansive recreation room. Step outside to your own private resort, where mature landscaping surrounds a saltwater pool, waterfall feature, and covered outdoor living area. A truly exceptional opportunity to own a custom estate property on one of Oakville's most prestigious streets, surrounded by luxury homes, steps to the lake, and moments to top-ranked schools, parks, and downtown Oakville. Some opportunities are measured in sq footage, others are measured in land, location and the life you'll build there. 1098 Lakeshore Rd is not to be missed.

1098 Lakeshore Road W, Oakville

$4,895,000

4 Beds ⋅ 4 Baths ⋅ W13519952 MLS

Welcome to 1516 Duncan Road, an extraordinary custom-built contemporary residence in prestigious Southeast Oakville where exceptional craftsmanship and state-of-the-art smart home technology come together seamlessly. Completed in 2020, this one-of-a-kind bungalow offers 5,000 sq. ft. of living space with 3+1 bedrooms, 4 bathrooms, and a residential elevator servicing all three levels, including the rooftop terrace. Soaring 15-ft floor-to-ceiling windows flood the open-concept interior with natural light while creating a seamless connection to the landscaped backyard featuring extensive hardscaping, an outdoor gas fireplace, heated outdoor living areas, and exceptional privacy. Polished concrete floors with hydronic radiant heating, custom cabinetry, and natural stone finishes define the sophisticated interior. The designer kitchen is equipped with Thermador and Bosch appliances, Brazilian Black Fusion stone countertops, double ovens, a barista station, and a wet bar featuring Grohe Blue chilled, sparkling, and filtered water. The tranquil primary suite overlooks a private bamboo courtyard and offers custom built-ins and a luxurious spa-inspired ensuite. The finished lower level is designed for entertaining with a games area, wet bar featuring Avocatus quartzite, dedicated home theatre, guest suite, and family room. Smart living is elevated through Lutron lighting, Home Assistant automation, Sonos audio, a 24-camera surveillance system, fibre internet with Starlink backup, motorized shutters, and whole-home smart leak protection. Highlights include a heated driveway, walkways and covered porches with integrated snow-melt system, oversized double garage with EV charger, central vacuum, smart irrigation, and low-maintenance landscaping. A truly exceptional residence blending innovative technology, timeless design, and uncompromising luxury in Oakville's most sought-after neighbourhoods.

1516 Duncan Road, Oakville

$4,265,000

5 Beds ⋅ 6 Baths ⋅ W13469458 MLS

A rare opportunity to create a new, luxurious custom-home on one of Old Oakville's most coveted streets, set on an exceptionally private, tree-lined lot. This rarely offered design features a double-car garage and a fully finished lower level, thoughtfully crafted to deliver both elegance and functionality. Enjoy the expertise of a dedicated interior designer throughout the entire building process, ensuring every finish and detail is tailored to your vision. Features include: Curated luxury finishes throughout. Personalized interior design consultation and selection services. Optional elevator upgrade available with a three bedroom floorplan. Exceptional craftsmanship by a trusted custom builder with nearly 20 years of experience. An extraordinary opportunity to build a timeless custom home in one of Oakville's most prestigious neighbourhoods. Drawings are approved by Committee of Adjustments. Projected completion date August 2027 /Permit Process Underway

343 Douglas Avenue, Oakville

$4,399,000

6 Beds ⋅ 8 Baths ⋅ W13466488 MLS

Unparalleled elegance define this exquisite luxury detached home featuring 5 + 1 bedrooms and 8 washrooms in the prestigious Bronte West community of Oakville, offering over 5,000 sq. ft. of sophisticated living space with exceptional design and premium finishes throughout. The home welcomes you with a double door entry leading into a dramatic foyer with a 22' open-to-above ceiling, 11' across and 12' in basement. Separate living and dining areas are complemented by large windows, while the impressive family room boasts a 22' open-to-above ceiling, a gas fireplace, and expansive window. The main floor also includes a mud room for added practicality, seamlessly connecting the garage entry to the living spaces.The gourmet kitchen is equipped with built-in SS appliances, a pantry, a servery, and a breakfast area combined with the kitchen, with a walk-out to a terrace ideal for entertaining large gatherings. A private elevator, connecting all levels of the home with ease and comfort.The second floor offers a luxurious primary suite featuring his-and-her closets with a skylight and a 5-piece ensuite with dual sinks, while 4 additional spacious bedrooms each include their own closets and private ensuites, along with a second-floor laundry for added functionality. The fully finished walk-out basement includes a 1-bedroom suite, 2 bathrooms, a recreation room with wet bar that can be converted into a second kitchen, a home gym and a dedicated home theatre for entertainment, along with a cold room, plus a second laundry area in the basement for added convenience. The beautifully landscaped backyard creates a resort-style setting perfect for relaxation and entertaining. Ideally located just minutes from Coronation Park, the lakeshore, top-rated schools, fine dining, boutique shopping, and cultural amenities. Taxes have not been assessed yet.

1042 Bridge Road, Oakville

$4,999,999

W13181868 MLS

Slightly over 2 Acres development land, Zoned H4-E4 permits for broad variety of uses, has a workshop & house in need of TLC. Great property for great Development, the adjacent properties (2024 & 2056 or more) can be purchased together for a big project.

2036 Upper Middle Road E, Oakville

$4,500,000

5 Beds ⋅ 7 Baths ⋅ W13019360 MLS

Beautiful Custom Built Home In Fabulous Southeast Oakville Location. 4,140 Sq Ft. Very Private And Bright Corner Lot. Spacious Side Centre Hall Plan With Expansive Kitchen, Family Room And Walk-Out To 335 Sq Ft Of Covered Deck. Gas Line On The Deck And Walk Out To Backyard Oasis. Still Room To Add A Pool. Main Floor Has Separate Formal Living Room, Dining Room And Home Office. 24 X 21 Double Garage Will Hold Two Cars Easily. ALL 4 Bedrooms On The Second Floor Have Ensuites. Second Floor Also Has Laundry Room With Side By Side Machines. Lower Level Has 2 Potential Extra Bedrooms, Screening Room, Wet Bar, Wine Cellar, Gym. Winding Streets And Mature Trees Characterize This Prime Eastwood Neighbourhood. Established, Family Community With Excellent Schools. Walk To Maple Grove Public, St. Vincent, Oakville Trafalgar High School & Ej James. QEW And Lakeshore Blvd Equidistant. Trails To The Lake Are Close By.

302 Pinehurst Drive W, Oakville

$4,290,000

4 Beds ⋅ 4 Baths ⋅ W12899014 MLS

Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. The Douglas Collection is an extension of the inaugural development with an exclusive collection of seven homes located on Douglas Avenue. Distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. "The Chatsworth"; detached home with 48-foot frontage, between 3,188-3,204sf finished space w/an additional 1,000+sf (approx)in the lower level & 4beds & 3.5 baths. Utility wing from garage, chef's kitchen w/w/in pantry+ generous breakfast, expansive great room overlooking LL walk-up. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment.

Lot 101 Douglas Avenue, Oakville

$4,779,000

W12807870 MLS

Incredible turn-key 5,463 SF corner unit available for sale at the highly desirable Maple Grove Corporate Centre in the heart of Oakville's thriving business corridor. Flexible layout suitable for retail or office use allowing for various uses including medical. Offering a mix of reception, open space, kitchen, boardroom, washrooms and several offices and workspaces on glass including a large outdoor patio. Located in a well-maintained complex with ample on-site parking and quick access to the QEW and Highway 403. Ideal opportunity for businesses seeking a strategic and accessible Oakville location.

1525 Cornwall Road Unit 26-27, Oakville

$4,779,000

W12807826 MLS

Incredible turn-key 5,463 SF corner unit available for sale at the highly desirable Maple Grove Corporate Centre in the heart of Oakville's thriving business corridor. Flexible layout suitable for retail or office use allowing for various uses including medical. Offering a mix of reception, open space, kitchen, boardroom, washrooms and several offices and workspaces on glass including a large outdoor patio. Located in a well-maintained complex with ample on-site parking and quick access to the QEW and Highway 403. Ideal opportunity for businesses seeking a strategic and accessible Oakville location.

1525 Cornwall Road Unit 26-27, Oakville

$4,889,915

W12750996 MLS

Three Oaks Business Centre presents occupiers and investors a rare opportunity to own state-of-the-art industrial condo including mezzanine. Built by Beedie, one of Canada's largest private industrial developers, Three Oaks Business Centre is designed to position your business for success with exceptional connectivity, operational efficiency, and the highest quality construction. Connect better with your customers and employees with direct access to the QEW.

3303 Superior Court Unit A105, Oakville

$4,835,880

W12750984 MLS

Three Oaks Business Centre presents occupiers and investors a rare opportunity to own state-of-the-art industrial condo including mezzanine. Built by Beedie, one of Canada's largest private industrial developers, Three Oaks Business Centre is designed to position your business for success with exceptional connectivity, operational efficiency, and the highest quality construction. Connect better with your customers and employees with direct access to the QEW.

3303 Superior Court Unit A102, Oakville

$4,907,430

W12750980 MLS

Three Oaks Business Centre presents occupiers and investors a rare opportunity to own state-of-the-art industrial condo including mezzanine. Built by Beedie, one of Canada's largest private industrial developers, Three Oaks Business Centre is designed to position your business for success with exceptional connectivity, operational efficiency, and the highest quality construction. Connect better with your customers and employees with direct access to the QEW.

3303 Superior Court Unit A103, Oakville

$4,745,565

W12750956 MLS

Three Oaks Business Centre presents occupiers and investors a rare opportunity to own state-of-the-art industrial condo including mezzanine. Built by Beedie, one of Canada's largest private industrial developers, Three Oaks Business Centre is designed to position your business for success with exceptional connectivity, operational efficiency, and the highest quality construction. Connect better with your customers and employees with direct access to the QEW.

3313 Superior Court Unit B108, Oakville

$4,295,000

6 Beds ⋅ 8 Baths ⋅ W12644824 MLS

This is a remarkable vacant lot that includes drawings and building permit. House pictures are renderings and details are from the drawings. Embark on a life of uncompromised luxury with this architectural masterpiece by renowned architect David Small. Perfectly located South of Lakeshore steps from Appleby College, lake and downtown Oakville. Evoking a sophisticated "Laneway Country" atmosphere on a rare 90' x 340' lot with walk-out basement. The estate features a long circular private drive that frames a sun-drenched, West-facing backyard. The home is designed as the ultimate multi-generational sanctuary, that offers a rare "Double Primary" layout: a magnificent main-floor master suite for accessible luxury, plus a second-level master retreat with separate "His & Her" ensuites. The elevator services all three levels, ensuring effortless movement throughout soaring interiors defined by dramatic cathedral ceilings. With building permits in hand and a bespoke interior package by WOLFE Interior Design, this Net Zero Ready estate blends timeless character with elite modern performance. Car enthusiasts will prize the 5-car capacity, utilizing the attached garage and the detached tandem garage within the cabana. Beyond the essentials, the floor plan is packed with exceptional features, including a main floor office, lower level dedicated music/theater room, glass-walled fitness center, custom sauna and steam room, wine cellar, and private nanny and guest suites. Surrounded by 10M-12M estates. Architectural drawings, interior design, floorplans and building permits available on request. 10+++

408 Lakeshore Road W, Oakville

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