Oakville Real Estate | Oakville Properties between $2,500,000 and $5,000,000 for Sale

A meticulously maintained family home in Joshua Creek, built by Fernbrook and thoughtfully upgraded by its original owners over two decades.The main floor features 10-foot ceilings throughout, with an open plan encompassing a home office, sitting room, powder room, and great room with vaulted ceilings and gas fireplace. The formal dining room includes a servery. The kitchen centers around a substantial island with extensive cabinetry. A mudroom provides direct garage access.Nine-foot ceilings continue on the upper floor, where four generous bedrooms and three bathrooms are arranged. The primary suite occupies its own wing with a sitting area, gas fireplace, dual walk-in closets, and a spa-inspired ensuite.The lower level features 9 and 10-foot ceilings and includes a family room with gas fireplace, gymnasium, billiards room, wet bar, steam shower, and state-of-the-art theatre room with integrated sound system. New wide-plank oak flooring spans the main level. Crestron and Nest smart home systems control music, lighting, climate and the alarm system throughout.Outside, $150,000 in professional landscaping surrounds a fresh water pool, with mature plantings and custom lighting creating privacy. The property includes security cameras and a comprehensive alarm system.Top-rated schools within the district. Highway access, premium shopping, and dining including Narenj, Oak Cafe Gallery, and BLK & CO all within ten minutes.

1468 Ferncrest Road, Oakville

$2,999,999

5 Beds ⋅ 2 Baths ⋅ W13423850 MLS

Rare opportunity in coveted Orchard Beach, just steps from Lake Ontario and the waterfront trail. Set on a premium 50 x 160 ft lot, this property comes with completed architectural and engineering drawings and Committee of Adjustment approval for a proposed 3,800 sq ft residence. An exceptional offering for a buyer looking to move forward with confidence, with extensive completed work including floor plan and exterior concepts, colour renderings, arborist report, architectural drawing package, sealed roof truss package, sealed LVL layout, sealed structural engineering package, HVAC design, grading and drainage plan, soil test, and stormwater management report.The existing home was updated in 2024 with electrical improvements, a renovated bathroom, updated flooring, a new kitchen, and new appliances, offering flexibility to live in or hold the property while completing the final permit stage. Zoning and Committee of Adjustment approvals are already in place, with remaining steps in progress. Located a short stroll from downtown Oakville, the lake, and top schools, this is a rare opportunity to secure a prime property with meaningful value already created.

25 Howard Avenue, Oakville

$2,799,000

4 Beds ⋅ 3 Baths ⋅ W13419974 MLS

Welcome to 150 Cairncroft, a rare opportunity to own a distinctive property in one of Oakville's most coveted neighbourhoods. Nestled on a stunning 0.4 acre (17,416 sq ft) corner lot, this charming 3,052 sq ft residence is enveloped by mature trees and lush landscaping, offering the perfect blend of privacy and prestige. Set just steps from the lake and picturesque Gairloch Gardens, the location is unparalleled for those seeking an upscale lifestyle surrounded by nature, yet within easy reach of top-rated schools, downtown Oakville, major commuter routes & transit. Whether you're looking to move right in, renovate, or build your custom dream home (RL1-0 zoning), this property delivers exceptional potential. The existing home is rich in character and warmth with its Mediterranean-inspired façade and design, offering 4 bedrooms + den, and 2.5 bathrooms. The living room showcases exposed structural beams set amongst 1 of this home's 4 cozy fireplaces, lending a rustic allure and architectural interest. While the soaring two-storey foyer also offers captivating views of the inviting yet secluded courtyard-style patio - ideal for entertaining or relaxing under the canopy of greenery. Properties of this caliber and location are exceedingly rare. Don't miss your chance to secure a premium foothold in a neighbourhood known for luxury homes, timeless appeal, and rare public lakefront access only steps away!

150 Cairncroft Road, Oakville

$2,998,000

5 Beds ⋅ 6 Baths ⋅ W13417780 MLS

Luxury living redefined in South West Oakville. This exceptional custom-built home offers over 4,200 sq. ft. of beautifully appointed living space with custom millwork, designer finishes, and impeccable attention to detail throughout. The open-concept layout is anchored by a chef-inspired kitchen with oversized quartz counters and premium integrated appliances. The primary suite features coffered ceilings, a walk-in closet, and a spa-inspired 6-piece ensuite. A rare walk-out basement provides additional living and entertaining space. Over $600K in recent upgrades have transformed the property into a private resort-style retreat featuring a 16' x 34' saltwater pool, custom cabana with gas fireplace, built-in BBQ, and commercial-grade fridge, all surrounded by mature European Beech trees and extensive landscaping. Premium AV system, irrigation, landscape lighting, heated epoxy garage with EV charging, security system, and six-car parking. Brand New 2026 AC 3Ton Unit with a 10 year Parts Warranty. Steps to Lake Ontario and top-ranked schools. A turnkey offering in one of Oakville's most coveted neighbourhoods.

1298 Pinegrove Road, Oakville

$4,099,000

5 Beds ⋅ 6 Baths ⋅ W13417462 MLS

Why are some homes comfortable from the moment you walk through the door? Why does movement seem effortless, light arrives exactly where it should and every room connects naturally to the next? The answer is rarely found in a list of finishes. It comes from design. Every detail has been thoughtfully considered. From the moment you enter 152 Third Line, sightlines extend through the home toward the rear gardens, creating an immediate sense of openness and calm. Natural light, thoughtful proportions and carefully selected materials work together to create a residence that feels both sophisticated and remarkably comfortable. Newly built by a Tarion Registered builder and meticulously executed, this custom home offers over 5,500 square feet of finished living space on a premium 75 x 140 foot lot steps to the lake in Bronte. What distinguishes the home is not simply the quality of its finishes, but the way it has been conceived. Not just a collection of luxury features, it is a residence where architecture, craftsmanship and functionality work together seamlessly. At the heart of the home are two exceptional kitchens. The main kitchen features an oversized island and a natural connection to the surrounding living and dining spaces, while a fully equipped secondary kitchen provides flexibility for entertaining or serious cooking. A sculptural oak staircase with glass railings and integrated lighting connects all three levels, complemented by the convenience of an elevator. The primary suite is a private retreat with a beautifully appointed ensuite and custom walk-in dressing room. Three additional bedrooms have private ensuites and built-in storage. The walk-out lower level includes recreation space, a home theatre, an office, bar and guest accommodation potential. The sophisticated home automation, integrated audio and mechanical package deliver comfort and convenience behind the scenes. The finest luxury is found in the details you feel not the features you see.

152 Third Line, Oakville

$3,188,000

4 Beds ⋅ 4 Baths ⋅ W13415046 MLS

Experience exclusive lakefront luxury living at The Gardens of Edgemere, one of South East Oakville's most prestigious private enclaves. This rare "lock-and-leave" Ivy TownManor blends the timeless character of Oakville's historic lakefront estates with refined contemporary design, offering approximately 2,318 sq ft above grade and nearly 2,800 sq ft of total luxury living space.Surrounded by professionally landscaped grounds, residents enjoy access to a lakefront promenade, historic Japanese Teahouse, pergola, rose garden, greenhouse, conservatory, and beautifully maintained gardens-all in a serene estate-like setting.Inside, soaring 10-foot main-floor ceilings, floor-to-ceiling windows, and two bright skylights fill the home with natural light. Enjoy lake views from all bedrooms, plus lush ravine views from the private rear terrace and primary ensuite. The showpiece kitchen features upgraded full-height cabinetry and premium Wolf, Sub-Zero, and Miele appliances, while built-in speakers and two gas fireplaces add warmth and comfort.The upper level offers three spacious bedrooms, all with LED pot lights and custom closet organizers. Heated floors in all bathrooms enhance the spa-like feel, while the primary retreat captures breathtaking lake and ravine views from both the bedroom and luxurious ensuite. Convenient upper-level laundry adds everyday ease.The lower level features a luxurious den or guest bedroom, plus direct access to a private two-car underground garage via a heated driveway, complete with upgraded lighting and shelving.Relax or entertain on the private 391 sq ft rear terrace overlooking tranquil ravine views. Ideally located near top public and private schools, downtown Oakville, the lake, shops, restaurants, parks, and transit, this exceptional residence offers rare lakefront luxury, privacy, and convenience in the heart of South East Oakville.

10 MAPLE GROVE Drive Unit 14, Oakville

$2,799,000

5 Beds ⋅ 5 Baths ⋅ W13414950 MLS

Exceptional Custom Luxury Residence On A Rare Corner Lot In Prestigious West Oakville. Designed For Modern Living, This 4+1 Bedroom, 4.5 Bathroom Smart Home Showcases Soaring Ceilings, Sun-Filled Interiors, And High-End Finishes Throughout.Chef-Inspired Kitchen With Premium Cabinetry, Heated Floors, Caesarstone Surfaces & Oversized Island Anchors The Main Floor, Flowing Into Elegant Living & Dining Spaces And A Cozy Family Room With Fireplace & Walkout To A Beautifully Upgraded Yard. Main Floor Office & Direct Garage Access Add Everyday Convenience.Upper Level Features A Serene Primary Retreat With Spa-Like Ensuite & Heated Floors, Alongside Generous Secondary Bedrooms With Ensuite & Jack & Jill Access. Finished Lower Level Offers Bright Living Space, 5th Bedroom & Walkout.Fully Integrated Smart Home With Advanced Security, Whole-Home Wiring, Mesh WiFi & Multi-Zone Audio. Extensively Enhanced By Current Owner With Custom Window Coverings, Professionally Improved Yard With Fruit Trees, Upgraded Safety Features, Regraded Lawns & Improved Walkways.Gently Lived In For Under One Year - A Rare Opportunity To Own A Nearly-New, Move-In Ready Luxury Home.

476 TENNYSON Drive, Oakville

$2,549,000

5 Beds ⋅ 5 Baths ⋅ W13412994 MLS

5 Elite Picks! Here Are 5 Reasons To Make This Home Your Own: 1. Stunning Gourmet Kitchen Boasting Espresso Maple Cabinetry with Upgraded Custom Features, Centre Island with Breakfast Bar, Granite Countertops, Stainless Steel Appliances, Convenient Servery Area with Bar Sink & Bright Breakfast Area with W/O to Balcony! 2. Spacious Principal Rooms... Gorgeous Great Room Featuring Large Windows & Gas Fireplace, Plus Open Concept Formal D/R & Separate Formal L/R. 3. 4 Generous Bedrooms, 3 Full Baths & Convenient Upper Level Laundry Room on 2nd Level, with 4th/Guest Bedroom Boasting Private 3pc Ensuite with Large Frameless Glass Shower. 4. Double Door Entry to Spacious Primary Bedroom Suite Featuring W/I Closet & Luxurious 5pc Ensuite with Double Vanity, Freestanding Soaker Tub & Large Glass-Enclosed Shower. 5. Bright & Beautiful W/O Basement with Spacious Open Concept Rec Room & Office Area with Large Windows & W/O to Backyard, Plus Good-Sized 5th Bedroom, Full 3pc Bath & Ample Storage! All This & More!! Gracious Dark Oak Staircase with Wrought Iron Pickets. Convenient Mud Room (with Ample Storage & Access to Garage) & 2pc Powder Room Complete the Main Level. 2nd & 3rd Bedrooms Share Access to Very Functional 4pc Semi-Ensuite (Each with Private Vanity Area) with Upgraded Frameless Glass Shower. Upgraded Porcelain Tile Flooring Thru Foyer, Kitchen & Servery Area, Mud Room & Powder Room. Engineered Hdwd Flooring Thru Main & 2nd Levels. 10' Ceilings on Main Level / 9' on 2nd Level & Basement. Upgraded 8' Interior Doors on 2nd Level. Upgraded Floor Tiles, Shower Floor Tiles & Shower Systems in 2nd Level Baths. Generous Fully-Fenced Backyard is a Blank Canvas for Your Design & Landscaping Ideas! Fabulous Location on Quiet Crescent in Desirable Joshua Creek Community Just Minutes from Many Parks & Trails, Top-Rated Schools, Rec Centre, Restaurants, Shopping & Amenities, Plus Easy Hwy Access.

1079 John Laird Circle, Oakville

$2,999,000

5 Beds ⋅ 3 Baths ⋅ W13291708 MLS

Nestled in Southeast Oakville, this beautifully renovated heritage home on Palmer Avenue offers timeless character, modern comfort and an exceptional lifestyle on a premium south-facing lot. Thoughtfully updated while preserving its architectural charm, the residence is filled with natural light and enjoys seamless connections to its private outdoor living spaces. The expansive south-facing backyard is a true retreat, featuring two spacious decks that provide multiple areas for entertaining, and relaxing while overlooking the mature grounds. Inside, the home blends heritage elegance with contemporary functionality. The welcoming great room is anchored by rich plank flooring and a stunning Rumford fireplace, creating a warm and sophisticated atmosphere for everyday living. The kitchen showcases clean lines and timeless design, complemented by a practical rear pantry hallway offering exceptional storage and organization. Large principal living and dining rooms provide generous space for formal entertaining while maintaining a sense of comfort and flow throughout the main level. The upper level offers four bedrooms, including a primary suite that features a Rumford fireplace, walk-in closet and a five-piece ensuite and laundry room The additional large fifth bedroom is on the main floor providing flex space for guests or home office. The finished lower level extends the living space with versatile area ideal for recreation, fitness, media or play, ensuring ample room for every stage of family life. Recent mechanical updates provide peace of mind, including a new furnace, owned hot water tank and central air conditioning. Combining heritage character, thoughtful renovations and an exceptional location in one of Oakville's most established neighbourhoods, this distinguished property offers a rare opportunity to enjoy sophisticated family living just moments from the lake, top-ranked schools, parks, shopping and the vibrant amenities of downtown Oakville.

332 Palmer Avenue, Oakville

$2,799,000

5 Beds ⋅ 5 Baths ⋅ W13248446 MLS

A rare offering in Oakville's prestigious Bronte Creek community, this exceptional ravine estate offers over 5,000 sq t of refined living space with breathtaking views and complete backyard privacy. Designed for elevated living and entertaining, the home features a resort-inspired backyard with swimming pool, hot tub, professional putting green, and a dedicated outdoor culinary station anchored by a high-end DCS dual fuel grill and Kamado Joe smoker - everything you''d leave for the cottage, right here in Oakville. Elegant principal rooms, hardwood flooring throughout the main living areas, and a designer chef's kitchen equipped with premium Wolf & Sub-Zero appliances complete the main floor. The professionally finished lower level delivers a true luxury lifestyle experience with a custom home theatre, private gym, sauna, and expansive recreation space. Ideally located near top-rated schools, scenic trails, parks, shopping, and major highways.

3447 Liptay Avenue, Oakville

$2,619,900

5 Beds ⋅ 5 Baths ⋅ W13242662 MLS

Welcome to 2470 Applewood Drive, a custom built luxury home positioned on a quiet court in the heart of Bronte. Backing ontoApplewood Park & surrounded by beautiful custom homes, this exceptional 5 bedroom, 4+1 bathroom residence offers over3,200 sq ft of living space plus a finished walk up basement, just steps from Bronte Village, the lake, waterfront trails, restaurants& cafés. A dramatic 21 ft foyer sets the tone, while 9 ft ceilings on both levels, extensive custom trimwork, hardwood floors on themain & second levels & natural light create an elegant yet welcoming atmosphere. Designed for everyday living & entertaining,the gourmet kitchen features a large centre island, double wide Electrolux fridge, 6 burner Dacor gas range, 2 sinks, abundantcabinetry & eat in area. The kitchen flows into the dining area & inviting living room with gas fireplace, custom built-ins & astunning picture window overlooking the backyard. A private home office, powder room, laundry room & inside access to the2-car garage complete the main level. Upstairs, the impressive primary retreat features a private balcony, oversized walk-incloset & spa-like 5 piece ensuite with heated floors, double sinks, soaker tub & glass shower. A second bedroom enjoys its ownensuite & walk-in closet, while two additional bedrooms share a Jack & Jill bathroom. The finished walk up basement addsexceptional versatility with large windows, a spacious recreation area, bedroom & 3 piece bathroom. Outside, enjoy a large backdeck overlooking a private backyard framed by trees & green space, creating a peaceful setting ideal for entertaining, relaxing &family gatherings. Adding to the home's appeal is a private neighbourhood park & seasonal community ice rink that bringneighbours together year round, creating a sense of community that is increasingly rare to find. Complete with an EV charger,2-car garage & an unbeatable location, this is a rare opportunity to enjoy the very best of Bronte living.

2470 Applewood Drive, Oakville

$2,690,000

6 Beds ⋅ 5 Baths ⋅ W13241930 MLS

A Rare Opportunity To Own A Custom-Built Luxury Residence In One Of Oakville's Most Prestigious Communities. Thoughtfully Designed From Top To Bottom With Exceptional Attention To Detail, This Stunning Home Showcases High-End Finishes, Sophisticated Craftsmanship, And Modern Elegance Throughout. Grand Entrance Welcomes You Into A Bright, Open-Concept Interior Featuring 10-Ft Ceilings, Wide-Plank Hardwood Floors, Designer Lighting, Custom Millwork, And Elegant Architectural Details. The Gourmet Chef's Kitchen Is Fully Appointed With Premium Built-In High End Appliances, Quartz Countertops, Gas Cooktop, Custom Cabinetry, And A Large Centre Island Seamlessly Connected To The Spacious Family Room With Fireplace - Perfect For Everyday Living And Entertaining. Luxurious Primary Retreat Offers A Spa-Like Ensuite And Expansive Walk-In Closet. Professionally Finished Lower Level Featuring 2 Additional Bedrooms, Stylish 3-Pc Bathroom, Large Recreation Area, Pot Lights Throughout, And Walk-Up Access To A Beautifully Landscaped Backyard Is Ready For Family Getting Together And Unwinding. Truly A Turnkey Custom-Built Home Offering Luxury Living In An Exceptional Oakville Location Close To Top Schools, Parks, Shopping, And Major Highways.

584 Weynway Court, Oakville

$4,977,825

W13239710 MLS

Exceptional opportunity for an owner occupier to acquire a highly visible, ground floor office condominium with prominent exposure to the QEW. The property offers abundant on-site parking and the unit is move-in-ready with quality finishes throughout. The building is well-maintained with only a handful of professional tenants, creating a quiet and functional working environment.

2660 Sherwood Heights Drive Unit 101, 102 & 103, Oakville

$4,350,000

4 Beds ⋅ 6 Baths ⋅ W13233446 MLS

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

$2,750,000

6 Beds ⋅ 4 Baths ⋅ W13223086 MLS

Location! Location! Welcome to 1319 Greeneagle Drive nestled in the sought after Gated community of Fairway Hills. Quiet cul-de-sac plus granted access to 11 acres of meticulously maintained grounds. Backing onto the 5th fairway offering breathtaking views as soon as you walk in. This spectacular family home has been extensively renovated with well over 300K spent by the current owners. Painted throughout in crisp designer white, smooth ceilings, over 170 pot lights, updated 200amp panel, new shingles, skylight + insulation, stone driveway and walkway, commercial grade extensive home automation system with security/smart locks, EV ready and smart closet designs. The lower level has been professionally finished with a rec room, 5th bedroom, full washroom, gym and a fantastic pantry/storage room. The primary suite has been transformed to create his and hers closets and a spa- like ensuite with heated floors, glass curb less shower and soaker tub. Entertainers backyard with large deck and heated in ground pool. Close to top rated schools, hiking in the 16 mile trail system, shopping and highway access.Move in and enjoy!

1319 Greeneagle Drive, Oakville

$2,610,000

4 Beds ⋅ 4 Baths ⋅ W13220932 MLS

Set on one of South Oakville's most prestigious and tranquil streets, this remarkable 100 x 146 ft estate lot offers an exceptional opportunity just moments from the shores of Lake Ontario. This well-maintained 4-bedroom, 4-bathroom residence is move-in ready, providing the flexibility to enjoy as is, renovate over time, or design and build your custom dream home. Inside, a welcoming foyer with wood stairs and elegant spindles sets a warm and refined tone. The spacious living room features a cozy fireplace, creating the perfect setting for relaxed evenings, while the separate dining room is ideal for hosting family gatherings and formal entertaining. The well-appointed kitchen offers stainless steel appliances, generous cabinetry, and ample counter space, seamlessly flowing into a bright, sun-filled sunroom with oversized windows. This versatile space an easily function as a lounge, home office, or additional family room, all while overlooking the beautifully private backyard. Step outside to your own backyard retreat complete with an in-ground pool, mature landscaping, and expansive green space-perfect for summer entertaining or quiet relaxation. A double-car garage and ample driveway parking add everyday convenience. Surrounded by custom multi-million-dollar estates, this property offers a rare combination of generous land, privacy, and outstanding future potential. An extraordinary opportunity to secure a premier lot in one of Oakville's most coveted neighbourhoods. Truly a property to see and appreciate. **Some pictures are virtually staged**.

145 Wolfdale Avenue, Oakville

$2,998,000

5 Beds ⋅ 4 Baths ⋅ W13215172 MLS

MUSKOKA-LIKE SETTING BACKING ONTO A RAVINE! LUXURY LIVING IN AN EXCLUSIVE ENCLAVE! MAIN FLOOR PRIMARY RETREAT! PROFESSIONALLY FINISHED WALKOUT LOWER LEVEL! Welcome to 1227 Riverbank Way, an exceptional residence in prestigious Valleyview Estates, tucked away at the end of an extremely private cul-de-sac. Upon arrival, you'll be captivated by the striking stone and stucco exterior, natural stone driveway, majestic trees, and lush landscaping. The centrepiece of the main level is the dramatic living room featuring a soaring 15'8 vaulted ceiling with decorative beams and a corner gas fireplace. A chef-inspired Downsview Kitchen with custom cabinetry, granite countertops, designer backsplash, premium stainless steel appliances, centre island, breakfast area, and walkout to the composite deck is ideal for effortless indoor/outdoor living. The rare main floor primary retreat offers a private balcony, vaulted ceiling, gas fireplace, walk-in closet, and spa-inspired five-piece ensuite with double sinks, vanity area, and luxurious soaker tub. Two additional bedrooms and a four-piece bathroom with skylight are located on the upper level. Professionally finished in 2018, the walkout lower level extends the living space even further with an oversized recreation/games area, two bedrooms, three-piece bathroom, and family room with patio access - ideal for multi-generational living. Notable updates include furnace and central air (2023), hardwood flooring throughout the upper level (2018), shingles (2018), and epoxy garage floors (2023). The tranquil backyard oasis showcases an expansive composite deck, natural stone patios and steps, stone benches, extensive river rock, landscape lighting, and the ultimate in privacy. This one-of-a-kind setting is surrounded by an extensive trail network along Sixteen Mile Creek, Lions Valley Park, forests, and greenspace, offering an unparalleled blend of luxury, nature, elegance, and lifestyle. (certain images have been virtually staged)

1227 Riverbank Way, 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

$3,649,000

5 Beds ⋅ 5 Baths ⋅ W13163910 MLS

Step into this newly constructed custom residence which showcases bespoke built-in cabinetry fine craftsmanship. Stately nine-foot ceilings on the first and second floors from the wood flooring to the large scale windows you will sense refinement. Cozy in floor heating throughout the basement and all stone floors on the main and second floor includes a decadent heated garage floor, meaning no need to bundle up to access the garage making it a functional space of the home. The property is consistent with creature comforts featuring dedicated upper and lower hvac systems, circulating instant hot water throughout, and three gas fireplaces. Included is a comprehensive security system with cameras. The exterior façade combines elegant stone elements with stunning composite wood features, oversized front landing, 4 season inviting back deck with it's own gas fireplace. Landscaping includes lighting with the addition of integrated driveway lighting to guide your way home. Luxury Certified.

540 Patricia Drive, Oakville

$4,498,000

6 Beds ⋅ 7 Baths ⋅ W13162726 MLS

Set on a deep pool-sized lot in prestigious South Oakville, this custom-built estate offers over 8,500 SF of meticulously finished living space. A dramatic slab feature wall & oversized entry door make a striking first impression, introducing soaring ceilings, wide-plank oak flooring, architectural detailing & expansive windows that seamlessly connect indoor & outdoor living. The designer kitchen is a chef's dream, featuring state-of-the-art B/I appliances, an oversized island, quartz & natural wood surfaces, custom cabinetry, a full prep pantry, dedicated servery, & accordion windows that open directly to the backyard for effortless entertaining. Sun-filled principal rooms flow into a stunning family room anchored by a statement fireplace wall & a W/O to a covered rear portico, which includes its own fireplace, lounge, & dining areas overlooking the pool-ready backyard. A spectacular 22-ft office/library creates the ideal work-from-home setting. Upstairs, the luxurious primary retreat offers a fireplace, custom walk-in closet & spa-inspired ensuite w/ heated floors & a freestanding tub. Generous secondary bedrooms feature ensuite/semi-ensuite access, while the third-floor loft serves as a versatile guest retreat, executive lounge, studio, or additional bedroom w/ a wet bar, W/I closet & private ensuite. Recently completed, the lower level delivers a true lifestyle experience w/ multiple entertainment lounges, a designer wet bar/kitchenette w/ W/O access, a theatre/games room, sauna, wine cellar, guest suite, heated floors throughout & a spa-inspired bath w/ a double rainfall shower. Modern luxury meets everyday comfort w/ a newly installed elevator services all levels, multiple fireplaces, B/I speakers, smart home systems, EV charging rough-in, pet washing station, landscaped grounds & walkouts to multiple private decks. Ideally located near top-rated schools, boutique shopping, private clubs, Lake Ontario, Bronte Harbour & convenient access to the QEW & Hwy 403.

584 Fourth Line, Oakville

$3,199,000

2 Beds ⋅ 2 Baths ⋅ W13158074 MLS ⋅ The Randall Residences BLDG.

Welcome to one of Downtown Oakville's most celebrated residential addresses, imagined and brought to life by an exceptional local team, the internationally acclaimed luxury designer whose signature detailing elevates this landmark building into a work of art. Together, they crafted a boutique residence that seamlessly blends sophistication, exclusivity, and enduring elegance. This expansive suite features grand principal rooms, soaring ceiling heights, and refined architectural proportions throughout. The Great Room and adjoining Kitchen/Dining Room provide an impressive setting for both relaxed living and elegant entertaining, while the formal Foyer and circular entry gallery create a memorable sense of arrival. The private primary wing offers a gracious Master Bedroom with Juliet balcony, ensuite bathroom, with walk through dressing room, delivering a true luxury retreat. A second bedroom is perfect for guests or extended family and is thoughtfully preceded by its own private vestibule, enhancing comfort and privacy. Additional conveniences include a separate Laundry Room, dedicated Storage Room, and a Powder Room that complements the home's generous flow. The building also features the renowned Sotto Sotto restaurant on the main level - a testament to the calibre of the address and a unique lifestyle benefit for residents. Steps to the lake, marina, shops, cafés, and cultural venues, this residence offers a rare blend of boutique luxury and walkable urban convenience. A distinguished opportunity to live in one of Oakville's landmark buildings.

300 Randall Street Unit 211, Oakville

$2,529,990

4 Beds ⋅ 5 Baths ⋅ W13158044 MLS

Brand new home under construction by Menkes. Prestigious "Bronte West" neighborhood in South Oakville. Exceptional opportunity to purchase directly through the builder's Sales Office. Projected closing date January 2027. Purchaser has opportunity to customize home. All offers on builder standard forms. Minimum 24 hour notice for showings. Listing agent must be on site for all showings. Showing must be confirmed with listing agent. No confirmation needed for Saturday and Sunday from 12pm-5pm.

166 Charles Bray Crescent, Oakville

$2,500,000

3 Beds ⋅ 2 Baths ⋅ W13154690 MLS

Prime Morrison location on a quiet, tree lined street just off Chartwell Road. Easy walk to St Mildred's and Linbrook Schools. Large .31 acre lot with rare 135' lot frontage to allow for maximum design flexibility. Spacious 3 Bedroom bungalow with double garage requires significant updating. Ideal location close to Downtown Oakville, parks, waterfront trails, top rated Public and Private Schools, Whole Foods Market, Longo's, Starbucks and GO Train.

1118 Melvin Avenue, Oakville

$2,999,900

4 Beds ⋅ 5 Baths ⋅ W13133516 MLS

Beautifully updated executive residence showcasing exceptional pride of ownership, thoughtful design, & a functional Upgrades ideal for family living and entertaining. Renovated kitchen, powder room, laundry room & garage entrance (2022), professionally painted throughout, new LED lighting on main & lower levels, new TOTO washlet toilets & Thermador appliances. Elegant main floor features maple hardwood flooring, crown moulding, pot lights, California shutters, custom built-ins, travertine foyer with medallion detail, bay window & pocket doors. Updated kitchen & breakfast area with quartz counters, oversized island, built-in microwave, 6-burner gas Stove with grill, b/i Thermador wall coffee station, charging station drawer. Custom Pantry with Beverage fridge, B/I Wine Rack and Storage Galore. Family feature cast stone fireplace and 21" ceiling, decorative columns, oversized windows & Swarovski chandelier in Dining Rm. Spacious primary suite with sitting area & Cast Stone fireplace, walk-in closet w/ organizer, and spa-inspired ensuite with rain shower, soaker tub, granite counters & California shutters. Additional bedrooms feature hardwood flooring, double closets, upgraded finishes, and Jack & Jill bath with granite counters & wood-looking tile flooring. Fully finished walkout basement with above-grade windows, recreation area, wet bar with double sink, gas fireplace with Wood mantle, built-in shelving, additional storage, cold cellar with automatic lighting, 3-piece bath. Mature landscaped backyard with private setting, outdoor bar seating, BBQ area, backyard WiFi router & shed added in 2022. Pool upgrades include new heater & Pentair Prowler (2022), liner (2023), filters & Intellichlor IC40 cell (2024). Additional updates include furnace & humidifier (2023), duct cleaning, serviced tankless hot water system, garage door hardware replaced, plus power washing, joint replacement & professional tree pruning completed in 2024.

203 Burloak Drive, Oakville

$3,299,000

3 Beds ⋅ 4 Baths ⋅ W13131034 MLS

This bespoke architecturally designed single-storey residence, created in the Contemporary Shed Style, combines refined architecture with exceptional functionality and craftsmanship. Designed for sophisticated entertaining and comfortable family living, the home features dramatic interior rooms, clean lines, and seamless indoor-outdoor connections. Principal living spaces and bedrooms are positioned to maximize privacy and natural light through expansive floor-to-ceiling windows overlooking landscaped gardens. A generous foyer introduces over 3,100 sq. ft. of refined single-level living. At the heart of the home, a striking four-sided wood-burning fireplace connects the formal living and dining areas. The gourmet kitchen is equipped with premium appliances, sky-lighting, custom cabinetry, walk-in pantry storage, and built-in serving functions, while oversized glass doors open directly to the gardens and outdoor entertaining spaces. The adjoining family room is filled with natural light from extensive glazing and skylights, complemented by wide plank white oak flooring, custom millwork, and cathedral tongue-and-groove willow ceilings. The private primary suite includes a spa-inspired ensuite, walk-in closet, and direct garden access. Two additional bedrooms feature oversized windows and double closets. The lower level offers excellent versatility with a recreation room, oversized laundry and craft area, workshop, cedar storage room, and wine storage. Completing the property are a cedar shake roof, cobblestone driveway, double carport, and oversized double garage with parking capacity for up to seven vehicles, delivering a rare blend of luxury, comfort, and practicality.

1168 Carey Road, Oakville

$2,949,000

5 Beds ⋅ 6 Baths ⋅ W13126692 MLS

An exceptional custom residence set on a commanding 150 x 75 ft lot in one of Southwest Oakville's most established and coveted neighbourhoods.Boasting over 6,300 square feet of total living space, this home offers 5 bedrooms and 6 bathrooms across three beautifully finished levels. This home showcases a rare and highly desirable layout with two primary suites - one on the main floor and a second grand retreat upstairs. Designed for elevated living and effortless entertaining, the home features refined principal rooms including formal living and dining areas, a private office, two powder rooms, and a full laundry suite. At its heart, the chef's kitchen impresses with rich cabinetry, granite countertops, marble flooring, a large centre island with seating, built-in stainless steel double wall ovens, gas cooktop, beverage fridge, and seamless flow into the family room with gas fireplace and custom built-ins. The main-floor primary suite offers privacy, an ensuite bath, and walk-in closet - ideal for multigenerational living or main-level convenience. Upstairs, the second primary retreat feels like a private sanctuary with its own fireplace, spa-inspired ensuite, and generous dressing space. Two additional bedrooms share a spacious 5-piece Jack & Jill bath, creating a functional family wing. The fully finished lower level enhances the lifestyle appeal with a large recreation lounge, wet bar, gym area, fifth bedroom, and full bath - perfect for guests or extended family. Outdoors, a private backyard oasis framed by mature landscaping features an inground pool, pergola-covered lounge, multiple hardscape entertaining areas, and a detached shed. A double garage with upgraded tiled flooring and private driveway complete this distinguished offering. Five bedrooms. Two primary suites. Three finished levels. A rare estate-sized lot in Southwest Oakville. 390 Seaton Drive - a home of scale, versatility, and enduring elegance.

390 Seaton Drive, Oakville

$3,800,000

5 Beds ⋅ 6 Baths ⋅ W13125176 MLS

Be the first to live in this custom built upgraded 5-bedroom, 6-washroom home in the sought-after Glen Abbey Encore community. Situated on a ravine-backed corner lot overlooking the Fourteen Mile Creek, this home offers over 4,440 sq ft above grade plus over 2,160 sq ft of unfinished basement space with walk-up access to a fully fenced backyard. Enjoy access to one of the area's largest parks featuring tennis & pickleball courts, basketball, soccer field, splash pad, playground, and trails. Featuring 11 ft ceilings on the main floor and 9 ft ceilings on the second floor and basement, upgraded 90" solid-core interior doors, hardwood flooring, coffered ceilings with crown moulding, pot lights, oversized windows, skylight above the staircase, open-riser staircase with stainless steel square spindles, elevated deck, dual furnaces & A/C systems, central vacuum including garage connection, smart lighting, exterior cameras, motorized blinds, and smart garage door openers with integrated cameras. All five bedrooms feature direct bathroom access, including three ensuites and a Jack & Jill bath. The primary suite offers ravine views, dual walk-in closets, and a spa-inspired ensuite with heated floors. The home also features two exterior entrances with covered porches, plus a main-floor office/den connected to a full bathroom. The custom Downsview Kitchen (one of Canada's premier luxury kitchen brands) features premium appliances including Sub-Zero column fridge/freezer and undercounter refrigerator, Wolf built-in oven, microwave & gas range, Miele built-in coffee system, and two Bosch dishwashers. Finished with quartz slab backsplash, double waterfall quartz island, large-format porcelain slab flooring, designer apron-front workstation sink, custom pull-out organizers, deep soft-close cabinetry, under-sink retractable central vacuum hose system, and a fully equipped servery with additional sink and second dishwasher connected to the breakfast area overlooking the ravine.

1283 Meadowside Path, Oakville

$3,400,000

6 Beds ⋅ 5 Baths ⋅ W13112236 MLS

Beautifully custom-built home showcasing luxury finishes throughout in one of the area's most prestigious and highly sought-after neighbourhoods. Boasting stunning curb appeal with a timeless stone exterior and an oversized driveway accommodating up to 6 vehicles, this exceptional residence blends elegance, comfort, and functionality. Designed with impeccable attention to detail, the home features elegant herringbone white oak flooring, soaring floor-to-ceiling windows in the family room, and a skylight that fills the main floor with an abundance of natural light. The chef-inspired kitchen offers quartz countertops, premium finishes, and ample space for both entertaining and everyday living. Beautiful custom drapery throughout the home adds warmth and sophistication to every space. The fully finished entertainer's basement is a true showstopper featuring a massive custom bar, rough-in completed for heated flooring, and a convenient separate entrance from the backyard offering endless possibilities for hosting, extended family, or future potential. The garage is thoughtfully designed with an additional rear garage door providing easy backyard access, perfect for storage, lawn equipment, and added convenience. Located in a prestigious and highly desirable neighbourhood close to top-rated schools, parks, shopping, and major amenities. Too many upgrades and features to mention - this is a must-see home that truly stands apart. Book your private viewing today!

431 Seaton Drive, Oakville

$4,999,000

5 Beds ⋅ 6 Baths ⋅ W13109494 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

$3,980,000

4 Beds ⋅ 4 Baths ⋅ W13109474 MLS

Set on a beautiful 100' x 136' lot in Prestigious Olde Oakville, this exceptional family home offers 4,752 sq ft of total living space of refined timeless design & impeccable craftsmanship all just a short stroll to Downtown Oakville, the lake, and some of Oakville's most sought-after schools. classic brick exterior, solid wood front door, and towering mature trees create a warm and elegant first impression. This home exudes an inviting aesthetic that feels made for family living and effortless entertaining.The kitchen features top-of-the-line appliances, two Miele dishwashers, dual walk-in pantries, water filtration system, three sinks including a coffee station/wet bar, and an oversized island that comfortably gathers family and friends for everything from casual breakfasts to holiday celebrations. The adjoining dining room is anchored by a charming wood-burning fireplace, while the spacious family room, also with a wood-burning fireplace, opens seamlessly to the private backyard, creating an ideal indoor-outdoor connection. Enjoy sunny south exposure, a sparkling saltwater swimming pool(liner/pump/heater 2024), Maibec deck with sleek glass railings, and a beautiful stone patio ideal for summer dining and lounging. Despite the impressive outdoor amenities, there remains abundant green space for children to play and the whole family to gather. The functional mudroom and sophisticated main floor den complete the thoughtfully designed main level. The second floor is equally impressive, highlighted by a luxurious primary retreat with its own gas fireplace, walk-in closet, custom built-in storage, and five-piece ensuite with heated flooring. Three additional generously sized bedrooms and a beautifully appointed full bathroom provide ample space for a growing family. Finished to the highest standards, this extraordinary residence offers the rare combination of timeless style, family-focused functionality, and an unbeatable Olde Oakville location. Welcome Home.

528 Michael Terrace, Oakville

$3,388,500

5 Beds ⋅ 7 Baths ⋅ W13107546 MLS

Situated On An Impressive 62' X 156' Lot In Prestigious West Oakville, This Exceptional Custom-Built Smart Home Offers Approx. 5,280 Sq Ft Of Luxurious Finished Living Space (3,400 Sq Ft Above Ground) With 5 Bedrooms, 5 Full Bathrooms And 2 Powder Rooms. Expertly Crafted With Premium Finishes And Impeccable Attention To Detail, This Residence Features 10' Main Floor Ceilings, 9' Upper & Lower Levels, Massive Velux Skylight, Oversized Windows, Crown Moulding, Wainscoting, Heated Floors, Built-In Speakers, Smart Home Automation And Multiple Gas Fireplaces. Designer Perola Kitchen With Custom Cabinetry, Glass Display Cabinets, Leathered Calcutta Granite Island, Caesarstone Counters, JennAir Built-In Appliances, 6-Burner Gas Cooktop With Pot Filler, Wine Fridge, Pantry And Designer Lighting. Stunning Great Room With Custom Built-Ins, Accent Lighting, Gas Fireplace And Expansive Rear Yard Views. Elegant Living & Dining Rooms With Imported Crystal Chandeliers, Hardwood Flooring And Custom Millwork. Main Floor Office Features Solid Wood French Doors, Built-In Shelving And CAT6 Wiring. Luxurious Primary Retreat With Vaulted Ceilings, Built-In Speakers, Large Picture Windows And Spa-Inspired Heated 5-Piece Ensuite Featuring Quartz Counters, Seamless Glass Shower, Soaker Tub, Makeup Vanity And Custom Walk-In Closet. All Additional Bedrooms Include Heated Ensuite Bathrooms And Custom Built-Ins. Professionally Finished Walk-Up Lower Level Includes Home Theatre, Games Room, Recreation Area, Wine Bar Rough-In, Heated Floors, Gas Fireplace, Additional Bedroom With Ensuite And Extensive LED Lighting. Exterior Features Include Natural Indiana Limestone Accents, Stucco Finish, Mahogany Doors, 6 Car Driveway, Pattern Concrete Walkways, Irrigation System, Security Cameras And Parking For 6 Vehicles. Integrated Smart Home Controls For Lighting, Security, Cameras, HVAC, Audio Complete This Truly One-Of-A-Kind Luxury Residence.

436 WILLIS Drive, Oakville

$3,599,999

5 Beds ⋅ 6 Baths ⋅ W13068536 MLS

Welcome to an exceptional custom-built luxury residence, where inspired architecture, (thoughtful design, and superior craftsmanship come together to create a home that is both elegant and functional. The grand foyer sets the tone, offering an impressive welcome into this truly distinguished home. Light, and architectural impact, the interior features a dramatic skylight that fills the home with natural light. The show-stopping 20 familyroom is highlighted by a stunning floor-to-ceiling porcelain fireplace, sophisticated yetinvitingatmosphere. The formal living room features 14' ceilings and expansive front-facing windows. The open-concept main level is enhanced by 10' ceilings, modern pot lighting, and |floor-to-ceiling windows, allowing sunlight to pour into every corner. Elegant wainscoting and custom wall panellin throughout the foyer, living room, family room, and staircase showcase the exceptional detail and craftsmanship found throughout the home. At the heart is a chef-inspired kitchen, designed for both everyday living. It features panel-ready Miele appliances, including ja refrigerator & appliances offering a seamless, built-in aesthetic. This well-planned kitchen providesanoutstanding layout, premium finishes, and a functional flow that opens directly to the backyard through sliding doors. Step outside to a covered rear patio, accessed from the kitchen, creating the perfect space for outdoor enjoyment. The fully fenced backyard ensures privacy, while the beautifully designed interlocked driveway and wrap-around hardscaping enhance curb appeal and durability, Car enthusiasts and active families will appreciate the extra-wide garage, designed to comfortably accommodate larger vehicles. A secondary rear garage door allows convenient access to the backyard-ideal for motorcycles or pets. The fully finished (basement continues the luxurious living experience, featuring large window wells for enhanced natural light, a stylish wet bar & full bath. You'll love it!

507 Wildwood Drive, Oakville

$3,888,000

4 Beds ⋅ 5 Baths ⋅ W13086416 MLS

Crafted by renowned architect Gren Weis and built by Hallmark Homes, this distinguished Morrison residence showcases timeless architecture and exceptional craftsmanship. Set on a beautifully landscaped 0.216 acre lot, the home offers approximately 5,500 sq.ft. of finished living space across three well-appointed levels. The main floor features quarter-sawn oak flooring, solid core doors, substantial millwork, 9" baseboards, and 9' ceilings, all enhanced by refined architectural detailing. A dramatic 13.5' coffered ceiling defines the family room, where a classic woodburning fireplace and rich cherry built-ins create an inviting setting. Expansive Kolbe windows flood the interior with natural light. The kitchen balances form and function, showcasing custom Andrew Moseley cabinetry, multi-toned granite countertops, tumbled marble backsplash, and premium appliances, including a Viking six-burner gas range. A generous 9' island with prep sink anchors the space, while the adjoining pantry and mudroom with built-ins and direct garage access enhance everyday living. Upstairs, the primary suite offers a private retreat with a walkout to sun deck, walk-in closet, and a luxurious limestone ensuite featuring heated flooring, Bain Ultra air tub, and oversized rain shower. Two additional bedrooms enjoy ensuite access, providing comfort and privacy for family or guests. The fully finished lower level features 9' ceilings and hydronic radiant heated floors, complete with a spacious recreation area, custom bar, fitness room with durable marmoleum flooring, and a guest bedroom. Exterior details include cedar shake siding, copper accents, UV-protected Kolbe windows, irrigation system, and a heated tandem garage. Located in one of Oakville's most established Morrison neighbourhoods, surrounded by matures trees and distinguished homes, this property presents a refined living experience in a coveted setting. (certain images have been digitally enhanced and virtually staged)

1049 Cedar Grove Boulevard, Oakville

$3,099,000

4 Beds ⋅ 3 Baths ⋅ W13082524 MLS

WONDERFUL FAMILY HOME IN A COVETED NEIGHBOURHOOD IN MORRISON WALKING DISTANCE TO GAIRLOCH GARDENS, THE LAKE AND SOME OF THE BEST SCHOOLS IN SOUTHEAST OAKVILLE. THIS LOVELY 2 STORY RED BRICK HOME WITH ALMOST 5000 SQ FEET OF LIVING SPACE OFFERS A CENTRE HALL PLAN WHICH IS FABULOUS FOR FAMILY LIVING AND ENTERTAINING. THE SEPARATE LIVING AND DINING ROOM ARE PERFECT FOR FORMAL ENTERTAINING. THE LIGHT FILLED OPEN CONCEPT KITCHEN HAS A TEN FOOT ISLAND WHICH IS A GREAT GATHERING SPOT FOR CASUAL GET TOGETHERS. THE FAMILY ROOM WITH A VAULTED CEILING AND FIREPLACE OFFERS A WALKOUT TO THE STUNNING LANDSCAPED GARDENS WITH A NEWLY RENOVATED IN-GROUND POOL. A MAIN FLOOR OFFICE WITH A WALL OF WINDOWS LOOKING OUT TO THE GARDENS MAKES WORKING AT HOME ENJOYABLE. THE BASEMENT IS VERY SPACIOUS WITH BOTH A REC ROOM, HOBBY ROOM/OFFICE AND SPECTACULAR WORKROOM. THIS MATURE PROPERTY WITH SOUTHERN EXPOSURE OFFERS PRIVACY WITH MATURE TREES AND PLENTY OF GREEN SPACE FOR THE KIDS TO PLAY. JUST MINUTES TO ALL THE MAIN HIGHWAYS AND THE GO FOR AN EASY COMMUTE.

1284 Cleaver Drive, Oakville

$3,116,125

2 Baths ⋅ W13081996 MLS

Industrail Space Available For Sale In Desirable Location Off North Service Road. Located At The West Side Of The Building, Plenty Of Free Unreserved Parking.Perfect For A Wide Range Of warehouse , storage , light industrial , Professional Uses Including Medical Office, Dental Clinic, Med Spa, Law Firm, Accounting Practice, Educational/Training Academy, And More.Flexible Purchase Options Available - Multiple Units Can Be Combined To Suit Your Needs, Ranging From 3,995 Sqft Up To 9,263 Sqft Strategically Located With Excellent Highway Access, This Is A Rare Opportunity To Establish Or Expand Your Business Presence In A High-Exposure, High-Traffic Location.Current drop ceiling height is 9 ft, with a clear ceiling height of 18 ft.

1075 North Service Road W Unit 5-9, Oakville

$2,698,000

5 Beds ⋅ 5 Baths ⋅ W13066506 MLS

This Architecturally Designed Home Comes Complete With 5 Bedrooms 3 Full Baths And 2 Half Baths A Custom Kitchen With Built In Appliances, Located In A Highly Sought After Tree Lined Quiet Street In South West Oakville This Quality Custom Built Home Offers Exceptional Decor High End Features And Over 5000 Sq Feet Of Finished Living Space. Great Room Open To Above, Fully Finished Basement, In-Ground 24X32 Salt Water Pool With Extensive Landscaping & Mature Gardens.

531 Jeanette Drive, Oakville

$4,750,000

6 Beds ⋅ 8 Baths ⋅ W13023762 MLS

Welcome to 417 Union Street, an exceptional modern home nestled in the heart of prestigious Old Oakville. Completed in 2023, this one-of-a-kind residence blends modern farmhouse inspiration with refined contemporary and traditional design elements, creating a home that is both striking and timeless. The modern farmhouse exterior showcases clean lines, black-framed windows, and a harmonious mix of materials, complemented by a covered porch, professionally landscaped front and back yards, and a stone six-car driveway. The backyard offers a private retreat with a deck, stone patio, and custom garden shed. Inside, the home is filled with natural light and defined by a modern, sleek interior. Wide-plank engineered hardwood flooring, custom ceilings with integrated LED lighting, and large-format matte tiles elevate the main living areas. The chef-inspired kitchen features quartz countertops and backsplash, an oversized centre island, built-in Bosch appliances, and a convenient adjoining servery. A tiered maple staircase with glass railings leads to the upper level, where skylights continue the home's bright and airy feel. The expansive primary suite spans over 700 square feet and offers two walk-in closets and a luxurious five-piece ensuite with double vanity, freestanding tub, and glass-enclosed rainfall shower. Three additional bedrooms each include their own custom three-piece ensuite with modern walk-in showers. The fully finished lower level adds outstanding versatility with a second kitchen, large recreation room, two additional bedrooms with ensuites, and a powder room. Additional highlights include an elevator servicing all three levels, 10-ft ceilings on the main and lower levels, pot lights, blackout blinds, built-in speakers, and a security system. Ideally located minutes from Lake Ontario, parks, trails, Oakville GO, the QEW, and top-ranked schools including Appleby College, this home delivers modern luxury, thoughtful design, and an exceptional lifestyle.

417 Union Street, 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

$3,850,000

4 Beds ⋅ 4 Baths ⋅ W13018186 MLS

It is rare to find a home that respects its history while boldly defining its future. Set within Oakville's prestigious West Harbour neighbourhood, 55 Chisholm Street is a study in modern heritage, where a century-old stone foundation anchors a home defined by thoughtful design and sustainable innovation. Superior craftsmanship and comfortable, functional spaces create a residence that is both considered and effortlessly livable. Every detail reflects a singular vision. The architecture bridges past and present with quiet confidence, pairing natural plaster walls and custom ironwork with a sculptural three-dimensional stairwell and a professional Valcucine kitchen outfitted with integrated Miele appliances. A striking soapstone fireplace grounds the main living area, while open-concept spaces extend toward landscaped gardens, creating a seamless connection between indoors and out. Its intelligence is expressed through restraint. Geothermal heating, energy-recovery ventilation, and rainwater harvesting are fully integrated, supporting a high level of performance without compromising design integrity. Upstairs, three well-appointed bedrooms and two bathrooms offer calm and privacy. The primary suite opens to a private terrace, while a treetop lookout captures elevated views across the neighbourhood canopy. The lower level includes a modern gym, cedar-lined wine cellar, and guest suite. Outside, the grounds continue the experience with a cedar sauna, outdoor shower, fire pit, and full outdoor kitchen. Steps from the lake and Downtown Oakville, this is a legacy property reimagined for the next century, offering a rare balance of architectural integrity, modern performance, and quiet, enduring livability.

55 Chisholm Street, Oakville

$3,998,900

4 Beds ⋅ 4 Baths ⋅ W12992608 MLS

Incredible offering in the Harbour district of Old Oakville one block from the lake and harbour and a short stroll to beautiful downtown Oakville. Over 3500SF of luxury living space. Beautiful custom build with open concept floor plan featuring soaring 10' ceilings and filled with light via wall-to wall windows and dramatic skylights. 3-floor elevator. Exceptionally high-end quality construction and attention to detail. Living Room with fireplace open to Kitchen with built-in SubZero & Wolf appliances, quartz counters, Butler's pantry with full height SubZero freezer and exceptional storage. Walk-out to a beautiful fully covered porch 27' x 11' with low maintenance composite decking. Beautiful Primary suite with south-facing lake view from Juliette Balcony, luxury Ensuite with heated floors, dual sinks, soaker tub and glass shower; Walk-in closet with built-in cabinetry. 2 further bedrooms with Juliette balconies with lake views. Main bath with heated floors and glass shower. Second floor Laundry. The ultimate lower level features high ceilings, radiant heated floors throughout, patio door walk-out to covered patio and access to the garden, large open concept Recreation Rm, full second Kitchen with high-end appliances, 4th Bedroom & guest bathroom; Cedar lined sauna with easy access to get outside to the hot tub. Triple Glazed windows throughout. Wired Security System. Irrigation System. The fenced garden features lush landscaping, large patio and gazebo for hot tub. Inside entry from oversized, 2-car garage with 12 ceilings can accommodate a car-lift.

36 Anderson Street, Oakville

$3,950,000

4 Beds ⋅ 4 Baths ⋅ W12991350 MLS

Private, elevated, and unlike anything else in Old Oakville - A true four-season outdoor retreat, your private playground for the outdoor enthusiast-where each day invites skating, paddling, kayaking, hiking, fishing, boating and cross-country skiing, alongside wildlife watching and refined al fresco dining, embracing nature in all its seasons. This lofted waterfront residence commands breathtaking views and unmatched privacy along the tranquil 16 Mile Creek. A testament to craftsmanship and design, this waterfront retreat boasts exclusive riparian rights and a private dock, inviting you to embrace the beauty of Oakville's scenic waterways year-round. .A meticulous 2016 renovation elevated this residence with rich hand-scraped oak floors, solid wood doors, custom millwork, and elegant tray ceilings. The sprawling 1,700 sq. ft. premium Wolf PVC deck includes a hot tub oasis, integrated fire table, and motorized awnings, leading to a dock with a kayak launch, swim ladder, and floating dock. Glass-encased staircases on helical piers deliver striking architectural presence and unbroken sight lines to the creek. Inside, sophistication defines every detail. Floor-to-ceiling windows in the living room frame stunning ravine views and dramatic sunsets, while a gas fireplace with a live-edge mantel adds warmth. The chef's kitchen impresses with a leathered Taj Mahal quartzite island, Wolf and Miele appliances, and an integrated Sub-Zero fridge. Heated floors run throughout, including in the spa-like primary ensuite with marble floors, a rain shower, and double vanity. The lower level offers a linear fireplace, built-in bar, and walkout to the deck. A concrete-lined storage room playfully known as the Bomb Shelter provides additional functionality. Blending natural beauty, refined design, and year-round outdoor living, this one-of-a-kind property is just steps to downtown Oakville and the GO Train offering luxury, serenity, and convenience in equal measure.

382 Trafalgar Road, Oakville

$3,000,000

5 Beds ⋅ 5 Baths ⋅ W12990848 MLS

Step into the pinnacle of modern elegance with this stunning custom-built executive home, nestled in the highly sought-after heart of Southeast Oakville. Offering a seamless blend of sophisticated design, premium finishes, and an abundance of natural light. From the moment you enter, you'll be captivated by the open and intelligently configured interior layout, soaring 10' floating ceilings with cove lighting, and floor-to-ceiling windows that fill the space with sunlight. Every detail has been meticulously crafted, from the European white oak engineered hardwood floors to the 8' solid core doors, flush trim, and hidden anchored glass railings that exude contemporary sophistication. The heart of the home is the designer kitchen, featuring an oversized island, 10' cabinetry, and top-of-the-line appliances, perfect for entertaining or enjoying quiet family moments. The main floor flows effortlessly into a spacious living area, complete with a gas fireplace, built-in surround sound, and motorized blinds for ultimate convenience. Upstairs, natural light continues to shine through skylights and oversized windows, illuminating four generously sized bedrooms, each with its own ensuite bathroom and custom-built walk-in closets. The bespoke laundry room, with floor-to-ceiling cabinetry, adds a touch of practicality and style. The finished basement offers additional living space, ideal for a home theatre, gym, or playroom, while the mono-stringer staircase and glass railings create a striking visual statement from top to bottom. This home is more than just a residence; it's a lifestyle. With its unparalleled craftsmanship, high-end finishes, and prime location in one of Oakville's most desirable neighbourhoods, this property is truly Luxury at Its Finest. Don't miss the opportunity to experience the intricate quality and modern elegance of this exceptional home.

1337 Waverly Avenue, Oakville

$2,698,000

5 Beds ⋅ 5 Baths ⋅ W12980110 MLS

Discover a lifestyle of refined comfort in the highly coveted Royal Oakville Club. This exquisite Fernbrook-built residence in South Oakville seamlessly blends grand architectural scale with the warmth of a true family home. Over 5000 finished square feet -every inch of this 4+1 bedroom home has been curated with an eye for detail.The heart of the home is a chef's dream: a gourmet upgraded Downsview kitchen featuring a sprawling centre island for five and a professional-grade Wolf and Sub-Zero appliance suite. Whether you are hosting formal gatherings under the coffered ceilings of the dining room or enjoying a quiet evening by the fire in the family room, the 10-foot ceilings and bespoke millwork create an atmosphere of airy sophistication.Retreat upstairs to find two magnificent primary suites, each serving as a private sanctuary with spa-inspired ensuites and custom wardrobe styling. Recently upgraded and landscaped rear yard with Unilock stone landscaping and a meticulous and thoughtfully designed garden. From the white-to-pink transition of the hydrangeas to the year-round privacy of the Norwegian Spruce, the backyard is an enchanting private oasis. Situated moments from Appleby College and the charming boutiques of downtown Oakville, this is more than a home-it is your retreat by the lake in a spectacularly convenient location.

343 Tudor Avenue, Oakville

$3,980,000

W12924914 MLS

ATTN: INVESTORS / DEVELOPERS... Extremely Rare Building Lot in Downtown Oakville That Is Site-Plan & Building permit ready!!! For 3 X 2600 Sq. Ft. Private Elevators To Each Suite, Private Expansive Terraces Of Approximately 450 Sq. Ft. For Outdoor Enjoyment. Owner And Guest Parking Available.

110 Chisholm Street, Oakville

$3,150,000

4 Beds ⋅ 3 Baths ⋅ W12922924 MLS

Spectacular opportunity in Southeast Oakville's prestigious Morrison Road district. Premium0.346-acre lot (102 x 148 ft) with desirable south exposure-ideal to move in, renovate,or build a custom home among multi-million dollar estates.Well-maintained 2-storey home offering approx. 2,549 sq ft with 4 bedrooms, 3 bathrooms, and adouble car garage. Updated throughout and suitable for immediate occupancy with futurepotential.Renovated kitchen features quartz countertops, subway tile backsplash, updated fixtures (2024),LG fridge (2024), and Samsung induction stove (2022), Heated Floors (Hot Water) in main floor family room and finished basement. Bright family room addition includes, skylight, and premium windows and doors. Muskoka room provides a peacefulspace overlooking the mature lot.Hardwood flooring and Napoleon fireplace (2024) in principal rooms. Finished basementincludes fireplace, pot lights, and large above-grade windows.Major updates: roof (2010-11), windows (2010-11), electrical panel (2010-11), furnace (2022),boiler (2022). Exterior features include Muskoka room, additional west facing side deck, Hardie board siding, composite deck (2022), irrigation system,landscaping, and exterior pot lights.Steps to Gairloch Gardens and Lake Ontario. Close to top-ranked schools and minutes toDowntown Oakville, highways, and GO.RL1-0 zoning permits approx. 30% lot coverage (~4,520 sq ft) and 29% residential floor area(~4,370 sq ft).

1268 Hillhurst Road, Oakville

$3,790,000

4 Beds ⋅ 4 Baths ⋅ W12899458 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. A selection of 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. Impressive detached w/47-foot frontage, 2836 sqft of finished space w/an additional 1,000+ sqft(approx) in the lower level left untouched. Curated:4 beds + 3.5 baths. Utility wing from garage, chef's kitchen w/w/in pantry, expansive breakfast+great room. 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.

338 MACDONALD Road, Oakville

$3,195,000

3 Beds ⋅ 5 Baths ⋅ W12899190 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. A selection of distinct models, each magnificently crafted, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and contemporary gathering spaces. A true exhibit of flawless design and impeccable taste. The Arlington; 3,677 sqft of finished space, 3 beds, 3 full baths + 2 half baths, this model includes 622 FIN sqft in the LL. A few optional layouts ground + upper. Garage w/interior access to mudroom, ground floor laundry, walk-in closet, full bath + family room w/French door to rear yard. A private elevator services all levels. Quality finishes are evident; with 10 ceilings on the main, 9 on the ground & upper levels. Large glazing throughout, glass sliders to both rear terraces & front terrace. Quality millwork & flooring choices. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Chefs kitchen w/top appliances, dedicated breakfast, overlooking great room. Primary retreat impresses with large dressing, private terrace & spa bath. No detail or comfort will be overlooked, with high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Expansive outdoor spaces; three terraces & a full rear yard. Perfectly positioned within a canopy of century old trees, a stones throw to the state-of-the-art Oakville Trafalgar Community Centre and a short walk to Oakvilles downtown core, harbour and lakeside parks. This is a landmark exclusive development in one of Canadas most exclusive communities. Only a handful of townhomes left. Full Tarion warranty. Occupation estimated summer 2026.

321 Helen Lawson Lane, 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

$2,900,000

W12888082 MLS

Free Standing Commercial Building For Sale in historic and vibrant Bronte Village, within walking distance of Bronte Harbour. Ground level drive-up retail, with four parking spaces in front and 10 additional spaces in rear. Wide range of permitted uses. Zoning is H1-MU1 with 55' frontage on Lakeshore Rd W. Lot depth is 197'. Second floor contains 4 residential apartment units with parking for each in rear.

2307 - 2309 Lakeshore Road W, Oakville

$3,399,999

4 Beds ⋅ 5 Baths ⋅ W12878342 MLS

Warm, serene, and inviting, this English farmhouse-inspired residence sits on an expansive 0.42-acre corner lot, offering a rare blend of character, privacy, and natural beauty. The impressive frontage and side yard create a true estate-like presence, with generous outdoor space on all sides of the home. Inside, a double-height foyer, gleaming hardwood floors, and an airy sense of volume set the tone for the rest of the residence. To one side, an intimate living room provides a refined setting for quiet conversation or reading, while on the other, a substantial main-floor study with rich architectural details is ideal as a home office, library, or music room. Beyond these formal spaces, the home opens into a relaxed, open-concept layout designed for modern living and effortless entertaining. A sunken family room anchors the informal wing and flows into a welcoming dining room highlighted by a wood-burning fireplace that adds warmth and ambiance to gatherings with family and friends. At the heart of the home, the kitchen is bathed in natural light from overhead skylights. Stainless steel appliances, sleek countertops, generous cabinetry, and warm accents create a space that is both highly functional and inviting. Thoughtfully designed with cozy elegance, the home offers four bedrooms, three full bathrooms, and two half bathrooms. Large windows frame views of manicured corner-lot gardens and offer peek-a-boo glimpses of the lake, giving the property a tranquil, retreat-like feel. Outside, beautifully landscaped grounds wrap the home with multiple outdoor zones, including a hot tub, Scandinavian-style sauna, and enclosed swimming pool, creating a resort-like experience in your own backyard. This exceptional property offers convenient access to major highways, lakeside walking trails, and a highly regarded school catchment area, delivering an elevated lifestyle in one of Oakville's most sought-after neighbourhoods.

24 Birkbank Drive, Oakville

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