Oakville Real Estate | Oakville Single Family Homes for Sale

COMPLETELY REDESIGNED IN 2015 WITH A 600 SQUARE FOOT ADDITION! Welcome to 269 Sunray Road, a beautifully renovated home nestled on a quiet, family-friendly street in sought-after Bronte! This exceptional four-bedroom family residence was thoughtfully redesigned in 2015, featuring a spacious 600 square foot primary retreat addition above the garage, complete with an electric fireplace, walk-in closet, and spa-inspired four-piece ensuite. Designed for modern living, the open concept main level offers an ideal floor plan with a bright, centrally located kitchen showcasing a large centre island, quartz countertops, stainless steel appliances, ample cabinetry, and plenty of space for family and friends to gather. Stunning PurParket hardwood flooring (made in Canada) flows throughout the main level (2026) and upper level (2015), adding warmth and continuity. Quality upgrades include custom cabinetry from Precision Cabinetry, spray foam insulation throughout, updated electrical, hardwired fire and carbon monoxide detectors, a 200 amp breaker panel, as well as a furnace and roof (2015). Step outside to your own private backyard oasis, featuring an inground saltwater 16' x 30' pool and hot tub (both installed in 2018) - a perfect space for relaxation, hosting family barbecues, and entertaining guests. Ideally located within walking distance of Eastview Public School, parks, Queen Elizabeth Park Community and Cultural Centre, and South Oakville Centre (Hopedale Mall). Enjoy close proximity to vibrant Bronte Village and the lake, offering the very best of lakeside living. A rare opportunity to experience refined living on one of South Oakville's most coveted streets. (certain images have been digitally enhanced)

269 Sunray Road, Oakville

$1,929,900

5 Beds ⋅ 5 Baths ⋅ W13067736 MLS

Premium 50-ft lot backing onto greenspace in highly sought-after Westmount! Exceptional family home offering over 3,300 sq ft of bright, functional living space with 4+1 bedrooms and 5 bathrooms. Desirable layout features spacious principal rooms, main floor office, oversized family room, and open-concept kitchen with breakfast area overlooking private backyard. Expansive primary retreat with walk-in closet and ensuite. Finished basement with additional bedroom, bath, and recreation area provides ideal space for extended family, guests, or entertaining. Enjoy privacy with no rear neighbours. Close to top-rated schools, parks, trails, hospital, shopping, and major highways. Rare opportunity in one of Oakville's premier family communities.

2481 Whistling Springs Crescent, 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

$1,970,000

4 Beds ⋅ 5 Baths ⋅ W13060630 MLS

4-Bedroom Detached Corner Residence In The Prestigious Glen Abbey Encore Community, Built By Lindvest In 2022. Offering 4,171 Sq Ft Total Area / 3,897 Sq Ft Of Finished Living Space (As Per MPAC). Designed With 10 Ft Ceilings On The Main Level And 9 Ft Ceilings On The Upper And Lower Levels. Hardwood Flooring Throughout Main And Second Floors, Complemented By Porcelain Tiles And High-Quality Luxury Vinyl Flooring In The Finished Basement. Chef-Inspired Kitchen Featuring Premium Appliances. Open-Concept Family Room With Fireplace And Main Floor Den Ideal For A Home Office. Well-Designed Layout With Two Bedrooms Offering Private Ensuites And Two Additional Bedrooms Connected By A Jack & Jill Bathroom. Primary Retreat Features A Spa-Inspired Ensuite With Freestanding Tub And Frameless Glass Shower, Along With Generous Walk-In Closets. Professionally Finished Basement With 9 Ft Ceilings, Full Bathroom, And Oversized 36" Windows Providing Abundant Natural Light. Located Steps To Saw Whet Park With Tennis, Pickleball, Soccer Fields, And Playground, And Surrounded By Trails And Green Space Near Fourteen Mile Creek. Photos Virtually Staged.

2395 Saw Whet Boulevard, Oakville

$1,998,000

5 Beds ⋅ 4 Baths ⋅ W13056138 MLS

Great Family Home in a Fantastic Location! Discover this charming family home situated between two top-rated schools in Joshua Creek: St. Marguerite and Iroquois Ridge. Convenience is at your doorstep, with just a few minutes walk in either direction. This property features a rare wrap-around front porch, complemented by a beautiful stone garden. The front-facing room is perfect for a home office or a quiet retreat. The inviting open kitchen and family room boast a cozy gas fireplace and provide easy access to the backyard, making it an ideal space for entertaining. Highlights include: 9 ft ceilings and durable hardwood and tile flooring throughout for easy maintenance. A spacious basement equipped with a second gas fireplace, an extra bedroom, a full bathroom, and a newer laundry suite plus tons of storage space. A 2-car garage with inside entry, along with a side entrance from the mudroom.This home blends comfort, convenience, and style. Enjoy nearby parks, recreational centers, dining, shopping, and easy access to the highway. Don't miss your chance to make this beautiful house your new home!

1259 GLENASHTON Drive, Oakville

$6,459,000

5 Beds ⋅ 8 Baths ⋅ W13050914 MLS

This Incredibly Keeren Designed Home Built In 2022! Located In Prestigious Eastlake Neighbourhood. This Home Boasts Approx.6300sf Luxury Living Space! Featuring Top-Notch Architectural Refinements With 4+1 Bdrms, 8 Baths (6 Full, 2 Half). Exterior Facade And Walk-up Area Built With Indiana Stone From The United States, Pella Windows And Doors, 71/2"*3/4 Grandeur White Oak Colour Engineered Hardwood Floor Through Out.The First Floor Boasts 10' Ceiling, A Double-Height Entry W/A Chandelier Lift/Down/W/A Skylight. Spacious Main Flr Office Perfect For Working From Home. The Great Rm Area Includes A Cozy Gas Fireplace, Breathtaking Views Of the Stunning Backyard Pool. Kitchen Equipped With B/I High-end Wolf Gas Stove & Hood, B/I Miele 30'' Fridge, Freezer, Oven & Micro, 2 B/I Asko Dishwashers And 24" Marvel Wine Fridge. A Lg 60* 91 Centre Island, Marble Calacatta Porceline Countertop And Backsplash, Ample Upper & Lower Cabinetry Space.The Interior Showcases Detailed Trim Work, Plaster Crown Molding, A Motorized Blinds System On Main Flr And Master Bdrm, Heated Floors In The Basement And All Ensuite Upstairs. Massive Windows Flooding Every Space With Light. The 2nd Floor Offers 4 Luxurious Bdrms, Each With Its Own Ensuite And W.I.C. Primary Bdrm W/A Lg Dress Rm W/A Skylight & Elegant 5pc Ensuite. The Residence Is Further Equipped With 2 Carrier Air Conditioning Units and 2 Furnaces W/Humidifiers. The Basement Includes A Guest Bdrm W/Ensuite, Rec, Home Theatre, Gym & Glass-enclosed Wine Rm. Designed Landscaping At Front & Backyard. The Fully Fenced Rear Yard Is A True Oasis W/Salterwater Pool W/Waterfall, An Outdoor Covered Porch W/Stone Gas Fireplace & BBQ Area. Irrigation System, Security System W/HD Outdoor Cameras, An Indoor Sound System And Google Home Automation. Six Routers Allow Network Signal Transmitted Within Entire House. HWT Owned. Walking Distance To Town, Parks & The Lake. OT High School, Maple Grove, Ej James, St. Mildreds, Linbrook, Appleby, Maclachlan.

172 Burgundy Drive, Oakville

$1,689,990

4 Beds ⋅ 5 Baths ⋅ W13042670 MLS

Beautiful Valery home with 4 + 1 bedrooms, 5 bathrooms, offering approx. 3400 sq ft including professionally finished basement by the builder. Extensive upgrades including, engineered hardwood flooring, plaster Crown Moulding throughout main Fl and upper hallway, 10 & 9 ceilings, great room with fireplace, upgraded tiles on main fl. surround system on main Fl, beautiful kitchen with quartz counters, quartz backsplash, breakfast counter and top of the line Jenn-Air SS appliances, gas stove and gas oven.. Enlarged basement windows & rough-in for wet bar. 2nd floor laundry room. All upstairs bedrooms have ensuite bathrooms & the primary bedroom with luxe 5-piece ensuite soaker tub & glass shower. Close to schools, hospital Hwy, parks and lots more. Incredible value here! 10+! **EXTRAS** Some Furniture can be included please ask LA.

95 Viva Gardens, Oakville

$23,980,000

5 Beds ⋅ 8 Baths ⋅ W13030806 MLS

Welcome to 489 Lakeshore Road East, a truly exceptional estate crafted by the renowned Ferris Rafauli, nestled in the prestigious enclave of southeast Oakville along the serene shores of Lake Ontario. This rare one-acre property boasts a remarkable 18,000+ square foot steel-frame home, meticulously designed to showcase unparalleled craftsmanship and timeless elegance. Every detail of this exquisite residence speaks to a dedication to luxury living, from its concrete structure to its five bedrooms and eight baths, eight fireplaces, three kitchens, and elevator for seamless access to all levels. Indulge in the ultimate relaxation with amenities such as an indoor pool, built-in spa, dry sauna, and cabana with a full kitchen. The property also features a four-car garage, 600-amp electrical service, in-floor heating, and cutting-edge building operation systems, all complemented by award-winning landscaping that surrounds this magnificent estate. For the discerning buyer seeking the epitome of luxury living, 489 Lakeshore Road East offers an unparalleled opportunity to experience a lifestyle of opulence and refinement.

489 Lakeshore 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

$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

$2,399,800

4 Beds ⋅ 3 Baths ⋅ W13006060 MLS

Rare ravine-backed bungalow on an exceptional 27,000 sq ft lot in Old Oakville, backing onto a protected preserve and creek. Thoughtfully renovated and move-in ready with bright principal rooms and beautiful natural views. All renovations and features are detailed in the attached feature sheet. Ideal to Move in now or create your dream estate in one of Oakville's most prestigious and picturesque neighbourhoods. Feels like cottage country, yet steps to Kerr Village, Downtown Oakville, Tannery Park, top schools, the lake, and the GO Station.

327 River Side Drive, 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

$1,599,000

2 Beds ⋅ 2 Baths ⋅ W12986568 MLS

Build your dream home! Nestled on a premium 60 x 136 ft lot in South-east Oakville's prestigious Morrison neighbourhood, this charming 2 bedroom all brick bungalow (formerly 3 bedroom) is a property that rarely comes to market. Zoned RL2-0, the generous frontage and depth offer an outstanding build envelope - ideal for a custom home or a significant addition and renovation. Thoughtfully maintained throughout, the home offers a warm and functional layout with 2 bedrooms, 2 bathrooms, and a beautifully finished basement complete with a custom fireplace, bar, and games area, along with a dedicated office space. Step outside to the covered back deck where an outdoor fireplace sets the tone for relaxed evenings surrounded by nature - the kind of setting that makes it easy to forget you're minutes from everything. The landscaping and mature trees have been carefully tended over many years, with a lush treed rear boundary that adds real privacy and seclusion to the property. Situated on a quiet, tree-lined street surrounded by impressive custom builds, the location offers the very best of South-east Oakville living. Top-ranked schools including St. Mildred's Lightbourn and Linbrook are within walking distance, while the Oakville GO Station, the waterfront, downtown Oakville's shops and restaurants, and convenient highway access are all just minutes away. Whether your vision is a brand new custom home or a thoughtful renovation and addition, this is the property that makes it possible - on one of South-east Oakville's most sought-after streets.

1051 Melvin Avenue, Oakville

$2,449,000

4 Beds ⋅ 4 Baths ⋅ W12949344 MLS

MOVE BEYOND THE STANDARD in Oakville's prestigious Joshua Creek. This refined 4,200+ SF residential asset is a masterclass in architectural volume and intentional flow. Engineered for grand-scale entertaining, the residence opens to a soaring double-height foyer and a curved staircase, leading into a light-filled living space anchored by a sophisticated two-sided gas fireplace. The formal dining room features custom coffered ceilings, while the chef-inspired kitchen and breakfast room offer a seamless transition to the private porch and rear grounds. STRATEGIC LAYOUT & DESIGN - A secondary staircase provides direct lower-level access, complemented by a dedicated mudroom/laundry and abundant storage solutions. The upper gallery leads to a primary suite designed as a private sanctuary, featuring a spa-caliber ensuite and dual walk-in closets. Three additional oversized bedrooms offer unparalleled versatility, including a semi-ensuite and a private ensuite with a custom window bench. PREMIER LOCATION & ACCESS - Positioned within the catchment of Ontario's top-tier institutions-Joshua Creek Elementary and Iroquois Ridge SS-this property offers proximity to elite golf clubs, tranquil trail systems, and rapid transit/highway corridors (403/QEW/407). Experience the intersection of luxury and logic. Move Beyond the Search.

2238 Lyndhurst Drive, 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

$7,900,000

6 Beds ⋅ 8 Baths ⋅ W12919550 MLS

Located on the prestigious private lane of Lambert Common this masterful 8300 square foot plus home includes a seamless 2024 addition from the original 7 year old build. This custom residential design stuns with grand proportions and meticulous detail. All three levels feature 10-foot ceilings defining the home by its impressive rooms and an atmosphere of space and luxury. The entrance is both welcoming and breathtaking with it's incredible moldings and crystal chandelier casting diamond glints across the foyer flanked by the living and dining rooms. Stepping through to the back of the house, you will enjoy panoramic views of wall to wall glass overlooking the two heated patios. The culinary wing is divided into two distinct zones for the ultimate hosting experience: The Showcase Kitchen: A visual centerpiece featuring a dramatic backlit stone wall that serves as a piece of living art. A 14-foot island, elegantly underlit to create a feeling of light providing sophisticated seating for six to enjoy the stunning kitchen. The Prep Kitchen: Positioned discreetly at the back of the main floor, this secondary kitchen allows for preparation to remain out of sight, ensuring the primary living space remains pristine. The home boasts five bedrooms with walk-in closets and ensuites. The Primary Suite is a dedicated sanctuary with his & hers walk-in closets, fireplace, and private bath, all oriented specifically to provide a serene, view of the lake, allowing the water to serve as a constant, tranquil backdrop. The upper level laundry room is spectacular an appliance package that includes a steam closet. The Entertainment & Wellness Lower Level Maintaining the same 10-foot ceiling height as the upper floors, and a destination unto itself. This level is fully equipped for a high-performance lifestyle, featuring and private glass enclosed gym, theatre room, open recreation room, secondary laundry suite & sixth bedroom with private office. This home is Luxury Certified.

15 LAMBERT Common, 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

$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

$1,920,000

6 Beds ⋅ 3 Baths ⋅ W12894154 MLS

Gorgeous Family Home on Prestigious Chartwell Road in Old OakvilleNestled on a prime 0.29-acre west-facing lot backing onto serene woodlands, this immaculate 4+2 bedroom residence is situated on the coveted "Street of Dreams" Chartwell Road in the heart of highly sought-after Old Oakville. Offering endless potential, this exceptional property is ideal for families looking to move in, renovate, or build their custom dream home in a prestigious neighbourhood.The beautifully maintained home features gleaming hardwood floors, spacious living, dining, family principal rooms, and a thoughtfully updated patio and deck perfect for outdoor entertaining. The finished basement, with a private separate entrance, includes a 2-bedroom in-law suite complete with a full kitchen and bathroom, offering incredible flexibility for multigenerational living or rental income.Enjoy unparalleled convenience with a short walk to Whole Foods, Longos, charming local restaurants, top-rated schools, and minutes to the GO Station and QEW. This is a rare opportunity to own a slice of Oakville's most desirable enclave where lifestyle, luxury, and location meet.

494 Chartwell Road, Oakville

$1,999,999

5 Beds ⋅ 4 Baths ⋅ W12876160 MLS

Welcome To This Unique, Custom-Built Home In Desirable East Oakville. Situated On A Premium, Treed Lot, This Home Features An Amazing Heated Sunroom With Massive Windows, Tile Floors, And A Stunning Entertainment Wall Including A Fireplace, Desk, And A Space For Your Wall-Mounted TV. Double Entry French Doors Lead To A Backyard Retreat Patio Area Equipped With An Outdoor Kitchen, Gazebo, Waterfall Feature, Garden Shed, And Ample Room For A Pool Or Hot Tub. Inside Features An Open Concept Main Floor Design With A Grand Kitchen, Built-In Appliances, Granite Countertops, Backsplash, Center Island, Pot Lights, And Large Windows. The Main Floor Bedroom Has Access To A Full 3-Piece Bathroom And Can Be Easily Converted To A Separate Formal Dining Room Or Office. The Space Also Includes Extensive Wall Trims And Hardwood Floors Throughout. The 2nd Floor Has 4 Additional Bedrooms And A Laundry Room. The Finished Basement Has A Possible Side Entrance And An Open Concept Layout With A Kitchen And 3-Piece Bath, Perfect For Large Family Gatherings, An In-Law Suite, Or Additional Income!

427 Pinegrove Road, Oakville

$6,999,900

6 Beds ⋅ 7 Baths ⋅ W12871004 MLS

Crafted as the personal residence of a renowned designer, this 5+1 bedroom, 10,000+ sq.ft. waterfront estate is a rare offering in one of Bronte's most coveted settings. While neighbouring homes were also designed by him, none compare to the scale, craftsmanship, and artistry dedicated to this residence-his own masterpiece. Expansive windows and soaring ceilings flood the home with natural light, framing breathtaking lake views on every level. Multiple balconies and terraces offer front-row views of sunrises, sunsets, and moonlit water-creating a seamless connection to nature from morning to night. Thoughtfully designed for both family living and elegant entertaining, the main level features grand principal rooms, multiple gas fireplaces, formal and informal living spaces, and a gourmet kitchen with walkout to the lakeside terrace. Each level offers outdoor retreats - private balconies off bedrooms, and expansive terraces perfect for gatherings. The upper level includes generously sized bedrooms, including a luxurious primary suite with private balcony, spa-like ensuite, and unobstructed views of the lake. A full lower level adds an additional bedroom, recreation spaces, gym, and walkout access. Set on a quiet street with a strong sense of community, this home offers a rare blend of privacy and connection. The saltwater pool, manicured grounds, and lakeside setting make every day feel like a peaceful escape. Minutes to Bronte Harbour, boutique shops, trails, parks, and top-rated schools-this residence is more than a home; it is a lifestyle on the water.

3206 Shoreline Drive, Oakville

$1,689,000

4 Beds ⋅ 5 Baths ⋅ W12869800 MLS

Discover this stunning home in a sought-after Oakville community, offering spacious living and modern convenience. Designed for comfortable living and entertaining, the home features a built-in security system and a basement equipped with a sound system-perfect for movie nights or gatherings. Located close to parks and green space, the property also benefits from a brand-new high school scheduled to open nearby in September 2026. An excellent opportunity to enjoy modern living in a growing, family-friendly neighbourhood.

132 Settlers Road E, Oakville

$3,600,000

5 Beds ⋅ 4 Baths ⋅ W12812288 MLS

Spectacular lakefront property could be your in-town cottage. Tucked away on quiet, mature-cul-de-sac with 93' frontage on Lake Ontario. This quality, custom built, one-owner home offers 4+1 Bedrooms, 3.5 Baths with over 2800SF above-grade + 1400 SF finished lower level is the perfect place to put your personal stamp on a 'not-too-big' forever home on the water. Architecturally designed with wall-to-wall windows overlooking the lake, solid brick construction with clay tile roofing, this home was built to last. 9' and 10' ceilings on the main floor. Oak hardwood floors throughout both levels. Entrance foyer with oak staircase. Beautiful Living Room with fabulous marble fireplace surround with gas insert open to Dining Room with wall to wall patio doors to the terrace with incredible lake views. Fabulous Kitchen/Breakfast Room is a blank canvas with the perfect space to install the waterfront Kitchen of your dreams. Walk-outs to both decks and open to the the Family Room with stunning marble fireplace with gas insert. The main floor features a mudroom with side entry and inside entry from full-sized two-car garage. The Primary suite features oversized windows and a walk-out to second floor balcony with outstanding lake views, luxury ensuite bathroom and walk-in closet. Two more Bedrooms overlook the lake with oversized windows. The front Bedroom opens to a bonus room above the garage which could be handy as a Den or quiet retreat. The Lower Level has excellent ceilings height, good windows and features one Bedroom, a 3-Piece Bathroom, Recreation Room, Den, Laundry Room, storage and more. Beautifully landscaped and maintained property fully fenced with wrought iron gate access to the lake. Cobblestone driveway accommodates 4 cars. Outstanding value on Lake Ontario. A must see!

3286 Shelburne Place, Oakville

$3,450,000

3 Beds ⋅ 3 Baths ⋅ W12778182 MLS

Attention Investors & Developers! Zoning approved for four luxury townhome units (RM1) with a total buildable gross floor area of 14,736 sq. ft. on a 0.24-acre lot (building permits not included). Features both surface and underground parking. Renderings available for review. Located in a prestigious and tranquil enclave in West Oakville, just south of Lakeshore. Steps from Bronte Heritage Waterfront Park, Bronte Boathouse, and Marina! An upgraded, move-in-ready home is currently on-site, perfect for living or renting. **EXTRAS** Includes stainless steel appliances: fridge, stove, built-in dishwasher; front-loading washer and dryer; light fixtures; window coverings; garage door opener; gazebo; garden shed; and greenhouse.

47 Nelson Street, Oakville

$1,149,000

3 Beds ⋅ 2 Baths ⋅ W12771592 MLS

NEW PRICE!! Charming and impeccably maintained split level home located in trendy Central Oakville. Versatile layout with 3 bedrooms, 2 bathrooms and finished recreational room. Steps away from great schools, shopping, highway access and a short walk to the lake and vibrant Kerr Street and Downtown Oakville. The fenced backyard adds privacy and usable outdoor space to enjoy barbques and family gatherings. Separate detached garage and shed/workshop frame the backyard. Move in and enjoy this cozy home now or have it serve as a blank canvas to create your personal family vision.

251 Elmwood Road, Oakville

$7,950,000

5 Beds ⋅ 8 Baths ⋅ W12702312 MLS

Welcome to 64 Brentwood Road, where a exquisitely crafted home masterfully blends timeless design and modern features. Located on one of the most coveted and prestigious streets and steps to the shoreline of Lake Ontario, this exceptional home is situated on an expansive 100 x162 lot and offers over 10,000 sq ft of luxurious living space. Designed by award winning architect Michael Pettes and built by renowned builders PCM, this elegant home offers the finest finishes throughout. The property is beautifully landscaped, providing a private and resort like outdoor oasis complete with a saltwater pool with cascading waterfall, perfect for summer relaxation as well as outdoor gourmet kitchen and wood burning fireplace for effortless entertaining as well as a outdoor bathroom for privacy for guests. Inside, indulge in a impeccably crafted and light filled living space with heated floors, designer light fixtures and finishes. The heart of the home is the gourmet kitchen with Wolf and Subzero appliances, with an additional servery and a spacious pantry. Upstairs the home boasts 4 generous bedrooms, each with their own ensuite for privacy and comfort for family and guests. The primary bedroom offers a relaxing retreat with spa like bathroom and large walk in closet with balcony and views of the manicured rear yard. A fully finished walk up basement offers a large recreation and games space with built-in bar, climate controlled wine cellar, home theatre, gym as well as a 5th bedroom/ nanny suite with ensuite bathroom. With a lavish stone exterior, a 3 car garage with additional lift, elevator and safe room, this charming home seamlessly combines elegance with luxury offering the best of both worlds. Whether enjoying the expansive interior, relaxing by the pool, or strolling to the lake, this home provides an unparalleled lifestyle in one of Oakville's most sought-after neighbourhoods.

64 Brentwood Road, Oakville

$1,799,000

4 Beds ⋅ 2 Baths ⋅ W12679326 MLS

An exceptional opportunity to build your dream home in one of Oakville's most prestigious and sought-after neighbourhoods. Set on a quiet, tree-lined 60 x 122 ft lot widening to 78 ft at the rear, this property offers a rare chance to design and build a custom home exceeding 3300 sq.ft.(above grade). The existing home is well maintained and fully livable, allowing you to move in or generate rental income while securing permits. Ideally Located just minutes from Lake Ontario, downtown Oakville, the GO Train, top-ranked schools, parks, and major highways, this address perfectly balances tranquility, convenience, and long-term value. Buyers or their representatives should verify all zoning and building details with the Town of Oakville's Planning and Building Department.

1169 Cynthia Lane, 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

$3,250,000

4 Beds ⋅ 3 Baths ⋅ W12419345 MLS

Nestled south of Lakeshore in the heart of Old Oakvilles historic district, this beautifully restored Georgian-style home, designed by Gren Weis, blends timeless character with modern updates. Steps from the lake, river, and vibrant Downtown, it offers an unmatched lifestyle location.The home boasts exceptional curb appeal with a flagstone path leading to a spacious foyer. Sun-filled interiors feature Farrow & Ball paint, new hardwood on the main level, preserved fir upstairs, smooth ceilings, and recessed LED lighting.The updated kitchen includes a large island, built-in appliances, and desk area. The dining room offers panelled walls, RH sconces, French doors to the garden, and plantation shutters. A charming living room features built-in bookcases, window seat, wood-burning fireplace, and walkouts to a sunroom overlooking the southwest garden and pool. A mudroom and stylish powder room complete the main floor.Upstairs are four bedrooms with ample closets and antique brass hardware. The primary suite offers custom built-ins and a renovated ensuite with heated Carrara marble floors and zero-threshold shower.The fully finished lower level (8 ceilings, slate flooring) adds living space with a media room, workout room, cedar closet, laundry, and storage. Updated mechanicals include a high-efficiency furnace, central AC, 100 AMP panel, irrigation. Cedar roof, new fencing, cobblestone driveway. Outside enjoy a private oasis with saltwater inground pool, brick patios, and landscaped gardens. Steps to the Lake, Oakville Club, Yacht Squadron, Library, Performing Arts Centre, Downtown, and top schools.

53 Thomas Street, Oakville

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