Refine Search
Map
Sort by
$2,399,000
5 Beds ⋅ 3 Baths ⋅ W13832032 MLS
South East Oakville Home Dream. Nestled on a premium, light-filled south-facing lot on Palmer Avenue, this beautifully updated heritage home seamlessly blends timeless architectural character with modern comforts. Every space has been thoughtfully updated to maximize natural light and highlight effortless flow throughout the residence. The main level showcases rich plank flooring, expansive formal living and dining spaces, and a welcoming great room anchored by a stunning Rumford fireplace. The kitchen features clean line sand timeless craftsmanship for a busy family featuring an additional dishwasher and luxurious heated floors paired with a highly functional rear galley pantry for exceptional storage. A main-floor fifth bedroom serves as an ideal guest suite or private home office. Upstairs, the expansive primary suite acts as a private sanctuary with its own Rumford fireplace, walk-in closet and private 5 piece ensuite. A second floor laundry, and three additional spacious bedrooms complete the upper level. Downstairs, the finished lower level offers versatile space perfectly suited for a media room, home gym, or play area along with ample storage. The backyard settles in with old world charm enjoying a south-facing private retreat featuring two oversized decks, one covered, designed for entertaining amidst mature, lush grounds. Complete with major mechanical updates-including a newer furnace, central A/C, and an owned hot water tank-this distinguished home offers total peace of mind. Located just steps from downtown Oakville, the lake, top-ranked schools, and scenic parks, this is a rare opportunity to own a turnkey heritage property in one of Oakville's most coveted neighborhoods.

332 PALMER Avenue, Oakville
$999,999
3 Beds ⋅ 2 Baths ⋅ W13830744 MLS
Welcome to Oakridge Heights in coveted Old Oakville, where bespoke design, elevated finishes, and effortless convenience come together in a truly refined condominium residence. Thoughtfully renovated with a discerning eye, this 2 bedroom + den, 2 bathroom suite offers a sophisticated sense of flow, with wide-plank flooring, expansive floor-to-ceiling windows, and sweeping treetop and lake views that bring a quiet elegance to every principal space. The open-concept living and dining area is warm, stylish, and inviting, featuring custom lighting, balcony access, and a seamless connection to the designer kitchen. Finished with dramatic stone countertops and backsplash, sleek flat-panel cabinetry, stainless steel appliances, built-in oven and microwave, and a waterfall-style peninsula, the kitchen makes an impressive statement. The suite also features a well-designed home office with custom built-ins, a spacious primary bedroom with panoramic views, luxurious 5 pc ensuite beautifully updated bathrooms with glass showers, designer tile, gold and black accents. A well-appointed second bedroom, stylish 3-piece bathroom, dedicated office with French door and built-in shelving/desk, plus in-suite laundry with stackable washer/dryer and laundry sink add everyday function and comfort. Residents enjoy outstanding building amenities, including an indoor pool, gym, hobby room, and party space. Ideally positioned just steps to the GO/VIA Station, Whole Foods, and Olde Oakville Market Place, and only a short stroll to downtown Oakville's boutiques, restaurants, lakefront, parks, and trails, this exceptional residence offers a polished lifestyle with easy highway access and a convenient commute to downtown Toronto. Thoughtfully finished from top to bottom, this condo blends comfort, style, storage, and incredible views in one sophisticated package.Offer Remarks

50 Old Mill Road Unit 703, Oakville
$6,975,000
3 Beds ⋅ 3 Baths ⋅ W13825508 MLS
Lakefront home, nestled on Old Oakville's Second Street, this residence offers a blend of timeless elegance, luxury, and unparalleled waterfront living. Completely reimagined top to bottom, showcasing an aesthetic designed for both family living and comfortable downsizing. Bathed in natural light, offering breathtaking lake views from nearly every room, you will find tranquility and grandeur from the moment you enter. Glowing hardwood flooring, custom millwork and paneling, recessed lighting, and designer finishes elevate every space.The kitchen, with panoramic lake views, features custom cabinetry, integrated top-of-the-line appliances, and an oversized island with seating for four. Quartz countertops and full-height quartz backsplash create a striking focal point, complemented by gold pendant lighting.The living room is designed for both comfort and style, featuring custom built-in cabinetry with illuminated shelving, gas fireplace, and expansive windows framing the sparkling waters of Lake Ontario. The main-floor primary suite, spacious and serene, featuring a walk-in closet. Spa-inspired ensuite with a freestanding soaker tub, glass walk-in shower, vanity, and gold fixtures and lighting. Two additional bedrooms on the upper level for family and guests, with private balcony overlooking the waterfront. Enjoy a beautifully appointed main-floor laundry room with custom cabinetry and stacked appliances. Enjoy riparian rights from a spectacular waterfront deck featuring glass railings and steps to the shoreline. Maximizing the panoramic water views, an unrivaled setting for entertaining, relaxing, and embracing Oakville's most prestigious waterfront lifestyle. Complete with a detached 2 car garage and ample private parking. Furniture by FOR living, Art by Harbour Gallery. Luxury Certified.

21 Second Street, Oakville
$1,767,000
4 Beds ⋅ 3 Baths ⋅ W13821004 MLS
Location! Location! Stunning Executive freehold townhome in prime downtown Oakville, fabulous low maintenance lifestyle, perfect location just steps to the charming main street with an abundance of upscale stores, fine dining, cafes, steps to theater, lake, harbour, river & fabulous Oakville Club. Built by award-winning DQI (Design Quorum Inc.) Featuring over $150,000 in modern renovations (detailed list of all upgrades 2018-2026 available upon request & attached to listing), beautiful new natural oak hardwood floors, sun filled open concept main floor great room with 10' ceilings & huge picture windows filling the home with natural light, renovated gourmet kitchen with centre island, granite counters & stainless appliances & wine fridge, 4 spacious bdrms, 2.5 renovated baths, freshly painted thruout, modern pot lights thruout, primary bdrm features 18' vaulted ceiling, spa-like ensuite & walkin closet, 4 walkouts to sundecks on main & upper levels, 4th bdrm loft features walk-in closet and walkout to private rooftop terrace, lovely views over 16 Mile Creek, handy 2nd floor laundry ideally situated close to all bdrms, professionally finished basement features spacious family room and large storage room, this beautifully appointed freehold features 2,355 sq.ft. of living space, double car garage with ability to park a 3rd car in front of garage door in lane, primary retreat features vaulted ceilings, spa-like ensuite, walk-in closet, , handy 2nd level laundry, exterior professionally painted in modern upscale colour, This home is the perfect blend of downtown convenience, modern sophistication & low maintenance offering the ultimate lifestyle 10+++

236 Randall Street, Oakville
$4,298,000
5 Beds ⋅ 5 Baths ⋅ W13819390 MLS
OUTSTANDING EXECUTIVE FAMILY OPPORTUNITY! Located in the coveted ORCHARD BEACH neighbourhood of OLD OAKVILLE, this home is just a stone's throw from the LAKE ONTARIO and a short stroll to downtown Oakville's shops and restaurants. Designed by John Willmott and enhanced with numerous features, it offers joyous familyliving. The modern, open-concept floor plan includes a vaulted, sun-lit family room adjacent to a large chef's kitchen and eat-in area. Quality garden doors open to a magnificent stone back porch, complete with a linear fireplace and views of the quality private Todd gunite pool, hot tub, and Aldershot landscaping.Ideal for entertaining, the home features a separate pantry and servery next to the dining room, which boasts stunning stained glass windows. The office is quietly tucked away with street views for natural light.The second level hosts a fabulous principal suite with built-in cabinets and shelving, a balcony with seasonal lake views, a 5-piece ensuite, and a walk-in closet. Additionally, there are three more spacious bedrooms and two further convenient bathrooms. The lower level includes an impressive projector entertainment centre with a cozy gasfireplace, a second bonus office, a large bedroom, and another bathroom. The stone walkways and patios outside are exceptional, welcoming you into this warm and inviting family home. Situated on a quiet, tree-lined street, this special home is serenaded by the sounds of the waves rolling in. You will be enchanted.

29 Howard Avenue, Oakville
$589,900
1 Beds ⋅ 2 Baths ⋅ W13812960 MLS
Welcome to suite living at 221 Robinson Street. Spanning 750 square feet, this meticulously maintained one-bedroom, one-and-a-half-bathroom residence offers a seamless blend of comfort, style, and boutique low-rise charm. Generous open-concept living and dining area featuring clean lines, bright windows, and an effortless flow designed for both daily living and entertaining. Move-in ready condition with modern flooring, pristine finishes, and a conveniently located partial bath (powder room) for guests in addition to the primary ensuite. Comes complete with 1 owned underground parking space and 1 storage locker. Unbeatably situated in vibrant Downtown Oakville, step outside your door to premier dining, boutique shopping, scenic lakeside parks, and the waterfront trail. Commuters will love the quick access to the Oakville GO Station, QEW, and 403.

221 Robinson Street E Unit 204, Oakville
$3,425,000
3 Beds ⋅ 4 Baths ⋅ W13812244 MLS
Poised within Fernbrook's newest Old Oakville community, 335 Helen Lawson Lane presents a rare fusion of architectural refinement, modern convenience, and effortless ownership. Brand-new and never occupied, this luminous end-unit townhome offers three bedrooms, three bathrooms, an attached garage, and more than $300,000 in thoughtfully curated upgrades. Natural light animates every level, while a private elevator connects the residence with exceptional ease. The ground-floor family room extends to a secluded backyard and includes generous storage, appliance rough-ins, and provisions for a future bar-an elegant foundation for entertaining or offering guest accommodations with the 3 pc bath.. Above, the principal living level is composed for gracious gatherings. The Downsview kitchen is appointed with Wolf, Sub-Zero, and Cove appliances, a beverage refrigerator, and a walk-in pantry and large upgraded centre island. The open concept living room offers a walk out to deck and a gas fireplace creates a sophisticated focal point. The separate dining area gives the perfect space for entertaining family and friends. A powder room completes the floor. The bedroom level reveals a tranquil primary retreat with walk out to deck and a rough-in for an additional gas fireplace. Two spacious walk in closets and a spa-inspired four-piece ensuite complete this special space. Two further bedrooms share a beautifully appointed four-piece bath, while the laundry room provides a sink and practical storage. The unfinished basement adds valuable flexibility for storage or future customization. Moments from Whole Foods Market, Oakville GO Station, downtown boutiques, acclaimed dining, and Lake Ontario. This distinguished residence offers turnkey luxury in one of Oakville's most connected settings. Need some designer ideas to complete your new home look? The Seller will offer 10 hours of designer time with Khachi Design. Luxury Certified

335 Helen Lawson Lane, Oakville
$2,899,000
4 Beds ⋅ 3 Baths ⋅ W13798472 MLS
A rare combination of character, space and exceptional walkability in the heart of Downtown Oakville. Set on an impressive 70-foot-wide property, this beautifully renovated four-bedroom home blends the charm of an established residence with the quality and functionality of a thoughtful, high-end renovation. Extensively updated by Stonewood Homes, the interior features wide-plank white oak flooring, exposed wood beams, natural stone fireplaces and custom millwork throughout. The main level offers an impressive collection of living spaces, beginning with a bright enclosed sunroom and flowing through separate living and dining rooms to the open-concept kitchen and family room at the rear of the home. The kitchen is beautifully appointed with custom Chervin cabinetry, high-end appliances and a large centre island with seating. A substantial walk-through servery provides exceptional storage complete with additional cabinetry, sink, beverage refrigeration and wine storage. Upstairs, four bedrooms include a spacious primary suite with a walk-in closet and a beautifully finished ensuite featuring a freestanding tub. Three additional bedrooms and a second full bathroom provide an ideal layout for family living. The finished lower level adds valuable living space with a large recreation room, laundry room, workshop and extensive storage. Outside, the unusually wide lot allows for multiple outdoor living spaces surrounded by mature trees that create a wonderful sense of privacy. A large rear deck extends the main living area outdoors, while the landscaped backyard leads to a separate covered pavilion. Adding to the property's appeal is a detached two-car garage and two separate driveways, a rare offering this close to Downtown Oakville. Located just steps from the restaurants of downtown, and within easy reach of the lakefront, harbour, parks and schools, this is a unique opportunity to enjoy one of Oakville's most desirable and walkable neighbourhoods.

139 Allan Street, Oakville
$7,000,000
W13793920 MLS
An exceptional opportunity to own a substantial 11,000 sq. ft. four-storey office building in the heart of downtown Oakville. Ideally located within walking distance of Oakville's vibrant downtown, restaurants, cafés, shops and amenities. Featuring high-end executive finishes, the property currently serves as the headquarters of a prestigious financial wealth management firm catering to high-net-worth clients. The sophisticated layout includes multiple private offices, boardrooms, four kitchens, two fireplaces and an outdoor patio. The flexible configuration provides an excellent opportunity for an owner-user, corporate headquarters or multi-tenant investment strategy. A rare downtown Oakville offering combining scale, quality, location and flexibility-ideal for investors or professional users seeking a distinctive commercial property in one of Oakville's most desirable business locations.

305 Church Street, Oakville
$1,159,000
6 Beds ⋅ 2 Baths ⋅ W13788524 MLS
3+3 bedrooms Bungalow with separate entrance in College Park area. Renovated throughout with an eat-in kitchen, open-concept living/dining, spacious 3 bedrooms, a granite 4-pc bath, and laundry on the main level. Professionally finished lower level offers 3 bedrooms, Eat in kitchen, living room, 3 pc bath and laundry. Walking distance to Sheridan College, French Immersion Public & Catholic Elementary and High Schools, Oakville Place, Library & Parks. Just minutes to QEW, 403, 407 & Go Transit access.

35 Culham Street, Oakville
$6,575,000
5 Beds ⋅ 5 Baths ⋅ W13779262 MLS
153 Balsam Drive is a sophisticated 4,337 sqft custom residence set on a 50' x 304' park-like lot in one of Oakville's most sought-after settings. Close to Downtown Oakville, top-rated schools, the home pairs craftsmanship with thoughtful functionality. A dramatic double-volume marble foyer with heated flooring and architectural staircase creates an elegant arrival, while custom millwork, designer lighting, oversized windows and premium white oak flooring establish a refined aesthetic throughout. The main level is designed for family living and entertaining, with gracious living and dining spaces flowing into a warm family room with a wood-burning fireplace. A dedicated office overlooks mature greenery. At the heart of the home, the kitchen features a 10' x 4' marble island, face-frame cabinetry, marble surfaces, bespoke lighting and a 60" Lacanche range with a custom plaster hood. A marble-finished pantry and heated natural-stone mudroom add function and elegance. Upstairs, four bedrooms each feature a walk-in closet. The primary suite offers a vaulted ceiling, double skylights with remote blinds, a lounge area and an oversized walk-in closet. The spa-inspired ensuite features heated marble floors, a steam shower with double heated marble seating, custom wainscoting, detailed marble trim and an imported Water Monopoly bathtub. The lower level extends the home's living and entertaining spaces with 10' ceilings and zoned underfloor heating. A fifth bedroom, recreation and games rooms, gym, wine cellar and theatre/flex space offer exceptional versatility for family living and entertaining. A heated three-car garage with car-lift capacity for two additional vehicles, plus exterior snow-melt infrastructure, adds year-round convenience. 153 Balsam Drive is a rare combination of timeless architecture, refined materials, modern functionality and exceptional attention to detail, thoughtfully brought together on one of Oakville's most coveted streets.

153 Balsam Drive, Oakville
$2,398,900
3 Beds ⋅ 4 Baths ⋅ W13767320 MLS
Welcome to 433 Allan Street, a distinctive residence designed for effortless living offering a perfect blend of timeless sophistication and low maintenance convenience set privately behind gates on a professionally landscaped tree lined lot. Newly renovated, spacious 9ft ceilings throughout and skylights create a bright inviting atmosphere including rich hardwood floors, custom millwork and built in cabinetry. The chef inspired kitchen features premium Bosch appliances, generous island and an inviting living room anchored by a striking fireplace. Wake up to the morning sunrise as the primary suite is a tranquil retreat with high ceilings, skylights, a spa-inspired ensuite including make up vanity, heated floors and a private outdoor living space overlooking the private grounds. A second bedroom, additional bathroom with heated floors and discreet stacked laundry alcove complete the main level with exceptional convenience. Entertain in style with a premium outdoor kitchen in a stunning alfresco setting with your own pizza oven and fire bowl. A finished lower level, featuring a third bedroom, full bathroom, kitchenette, laundry room, private courtyard and a separate walk up entrance offers flexibility for family and guests. Just steps outside, a detached garden suite with garage complete with bedroom, bathroom, kitchenette and private courtyard adds rare versatility for guests, extended family, a studio, home office, nanny suite or gym. A carport and ample parking for 10+ vehicles further enhance the property. Additional features include new windows 2023, hot tub and artificial turf. Offering just over 1423 square feet of living space with an additional 422 square feet in the garden suite. The best of downtown Oakville's lifestyle living is just steps away from waterfront, marina, parks, boutiques,restaurants,GO Station,Whole Foods,major highways and sought after schools. A rare opportunity to own a turn key property offering privacy and character in SE Oakville.

433 Allan Street, Oakville
$2,300,000
4 Beds ⋅ 3 Baths ⋅ W13765540 MLS
This rare find in the heart of Old Oakville is a bungalow duplex backing onto scenic 16 Mile Creek, beautifully renovated in 2021 and designed by Kate Zeidler (KZID). Steps from Downtown Oakville, Lake Ontario and the Oakville GO Station, this unique property offers 2 distinct 2-bedroom units - each featuring a separate garage, driveway, private decks with glass railings and breathtaking views. Unit 1 highlights hardwood floors, a gas fireplace in the family room, open-concept living and dining room, kitchen with heated floor, quartz counters & stainless steel appliances, heated floors in the 4pc bath, sunroom and private stairs leading down to the creek dock. Unit 2 offers an open-concept living area with gas fireplace, modern kitchen with breakfast bar, a primary suite with walk-in closet/office space, a 4pc bath with heated floors and ensuite laundry. Both units have independent furnace, A/C and utilities. This legal non-conforming duplex offers strong income potential for dual rental income (currently renting Unit 2 @ $4000/month), multi-generational families or live in one unit while leasing the other. Turnkey waterfront property in a premium location!

372 Trafalgar Road, Oakville
$9,180,000
6 Beds ⋅ 5 Baths ⋅ W13765232 MLS
Gracefully located at the foot of Trafalgar Road in the heart of prestigious Old Oakville, this extraordinary lake view estate presents a rare opportunity to own one of the area's most distinguished residences. Set on an expansive 155' x 104' property, the home enjoys breath taking views of Lake Ontario, offering ever-changing waterfront vistas, spectacular sunrises, and an unparalleled lifestyle just steps from the town's vibrant downtown core. Steeped in history and meticulously transformed into a magnificent custom residence, this approximately 10,000 sq. ft. home spans three levels of refined living space. Featuring six spacious bedrooms and nine luxurious bathrooms, every detail has been thoughtfully designed to blend timeless elegance with modern comfort. The grand interior showcases soaring ceilings, a custom chef's kitchen, sophisticated entertaining spaces, and designer finishes throughout. Exceptional amenities include a private elevator, walk-in wine cellar, fully equipped fitness area, loft space, and a walk-out lower level ideal for extended family, guests, or a nanny suite. The home's striking exterior seamlessly blends timeless architectural character with refined modern updates. Natural stone and wood exterior finishes create an elegant façade that complements its coveted waterfront setting. The expansive, maturely landscaped grounds provide exceptional privacy while maximizing lake views from multiple outdoor vantage points. It boasts your own private putting green, a fire pit area, expansive deck/entertaining area including a pizza oven and gorgeous salt water pool with a captivating water fall. Beyond the home, residents enjoy an enviable walkable lifestyle with immediate access to the lakefront, marina, scenic trails, parks, boutique shopping, cafés, and fine dining. Combining historic character, exceptional craftsmanship, and a premier waterfront-adjacent location, 26Trafalgar Road represents luxury Oakville living at its finest.

26 Trafalgar Road, Oakville
$3,795,000
4 Beds ⋅ 4 Baths ⋅ W13763614 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
$1,379,000
3 Beds ⋅ 3 Baths ⋅ W13754726 MLS
Penthouse perfection with breathtaking views of Lake Ontario and the Toronto skyline. Welcome to Oakridge Heights, one of Oakville's most prestigious addresses. This beautifully renovated 1,984 sq. ft. penthouse offers three bedrooms, 2.5 bathrooms and an additional 486 sq. ft. of outdoor living space on a private wraparound balcony. Natural light fills the open concept layout, with South facing views over Sixteen Mile Creek toward Lake Ontario and east facing views of the Toronto skyline. Purchased in 2019, the suite was extensively renovated in 2020, with more than $372,000 invested in thoughtful upgrades and improvements. The kitchen and all three bathrooms were completely remodeled by Oakville Kitchen and Bath. Additional upgrades include new flooring, designer lighting, a custom entertainment centre, California Closets throughout, and automated blinds and curtains by Shades of Home. The primary bedroom features new carpeting, two walk-in closets, a built-in safe and a lockable jewelry drawer. The den's custom entertainment centre includes a 65-inch Sony television and Bose sound system, which will remain with the suite. Further improvements include new heat pumps in the den and living room and a new Samsung washing machine. Enjoy two side-by-side parking spaces conveniently located near the elevator, two storage lockers and easy access to the Oakville GO station and highways. Downtown Oakville is approximately a 15-minute walk away, with Whole Foods and other gourmet shopping just minutes from your door. Beautifully finished, exceptionally spacious and completely turnkey this is penthouse living at its finest.

60 Old Mill Road Unit PH1, Oakville
$989,000
3 Beds ⋅ 2 Baths ⋅ W13752256 MLS
Welcome to this sophisticated 2 bed plus den condo, ideally situated in the heart of Oakville. Short walk from historic Downtown Oakville, this beautifully renovated suite offers 1425 sqft. On the ground floor, it provides easy access for family and friends - no elevator! - convenient every day! The open-concept kitchen features a large island with built-in wine rack, sleek quartz countertops, and custom cabinetry with additional built-ins in the dining area. High-end appliances, including a convection microwave, induction cooktop, and built-in wall oven with a warming drawer, add to the kitchen's appeal. New hardwood flooring throughout adds style and comfort. Designed for everyday and for entertaining, the bright and airy living area is filled with natural light from large windows and anchored by an inviting electric fireplace. The den opens onto a balcony that overlooks the property's lush gardens and mature trees, creating a peaceful workspace. The primary bedroom boasts a private terrace, a spacious walk-in closet, and luxurious ensuite with glass walk-in shower, deep soaker tub, and heated towel rack. Both bathrooms have been thoughtfully renovated with striking tile work, including stylish black accents. A separate walk-in pantry and in suite laundry provide additional convenience. For commuters, the location is ideal, easy access to major highways and the GO Train station just steps away. A truly walkable lifestyle awaits, Whole Foods, Starbucks, LCBO, Shoppers, and more just a block away, while the nearby community centre is a 15-min walk. The well-managed building is home to a welcoming mix of residents, and reasonable condo fees. Amenities include party room with billiards and kitchenette, indoor pool, sauna, gym and EV chargers. The unit comes with one parking and one locker. Completely move-in ready! Don't miss this exceptional opportunity to live in a sought-after location.

50 Old Mill Road Unit 105, Oakville
$999,000
2 Beds ⋅ 2 Baths ⋅ W13747184 MLS
Experience timeless elegance in this rare, executive corner unit condo located in Oakville's prestigious Old Mill Community. Thisexpansive 1436 sqft residence offers a perfect blend of sophisticated design and natural beauty, featuring panoramic picturewindows that capture breathtaking unobstructed views of 16 mile creek, offering complete privacy and tranquility. Thesun-drenched living space boasts exquisite finishes, 9' ceilings, hardwood floors throughout, a chef-inspired kitchen with warmwood cabinetry, quartz counters, 4 new high end appliances (2026), a pantry closet, and a reading nook or dining area withwalk-out to a private balcony for watching the seasons change over the water. Other features include 2 spacious bedrooms withoversized closets with custom built-ins, 2 luxurious bathrooms, a Paris inspired laundry room, loads of storage space, andtandem two car parking directly beside the building entrance. Building amenities include a freshly renovated lobby, outdoorpergola and seating, pool, gym and sauna. Situated just steps from Whole Foods, historic Downtown Oakville, fine dining,boutique shopping, and the Go Station, this property offers an unparalleled lifestyle of convenience and luxury.

60 OLD MILL Road Unit 702, Oakville
$2,950,000
5 Beds ⋅ 2 Baths ⋅ W13745990 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
$1,849,000
3 Beds ⋅ 2 Baths ⋅ W13740174 MLS
Welcome to 344 Maple Avenue, an excellent example of mid-20th Century architecture, unique to Old Oakville, in a beautiful Craftsman-style bungalow. From the moment you arrive, you'll know you've found something special - starting with the welcoming front porch, the perfect spot to enjoy your morning coffee. This deceptively spacious 3-bedroom home features impressively large living and dining spaces, great for entertaining family and friends. It is flooded with natural light from its multiple large windows and glazed doors, yet it maintains a cozy ambiance with its wood-burning fireplace, hardwood floors throughout, and custom built-in cabinetry. The character-filled kitchen offers a highly functional layout and the bright breakfast nook enjoys views of the spectacular yard. The home is situated on an expansive 178 x 57 ft lot featuring beautifully landscaped grounds with mature trees and shrubs, perennial gardens, manicured lawns (with full sprinkler system), and multiple garden rooms, including a secluded courtyard for afternoon tea, and a private patio for evening cocktails. The oversized double-car garage is a huge bonus and a rare find in this area. This highly desirable enclave of quiet, tree-lined streets is just a short stroll from the shops of Olde Oakville Plaza, the Oakville Trafalgar Recreation Centre, Oakville GO, and everything downtown Oakville has to offer - including the harbour, lakeside parks and trails, casual and fine dining, shopping, the library, and the arts centre. The property also offers easy highway access and is within walking distance of top-tier public and private schools. This is a great opportunity to get into Old Oakville and it offers lots of options - move in and enjoy, add on and renovate to your taste, or build a new dream home on one of the largest lots in the neighbourhood. The pictures and floor plans alone don't do this unique property justice. Book your visit to see it in person today!

344 Maple Avenue, Oakville
$2,599,000
4 Beds ⋅ 3 Baths ⋅ W13724754 MLS
Welcome to this exceptional two-storey family residence nestled on one of South East Oakville's most desirable, tree-lined streets. Combining traditional charm with an ideal functional layout. There are generous spaces for entertaining and everyday family life. Step into the inviting living room, featuring a cozy fireplace and elegant California shutters that fill the space with warm, natural light. The updated eat-in kitchen serves as the heart of the home, complete with built-in appliances, ample cabinetry, and a spacious eat in area. For formal gatherings, the spacious dedicated dining room easily accommodates large family dinners and holiday celebrations. The dramatic main-floor family room steals the show with its soaring vaulted ceilings, second fireplace, and expansive windows. Slide open the doors to step directly onto the private back deck, overlooking a beautifully landscaped, west-facing rear garden-the ultimate setting for enjoying golden-hour sunsets, outdoor dining, and summer entertaining. Conveniently located on the main level, the spacious primary bedroom serves as a peaceful retreat, complete with a private 4-piece ensuite bath. Upstairs, you will find two additional bright bedrooms, fantastic storage solutions, and a second full 4-piece bathroom, making it ideal for kids, guests, or a dedicated home office. The fully finished basement significantly extends your living space, offering endless possibilities for a media room, play area, or home gym, along with a third 4-piece bathroom for added convenience.Located in a premier school district close to top-rated public and private schools, downtown Oakville's boutique shopping and dining, parks, and the lakefront, this South East Oakville gem perfectly blends main-floor comfort with long-term versatility. A rare opportunity on a prime street!

380 Watson Avenue, Oakville
$6,250,000
6 Beds ⋅ 7 Baths ⋅ W13724050 MLS
This magnificent custom residence is nestled in one of Oakville's most prestigious neighbourhoods, just a short stroll from the lake and downtown Oakville. Offering over 6,500 sq. ft. of exquisitely designed living space, this exceptional home seamlessly blends contemporary sophistication with exceptional luxury. Every detail has been meticulously considered, from heated floors on the main and lower levels to a private elevator serving all three floors. A sunlit two-storey foyer introduces an elegant interior defined by refined finishes and thoughtful design. The expansive Great Room features soaring 20-foot ceilings and a dramatic wall of windows overlooking the professionally landscaped grounds. Walk out to an elegant patio with gas BBQ hookup, ideal for summer entertaining and alfresco dining. The gourmet kitchen is a true showpiece, featuring sophisticated two-tone cabinetry, an expansive centre island and state-of-the-art appliances. The adjoining butler's pantry provides additional prep space and connects seamlessly to the elegant Dining Room, where built-in speakers and views of the front gardens create an exceptional setting for entertaining.A serene formal Living Room offers a refined retreat, while the main-floor bedroom, easily converted to an office, features a private ensuite and direct patio access. A sculptural floating staircase leads to the skylit second level, where the luxurious primary suite offers two walk-in closets and a spa-inspired ensuite. Three additional bedrooms, each with secure closets and heated ensuites, provide comfort and privacy. The lower level is an entertainer's dream, featuring a heated underground garage with vehicle turntable, stylish recreation room with walk-up to the backyard, and space for a state-of-the-art theatre or gym.An extraordinary residence offering sophisticated design, exceptional amenities and an unparalleled Oakville lifestyle.

533 Carson Lane, Oakville
$439,000
W13723722 MLS
Exceptional opportunity to own an established The WORKS Craft Burgers & Beer franchise in the heart of Downtown Oakville, this prime location is surrounded by popular restaurants, boutique shops, professional businesses and strong pedestrian activity. Just steps from Oakville's picturesque waterfront, harbour and Lake Ontario, the restaurant benefits from an excellent downtown location that attracts local residents, professionals and visitors throughout the year. This established restaurant features a welcoming dine-in area plus a desirable outdoor patio, providing additional seating and excellent seasonal appeal during the warmer months. The business operates under the well-known Canadian The WORKS Craft Burgers & Beer brand and offers dine-in, takeout and delivery options. Excellent visibility along Lakeshore Rd E with convenient access to the surrounding Downtown Oakville amenities. A great opportunity for an owner-operator, experienced restaurateur or investor looking to acquire an established franchise restaurant in one of Oakville's most desirable and vibrant commercial districts. Take advantage of the existing setup, recognized brand and outstanding location while exploring further opportunities to grow the business.

149 Lakeshore Road E, Oakville
$1,089,000
3 Beds ⋅ 2 Baths ⋅ W13723128 MLS ⋅ Oakridge Heights BLDG.
Luxurious updates, amazing location and breathtaking views of 16 Mile Creek, it will be tough to find a more perfect home in the sky. With 2 Beds and a den, 9' ceilings and over 1300sqft of living space, this beautifully renovated unit is complemented by almost 400sqft of private wraparound terrace. Offering an extraordinary expansion of the total living space, the terrace is an exceptional setting for morning coffee, evening entertaining or simply enjoying the changing seasons. Custom designed gas fireplace with distinctive surround/mantle anchors the living & dining space providing a sophisticated focal point. An important distinguishing feature - the gas fireplace - is unique to the Penthouse units! The open-concept kitchen features custom cabinetry, quartz counters, & top-tier appliances. The adjacent den is perfect for an office. The primary suite is the 'cherry on top' with walk-in closet customized with drawers and shoe cabinet, and the 4-piece ensuite Bath that has been tastefully updated. Overlooking the terrace, there is also a separate balcony unique to this bedroom suite. The 2nd Bed serves as a den & is a perfect guest room. The second Bath has also been updated. Rounding out the suite - a laundry room with plenty of storage space. Every detail has been carefully considered. Hardwood flooring was replaced, custom finishing details added, including solid wood doors, beautiful trim & upgraded Emtek hardware. New blinds, most of which automated, were added for comfort and privacy. Freshly painted interiors create a crisp, polished backdrop. This suite offers 2 parking spaces AND 3 storage lockers. The well managed building offers a common BBQ area, lots of visitor parking, gym, gated entry, electric vehicle charging stations, & common rooms that can handle a crowd. But above all else, the building is ideally located in the heart of Oakville close to scenic walking trails, downtown Oakville, Kerr Village, shopping, dining & steps to the Oakville GO Station.

50 Old Mill Road Unit 901, Oakville
$2,999,000
5 Beds ⋅ 3 Baths ⋅ W13722374 MLS
Well positioned property in historic Old Oakville, south of Lakeshore, just steps to the beach, Oakville harbour and Town Square. Sitting proudly up on a rise, this 2 1/2 storey home features wonderful views, light and plenty of space to create your dream home. With lot dimensions of 105' x 105' this full-sized 11,044 SF lot is exactly twice the size of adjacent properties. Savvy buyers may investigate opportunities to sever the lot or explore the creation of an accessory dwelling unit on the property. Zoning RL3, Special Provision 11. The existing home sits entirely on one half of the property in the northeast corner leaving the south and the west portions of the lot open to potential. The existing residence features high ceilings, a grand staircase, formal living room with wood burning fireplace and adjacent sunroom. Lovely southeast dining room takes in all the sunlight. The kitchen and back entrance are in the southwest corner of the main floor. The second floor features 4 bedrooms and one main bathroom. The third floor with two large rooms used as the Primary suite features wonderful views over the garden, the lake, church tower and the beautiful trees of Old Oakville.

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

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

46 Second Street, Oakville
$110,000
W13672076 MLS
Located on the vibrant, highly sought-after Kerr Street in the heart of Oakville, this well-established bakery offers a rare opportunity to own a beloved local business with over 30 years of community history. Known by loyal customers for decades, the bakery enjoys excellent visibility and steady foot traffic along one of Oakville's most popular commercial corridors. The inviting space features a charming patio, perfect for outdoor seating and seasonal gatherings. It includes a valuable liquor license that opens the door to expanded menu and evening service opportunities. With its long-standing reputation, prime location, and unique amenities, this turnkey bakery is ideally positioned for a new owner to build on its legacy and continue thriving in the lovely Oakville area.

314 Kerr Street, Oakville
$289,000
W13667878 MLS
Excellent opportunity to own and operate an established Aroma Espresso Bar in the heart of Downtown Oakville! Located on highly desirable Lakeshore Road East, this well-positioned café benefits from strong pedestrian traffic, surrounding residential and commercial activity, and excellent street exposure.The premises offer approximately 2,211 sq. ft. across the main and second floors, plus approximately 766 sq. ft. of basement space and an outdoor seating area. Fully equipped for café and restaurant operations, offering coffee, specialty beverages, breakfast, lunch, dinner and baked goods.Current base rent is approximately $9,212.50/month plus HST, additional rent, utilities and other occupancy costs. Potential franchisor-required renovations/upgrades may apply within the next 6-12 months. Buyer to verify requirements, timing and costs directly with Aroma Espresso Bar.Sale subject to landlord approval, lease assignment and franchisor approval. Do not go direct or speak with employees. All appointments through the Listing Brokerage.

321 Lakeshore Road E, Oakville
$2,999,900
2 Beds ⋅ 3 Baths ⋅ W13658162 MLS ⋅ The Randall BLDG.
Experience an exceptional standard of luxury in this rare penthouse at The Randall Residences, Oakville's most prestigious boutique condominium. Reserved exclusively for the penthouse level, soaring 12-foot ceilings, exquisite custom millwork, and refined finishes create an atmosphere of timeless elegance. A grand circular stone floor foyer welcomes you into this beautifully designed residence, complete with a spacious front hall closet, powder room, and an generous walk-in laundry room with laundry sink. The spectacular open-concept kitchen is the heart of the home, featuring a generous centre island, marble countertops, premium appliances, and seamless flow into the dining area with custom built-in pantry cabinetry. The living room is framed by floor-to-ceiling wraparound windows that flood the space with natural light, while custom built-ins and a striking fireplace provide warmth and sophistication. Step onto the private south-facing balcony to enjoy sunny views and effortless indoor-outdoor living. The luxurious primary retreat offers a beautifully appointed dressing room and a spa-inspired five-piece marble ensuite. The second bedroom is equally impressive with floor-to-ceiling south-facing windows, a generous closet, and its own private three-piece ensuite. With only 32 exclusive residences, The Randall offers unparalleled privacy and service, including 24-hour concierge, three elevator banks, impeccably maintained underground parking with soaring ceilings, two premium parking spaces, and a private locker. Perfectly situated in the heart of downtown Oakville, you're just steps from the lake, boutique shopping, cafés, fine dining, and the renowned Sotto Sotto restaurant located on the main floor. A truly exceptional opportunity to own one of downtown Oakville's most distinguished penthouse residences.

300 Randall Road Unit PH5, Oakville