1013 - OO Old Oakville Real Estate

1013 - OO Old Oakville Real Estate

Welcome to 1013 - OO Old Oakville, a charming neighborhood that beautifully blends historical elegance with modern convenience. Nestled in the heart of Oakville, Ontario, this area is renowned for its picturesque streets, tree-lined avenues, and a vibrant community spirit that makes it one of the most desirable places to live in the Greater Toronto Area.

Old Oakville is steeped in rich history, with many heritage homes dating back to the 19th century, showcasing stunning architectural designs that reflect the area’s storied past. As you stroll through the neighborhood, you'll be captivated by the quaint boutiques, artisanal cafes, and gourmet restaurants that line the streets, offering a delightful mix of shopping and dining experiences right at your doorstep.

Families will appreciate the top-rated schools and proximity to numerous parks and recreational facilities, providing ample opportunities for outdoor activities. The serene waterfront along Lake Ontario is just a stone's throw away, inviting residents to enjoy scenic walks, picnics, and breathtaking sunsets.

Old Oakville is also well-connected to major highways and public transit, making commuting to Toronto and surrounding areas a breeze. With a strong sense of community and a calendar full of local events, including farmers' markets and seasonal festivals, there’s always something happening that brings neighbors together.

In 1013 - OO Old Oakville, you’ll find not just a home, but a lifestyle that embraces both tranquility and vibrancy. Discover the charm of this remarkable neighborhood and make it your own—where every day feels like a retreat in the heart of Oakville!

Newest Listings in 1013 - OO Old 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 1375 square feet of living space with an additional 374 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
$3,850,000
4 Beds ⋅ 4 Baths ⋅ W13761476 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
$2,999,000
2 Beds ⋅ 5 Baths ⋅ W13755706 MLS
Luxury, 2 bedroom, 5 bathroom EXECUTIVE FREEHOLD townhome in DOWNTOWN OAKVILLE! Location. Location. Location. Elegant, upscale & timeless, completely redesigned by Rockcliffe Homes, no detail overlooked, this architectural show stopper has a traditional-meets-contemporary exterior that fits beautifully into the established Oakville streetscape, framed at front by a black wrought-iron fenced courtyard with brick-and-stone pillars. The interior features 10' ceilings, walls of windows, custom built-ins, & heated bathroom floors. Entry level offers versatile, sophisticated flex space, formal enough for entertaining but could function beautifully as either a home office, family room or sitting room, 2 piece powder room, double closet, interior garage entry, & 3 level barrier-free access with ELEVATOR. Open riser staircases with illuminated floating wood treads create a dramatic architectural focal point throughout. The second floor is long, open & is generously proportioned, oak floors, large windows wrap around entire living area & flood the space with natural light. Open concept kitchen & dining area with sleek full-height cabinetry & 10 integrated Miele appliances. Striking oversized ceasarstone centre island with gas cooktop provides an extensive preparation & entertaining space. Private deck for enjoying morning coffee or evening cocktails. Emphasizing the home's spacious connected layout , the living room with linear fireplace & striking coffered ceiling with recessed lighting & illuminated panels contribute to the architectural & upscale character of this home. Rise to the King-Sized Primary Retreat with gas fireplace, spa-like ensuite, w/i closet, floor to ceiling windows, stunning views. The second bedroom has a beautiful 3 pce ensuite. A bright spacious laundry room completes this level with access to the 40' x 17' roof deck constructed of IPE wood. Finished lower level with built ins, 2 pce powder, & abundance of storage. Garage (1) & Covered Carport (2)

125 George Street, 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
$499,999
2 Beds ⋅ 1 Baths ⋅ W13754342 MLS
Welcome to Oakridge Heights, where comfort, convenience, and lifestyle come together in the heart of Old Oakville. This bright and beautifully maintained 1+1 bedroom condo offers an ideal layout for young professionals, couples, downsizers, or anyone seeking flexible living space. The spacious primary bedroom features hardwood flooring, double closets, and semi-ensuite access to a 4-piece bath complete with a relaxing whirlpool tub. Soaring 9-foot ceilings and an open-concept living/dining create an airy, inviting atmosphere throughout. The versatile den is perfect as a home office, guest room, nursery, or creative studio-adapting effortlessly to your lifestyle. Complete with 1 parking space and 1 locker, this home offers both convenience and functionality. Commuters will love the easy access to the GO Station, QEW, and Highway 403, while weekends can be spent exploring Downtown Oakville's vibrant shops, cafés, and restaurants. Enjoy nearby trails along 16 Mile Creek and the shores of Lake Ontario, offering the perfect balance of urban convenience and outdoor living. Whether you're starting your next chapter together or looking for a stylish space to call your own, this Oakville gem is ready to welcome you home.

50 Old Mill Road Unit 706, 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
$1,949,000
4 Beds ⋅ 4 Baths ⋅ W13741076 MLS
ATTENTION BUILDERS, RENOVATORS & INVESTORS! Rare opportunity in the heart of prestigious Old Oakville. Located on one of the neighbourhood's most coveted streets, 374 Spruce Street sits on an impressive 60 x 142 ft south-facing lot surrounded by mature trees and multi-million-dollar custom homes. An exceptional opportunity to build your dream home, undertake a renovation, or secure a premium property for future investment. The existing bright and spacious 3+1 bedroom, 3-bathroom bungalow offers approximately 1,850 sq ft above grade plus a finished lower level and is vacant for immediate possession. Zoned RL3-0. Enjoy an outstanding Old Oakville lifestyle within walking distance to downtown Oakville, the lake, parks, shops, restaurants and highly regarded schools including OTHS, St. Mildred's and Linbrook. Build new, renovate or invest in one of Oakville's most established and desirable neighbourhoods. Buyer to complete their own due diligence regarding zoning and future building potential.

374 Spruce Street, Oakville
Start Your Search