1013 - OO Old Oakville Homes for Sale

1013 - OO Old Oakville Homes for Sale

Welcome to 1013 - OO Old Oakville, a charming neighborhood that perfectly blends historic charm with modern conveniences. Nestled in the heart of Oakville, Ontario, this picturesque area is renowned for its stunning tree-lined streets, beautifully maintained parks, and a vibrant community atmosphere. With its close proximity to Lake Ontario, residents can enjoy scenic waterfront views, leisurely strolls along the shoreline, and a variety of outdoor recreational activities.

Old Oakville is characterized by its diverse architectural styles, ranging from classic Victorian homes to contemporary builds, providing a unique character that appeals to a wide range of buyers. Whether you’re searching for a cozy bungalow or a spacious family home, you’ll find a variety of homes for sale that cater to different tastes and budgets. This neighborhood is perfect for families, professionals, and retirees alike, offering a tranquil lifestyle while being just a stone's throw away from the bustling downtown area.

In addition to its beautiful homes, 1013 - OO Old Oakville boasts a wealth of amenities. Residents can enjoy an array of boutique shops, gourmet restaurants, and local cafes, all within walking distance. The area is also home to highly regarded schools and community centers, making it an ideal place for families to settle down.

With its rich history, vibrant community, and a selection of homes for sale, 1013 - OO Old Oakville is not just a place to live; it’s a lifestyle choice. Discover the charm of this neighborhood today and envision your future in one of Oakville's most sought-after locations!

Newest 1013 - OO Old Oakville Homes for Sale

$3,198,000
4 Beds ⋅ 3 Baths ⋅ W13599614 MLS
Set on a high sought-after, tree-lined street in the heart of Old Oakville, this beautifully renovated residence offers refined, move-in ready living in one of the town's most coveted neighbourhoods. Bright, sophisticated interiors are defined by wide-plank white oak floors, clean architectural lines and an effortless connection to the outdoors.At the heart of the home, the custom kitchen features sleek cabinetry, quartz countertops, premium appliances and a beverage fridge, flowing seamlessly into the breakfast area and inviting great room. A striking three-sided gas fireplace creates a natural focal point, while expansive four-panel Kolbe sliding doors open to a private backyard designed for everyday enjoyment and exceptional entertaining.The professionally landscaped gardens offer a true outdoor retreat, complete with a spacious lounge centred, dining terrace, built-in outdoor kitchen with gas barbecue and beverage fridge, mature privacy plantings and a generous lawn.The upper floor offers three well-proportioned bedrooms, including a tranquil primary suite overlooking the gardens with a walk-in closet and beautifully appointed five-piece ensuite featuring double vanities, a soaker tub and glass shower. Two additional bedrooms and a family bathroom complete this level.The finished lower level, with its side entrance, adds exceptional flexibility with a fourth bedroom, recreation room and versatile space ideally suited for a home office, gym or guest accommodation.Perfectly positioned just moments from the lake, downtown Oakville, the New Central Public School, Oakville Trafalgar High School, Whole Foods, the GO Station, and exception recreation facilities and parks. This is a rare opportunity to enjoy an outstanding home in one of Oakville's most established and sought-after neighbourhoods.

303 Watson Avenue, Oakville
$6,975,000
3 Beds ⋅ 3 Baths ⋅ W13594134 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
$2,349,000
5 Beds ⋅ 3 Baths ⋅ W13536632 MLS
Nestled Just Moments From The Shores Of Lake Ontario In One Of Oakville's Most Coveted Neighbourhoods, 298 Douglas Avenue Offers The Perfect Blend Of Lakeside Living And Refined Family Comfort. This Beautifully Renovated 4+1 Bedroom, 3 Bathroom Residence Has Been Thoughtfully Redesigned From Top To Bottom, Combining Timeless Character With Elevated Modern Finishes. The Main Floor Features Rich Hardwood Flooring, Elegant Mouldings, Pot Lights, And Expansive Windows That Fill The Home With Natural Light. The Custom Chef's Kitchen Is A True Showpiece With Quartz Countertops, Stainless Steel Appliances, Designer Lighting, A Large Centre Island With Seating, And Seamless Access To The Backyard, Ideal For Entertaining. The Inviting Living Spaces Provide Warmth And Sophistication, Including A Cozy Fireplace And Effortless Flow For Everyday Living. Upstairs, 4 Spacious Bedrooms Offer Flexibility For Growing Families, Highlighted By A Stunning Primary Retreat With A Walk In Closet And Beautifully Updated Ensuite. The Additional Bedrooms Are Bright, Generous In Size, And Finished With Tasteful Detailing And Neutral Tones. The Fully Finished Lower Level Expands Your Living Space With A Large Recreation Room, Additional Bedroom, And Versatile Space Perfect For A Home Gym, Media Room, Or Guest Suite. Enjoy The Best Of Oakville Living Just Steps To Waterfront Trails, Parks, And Minutes To Vibrant Downtown Shops, Restaurants, And Top Rated Schools.

298 Douglas Avenue, Oakville
$2,990,000
5 Beds ⋅ 4 Baths ⋅ W13533712 MLS
Landmark Old Oakville brick residence fully renovated with newly rebuilt detached coach house with independent accessory dwelling unit. This luxurious dream home features a circular driveway and stately 10'0 ceilings. New wide-plank smoked-oak hardwood throughout. Centre hall plan with dramatic principal rooms. Dining room with fireplace mantle and french doors to front porch. Living room drenched in southwest light with a beautiful wood-burning fireplace. Elegant grand central staircase. Fabulous scale! This is a wonderful home for entertaining. Beautiful white Kitchen with top-of-the-line appliances, quartz counters and large centre island opens to Family Room with gas fireplace and patio doors to the garden. Main floor Den with gas fireplace and built-in bookshelves. Second Floor Laundry. Luxurious Primary Suite with walk-in Dressing Room, private Office/Reading Room and luxury Ensuite Bathroom with radiant heated floors. Three further Bedrooms all a great size and renovated family Bathroom. New central air conditioning and radiant heating. All up-to-date mechanicals and electrical. Newly re-built and renovated detached 2 car heated Coach House Garage with independent second floor apartment with separate entrance featuring a large open plan room with kitchen, 3 piece bathroom, gas heating, central air-conditioning and a wonderful view overlooking the garden. Huge 15,629 Square Foot lot with endless potential including room for a swimming pool. Beautiful circular driveway and parking for 10+ cars. Short-walk to all of Oakville's finest amenities including Downtown Oakville, Lake Ontario, OT Rec Centre & Pool, Tennis Clubs, Sailing Clubs, Oakville GO Station, Whole Foods, Starbucks, LCBO, top schools both public and private & so much more.

349 Trafalgar Road, Oakville
$4,999,000
4 Beds ⋅ 5 Baths ⋅ W13524820 MLS
Grand Grounds. Timeless Elegance. Extraordinary Potential.An exceptional opportunity in one of Olde Oakville's most prestigious neighbourhoods. Tucked behind private gates and nestled beneath a magnificent canopy of mature trees, this beautifully landscaped and increasingly rare 0.82-acre estate offers over 7,100 square feet of living space in an irreplaceable setting just moments from Downtown Oakville.Approached by a sweeping circular drive, the timeless brick residence immediately impresses with its classic Colonial Williamsburg-inspired architecture, elegant symmetry, and commanding presence. Beyond the front entrance, peaceful views of the private pond and lush landscape create a tranquil, park-like retreat rarely found in such a coveted urban location.Custom built in 1980, this stately four-bedroom residence offers an extraordinary opportunity to reimagine an exceptional property. Offered in "as is" condition, the home presents the perfect canvas for those looking to undertake a significant renovation, thoughtfully restore its timeless character, or explore the opportunity to create a magnificent custom estate (subject to all necessary approvals). Whether preserving its enduring architectural charm or designing an entirely new vision, the possibilities are truly exceptional.The expansive grounds provide an incredible backdrop for family living, entertaining, and creating lasting memories for generations to come. Properties offering this rare combination of land, privacy, scale, and location are becoming increasingly difficult to find.Ideally situated within one of Oakville's most sought-after school districts and just a short walk to Downtown Oakville, the Oakville GO Station, public and private schools, Post Park, Whole Foods, Longo's, boutique shopping, restaurants, and the lakefront, this is more than an exceptional property-it is a rare opportunity to create a legacy estate in one of Olde Oakville's most coveted locations.

488 Macdonald Road, Oakville
$2,988,000
3 Beds ⋅ 3 Baths ⋅ W13514262 MLS
Fully renovated luxury home just steps from the boutiques, restaurants, waterfront,and lifestyle amenities of Downtown Oakville. Designed for effortless living, this exceptional residence offers the perfect blend of modern sophistication and low-maintenance convenience.Inside, Cathedral ceilings, premium walnut finishes, engineered hardwood flooring,and skylights create a bright, elegant atmosphere. The chef-inspired kitchen features a high-end Bertazzoni stove and stainless steel appliances, ideal for both everyday living and entertaining. Additional highlights include heated floors, gas fireplaces,a private office, a built-in sound system, and a spa-inspired ensuite.Outside, enjoy beautifully designed maintenance-free grounds, offering year-round enjoyment without the upkeep. A rare opportunity to own a turnkey luxury property in one of Oakville's most sought-after walkable neighbourhoods.

160 Allan Street, Oakville
$3,590,000
6 Beds ⋅ 7 Baths ⋅ W13507594 MLS
This impressive 5,500+ sq. ft. two-and-a-half-storey residence is set back from one of Southeast Oakville's most prestigious streets on an extraordinary 29,000 sq. ft. private, park-like lot backing onto a picturesque creek. Offering over 7,000 sq. ft. of finished living space, with 5+1 bedrooms and 7 bathrooms, this home provides exceptional space, privacy and flexibility for family living and entertainment. The main floor features a beautifully renovated open-concept kitchen (2020) overlooking the living, family and dining areas with W/O to a large deck and spectacular gardens. Additional highlights include a formal dining room, elegant sitting room with a gas fireplace, soaring ceilings, oversized arched windows, a private office, mudroom and powder room.The second level offers three spacious bedrooms, including two with private 2-piece ensuites and backyard views. The third bedroom features a sitting area, double closets and an ensuite with integrated laundry. An office/playroom, walk-in closet and an additional 4-piece bathroom complete this level. The top floor offers two oversized bedrooms connected by a shared 5-piece bathroom.The finished basement includes a spacious recreation area, an additional bedroom, a 3-piece bathroom and two versatile bonus rooms ideal for a home office, gym, hobby space or storage.The private grounds feature mature trees, lush gardens, direct access to a picturesque creek, approximately 9,500 sq. ft. of additional open space for gardens or outdoor entertaining, and a hard-court area perfect for basketball, pickleball or family activities. This exceptional property is within the highly sought-after catchment for Oakville Trafalgar HS, Maple Grove PS and E.J. James PS, and just minutes from St. Mildred's-Lightbourn School and Linbrook School. Walk to grocery stores, cafés, bakeries and restaurants. A rare opportunity to own a spacious family home on an exceptional lot.

480 CHARTWELL Road, Oakville
$2,595,000
3 Beds ⋅ 2 Baths ⋅ W13473380 MLS
Tucked into the coveted Orchard Beach enclave in southeast Oakville and just steps from the lake, 32 Park Avenue is a timeless residence that blends classic charm w/thoughtful modern updates. Set beyond a magnificent magnolia tree on one of Oakville's most desirable streets, this meticulously renovated home offers an exceptional lifestyle in a coveted lakeside setting. Enjoy morning strolls along the Esplanade, peaceful waterfront moments + views of sailboats gliding across the harbour. Inside, light-filled principal rooms unfold w/warmth and sophistication. The chef's kitchen is beautifully appointed with commercial grade appliances, Carrara marble countertops, slate flooring + Perrin & Rowe fixtures. Designed for both everyday living + entertaining, it flows seamlessly into the dining room + inviting living room. A glass-enclosed sunroom overlooks the gardens + is warmed by a gas stove, creating a tranquil retreat that can be enjoyed year-round. Upstairs, three generous bedrooms are served by a beautifully renovated four-piece bath. The primary bedroom enjoys access to a private terrace, offering a peaceful setting for morning coffee or quiet relaxation. The finished lower level extends the living space with a welcoming recreation room, gas fireplace, bar area + custom walnut-and-glass wine display. Outside, mature magnolias, Japanese maples, rhododendrons, hemlocks + moonbeam plantings create an enchanting English garden setting. Curated landscaping lighting + frequent visits from songbirds enhance the sense of serenity. Offering a rare blend of tranquillity + convenience, this exceptional property is just a short stroll to downtown Oakville's boutiques, cafes, restaurants, parks, harbour + waterfront trails, with GO Transit and top-ranked schools close at hand. Rarely does an opportunity arise in this prestigious lakeside pocket. Elegant, welcoming + undeniably special, this is Orchard Beach living at its finest.

32 Park Avenue, Oakville
$4,265,000
5 Beds ⋅ 6 Baths ⋅ W13469458 MLS
A rare opportunity to create a new, luxurious custom-home on one of Old Oakville's most coveted streets, set on an exceptionally private, tree-lined lot. This rarely offered design features a double-car garage and a fully finished lower level, thoughtfully crafted to deliver both elegance and functionality. Enjoy the expertise of a dedicated interior designer throughout the entire building process, ensuring every finish and detail is tailored to your vision. Features include: Curated luxury finishes throughout. Personalized interior design consultation and selection services. Optional elevator upgrade available with a three bedroom floorplan. Exceptional craftsmanship by a trusted custom builder with nearly 20 years of experience. An extraordinary opportunity to build a timeless custom home in one of Oakville's most prestigious neighbourhoods. Drawings are approved by Committee of Adjustments. Projected completion date August 2027 /Permit Process Underway

343 Douglas Avenue, Oakville
$10,900,000
5 Beds ⋅ 5 Baths ⋅ W13430514 MLS
Nestled in the heart of downtown Oakville, this magnificent historical home offers unparalleled charm and elegance, combined with modern amenities. Spanning over 8,000 square feet, the expansive layout provides both grandeur and comfort, perfect for family living or entertaining on a grand scale. With stunning views of the sparkling waters of Lake Ontario, every room is designed to maximize the beauty of its lakeside setting. The home boasts high ceilings, intricate architectural details and walnut hardwood floors, blending timeless craftsmanship with contemporary design. The private lush yard with 104 feet of frontage is a rare gem, providing a serene outdoor oasis with mature trees and ample space for outdoor activities or quiet relaxation and complete privacy. Whether you're enjoying a morning coffee while gazing at the lake or hosting a summer gathering, the outdoor space is as inviting as the interiors. The property's prime location puts you just steps from Oakville's charming downtown, offering convenient access to world-class dining, shopping, and cultural attractions, while still providing the tranquility of lakeside living. With its rich history, extraordinary space, and unbeatable location, this is a once-in-a-lifetime opportunity to own a piece of Oakville's heritage.

350 King Street, Oakville
$2,999,999
5 Beds ⋅ 2 Baths ⋅ W13423850 MLS
Rare opportunity in coveted Orchard Beach, just steps from Lake Ontario and the waterfront trail. Set on a premium 50 x 160 ft lot, this property comes with completed architectural and engineering drawings and Committee of Adjustment approval for a proposed 3,800 sq ft residence. An exceptional offering for a buyer looking to move forward with confidence, with extensive completed work including floor plan and exterior concepts, colour renderings, arborist report, architectural drawing package, sealed roof truss package, sealed LVL layout, sealed structural engineering package, HVAC design, grading and drainage plan, soil test, and stormwater management report.The existing home was updated in 2024 with electrical improvements, a renovated bathroom, updated flooring, a new kitchen, and new appliances, offering flexibility to live in or hold the property while completing the final permit stage. Zoning and Committee of Adjustment approvals are already in place, with remaining steps in progress. Located a short stroll from downtown Oakville, the lake, and top schools, this is a rare opportunity to secure a prime property with meaningful value already created.

25 Howard Avenue, Oakville
$2,999,000
5 Beds ⋅ 3 Baths ⋅ W13291708 MLS
Nestled in Southeast Oakville, this beautifully renovated heritage home on Palmer Avenue offers timeless character, modern comfort and an exceptional lifestyle on a premium south-facing lot. Thoughtfully updated while preserving its architectural charm, the residence is filled with natural light and enjoys seamless connections to its private outdoor living spaces. The expansive south-facing backyard is a true retreat, featuring two spacious decks that provide multiple areas for entertaining, and relaxing while overlooking the mature grounds. Inside, the home blends heritage elegance with contemporary functionality. The welcoming great room is anchored by rich plank flooring and a stunning Rumford fireplace, creating a warm and sophisticated atmosphere for everyday living. The kitchen showcases clean lines and timeless design, complemented by a practical rear pantry hallway offering exceptional storage and organization. Large principal living and dining rooms provide generous space for formal entertaining while maintaining a sense of comfort and flow throughout the main level. The upper level offers four bedrooms, including a primary suite that features a Rumford fireplace, walk-in closet and a five-piece ensuite and laundry room The additional large fifth bedroom is on the main floor providing flex space for guests or home office. The finished lower level extends the living space with versatile area ideal for recreation, fitness, media or play, ensuring ample room for every stage of family life. Recent mechanical updates provide peace of mind, including a new furnace, owned hot water tank and central air conditioning. Combining heritage character, thoughtful renovations and an exceptional location in one of Oakville's most established neighbourhoods, this distinguished property offers a rare opportunity to enjoy sophisticated family living just moments from the lake, top-ranked schools, parks, shopping and the vibrant amenities of downtown Oakville.

332 Palmer Avenue, Oakville
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