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6 Chartwell Road in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40749379
6 Chartwell Road Oakville L6J 3Z4 
$7,850,000Residential- Status:
- Active
- MLS® Num:
- 40749379
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 5,051 sq. ft.
Lakefront Elegance in the Heart of Old Oakville! Welcome to an exceptional waterfront residence that defines refined lakefront living. Nestled at the foot of prestigious Chartwell Road, this private and serene estate offers the rare blend of Muskoka-like tranquility with the convenience of being just moments from the heart of downtown Oakville.Completely reimagined with a recent masterful renovation inside and out, this home has been thoughtfully curated under the direction of acclaimed architect & designer Rodney Deeprose, and constructed by the esteemed Horne Construction. Every detail exudes elevated taste, from the marble inlay foyer and double-sided stainless steel fireplace to the carefully selected finishes throughout.The open-concept main floor is flooded with natural light, thanks to a dramatic wall of Kolbe windows that frame breathtaking lake views. Designed for both grand-scale entertaining and intimate family gatherings, the space flows seamlessly through the principal rooms. The gourmet kitchen is a showpiece, featuring Cambria quartz surfaces, Bloomsbury cabinetry, premium appliances, a walk-in pantry, and a fully equipped servery.The principal suite is a sanctuary unto itself—wake to unobstructed lake views, enjoy morning coffee and unwind in the luxurious 5-piece spa-inspired ensuite with heated floors and oversized walk-in California Closet. A screened sunroom, accessed directly from the suite, provides a peaceful space to enjoy the sights and sounds of the lake year-round.Two additional spacious bedrooms, designer-appointed main bath, and a large laundry complete the second level. The professionally finished lower level offers a generous recreation space, fourth bedroom, and a full 4-piece bathroom featuring a steam shower—perfect for guests or extended family.Outside, an expansive stone patio with gas fireplace extends your living space practically to the waters edge with gated rear entrance to trail access. Generous garage with loft! More detailsListed by Century 21 Miller Real Estate Ltd.- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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31 Ridge Drive in Oakville: 1003 - CP College Park Single Family Residence for sale (1 - Oakville) : MLS®# 40749372
31 Ridge Drive Oakville L6H 1B7
$1,799,988Residential- Status:
- Active
- MLS® Num:
- 40749372
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 3,548 sq. ft.
CUSTOM BUILT DETACHED HOUSE WITH SALT WATER INGROUND POOL IN THE DESIREABLE COLLEGE PARKNEIGHBOURHOOD. Step inside to main 9ft smooth ceilings, crown molding, and California shutters throughout. The main floor boasts a grand living room with bay window and waffle ceilings, a feature echoed in the dining and family rooms. The extended kitchen is a chef's dream with elegant white cabinets, quartz counters and backsplash, stainless steel appliances, and a wide island perfect for entertaining. From here, walk out to your private backyard oasis, where bird song is your daily summer soundtrack. The family room, open to the kitchen, invites relaxation with a gas fireplace, accent stone wall, and coffered ceiling with LED lighting. Upstairs, discover a tranquil retreat. The primary suite features a generous 7Ft. X 10Ft.walk-in closet and a 5PC ensuite with a Jacuzzi tub, his/her sinks, and heated floors. All upstairs bathrooms enjoy the comfort of heated floors, and a newer skylight bathes the space in natural light. Convenience is key with an upstairs stacked Maytag laundry. Outside, the stone and stucco exterior with a metal roof and exterior pot lights exudes curb appeal. The interlocked driveway accommodates three cars, plus two in the tiled, oversized garage (19Ft. X 21Ft.) with four access points. Your backyard is a meticulously landscaped haven with interlocked stones, mature trees, a concrete side sitting area, and a salt water pool with upgraded 2021 equipment. Updated Vinyl Fence for privacy A finished basement with a separate entrance offers a versatile studio apartment setup, complete with a full kitchen, 3PC ensuite, separate laundry, and ample storage in the 26Ft. by20Ft. crawl space. Located on a quiet street surrounded by custom homes, this property is designed for those who appreciate refined elegance and thoughtful details. This exceptional home promises not just a residence, but a lifestyle. Are you ready to discover your dream home in Oakville? More detailsListed by ROYAL LEPAGE IGNITE REALTY- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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63 Washington Avenue in Oakville: 1002 - CO Central Single Family Residence for sale (1 - Oakville) : MLS®# 40746875
63 Washington Avenue Oakville L6K 1W5
$979,999Residential- Status:
- Active
- MLS® Num:
- 40746875
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 933 sq. ft.
Detached Bungalow in desirable Kerr Village. Close to shops, restaurants, movie theatre, parks, waterfront trails, public transit and GO Train station. Great investment opportunity for handyman to renovate, or build your dream home here! New white kitchen cupboards June 2025, New eavestrough 2024. New siding on Mudroom 2024. Oil tank removed. Heating currently electric baseboard (2 rooms), and radiator electric. Updated roof shingles 2015. Living Room and Dining Room plaster ceilings redone 2015. Master bedroom ceiling redone 2025. Flexible closing date. Great property for local builder/construction of new home in Kerr Village. More detailsListed by Century 21 Miller Real Estate Ltd.- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
- 1 (905) 510-7141
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404 185 Robinson Street in Oakville: 1013 - OO Old Oakville Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40744077
404 185 Robinson Street Oakville L6J 7P6
$699,000Residential- Status:
- Active
- MLS® Num:
- 40744077
- Bedrooms:
- 1
- Bathrooms:
- 1
- Floor Area:
- 762 sq. ft.
Welcome to Ashbury Square in the heart of Downtown Oakville. This stylish two-storey loft-style condo offers just over 760 square feet of beautifully designed living space with soaring ceilings and abundant natural light. The open-concept main floor features an updated kitchen and stainless steel appliances, hardwood floors, and a dedicated office or den area—ideal for working from home. Upstairs, the spacious lofted bedroom includes a walk-in closet and views to below Step outside and you’re in the vibrant core of Downtown Oakville—surrounded by boutique shops, award-winning restaurants, cozy cafés, and just steps to the lake, the marina, and scenic waterfront trails. Enjoy refined urban living in one of Oakville’s most coveted, walkable neighbourhoods. Includes underground parking and locker. More detailsListed by RE/MAX Aboutowne Realty Corp.- STEVE WILLIAMSON
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44 Head Street in Oakville: 1002 - CO Central Single Family Residence for sale (1 - Oakville) : MLS®# 40743508
44 Head Street Oakville L6K 1L5
$2,699,000Residential- Status:
- Active
- MLS® Num:
- 40743508
- Bedrooms:
- 4
- Bathrooms:
- 5
- Floor Area:
- 3,198 sq. ft.
Welcome to 44 Head St - an exceptional home in the heart of Oakville- steps from Kerr Village & downtown. Enjoy walkable access to local shops, dining & the lakefront-the perfect blend of convenience & tranquility. Offering almost 2200 sq ft plus fully finished basement ( 1015 sq ft), this remarkable residence offers timeless charm & modern functionality. Set behind pretty gardens, the Dark Slate wood siding & crisp white trim frame an inviting front porch-perfect for morning coffee or evening wine. Inside, 9' ceilings, hardwood floors, crown moulding & high baseboards create a refined, elevated feel. The entertainer’s kitchen showcases granite countertops, a large island, professional-grade appliances & generous storage, seamlessly flowing into the bright, open-concept living & dining areas. A cozy gas fireplace with custom millwork adds warmth, while French doors lead to the beautifully landscaped rear garden-perfect for relaxing or hosting outdoors. A versatile room on the main floor can serve as your personal office or den; it could also be transformed into a separate dining room if desired. Upstairs are 3 spacious bedrooms, each with ensuites with heated floors & walk-in closets . The lower level (9’ ceilings) includes a spacious family room plus 4th bedroom, 3pc bath & large laundry room. Storage is no issue in this home with the many custom built-in closets & cabinets. A detached garage with EV charger features a rare basement for even more storage! Plus there is parking for 6 cars on the extra long driveway. A fully fenced private rear yard, & unbeatable walkability to parks, shops, cafés & the waterfront make this turnkey property a rare offering. Meticulously maintained by the current owners, recent updates include powder room renovation (2024), driveway resurfaced (2024), exterior newly stained (2024) & insulation upgraded to R60 (2025). Ideal for empty nesters, downsizers & families. Don’t miss this opportunity to experience Oakville’s historic charm. More detailsListed by RE/MAX Aboutowne Realty Corp.- STEVE WILLIAMSON
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262 Mary Street in Oakville: 1020 - WO West Single Family Residence for sale (1 - Oakville) : MLS®# 40737290
262 Mary Street Oakville L6K 3V4
$2,980,000Residential- Status:
- Active
- MLS® Num:
- 40737290
- Bedrooms:
- 6
- Bathrooms:
- 5
- Floor Area:
- 4,383 sq. ft.
A Bold Statement In Design And Personality, This One-Of-A-Kind Art Deco-Inspired Home Is A Celebration Of Creativity, Quality, And Individuality. With Premium Finishes And Enduring Materials Throughout, This Residence Blends Luxury With Architectural Craftsmanship. The Exterior Features A 50-Year Metal Roof, Custom Concrete Driveway With Grass Inserts, Cedar And IPE Wood Façade, And Cedar-Lined Porch Ceiling. The Private Backyard Is Professionally Landscaped With Mature Trees, Perennial Gardens, Four Varieties Of Fruit Trees, Putting Green, Solarium (Updated With High-Efficiency Windows In 2019), Natural Gas BBQ Hookup, And Custom Garden Structures. Inside, The Heart Of The Home Is The Chefs Kitchen Which Impresses With 12 Built-In Miele Appliances, A 14-Ft Caesarstone Island, Custom Cabinetry, 3 Sinks, KOHLER Faucets, Pot Filler, In-Floor Heating, And Italian Tile. The Family Room Includes A Gas Fireplace And Surround Sound. The Foyer Welcomes With Granite Floors, A Glass/Stainless-Steel Staircase With Sapele Treads And Imported Designer Lighting. Formal Living And Dining Rooms Feature Crown Moulding, Custom Glass Pocket Doors, And A Stainless-Steel Fireplace. Upstairs, 5 Bedrooms Offer Bamboo Floors And Custom Lighting. The Primary Suite Has Mirrored Closets And A Bright Ensuite With Jacuzzi And Separate Shower. The Walk-Out Lower Level Offers A Private Entrance, Steam Shower, Rec Room, Home Office, And In-Law Suite Potential. Walk To Top Schools (Including Appleby College And French Immersion), Transit, Downtown, And The GO. A Rare Offering That Seamlessly Blends Design, Lifestyle, And Location - This Home Is Truly One To Experience. More detailsListed by The Agency- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
- 1 (905) 510-7141
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417 185 Robinson Street in Oakville: 1013 - OO Old Oakville Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40743832
417 185 Robinson Street Oakville L6J 7P6
$850,000Residential- Status:
- Active
- MLS® Num:
- 40743832
- Bedrooms:
- 1
- Bathrooms:
- 2
- Floor Area:
- 1,029 sq. ft.
This exquisite two-story penthouse in "The Ashbury," adjacent to the picturesque Town Square, epitomizes the pinnacle of luxurious living in the heart of Old Oakville. Its prime location offers unparalleled convenience, with effortless access to upscale restaurants, boutique shops, theatres, the serene lake, and the charming harbour, all immersing you in the town's vibrant and sophisticated ambiance. The expansive open-concept floor plan seamlessly integrates the living and dining areas, creating an opulent and inviting atmosphere, further enhanced by vaulted ceilings that amplify the sense of grandeur. The state-of-the-art kitchen boasts pot lights, a centre island, premium LG stainless steel appliances, and quartz countertops, providing a culinary haven. The living room, dining room, and den all share this elegant open-concept design, with the versatile dining room, which can double as a second bedroom, featuring a chandelier, sliding glass wall, and custom built-in shelving. The laundry area includes a stackable washer and dryer and built-in shelves for added convenience. Ascending to the second floor, the loft-style primary bedroom exudes sophistication with pot lights, his and her closets, and a lavish ensuite that includes a 4-piece bathroom with a tub/shower combo. An open-concept office completes the upper level, providing a perfect workspace. Residents of "The Ashbury" enjoy exclusive access to a stylish party room and a tranquil private garden, along with the added luxury of one underground parking space and a secure locker. More detailsListed by Royal LePage Real Estate Serv.- STEVE WILLIAMSON
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LOT 101 Douglas Avenue in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40743516
LOT 101 Douglas Avenue Oakville L6J 2B7
$4,290,000Residential- Status:
- Active
- MLS® Num:
- 40743516
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 3,188 sq. ft.
Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. The Douglas Collection is an extension of the inaugural development with an exclusive collection of seven homes located on Douglas Avenue. Distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. "The Chatsworth"; detached home with 48-foot frontage, between 3,188-3,204sf finished space w/an additional 1,000+sf (approx)in the lower level & 4beds & 3.5 baths. Utility wing from garage, chef’s kitchen w/w/in pantry+ generous breakfast, expansive great room overlooking LL walk-up. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment. More detailsListed by Century 21 Miller Real Estate Ltd.- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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LOT 102 Douglas Avenue in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40743594
LOT 102 Douglas Avenue Oakville L6J 2B7
$4,166,000Residential- Status:
- Active
- MLS® Num:
- 40743594
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 2,974 sq. ft.
Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. The Douglas Collection is an extension of the inaugural development with an exclusive collection of seven homes located on Douglas Avenue. Distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. "The Regal"; detached home with 48-foot frontage, between 2,974-3062 sf of finished space w/an additional 1,000+sf (approx) in the lower level & 4beds & 3.5 baths. Utility wing from garage, chef’s kitchen w/w/in pantry+ generous breakfast, expansive great room with glass sliders to rear patio. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment. More detailsListed by Century 21 Miller Real Estate Ltd.- STEVE WILLIAMSON
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901 55 Speers Road in Oakville: 1002 - CO Central Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40743275
901 55 Speers Road Oakville L6K 0H9
$529,000Residential- Status:
- Active
- MLS® Num:
- 40743275
- Bedrooms:
- 1
- Bathrooms:
- 1
- Floor Area:
- 650 sq. ft.
Discover modern elegance in this upgraded 1+den, 1-bath condo, offering just over 650 sq. ft. of stylish living space in the heart of Oakville’s trendy Kerr Village. Boasting over $35,000 in updates, this bright unit features brand-new appliances, including a fridge, dishwasher, stove, washer, dryer, and microwave, alongside a custom-designed island and bar area with quartz countertops extending into a seamless backsplash. The kitchen is further enhanced with upgraded handles, while the bathroom showcases a luxury vanity countertop. Custom storage solutions in all closets, fresh paint, and upgraded light fixtures elevate the space, complemented by floor-to-ceiling windows that fill the unit with natural light. A sprawling balcony, spanning the entire length of the condo, offers a perfect spot for relaxation or entertaining. Located steps from boutique shops, trendy cafés, and vibrant community amenities, this move-in-ready gem delivers a chic lifestyle in an unbeatable location. More detailsListed by RE/MAX Escarpment Realty Inc.- STEVE WILLIAMSON
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382 Trafalgar Road in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40739852
382 Trafalgar Road Oakville L6J 3H5
$4,200,000Residential- Status:
- Active
- MLS® Num:
- 40739852
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 2,890 sq. ft.
Exquisite and reminiscent of New England charm, this lofted bungalow offers breathtaking views and unmatched privacy along Oakville's 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. In winter, skate or ski on the frozen creek or admire the snowy landscape from your sun-drenched living room. In summer, swim, fish, paddle to Oakville Harbour, or relax by the water, this home offers the feel of Muskoka, right in the city. 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. More detailsListed by Royal LePage Real Estate Serv.- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
- 1 (905) 510-7141
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1 288 Reynolds Street in Oakville: 1013 - OO Old Oakville Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40743027
1 288 Reynolds Street Oakville L6J 3L4
$430,000Residential- Status:
- Active
- MLS® Num:
- 40743027
- Bedrooms:
- 2
- Bathrooms:
- 1
- Floor Area:
- 750 sq. ft.
Welcome to carefree, low-maintenance living in the heart of historic Old Oakville. This beautifully updated 2-bedroom apartment in the boutique Mayfair co-operative building offers a bright, inviting space ideal for those looking to downsize without compromise. Located on a quiet street just steps from charming downtown shops, restaurants, the lakefront, and the brand-new Oakville Trafalgar Community Centre, this home blends convenience, comfort, and community. Inside, you’ll find a thoughtfully renovated kitchen with stainless steel appliances, under-cabinet lighting, and a sleek, modern feel. The updated bathroom, newer energy-efficient windows, and durable pale wood grain flooring throughout add style and ease. Large windows flood the unit with natural light and offer views of the building’s lush, professionally maintained perennial gardens. This self-managed co-op includes a dedicated parking spot, storage locker, on-site laundry, and the option for garage rental. Monthly fees cover property taxes, heat, water, and parking — keeping costs predictable and hassle-free. Pride of ownership is evident throughout the building, thereby creating a strong sense of community and helping maintaining value for all. If you’re looking for a peaceful adult lifestyle in a walkable, established neighbourhood with great transit connections, this rarely offered co-op is a true gem. More detailsListed by RIGHT AT HOME REALTY BROKERAGE- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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Data was last updated July 11, 2025 at 01:50 AM (UTC)
Steve Williamson
Oakville ON REALTOR® - Call 905-510-7141 today
Location
A - 309 Lakeshore Road East
Oakville, ON, L6J 1J3