116 Chartwell Road

A rare opportunity to own an estate property on one of Old Oakvilles most prestigious streets. Set on an oversized 100' x 171' lot, this David Small-designed home offers over 8,000 square feet of finished living space, ideal for modern family living and entertaining. Just a short walk to downtown Oakville and minutes to the GO Train, Whole Foods, Longos, and top-ranked schools, this home offers both convenience and privacy. Surrounded by mature trees, the property sits on a quiet, established street. Inside, the double-height foyer opens to formal living and dining rooms. The main level features oversized principal rooms with vaulted ceilings. The chefs kitchen flows into the family room and includes a large island, premium appliances, and custom cabinetry. A mudroom with front and rear access, a secondary powder room for pool use, and main floor laundry add everyday practicality. Upstairs, the primary suite offers a spa-like ensuite with steam shower and soaker tub. Three additional bedrooms include ensuite access and ample closets. A second-floor family room offers flexible space for growing families. The finished basement includes a large recreation room, games area with wet bar, oversized wine cellar, newly finished gym, fifth bedroom, and full bathroom. Outside, the private backyard is fully landscaped with a pool, retractable cover, hot tub, covered lounge, and built-in outdoor kitchenideal for relaxing or entertaining. With parking for six vehicles and an oversized double garage, this is a timeless family home in one of South Oakvilles most desirable locations.

Nestled behind private gates on one of Oakville's most coveted "Street of Dreams," this exceptional estate sits on a spectacular 100 x 225 ft lot and offers over 7,500 sq ft of luxurious finished living space. Surrounded by manicured gardens and mature trees, the home blends timeless architecture with sophisticated, on-trend finishes and commanding curb appeal. A grand double-height foyer introduces an elegant interior designed for refined living and effortless entertaining. The main level features a chef-inspired kitchen with custom cabinetry, seamlessly open to a spacious family room. A private office, formal living room, piano lounge, and a stunning three-season Muskoka room extend the living space into the tranquil backyard. Upstairs, the luxurious principal retreat showcases a sleek linear gas fireplace, dual spa-inspired ensuites, separate walk-in closets, and a boutique-style dressing room, with a private balcony overlooking the Muskoka-like setting. Three additional bedrooms each offer private ensuites and generous custom closets for ultimate comfort and privacy. The fully finished lower level-accessible by both the main staircase and a unique main-floor slide-offers expansive recreation and games areas, a theatre, gym/fifth bedroom, full bath, and abundant storage. Two laundry rooms provide exceptional convenience for modern family living.Since 2025, the owner has invested significantly in premium upgrades, including enhancements to the kitchen cabinetry, custom closet built-ins, lower-level laundry room, fireplaces in the living and family rooms, window treatments, appliances, primary dressing area, and multiple bathrooms-further elevating the home's quality and turnkey appeal. A rare opportunity to own a gated estate of scale, elegance, and enduring value in prestigious S.E Oakville.

Welcome to this architecturally crafted masterpiece tucked away on a quiet court south of Lakeshore Road, in one of Oakvilles most prestigious and serene neighbourhoods. Just a short walk to the shores of Lake Ontario and the renowned Appleby College, this exceptional executive residence offers over 8,200 sq.ft. of finished living space, seamlessly blending luxury, functionality, and timeless elegance.Designed for upscale living and entertaining, the home boasts a gourmet open-concept kitchen with top-of-the-line appliances, and a soaring 20 cathedral ceiling in the great room with double French doors opening to a beautifully landscaped, private backyard. Complete with a built-in outdoor kitchen island and BBQ grill station, the backyard is perfect for summer gatherings, outdoor dining, or relaxing in style. Two main-floor offices/libraries are ideal for professionals working from home.The primary suite offers a peaceful retreat with a balcony overlooking the yard, an expansive custom walk-in closet, and a spa-inspired ensuite. All secondary bedrooms are oversized with their own ensuites, and a 2nd-floor laundry adds convenience. The sun-filled walkout basement (approx. 2,925 sq.ft.) features a home theatre, fifth bedroom, and flexible living space suitable for a nanny suite or multi-generational setup. Additional highlights include a double garage with extra side storage and a private driveway for 10+ cars.Minutes from Downtown Oakville, residents enjoy quick access to the Oakville Club, Appleby College, top-rated schools, lakeside trails, fine dining, boutique shopping, major highways, and the GO Stationmaking this an unparalleled rental opportunity in one of Oakvilles most coveted lakefront communities.

Set on a commanding 112.5'x199.5' lot just steps from the lake, this custom modern-traditional estate offers nearly 11,000SF of finished living space across three levels. A long private drive with parking for up to 12 cars and oversized 3-car garage create a striking arrival, complemented by stone and stucco architecture, soffit lighting, and professionally landscaped grounds. A dramatic double-height foyer introduces the home's scale, anchored by an open-riser staircase with smoked glass panels and integrated lighting. Principal rooms feature tile inlaid borders, herringbone engineered hardwood flooring, oversized windows, and sleek architectural lighting. The chef's kitchen is centred around a 10' quartz island with premium Thermador appliances, bespoke cabinetry, and a dedicated coffee station, flowing seamlessly into the family room with a modern fireplace feature wall, built-in media cabinetry, and multiple walkouts to a covered portico designed for four-season entertaining. A private main-floor office with double French doors and its own exterior entry offers exceptional work-from-home flexibility. Upstairs, four bedroom suites include a luxurious primary retreat with dual walk-in closets and a spa-inspired ensuite featuring a steam shower, freestanding tub, wall-mounted fixtures, and heated floor. The walk-up lower level is designed for lifestyle living with radiant in-floor heating, theatre room, wet bar, glass-enclosed gym, guest suite, pet spa, and extensive storage. Outdoor living is elevated with a rectangular pool and water feature, large-format stone terraces, composite sun deck, covered outdoor fireplace wall with TV rough-in, built-in BBQ station, and pool-house. Smart home technology, multi-zone audio, dual HVAC systems, and security surveillance complete this exceptional Lakeshore Road offering near parks, trails, and Bronte amenities. An outstanding blend of architectural presence, scale, and resort-style living! (some images have virtual staging)

Welcome to 1260 Braeside Drive, a distinguished custom-built luxury residence located in the prestigious Morrison neighborhood of South East Oakville. Situated on a premium, tree-lined lot this exceptional home offers over 7,000 square feet of thoughtfully designed and carefully crafted family living space. This home is highlighted by the large windows that provide beautiful views of mature trees, allowing natural light to fill the space throughout the day and creating a seamless indoor-outdoor living environment.Constructed with enduring elegance and equipped with advanced smart home technology, this architectural masterpiece features 10-foot ceilings, wide-plank engineered hardwood flooring, and a striking two-storey dining area that enhances the sense of openness and light. The open-concept gourmet kitchen, complete with a wrap-around pantry, is ideal for entertaining and includes custom full-height cabinetry, a spacious quartz island, and high-end Wolf and SubZero appliances. Upstairs, the luxurious primary suite offers a spa-inspired ensuite with heated floors, a soaking tub, and a custom walk-in closet. Three additional bedrooms, each with private ensuite bathrooms, office, and a generously sized laundry room provide excellent comfort and functionality for family living. The lower level is equally impressive, boasting a home theater, gym, wet bar with a full-sized refrigerator and professional wine storage fridge, and a stylish recreation area with a modern fireplace. Additionally, the basement has a bonus bedroom with a private ensuite and radiant heated floors for added comfort.1260 Braeside Drive offers more than just a home, it provides a comfortable and sophisticated lifestyle. Located in a quiet, family-oriented neighborhood, just minutes from top-rated schools, the lakefront, and downtown Oakville, this rare opportunity in one of the GTAs most sought-after communities is truly worth experiencing firsthand.

This exceptional estate exemplifies timeless European elegance and modern sophistication in a most coveted prestigious enclave of S.E Oakville within walking distance to the lake and downtown.Designed by Bill Hicks, this custom home offers approximately 9,200 sq.ft. of premium living space across all levels. Built to the owner's highest standards, this masterpiece features an elevator, full power generator, and a 3-car heated garage with heated driveway.The main level showcases herringbone walnut floors,10ft soaring ceilings, and elegant large principal rooms with a hand-carved marble fireplace mantel, a 600+sqft great room could be used as a ballroom for larger entertaining. The chef-inspired kitchen boasts top-of-the-line Wolf/Subzero/Miele appliances, custom cabinetry, and an expansive center island. The primary suite is a private retreat with a luxurious 6-piece ensuite under an artistic glass dome skylight, opulent dressing room, and walk-out terrace.The finished lower level offers a recreation room, theatre, second kitchen, and a nanny suite-ideal for extended family. Enjoy outdoor living on the stone patio and covered porch with gas fireplace, surrounded by professionally landscaped grounds. State-of-the-art mechanicals include radiant heating in the garage, basement, and driveway.

WATERFRONT PROPERTY! Experience the Beauty of Lakeside Living. Perfectly situated on a premium 90' x 152' lakefront lot, this residence captures breathtaking, unobstructed water views from every principal room. Offering over 5,700 square feet of finished living space, the home seamlessly blends timeless lakeside elegance with modern comfort and functionality. Step inside to discover a light-filled interior where functionality meets everyday comfort. Rich hardwood flooring, limestone tiles, and four skylights create a warm and inviting ambiance throughout. Designed with both family living and entertaining in mind, the main level features two spacious family rooms, a private office, and a gourmet kitchen complete with granite countertops, premium appliances, and abundant cabinetry. Upstairs, four generously sized bedrooms offer space and privacy for the entire family. The primary suite is a true retreat, showcasing spectacular lake views. A convenient upper-level laundry room adds to the home's thoughtful design and a walkout to the second-floor terrace - the perfect place to unwind and enjoy tranquil sunsets over the water. The fully finished lower level extends the living space, featuring a fifth bedroom with a private ensuite - ideal for guests, in-laws, or a nanny suite. Outdoors, the backyard is an entertainer's dream. Featuring the concrete saltwater in-ground pool, landscaped gardens, and multiple seating areas designed to make the most of the home's stunning lakefront setting. Whether hosting summer gatherings or relaxing quietly by the water, this space offers a waterfront lifestyle experience. Additional highlights include a three-car garage, four fireplaces, an irrigation system, and ample storage throughout. This property embodies the very best of lakeside living - offering endless possibilities for its next owner to further enhance and celebrate the home's inherent beauty, and sophisticated waterfront setting. Luxury Certified.

With a stunning backyard, 5,196 sq ft of above ground living, and quality construction built by Gatestone Homes, this home is truly the total package. Stone, wood, and striking Anderson windows have been eloquently incorporated on the exterior of the home, lending to the superb curb appeal. The thoughtful design fuses modern style with timeless elegance. The foyer of the home feels as though you are entering a luxury hotel, with a stunning floating staircase and a custom hanging light feature that is a piece of art in itself! The soaring two-storey foyer is flooded with natural light from oversized windows, creating a bright and welcoming space. A custom wooden piece subtly divides the foyer from the traditional dining room that is complete with a temperature-controlled wine room and glass doors that invite you to enjoy the expansive rear deck. The heart of the home is the open concept kitchen-family-dining space that is surrounded by windows and grounded by a beautiful gas fireplace. With an oversized island there is no shortage of space for you and your guests. Adjacent to the kitchen is a conveniently located powder room as well as a laundry/mudroom that can be concealed by a pocket door. The primary suite is a true oasis. With double door entry, a gas fireplace, and five-piece ensuite, no detail was overlooked. The three additional bedrooms all have ensuite access and walk-in closets. Completing this level is a laundry room and study area with built-in desk space. The 2,712 sq ft lower-level walk-up will not disappoint. The large recreation space features a built-in projector, billiards space, and wet bar. A home gym and two additional bedrooms as well as playroom/second home office finish off this space. Lush mature trees combined with meticulous landscaping will lure you to the rear yard. With approx. 1800 sq ft of outside living space, a gunite pool, and cabana, this backyard checks all the boxes! Enjoy the beautiful summer weather in this retreat-like home!