Welcome to 304 Winston Rd, an exceptional custom-designed and built residence offering 5897 sq ft of total living space in one of Oakville's most prestigious neighbourhoods. Perfectly positioned on a premium lot just a few minutes walk to Appleby College, this spectacular home blends timeless transitional architecture with sophisticated finishes, modern smart-home technology, and luxurious resort-inspired living.The exceptional backyard is an outdoor retreat featuring custom infinity edge saltwater pool and hot tub surrounded by expansive entertaining areas. Enjoy indoor-outdoor living beneath the covered rear porch complete with built-in automated screens, fireplace and TV allowing for enjoyment well into the shoulder seasons. Integrated security cameras, advanced Control4 automation, and a dedicated Generator provide added convenience, comfort, and peace of mind. Inside, the home exudes warmth and sophistication. The thoughtfully designed layout offers exceptional versatility, highlighted by a rare main floor primary complete with a luxurious ensuite bath and walk-in closet. An integrated elevator provides ease with access to all levels of the home. With 4+1 bedrooms and 5.5 baths, the residence is perfectly suited for families of all sizes. Two separate laundry rooms further enhance the home's everyday practicality and convenience. The fully finished lower level has been meticulously designed for year-round enjoyment featuring radiant heated floors throughout for exceptional comfort. This impressive space includes a home theatre, gym, rec area, guest/nanny suite & ample storage. Combining luxurious amenities, timeless design, and an unbeatable South Oakville location close to top-ranked schools, parks, waterfront trails, and everyday conveniences, 304 Winston Rd. presents an extraordinary opportunity to experience refined custom living in one of the town's most sought-after communities.More details
Situated within prestigious Morrison in South East Oakville, this exceptional modern custom residence is located in one of the area's most desirable communities, known for its mature tree-lined streets, highly regarded schools and close proximity to some of the region's finest private schools. Backing onto Wedgewood Creek ravine with prized southwest exposure, the property enjoys remarkable privacy, beautiful natural surroundings and abundant natural light throughout the day. Offering over 4,600 sq. ft. of finished living space, the home blends contemporary architecture with thoughtful everyday functionality. An impressive open-to-above foyer and staircase create a dramatic sense of arrival, while expansive windows, elegant glass railings and custom millwork establish a refined modern atmosphere throughout. Designed for family living and entertaining, the main level features bright open spaces centred around a chef-inspired kitchen with an oversized island, marble feature wall, appliance garage and premium integrated Sub-Zero, Wolf and Miele appliances. Floor-to-ceiling windows connect the interior with the surrounding landscape, while a sleek built-in gas fireplace anchors the living area. Radiant heated flooring extends throughout all three levels. The home offers five spacious bedrooms, each with its own ensuite bathroom, including a luxurious primary retreat with a spa-inspired six-piece ensuite and custom walk-in closet. The fully walk-out lower level extends the living space with expansive recreation and entertaining areas, custom wet bar and direct backyard access. Outdoor spaces include an upper terrace, covered patio areas and a private backyard setting surrounded by mature trees and ravine views. A rare opportunity to enjoy modern architecture, exceptional functionality and a remarkable natural setting in one of Oakville's most sought-after neighbourhoods.More details
Rare Creemore countryside estate set amid the rolling hills with Amazing views Situated on beautiful 104 acre (85+ tillable) enjoying backdrop of the Niagara Escarpment, serene pastoral countryside sunsets/nightsky this exceptional property offers both rural charm & versatile potential. Zoned Agri/Residential with 3 barns/Steel Driveshed/Heated Garage.Land elevation is high and dry, Donegal loam w/winter wheat planted currently on half of the tillable land w/proper crop rotation practiced for generations.Barn foundation restored 2021/electrical upgrade 2022The elegant country manor home features generous living spaces ideal for Multiple family life or entertaining guests. Currently offering 2 primary bedrooms with ensuites in main house, 3 bedrooms w ensuite in South Wing plus separate apartment for extended family, staff, or guest stays.Energy efficient $1million renos done in 2012 adding geothermal, 440amp service, Generac and so much more.The property includes a swimming pool, tennis court, classic farm barns, and open fields suitable for hobby farming, equestrian use, or agricultural pursuits.Mountain Ash Farm has also proven ideal for hospitality and gatherings, with expansive lawns that provide a picturesque setting for celebrations and special events. Mature trees, scenic views, and quiet country roads create a peaceful retreat while remaining within convenient reach of Creemore, Collingwood, and the recreational amenities of the surrounding Escarpment region.Successful Agritourism AirBnB with Spa.Four Seasons near Bruce Trail, Private Ski Clubs, Golf, Cycling Trails only 15 minutes to Wasaga. This property offers a RARE opportunity to enjoy a private country estate, operate a boutique farm, or develop a unique hospitality venture in one of Ontario's most sought-after rural landscapes just over one hour drive to GTA. See www.mountainashfarm.comMore details
Location! Location! Welcome to 1319 Greeneagle Drive nestled in the sought after Gated community of Fairway Hills. Quiet cul-de-sac plus granted access to 11 acres of meticulously maintained grounds. Backing onto the 5th fairway offering breathtaking views as soon as you walk in. This spectacular family home has been extensively renovated with well over 300K spent by the current owners. Painted throughout in crisp designer white, smooth ceilings, over 170 pot lights, updated 200amp panel, new shingles, skylight + insulation, stone driveway and walkway, commercial grade extensive home automation system with security/smart locks, EV ready and smart closet designs. The lower level has been professionally finished with a rec room, 5th bedroom, full washroom, gym and a fantastic pantry/storage room. The primary suite has been transformed to create his and hers closets and a spa- like ensuite with heated floors, glass curb less shower and soaker tub. Entertainers backyard with large deck and heated in ground pool. Close to top rated schools, hiking in the 16 mile trail system, shopping and highway access. Move in and enjoy!More details
**Why wait for a new build when you can move in NOW & save the equivalent of the HST rebate? Seller is offering a $24K CREDIT on closing-no waiting, no risk,no delays. Preconstruction can't match this offer-3100 sq ft of beautifully finished space, $150K in Builder upgrades & a premium ravine lot with no rear neighbours-all for under $2M! Act now - same rebate, better home, ready NOW! ** For those seeking privacy, nature & a setting that's exceptional, this is a rare opportunity in Upper Joshua Creek. Offering the only ravine lot in the area under $2M, this home delivers exceptional value for buyers who prioritize space, serenity & a connection to green surroundings. Soaring 10' ceilings on the main level & 9' ceilings on the upper & lower levels enhance the home's bright, open feel. White oak engineered hardwood flows throughout, complemented by a vaulted great room ceiling, gas fireplace, triple-glazed windows & an abundance of natural light with serene ravine views. The modern white kitchen is stylish & functional, featuring quartz countertops, soft-close cabinetry with pot drawers & an oversized island with breakfast bar-perfect for everyday living & entertaining. The open-concept great room & dining area provide an inviting space to gather, while the practical mudroom with inside garage access adds everyday convenience. Upstairs, the primary suite offers a tranquil retreat with tray ceiling, walk-in closet & spa-inspired ensuite with freestanding soaker tub & glass-enclosed shower. Three additional bedrooms, two full bathrooms, a laundry room & an open loft overlooking the great room complete the upper level. The unfinished walkout basement boasts upgraded 9' ceilings, oversized sliding doors, bathroom rough-in & large storage-offering outstanding potential to customize your dream space. Located on a quiet crescent, close to parks, trails, shopping, dining, and major highways, this home blends luxury, privacy &lifestyle in one remarkable offering.More details
This completely move in ready family home is on one of the prettiest and most desirable streets in Glen Abbey. Pride of ownership is evident in this private enclave of Arthur Blakely homes. Situated in the middle of the crescent this house backs onto treed ravine and is very private in the backyard. The four plus one bedroom family home is perfect for a growing family. Renovated kitchen with greenhouse windows overlooks the backyard/ravine/hot-tub. Family room with wood burning fireplace also overlooks the backyard. Kitchen was fully renovated with custom cabinetry, large island, granite counter tops, stainless steel appliances and built-in window seat. Main floor laundry/mudroom has custom built in cupboards, access to garage and side yard and front loading washer and dryer. Maple hardwood throughout the main and second floors. Primary bedroom has extra large walk-in closet with window and large fully renovated bathroom with soaker tub and large shower. There are 3 other spacious bedrooms and main bathroom that was fully renovated in 2023 on the second floor. Fully finished basement has large recreation area, gym area, fifth bedroom, 3 piece bathroom and loads of storage. Quiet court has quick access to Abbey Lane Park and school as well as playground and toboggan hill in winter. Amazing location close to trails, highly rated schools, parks, shopping, transit, quick access to major highways, Oakville hospital, Glen Abbey Golf course and the famous Monastery Bakery.More details
Welcome to Glen Abbey Encore! A neighborhood that offers the best variety of amenities in Canada's best place to live. There's great shopping, top rated public, separate and private schools, popular restaurants, Rec Centers, Libraries & more all close at hand. Golfers will love the proximity to Deerfield Golf Club, Glen Abbey Golf Course and many others nearby. This stunning Modern 4 bedroom + 5 bathroom residence blends refined design with everyday functionality in a vibrant, family-friendly neighbourhood. Impressive 10 ft ceilings on the main floor and 9 ft ceilings on the second level and finished lower level. Enjoy cozy nights with a double sided fireplace in the Dining and Family room. Enjoy Chef inspired meals prepared in your Gourmet Kitchen with BI Cooktop and Oven. The Primary Bedroom features a large walk in closet and elegant spa ensuite with free standing tub. Spacious bedrooms one with ensuite and 2 sharing a Jack and Jill bathroom. The beautiful parks, beaches and marinas of Lake Ontario are just minutes south, & commuters will enjoy proximity to Bronte GO Station and Hwy 407 and the QEW/403. With all this and more right at your doorstep, this is one Encore that undoubtedly deserves a standing ovation.More details
A home built to last, nestled on a quiet, family-friendly street in prestigious Glen Abbey community.This impressive two-storey residence offers a timeless, functional layout with 5+2 bedrooms, 5 bathrooms, and over 5,000 sq ft of living space.Step inside and be welcomed by a spectacular Scarlet O'Hara staircase, complemented by double skylights that flood the home with natural light throughout the day. The bright living room features a picturesque window overlooking the front garden, while the formal dining room provides an elegant setting for entertaining.The kitchen showcases custom cabinetry, a central island, granite countertops, eating area, smooth ceilings, and pot lights, creating a perfect space for everyday living. The spacious family room, complete with a cozy wood fireplace, offers the ideal gathering place for family and friends. A main floor office adds flexibility for working from home space.Ascending the elegant wood staircase, the second floor features a spacious primary retreat with a reading nook, walk-in closet and 5-piece ensuite bathroom. Above the garage, an in-law suite with own private staircase offers exceptional private living space. Three additional generously sized bedrooms, each with large windows and ample closet space, share a well-appointed 4-piece bathroom.The finished lower level provides additional living space, featuring a large recreation room with enlarged windows, an extra two bedroom, a kitchen, and a full bathroom - ideal for extended family, guests, teenagers.Step outside to enjoy the private backyard retreat, complete with a wooden deck and patio stone area, perfect for outdoor entertaining and relaxing.Conveniently located near provincial parks, scenic trails, the new hospital, major highways including the QEW and 403, and award-winning golf courses, this exceptional home offers the perfect blend of space, comfort, and an unbeatable Glen Abbey lifestyle.More details
*OPEN HOUSE SUNDAY, MAY 31st, 2-4pm - 154 HOWELL ROAD, OAKVILLE* Boasting almost 4,600 sq ft of beautifully finished living space, this spectacular executive 5-bedroom, 5-bath family home is located in the highly sought-after River Oaks neighbourhood. Immaculate and completely turn-key, this exceptional residence showcases outstanding attention to detail throughout with extensive mouldings, designer lighting, rich hardwood flooring, and upscale finishes from top to bottom.The thoughtfully designed floor plan offers spacious principal rooms, a desirable main floor office, and an ideal family layout featuring 3 bathrooms on the second level, including a stunning brand new spa-inspired ensuite in the luxurious primary retreat.The heart of the home features elegant decor, beautiful stone countertops, and exceptional spaces for both everyday living and entertaining both inside and out. The deluxe fully finished basement is an entertainer's dream complete with a wet bar, gym area, games space, full bath, fireplace and a wine cellar. Step outside to your own private backyard oasis featuring a massive cedar deck, hot tub, privacy fencing with ambient lighting, and breathtaking landscaping front and back. Shed with electricity. Exceptional curb appeal begins with the flagstone entrance. Ideally situated within walking distance to top-rated schools, parks, trails, recreation centre, shopping, and more, this outstanding home truly offers all the "bells and whistles" for the discerning buyer. Seller can accommodate a 30 day closing! A rare opportunity in one ofOakville's most desirable family communities - you will not be disappointed.More details
*OPEN HOUSE SUNDAY, MAY 31st, 2-4pm - 2372 SAUGEEN ROAD, OAKVILLE* Large 5 bedroom family home on one of River Oaks premier streets! Boasting exceptional curb appeal and meticulously landscaped front and back gardens including a pool, this beautifully maintained residence offers over 3,100 sq ft of living space. The main floor features large principal rooms including a dedicated home office. large living and dining rooms, family room with gas fireplace and hardwood flooring. The updated kitchen is filled with natural light and showcases granite countertops, newer appliances, ample white cabinetry, and ideal space for everyday living and entertaining. The second level offers 5 generous bedrooms and 3 bathrooms, including an expansive primary with renovated ensuite featuring a jacuzzi tub, oversized glass shower with multiple body jets, and large walk-in-closet. Room for everyone! Step outside to your private backyard retreat complete with a fabulous inground pool and beautifully maintained landscaping - perfect for summer entertaining and family enjoyment. New pool liner (May 2026). Ideally located within walking distance to excellent schools, parks, Sixteen Mile Trails, shopping, and more. Homes rarely come up for sale on this street -don't miss the opportunity to own a timeless family home in an exceptional neighbourhood.More details
PRIME SOUTH OAKVILLE LAKESIDE LIVING. Nestled in an exclusive enclave of townhomes known as The Moorings, this elegant executive freehold end-unit offers refined multi-level living just steps from Lake Ontario. Boasting approximately 1,920 sq. ft. above grade, this beautifully appointed home features two spacious bedrooms, each with its own private ensuite complete with heated floors. The primary retreat impresses with a generous walk-through closet and a luxurious 5-piece ensuite, while the second bedroom offers a walk-in closet and 4-piece ensuite. Laundry located on the second level. The stunning living room showcases soaring 12'7" ceilings, a cozy gas fireplace, and picturesque views of Sixteen Mile Creek and the marina. Designed for both comfort and entertaining, the open-concept kitchen and family room feature a custom designer kitchen with granite countertops, stainless steel appliances, and a walk-out to a private deck. Step outside to your own serene retreat-this private deck backs onto lush greenery, creating a peaceful oasis alive with a variety of birds and local wildlife, offering a truly tranquil setting to relax, unwind, and enjoy nature. Additional highlights include hardwood flooring and crown moulding throughout the main level, a finished basement with a second gas fireplace, charming upper foyer storage, and a rare two-car garage with inside entry. Newer roof and windows. Enjoy an unparalleled lifestyle just moments from Tannery Park, the vibrant downtown core, boutique shopping, fine dining, the Oakville Public Library, and the Oakville Centre for the Performing Arts. Convenient access to the GO Station and major highways ensures effortless commuting. Seasonal lane clearing fee: (Nov-Mar) $229 (2025).More details
Beautifully maintained and thoughtfully designed, this 4-bedroom, 3-bathroom home offers an exceptional blend of comfort, functionality, and understated style on an exceptionally quiet, family-friendly street, just a safe 5-minute walk to Oodenawi Public School. With George Savage Park steps away, nearby trails, and everyday amenities close at hand, the location is ideal for young families seeking a connected, walkable neighbourhood. A welcoming covered front porch with classic columns and landscaped approach creates an immediate sense of arrival. Inside, the bright, well-proportioned main level offers seamless flow between the kitchen, breakfast area, dining space, and living room-ideal for everyday living and entertaining. A feature fireplace adds warmth and character, while large windows fill the home with natural light. The kitchen offers generous workspace and storage, centred around a large island that naturally becomes the hub of daily life. Upstairs, four spacious bedrooms provide flexibility for growing families, guests, or work-from-home needs. The primary suite features a walk-in closet and 5-piece ensuite, complemented by a full main bathroom, upper-level laundry, and a separate study nook perfect for homework or quiet workspace. Meticulously cared for throughout, the home reflects clear pride of ownership. The unfinished lower level offers over 1,100 sq. ft. of additional space with outstanding potential for future living, recreation, or fitness areas tailored to your needs. Outside, the private rear garden has been professionally landscaped with stone pathways, curated plantings, and ambient lighting, creating a peaceful retreat ideal for quiet evenings or entertaining. Ideally located near parks, schools, trails, and commuter routes, this is a rare opportunity to own a home that combines quality, comfort, and versatility in one of Oakville's most desirable family communities.More details
Listed by RE/MAX ABOUTOWNE REALTY CORP. and RE/MAX Aboutowne Realty Corp., Brokerage
Data was last updated May 30, 2026 at 02:15 AM (UTC)
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