Welcome to 1399 Willowdown Road, an exceptional custom residence inspired by Frank Lloyd Wright's iconic Prairie designs, nestled on a spectacular ravine lot with a picturesque creek in prestigious South Oakville. Offering over 6,800 sq. ft. of beautifully finished living space, this remarkable home features 5 bedrooms upstairs plus 2 additional bedrooms in the finished lower level. The main floor impresses with soaring 10' ceilings, wide-plank oak flooring, custom millwork and an open-concept layout. At its heart is a chef-inspired kitchen with an oversized island, quartz counters, JennAir Professional Series appliances, extensive cabinetry and a butler pantry, opening to the expansive great room and breakfast area. Enjoy seamless indoor-outdoor living from the covered lanai with a fireplace and skylights overlooking the ravine. The finished lower level is designed for entertaining, featuring a dedicated home theatre, billiards and recreation areas, exercise room, 2 bedrooms and a full bathroom. Additional highlights include Lutron lighting automation, remote-controlled blinds, built-in ceiling speakers, multi-camera security, illuminated stair treads, 9' upper-level ceilings and a double garage. Just steps from Coronation Park and Lake Ontario, and minutes to top schools, shopping, dining and GO Transit. A truly rare offering combining architectural distinction, exceptional space and ravine-side privacy.More details
Welcome to this exceptional 3+1 bedroom brick bungalow in the heart of West Oakville, nestled on a quiet, tree-lined street surrounded by mature trees and multi-million-dollar custom homes. Just minutes from Bronte Harbour, Lake Ontario, Appleby College, top-ranked schools, waterfront parks, and marinas, this property offers comfortable single-level living, remarkable outdoor space, and outstanding long-term potential. Situated on an impressive 75 x 272 ft lot-approximately 20,505 sq. ft .- the home features a rarely offered backyard complete with an inground pool, spacious deck, and fully fenced yard, perfect for relaxing and entertaining. The carpet-free main level includes a hardwood living room with a gas fireplace, a granite kitchen illuminated by a skylight, and dining and family rooms with walkouts to the deck. The main-floor primary bedroom features a walk-in closet and 4-piece ensuite, making it ideal for anyone seeking convenient single-level living. Two additional bedrooms and a 2-piece bathroom complete the main floor. The finished lower level provides a fourth bedroom, spacious recreation room, 3-piece bathroom, and separate laundry-ideal for guests or extended family. Additional highlights include an attached garage, parking for five vehicles, forced-air gas heating, and central air conditioning. The property also comes with an approved building permit for a custom luxury residence, allowing the purchaser to save considerable time and cost. With RL2 SP:1 zoning, an approved permit, and convenient access to the QEW, Highway 403, and GO Transit, this rare West Oakville property presents an exceptional opportunity to move in, invest, or build your dream home. Book your private showing today!More details
This exceptional, beautifully redesigned bungalow is located on sought-after Pinegrove Road in one of Oakville's most desirable neighbourhoods. Created with quality, comfort and modern living in mind, this impressive home offers 3 spacious bedrooms and 3.5 bathrooms. The bright, open-concept layout features flush beams, smooth ceilings and no bulkheads, giving the home a clean and airy feel. The elegant custom Italian kitchen is a true highlight, featuring premium Miele and Liebherr appliances, VELUX power-opening skylights with built-in shades and quality TOTO fixtures. Stylish herringbone tile flooring and a Napoleon gas fireplace bring warmth and character to the living space. Extensive improvements include a ManaBloc plumbing system, replaced drains to the city side, upgraded 1.25" copper water line, new electrical with 150+ LED pot lights, soundproofed walls and ceilings, new roof, eavestroughs, furnace, A/C and tankless hot water system. A concrete rear addition provides valuable extra living space, while fresh stone and stucco finishes on the home and garage create impressive curb appeal. The fully insulated and finished shed offers flexible space for a home office, gym, studio or private retreat. Step outside to your own resort-inspired backyard, with over $250,000 invested in outdoor improvements. Highlights include natural stone landscaping, a Crown Verity outdoor kitchen with quartz counters, built-in Bose audio and an 8' privacy fence. The expansive U-shaped in-and-out driveway provides parking for 20+ vehicles. A rare Oakville home combining thoughtful design, impressive upgrades, privacy and exceptional indoor-outdoor living.More details
Straight from the pages of a design magazine, this beautifully renovated, on-trend home offers more than 4,500 sq. ft. of thoughtfully designed living space. Tucked away on a quiet cul-de-sac in prestigious Southwest Oakville, it's just steps from Appleby College and the shores of Lake Ontario. The property is professionally landscaped by award-winning Gildermans, creating a stunning setting that perfectly complements this exceptional home.Designed for both everyday living and effortless entertaining, the main floor features a spacious formal dining room and a warm, inviting family room with a wood-burning fireplace. The stunning chef's kitchen is a true showpiece, featuring a Wolf induction cooktop, two double wall ovens, Sub-Zero refrigerator, two Miele dishwashers, two Marvel wine and beverage refrigerators, quartz countertops, and an impressive 9-foot island. The kitchen flows seamlessly into the family room, creating the perfect setting for gathering with family and friends.Upstairs, the luxurious primary suite serves as a private retreat, complete with a spa-inspired five-piece ensuite, walk-in closet, and an expansive terrace-ideal for enjoying your morning coffee or unwinding in the evening sun. This level also includes a generously sized second bedroom with its own ensuite, two additional bedrooms, a home office, a full bathroom, and a brand-new full laundry room for ultimate convenience.The finished lower level offers exceptional additional living space with a large recreation room, a second laundry room featuring a Miele washer and dryer, and a three-piece bathroom.Step outside to your own private backyard oasis, where a sparkling saltwater pool and beautifully landscaped gardens create the perfect escape. This exceptional home combines luxury, comfort, thoughtful design, and an unbeatable location-an opportunity not to be missed.More details
Listed by RE/MAX Escarpment Realty Inc., Brokerage
Welcome to one of South Oakville's most coveted addresses.Maplehurst Ave is renowned for its quiet, luxury setting-something every buyer already knows and values.This rare north-east facing corner property offers excellent exposure, allowing for abundant natural light throughout the day.The existing home is well-maintained and fully livable, perfect to move in for your family.Currently generating rental income of $3200 per month.The mature trees at the rear provide exceptional privacy from the street, while the clean, open lot is perfectly suited for a future pool and outdoor oasis.The property comes with approved plans for a stunning 6,800 sq.ft. classical residence (approx. 4,300 sq.ft. above ground + 2,500 sq.ft. bsmt), with over $80,000 already invested in permits and architectural approvals-saving you significant time and cost (Tree Removal Permits included).The project is just steps away from utility disconnection and final building permit issuance, allowing you to fast-track construction with ease. Surrounded by multi-million dollar estates, this is a rare, turnkey opportunity for builders, investors, or end-users to secure a premium lot and create a truly exceptional home.More details
Welcome to 1128 Pinegrove Road, a rare, turn-key gem in an incredibly valuable neighbourhood! Skip the stress of renovations with an entirely brand-new, custom interior that blends modern luxury with classic charm. The heart of the home is a stunning custom kitchen featuring sleek cabinetry and new appliances, flowing into a bright, open layout perfect for family life. You'll find large, sun-filled bedrooms that offer plenty of personal space, along with a massive 4th bedroom in the above-grade lower level. This level also features a cozy recreation room with a beautiful brick fireplace, adding to the home's warm character. All new exterior finishes, windows, doors, brand new bright stucco for great curb appeal and a new charming interlocked backyard for summer hosting, this house is ready for you to just move in and enjoy. Perfectly located near the lake, highly rated schools, highways including the QEW, shopping and public transit. Custom quality in a prime location at a price that makes sense!More details
One-of-a-kind opportunity to acquire a professionally built-out office condominium in a premier Oakville location on North Service Road, ideally situated between Third Line and Fourth Line. This move-in-ready 6,129 sq. ft. office offers a highly functional layout featuring a combination of private offices, boardrooms, collaborative open work areas, and impressive 18-foot main clear height with 9-foot office clear height. Currently zoned for Medical use. Designed with premium finishes throughout, the property includes a commercial-grade kitchen (restaurant-grade appliances available), a built-in ceiling mount Bose audio system in open space and 4K ceiling mount projector. Professionally installed security and alarm system. Occupants also enjoy access to a beautifully landscaped common greenspace and a quiet courtyard, providing an exceptional work environment. Ample parking for clients and staff. Ideally located with immediate access to the QEW, Highway 403, public transit, and a wide range of nearby amenities.More details
One-of-a-kind opportunity to acquire a professionally built-out office condominium in a premier Oakville location on North Service Road, ideally situated between Third Line and Fourth Line. This move-in-ready 6,129 sq. ft. office offers a highly functional layout featuring a combination of private offices, boardrooms, collaborative open work areas, and impressive 18-foot main clear height with 9-foot office clear height. Currently zoned for Medical use. Designed with premium finishes throughout, the property includes a commercial-grade kitchen (restaurant-grade appliances available), a built-in ceiling mount Bose audio system in open space and 4K ceiling mount projector. Professionally installed security and alarm system. Occupants also enjoy access to a beautifully landscaped common greenspace and a quiet courtyard, providing an exceptional work environment. Ample parking for clients and staff. Ideally located with immediate access to the QEW, Highway 403, public transit, and a wide range of nearby amenities.More details
Excellent opportunity to own a well-established dry cleaning business in a prime location with many years of successful operation and a loyal, long-standing customer base.This business offers stable cash flow and consistent repeat clientele, making it an ideal opportunity for buyers looking for an established, income-producing business with strong community presence.Located in a high-traffic, highly desirable area with excellent exposure and surrounding residential growth, this is a rare turnkey opportunity with significant long-term potential.Perfect for owner-operators, family businesses, or investors seeking a reliable business with steady income and an established reputation.More details
Welcome to this exceptional upscale residence set on a sprawling 75 x 150 ft lot in prestigious Coronation Park. A 10-minute walk to Coronation Park on Lake Ontario and minutes to Bronte Harbour and Village, Oakville Harbour and downtown Oakville, for upscale shopping and restaurants. A 5-minute drive to the QEW and Bronte GO Station for commuters. Showcasing outstanding curb appeal with a stucco and stone façade, deluxe mouldings, professional landscaping, a stone walkway, covered flagstone porch and an extra-long driveway to a triple (tandem) garage, the home transitions seamlessly to a private backyard oasis-an entertainer's dream with upgraded stone patios, a custom saltwater pool with armour stone waterfall, lush gardens, multiple seating areas and ultimate privacy with mature trees. Offering 4 spacious bedrooms, 3.5 bathrooms and a professionally finished walk-up basement, the interior exudes refined craftsmanship with exotic hardwood floors, smooth ceilings, rounded drywall corners, crown mouldings, custom cabinetry, an impressive floating staircase, and abundant natural light. Highlights include a grand dining room, a dramatic family room with a cathedral ceiling, a gas fireplace and walkout, a private office, and a chef's kitchen with custom cabinetry, granite counters, an oversized island and premium Viking appliances. Upstairs features four generous bedrooms and two lavish bathrooms, including the primary retreat with a spa-inspired ensuite offering a jetted tub and a glass shower. The walk-up basement impresses with a large recreation room, a games room with a fireplace, a media lounge, and a 3-piece bath-perfect for family living and entertaining.More details
Welcome To Your Signature Address in Prestigious South Oakville. An exceptional opportunity to own a charming residence on a rare premium 75 x 150 ft lot, nestled in one of South West Oakville's most sought-after enclaves, surrounded by luxury custom homes. Ideally located within walking distance to the lake and top-ranked schools, this home offers the perfect blend of lifestyle, location, and future potentials.More details
Set on a premium 60-foot lot in one of Oakville's most coveted pockets, this extraordinary custom residence offers over 5,800 square feet of meticulously crafted living space that redefines modern luxury through uncompromising engineering and timeless European-inspired design. Built with insulated concrete forms (ICF) extending through the second floor, the home features high-performance European windows, extensive microcement finishes, radiant heated floors throughout-including the basement and garage-and a striking architectural cantilever staircase. Highlights include a stunning main kitchen with a separate butler's pantry, an exceptional lower-level entertainment zone complete with a custom microcement bar, walk-in wine display, and private home theatre, plus a car-enthusiast garage and a backyard featuring an approved pool permit. With an estimated completion of October 2026, the purchaser still has a rare opportunity to select and customize final finishes. A masterclass in contemporary craftsmanship, delivering an unmatched standard of refined, energy-efficient living.More details
Data was last updated August 19, 2026 at 04:15 AM (UTC)
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website.
The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.