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$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
$8,999,999
W13237504 MLS
Rare opportunity to own a building right on Trafalgar in Downtown Oakville. Already passed approval to build up to 6 stories! Amazing future development site ready to go! New leases in place on some units at proper market rents. When fully leased over a 6% cap rate.

115 Trafalgar Road, Oakville
$7,249,000
5 Beds ⋅ 5 Baths ⋅ W13625250 MLS
This exceptional residence has been extensively upgraded with curated enhancements that seamlessly blend timeless architecture with modern luxury, advanced technology and exceptional craftsmanship. Designed for effortless indoor-outdoor living, the enclosed lanai features floor-to-ceiling glass sliding doors on three sides with automated electronic screens for year-round comfort and privacy. The professionally landscaped grounds include a custom 13' x 9' powered garden pavilion, natural stone entertaining terrace, 1,100 sq. ft. wraparound composite deck, approximately 500 sq. ft. of Ipe hardwood privacy screening, luxury hot tub, heated saltwater pool with waterfall, 20-foot motorized retractable awning and a fully automated seven-zone irrigation system and hot tub. The gourmet kitchen has been refreshed w/ custom cabinetry doors and drawer fronts while maintaining its timeless design. Premium appliances include two built-in dishwashers, two wall ovens, integrated refrigerator and freezer, built-in microwave, approximately 100-bottle wine refrigerator and two oversized island prep sinks with garburators. The principal fireplace has been restored with a custom surround, creating a stunning focal point. The luxurious primary suite features restored wood paneling, a custom dressing room, spa-inspired ensuite with freestanding tub, steam shower, heated floors and heated towel warmers. A DuraDek waterproof roof system (2023) was installed over the private terrace. All upper bedroom ensuites also feature radiant heated floors and heated towel warmers. An upgraded Crestron Smart Home system controls lighting, climate, motorized blinds, distributed audio and home automation. The home is equipped with three owned high-efficiency furnaces, three air con. systems, two steam humid., two-zone climate control. Every detail has been thoughtfully curated to deliver timeless elegance & intelligent technology. Approximately 7000 Sq. ft. of Livingspace. Luxury Certified.

54 RAYMAR Place, 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
$5,999,900
3 Beds ⋅ 4 Baths ⋅ W13453644 MLS ⋅ The Randall Residences BLDG.
RESTORATION HARDWARE SHOW SUITE: Welcome to the crown jewel of The Randall Residences, Oakville's most prestigious address. This sun-filled Signature Penthouse Suite is the largest residence inside and out, offering approximately 3,337 sq. ft. of sophisticated living plus a 386 sq. ft. second-storey lounge with skylight and an expansive 1,327 sq. ft. southeast-facing terrace. Enter through a grand rotunda foyer with marble floors and an impressive RH chandelier, setting the tone for this exceptional home. The open-concept living and dining areas boast 12-foot ceilings, floor-to-ceiling wrap-around windows, custom Downsview cabinetry, top-of-the-line appliances, and a gas fireplace - an entertainer's dream. Restoration Hardware fixtures illuminate throughout the suite exuding an atmosphere of sophisticated refinement. The principal bedroom retreat is a haven of tranquility with a custom zebra-wood dressing room and a spa-inspired 6-piece ensuite, complete with heated marble floors, polished nickel fixtures, and a freestanding soaking tub. Two additional bedrooms each feature their own private ensuites for ultimate comfort and privacy. Ascend to the second-storey lounge, ideal for a home gym, office, or serene retreat, and step out to your private rooftop terrace designed for entertaining, featuring multiple lounging and dining zones with a gas BBQ hookup. Additional luxuries include a Crestron home automation system, integrated entertainment features, 3 parking spaces, and 2 storage lockers. Residents enjoy 24-hour concierge service in this award-winning Rosehaven Homes development, celebrated for its impeccable craftsmanship and timeless elegance. Sotto Sotto on the ground floor. Located steps from Lake Ontario, fine dining, boutique shopping, and just minutes to major highways, this penthouse represents the pinnacle of luxury living in Oakville. If you demand the best, look no further. Luxury Certified. Listed US$4,255,000

300 Randall Street Unit PH1, 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
$4,750,000
6 Beds ⋅ 8 Baths ⋅ W13023762 MLS
Welcome to 417 Union Street, an exceptional modern home nestled in the heart of prestigious Old Oakville. Completed in 2023, this one-of-a-kind residence blends modern farmhouse inspiration with refined contemporary and traditional design elements, creating a home that is both striking and timeless. The modern farmhouse exterior showcases clean lines, black-framed windows, and a harmonious mix of materials, complemented by a covered porch, professionally landscaped front and back yards, and a stone six-car driveway. The backyard offers a private retreat with a deck, stone patio, and custom garden shed. Inside, the home is filled with natural light and defined by a modern, sleek interior. Wide-plank engineered hardwood flooring, custom ceilings with integrated LED lighting, and large-format matte tiles elevate the main living areas. The chef-inspired kitchen features quartz countertops and backsplash, an oversized centre island, built-in Bosch appliances, and a convenient adjoining servery. A tiered maple staircase with glass railings leads to the upper level, where skylights continue the home's bright and airy feel. The expansive primary suite spans over 700 square feet and offers two walk-in closets and a luxurious five-piece ensuite with double vanity, freestanding tub, and glass-enclosed rainfall shower. Three additional bedrooms each include their own custom three-piece ensuite with modern walk-in showers. The fully finished lower level adds outstanding versatility with a second kitchen, large recreation room, two additional bedrooms with ensuites, and a powder room. Additional highlights include an elevator servicing all three levels, 10-ft ceilings on the main and lower levels, pot lights, blackout blinds, built-in speakers, and a security system. Ideally located minutes from Lake Ontario, parks, trails, Oakville GO, the QEW, and top-ranked schools including Appleby College, this home delivers modern luxury, thoughtful design, and an exceptional lifestyle.

417 Union Street, Oakville
$4,290,000
4 Beds ⋅ 4 Baths ⋅ W12899014 MLS
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.

Lot 101 Douglas 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
$3,980,000
4 Beds ⋅ 4 Baths ⋅ W13109474 MLS
Set on a beautiful 100' x 136' lot in Prestigious Olde Oakville, this exceptional family home offers 4,752 sq ft of total living space of refined timeless design & impeccable craftsmanship all just a short stroll to Downtown Oakville, the lake, and some of Oakville's most sought-after schools. classic brick exterior, solid wood front door, and towering mature trees create a warm and elegant first impression. This home exudes an inviting aesthetic that feels made for family living and effortless entertaining.The kitchen features top-of-the-line appliances, two Miele dishwashers, dual walk-in pantries, water filtration system, three sinks including a coffee station/wet bar, and an oversized island that comfortably gathers family and friends for everything from casual breakfasts to holiday celebrations. The adjoining dining room is anchored by a charming wood-burning fireplace, while the spacious family room, also with a wood-burning fireplace, opens seamlessly to the private backyard, creating an ideal indoor-outdoor connection. Enjoy sunny south exposure, a sparkling saltwater swimming pool(liner/pump/heater 2024), Maibec deck with sleek glass railings, and a beautiful stone patio ideal for summer dining and lounging. Despite the impressive outdoor amenities, there remains abundant green space for children to play and the whole family to gather. The functional mudroom and sophisticated main floor den complete the thoughtfully designed main level. The second floor is equally impressive, highlighted by a luxurious primary retreat with its own gas fireplace, walk-in closet, custom built-in storage, and five-piece ensuite with heated flooring. Three additional generously sized bedrooms and a beautifully appointed full bathroom provide ample space for a growing family. Finished to the highest standards, this extraordinary residence offers the rare combination of timeless style, family-focused functionality, and an unbeatable Olde Oakville location. Welcome Home.

528 Michael Terrace, Oakville
$3,950,000
4 Beds ⋅ 4 Baths ⋅ W12991350 MLS
Private, elevated, and unlike anything else in Old Oakville - A true four-season outdoor retreat, your private playground for the outdoor enthusiast-where each day invites skating, paddling, kayaking, hiking, fishing, boating and cross-country skiing, alongside wildlife watching and refined al fresco dining, embracing nature in all its seasons. This lofted waterfront residence commands breathtaking views and unmatched privacy along the 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. .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.

382 Trafalgar Road, Oakville
$3,949,000
4 Beds ⋅ 5 Baths ⋅ W13610074 MLS
This completely renovated contemporary residence represents the pinnacle of modern design and sophisticated living in one of Oakville's most desirable locations of Old Oakville.Every detail of this 4 Bedroom | 4+1 Bathrooms | 4,819 Sq Ft Finished Living Space has been meticulously reimagined to deliver an unparalleled standard of quality and craftsmanship.The highly functional main floor plan centers around an exceptionally sleek kitchen open to the Great Room with gas fireplace and walk out to the resort style backyard and pool.The kitchen is outfitted with luxury high-end appliances, an oversized island seating eight, and an additional peninsula for casual entertaining in the bar area.Adjacent to the kitchen, is a walk in pantry with an additional dishwasher and fridge. Not to be missed is the impressive temperature-controlled wine room accommodates approx 1,000 bottles-a striking feature for the discerning entertainer.A versatile family room/main floor bedroom with ensuite which can be used as a principal bedroom or guest suite, laundry room, walk-in main closet for storage and access to oversized double car garage.The 2nd level principal suite is a private sanctuary featuring juliette balcony, gas fireplace, two walk-in closets and a spa-inspired ensuite with heated floors, walk-in shower, and a standalone soaking tub.Two additional spacious bedrooms each with their own ensuites complete the level. Not to be missed is the finished lower level room with added storage in the pantry and crawl space area. The backyard is an entertainer's paradise, showcasing a saltwater pool, two expansive patio areas, two gazebos with a gas fire table, and premium Dutch-imported artificial turf that remains lush year-round with zero maintenance.Ideally situated steps from Whole Foods Market, Oakville GO Train, for seamless transit connectivity,and the Oakville Trafalgar Community Centre this extraordinary property offers both refined luxury and everyday convenience.LUXURY CERTIFIED

287 MacDonald Road, Oakville
$3,790,000
4 Beds ⋅ 4 Baths ⋅ W12899458 MLS
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. A selection of 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. Impressive detached w/47-foot frontage, 2836 sqft of finished space w/an additional 1,000+ sqft(approx) in the lower level left untouched. Curated:4 beds + 3.5 baths. Utility wing from garage, chef's kitchen w/w/in pantry, expansive breakfast+great room. 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.

338 MACDONALD Road, Oakville
$3,600,000
W12773688 MLS
Prime Downtown Oakville location, this turnkey mixed-use building features two prime commercial units and four residential suites on second floor. This property sits on one of the most coveted blocks in downtown Oakville right on Lakeshore between Navy and Thomas. This offering provides a stable income stream and significant potential for future appreciation and redevelopment. Well-maintained with recent renovations including commercial spaces, windows, roof and appliances.

150 Lakeshore Road E, Oakville
$3,598,000
W13476786 MLS
An exceptional development opportunity in the heart of Downtown Oakville. Situated within the coveted CBD zoning district, this prime approximately 47.16 x 104.4 ft parcel offers outstanding potential for investors, developers, and end users seeking to capitalize on one of Oakville's most prestigious and walkable neighbourhoods. CBD zoning permits a wide range of residential, commercial, and mixed-use possibilities, including apartment, semi-detached, townhouse, and live-work dwellings, as well as business offices, retail stores, restaurants, hotels, medical offices, service commercial uses, and more. Surrounded by luxury residences, boutique commercial spaces, and established mixed-use developments, the property is just steps from the Oakville Marina, Lake Ontario, acclaimed restaurants, cafés, boutique shopping, and the vibrant downtown core. This highly desirable location offers a unique blend of waterfront living, urban convenience, and timeless charm. Extensive due diligence has already been completed, including previous site plan approval and a building permit for a proposed 4-storey condominium development. A rare opportunity to secure a premier Downtown Oakville parcel with exceptional long-term development potential in one of the GTA's most sought-after luxury markets.

132 Dunn Street, Oakville
$3,250,000
4 Beds ⋅ 3 Baths ⋅ W12419345 MLS
Nestled south of Lakeshore in the heart of Old Oakvilles historic district, this beautifully restored Georgian-style home, designed by Gren Weis, blends timeless character with modern updates. Steps from the lake, river, and vibrant Downtown, it offers an unmatched lifestyle location.The home boasts exceptional curb appeal with a flagstone path leading to a spacious foyer. Sun-filled interiors feature Farrow & Ball paint, new hardwood on the main level, preserved fir upstairs, smooth ceilings, and recessed LED lighting.The updated kitchen includes a large island, built-in appliances, and desk area. The dining room offers panelled walls, RH sconces, French doors to the garden, and plantation shutters. A charming living room features built-in bookcases, window seat, wood-burning fireplace, and walkouts to a sunroom overlooking the southwest garden and pool. A mudroom and stylish powder room complete the main floor.Upstairs are four bedrooms with ample closets and antique brass hardware. The primary suite offers custom built-ins and a renovated ensuite with heated Carrara marble floors and zero-threshold shower.The fully finished lower level (8 ceilings, slate flooring) adds living space with a media room, workout room, cedar closet, laundry, and storage. Updated mechanicals include a high-efficiency furnace, central AC, 100 AMP panel, irrigation. Cedar roof, new fencing, cobblestone driveway. Outside enjoy a private oasis with saltwater inground pool, brick patios, and landscaped gardens. Steps to the Lake, Oakville Club, Yacht Squadron, Library, Performing Arts Centre, Downtown, and top schools.

53 Thomas Street, Oakville
$3,250,000
5 Beds ⋅ 3 Baths ⋅ W10403987 MLS
Well positioned property in historic Old Oakville, south of Lakeshore, just steps to the beach, Oakville harbour and Town Square. Sitting proudly up on a rise, this 2 1/2 storey home features wonderful views, light and plenty of space to create your dream home. With lot dimensions of 105' x 105' this full-sized 11,044 SF lot is exactly twice the size of adjacent properties. Savvy buyers may investigate opportunities to sever the lot or explore the creation of an accessory dwelling unit on the property. Zoning RL3, Special Provision 11. The existing home sits entirely on one half of the property in the northeast corner leaving the south and the west portions of the lot open to potential. The existing residence features high ceilings, a grand staircase, formal living room with wood burning fireplace and adjacent sunroom. Lovely southeast dining room takes in all the sunlight. The kitchen and back entrance are in the southwest corner of the main floor. The second floor features 4 bedrooms and one main bathroom. The third floor with two large rooms used as the Primary suite features wonderful views over the garden, the lake, church tower and the beautiful trees of Old Oakville.

200 WILLIAM Street, Oakville
$3,199,000
2 Beds ⋅ 2 Baths ⋅ W13158074 MLS ⋅ The Randall Residences BLDG.
Welcome to one of Downtown Oakville's most celebrated residential addresses, imagined and brought to life by an exceptional local team, the internationally acclaimed luxury designer whose signature detailing elevates this landmark building into a work of art. Together, they crafted a boutique residence that seamlessly blends sophistication, exclusivity, and enduring elegance. This expansive suite features grand principal rooms, soaring ceiling heights, and refined architectural proportions throughout. The Great Room and adjoining Kitchen/Dining Room provide an impressive setting for both relaxed living and elegant entertaining, while the formal Foyer and circular entry gallery create a memorable sense of arrival. The private primary wing offers a gracious Master Bedroom with Juliet balcony, ensuite bathroom, with walk through dressing room, delivering a true luxury retreat. A second bedroom is perfect for guests or extended family and is thoughtfully preceded by its own private vestibule, enhancing comfort and privacy. Additional conveniences include a separate Laundry Room, dedicated Storage Room, and a Powder Room that complements the home's generous flow. The building also features the renowned Sotto Sotto restaurant on the main level - a testament to the calibre of the address and a unique lifestyle benefit for residents. Steps to the lake, marina, shops, cafés, and cultural venues, this residence offers a rare blend of boutique luxury and walkable urban convenience. A distinguished opportunity to live in one of Oakville's landmark buildings.

300 Randall Street Unit 211, Oakville
$3,195,000
3 Beds ⋅ 5 Baths ⋅ W12899190 MLS
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. A selection of distinct models, each magnificently crafted, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and contemporary gathering spaces. A true exhibit of flawless design and impeccable taste. The Arlington; 3,677 sqft of finished space, 3 beds, 3 full baths + 2 half baths, this model includes 622 FIN sqft in the LL. A few optional layouts ground + upper. Garage w/interior access to mudroom, ground floor laundry, walk-in closet, full bath + family room w/French door to rear yard. A private elevator services all levels. Quality finishes are evident; with 10 ceilings on the main, 9 on the ground & upper levels. Large glazing throughout, glass sliders to both rear terraces & front terrace. Quality millwork & flooring choices. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Chefs kitchen w/top appliances, dedicated breakfast, overlooking great room. Primary retreat impresses with large dressing, private terrace & spa bath. No detail or comfort will be overlooked, with high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Expansive outdoor spaces; three terraces & a full rear yard. Perfectly positioned within a canopy of century old trees, a stones throw to the state-of-the-art Oakville Trafalgar Community Centre and a short walk to Oakvilles downtown core, harbour and lakeside parks. This is a landmark exclusive development in one of Canadas most exclusive communities. Only a handful of townhomes left. Full Tarion warranty. Occupation estimated summer 2026.

321 Helen Lawson Lane, Oakville
$3,098,000
2 Beds ⋅ 3 Baths ⋅ W13439412 MLS ⋅ The Coventry BLDG.
Welcome to The Coventry Penthouse-one of downtown Oakville's most distinguished luxury residences. This architecturally significant suite, designed by acclaimed architect Bill Hicks, offers an unparalleled lifestyle just steps from the lake, waterfront parks, shopping, and dining. Occupying a premier position within this exclusive boutique building, with only two residences sharing the elevator, the penthouse delivers exceptional privacy and sophistication. Expansive living spaces are highlighted by soaring ceilings, a dramatic skylight, custom Downsview kitchen, walk-in pantry, formal dining room, integrated Sonos sound system, and elegant indoor-outdoor living. Two sets of French doors open to a covered terrace featuring a striking two-sided fireplace, while a spectacular private rooftop terrace creates the perfect setting for entertaining and relaxation. The luxurious primary retreat includes terrace access, a spacious walk-in closet, and spa-inspired five-piece ensuite. Complete with a second bedroom, den, 2.5 bathrooms, two premium parking spaces, and a locker, this exceptional residence offers the comfort of a custom home with the ease and convenience of luxury condominium living. A rare opportunity to own a truly unique penthouse in the heart of downtown Oakville. *Some photos may be virtually staged

253 Church Street Unit 402, 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
$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
$2,749,000
3 Beds ⋅ 4 Baths ⋅ W13599912 MLS
Welcome to sophisticated downtown Oakville living. This beautifully renovated luxury townhome offers over 2700sq.ft. of total living space, an exceptional combination of elegant design, generous spaces, and an unbeatable walkable location. Thoughtfully updated throughout with quality finishes and timeless style, this turnkey residence is ideal for discerning buyers seeking a refined, low-maintenance lifestyle in one of Oakville's most coveted neighbourhoods. The bright and spacious main living area is designed for comfort and effortless entertaining. Expansive living and dining areas are filled with natural light and flow seamlessly into a stunning renovated kitchen featuring premium appliances, extensive custom cabinetry, an oversized centre island, abundant storage, and a functional layout that will impress the most avid home chef. Step directly from the kitchen onto a large private deck, creating the perfect extension of your living space for outdoor entertaining, or simply enjoying a quiet morning coffee. Offering 2+1 bedrooms and 3+1 bathrooms, this home provides remarkable flexibility for families, professionals, and downsizers alike. The spacious primary retreat offers comfort andprivacy, while additional bedrooms accommodate family and guests with ease. A dedicated main floor office creates the ideal work from home environment, providing separation from the main living spaces without sacrificing convenience. The walk-up from the lower level presents endless possibilities and is perfectly suited for a nanny suite, in-law accommodation, guest quarters, home gym, or additional living space. With its own direct access, this level adds tremendous versatility to an already exceptional floorplan. Outdoor living is further enhanced by two private decks, offering multiple spaces to relax and entertain. A rare attached double car garage, combined with parking for an additional vehicle in the back drive, provides convenience seldom found in downtown locations.

146 Reynolds Street, Oakville
$2,700,000
W13619860 MLS
Exceptional opportunity to own in the heart of downtown Oakville on the coveted north (sunny) side of Lakeshore Road, steps from Town Square. This building offers flexible configuration for a user, investor, or owner-operator, with vacant possession providing full control over tenancy or immediate occupancy. A full, partially finished basement adds valuable storage or amenity space. CBD Sp9 zoning permits a broad range of uses. Future redevelopment potential. Frontage of 24 ft on one of Oakville's most trafficked pedestrian and vehicular corridors, surrounded by premier retailers and restaurants.

175-177 Lakeshore Road, Oakville
$2,599,000
2 Beds ⋅ 2 Baths ⋅ W13622526 MLS
Welcome to The Randall Residences at 300 Randall Street, the pinnacle of boutique luxury living in the heart of downtown Oakville. Developed by the award-winning Rosehaven Homes and masterfully designed by renowned luxury designer Ferris Rafauli, this exceptional 1-bedroom + den, 2-bathroom residence offers 1,807 sq. ft. of impeccably crafted interior living space, complemented by a 206 sq. ft. private terrace and a Juliet balcony off the primary suite. Timeless elegance is showcased throughout with rich hardwood flooring, exquisite custom ceiling details, designer lighting, custom millwork, and oversized windows that flood the home with natural light. The chef-inspired kitchen is a showpiece featuring premium Wolf appliances, marble countertops with a full-height marble backsplash, custom cabinetry, a generous centre island, and built-in appliances-perfect for both everyday living and entertaining. The expansive open-concept living and dining areas seamlessly connect to the oversized terrace, creating exceptional indoor-outdoor living. Retreat to the luxurious primary suite featuring a walk-in closet, Juliet balcony, and a spa-inspired ensuite finished with floor-to-ceiling marble, a glass-enclosed shower, heated floors, and premium fixtures. The spacious den offers the perfect setting for a home office, library, or guest space, while the second full bathroom provides added convenience. Residents enjoy world-class amenities and exceptional concierge, all just steps from Oakville's finest boutiques, acclaimed restaurants, cafés, the waterfront, parks, and marina. A rare opportunity to own one of Oakville's most distinguished luxury residences.

300 Randall Street Unit 304, 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
$2,299,000
4 Beds ⋅ 3 Baths ⋅ W13632844 MLS
Absolutely stunning and totally upgraded four bedroom family home in prime South East Oakville location! Very desirable street on a quiet cul-de-sac close to top public and private schools. The spacious primary suite is privately set on the upper level and features soaring ceilings, a beautiful ensuite, and a walk-in closet. The skylight gives the bedrooms lots of natural light, enhancing the warmth and openness of the home. The chefs kitchen includes an oversized island and seamlessly flows into the open concept living space with a walk out to the deck that is perfect for entertaining! This turn key home features modern finishes throughout, including a cozy fireplace in the family room. The fully fenced backyard offers a private oasis. Smart home features include, an Ecobee thermostat, Ring camera, and built in Sonos surround sound. Outdoor upgrades include, a gas BBQ hookup, and a full irrigation system. Close to all amenities such as public transit, parks, Downtown Oakville, shops, restaurants, and highways. Don't miss the opportunity!

467 Caesar Avenue, Oakville
$2,099,000
5 Beds ⋅ 2 Baths ⋅ W13637112 MLS
**An exceptional opportunity to secure one of Old Oakville's most desirable building lots.** Situated on prestigious Douglas Avenue, this rare **48' x 150'** property offers the perfect canvas to create a custom luxury residence in one of Oakville's most sought-after neighbourhoods. Flat, private, and free of significant obstructions, the lot provides outstanding design flexibility for your dream home. Located in the heart of Old Oakville, you'll enjoy an unbeatable lifestyle just steps to vibrant downtown Oakville, boutique shopping, renowned restaurants, cafés, parks, the lakefront, and the Oakville GO Station, with convenient access to major highways. Opportunities to acquire premium building lots this close to downtown are exceptionally rare. Whether you're an end user ready to build your forever home or a builder seeking a premier location, this is a property that offers both exceptional value and limitless potential. Experience the charm, prestige, and walkable lifestyle that make Old Oakville one of the GTA's most coveted communities. A truly rare offering in an irreplaceable location.

235 Douglas Avenue, Oakville
$1,950,000
4 Beds ⋅ 4 Baths ⋅ W13215862 MLS ⋅ Oakridge Heights BLDG.
SPECTACULAR !! "One of a Kind" 2630 Sqft Unit, South/West facing Luxury Condo offering Panoramic RAVINE AND SIXTEEN MILE CREEK Views. 3 Spacious Bedrooms (plus one), 4 Baths, extra large Den with w/o Balcony overlooking Wooded Ravine. Private Sauna, Large Family Room w/Elegant Fireplace and Ravine Views. Two Private Balconies overlook Sixteen mile Creek and Wooded Ravine. A Fabulous location in Old Oakville, offers 2 Parking Spots, Double Size Locker, Walk to 'Go" Train, Shops, Restaurants, Downtown Oakville and Lake. Ideal for Couple downsizing or Family in need of a Nanny suite. Gleaming Hardwood Floors , Crown Molding, Elegant Lighting, in a unique 3 building development with security gate, sitting up on a hill overlooking nature.

50 Old Mill Road Unit 503, Oakville