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44 Head Street in Oakville: 1002 - CO Central Single Family Residence for sale (1 - Oakville) : MLS®# 40743508
44 Head Street Oakville L6K 1L5 OPEN HOUSE: Jun 28, 202502:00 PM - 04:00 PM EDTOpen House on Saturday, June 28, 2025 2:00PM - 4:00PMOPEN HOUSE: Jun 29, 202502:00 PM - 04:00 PM EDTOpen House on Sunday, June 29, 2025 2:00PM - 4:00PM
$2,699,000Residential- Status:
- Active
- MLS® Num:
- 40743508
- Bedrooms:
- 4
- Bathrooms:
- 5
- Floor Area:
- 3,198 sq. ft.
Welcome to 44 Head St - an exceptional home in the heart of Oakville- steps from Kerr Village & downtown. Enjoy walkable access to local shops, dining & the lakefront-the perfect blend of convenience & tranquility. Offering almost 2200 sq ft plus fully finished basement ( 1015 sq ft), this remarkable residence offers timeless charm & modern functionality. Set behind pretty gardens, the Dark Slate wood siding & crisp white trim frame an inviting front porch-perfect for morning coffee or evening wine. Inside, 9' ceilings, hardwood floors, crown moulding & high baseboards create a refined, elevated feel. The entertainer’s kitchen showcases granite countertops, a large island, professional-grade appliances & generous storage, seamlessly flowing into the bright, open-concept living & dining areas. A cozy gas fireplace with custom millwork adds warmth, while French doors lead to the beautifully landscaped rear garden-perfect for relaxing or hosting outdoors. A versatile room on the main floor can serve as your personal office or den; it could also be transformed into a separate dining room if desired. Upstairs are 3 spacious bedrooms, each with ensuites with heated floors & walk-in closets . The lower level (9’ ceilings) includes a spacious family room plus 4th bedroom, 3pc bath & large laundry room. Storage is no issue in this home with the many custom built-in closets & cabinets. A detached garage with EV charger features a rare basement for even more storage! Plus there is parking for 6 cars on the extra long driveway. A fully fenced private rear yard, & unbeatable walkability to parks, shops, cafés & the waterfront make this turnkey property a rare offering. Meticulously maintained by the current owners, recent updates include powder room renovation (2024), driveway resurfaced (2024), exterior newly stained (2024) & insulation upgraded to R60 (2025). Ideal for empty nesters, downsizers & families. Don’t miss this opportunity to experience Oakville’s historic charm. More detailsListed by RE/MAX Aboutowne Realty Corp.- STEVE WILLIAMSON
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262 Mary Street in Oakville: 1020 - WO West Single Family Residence for sale (1 - Oakville) : MLS®# 40737290
262 Mary Street Oakville L6K 3V4
$2,980,000Residential- Status:
- Active
- MLS® Num:
- 40737290
- Bedrooms:
- 6
- Bathrooms:
- 5
- Floor Area:
- 4,383 sq. ft.
A Bold Statement In Design And Personality, This One-Of-A-Kind Art Deco-Inspired Home Is A Celebration Of Creativity, Quality, And Individuality. With Premium Finishes And Enduring Materials Throughout, This Residence Blends Luxury With Architectural Craftsmanship. The Exterior Features A 50-Year Metal Roof, Custom Concrete Driveway With Grass Inserts, Cedar And IPE Wood Façade, And Cedar-Lined Porch Ceiling. The Private Backyard Is Professionally Landscaped With Mature Trees, Perennial Gardens, Four Varieties Of Fruit Trees, Putting Green, Solarium (Updated With High-Efficiency Windows In 2019), Natural Gas BBQ Hookup, And Custom Garden Structures. Inside, The Heart Of The Home Is The Chefs Kitchen Which Impresses With 12 Built-In Miele Appliances, A 14-Ft Caesarstone Island, Custom Cabinetry, 3 Sinks, KOHLER Faucets, Pot Filler, In-Floor Heating, And Italian Tile. The Family Room Includes A Gas Fireplace And Surround Sound. The Foyer Welcomes With Granite Floors, A Glass/Stainless-Steel Staircase With Sapele Treads And Imported Designer Lighting. Formal Living And Dining Rooms Feature Crown Moulding, Custom Glass Pocket Doors, And A Stainless-Steel Fireplace. Upstairs, 5 Bedrooms Offer Bamboo Floors And Custom Lighting. The Primary Suite Has Mirrored Closets And A Bright Ensuite With Jacuzzi And Separate Shower. The Walk-Out Lower Level Offers A Private Entrance, Steam Shower, Rec Room, Home Office, And In-Law Suite Potential. Walk To Top Schools (Including Appleby College And French Immersion), Transit, Downtown, And The GO. A Rare Offering That Seamlessly Blends Design, Lifestyle, And Location - This Home Is Truly One To Experience. More detailsListed by The Agency- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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417 185 Robinson Street in Oakville: 1013 - OO Old Oakville Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40743832
417 185 Robinson Street Oakville L6J 7P6
$850,000Residential- Status:
- Active
- MLS® Num:
- 40743832
- Bedrooms:
- 1
- Bathrooms:
- 2
- Floor Area:
- 1,029 sq. ft.
This exquisite two-story penthouse in "The Ashbury," adjacent to the picturesque Town Square, epitomizes the pinnacle of luxurious living in the heart of Old Oakville. Its prime location offers unparalleled convenience, with effortless access to upscale restaurants, boutique shops, theatres, the serene lake, and the charming harbour, all immersing you in the town's vibrant and sophisticated ambiance. The expansive open-concept floor plan seamlessly integrates the living and dining areas, creating an opulent and inviting atmosphere, further enhanced by vaulted ceilings that amplify the sense of grandeur. The state-of-the-art kitchen boasts pot lights, a centre island, premium LG stainless steel appliances, and quartz countertops, providing a culinary haven. The living room, dining room, and den all share this elegant open-concept design, with the versatile dining room, which can double as a second bedroom, featuring a chandelier, sliding glass wall, and custom built-in shelving. The laundry area includes a stackable washer and dryer and built-in shelves for added convenience. Ascending to the second floor, the loft-style primary bedroom exudes sophistication with pot lights, his and her closets, and a lavish ensuite that includes a 4-piece bathroom with a tub/shower combo. An open-concept office completes the upper level, providing a perfect workspace. Residents of "The Ashbury" enjoy exclusive access to a stylish party room and a tranquil private garden, along with the added luxury of one underground parking space and a secure locker. More detailsListed by Royal LePage Real Estate Serv.- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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LOT 101 Douglas Avenue in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40743516
LOT 101 Douglas Avenue Oakville L6J 2B7
$4,290,000Residential- Status:
- Active
- MLS® Num:
- 40743516
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 3,188 sq. ft.
Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. The Douglas Collection is an extension of the inaugural development with an exclusive collection of seven homes located on Douglas Avenue. Distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. "The Chatsworth"; detached home with 48-foot frontage, between 3,188-3,204sf finished space w/an additional 1,000+sf (approx)in the lower level & 4beds & 3.5 baths. Utility wing from garage, chef’s kitchen w/w/in pantry+ generous breakfast, expansive great room overlooking LL walk-up. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment. More detailsListed by Century 21 Miller Real Estate Ltd.- STEVE WILLIAMSON
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LOT 102 Douglas Avenue in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40743594
LOT 102 Douglas Avenue Oakville L6J 2B7
$4,166,000Residential- Status:
- Active
- MLS® Num:
- 40743594
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 2,974 sq. ft.
Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. The Douglas Collection is an extension of the inaugural development with an exclusive collection of seven homes located on Douglas Avenue. Distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. "The Regal"; detached home with 48-foot frontage, between 2,974-3062 sf of finished space w/an additional 1,000+sf (approx) in the lower level & 4beds & 3.5 baths. Utility wing from garage, chef’s kitchen w/w/in pantry+ generous breakfast, expansive great room with glass sliders to rear patio. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment. More detailsListed by Century 21 Miller Real Estate Ltd.- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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901 55 Speers Road in Oakville: 1002 - CO Central Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40743275
901 55 Speers Road Oakville L6K 0H9
$529,000Residential- Status:
- Active
- MLS® Num:
- 40743275
- Bedrooms:
- 1
- Bathrooms:
- 1
- Floor Area:
- 650 sq. ft.
Discover modern elegance in this upgraded 1+den, 1-bath condo, offering just over 650 sq. ft. of stylish living space in the heart of Oakville’s trendy Kerr Village. Boasting over $35,000 in updates, this bright unit features brand-new appliances, including a fridge, dishwasher, stove, washer, dryer, and microwave, alongside a custom-designed island and bar area with quartz countertops extending into a seamless backsplash. The kitchen is further enhanced with upgraded handles, while the bathroom showcases a luxury vanity countertop. Custom storage solutions in all closets, fresh paint, and upgraded light fixtures elevate the space, complemented by floor-to-ceiling windows that fill the unit with natural light. A sprawling balcony, spanning the entire length of the condo, offers a perfect spot for relaxation or entertaining. Located steps from boutique shops, trendy cafés, and vibrant community amenities, this move-in-ready gem delivers a chic lifestyle in an unbeatable location. More detailsListed by RE/MAX Escarpment Realty Inc.- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
- 1 (905) 510-7141
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1 288 Reynolds Street in Oakville: 1013 - OO Old Oakville Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40743027
1 288 Reynolds Street Oakville L6J 3L4
$430,000Residential- Status:
- Active
- MLS® Num:
- 40743027
- Bedrooms:
- 2
- Bathrooms:
- 1
- Floor Area:
- 750 sq. ft.
Welcome to carefree, low-maintenance living in the heart of historic Old Oakville. This beautifully updated 2-bedroom apartment in the boutique Mayfair co-operative building offers a bright, inviting space ideal for those looking to downsize without compromise. Located on a quiet street just steps from charming downtown shops, restaurants, the lakefront, and the brand-new Oakville Trafalgar Community Centre, this home blends convenience, comfort, and community. Inside, you’ll find a thoughtfully renovated kitchen with stainless steel appliances, under-cabinet lighting, and a sleek, modern feel. The updated bathroom, newer energy-efficient windows, and durable pale wood grain flooring throughout add style and ease. Large windows flood the unit with natural light and offer views of the building’s lush, professionally maintained perennial gardens. This self-managed co-op includes a dedicated parking spot, storage locker, on-site laundry, and the option for garage rental. Monthly fees cover property taxes, heat, water, and parking — keeping costs predictable and hassle-free. Pride of ownership is evident throughout the building, thereby creating a strong sense of community and helping maintaining value for all. If you’re looking for a peaceful adult lifestyle in a walkable, established neighbourhood with great transit connections, this rarely offered co-op is a true gem. More detailsListed by RIGHT AT HOME REALTY BROKERAGE- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
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382 Trafalgar Road in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40739852
382 Trafalgar Road Oakville L6J 3H5 OPEN HOUSE: Jun 28, 202502:00 PM - 04:00 PM EDTOpen House on Saturday, June 28, 2025 2:00PM - 4:00PMOPEN HOUSE: Jun 29, 202502:00 PM - 04:00 PM EDTOpen House on Sunday, June 29, 2025 2:00PM - 4:00PM
$4,200,000Residential- Status:
- Active
- MLS® Num:
- 40739852
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 2,890 sq. ft.
Exquisite and reminiscent of New England charm, this lofted bungalow offers breathtaking views and unmatched privacy along Oakville's tranquil 16 Mile Creek. A testament to craftsmanship and design, this waterfront retreat boasts exclusive riparian rights and a private dock, inviting you to embrace the beauty of Oakville's scenic waterways year-round. In winter, skate or ski on the frozen creek or admire the snowy landscape from your sun-drenched living room. In summer, swim, fish, paddle to Oakville Harbour, or relax by the water, this home offers the feel of Muskoka, right in the city. A meticulous 2016 renovation elevated this residence with rich hand-scraped oak floors, solid wood doors, custom millwork, and elegant tray ceilings. The sprawling 1,700 sq. ft. premium Wolf PVC deck includes a hot tub oasis, integrated fire table, and motorized awnings, leading to a dock with a kayak launch, swim ladder, and floating dock. Glass-encased staircases on helical piers deliver striking architectural presence and unbroken sight lines to the creek. Inside, sophistication defines every detail. Floor-to-ceiling windows in the living room frame stunning ravine views and dramatic sunsets, while a gas fireplace with a live-edge mantel adds warmth. The chef's kitchen impresses with a leathered Taj Mahal quartzite island, Wolf and Miele appliances, and an integrated Sub-Zero fridge. Heated floors run throughout, including in the spa-like primary ensuite with marble floors, a rain shower, and double vanity. The lower level offers a linear fireplace, built-in bar, and walkout to the deck. A concrete-lined storage room playfully known as the Bomb Shelter provides additional functionality. Blending natural beauty, refined design, and year-round outdoor living, this one-of-a-kind property is just steps to downtown Oakville and the GO Train offering luxury, serenity, and convenience in equal measure. More detailsListed by Royal LePage Real Estate Serv.- STEVE WILLIAMSON
- RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
- 1 (905) 510-7141
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307 300 Randall Street in Oakville: 1013 - OO Old Oakville Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40740970
307 300 Randall Street Oakville L6J 0G2
$3,689,000Residential- Status:
- Active
- MLS® Num:
- 40740970
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 2,594 sq. ft.
Welcome to The Randall Residences, Oakville's most prestigious and architecturally iconic address. Rosehaven's award-winning architecture. Located in the heart of vibrant Downtown Oakville, Suite 307 is a timeless masterpiece offering just under 2,600 square feet of elegant living space, meticulously crafted with luxurious finishes and $$$ spent in custom upgrades. This 2-bedroom plus den, 2-bathroom suite features soaring ceilings, wide-plank hardwood flooring, and oversized windows that flood the space with natural light. The gourmet kitchen is a chef's dream, complete with top-of-the-line Wolf and Sub-Zero appliances, custom Downsview cabinetry, and a large island with marble countertops perfect for entertaining. The open-concept living and dining area offers a seamless fow, highlighted by a gas fireplace, designer lighting, and large double French doors with openings to a Juliette balcony overlooking Randall St. The spacious den, currently being used as a gym, can also function as a third bedroom or home office, offering flexibility to suit your lifestyle. Retreat to the primary suite, an oasis of calm with an elegant dressing room and a spa-inspired 6-piece ensuite bath featuring radiant heated floors, a soaker tub, and an oversized glass shower. A generously sized second bedroom and full ensuite complete this exceptional layout. Additional features include a full laundry room, motorized window coverings, two underground parking spaces, and a locker. Residents enjoy white-glove concierge service, rooftop terrace access, and a boutique hotel-style experience in one of Oakville's most exclusive buildings. Just steps from the lake, fine dining, shopping, and cultural experiences, this is refined living at its finest. More detailsListed by RE/MAX Aboutowne Realty Corp.- STEVE WILLIAMSON
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392 Kerr Street in Oakville: 1002 - CO Central Commercial for sale (1 - Oakville) : MLS®# 40737863
392 Kerr Street Oakville L6K 3B9
$119,000Business Opportunity- Status:
- Active
- MLS® Num:
- 40737863
Profitable Turnkey Variety Store for Sale Prime Oakville Location Excellent opportunity to own a highly successful, fully equipped variety store in the heart of Oakville. Situated on busy Kerr Street, this store is surrounded by dense residential neighbourhoods (homes & condos), with excellent foot traffic, ample parking, and great visibility.?? Key Highlights: Weekly Sales: $9,000$10,000-Low Rent: Just $6,700/month + taxes-High-Traffic Location: Strong exposure on Kerr Street-7-Door Walk-In Fridge: Ideal for cold beverages, beer & wine-Licensed Beer & Wine Sales: High-margin product lines-Turnkey Operation: Walk in and start earning from day one-Strong & Loyal Clientele: Solid customer base with repeat business Services Offered: ATM Bitcoin Terminal Western Union Passport PRO Photos PUDO Point (parcel pickup/drop-off) Gift Cards Mobile Top-Ups & Calling Cards Fresh Brewed Coffee?? Vape product approval pending landlord consent opportunity for additional revenue. This is a well-established, high-potential business with multiple income streams and room for growth. Perfect for an owner-operator or investor seeking a strong ROI. More detailsListed by ROYAL LEPAGE FLOWER CITY REALTY- STEVE WILLIAMSON
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8 Chartwell Road in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40738908
8 Chartwell Road Oakville L6J 3Z4
$9,750,000Residential- Status:
- Active
- MLS® Num:
- 40738908
- Bedrooms:
- 5
- Bathrooms:
- 6
- Floor Area:
- 4,185 sq. ft.
Step into a world of refined luxury and sophistication in this stunning waterfront property, where panoramic views of the city skyline captivate from the moment you enter. The expansive open-concept main level is anchored by a showstopping marble island, surrounded by high-end appliances. A discreetly positioned butler’s pantry offers effortless functionality. The eat-in kitchen, graced by soaring vaulted ceilings, seamlessly flows into a grand living room appointed with a gas fireplace—an idyllic setting to relax while soaking in the breathtaking waterfront vistas. For formal occasions, an elegant dining room sets the stage for lavish dinner parties and intimate family gatherings. A spacious main-floor family room adds versatility for everyday living and entertaining alike. The main level also features a beautifully appointed guest suite with a spa-inspired 5-pc ensuite bath. Even the laundry room has been elevated with heated floors, custom cabinetry, and expansive folding surfaces. Upstairs, discover three generously sized bedrooms, each with its own luxurious ensuite. The primary suite is a private sanctuary, complete with gas fireplace, exclusive balcony for sunset viewing, and an ensuite bathroom boasting a large soaking tub overlooking the water and spacious walk-in closet. Outdoors, the resort-style backyard is an entertainer’s dream. Host with ease at the built-in barbecue station, enjoy alfresco evenings under the covered patio, gather around the firepit, or unwind by the inground saltwater pool. With every amenity at your fingertips, this home redefines the art of luxurious living! Prime location just a short walk to downtown Oakville’s coffee shops, restaurants, boutiques, and lively festivals. Families will love the walkability to top schools like SMLS and Oakville Trafalgar High, while commuters enjoy easy access to the GO Train for a smooth trip to the city. More detailsListed by Royal LePage Real Estate Services Phinney Real Estate- STEVE WILLIAMSON
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406 123 Maurice Drive in Oakville: 1002 - CO Central Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40737666
406 123 Maurice Drive Oakville L6K 2W6
$2,325,990Residential- Status:
- Active
- MLS® Num:
- 40737666
- Bedrooms:
- 2
- Bathrooms:
- 3
- Floor Area:
- 1,508 sq. ft.
LIVE IN SOUTH OAKVILLE's NEWEST LUXURY BUILDING, THE BERKSHIRE. ONLY 7 REMAINING SUITES AVAILABLE. First class amenities including Concierge,Roof Top Oasis, Party Room, Gym with state of the art equipment,Visitor Parking. Brand New - Ready to Move In! Experience Luxury Living at The Berkshire Residences in South Oakville This 2-bedroom + den penthouse suite offers an unparalleled living experience, blending elegance with modern design. With 1,508 sq. ft. of thoughtfully crafted living space and an expansive 1,413 sq. ft. rooftop terrace, this home is perfect for entertaining and enjoying the outdoors. Additionally, a 198 sq. ft. balcony extends your living space, creating a seamless connection between indoor and outdoor areas. The suite boasts 10-foot ceilings and an array of refined details, including bespoke soft-close cabinetry, a porcelain slab countertop and backsplash, and a waterfall edge kitchen island. The upgraded kitchen is complemented by extended-height cabinets and a full 6-piece appliance package. Heated bathroom flooring and premium hardwood flooring throughout enhance the luxury feel. Impressive design features continue with Lincoln Park-style doors, upgraded vanities in all bathrooms, and high-quality upgraded tiles. These are just a few of the exceptional finishes that make this suite stand out. Convenience is key with 2 parking spots and a locker included, offering ease and practicality in your upscale living experience at The Berkshire Residences. Condo Fees approximate. Steps to Lake Ontario, waterfront promenades and downtown Oakville's finest shops and restaurants. IMMEDIATE OCCUPANCY AVAILABLE. no development charges More detailsListed by RE/MAX Escarpment Realty Inc.- STEVE WILLIAMSON
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Data was last updated June 28, 2025 at 09:50 AM (UTC)
Steve Williamson
Oakville ON REALTOR® - Call 905-510-7141 today
Location
A - 309 Lakeshore Road East
Oakville, ON, L6J 1J3