Century Home Updated for Modern Living.Timeless charm meets modern sophistication in Old Oakville.This meticulously maintained home sits on a premium 72'X150' lot & spans almost 5,000 sq ft of thoughtfully designed living space,with large,light-filled rooms and a main floor layout perfect for entertaining.A generous principal bdrm retreat was added in 2010,and extensive renovations by architect John Wilmott & Whitehall Construction were  2020. Step inside and discover a bright entryway that flows seamlessly into an elegant living room with wood burning f/p and a formal dining room perfect for special occasions.The stylish yet practical custom kitchen showcasing Povey cabinetry & high-end appliances that will appeal to any chef.Convenient coffee nook & a sleek hidden appliance cabinets maintain a streamlined,clutter-free aesthetic.Sun-filled windows throughout the kitchen and family room overlook the expansive backyard,while the family room centers around a charming Vermont Castings wood-burning f/p.A large private office,complete w/built-in cabinetry and pocket doors,provides the ideal workspace.Upstairs,discover the luxurious primary bdrm retreat featuring walk-in closet & 5-pc ensuite w/heated floors.3 addt'l bdrms incl 1 perfect for a home gym,a full 4pc bathroom with heated floors along with 2 generous-sized linen closets complete the upper level.The lower level offers exceptional entertainment spaces with a recreation area,a home theatre for movie nights,and craft room for your creative pursuits.A convenient laundry room with abundant storage adds practical value.Outside,the oversized detached insulated and heated 2-car garage includes 2 attached sheds for storage.The driveway accommodates 8 vehicles while a full irrig system complete w/planter drip lines maintains the lush landscaping.Located steps from vibrant downtown,Whole Foods & lake,w/convenient access to the GO & highways,this home delivers convenience & style in Oakville's most desirable location.

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247 Douglas Ave, Oakville, Ontario L6J3S2

Welcome to this stunning, never before lived in custom-built 3-storey townhouse in the heart of downtown Oakville, offering 3 bedrooms, 4 bathrooms, and over 3,100 total square feet of luxurious living spaces. Designed for sophisticated urban living, this home features a private in-home elevator providing easy access to all levels, from the finished basement with heated concrete floors to the expansive rooftop terrace. The chef's kitchen boasts top-of-the-line Sub Zero, Wolfe and Miele appliances, custom white oak cabinetry with gold touches, and gorgeous marble countertops. An oversized 11' island overlooks the bright living and dining area complete with a custom plaster fireplace design flanking built-in cabinetry. French doors lead to a walk-out balcony, enhancing the living space with an outdoor area for bbquing and relaxing. The second floor offers two generously sized bedrooms, each with its own ensuite bath and walk-in closet, providing comfort and privacy for family and/or guests. The spacious laundry room with full size stacked washer/dryer is conveniently located just outside these bedrooms. A lovely primary retreat space is found on the third floor, featuring a private balcony, a huge walk-in closet, and a spa-inspired 5-piece ensuite featuring heated floors, a soaker tub, and smart toilet. Additional highlights include a massive rooftop terrace ideal for outdoor entertaining, and on a clear day you can catch a view of Lake Ontario. A finished double car garage with sleek epoxy heated floors, as well as a heated driveway, make up the garage space, while providing direct access to the home. Showcasing premium finishes throughout, this home is ideally located steps from Oakville's lakefront, shops, dining, and top-rated schools. Offering a flexible move in date, this turn key residence is a rare opportunity to own a brand-new, luxury home in one of Oakville's most desirable neighborhoods.

78 Trafalgar Rd, Oakville, Ontario L6J2S7

Step inside this heritage home and feel the unmistakable charm of Old Oakville-warm, character-filled, and full of possibility. With nearly 2600 sq. ft. of thoughtfully preserved total space, this 3-bedroom residence offers not only history and lifestyle, but also an exceptional foundation for those who want to infuse their own design vision over time. The main floor centres around a spacious and inviting foyer/vestibule, setting a graceful tone for the home. Just beyond, the office/living room features a wood-burning fireplace framed by built-in bookcases, creating a warm, intimate space ideal for reading, conversation, or quiet evenings by the fire. It is a true reflection of the home's period craftsmanship. The layout then transitions into a combined living and dining room, an elegant, sunlit space anchored by a second gas fireplace. Multiple windows bring in natural light, while the walkout to the backyard extends everyday living into the garden.  The kitchen, small but full of charm, includes a breakfast bar and efficient layout suited for modern daily routines. A main floor 3-piece bath adds welcome convenience-an uncommon advantage in a home of this vintage. Upstairs, three comfortable bedrooms provide peaceful retreat, each offering its own character and bright, airy ambiance thanks to the home's generous window count. Outdoors, the yard unfolds into a lush, mature garden-a true plant lover's paradise. Thoughtful plantings, natural privacy, and seasonal colour create a tranquil backdrop.  This home is perfect for buyers who value authenticity and appreciate the opportunity of living in one of Oakville's most storied neighbourhoods. Warm, welcoming, and rich in character, it offers a lifestyle built on history, charm, and community. It invites you to honour its history while making it distinctly your own.

289 Spruce St, Oakville, Ontario L6J2G8

Transitional Elegance in the Heart of Olde Oakville. A rare property on one of the community's most coveted streets. Experience refined living in this exceptional residence- set on a triple lot over 1/2 acres with an impressive 154.73 ft frontage, curated for those who value privacy, design and indoor-outdoor living at its finest. Beautifully reimagined in 2024, the main level showcases a sophisticated blend of transitional elegance and casual upscale comfort, perfect for both everyday living and effortless entertaining. A Main Floor Redesigned for Modern Luxury. Step inside to wide-plank oak hardwood floors, luxurious finishes, and stunning sightlines to the property's park-like grounds. The brand-new designer kitchen is a true showpiece, featuring: Main kitchen+ second "messy kitchen" for concealed prep, storage, and small appliances. Silk granite farmhouse sink with brushed gold gooseneck faucet and gold hardware accents throughout- Oversized picture window overlooking the gardens. Square island with integrated fridge/freezer drawers. Quartz countertops & full-height backsplash in both kitchens. Built-in wine/beverage station. Dedicated coffee bar. A walk-out from the dining room and a large picture window open to views of the serene screened-in sun porch, creating a seamless flow for indoor-outdoor enjoyment. The magnificent great room features dramatic cathedral ceilings, a stone wood-burning fireplace (forced-air assist) with aged beam mantel, and wiring/rough-ins for a full theatre- quality sound system. A second walk-out continues to the sun porch- offering year-round enjoyment framed by nature. Flexible living spaces: Third floor loft/suite ideal for guests, teens, studio or office.4+1 bedrooms, 4 bathrooms, and over 5200 sq ft of total finished living space. Finished basement with heated floors in media room (or current gym). Dust-free heat system with individually controlled room zones. **Remarks continued in Attachments

317 Gloucester Ave, Oakville, Ontario L6J3W8

RARE WATERFRONT OPPORTUNITY IN OLD OAKVILLE! Discover a rare opportunity to own a Waterfront Property in the heart of Old Oakville. This charming brick bungalow backs onto Sixteen Mile Creek, offering breathtaking views and endless potential. Situated within a highly sought-after school catchment area and just a short walk to Downtown Oakville, the GO Station, shops and restaurants, this property combines location, lifestyle, and opportunity in one exceptional package.

288 Trafalgar Rd, Oakville, Ontario L6J3H2

Nestled in the heart of Oakville's famed Heritage District, this delightful 1 1/2 storey home combines classic charm with modern comfort. With its picture-perfect board and batten wood exterior, whimsical front porch, the curb appeal is simply irresistible. The spacious living and dining areas flow seamlessly into a gracious family room with feature gas fireplace where natural light pours in through a wall of windows that overlook the lush backyard. The 2nd level features 2 bedrooms complete with brand new custom built-ins for added storage and 3-piece bathroom with skylight. Separate entrance to the home's lower level leads to the large recreation space with electric fireplace, extra large bedroom, and newly renovated bathroom(2020) and laundry room. This home offers a rare combination of character and convenience, with the best of Oakville at your doorstep. Just 5 minute walk to GO Train station, Whole Foods, Indigo, Starbucks, Shoppers Drug Mart, and LCBO, you'll enjoy effortless access to all your daily essentials. Top-rated schools, great local artisanal shops, and picturesque parks are also within walking distance, making this an unbeatable location for families and professionals alike.

411 Trafalgar Rd, Oakville, Ontario L6J3H8

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 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.

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PH1 300 RANDALL St, Oakville, Ontario L6J0G2

Welcome to a once-in-a-lifetime opportunity in the heart of Old Oakville's most exclusive enclave. Situated on a premium 100 x 88 lot on prestigious Chartwell Road, this charming residence is the last remaining original home this close to Lake Ontario offering unmatched potential in a neighbourhood where properties of this caliber rarely become available. Thoughtfully updated throughout, the home blends timeless character with modern convenience, featuring a newer roof, furnace, A/C, updated wiring, and plumbing. The location is truly unparalleled just a 10-minute walk to the boutiques, restaurants, and cafes of vibrant downtown Oakville, yet nestled on a quiet, tree-lined street steps from the lake. Importantly, this is not a designated historical home, giving buyers the flexibility to enjoy the existing residence or design and build a custom dream home in one of Canadas most desirable communities. Whether you're looking to move in, renovate further, or build new, this is your final chance to secure a prime piece of Chartwell Road this close to the water.

42 Chartwell Rd, Oakville, Ontario L6J3Z4

Rare Opportunity to own this Charming Family Home nestled in the Heart of Old Oakville in one of THE most sought after neighbourhoods. Very well maintained 1 1/2 storey home is situated on a fully landscaped 50' x 141.8' lot on a quiet, tree-lined cul de sac. The home is surrounded by covered porches and decks so you can enjoy the ambiance and stillness of nature at its best and still be close to everything! Originally purchased over 40 years ago as a quaint cottage, renovated in 1992 and now boasting large principal rooms, a sunken, oversized 19'8 x 18'6 family room featuring a reclaimed brick-faced, woodburning fireplace with barn board mantel and matching bar with sliding doors leading to a Muskoka like backyard. Expansive windows across the back of the house lead to the 36'4 x 14'6 rear deck! Winter or summer, special memories will be made at your family gatherings and celebrations, ideal for relaxing evenings or entertaining guests. Offering over 2,050 sq. ft. of above ground inviting living space, this property perfectly blends classic charm with modern comfort. 3+1 spacious bedrooms, 4 bathrooms, large living room currently being used as a separate dining room plus a partial finished basement provides ample space for families of all sizes. Main Floor Bedroom/Office/Den and updated bathroom. Gleaming hardwoods and ceramics adorn the foyer and main floor. Large pantry and abundant cupboards in the spacious kitchen with double sink. Separate laundry room on the main floor with laundry tub, folding counter and lots of under counter storage. On the rear of the property there are two additional stand alone structures for summer/garden equipment or workshop/studio with electricity. This property offers endless possibilities for renovation or addition. No homes across the street for ultimate privacy. Just minutes from top-ranked public and private schools, Downtown Oakville, Whole Foods, LCBO, charming shops, the lakefront, parks, and a walk to GO transit.

322 Pine Ave, Oakville, Ontario L6J2J9

Welcome to this Sun-Filled Corner "Captivate" Model! Discover this bright & spacious 2-bedroom, 2-bath suite in the Rain Condominiums by Empire Communities. This desirable corner unit offers an open-concept living & dining area with floor-to-ceiling windows, 9' ceilings, crown moulding, smooth ceilings, & engineered hardwood floors. Step out from every room onto a wrap-around 300 sqft. balcony, perfect for relaxing or entertaining. The modern kitchen features S/Steel appliances and a glass tile backsplash. The primary bedroom includes a 3-piece ensuite, W/in closet, & walk-out to the balcony. The second bedroom with mirrored closet & balcony access. Additional highlights include 2 parking spaces next to each other & a locker. Enjoy resort-style amenities: an indoor pool, hot tub, cold plunge, sauna, gym with yoga studio, party room, library, rooftop terrace with BBQs & lounge areas, 24-hour concierge, EV chargers, car wash, visitor parking, guest suites, & secure parcel lockers. Free Wi-Fi in gym, library, & pool area.Just steps to Oakville GO Station, Kerr Village, restaurants, shops, & a movie theatre. Only minutes to QEW, downtown Oakville, & the Oakville Harbour & marina. Bonus: The upcoming Gemini South Tower nearby will be only 10 storeys, per the builder, so your view of Toronto and Mississauga SkyLines, lake and Sixteen Mile Creek, will not be obstructed!!!!

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1503 65 Speers Rd, Oakville, Ontario L6K0J1

Welcome to Ashbury Square in the heart of Downtown Oakville. This stylish two-storey loft-style condo offers just over 760 square feet of beautifully designed living space with soaring ceilings and abundant natural light. The open-concept main floor features an updated kitchen and stainless steel appliances, hardwood floors, and a dedicated office or den area-ideal for working from home. Upstairs, the spacious lofted bedroom includes a walk-in closet and views to below Step outside and you're in the vibrant core of Downtown Oakville-surrounded by boutiques hops, award-winning restaurants, cozy cafés, and just steps to the lake, the marina, and scenic waterfront trails. Enjoy refined urban living in one of Oakville's most coveted, walkable neighborhoods. Includes underground parking and locker.

404 185 Robinson St, Oakville, Ontario L6J7P6

Welcome To Prestigious Old Oakville! An Absolutely Stunning Century-Home Situated On A Sprawling 57 x 167 Foot Lot, Tucked Behind The Mature Pines That Provide The Privacy & Serenity You Covet. This Spacious Custom-Built Home With Classic Covered Front Porch Is Your Cottage In The City, Complete With Front & Backyard Oases! Four Bedrooms Plus A Nanny Suite In The Lower Level, And Four Full Bathrooms, The Highlight Of The Home Is A Main Floor Family Room With Soaring 12-Foot Timber Ceilings, Brick Fireplace, & Walkout To The Landscaped Backyard. Not One, But TWO Main Floor Home Offices Offer Convenience & A Lifestyle That Few Homes In Old Oakville Can Provide. Fantastic Basement Rec Room Has Been Renovated Into A Home Gym, Ready For Its New Fitness Enthusiast Owner! Steps To Oakville Trafalgar Community Centre, Wallace Park Tennis Club, & Oakville Curling Club. Whole Foods, Starbucks, & LCBO Two Blocks Away On Cornwall Road, And Only An 8-10 Minute Walk To Prime The LakeShore Road Strip!

409 Reynolds St, Oakville, Ontario L6J3M3

Welcome to 116 Chartwell Road, a stunning Net Zero certified modern masterpiece in Southeast Oakville, blending luxury, sustainability, and wellness. Designed by David Small Designs this eco-friendly home offers advanced insulation, a geothermal system paired with a solar array. This ensures clean, energy-efficient living, reducing exposure to pollutants and superior indoor air quality for a healthier, more comfortable home. The open-concept layout bathed in natural light has floor-to-ceiling windows and a striking pyramid skylight. Beautiful wire-brushed white oak flooring with in-floor heating is throughout the home. The gourmet kitchen features a Diamante Quartzite island, custom lacquered cabinetry and top-tier Gaggenau appliances. Outdoors, a stylish covered patio with dual Kenyon barbecues, a stainless-steel hot tub and surround sound creates an inviting space for relaxation and entertaining. The main floor primary suite is a serene retreat with a walk-through closet and spa like ensuite. The home office with garden views and a floor-to-ceiling oak bookcase offers a calming workspace. Upstairs, two spacious bedrooms with ensuites ensure comfort for family or guests. The lower level is an entertainment hub with a fitness room, a recreation room with a built-in bar and pool table and an additional bedroom with ensuite. Smart home technology seamlessly integrates audio-visual, lighting, and security systems, controlled via intuitive apps and two master control rooms, ensuring peace of mind. A tandem four-car garage with a hydraulic lift and EV charging, plus extra outdoor parking welcomes the car enthusiast.

116 Chartwell Rd, Oakville, Ontario L6J3Z6

Discover this remarkable character home nestled in the heart of Old Oakville,and located mere steps to the lake and waterfront trail & park. This renovated residence offers approximately 2877 sq ft above grade plus a finished lower level with impressive high ceilings, creating an abundance of living space.The home's signature wrap-around porch provides stunning lake views and southwest exposure,overlooking meticulously landscaped gardens bursting with hydrangeas and boxwoods.Inside, the thoughtfully designed layout features a spectacular white kitchen with quartzite counters, a large center island, and premium built-in appliances that flow seamlessly into the living room and informal dining area with direct porch access.The dining room showcases a wood-burning f/p, while newer hardwood floors create continuity throughout.The main floor also includes a practical mudroom,powder room,office space,and a family room addition with soaring vaulted ceilings.Upstairs, the primary bedroom suite boasts a luxurious  ensuite with marble flooring, soaker tub,and glass shower and walk-in closet.3 additional bedrooms (one currently used as an office), a sparkling main bathroom with walk-in shower, and a convenient laundry room with new W/D complete this level.The LL offers versatility with a spacious rec room,a 5th bedroom,and  3 pc bathroom.Utility/Storage Room gives you lots of space for off season item storage.Newer electrical, heating & cooling systems, and plumbing throughout.Step outside to beautiful private landscaped gardens where your porch or patio is perfect for al fresco dining.The double car garage and driveway provide parking for 6 cars. This prime location places you within walking distance of downtown Oakville and its fabulous shops,restaurants,Lake Ontario and Oakville Club.Oakville GO train and highway access just minutes away,making it perfect for families seeking convenience and character in one of Oakville's most desirable neighborhoods.LUXURY CERTIFIED

212 King St, Oakville, Ontario L6J1B5

Exceptional opportunity to own a beautifully updated 5-bedroom, 4-bath executive home on a rare 50 ft*350 ft lot in the heart of prestigious Old Oakville. Nestled on a quiet, tree-lined street, this over 4,000 sq ft residence features a stunning great room with 18' vaulted ceiling and French doors opening to a huge two-level deck overlooking a private Muskoka-style backyard oasis, offering the perfect blend of cottage-style living and city living comfort. The bright open-concept kitchen with skylights and stainless steel appliances is ideal for entertaining, while the main-floor in-law/guest suite with private ensuite provides flexibility for multi-generational families. Freshly painted, carpet-free, and filled with natural light, the home includes new LED lighting, two furnaces, Heatpump and AC. With two separate basement entrances and a walk-out lower level, there's exceptional potential for a private suite, home office, or future expansion. Walking distance to the new community centre, lakeshore, top-rated schools, parks, and transit, and just minutes to the QEW, this property offers the perfect balance of luxury, privacy, and convenience - a rare chance to live, invest, or build your dream home in one of Oakville's most prestigious neighborhoods.

435 Maple Ave, Oakville, Ontario L6J2J2

Opportunity to live in a custom-built home in sought-after Old Oakville. Prime location within walking distance to Downtown Oakville, shops, restaurants, and the lake. This 4+1 bedroom home offers 3,593 sq. ft. of above-grade living space plus a fully finished basement, totaling 4,428 sq. ft. Features include a double car garage with rear pass-through parking pad, built-in cabinetry throughout, and custom detailing and finishes. Additional highlights include walk-behind closets, custom skylight, built-in speakers, large window wells with oversized basement windows, European-influenced fencing and curbing, and an open-riser oak staircase with lighting. A beautifully designed home showcasing quality craftsmanship and attention to detail in one of Oakville's most desirable neighbourhoods. All Built-In Appliances, All Electric Light Fixtures, Custom Cabinetry, Cac, Garage Door Openers & Remotes. Hot Water Tank (Owned)

366 Galt Ave, Oakville, Ontario L6J3P3

Experience luxury living in this stunning, quiet, renovated penthouse suite located in one of Oakville's most desirable buildings. Boasting numerous upgrades, including a modern kitchen with stainless steel appliances, updated bathroom, elegant gas fireplace, newer flooring, and floor-to-ceiling windows that flood the space with natural light. The open-concept layout offers exceptional flow, while the spacious den easily serves as a second bedroom, nursery or a bright home office. The primary suite features large windows, a walk in closet.  Additional highlights include newer flooring throughout, Tall ceilings, in suite laundry, ample built in storage, and 2 parking spaces. Residents enjoy outstanding building amenities: indoor pool, sauna, fitness centre, party room with pool table, BBQ patio area, gated security, and ample visitor parking. All within walking distance to Oakville GO Station, Whole Foods, LCBO, Starbucks, and many local shops and restaurants, with easy QEW access just minutes away. All you need to do is just move in! don't miss your opportunity to call this penthouse home.

PH906 50 OLD MILL Rd, Oakville, Ontario L6J7W1

Welcome to Oakridge Heights, one of Oakville's most prestigious addresses, introducing the Birchwood model 1436 square foot, 2-bedroom, 2-bath and not one but 2 large balconies, rare combination of size, style, plus  2 parking spots. updated to perfection, this home offers an open, light-filled layout with south exposure overlooking the gardens. The unit has just been painted with Sherwin Williams Agreeable Gray. Hardwood floors throughout. The kitchen is combined with a lovely breakfast area and has a big pantry. The principal bedroom will easily accommodate a king size bed and has a huge walk-in closet completed with closet organisers plus entrance to a large private balcony. The sun filled living and dining room combination is large and will accomodate any size furniture, corner fireplace and entrance to a huge balcony.  For commuters, access to the Oakville GO station is a dream. A brisk 15 minute walk to downtown Oakville. Easy access to Whole Foods and other gourmet shopping is just down the road.

GLA1 60 Old Mill Rd, Oakville, Ontario L6J7V9

Discover the charm of Old Oakville in this beautifully crafted custom built home, offering nearly 3100 sq ft of finished living space. Thoughtfully designed with a modern influence, it features 9' ceilings, wide plank hardwood floors and custom millwork. The gourmet kitchen includes a large centre island, stainless appliances, granite counters, and a walk-in pantry. The open-concept living and dining area is perfect for entertaining and has a double garden door walkout to the private back yard. The main level flooring and hardwood stairs were just re-done with a rich, matte finish. Also conveniently located on the main floor is a 2pc bath and mudroom/laundry room with broom closet and convenient inside access from the garage. Upstairs, the spacious primary suite features a luxurious 5-piece ensuite with heated floors and a large walk-in closet. Two additional bedrooms are bright and well-sized with double door closets. The finished lower level adds a rec room, 4th bedroom, and 3-piece bath, ideal for overnight guests or a teen retreat. Professionally landscaped last year, the gardens include mature trees & perennials - an irrigation system makes for easy maintenance. The garage has been customized with epoxy floors, overhead storage and slat walls for organizing your tools & gear. Hockey enthusiasts will love the electric roll-down sports screen - perfect for target practice and protects the garage door from damage. Many other updates, including light fixtures and fresh interior painting make this home turn-key. Ideally situated in the heart of Old Oakville, walk to Oakville GO, Whole Foods, Downtown shops, restaurants, and parks from this prime cul-de-sac location. Timeless design, high-end finishes, and unbeatable location make this home a rare find.

437 Inglehart St, Oakville, Ontario L6J3J5

Versatile residential home in close proximity to Lakeshore with commercial zoning. Can easily be occupied as your own personal residence and offers good parking street exposure and one block walk to downtown west Oakville. The room measurements exclude the stairs and entryway areas.