Old Oakville
Home Cost
$1,107,200
Average Family Income
$705,865
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About Old Oakville
Old Oakville is the original settlement of the area dating back to the 1800’s, and the historic buildings and grandiose waterfront mansions create an impressive visual punch. This is luxury at its finest, and this is probably Oakville’s most expensive and most desirable area.
Who Lives Here
There is plenty of old money in Old Oakville, and you’ll find lots of affluent families with kids, as well as many empty nesters and seniors. There’s also an influx of young professionals populating those condos and town homes. This is a very popular area, and those who can afford it absolutely adore it.
What's Great About It?
As with most of Oakville, there’s a beautiful waterfront and refreshing greenery at every turn. What’s unique about this area, however, is that historic feel throughout much of it—something noticeably different from the newer areas in Oakville. There’s a unique charm that continues to appeal to people. Go for a stroll and you’ll see for yourself!
Schools
St. Vincent Elementary (JK-Gr 8)
St. Joseph Elementary (Gr 5-8) (Fr. Imm.)
St. Thomas Aquinas Secondary (Gr 9-12) (Fr. Imm.)
Maple Grove Elementary (JK-Gr 8)
New Central Elementary (JK-Gr 6)
E.J. James Elementary (Gr. 1-8) (Fr. Imm.)
Oakville Trafalgar Secondary (Gr 9-12) (Fr. Imm.)
Many of Old Oakville’s affluent residents choose to send their children to one of the many surrounding private schools such as MacLachlan College, Dearcroft Montessori, St. Mildred’s-Lightbourn School, West Wind Montessori Jr. High School, and Appleby College.
Homes for sale in Old Oakville
Looking for listings in Old Oakville for sale? You’re only seeing some of the listings available here. To see them all, just click the ‘Signup’ or ‘Login’ links below.
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489 Lakeshore Road E in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8183300
489 Lakeshore Road E Old Oakville Oakville L6K 1G4 $27,850,000Freehold- Status:
- Active
- MLS® Num:
- W8183300
- Bedrooms:
- 5
- Bathrooms:
- 8
Welcome to 489 Lakeshore Road East, a truly rare and exceptional estate crafted by the renowned Ferris Rafauli, nestled in the prestigious enclave of southeast Oakville along the serene shores of Lake Ontario. This rare one-acre property boasts a remarkable 16,000+ square foot steel-frame home, meticulously designed to showcase unparalleled craftsmanship and timeless elegance. Every detail of this exquisite residence speaks to a dedication to luxury living, from its concrete structure to its five bedrooms and eight baths, eight fireplaces, three kitchens, and elevator for seamless access to all levels. Indulge in the ultimate relaxation with amenities such as a Versace inspired indoor pool, built-in spa and gym, dry sauna, and cabana with a full kitchen. The property also features a four-car garage, 600-amp electrical service, in-floor heating, and cutting-edge building operation systems, all complemented by award-winning landscaping. More detailsListed by ENGEL & VOLKERS TORONTO CITY- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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199 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8217968
199 Chartwell Road Old Oakville Oakville L6J 3Z7 $11,995,000Freehold- Status:
- Active
- MLS® Num:
- W8217968
- Bedrooms:
- 5
- Bathrooms:
- 7
Magnificent gated estate on a meticulously landscaped 3/4 acre lot, on Oakville's coveted ' Street of Dreams'. This Architectural monument was designed & Built by one of the World's most renowned master builders of uber-luxury residences. Solid limestone construction, slate rf, copper eaves & stone pillars. 11,000 + sq ft of exq finishes t/o incl walls & ceilings, exotic woods, imported marbles, features inc cstm elevator,2 storey Grt Rm w 24 ft 2 sided limestone f/p open to stately Library .Chef's dream kit w ebony & walnut cabinetry, marble counters & serving pantry. Frml Din Rm o/l front gardens. 2nd lvl w Grand Prim retreat w lavish 6 pc ensuite & boutique-style Dressing Rm, 3 addtnl beds w lux ensuites & opulent LA Rm. LL w 5th bed, 2 baths, hm office, s/o/t/a hm thtr, gym, Recreation area, wet bar & wine Rm. Resort-style b/yrd w inground salt-water pool w cascading jets, wtfl spa, fire bowls, linear f/p, stone decking & gorgeous Cabana!! Steps to lake & town. Exc school distict! More detailsListed by SOTHEBY`S INTERNATIONAL REALTY CANADA- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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26 Trafalgar Road in Oakville: Old Oakville House (3-Storey) for sale : MLS®# W8191522
26 Trafalgar Road Old Oakville Oakville L6J 3E7 $9,998,000Freehold- Status:
- Active
- MLS® Num:
- W8191522
- Bedrooms:
- 6
- Bathrooms:
- 9
Nestled at the base of Trafalgar Road, in the heart of Old Oakville, this home boasts an impressive Walk Store of 94 out of 100. With lake front access, steps to lakefront trails, parks, the marina, boutique stores and fine dining. This expansive property boasts dimensions of 155 by 104 ft., and offers a sweeping vista of the ever-changing lake, endless horizons, and magnificent sunrises. Steeped in a rich history, the house has undergone a transformation into a stunning residence spanning 10,000 sq. ft. across three levels. With 4 bedrooms and an additional 2, totaling 6beautifully appointed bedrooms, and a generous 9 bathrooms, this home exudes refined luxury .Step inside to discover a custom kitchen seamlessly blending classic charm modern convenience. Luxurious amenities abound, from the elevator to the lofty ceilings adding grandeur, a captivating walk-in wine cellar, a walk-out basement ,an expansive area for a nanny or in-law suite, a well-equipped gym and a loft. More detailsListed by CENTURY 21 LEADING EDGE REALTY INC.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
210 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8086756
210 Chartwell Road Old Oakville Oakville L6J 3Z8 $9,998,000Freehold- Status:
- Active
- MLS® Num:
- W8086756
- Bedrooms:
- 4
- Bathrooms:
- 6
Exceptional Californian inspired Custom rebuild on one of Oakvilles most sought-after streets. Modern Luxury awaits you at 210 Chartwell road.Gren Weis contemporary interior design and architecture along with Mazengas craftsmanship, created over 7500 sf of spectacular living space offering the perfect entertainers home. Chefs' kitchen with double islands and oversized walk-in pantry, living and dining room with 18ft ceilings, all with floor to ceiling windows. Upstairs offers 3 large bedrooms, all with ensuites and upper level living room. Built on an expansive 102 x 235lot with tiered manicured gardens, gunite saltwater pool and hot tub, custom fountain, and year-round turf grass. Ideally located, just a walk to Downtown Oakville. More detailsListed by RE/MAX ABOUTOWNE REALTY CORP.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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511 Macdonald Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8156614
511 Macdonald Road Old Oakville Oakville L6J 2B7 $7,950,000Freehold- Status:
- Active
- MLS® Num:
- W8156614
- Bedrooms:
- 5
- Bathrooms:
- 7
A Visionary Architectural Concept Focused On Hosting And Gatherings Is Showcased In This Beautiful Property, Characterized By Meticulous Attention To Detail & Craftsmanship, Seamless Continuity, Minimalist Aesthetics, And Distinctive Artisanal Finishes That Flow Effortlessly Throughout The Spacious Open Floor Plan And Into The Bespoke Kitchen. The Dining Area And Family Room Are Enveloped By Modern Floor-To-Ceiling Glass Doors That Elegantly Retract, Seamlessly Blending Indoor And Outdoor Living Spaces. An Arresting Curved Staircase Adds To The Visual Allure. The Primary Bedroom, Reminiscent Of A Luxurious Spa, Exudes A Hotel-Inspired Ambiance With Stylish Features. The Spacious Lower Level Offers A Range Of Entertainments, Including A Rec. Room, Billiards Area, Fitness Studio, And Theatre. 3 Indoor Fireplaces, Outdoor Fire Pit And Fireplace.Thoughtful Landscaping Enhances The Property's Privacy Plus Pizza Oven To Enjoy. Minutes To Downtown Restaurants, Shops, Entertainments And More! More detailsListed by FORESTWOOD REAL ESTATE INC.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
128 Balsam Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8209234
128 Balsam Drive Old Oakville Oakville L6J 3X5 $7,798,000Freehold- Status:
- Active
- MLS® Num:
- W8209234
- Bedrooms:
- 7
- Bathrooms:
- 10
Welcome to 128 Balsam Drive in South East Oakville, One of the Prettiest, Most Exclusive and Desirable Streets in the Greater Toronto Area!This Extraordinary Custom Built Homes is just steps to Oakville's Historic Downtown Shopping District, Plethora of Private Schools and Plenty of Waterfront Parks. This Gorgeous Home Boots Over 7,500 sf of Luxurious Living Space on a Generous 100x152" Lot. The Main Floor Is an Entertainer's Dream! Offering a Hollywood Style Kitchen with Wolf Stove, A Massive Centre Island Equipped with 2 Sinks and Plenty of Sitting space, Open Concept to Family Room and Breakfast Area All which Overlook the Lovely Backyard. This Home has 7 Bedrooms Each with it's own Personal Ensuite, 9 Bathrooms, 5 Gas Fireplaces, a Beautiful Walnut Wine Cellar and MUCH more! This Home was Built with All the Comforts and Luxuries in mind. More detailsListed by RE/MAX ESCARPMENT REALTY INC.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
200 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8009782
200 Chartwell Road Old Oakville Oakville L6J 3Z8 $6,995,000Freehold- Status:
- Active
- MLS® Num:
- W8009782
- Bedrooms:
- 5
- Bathrooms:
- 7
Exceptional gated estate home nestled on a spectacular 100' x 225' lot on Oakville's most coveted street of dreams, completely reconstructed in 2020 with over 7500 sf luxury finished living space on trend finishes & manicured gardens with the timeless character and curb appeal. The main level boasts airy kitchen w/ finest cabinetry opens to a spacious family room that's meticulously designed for entertaining, the office, formal living room, piano lounge and 3 season screened Muskoka room.Luxuriate in the principal suite w/linear gas fireplace, dual ensuites, separate walk-in closets & a boutique-like dressing room.Private walk out balcony overlooks the private Muskoka like yard with towering trees. All 3 additional upper level bedrooms each have private en-suites and generous closets.Take the main floor slide or the stairs to a fully finished lower level with recreation, games rooms, gym, 5th bdrm, full bathroom & plenty of storage.2 laundry rooms provide optimal laundry efficiency. More detailsListed by RE/MAX HALLMARK ALLIANCE REALTY- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
177 Gloucester Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8053260
177 Gloucester Avenue Old Oakville Oakville L6J 3W3 $6,250,000Freehold- Status:
- Active
- MLS® Num:
- W8053260
- Bedrooms:
- 6
- Bathrooms:
- 8
Nestled in Old Oakville, this exceptional home stands on a 0.581-acre lot. The 6,800 sf residence (total) is within walking distance to Downtown, the Community Centre, the lake. The thoughtfully designed layout features a main floor office w/ custom features, a chef's dream kitchen w/ dbl islands, formal dining rm, expansive family rm, (gas fireplaces), mudroom, sauna. Upper level - 5 spacious bedrooms, incl the luxe primary, each w/ ensuite, w/i closets, & fab laundry rm. The lower level offers versatility w/ recreation room (fireplace), guest bedrm, 3-piece bathrm, theater, wine cellar. The extraordinary outdoor oasis features extensive deck/patios, hot tub, cabana, a saltwater pool, a basketball court, firepit, mature trees. A 2018 renovation brought an addition w/ extensive updates throughout the home, & a walk-up to the garden. Triple car garage. More than just a home, it is a rare blend of location, functionality, & outdoor enjoyment, representing the pinnacle of upscale living. More detailsListed by SOTHEBY`S INTERNATIONAL REALTY CANADA- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
133 Gloucester Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8172368
133 Gloucester Avenue Old Oakville Oakville L6J 3W3 $6,000,000Freehold- Status:
- Active
- MLS® Num:
- W8172368
- Bedrooms:
- 5
- Bathrooms:
- 7
Stunning Executive home located in prestigious Old Oakville only footsteps to downtown and Lake Ontario. This Beautiful home boasts premium hardwood floors throughout, chef's gourmet kitchen with 2 sub-zero fridges, 2 miele dishwashers, 60in wolf range, large center island with prep sink, spacious living and family rooms with French doors, cozy wood burning fire place, built in sub-zero refrigeration unit for refreshing drinks, massive mudroom with radiant heated floors and ample storage, 2 main floor powder rooms, peaceful office with stunning view overlooking tranquil back yard oasis with inground pool and immaculately manicured landscaping. second floor boasts 4 generously sized bedrooms with a true master bedroom retreat with soaring vaulted ceilings, spa bathroom with steam room and radiant heated floors, luxuriously sized walk in closet, upstairs laundry. Basement features guest bedroom, two full baths, rec room, large windows, additional laundry room and walk up to back yard. More detailsListed by RIGHT AT HOME REALTY- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
9 Lambert Common in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W7379330
9 Lambert Common Old Oakville Oakville L6K 0H6 $5,580,000Freehold- Status:
- Active
- MLS® Num:
- W7379330
- Bedrooms:
- 4
- Bathrooms:
- 6
Quiet Cul De Sac, Walk Distance To Appleby College. Rare Oakville Lakefront Estate Home W/Limestone Exterior & Contemporary Interior. Total 12 Spots: 6 Inside Parking Spaces & 6 Outside Parking Spaces. 1st Flr 11 Ft, 2nd Flr 10 Ft, Basement 9Ft With Wet Bar, Billiard Room, Gym Room & Media Rm. Upper Level All Bedrooms W/Ensuite. TWO Master Rm With Big Terrace + Lakeview, 3 Fireplaces, All Bathrooms With Heated Floor. $$$ Upgrade Finishes$$$ More detailsListed by BAY ST. POPULAR REAL ESTATE- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
21 Second Street in Oakville: Old Oakville House (1 1/2 Storey) for sale : MLS®# W8100018
21 Second Street Old Oakville Oakville L6J 3T1 $5,500,000Freehold- Status:
- Active
- MLS® Num:
- W8100018
- Bedrooms:
- 3
- Bathrooms:
- 2
RIPARIAN WATERFRONT IN DOWNTOWN OAKVILLE. Potential abounds! Fantastic opportunity to renovate, or build a new custom home. The possibilities are endless in this secluded waterfront residence where location and privacy are second to none. Charming main floor offers a functional layout with an open concept living and dining room as well as a separate family room with views to the water! There are 2 main floor bedrooms, a 3-pc bathroom and a conveniently located main floor laundry room. Upstairs, the principal retreat provides a walk-in closet, 4-piece bathroom, 3 skylights, and a den with walkout to the upper flat roof where you can watch sailboats gliding across the Lake. Rare, detached double car garage. Located on an approximately 67ft x 170ft riparian lot, graced by mature trees and magnificent lake views off the 2-tiered deck to the water. More detailsListed by RE/MAX ESCARPMENT REALTY INC.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
376 Lakeshore Road W in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8237332
376 Lakeshore Road W Old Oakville Oakville L6K 1G1 $4,990,000Freehold- Status:
- Active
- MLS® Num:
- W8237332
- Bedrooms:
- 5
- Bathrooms:
- 4
Gorgeous home located in OLD OAKVILLE, gleaming Hrdwd Flrs throughout, kitchen w/ 6-pic B/I appl, 3 Bdrms on 2nd flrs, bsmt rec rm, a wet bar & 2 bdrms. Conveniently located close to the GO train station, Transit, bus stop, & within WALKING DISTANCE to Lake Ontario, Appleby College & Other Private, Public & Catholic Schs, YMCA, Parks, Restaurants, Hwys, & Shops. More detailsListed by ROYAL LEPAGE GOLDEN RIDGE HARBORELITE REALTY- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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