
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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173 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5546658
173 Chartwell Road Old Oakville Oakville L6J3Z7 $10,750,000Freehold- Status:
- Active
- MLS® Num:
- W5546658
- Bedrooms:
- 4
- Bathrooms:
- 8
French Chateau Estate Living In The Heart Of South East Oakville. Timeless Elegance & Exceptionally Well Crafted.This Exclusive Residence Is Approx 8,000 Sqft Above Grade W/4,000+ Finished Sqft In The Walk-Out Ll, Sitting On A Private 0.7 Acre Lot. Exquisitely Finished W/Soaring Ceiling Heights, Walnut Scarlet O'hara Staircases, Heated Marble Slab, Extensive Built-Ins & Domani Kitchen & Servery. Primary Wing W/Portico, Lounge,Spa Ensuite & 2 Dressing Rms. More detailsListed by CENTURY 21 MILLER REAL ESTATE LTD., BROKERAGE- 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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Ph 160 Trafalgar Road in Oakville: Old Oakville Condo for sale : MLS®# W5644139
Ph 160 Trafalgar Road Old Oakville Oakville L6J3G6 $8,999,000Condo- Status:
- Active
- MLS® Num:
- W5644139
- Bedrooms:
- 3
- Bathrooms:
- 5
Welcome To The Penthouse - A Truly Unique Opportunity To Own The Entire Top Floor Of Oakville's Newest Luxury Residences Awaits At One60 Trafalgar. This Expansive 4,991 Sqft Unit Features 3 Bedrooms, 10 Foot Ceilings Throughout, A Fitness Studio, Library, And Its Own Elevator Entrance. Submerge Yourself In A Modernly Luxurious Lifestyle In The Custom Kitchen Featuring Custom Millwork Using European Materials And Miele Appliances. The Primary Bedroom Retreat Features Custom Walk In Closets & Its Own Exclusive Terrace Retreat. On Top Of The Well Thought Out And Inspiring Design Which Has Been Selected As A 2021 Bild & Canadian Home Builder's Association 2022 Design Finalist, All Buyers Will Receive Time With Our Design Teams To Truly Make It Yours. This Penthouse Unit Is Truly Bespoke And Allows Buyers The Opportunity To Customize To Their Liking. More detailsListed by REXIG REALTY INVESTMENT GROUP LTD., BROKERAGE- 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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115 Trafalgar Road in Oakville: Old Oakville Property for sale : MLS®# W5564782
115 Trafalgar Road Old Oakville Oakville L6J3G3 $8,990,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- W5564782
- Total Area:
- 18,000 sq. ft.1,672.25 m2
Prestigious Downtown Oakville Location! Freestanding Commercial Building, Never Before Offered For Sale! Retail Frontage On Trafalgar Road And Church St. Several Long Standing Tenants In This Two Storey Building, With Fully Finished And Rentable Basement Area. Structure Also Supports Construction Of Third Storey On Existing Structure For Additional Potential. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES LTD., BROKERAGE- 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
-
533 Carson Lane in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5697775
533 Carson Lane Old Oakville Oakville L6J6M3 $7,500,000Freehold- Status:
- Active
- MLS® Num:
- W5697775
- Bedrooms:
- 5
- Bathrooms:
- 7
Exemplary Custom-Built Home Located Oakville's Sought-After Neighborhood. Boasting 6500+ Sft Luxurious Living Space Incl. Heated Floors On Main/Lower Levels,Personal Elevator To All 3, Underground Parking. Sun-Filled 2-Storey Foyer Welcomes You To This Contemporary Home Boasting Modern Finishes. O/C Great Rm Feat. Almost 20' Ceiling O/L Entertainer's Covered Patio W/ Gas Bbq Hookup,Landscaped Yard. Two-Toned Gourmet Kitchen Boasts Massive Eat-In Centre Island,High-End Appl, Access To Butler Servery. Large Dining Room W/ B/I Speakers, O/L Beautifully Landscaped Front Yard. Retreat To Formal Living Rm Or Main Flr Office(Can Be Used As Ground Flr Bdrm) W/ Ensuite, W/O. Floating Stairs To Sky-Lit 2nd Flr. Primary Suite Feat. His/Hers W/I Closets,Ensuite Retreat. Add'l 3 Bdrms Feat Secured Closets,Heated Ensuites. Lower Level Haven For Auto Aficionados W/Access To Heated Underground 6-Car Garage,Car Turntable. Entertainer's Sanctuary In Rec Rm W/ Large Walk Up, Gym/Theatre, Full Bath, Bdrm More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES PHINNEY REAL ESTATE, BROKERAGE- 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®# W5702685
200 Chartwell Road Old Oakville Oakville L6J3Z8 $6,595,000Freehold- Status:
- Active
- MLS® Num:
- W5702685
- Bedrooms:
- 4
- Bathrooms:
- 7
A Gated Entrance Welcomes You To This Exceptional Estate Home.Nestled On A Spectacular 100' X 225' Lot On One Of Oakville's Most Soughtafter Signature Streets. Completely Reno'd To The Studs (2020),It Also Boasts A Reimagined Floor Plan & Rear Addition. Over 7500 Sqft Of Finished Living Space. Ideally Designed For Entertaining & Functionality Of A Family Home,It Feats An Airy Kitchen W/Top-Of-The-Line Appliances,Finest Cabinetry & An Oversized Quartz Waterfall Island That Opens To A Spacious Family Rm.Grand Server,Formal Dining Room W/ B/I Shelving & Exquisite Ceiling Detail.Slider Doors Open To Flood The Open Concept Family Room W/Natural Light & Reveal The Backyard Oasis With New Salt Water Pool (2020), Cabana.Main Flr Office, Lr ,Piano Lounge & 3 Season Screened-In Muskoka Rm.Luxuriate In The Principal Suite W/Linear Gas Fp,Dual Ensuites,Separate W/In Closets & A Boutique-Like Dressing Room.Private Walk Out Balcony Over Yard. Located In An Exceptional School District. More detailsListed by RE/MAX ESCARPMENT REALTY INC., BROKERAGE- 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
-
20 Lambert Common in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5614308
20 Lambert Common Old Oakville Oakville L6K 0H6 $6,380,000Freehold- Status:
- Active
- MLS® Num:
- W5614308
- Bedrooms:
- 4
- Bathrooms:
- 5
Custom-Built Luxury Home On A Private Cul-De-Sac South Of Lakeshore Rd. Over 6,000 Sf Living Space Features 10.5 Ft Crown Molding Ceiling, Soaring Fireplaces, Ambient Lightings, And Floor To Ceiling Windows Throughout. Custom Downsview Kitchen With Wolf Appliances. House Is Equipped With Central Sound System, Build-In Water Softener & Filter, Steam Humidifier, And Crestron Smart Home System. All Bathrooms Have Heated Floors. Over 900 Sf Shaded Terrace On The Main Level With Electric Snow Melting System. 9 Ft Clear Walk-Out Basement With Private Gym, Wet Bar, And Large Recreation Room, Filled With Natural Lighting. 4 Large Ensuite Bedrooms On The 2nd Floor, Master Bedroom Walkouts To Terrace. Custom Vestibule With Beam Ceiling. Steps To Lake And Appleby College. More detailsListed by HOMELIFE LANDMARK REALTY INC., BROKERAGE- 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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63 First Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5657210
63 First Street Old Oakville Oakville L6J3R5 $6,249,000Freehold- Status:
- Active
- MLS® Num:
- W5657210
- Bedrooms:
- 4
- Bathrooms:
- 6
With A Location South Of Lakeshore Road, This Newly Constructed Home Combines Exemplary Finishes And Exceptional Craftsmanship Highlighting The Timeless Traditional Interior Style. The Gourmet Eat-In Kitchen Is The Heart Of The Home - A Cohesive Blend Of Transitional Design Fused With Warm Charm. The Secondary Entrance Provides Ease-Of-Flow To The Hub Of The Home. Clever Design And Luxurious Finishes Are Carried Through To The Impressive Lower Level. More detailsListed by CENTURY 21 MILLER REAL ESTATE LTD., BROKERAGE- 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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184 Chartwell Road in Oakville: Old Oakville House (2 1/2 Storey) for sale : MLS®# W5725550
184 Chartwell Road Old Oakville Oakville L6J3Z8 $5,988,000Freehold- Status:
- Active
- MLS® Num:
- W5725550
- Bedrooms:
- 5
- Bathrooms:
- 6
This Estate Home Is Situated In The Most Sought-After Neighbourhood In Oakville. Stroll Into Beautiful Downtown Oakville And Enjoy All That Water Front Town Has To Offer Including Restaurants, Shopping, Parks And A Unique And Historical Vibe. This Home Is A Lifestyle Opportunity. Unique, Impressive, Ideally Located. With Over 7500 Sq Ft Of Luxury On A Premium 100 By 238 Lot. Updated And Elegant Classic Rms With An Open Concept Entertaining Kitchen, Sunken Great Rm With Vaulted Ceiling, And Walk-Out To A Magical Sunroom. A Stately Office With Built-In Cabinetry Makes For The Perfect Work At Home Space. Third Floor Loft Offers Bonus Bdrm And Full Bath. Basement Offers A Wet Bar, Pool Table, And Home Cinema For More Entertainment Opportunities. A Prof Landscaped Backyard With An Outdoor B/I Bbq, Bar * Fridge Make Family Time Effortless As You Enjoy Your Gas Firepit After An Afternoon By The Pool. Car Enthusiasts Will Savor The 4-Car Garage Which Offers A Private Year-Round Home Gym. More detailsListed by SUTTON GROUP QUANTUM REALTY INC., BROKERAGE- 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
-
208 331 Sheddon Avenue in Oakville: Old Oakville Condo for sale : MLS®# W5653523
208 331 Sheddon Avenue Old Oakville Oakville L6J1X8 $5,798,000Condo- Status:
- Active
- MLS® Num:
- W5653523
- Bedrooms:
- 4
- Bathrooms:
- 5
The "Chisholm" Is 4,065Sf Of Elegance W/ An Additional 890Sf Of Covered Outdoor Space. This Sole, 2-Storey End-Unit Has A Private Walk-Up & Showcases A Private Elevator, Has 3 Parking Spots, A Fitness Centre & Yoga Studio! Gourmet Kitchen W/ Walk-In Pantry, Sub-Zero, Wolfe, Asko & Miele Appliances & Elegant Wine Room. Custom Finishes Include Engineered Hardwood Floors, Oversized Centre Island & Charming Gas Fireplace. Savant Home Automation Integration System. More detailsListed by KELLER WILLIAMS EDGE REALTY, BROKERAGE- 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
-
57 Howard Avenue in Oakville: Old Oakville House (Bungalow) for sale : MLS®# W5659508
57 Howard Avenue Old Oakville Oakville L6J 3Y4 $5,750,000Freehold- Status:
- Active
- MLS® Num:
- W5659508
- Bedrooms:
- 2
- Bathrooms:
- 4
The Fourth Fully Custom Home Created By These Discerning Owners In Oakville Over The Span Of Two Decades, This Old Oakville Home Is Truly The Culmination Of A Lifetime Of Planning. Uniquely Designed To Take Full Advantage Of The Topography Of This Majestically Treed Corner Lot, This Home Features Two Ground Floors With Separate Accesses To The Stately Howard Avenue And Historic Carson Lane. The Authentic Cape Cod Design By Renowned Architect Richard Mann Features A Large Wrap-Around Porch, Balcony, Genuine Cape Cod Shingles, Extensive And Rare Natural Stone Features And Is Capped Off By A Private, Cozy Courtyard With A Saltwater Lap Pool And Expansive Spa By Betz Pools. The Private Driveway Compound Is Beautifully Landscaped, But Also Provides For Many Functional Uses Such As A Safe Play Area For Sports Like Basketball And Hockey, As Well As Overflow Parking When Needed. Extensive Millwork And Panelling Throughout From Brenlo Custom Wood Products. High Speed Elevator. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES LTD., BROKERAGE- 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
-
301 331 Sheddon Avenue in Oakville: Old Oakville Condo for sale : MLS®# W5653450
301 331 Sheddon Avenue Old Oakville Oakville L6J 1X8 $5,498,000Condo- Status:
- Active
- MLS® Num:
- W5653450
- Bedrooms:
- 4
- Bathrooms:
- 4
The "Mcdermott" Is 4,190Sf Of Sheer Luxury W/ An Additional 940Sf Of Outdoor Living Space. This End-Unit Penthouse Fills W/ Natural Light & Showcases A Semi-Private Elevator And 2 Parking Spots. Gourmet Kitchen W/ Walk-In Pantry, Sub-Zero, Wolfe, Asko & Miele Appliances & Elegant Wine Room. Custom Finishes Include Engineered Hardwood Floors, Oversized Centre Island & Charming Gas Fireplace. Savant Home Automation Integration System. More detailsListed by KELLER WILLIAMS EDGE REALTY, BROKERAGE- 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
-
Ph1 300 Randall Street in Oakville: Old Oakville Condo for sale : MLS®# W5613960
Ph1 300 Randall Street Old Oakville Oakville L6J1R1 $5,488,800Condo- Status:
- Active
- MLS® Num:
- W5613960
- Bedrooms:
- 3
- Bathrooms:
- 4
Reminiscent Of An Elegant Parisian Residence, Complete W/ A Stone Fa?ade, Classical Architecture & Only The Very Best Of Luxurious Finishes. This Is The Randall. Incredible Sun Filled Signature Penthouse Suite Features Approx 3,337 Sqft W/ A 2nd Story 386 Sqft Lounge Complete W/ Skylight-A Perfect Office, Gym Or Meditation Rm. With Soaring 12' Ceilings, Hrdwd Flooring & Its Own 1327 Sqft Se Facing Terrace Makes This Suite Truly One Of A Kind! The Grand Rotunda Entry W/ Its Slab Marble Flring Sets The Stage For The Rest Of This Opulent Suite. A Glamorous Kitch Feats Top-Of-The-Line Appliances, Distinctive Downsview Kitch, & A Lrg Island Which Opens To The Great Rm W/ Gas Fireplace & Dining Rm, An Ideal Space For Entertaining. The Principal Retreat Offers A Spacious Dressing Rm W/ Exotic Zebra Woods & Island. A 6-Pc Ensuite Bth W/ Heated Slab Marble Flring, Polished Nickel Faucets & Tempered Glass Shower Enclosure Complete The Principal Retreat. The Other 2 Bdrm's Have Their Own Ensuite. More detailsListed by RE/MAX ESCARPMENT REALTY INC., BROKERAGE- 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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