
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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199 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W7058484
199 Chartwell Road Old Oakville Oakville L6J 3Z7 $13,750,000Freehold- Status:
- Active
- MLS® Num:
- W7058484
- 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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27 Park Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W6744700
27 Park Avenue Old Oakville Oakville L6J 3X9 $11,488,888Freehold- Status:
- Active
- MLS® Num:
- W6744700
- Bedrooms:
- 5
- Bathrooms:
- 9
Situated In The Orchard Beach Community Of Old Oakville, This Home Is The Epitome Of A Lakeside Home Styled In The Architecture Of The Hamptons Surrounded By Towering Trees, Perennial Gardens And Inspiring Lake Views. Designed By Gus Ricci & Select Finishes By Studio H. 10,000+ Sf Of Living Space On A Massive Lot W/ Excess Of One Million Dollars Spent On Landscaping. The Interior Features Finishes Specified To The Highest Level. Marble Heated Flrs, 10" Wide Plank White Oak Flring, Stylish Light Fixtures, High Ceilings On All 3 Levels, 4+1 Bdrms, 2 W/ Study Areas, 9 Custom Designed Baths. Main Flr Is Completed W/ Parlour, Ofc, Laundry Rm, Formal Dining Rm & Servery, Great Rm And Mud Rm Off Heated Garage. Fully Fin Bsmt Incl Two Full Baths, Gym, Extensive Wine Cellar, Theatre Rm & Bar, Bdrm, Mech Rm, Media Rm, Safe Rm, Cedar Closet, Ample Storage Areas & Stairs To Garage. A Short Walk To Town, Proximity To The Lake, Outstanding Finishes - One Of The Most Gracious Newer Homes In The Area 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
-
247 Donessle Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W7019940
247 Donessle Drive Old Oakville Oakville L6J 3Y8 $10,900,000Freehold- Status:
- Active
- MLS® Num:
- W7019940
- Bedrooms:
- 6
- Bathrooms:
- 9
Welcome to 247 Donessle Drive, located the heart of Old Oakville. Designed by Architect Bill Hicks, Interior Designer Robin Nadel and Landscape Architect Daniel O'Brien, this one of a kind custom built home boosts over 11,000 sq. ft. of exceptional living space across all levels. This home has 5 bedrooms, 9 bathrooms, a Chef's dream kitchen designed by Downsview with high end appliances and marble counter tops, Butlers pantry and elevator .Living room, formal dining room, office, servery, great room and mudroom you will find on the main level. Enjoy the walk up from the lower level that includes spa, a gym, kitchen, old world wine cellar, theatre room, wet bar, two play rooms, recreation room, a cedar closet, two full baths, laundry, and back hall stairs to the main floor and heated 4 car garage. The home has an updated Crestron Automation and Security System with exterior and interior cameras. More detailsListed by CENTURY 21 MILLER REAL ESTATE LTD.- 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
-
26 Trafalgar Road in Oakville: Old Oakville House (3-Storey) for sale : MLS®# W6806164
26 Trafalgar Road Old Oakville Oakville L6J 3E7 $10,750,000Freehold- Status:
- Active
- MLS® Num:
- W6806164
- Bedrooms:
- 6
- Bathrooms:
- 9
Nestled graciously at the base of Trafalgar Road, this property adorns a vast expanse measuring 155' x 104', offering a panorama of endless horizons. This heritage residence has undergone a complete metamorphosis, emerging as a magnificent domicile spanning approximately 10,000 square feet across 3 Levels. It encompasses 4+2 resplendent bedrooms and an opulent total of nine bathrooms. It's worth noting that this illustrious dwelling earned its share of the spotlight as a featured locale in Season 6 of the renowned television series, "Suits." The residence proudly boasts a bespoke custom kitchen, complementing its classical charm with contemporary convenience. The amenities within are nothing short of luxurious, featuring an elevator, lofty ceilings that breathe grandeur, an alluring walk-in wine cellar/vault, a walk-out basement, a spacious nanny/in-law suite, a well-appointed gymnasium, a third-level loft, and the practicality of dual laundry facilities. 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®# W7300198
210 Chartwell Road Old Oakville Oakville L6J 3Z8 $9,998,000Freehold- Status:
- Active
- MLS® Num:
- W7300198
- Bedrooms:
- 4
- Bathrooms:
- 6
Listed 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
-
200 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W7028046
200 Chartwell Road Old Oakville Oakville L6J 3Z8 $7,500,000Freehold- Status:
- Active
- MLS® Num:
- W7028046
- 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
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233 King Street in Oakville: Old Oakville House (3-Storey) for sale : MLS®# W7061506
233 King Street Old Oakville Oakville L6J 1B6 $6,750,000Freehold- Status:
- Active
- MLS® Num:
- W7061506
- Bedrooms:
- 6
- Bathrooms:
- 5
233 King Street is one of Old Oakville's finest estate homes. This home offers over 6900 sq. ft. of living space on 4 levels. Situated on 0.351 acres lot, this home is brimming w/ character details such as the original stone floors in the sunroom, stained glass windows, 2 woodburning fireplaces w/ intricate mantles, and plaster moldings. The kitchen is well-appointed w/ Egyptian marble counters, built-in appliances, and hardwood floors. This home offers gracious living spaces, w/ the formal living and dining rooms or in the family room and music/sunroom. The primary bedroom includes a sitting room, dressing room, WIC, and ensuite. Two additional bedrooms, a full bathroom, and a linen room. The third floor is comprised of 3 more bedrooms, 2 bathrooms, and a cedar walk-in closet. It's a rare opportunity to own a piece of history while enjoying the gardens, stone patios, and the saltwater concrete pool and spa. Don't miss the chance to make this remarkable property your own. 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
-
9 Lambert Common in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W6023260
9 Lambert Common Old Oakville Oakville L6K 0H6 $6,390,000Freehold- Status:
- Active
- MLS® Num:
- W6023260
- Bedrooms:
- 4
- Bathrooms:
- 6
Rare Oakville Lakefront Estate Home W/Limestone Exterior & Contemporary Interior. Quiet Cul De Sac, Walk Distance To Appleby College. Total 10 Spots: 6 Inside Parking Spaces & 4 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. 2 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
-
133 Gloucester Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W7269652
133 Gloucester Avenue Old Oakville Oakville L6J 3W3 $6,000,000Freehold- Status:
- Active
- MLS® Num:
- W7269652
- 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
-
537 Carson Lane N in Oakville: Old Oakville Property for sale : MLS®# W7335548
537 Carson Lane N Old Oakville Oakville L6J 3Z5 $5,995,000Freehold- Status:
- Active
- MLS® Num:
- W7335548
REMARKS FOR CLIENTS ATTENTION DEVELOPERS, BUILDERS, INVESTORS, location location location. 2 building lots side by side in prime south east Oakville walking distance to the downtown. With new Bill 23 you would be able to bring for approval to construct one three unit building on each piece of land. Driving distance to the GO train and close to public transit. Seller and Agent make no representation as to development time and Town uses. Buyer to verify with Town. Potential to obtain CMHC MLI select take out financing due to having greater than 5 units on a continuous piece of land. Seller and Agent make no representation as to Developer/Builder/Investor for financing. Buyer to verify on their own. 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
-
52 Chartwell Road W in Oakville: Old Oakville House (Other) for sale : MLS®# W7335516
52 Chartwell Road W Old Oakville Oakville L6J 3Z5 $5,995,000Freehold- Status:
- Active
- MLS® Num:
- W7335516
ATTENTION DEVELOPERS, BUILDERS, INVESTORS, location location location. 2 building lots side by side in prime south east Oakville walking distance to the downtown. With new Bill 23 you would be able to bring for approval to construct one three unit building on each piece of land. Driving distance to the GO train and close to public transit. Seller and Agent make no representation as to development time and Town uses. Buyer to verify with Town. Potential to obtain CMHC MLI select take out financing due to having greater than 5 units on a continuous piece of land. Seller and Agent make no representation as to Developer/Builder/Investor for financing. Buyer to verify on their own. 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
-
32 Brookfield Road in Toronto: Bridle Path-Sunnybrook-York Mills House (2-Storey) for sale (Toronto C12) : MLS®# C6170940
32 Brookfield Road Bridle Path-Sunnybrook-York Mills Toronto M2P 1A9 $5,888,000Freehold- Status:
- Active
- MLS® Num:
- C6170940
- Bedrooms:
- 4
- Bathrooms:
- 5
Urban Retreat - Magnificent Stone Mansion Nestled on Expansive Estate Property in Majestic Hogg's Hollow. This expansive home presents a unique and enchanting urban retreat. Experience the best of both worlds with a seamless fusion of city living and the tranquility of an upscale resort-like ambiance. The residence boasts an open-concept design, a delightful backyard oasis, and a gourmet eat-in kitchen. Unwind in the lavish master suite with an adjacent sitting room, with walk-in closets, and in close proximity to the park. More detailsListed by MANORLEAD GROUP 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

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