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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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  • 27 Park Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5792005

    27 Park Avenue Old Oakville Oakville L6J3X9
    Main Photo: 27 Park Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5792005
    • Photo 1: 27 Park Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5792005
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    • Photo 39: 27 Park Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5792005
    $11,900,000
    Freehold
    Status:
    Active
    MLS® Num:
    W5792005
    Bedrooms:
    4
    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 details
    Listed by RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • Ph 160 Trafalgar Road in Oakville: Old Oakville Condo for sale : MLS®# W5644139

    Ph 160 Trafalgar Road Old Oakville Oakville L6J3G6
    Main Photo: Ph 160 Trafalgar Road in Oakville: Old Oakville Condo for sale : MLS®# W5644139
    • Photo 1: Ph 160 Trafalgar Road in Oakville: Old Oakville Condo for sale : MLS®# W5644139
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    • Photo 8: Ph 160 Trafalgar Road in Oakville: Old Oakville Condo for sale : MLS®# W5644139
    $8,999,000
    Condo
    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 details
    Listed by REXIG REALTY INVESTMENT GROUP LTD., BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • 208 331 Sheddon Avenue in Oakville: Old Oakville Condo for sale : MLS®# W5822643

    208 331 Sheddon Avenue Old Oakville Oakville L6J1X8
    Main Photo: 208 331 Sheddon Avenue in Oakville: Old Oakville Condo for sale : MLS®# W5822643
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    • Photo 32: 208 331 Sheddon Avenue in Oakville: Old Oakville Condo for sale : MLS®# W5822643
    $5,698,000
    Condo
    Status:
    Active
    MLS® Num:
    W5822643
    Bedrooms:
    4
    Bathrooms:
    5
    The "Chisholm" Is 4,065Sf Of Elegance With An Additional 890Sf Of Covered Outdoor Space. This Sole, 2-Storey End-Unit Has A Private Walk-Up And Showcases A Private Elevator From The Temperature-Controlled Parking Garage With 3 Parking Spots, Fitness Centre & Yoga Studio! Gourmet Kitchen With 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. Retreat To The 5-Piece Ensuite With Radiant In-Floor Heating, Spacious Dressing Room Or Walk-Out To The Private Rear Terrace With Rough-Ins For A Built-In Bbq & Fire Pit. Stroll To The Shops And Bistros Of Old Oakville's Historic Main Street, Harbour And Beautiful Lakeside Parks. More details
    Listed by KELLER WILLIAMS EDGE REALTY, BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • Ph1 300 Randall Street in Oakville: Old Oakville Condo for sale : MLS®# W5613960

    Ph1 300 Randall Street Old Oakville Oakville L6J1R1
    Main Photo: Ph1 300 Randall Street in Oakville: Old Oakville Condo for sale : MLS®# W5613960
    • Photo 1: Ph1 300 Randall Street in Oakville: Old Oakville Condo for sale : MLS®# W5613960
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    $5,488,800
    Condo
    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 details
    Listed by RE/MAX ESCARPMENT REALTY INC., BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • 184 Chartwell Road in Oakville: Old Oakville House (2 1/2 Storey) for sale : MLS®# W5842354

    184 Chartwell Road Old Oakville Oakville L6J3Z8
    Main Photo: 184 Chartwell Road in Oakville: Old Oakville House (2 1/2 Storey) for sale : MLS®# W5842354
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    • Photo 32: 184 Chartwell Road in Oakville: Old Oakville House (2 1/2 Storey) for sale : MLS®# W5842354
    $5,299,000
    Freehold
    Status:
    Active
    MLS® Num:
    W5842354
    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 details
    Listed by SUTTON GROUP QUANTUM REALTY INC., BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • 151 E Lakeshore Road in Oakville: Old Oakville Property for sale : MLS®# W5819514

    151 E Lakeshore Road Old Oakville Oakville L6J 1H3
    Main Photo: 151 E Lakeshore Road in Oakville: Old Oakville Property for sale : MLS®# W5819514
    • Photo 1: 151 E Lakeshore Road in Oakville: Old Oakville Property for sale : MLS®# W5819514
    $4,850,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    W5819514
    Total Area:
    5,950 sq. ft.
    Great Opportunity To Own A Fully Leased Asset Downtown Oakville. Tenants Onefiveone Social And Marble Slab Creamery On The Retail Level And 5 Apartments (One 2 Bedroom Suite, Two 1 Bedroom Suites And 2 Bachelor Suites) On The Second Floor. Great Location Downtown, Next To Anthropologie, Close Tot He Town Square, Surrounded By Great Amenities, Other Fantastic Restaurants, High End Retail And Close To Parking. More details
    Listed by LACEBY REAL ESTATE LIMITED, BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • 269 Chartwell Road in Oakville: Eastlake Property for sale : MLS®# W5826047

    269 Chartwell Road Eastlake Oakville L6J3Z7
    Main Photo: 269 Chartwell Road in Oakville: Eastlake Property for sale : MLS®# W5826047
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    • Photo 13: 269 Chartwell Road in Oakville: Eastlake Property for sale : MLS®# W5826047
    $4,799,000
    Freehold
    Status:
    Active
    MLS® Num:
    W5826047
    Almost 1/2 Acre Level Building Lot With Great Proportions Located In One Of The Most Sought-After Neighbourhoods For New Construction In South East Oakville. Bordered By Mature Trees And Offers Great Privacy From The Surrounding Homes. Rl1-0 Zoning, 30% Lot Coverage And 29% Rfa. New Survey Attached. Approved By Committee Of Adjustments For A Minor Variance Allowing For The Construction Of An Almost 5,600 Sq Ft Home With Walk-Up Basement And 3-Car Garage. More details
    Listed by CENTURY 21 MILLER REAL ESTATE LTD., BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • 269 Chartwell Road in Oakville: Eastlake House (2-Storey) for sale : MLS®# W5826226

    269 Chartwell Road Eastlake Oakville L6J3Z7
    Main Photo: 269 Chartwell Road in Oakville: Eastlake House (2-Storey) for sale : MLS®# W5826226
    • Photo 1: 269 Chartwell Road in Oakville: Eastlake House (2-Storey) for sale : MLS®# W5826226
    • Photo 2: 269 Chartwell Road in Oakville: Eastlake House (2-Storey) for sale : MLS®# W5826226
    • Photo 3: 269 Chartwell Road in Oakville: Eastlake House (2-Storey) for sale : MLS®# W5826226
    • Photo 4: 269 Chartwell Road in Oakville: Eastlake House (2-Storey) for sale : MLS®# W5826226
    • Photo 5: 269 Chartwell Road in Oakville: Eastlake House (2-Storey) for sale : MLS®# W5826226
    • Photo 6: 269 Chartwell Road in Oakville: Eastlake House (2-Storey) for sale : MLS®# W5826226
    • Photo 7: 269 Chartwell Road in Oakville: Eastlake House (2-Storey) for sale : MLS®# W5826226
    $4,799,000
    Freehold
    Status:
    Active
    MLS® Num:
    W5826226
    Bedrooms:
    4
    Bathrooms:
    8
    Almost 1/2 Acre Lot With Great Proportions Located In One Of The Most Sought-After Streets For New Construction In South East Oakville. Stunning French Chateau Style Exterior With Generous 3 Car Garage (1 Tandem Spot). This Lot Is Bordered By Mature Trees And Offers Great Privacy From The Surrounding Homes. Opportunity To Landscape To Your Taste While Incorporating The Existing Sport Court. Close To All Amenities Including The Oakville Go, Downtown, The Lake And The Best Private/Public Schools In Oakville. More details
    Listed by CENTURY 21 MILLER REAL ESTATE LTD., BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • 122 Burnet Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5829559

    122 Burnet Street Old Oakville Oakville L6K1C1
    Main Photo: 122 Burnet Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5829559
    • Photo 1: 122 Burnet Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5829559
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    • Photo 38: 122 Burnet Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5829559
    • Photo 39: 122 Burnet Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5829559
    • Photo 40: 122 Burnet Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5829559
    $4,498,000
    Freehold
    Status:
    Active
    MLS® Num:
    W5829559
    Bedrooms:
    3
    Bathrooms:
    4
    Coastal Inspired West Harbour Gem! Completely Redesigned By Studio H & Hallmark Homes. Exudes Luxury & Attention To Detail Offering The Highest Quality Finishes T/O. Beautiful White Oak Flrs, Exquisite Trim Work, Paneling, Mouldings & High Ceilings On All Levels. Main Flr Includes Cozy Formal Sitting Rm W/ Gas Fp And Lrg Dining Rm For Entertaining & Family Dinners. Sun Rm Has Been Enclosed And Redone W/ Windows, Gas Fp And Heated Flrs Allowing You To Enjoy Its Solace Year Round. Gorgeous Designer Lighting And An Abundance Of Pot Lighting. Great Rm Boasts Vaulted Ceiling Adjacent To The Custom Designed New Kitchen, Island And Cabinetry. Gourmet Top Line Appls And Attractive Porcelain Countertops. Sep Entrance Off Mud Rm W/ Lrg Main Flr Laundry Rm And Enchanting Powder Rm. Property Features Two Private Spaces For Sitting And Enjoying The Lovely Gardens. Primary Bdrm, Spa Like Ensuite & Two Add'l Bdrms And Bath Finish Upper Lvl. Bright Ll Offers Add'l Bdrm & Bath, Gym, Ofc And Media Rm! More details
    Listed by RE/MAX ABOUTOWNE REALTY CORP., BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • 36 Anderson Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5824667

    36 Anderson Street Old Oakville Oakville L6K1A5
    Main Photo: 36 Anderson Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5824667
    • Photo 1: 36 Anderson Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5824667
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    • Photo 32: 36 Anderson Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5824667
    $4,199,850
    Freehold
    Status:
    Active
    MLS® Num:
    W5824667
    Bedrooms:
    3
    Bathrooms:
    4
    Magnificent New Custom-Built Luxury Home In Coveted Quiet Neighbourhood In Old Oakville Close To Top Schools, Including Appleby College, The Marina, Parks, Trails, Downtown Oakville, & Lake Ontario. This Remarkable Two-Story Transitional Open Concept Property Includes An Elevator W/ 8Ft Tall Cub Spanning 3 Levels, Skylights, Hardwood Floors Throughout, Expansive Floor-To-Ceiling Windows, 10Ft. Ceilings On Main & Second Level, Large Quartz Stone Fireplace, & Heated Porcelain Tile On The Entire Lower Level. Feel Secure W/ Top Security System Cameras & Alarm. Venetian Front Windows W/ Privacy. Spacious 4 Bedrooms W/ 3 Juliette Balconies Overlooking The Lake. 4 Baths (2 W/ Smart Heated Toilet/Bidets) & Large Soaker Therapeutic Tub In Master. Large Covered Veranda. More details
    Listed by RE/MAX REALTY ENTERPRISES INC., BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • 287 River Side Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5839423

    287 River Side Drive Old Oakville Oakville L6K3N3
    OPEN HOUSE: Dec 11, 2022
    02:00 PM - 04:00 PM EST
    Open House on Sunday, December 11, 2022 2:00 PM - 4:00 PM
    Main Photo: 287 River Side Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5839423
    • Photo 1: 287 River Side Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5839423
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    • Photo 37: 287 River Side Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5839423
    • Photo 38: 287 River Side Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5839423
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    • Photo 40: 287 River Side Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W5839423
    $3,995,000
    Freehold
    Status:
    Active
    MLS® Num:
    W5839423
    Bedrooms:
    5
    Bathrooms:
    4
    Rare Ravine Property On Mature Tree Lined Street. Over Half An Acre Of Fully Fenced Yard With Riparian Rights, And Views Of Ravine And Water From Almost Every Room. The Large Kitchen Offers 2 Dine-In Eating Areas, Loads Of Granite Counter Space, Gas Stovetop, Double Stacked Ovens, Warming Drawer, Entire Wall Of Cabinets, And Butcher Block Island W/Additional Storage. The Second Floor Has A Private Primary Bedroom With A 5-Piece Ensuite, Walk In Closet And Balcony. Also Find A Large Space For A Home Office, Loft, 4 Additional Bedrooms, A 3-Pc Bathroom, And 4-Pc Bathroom. Find Abundant Natural Light Throughout, 3 Fireplaces, Hardwood Flooring, Pot Lights, Lots Of Storage, And Stairs Down To The Ravine. Enjoy Summers Kayaking From Your Private Waterfront, And Winters Skating On The River In Your Backyard. More details
    Listed by RE/MAX ESCARPMENT REALTY INC., BROKERAGE
    Tanya Crepulja
    Steven Fontes
  • Ph9 300 Randall Street in Oakville: Old Oakville Condo for sale : MLS®# W5745354

    Ph9 300 Randall Street Old Oakville Oakville L6J1R1
    Main Photo: Ph9 300 Randall Street in Oakville: Old Oakville Condo for sale : MLS®# W5745354
    • Photo 1: Ph9 300 Randall Street in Oakville: Old Oakville Condo for sale : MLS®# W5745354
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    • Photo 35: Ph9 300 Randall Street in Oakville: Old Oakville Condo for sale : MLS®# W5745354
    $3,985,000
    Condo
    Status:
    Active
    MLS® Num:
    W5745354
    Bedrooms:
    1
    Bathrooms:
    3
    Penthouse 9 Features 2678 Square Feet Of Luxurious Living Space. Chef's Downsview Kitchen With Breakfast Bar And Marble Countertops Featuring Top-Of-The-Line Gourmet Appliances. Spectacular Cabinetry Surrounding A Large Subzero Wine Fridge Draws The Eye To The Impressive Dining Room. The Great Room Has A Gas Fireplace, An Ideal Space For Entertaining. The Principal Bedroom Offers A Walk-In Closet And A 5-Piece Spa-Inspired Ensuite Bathroom With A Separate Water Closet. Featuring A Five Piece Ensuite, The Den Acts Like A Spacious Bedroom. Crestron Automation System Controls Your Lighting, Shades, And Security System. Take Your Private, In-Suite Elevator Up To The Mezzanine Level Room That Could Be Used For Entertainment Or Stunning Office Space. Step Out Onto The Private Rooftop Terrace With An Observation Deck To Look Out Over Lake Ontario. Parking For Three Cars And A Large Storage Locker. This Boutique Building Is The Epitome Of The Ultra-Luxury Condominium Lifestyle. More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA, BROKERAGE
    Tanya Crepulja
    Steven Fontes
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Data was last updated December 9, 2022 at 08:55 PM (UTC)
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