4-Bedroom House in Oakville

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House for sale: 53 THOMAS STREET, Oakville

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$3,250,000

53 Thomas Street, Oakville (1013 - OO Old Oakville), Ontario L6J 3A2

4 beds
3 baths
146 days

Thomas Street/William Street Nestled south of Lakeshore in the heart of Old Oakvilles historic district, this beautifully restored Georgian-style home, designed by Gren Weis, blends timeless character with modern updates. Steps from the lake, river, and vibrant Downtown, it offers an unmatched

House for sale: 74 HOWARD AVENUE, Oakville

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$5,750,000

74 Howard Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 3Y5

5 beds
4 baths
4 days

Lakeshore Rd / Chartwell Rd This English Country Garden home, framed by a storybook white picket fence, sits on a truly exceptional 100' x 168' lot in Orchard Beach, south of Lakeshore Rd in Old Oakville. Quiet and serene Howard Avenue, just two blocks long, is one of only a handful of streets

House for sale: 46 SECOND STREET, Oakville

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$8,479,000

46 Second Street, Oakville (1013 - OO Old Oakville), Ontario L6J 3T2

5 beds
6 baths
45 days

Cross Streets: Lakeshore Road E & Second St. ** Directions: Lakeshore Road E to Second St. Discover an extraordinary custom built residence in prestigious Old Oakville, where architectural excellence meets modern luxury just steps from the lake.This 2024 Net Zero Ready masterpiece represents

House for sale: 376 CHARTWELL ROAD, Oakville

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$4,400,000

376 Chartwell Road, Oakville (1013 - OO Old Oakville), Ontario L6J 4A3

6 beds
5 baths
43 days

MacDonald Rd./Chartwell Rd. A truly one-of-a-kind, professionally restored home that blends timeless Victorian charm with modern luxury. This stunning residence features 10-ft ceilings on the main floor, pot lights throughout, and a custom-made kitchen with a high-end designer backsplash and

Chris Gawrys,Gowest Realty Ltd.
Listed by: Chris Gawrys ,Gowest Realty Ltd. (416) 706-1425
House for sale: 302 WILLIAM STREET, Oakville

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$2,899,000

302 William Street, Oakville (1013 - OO Old Oakville), Ontario L6J 1E4

5 beds
3 baths
21 days

Cross Streets: Trafalgar & William. ** Directions: Trafalgar/E on William. Welcome to 302 William Street, a distinguished Heritage home in the heart of Old Oakville. This timeless red-brick residence exudes character and charm, set amidst beautifully landscaped gardens and mature trees. Meticulously

House for sale: 15 CHARTWELL ROAD, Oakville

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$11,750,000

15 Chartwell Road, Oakville (1013 - OO Old Oakville), Ontario L6J 3Z3

5 beds
6 baths
4 days

Cross Streets: Lakeshore Road E to S on Chartwell Road. ** Directions: Lakeshore Road E, South on Chartwell Road. 15 Chartwell Rd offers a lifestyle of unparalleled luxury. Drive through the gates & discover the grandeur of this palatial estate. South of Lakeshore,1 door from the lake on a

House for sale: 184 CHARTWELL ROAD, Oakville

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$5,699,000

184 Chartwell Road, Oakville (1013 - OO Old Oakville), Ontario L6J 3Z8

5 beds
7 baths
4 days

Chartwell Rd & Lakeshore Road East Welcome to 184 Chartwell Road, a distinguished residence offering over 7,800 sq. ft. of living space on a rare 100 x 238 ft premium lot (RL-1 zoning) in one of Oakville's most sought-after neighbourhoods. With 5 bedrooms, 4 bathrooms, and over 23,000 sq. ft.

House for sale: 366 GALT AVENUE, Oakville

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$3,888,000

366 Galt Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 3P3

5 beds
5 baths
130 days

Lakeshore | Allan | Galt 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,

Luciano Commisso,Harvey Kalles Real Estate Ltd.
Listed by: Luciano Commisso ,Harvey Kalles Real Estate Ltd. (416) 258-8536
House for sale: 494 CHARTWELL ROAD, Oakville

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$2,199,000

494 Chartwell Road, Oakville (1013 - OO Old Oakville), Ontario L6J 4A5

6 beds
3 baths
4 days

Chartwell Rd & Cornwall Rd Gorgeous Family Home on Prestigious Chartwell Road in Old OakvilleNestled on a prime 0.29-acre west-facing lot backing onto serene woodlands, this immaculate 4+2 bedroom residence is situated on the coveted "Street of Dreams" Chartwell Road in the heart of highly

Peter He,Re/max Hallmark Alliance Realty
Listed by: Peter He ,Re/max Hallmark Alliance Realty (905) 257-7500
House for sale: 1123 LAKESHORE ROAD E, Oakville

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$2,699,000

1123 Lakeshore Road E, Oakville (1013 - OO Old Oakville), Ontario L6J 1K9

5 beds
3 baths
164 days

Cross Streets: Lakeshore E & Burgundy Dr. ** Directions: Lakeshore Rd E to Burgundy Dr. Welcome to 1123 Lakeshore Road, located in one of Oakville's most sought-after neighbourhoods. This Home is bright, sun-filled and nestled on a rare and expansive 100 x 150 ft lot, Surrounded by mature trees

Listed by: Lou Piccioni ,Keller Williams Portfolio Realty (416) 864-3888
House for sale: 68 THOMAS STREET, Oakville

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$3,495,000

68 Thomas Street, Oakville (1013 - OO Old Oakville), Ontario L6J 3A4

4 beds
3 baths
30 days

Robinson St/Thomas St Welcome to 68 Thomas Street! This stunning heritage home (Georgian Revival circa 1835) offers the charm of yesteryear with today's modern amenities including a shaker-style kitchen with stainless steel appliances & countertop open to a bright, spacious breakfast area overlooking

House for sale: 200 CHARTWELL ROAD, Oakville

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$6,299,000

200 Chartwell Road, Oakville (1013 - OO Old Oakville), Ontario L6J 3Z8

5 beds
7 baths
18 days

Cross Streets: Lakeshore Road E & Chartwell. ** Directions: Lakeshore Rd East&Chartwell Rd. Nestled behind private gates on one of Oakville's most coveted "Street of Dreams," this exceptional estate sits on a spectacular 100 x 225 ft lot and offers over 7,500 sq ft of luxurious finished living

Peter He,Re/max Hallmark Alliance Realty
Listed by: Peter He ,Re/max Hallmark Alliance Realty (905) 257-7500
House for sale: 417 UNION STREET, Oakville

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$4,998,800

417 Union Street, Oakville (1013 - OO Old Oakville), Ontario L6J 1E7

6 beds
8 baths
74 days

Cross Streets: Lakeshore Rd E & Trafalgar Rd. ** Directions: If heading eastbound on Lakeshore Rd E, turn right onto First St, left on Union St, the property will be on your left side. If heading westbound on Lakeshore Rd E, turn left on Second St, right on Union St, the property will be on

Sam Allan Mcdadi,Sam Mcdadi Real Estate Inc.
Listed by: Sam Allan Mcdadi ,Sam Mcdadi Real Estate Inc. (905) 502-1500
House for sale: 247 DOUGLAS AVENUE, Oakville

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$3,850,000

247 Douglas Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 3S2

4 beds
3 baths
55 days

Cross Streets: Sheddon Ave and Douglas Ave. ** Directions: Lakeshore Rd E to Douglas Ave. 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

House for sale: 317 GLOUCESTER AVENUE, Oakville

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$5,700,000

317 Gloucester Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 3W8

5 beds
4 baths
48 days

Lakeshore Rd E to Gloucester 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

Listed by: Amelia Francis ,Re/max Aboutowne Realty Corp., Brokerage (905) 842-7000
House for sale: 322 PINE AVENUE, Oakville

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$1,799,900

322 Pine Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 2J9

4 beds
4 baths
110 days

Cross Streets: Trafalgar/Cornwall Road/Allan Street, Pine Avenue. ** Directions: Allan Street to Pine Avenue. 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

Carol Mcmonagle,Realty Executives Plus Ltd., Brokerage
Listed by: Carol Mcmonagle ,Realty Executives Plus Ltd., Brokerage (905) 337-7001
House for sale: 116 CHARTWELL ROAD, Oakville

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$7,995,000

116 Chartwell Road, Oakville (1013 - OO Old Oakville), Ontario L6J 3Z6

4 beds
6 baths
110 days

Lakeshore Rd E to Chartwell Rd Welcome to 116 Chartwell Road, one of Southeast Oakville's architecturally significant and environmentally advanced residences. Built to Net-Zero specifications, this home is a masterclass in modern sustainability, where wellness, technology and design exist in

Nina Mandeville,Sotheby's International Realty Canada, Brokerage
Listed by: Nina Mandeville ,Sotheby's International Realty Canada, Brokerage (905) 845-0024
House for sale: 435 MAPLE AVENUE, Oakville

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$2,850,000

435 Maple Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 2J2

5 beds
4 baths
30 days

Cross Streets: Watson/ Maple. ** Directions: Watson and Maple Ave. 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

Linda Huang,Right At Home Realty
Listed by: Linda Huang ,Right At Home Realty (647) 970-5616
House for sale: 295 MAPLE AVENUE, Oakville

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$2,998,000

295 Maple Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 3M5

5 beds
4 baths
139 days

Cross Streets: Maple Avenue at Reynolds Street. ** Directions: Reynolds Street south to Maple Avenue. Fabulous custom build in prime Old Oakville steps to Whole Foods market, Oakville GO and coveted southeast Oakville schools. Luxury living with high ceilings throughout over 3000 SF plus fully

House for sale: 298 DOUGLAS AVENUE, Oakville

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$2,749,000

298 Douglas Avenue, Oakville (1013 - OO Old Oakville), Ontario L4J 3S4

5 beds
3 baths
6 days

Cross Streets: Lakeshore Rd East & Trafalgar Rd. ** Directions: Northwest onto Douglas Ave from Lakeshore Rd East. Nestled Just Moments From The Shores Of Lake Ontario In One Of Oakville's Most Coveted Neighbourhoods, 298 Douglas Avenue Offers The Perfect Blend Of Lakeside Living And Refined

Daniel Fisherman,North 2 South Realty
Listed by: Daniel Fisherman ,North 2 South Realty (416) 697-1400
House for sale: 350 KING STREET, Oakville

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$12,900,000

350 King Street, Oakville (1013 - OO Old Oakville), Ontario L6J 1C2

5 beds
5 baths
21 days

Cross Streets: Allan and Lakeshore. ** Directions: From Lakeshore Rd E go south on Allan. Nestled in the heart of downtown Oakville, this magnificent historical home offers unparalleled charm and elegance, combined with modern amenities. Spanning over 8,000 square feet, the expansive layout

Listed by: Lise Lafreniere ,Re/max Aboutowne Realty Corp., Brokerage (905) 842-7000
House for sale: 200 WILLIAM STREET, Oakville

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$3,250,000

200 William Street, Oakville (1013 - OO Old Oakville), Ontario L6J 1C7

5 beds
3 baths
138 days

Trafalgar Road South; William Street West Well positioned property in historic Old Oakville, south of Lakeshore, just steps to the beach, Oakville harbour\r\nand Town Square. Sitting proudly up on a rise, this 2 1/2 storey home features wonderful views, light and\r\nplenty of space to create

House for sale: 287 MACDONALD ROAD, Oakville

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$4,290,000

287 Macdonald Road, Oakville (1013 - OO Old Oakville), Ontario L6J 2A6

4 beds
5 baths
6 days

Cross Streets: Trafalgar Road and MacDonald Road. ** Directions: Trafalgar Road to MacDonald Road. This completely renovated contemporary residence represents the pinnacle of modern design and sophisticated living in one of Oakville's most desirable locations of Old Oakville.Every detail of

House for sale: 287 MACDONALD Road, Oakville

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$4,290,000

287 Macdonald Road, Oakville, Ontario L6J 2A6

4 beds
4 baths
6 days

Trafalgar Road to MacDonald Road This completely renovated contemporary residence represents the pinnacle of modern design and sophisticated living in one of Oakville's most desirable locations of Old Oakville. Every detail of this 4 Bedroom | 4+1 Bathrooms | 4,819 Sq Ft Finished Living Space

House for sale: 247 DOUGLAS Avenue, Oakville

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$3,850,000

247 Douglas Avenue, Oakville, Ontario L6J 3S2

4 beds
3 baths
58 days

Lakeshore Road E to Douglas Ave 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

House for sale: 428 SHEDDON Avenue, Oakville

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$3,350,000

428 Sheddon Avenue, Oakville, Ontario L6J 1Y3

5 beds
4 baths
3 days

One of the best locations in old Oakville! This exceptional custom home on a quiet side street features a bright freshly painted interior with 10' main floor ceilings, crown mouldings, 3 gas fireplaces, a Control4 full house hard wired entertainment system, elevator rough-in, and site-finished

Paul Strome,Chestnut Park Realty Southwestern Ontario Ltd., Brokerage
Listed by: Paul Strome ,Chestnut Park Realty Southwestern Ontario Ltd., Brokerage (289) 952-9760
House for sale: 46 SECOND Street, Oakville

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$8,479,000

46 Second Street, Oakville, Ontario L6J 3T2

5 beds
7 baths
45 days

Lakeshore Road E to Second St Discover an extraordinary custom built residence in prestigious Old Oakville, where architectural excellence meets modern luxury just steps from the lake.This 2024 Net Zero Ready masterpiece represents a distinguished collaboration between renowned industry leaders

House for sale: 150 CAIRNCROFT ROAD, Oakville

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$2,900,000

150 Cairncroft Road, Oakville (1011 - MO Morrison), Ontario L6J 4L9

4 beds
3 baths
12 days

Lakeshore Rd E & Cairncroft Rd Welcome to 150 Cairncroft, a rare opportunity to own a distinctive property in one of Oakville's most coveted neighbourhoods. Nestled on a stunning 0.4 acre (17,416 sq ft) corner lot, this charming 3,052 sq ft residence is enveloped by mature trees and lush landscaping,

Matthew Prior,Royal Lepage Real Estate Services Ltd.
Listed by: Matthew Prior ,Royal Lepage Real Estate Services Ltd. (905) 845-4267
House for sale: 169 MORRISON ROAD, Oakville

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$2,650,000

169 Morrison Road, Oakville (1011 - MO Morrison), Ontario L6J 4J3

5 beds
3 baths
85 days

Cross Streets: Lakeshore/Morrison. ** Directions: north of Lakeshore Rd E. This private, quiet, lush 101 x 149ft lot is simply spectacular with it's beautifully manicured and maintained gardens. Spend every warm moment relaxing around the pool and taking in nature with the Morrison Creek just

Carmen Krasevac,Royal Lepage Real Estate Services Ltd.
Listed by: Carmen Krasevac ,Royal Lepage Real Estate Services Ltd. (416) 272-5191
House for sale: 1368 TANSLEY DRIVE, Oakville

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$1,625,000

1368 Tansley Drive, Oakville (1020 - WO West), Ontario L6L 2N4

4 beds
2 baths
12 days

St Rebecca St and Sherin Dr Prestigious South West Oakville Bungalow - Live, Lease, Or Build. Discover Refined Living In This Beautifully Maintained Four-Bedroom Bungalow, Gracefully Situated In One Of South West Oakville's Most Distinguished And Established Neighbourhoods. Surrounded By Mature

Listed by: Lauren Allisia Parente ,Re/max Premier Inc. (416) 987-8000
House for sale: 2305 CHEVERIE STREET, Oakville

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$2,750,000

2305 Cheverie Street, Oakville (1006 - FD Ford), Ontario L6J 6C5

5 beds
4 baths
12 days

Cross Streets: -. ** Directions: Lakeshore Rd E / Devon Rd. This stately Georgian home is the epitome of luxury living. Located in one of the finest neighbourhoods of South-East Oakville & in the coveted Oakville Trafalgar school district. Surrounded by mature trees & lush greenery in a ravine-like

House for sale: 2163 VINELAND CRESCENT, Oakville

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$2,550,000

2163 Vineland Crescent, Oakville (1015 - RO River Oaks), Ontario L6H 0J6

6 beds
5 baths
3 days

River Oaks Blvd E & Namron Gate Experience refined elegance in this stunning family home built by Biddington Homes, offering 5,001 sq. ft. of exquisitely finished living space across 3 levels. Nestled in the vibrant family friendly community of River Oaks in Oakville, this 6-bedroom (4+2),

House for sale: 3102 MILLICENT AVENUE, Oakville

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$1,890,000

3102 Millicent Avenue, Oakville (1008 - GO Glenorchy), Ontario L6H 0V2

4 beds
4 baths
12 days

Wheat Boom and Sixth Line Unique Home with Superb Open Concept Floor Plan. Bright & Spac , with Large welcoming Foyer.,4-beds, 4 bath with double garage in a desirable Fernbrook's Seven Oaks community features3,031 sqft plus an unfinished lower level, 10ft & 9ft ceilings & hardwood throughout.

Frank Leo,Re/max West Realty Inc.
Listed by: Frank Leo ,Re/max West Realty Inc. (416) 917-5466
House for sale: 3260 RIBBLE CRESCENT, Oakville

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$2,240,000

3260 Ribble Crescent, Oakville (1000 - BC Bronte Creek), Ontario L6M 0B1

4 beds
5 baths
4 days

Cross Streets: Bronte/Uppermiddle. ** Directions: Colonel William/ Richview. Executive Luxury in the Heart of Bronte Creek ! Experience the pinnacle of family living in this sophisticated 4+1-bedroom, 5-bathroom detached residence, perfectly situated on a quiet, executive crescent in Oakville's

House for sale: 350 WEIGHTON DRIVE, Oakville

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$2,668,000

350 Weighton Drive, Oakville (1020 - WO West), Ontario L6K 2R4

5 beds
5 baths
40 days

Cross Streets: Morden Rd and Weighton Dr. ** Directions: Pinegrove/Morden/Speers/Dorval. Priced To Sell. This breathtaking custom built residence nestled on a quiet interior street in sought after South Oakville. Offering over 3,300 sq ft of luxurious above grade living space plus a fully finished

Listed by: Leanne Binsell ,Re/max Hallmark Alliance Realty (905) 257-7500
House for sale: 1223 BLACK BEAR TRAIL, Oakville

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$1,718,990

1223 Black Bear Trail, Oakville (1010 - JM Joshua Meadows), Ontario L6H 8B1

5 beds
4 baths
10 days

Cross Streets: Dundas St E West of Trafalgar Rd. ** Directions: Dundas St. E to John McKay Blvd. RH turn on Pelican Pass LH turn on Wolverine Path. RH turn on Black Bear Trail. Welcome to 1223 Black Bear Trail, a brand-new, never-lived-in home by Mattamy Homes in the sought-after Joshua Meadows

Rosemarie V. Wallace,Sutton Group Quantum Realty Inc.
Listed by: Rosemarie V. Wallace ,Sutton Group Quantum Realty Inc. (905) 822-5000
House for sale: 2454 LONGRIDGE CRESCENT, Oakville

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$1,795,000

2454 Longridge Crescent, Oakville (1015 - RO River Oaks), Ontario L6H 6N8

4 beds
4 baths
11 days

Heath and Longridge Exquisitely designed with a true model-home feel, this four-bedroom River Oaks home showcases elevated finishes and stunning upgrades that extend from its refined interior to the beautifully designed backyard retreat. A grand double-door entrance opens to an impressive foyer

House for sale: 1346 CHALFIELD DRIVE, Oakville

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$1,699,000

1346 Chalfield Drive, Oakville (1004 - CV Clearview), Ontario L6J 6R5

4 beds
4 baths
10 days

Cross Streets: Kingsway/Ford. ** Directions: The Kingsway to Chalfield. Meticulously maintained and updated 3062 square foot detach with professionally finished basement (2024)having a separate side entrance to basement on a 59' foot lot! Main floor features bamboo hardwood and Porcelain flooring

Stacey Robinson,Royal Lepage Realty Plus Oakville
Listed by: Stacey Robinson ,Royal Lepage Realty Plus Oakville (905) 464-7653
House for sale: 2382 FALKLAND CRESCENT, Oakville

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$1,425,000

2382 Falkland Crescent, Oakville (1022 - WT West Oak Trails), Ontario L6M 4Y1

6 beds
4 baths
9 days

Cross Streets: PROUDFOOT & ASTRA. ** Directions: Dundas Street & Proudfoot. BEAUTIFUL 4 BEDROOM open-concept floor plan on child safe Crescent in demand WESTOAK TRAILS! Short distance to Oakville hospital. Gleaming DARK Walnut hardwood in Living/Dining Rm Combination & Family Room, Vaulted

Listed by: Hesham El Shaboury ,International Realty Firm, Inc. (647) 313-3400
House for sale: 3109 LARRY CRESCENT, Oakville

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$1,799,000

3109 Larry Crescent, Oakville (1008 - GO Glenorchy), Ontario L6M 0S8

4 beds
5 baths
10 days

Sixth Line. and Sixteen Mile Dr. Welcome to this beautifully maintained Rosehaven-built home in the highly sought-after Preserve community, offering over 2,800 sq.ft of thoughtfully designed above ground living and finished basement space. This carpet-free home features an open-concept layout,

House for sale: 1324 BIRCHCLIFF DRIVE, Oakville

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$2,099,000

1324 Birchcliff Drive, Oakville (1007 - GA Glen Abbey), Ontario L6M 2A4

5 beds
4 baths
11 days

Nottinghill Gate and Birchcliff Drive This Stunning 4+1 bedroom, 4-bath home is located in Oakville's highly sought-after Glen Abbey community. Bright, airy interiors are filled with natural light, highlighting wide-plank hardwood flooring, graceful staircases, natural gas fireplace and an

Rayo Irani,Re/max Aboutowne Realty Corp.
Listed by: Rayo Irani ,Re/max Aboutowne Realty Corp. (647) 802-2020
House for sale: 21 ENNISCLARE DRIVE E, Oakville

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$15,500,000

21 Ennisclare Drive E, Oakville (1011 - MO Morrison), Ontario L6J 4N3

5 beds
7 baths
81 days

Lakeshore Rd./Ennisclare Dr. Magnificent Waterfront Property On Massive 1.15 Acre Riparian Lakefront Lot Fulfills All Dreams You Ever Have. Experience Lifetime Spectacular Waterview On Breathtaking Sunrising Moments. Lakeside Entertainment Amenities Can Be All Accompanied By The Outdoor Pool

Gary Zhu,Canada Home Group Realty Inc.
Listed by: Gary Zhu ,Canada Home Group Realty Inc. (905) 337-9888
House for sale: 140 CHERRYHURST ROAD, Oakville

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$1,500,000

140 Cherryhurst Road, Oakville (1008 - GO Glenorchy), Ontario L6M 0W1

4 beds
4 baths
38 days

Neyagawa/Dundas Gorgeous 3+1 bedroom, 4 bathroom home in the highly desired Oakville's Preserve community. Featuring an open-concept layout, this home boasts premium upgrades throughout, The kitchen is a chef's delight with granite countertops, an oversized island, and stainless steel appliances,

Listed by: Shaz Nasir ,Century 21 Regal Realty Inc. (416) 849-5360
House for sale: 134 ABBEY Court, Oakville

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$2,980,000

134 Abbey Court, Oakville, Ontario L6J 4L1

5 beds
4 baths
35 days

Lakeshore Rd E & Cairncroft Rd Exquisitely renovated from top to bottom, this exceptional 4+1 bedroom family residence is set in the magnificent enclave of Morrison, one of Southeast Oakville’s most prestigious enclaves on a rare 103 x 150 ft premium lot just steps from Lake Ontario,

Brad Miller,Century 21 Miller Real Estate Ltd.
Listed by: Brad Miller ,Century 21 Miller Real Estate Ltd. (905) 338-2121
House for sale: 141 DIGBY ROAD, Oakville

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$2,099,888

141 Digby Road, Oakville (1006 - FD Ford), Ontario L6J 6B7

5 beds
3 baths
7 days

Cross Streets: Lakeshore Rd E & Ford Dr. ** Directions: Lakeshore Rd E to Devon Rd to Canso Rd to Digby Rd. Nestled on a picturesque tree-lined street in highly sought-after South Oakville, this beautifully updated 4-bedroom family home offers exceptional convenience just minutes to the QEW,

Brett Fraser Smiley,Royal Lepage Real Estate Services Ltd.
Listed by: Brett Fraser Smiley ,Royal Lepage Real Estate Services Ltd. (416) 809-9169
House for sale: 118 WESTCHESTER ROAD, Oakville

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$1,849,000

118 Westchester Road, Oakville (1015 - RO River Oaks), Ontario L6H 6H9

5 beds
4 baths
6 days

River Glen&Castle Hill Cres A Rare Carriage-Style Gem in OakvilleThis distinguished carriage-style home features a rear-entry garage that delivers a beautifully uninterrupted façade - an elegant and rare departure from the typical suburban streetscape that sets this home apart from the very

Listed by: Marilyn Duarte ,Sutton Group Quantum Realty Inc. (905) 844-5000
House for sale: 2055 LAKESHORE ROAD E, Oakville

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$5,450,000

2055 Lakeshore Road E, Oakville (1006 - FD Ford), Ontario L6J 1M4

4 beds
3 baths
38 days

Lakeshore Road W, E of Maple Grove Dr. Private Lane on North Side. Nestled at the end of a private laneway on .996 acre in sought-after South East Oakville, tranquility awaits. This Arts and Crafts-style home, boasting a wrap-around veranda, sits amidst nearly an acre of meticulously manicured

House for sale: 427 CAIRNCROFT ROAD, Oakville

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$2,850,000

427 Cairncroft Road, Oakville (1011 - MO Morrison), Ontario L6V 4N1

4 beds
4 baths
4 days

Cross Streets: Cairncroft/Lakeshore. ** Directions: ANN MEREDITH. Nestled in the heart of Morrison, this distinguished Southeast Oakville residence offers a rare blend of privacy, elegance, and family functionality. Set on a premium 81 x 140 ft lot backing onto King's Forest, the home is framed

Listed by: Sofia Wu ,Homelife Landmark Realty Inc. (905) 305-1600
House for sale: 408 LAKESHORE ROAD W, Oakville

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$4,500,000

408 Lakeshore Road W, Oakville (1017 - SW Southwest), Ontario L6K 1G1

6 beds
8 baths
72 days

Cross Streets: Lakeshore Rd W / Dorval. ** Directions: Lakeshore Rd W / Lambert Common. This is a remarkable vacant lot that includes drawings and building permit. House pictures are renderings and details are from the drawings. Embark on a life of uncompromised luxury with this architectural

House for sale: 36 ANDERSON STREET, Oakville

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$4,090,000

36 Anderson Street, Oakville (1002 - CO Central), Ontario L6K 1A5

4 beds
4 baths
150 days

Lakeshore/Chisholm Incredible offering in the Harbour district of Old Oakville one block from the lake and harbour and a short stroll to beautiful downtown Oakville. Over 3350SF of luxury living space. Beautiful custom build with open concept floor plan featuring soaring 10' ceilings and filled

Buying a 4 bedroom house in Oakville: what smart Ontario buyers and investors should know

A 4 bedroom house Oakville search often starts with lifestyle (schools, parks, lakefront) and ends with practical constraints (zoning, transit, and resale). Oakville's detached market is shaped by limited supply, strong school catchments, and commuter convenience to the QEW/403/407 and GO Transit. Below is pragmatic, Ontario-specific guidance to help you evaluate a 4 bedroom house for sale in Oakville, Ontario—whether you're upsizing, planning multi-generational living, or evaluating rental potential.

Neighbourhood fit and lifestyle value

Oakville is a collection of distinct micro-markets. Old Oakville and Kerr Village offer walkable, character streetscapes near the lake; Glen Abbey and Westoak Trails lean suburban with trails and golf; River Oaks and Uptown Core skew newer with convenient retail; Joshua Creek and Iroquois Ridge are popular for top-ranked schools; Bronte has a coastal feel with marina access. The “right” 4 bedroom house for sale will be influenced by school boundaries (Halton District and Halton Catholic boards), commute patterns (proximity to Oakville GO or Bronte GO), and amenities like arenas and community centres.

Detached 4 bedroom houses for sale in Oakville Canada typically provide 2,200–3,500 sq. ft., attached garages, and finished basements. Newer builds (2000s+) often feature open-concept layouts and larger ensuites; 1980s–1990s homes may have more compartmentalized plans but sit on wider lots. If you are weighing options beyond Oakville, comparing to a 4-bedroom house in St. Catharines can be a useful affordability benchmark while maintaining GO connectivity via Niagara services.

Zoning, secondary suites, and intensification rules

Ontario's More Homes Built Faster Act (Bill 23) enables up to three residential units on many urban lots (primary plus up to two additional residential units), subject to municipal rules. Oakville has been updating its zoning by-laws to align, but implementation details vary by zone (R1–R4 and site-specific exceptions). Before buying with plans for a basement apartment or garden suite, verify:

  • Whether additional units are permitted in the specific zone and if parking standards can be met.
  • Building Code/fire separation, egress windows, and ceiling height requirements for second suites.
  • Site constraints such as lot coverage, floor area ratio, and setbacks that may limit expansions.

Homes near creeks or ravines may fall under Conservation Halton regulation—setbacks and permitting can affect additions and walkouts. Oakville's Tree Protection and private tree removal by-law also impact renovation timelines. If you're exploring multi-generational configurations (for example, two primary bedrooms), you may find inspiration in properties like two-primary-suite homes in Brampton, then apply the concept under Oakville's rules.

Resale fundamentals: the elements that protect value

Resale strength in Oakville is tied to stable, family-friendly demand. For a 4 bedroom house for sale in Oakville Ontario, prioritize:

  • School catchment and walkability: Proximity to sought-after schools and parks typically anchors pricing.
  • Transit and highway access: Easy reach to GO stations and the QEW/403/407 corridors broadens buyer appeal.
  • Lot quality: Wider frontages and private backyards outperform on resale; pie-shaped lots can be a pleasant surprise.
  • Functional layout: A main-floor office, upper-level laundry, and a true principal suite are now baseline expectations.
  • Neutral updates: Kitchens and baths done within the last 10–12 years support appraisal and marketability.

If future upsizing is on your horizon, studying larger urban homes—such as a 5-bedroom family home in Toronto or a six-bedroom Toronto house—can help calibrate longer-term budget and design targets even while you secure a 4 bedroom house today.

Market timing and seasonal patterns

In the GTA and Halton Region, inventory and buyer activity trend higher in spring (March–May) and early fall (September–October). July/August often softens due to vacations, and late December to mid-January is typically quiet. In tight-supply pockets of Oakville, prime listings can attract multiple offers regardless of season, but a well-prepared buyer in a slower month may still negotiate favourable terms. Interest rate decisions also create mini-cycles; pre-approvals with a rate hold can help you act decisively when a suitable 4 bedroom house for sale appears.

Investment lens: rents, short-term rules, and unit strategy

Oakville's rental demand is driven by corporate relocations, families seeking school access, and medical/tech professionals. Investors often target a secondary suite to improve cash flow. That said, short-term rental bylaws are restrictive in many Ontario municipalities. Oakville maintains licensing and zoning rules that can limit or prohibit short-term rentals outside of a principal residence context. Confirm current Town of Oakville regulations, licensing requirements, and condominium declarations (if applicable) before assuming any short-term or medium-term rental strategy.

When evaluating returns, use conservative rent estimates, include realistic maintenance and insurance, and stress-test for vacancy. If you're considering very large, lodging-style assets (e.g., a “13 bedroom house”), note that such configurations are rare in Oakville and will raise zoning and building code questions. For perspective on scale, compare to a 10-bedroom Toronto property; even there, compliance and licensing drive viability more than bedroom count.

Condition, energy, and risk checks that matter

Older Oakville homes (pre-2000) may need roof, window, HVAC, and plumbing updates. Newer homes can still present grading or moisture issues. Key due diligence items:

  • Moisture management: Foundation cracks, window wells, and sump systems should be assessed—especially near ravine corridors.
  • Electrical capacity: 200-amp panels better support EV chargers and heat pumps.
  • Insurance factors: Overland flood endorsements are advisable where creek adjacency exists; confirm sewer backflow protection.
  • Energy upgrades: Greener Homes grants have evolved; low-interest loans and utility rebates may still be available—verify current programs.

For lifestyle features, pools remain a personal-value item: they help attract certain buyers but narrow the pool (no pun intended) for others. Studying a Toronto five-bedroom with a pool can help you gauge maintenance considerations and resale trade-offs before you add one in Oakville.

Financing and ownership planning

For a 4 bedroom house, most buyers will fall under uninsured mortgages if the purchase price exceeds $1M (no CMHC insurance). That raises down payment (minimum 20%) and stress-test importance. Investors should clarify lender treatment of rental income—some lenders use add-back; others use offset. If you are exploring co-ownership with parents or adult children, define equity splits and exit rights up front. Multi-generational households sometimes prefer layouts with two suites or dual primaries; reviewing layouts like those in 2-bedroom Toronto starter homes or 3-bedroom “all-inclusive” Ontario rentals offers context for future rental or in-law conversion potential.

How Oakville compares across the GTA and beyond

Oakville's price premium reflects schools, lake amenities, and planning stability. Buyers sometimes expand their search to communities with different value equations. For compact urban living, see 1-bedroom options in Dundas. For family upsizing in the core, large-city comparisons include five-bedroom houses in Toronto and specialty inventory like six-bedroom homes. Investors thinking nationally sometimes benchmark against markets such as the Lower Mainland via a 5-bedroom house in Surrey. These comparisons won't replace Oakville-specific analysis, but they help calibrate price-to-utility ratios and long-term plans.

Short-term vs. long-term use: principal residence, rental, or hybrid

Given Oakville's bylaws and family-centric demand, the strongest cases are principal residence or long-term rental with a licensed secondary suite (where permitted). Be cautious with short-term stays; most municipalities in the GTA either restrict them to principal residences or impose licensing that materially changes returns. Hybrid strategies—living in the main and renting a legal suite—can offer a balanced approach. If you anticipate growth beyond four bedrooms, understanding the jump to larger footprints is instructive; Toronto even sees niche inventory such as 10-bedroom houses, but those are specialized assets, not typical comparables for Oakville.

Seasonal use and cottage considerations for Oakville buyers

Many Oakville families also consider a seasonal property. If you're balancing a 4 bedroom house for sale in Oakville with a cottage, budget for rural-specific due diligence: septic inspection with flow test, water potability (well or lake intake), shoreline allowances, and seasonal road access. Lenders may apply different down payment and amortization rules on recreational properties. Insurance can also differ (wood heat, distance to hydrants). Your urban primary residence may remain the financing anchor while the cottage takes a higher down payment. This is a case where working with a brokerage that tracks both urban and recreational markets helps; resources like KeyHomes.ca let you research neighbourhood data, compare 4 bedroom houses for sale, and connect with licensed Ontario professionals familiar with both halves of the plan.

Pricing discipline and offer strategy

Oakville often mixes “offer nights” with list-low/market-high tactics and conventional list-at-market pricing. Ask your advisor for a block-by-block comparative market analysis that adjusts for lot width, finished square footage above grade, and renovation recency. If the home is staged and fresh to market in a coveted school zone, assume competition; if it's been on for 21+ days, investigate condition or pricing misalignment and negotiate accordingly. When inventory is thin, having a “Plan B” neighbourhood or being open to a three-bedroom plus loft can unlock value.

Practical takeaways for a 4 bedroom house Oakville search

  • Confirm zoning early: If you want a legal suite or addition, validate the zoning and any Conservation Halton constraints before waiving conditions.
  • Buy the lot and layout: Cosmetic updates are manageable; lot shape, exposure, and traffic patterns are not.
  • Insulate the budget: Include 1–2% of the purchase price annually for preventative maintenance, higher if the roof/HVAC/windows are mid-life.
  • Align with seasonality: Spring brings selection; late summer and winter may bring negotiation.
  • Document quality: Keep permits and invoices for future resale; buyers pay a premium for properly documented work.

For broader context, it can be helpful to examine specialized or adjacent inventory. Some families weigh a move to a larger metro property with amenities such as pools, comparing to a GTA home with a pool, while others explore niche urban stock—rare even in big cities—like multi-suite or very large homes. You'll also find occasional hybrid references like all-inclusive three-bedroom rentals in Ontario when considering interim housing during renovations. Platforms like KeyHomes.ca are useful for exploring these comparables alongside your primary goal: a well-located 4 bedroom house for sale in Oakville, Ontario that aligns with your family's plans today and your resale expectations tomorrow.