4-Bedroom House in Oakville

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House for sale: 25 HOWARD AVENUE, Oakville

28 photos

$3,100,000

25 Howard Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 3Y2

5 beds
2 baths
48 days

Cross Streets: Lakeshore Ave E/Howard Ave. ** Directions: Lakeshore Rd to Howard Ave. Rare opportunity in coveted Orchard Beach, just steps from Lake Ontario and the waterfront trail. Set on a premium 50 x 160 ft lot, this property comes with completed architectural and engineering drawings

Iryna Tarabanovska,Cirealty
Listed by: Iryna Tarabanovska ,Cirealty (888) 247-8808
House for sale: 417 UNION STREET, Oakville

50 photos

$4,750,000

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

6 beds
8 baths
25 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: 338 MACDONALD ROAD, Oakville

16 photos

$3,790,000

338 Macdonald Road, Oakville (1013 - OO Old Oakville), Ontario L6J 2B7

4 beds
4 baths
16 days

MacDonald Rd/Allan St Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. A selection

House for sale: 46 SECOND STREET, Oakville

48 photos

$7,979,000

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

5 beds
7 baths
25 days

Cross Streets: Lakeshore Road E & Second St. ** Directions: Lakeshore Road E to Second St. Walk to downtown Oakville from this 2024 custom-built residence, third house from Lake Ontario on a 65 x 158 lot south of Lakeshore. A rare new-construction opportunity in Old Oakville's most walkable

House for sale: 322 PINE AVENUE, Oakville

47 photos

$1,699,900

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

4 beds
4 baths
47 days

Cross Streets: Trafalgar/Cornwall. ** Directions: Allan Street to Pine Avenue. IMPROVED OPPORTUNITY! Discover this charming family home nestled in the heart of Old Oakville, one of the area's most desirable neighbourhoods. Meticulously maintained 1.5-storey residence on a beautifully landscaped

Carol Mcmonagle,Realty Executives Plus Ltd., Brokerage
Listed by: Carol Mcmonagle ,Realty Executives Plus Ltd., Brokerage (905) 337-7001
House for sale: 467 CAESAR AVENUE, Oakville

26 photos

$2,299,000

467 Caesar Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 3Z1

4 beds
3 baths
25 days

Cornwall Rd/Chartwell Rd Absolutely stunning and totally upgraded four bedroom family home in prime South East Oakville location! Very desirable street on a quiet cul-de-sac close to top public and private schools. The spacious primary suite is privately set on the upper level and features

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
228 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: 15 CHARTWELL ROAD, Oakville

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$10,800,000

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

5 beds
6 baths
38 days

Cross Streets: -. ** Directions: Lakeshore Road E to S 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 HALF ACRE LOT. Painstakingly curated, the

House for sale: 317 GLOUCESTER AVENUE, Oakville

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$4,980,000

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

5 beds
4 baths
9 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: 155 GLOUCESTER AVENUE, Oakville

44 photos

$10,750,000

155 Gloucester Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 3W3

5 beds
8 baths
5 days

Lakeshore Road E/Gloucester Ave Set on one of the most coveted streets in Old Oakville, this extraordinary residence offers a rare combination of landmark architecture, timeless design, and resort-inspired living on an irreplaceable 0.6-acre property. Originally designed by renowned architect

House for sale: 74 HOWARD AVENUE, Oakville

23 photos

$5,500,000

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

5 beds
4 baths
45 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: 184 KING STREET, Oakville

50 photos

$4,299,000

184 King Street, Oakville (1013 - OO Old Oakville), Ontario L6J 1B4

4 beds
5 baths
16 days

Cross Streets: King & Thomas St. ** Directions: Lakeshore Rd E to Thomas to King. Set in the heart of Old Oakville on a generous, tree-lined lot, this distinguished red brick residence blends timeless architecture with thoughtful modern updates. Featuring 3+1 bedrooms and 5 bathrooms, each

House for sale: 276 SPRUCE STREET, Oakville

36 photos

$2,895,000

276 Spruce Street, Oakville (1013 - OO Old Oakville), Ontario L6J 2G7

5 beds
3 baths
12 days

Trafalgar & Spruce A complete renovation & restoration was undertaken to this circa 1890 home. Exceptional attention to detail created a functional layout enhanced by superb finishings. An inviting front covered porch draws you into this 4 + 1 bdrm, 3 bath home in the heart of Old Oakville.

Listed by: Julie Allison Rennie ,Chestnut Park Real Estate Limited (416) 925-9191
House for sale: LOT 101 DOUGLAS AVENUE, Oakville

17 photos

$4,290,000

Lot 101 Douglas Avenue, Oakville (1013 - OO Old Oakville), Ontario L6J 2B7

4 beds
4 baths
73 days

Palmer Ave/Douglas Ave Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. The Douglas

House for sale: 139 ALLAN STREET, Oakville

38 photos

$2,999,000

139 Allan Street, Oakville (1013 - OO Old Oakville), Ontario L6J 3N6

4 beds
3 baths
25 days

Cross Streets: Randall. ** Directions: South on Allan until Randall. Nestled in the Heart of Downtown Oakville, this renovated 3000+ sq ft home blends historical charm with modern luxury. Offering 4 bedrooms and 2.5 baths, this home has been extensively updated throughout by Stonewood Homes

Listed by: Brenda Seymour ,Right At Home Realty, Brokerage (905) 637-1700
House for sale: 494 CHARTWELL ROAD, Oakville

39 photos

$1,920,000

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

6 beds
3 baths
46 days

Cross Streets: Chartwell Rd & Cornwall Rd. ** Directions: Chartwell Rd & Linbrook 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

Peter He,Re/max Hallmark Realty Ltd.
Listed by: Peter He ,Re/max Hallmark Realty Ltd. (647) 739-2618
House for sale: 382 TRAFALGAR ROAD, Oakville

50 photos

$3,950,000

382 Trafalgar Road, Oakville (1013 - OO Old Oakville), Ontario L6J 3H5

4 beds
4 baths
48 days

Trafalgar Rd & Cornwall Rd Private, elevated, and unlike anything else in Old Oakville - A true four-season outdoor retreat, your private playground for the outdoor enthusiast-where each day invites skating, paddling, kayaking, hiking, fishing, boating and cross-country skiing, alongside wildlife

House for sale: 435 MAPLE AVENUE, Oakville

50 photos

$2,800,000

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

5 beds
4 baths
34 days

Cross Streets: Watson/ Maple. ** Directions: Watson/ 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 features

Linda Huang,Right At Home Realty
Listed by: Linda Huang ,Right At Home Realty (647) 970-5616
House for sale: 53 THOMAS STREET, Oakville

50 photos

$3,250,000

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

4 beds
3 baths
236 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: 298 DOUGLAS AVENUE, Oakville

45 photos

$2,499,000

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

5 beds
3 baths
2 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: 46 SECOND Street, Oakville

48 photos

$7,979,000

46 Second Street, Oakville, Ontario L6J 3T2

5 beds
7 baths
18 days

Lakeshore Road E to Second St Walk to downtown Oakville from this 2024 custom-built residence, third house from Lake Ontario on a 65 x 158 lot south of Lakeshore. A rare new-construction opportunity in Old Oakville's most walkable pocket: minutes walk to the harbour, the Oakville Club, Lakeshore

House for sale: 287 MACDONALD Road, Oakville

40 photos

$3,999,000

287 Macdonald Road, Oakville, Ontario L6J 2A6

4 beds
5 baths
60 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: 338 MACDONALD Road, Oakville

16 photos

$3,790,000

338 Macdonald Road, Oakville, Ontario L6J 2B7

4 beds
4 baths
68 days

MacDonald Rd/Allan St Nestled in an immensely desired mature pocket of Old Oakville, this exclusive development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. A selection of distinct

Brad Miller,Century 21 Miller Real Estate Ltd.
Listed by: Brad Miller ,Century 21 Miller Real Estate Ltd. (905) 338-2121
House for sale: LOT 101 DOUGLAS Avenue, Oakville

17 photos

$4,290,000

Lot 101 Douglas Avenue, Oakville, Ontario L6J 2B7

4 beds
4 baths
73 days

Palmer Ave/Douglas Ave Nestled in an immensely desired mature pocket of Old Oakville, this exclusive development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. The Douglas Collection

Brad Miller,Century 21 Miller Real Estate Ltd.
Listed by: Brad Miller ,Century 21 Miller Real Estate Ltd. (905) 338-2121
House for sale: 155 GLOUCESTER Avenue, Oakville

44 photos

$10,750,000

155 Gloucester Avenue, Oakville, Ontario L6J 3W3

5 beds
8 baths
5 days

Lakeshore Rd E, North on Gloucester Set on one of the most coveted streets in Old Oakville, this extraordinary residence offers a rare combination of landmark architecture, timeless design, and resort-inspired living on an irreplaceable 0.6-acre property. Originally designed by renowned architect

Brad Miller,Century 21 Miller Real Estate Ltd.
Listed by: Brad Miller ,Century 21 Miller Real Estate Ltd. (905) 338-2121
House for sale: 428 SHEDDON Avenue, Oakville

49 photos

$3,350,000

428 Sheddon Avenue, Oakville, Ontario L6J 1Y3

5 beds
4 baths
93 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: 2083 WILLHAVEN TRAIL, Oakville

42 photos

$1,659,900

2083 Willhaven Trail, Oakville (1019 - WM Westmount), Ontario L6M 5G3

4 beds
3 baths
12 days

Third Line / Pine Glen Rd. Stunning beautiful renovated Detached Home sits on a large premium pie shaped, pool sized lot in Oakville's sought Westmount Community. Featuring beautiful curb appeal with an interlock front porch and French curbs and double car garage with convenient access entry

Listed by: Wen Zheng ,Kingsway Real Estate (905) 277-2000
House for sale: 3305 MISTWELL Crescent, Oakville

48 photos

$2,388,000

3305 Mistwell Crescent, Oakville, Ontario L6L 0A3

4 beds
4 baths
14 days

Welcome to an exceptional blend of luxury, lifestyle and location in one of Oakville's most coveted lakeside communities. Situated in the exclusive Waterview Collection of Lakeshore Woods, this home enjoys larger than average lot dimensions, and is steps away from Lake Ontario, Cuyagua Beach

Nick Gewarges,Right At Home Realty
Listed by: Nick Gewarges ,Right At Home Realty (905) 330-7376
House for sale: 2210 FAIRMOUNT DRIVE, Oakville

50 photos

$1,335,000

2210 Fairmount Drive, Oakville (1019 - WM Westmount), Ontario L6M 5J5

4 beds
4 baths
38 days

Dundas/Postmaster A Rare Opportunity To Own A Truly Special Home Offering Thoughtful Design, Quality Upgrades, And A Beautiful Park-Side Setting, With The Convenience Of Nearby Schools, Parks, And Quick Access To Major Highways. Situated On A 36-Ft Wide Lot, This Meticulously Maintained 4-Bedroom,

Ramesh Agarwalla,Exp Realty
Listed by: Ramesh Agarwalla ,Exp Realty (905) 962-9266
House for sale: 3305 MISTWELL CRESCENT, Oakville

50 photos

$2,388,000

3305 Mistwell Crescent, Oakville (1001 - BR Bronte), Ontario L6L 0A3

4 beds
4 baths
14 days

Cross Streets: Lakeshore & Great Lakes. ** Directions: Lakeshore to Great lakes blvd to Mistwell. Welcome to an exceptional blend of luxury, lifestyle and location in one of Oakville's most coveted lakeside communities. Situated in the exclusive "Waterview Collection" of Lakeshore Woods, this

House for sale: 247 BEECHTREE CRESCENT, Oakville

47 photos

$1,799,000

247 Beechtree Crescent, Oakville (1001 - BR Bronte), Ontario L6L 0A5

4 beds
4 baths
24 days

Cross Streets: Great Lakes Blvd & Rebecca St. ** Directions: Great Lakes Blvd & Beechtree Cres. Experience elevated family living in sought-after Lakeshore Woods with this breathtaking, extensively upgraded home offering over 4,500 sq ft of luxurious finished living space (including 3,035 sq

Peter He,Re/max Hallmark Realty Ltd.
Listed by: Peter He ,Re/max Hallmark Realty Ltd. (647) 739-2618
House for sale: 2091 WILLHAVEN TRAIL, Oakville

31 photos

$1,999,900

2091 Willhaven Trail, Oakville (1019 - WM Westmount), Ontario L6M 5G3

6 beds
5 baths
12 days

Cross Streets: Third Line + Dundas St. ** Directions: West of 3rd Line/N of Pine Glen. RemarksPublic Remarks: An exceptional family residence offering approx 4,000 sq. ft. of beautifully finished living space, this extensively upgraded 5+1 bedroom, 6 bathroom home is ideally situated on a premium

Listed by: Elena Cipriano ,Re/max Escarpment Realty Inc. (905) 639-7676
House for sale: 2180 NORTH RIDGE TRAIL, Oakville

19 photos

$1,748,800

2180 North Ridge Trail, Oakville (1009 - JC Joshua Creek), Ontario L6H 5M3

4 beds
3 baths
12 days

Upper Middle Rd & Ninth Line Welcome to this exceptionally well-maintained home in the prestigious, family-friendly Joshua Creek community of Oakville. Situated on a very rare lot with no rear neighbours, this property offers a private, ravine-like setting surrounded by towering trees - a truly

Frank Leo,Re/max West Realty Inc.
Listed by: Frank Leo ,Re/max West Realty Inc. (416) 917-5466
House for sale: 1362 LYNX GARDENS, Oakville

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$2,250,000

1362 Lynx Gardens, Oakville (1010 - JM Joshua Meadows), Ontario L6H 8A1

4 beds
5 baths
11 days

Cross Streets: Dundas St E. And Ninth Line. ** Directions: Meadowridge Dr and Lynx Gardens. Welcome To This Exceptional Luxury Residence In Oakville's Prestigious Joshua Meadows Community! This Stunning Valery Homes "Nottinghill" Model Offers Approximately 4,397 Sq.Ft. Of Elegant Living Space

Listed by: Jenny Ji ,Re/max Aboutowne Realty Corp. (416) 788-3548
House for sale: 2066 REBECCA Street, Oakville

47 photos

$1,919,888

2066 Rebecca Street, Oakville, Ontario L6L 2A2

5 beds
2 baths
10 days

Third Line/Rebecca Welcome to this stunningly renovated 3+2 bedroom set on an expansive mature lot in one of Oakville's most coveted neighbourhoods, just moments from the shores of Lake Ontario. Surrounded by majestic trees in front providing that extra security and stunning view, 2066 Rebecca

Listed by: Rayo Irani ,Re/max Aboutowne Realty Corp. (647) 802-2020
House for sale: 1403 BAYSHIRE DRIVE, Oakville

50 photos

$2,298,000

1403 Bayshire Drive, Oakville (1009 - JC Joshua Creek), Ontario L6H 6E8

5 beds
5 baths
11 days

Cross Streets: Upper Middle Rd E & Ninth Line. ** Directions: Take Highway 403 and get off from Upper Middle Rd. E. Backs onto Ravine! Rare find in prestigious Joshua Creek, Oakville! This beautifully maintained executive 5-bedroom family home offers 3,314 sq. ft. of elegant above-ground living

Grace Gao,Right At Home Realty
Listed by: Grace Gao ,Right At Home Realty (905) 565-9200
House for sale: 84 PEBBLERIDGE PLACE, Oakville

50 photos

$7,750,000

84 Pebbleridge Place, Oakville (1017 - SW Southwest), Ontario L6K 3Y4

7 beds
9 baths
1 day

Cross Streets: Lakeshore Rd W / Pebbleridge Pl. ** Directions: Via Lakeshore head towards Pebbbleridge Pl then turn right. Set within one of Oakville's most distinguished enclaves, 84 Pebbleridge Place is a newly built modern estate that epitomizes architectural artistry and offers over 7,000

Sam Allan Mcdadi,Sam Mcdadi Real Estate Inc.
Listed by: Sam Allan Mcdadi ,Sam Mcdadi Real Estate Inc. (905) 502-1500
House for sale: 38 SETTLERS ROAD E, Oakville

50 photos

$1,918,000

38 Settlers Road E, Oakville (1008 - GO Glenorchy), Ontario L6H 0Y8

5 beds
5 baths
2 days

Burnhamthorpe Rd & Sixth Line Welcome To 38 Settlers Rd East, A Magnificent Detached Home In Coveted North Oakville! This Like- New, Clean, and Quiet Residence Boasts Over 3,470 Sq. Ft Of Exquisitely Crafted Above-Grade Living Space, Plus An Unfinished 1,250 Sq. Ft Basement With Endless Customization

Listed by: Johnson Li ,Bay Street Integrity Realty Inc. (905) 909-9900
House for sale: 1392 PINECLIFF ROAD, Oakville

50 photos

$1,615,000

1392 Pinecliff Road, Oakville (1022 - WT West Oak Trails), Ontario L6M 3Z1

5 beds
4 baths
10 days

Westoak Trls-Oakhaven & Pinecliff Welcome to West Oak Trails one of Oakville's most desirable, family-friendly neighborhoods surrounded by scenic ravine trails, parks, ponds, & excellent schools. This prime location is close to all amenities, a 4-minute drive to the Oakville Hospital, & offers

Rina Di Risio,Royal Lepage Real Estate Services Ltd.
Listed by: Rina Di Risio ,Royal Lepage Real Estate Services Ltd. (905) 338-3737
House for sale: 2431 CASTLEBROOK ROAD, Oakville

50 photos

$1,999,900

2431 Castlebrook Road, Oakville (1019 - WM Westmount), Ontario L6M 4Z2

4 beds
5 baths
6 days

Cross Streets: Pine Glen Rd. ** Directions: 3rd Line to Kingsridge to Castlebrook. Located on a highly sought-after ravine lot in one of Oakville's most desirable family-friendly neighborhoods sits this beautifully well maintained 3100 sq.ft 4-bedroom family home. Offering elegant living space

Conrad Guy Zurini,Re/max Escarpment Realty Inc.
Listed by: Conrad Guy Zurini ,Re/max Escarpment Realty Inc. (905) 639-7676
House for sale: 265 SNOWDEN Road, Oakville

42 photos

$1,399,000

265 Snowden Road, Oakville, Ontario L6L 3X6

4 beds
2 baths
11 days

Rebecca St/Sabel St/Snowden Rd Nestled in one of Oakville's most sought-after neighborhoods, this beautifully updated bungalow blends timeless charm with modern comfort. The home features three spacious bedrooms on the main floor and a large fourth bedroom on the lower level - perfect for older

James Mccloskey,Re/max Realty Enterprises Inc.
Listed by: James Mccloskey ,Re/max Realty Enterprises Inc. (905) 336-1010
House for sale: 257 SUNRISE Crescent, Oakville

44 photos

$3,100,000

257 Sunrise Crescent, Oakville, Ontario L6L 3L4

4 beds
4 baths
1 day

Rebecca/Sunrise/Sunset Welcome to 257 Sunrise Crescent, a beautifully built family home tucked away on a quiet crescent in the heart of Bronte Village. Built in 2020 with exceptional craftsmanship and top-quality finishes throughout, this residence offers just over 3,000 square feet above grade,

Brad Miller,Century 21 Miller Real Estate Ltd.
Listed by: Brad Miller ,Century 21 Miller Real Estate Ltd. (905) 338-2121
House for sale: 121 RINGWOOD ROAD, Oakville

49 photos

$2,749,000

121 Ringwood Road, Oakville (1003 - CP College Park), Ontario L6H 1K3

6 beds
5 baths
9 days

Cross Streets: Upper Middle Rd & Oxford Ave. ** Directions: Upper Middle Rd / Oxford Ave / Ringwood Rd. Welcome to 121 Ringwood: A custom-built home under 6 years old, offering the perfect blend of luxury, comfort, and modern smart living. The Main Level Features A Spectacular Family Room With

House for sale: 2299 STRATUS DRIVE, Oakville

43 photos

$1,899,000

2299 Stratus Drive, Oakville (1019 - WM Westmount), Ontario L6M 4Z9

5 beds
4 baths
9 days

Cross Streets: Postmaster/Mariposa. ** Directions: From Mariposa turn left on Stratus Dr. Welcome to this beautifully upgraded family home nestled in a sought-after, family-oriented neighbourhood close to Oakville Trafalgar Hospital, parks, transit, schools, and shopping. Recently upgraded

Aleksandra Sylvia Nowak,Meta Realty Inc.
Listed by: Aleksandra Sylvia Nowak ,Meta Realty Inc. (416) 871-2539
House for sale: 489 RAVINEVIEW WAY, Oakville

50 photos

$1,699,000

489 Ravineview Way, Oakville (1018 - WC Wedgewood Creek), Ontario L6H 6T1

5 beds
4 baths
27 days

8th Line & Ravineview Way Spacious and updated 5 bedroom family home located on a family-friendly street in Wedgewood Creek, Oakville. Top Ranking School District (MUNN'S Public School Ranks 74/3052 and IROQUOIS RIDGE High School Ranks 8/747). Lovely landscaping with interlocking stone walkway

House for sale: 44 HEAD STREET, Oakville

49 photos

$2,299,000

44 Head Street, Oakville (1002 - CO Central), Ontario L6K 1L5

4 beds
5 baths
14 days

Cross Streets: Wilson and Rebecca. ** Directions: Rebecca to Wilson to Head St. Welcome to 44 Head St - an exceptional home in the heart of Oakville- steps from Kerr Village & downtown. Enjoy walkable access to local shops, dining & the lakefront-the perfect blend of convenience & tranquility.

House for sale: 1004 ROXBOROUGH DRIVE, Oakville

50 photos

$1,525,000

1004 Roxborough Drive, Oakville (1007 - GA Glen Abbey), Ontario L6M 1E3

4 beds
4 baths
2 days

Cross Streets: Monks Passage / Roxborough Dr. ** Directions: Monks Passage / Roxborough Drive. Welcome to 1004 Roxborough Drive, a beautifully updated family home in Oakville's highly sought-after Glen Abbey community. Offering approximately 3,682 sq ft of finished living space, this 4-bedroom,

House for sale: 2216 NORFOLK DRIVE, Oakville

35 photos

$1,475,000

2216 Norfolk Drive, Oakville (1015 - RO River Oaks), Ontario L6H 6H4

4 beds
3 baths
1 day

Cross Streets: Trafalgar / Glenashton. ** Directions: Trafalgar Rd / Glenashton. Welcome to the heart of River Oaks - one of Oakville's most sought-after family neighbourhoods, and this beautifully maintained 4-bedroom detached home that offers the perfect blend of comfort, functionality, and

Matilda Nestoroska,Re/max Aboutowne Realty Corp.
Listed by: Matilda Nestoroska ,Re/max Aboutowne Realty Corp. (416) 419-3523
House for sale: 125 PALISER COURT, Oakville

44 photos

$2,997,000

125 Paliser Court, Oakville (1017 - SW Southwest), Ontario L6K 2H1

5 beds
5 baths
3 days

Cross Streets: Paliser & Lakeshore Rd W. ** Directions: Lakeshore Rd W- Paliser Crt. Exceptional value in one of South West Oakville's coveted enclaves. Tucked away at the end of a quiet exclusive court just off Lakeshore Road, this custom-built residence sits on a rare, private pie-shaped

Rina Di Risio,Royal Lepage Real Estate Services Ltd.
Listed by: Rina Di Risio ,Royal Lepage Real Estate Services Ltd. (905) 338-3737
House for sale: 491 WARMINSTER Drive, Oakville

26 photos

$1,075,000

491 Warminster Drive, Oakville, Ontario L6L 4N4

4 beds
2 baths
4 days

West of Fourth Line & Bridge Upsizing? You don't want to miss this well-maintained 4-bedroom, 2-bath bungalow nestled in one of West Oakville’s most desirable enclaves. Set on an impressive pie-shaped corner lot spanning over 8,500 sq. ft., this property offers endless potential, whether

Chris Cipriani,Re/max Escarpment Realty Inc.
Listed by: Chris Cipriani ,Re/max Escarpment Realty Inc. (905) 978-7834

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.