Proudly Canadian
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 1 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 2 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 3 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 4 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 5 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 6 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 7 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 8 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 9 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 10 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 11 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 12 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 13 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 14 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 15 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 16 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 17 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 18 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 19 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 20 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 21 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 22 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 23 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 24 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 25 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 26 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 27 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 28 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 29 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 30 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 31 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 32 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 33 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 34 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 35 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 36 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 37 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 38 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 39 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 40 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 41 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 42 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 43 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 44 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 45 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 46 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 47 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 48 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 49 of 50
Detached for sale at 2371 Calloway Drive, Oakville - 5 bedroom, 5 bathroom - Photo 50 of 50
1 / 5047 locked
Active

$1,899,900

2371 Calloway Dr

Oakville, ON L6M 0C1

2371 Calloway Dr, OakvilleListed at $1,899,900. 5 bedroom, 5 bathroom 2-Storey Detached. MLS® W13612000.

5Beds
5Baths
3000-3500sqft
Detached
2-Storey
4Parking
$8,488Taxes/yr · 2025

What's this home worth?

Get a free estimate for 2371 Calloway Dr

Description

Welcome to this extensively updated family home in Oakville's highly desirable Westmount community, backing onto lush greenspace & scenic walking trails. Situated on a premium landscaped lot, this impressive residence offers over 4,260 sq. ft. of finished living space & was extensively renovated in 2023. Hardwood flooring extends throughout the main living areas, upper hall & all bdrms, complemented by crown moulding, California shutters & neutral décor. The main level features a private office, combined living & dining room, & a bright family room w/ coffered ceilings & gas fireplace open to the chef-inspired kitchen. The open-concept kitchen & breakfast area showcase an oversized quartz island w/ breakfast bar & waterfall edge, quartz backsplash, extended custom white cabinetry w/ glass display accents, walk-in pantry, S/S appliances, undermount sink, designer pendant lighting, pot lights & large-format porcelain tile flooring. The breakfast area is surrounded by windows & offers a w/o to the fully fenced backyard w/ spacious deck overlooking tranquil greenspace. A wood staircase w/ spindles leads to the upper level featuring 4 spacious bdrms. The primary retreat offers 2 walk-in closets & a spa-inspired ensuite w/ double sinks, large glass shower, soaker tub & water closet. Bdrms 2 & 3 share a semi-ensuite 4-pc bath, while an additional 4-pc bath & upper-level laundry w/ built-in cabinetry, counter space, utility sink & side-by-side washer/dryer add convenience. The finished basement features laminate flooring, pot lights, large rec room, 5th bedroom & full bath. Additional highlights include central vacuum, roof (2018), double garage w/ inside entry & double driveway. Close to top-rated schools, parks, trails, shopping, transit, Oakville Trafalgar Hospital & major highways.

Property Details

Property TypeDetached
Style2-Storey
Community1019 - WM Westmount
Approximate Age16-30
Rooms9+2
Kitchens1
Washrooms5
Square Feet3000-3500 sqft
Lot Dimensions39.7 × 83.66 ft
Fronting OnEast
Dir/Cross StBronte Rd/West Oak Trails
ViewForest
Garage TypeAttached
Garage Parking Spaces2
DrivePrivate Double
Parking Drive Spaces2
Total Parking Spaces4
ExteriorStone, Stucco (Plaster)
RoofAsphalt Shingle
FoundationPoured Concrete
BasementFinished, Full
Fireplace FeaturesNatural Gas
Heating TypeForced Air
Heating SourceGas
A/CCentral Air
SewersSewer
Taxes (2025)$8,488
HSTIncluded In
Listed Date7/28/2026
Days on Market8 days
PossessionTBA

Virtual Tour

Explore from home

Same-day showings available
5.0Rated 5 stars on Google ReviewsWhatsApp Us About This Listing

Property Insights

Home Value
Estimate

Listing Courtesy of: CENTURY 21 MILLER REAL ESTATE LTD.

MLS® #W13612000

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

Thinking about living in Oakville?

Explore the neighbourhood guide for Oakville — market trends, popular areas, buyer tips, and more.

HouseIndex Take: 2371 Calloway Drive

This detached (2-Storey) is located in the 1019 - WM Westmount neighbourhood of Oakville.

The home offers 5+1 bedrooms, 5 bathrooms.

Features include a finished, full basement, 4 parking spaces including a 2-car garage, a fireplace.

Additional details: lot dimensions of 39.7 × 83.66 feet.

Listed at $1,899,900 CAD with annual property taxes of $8,488 (2025).

About Oakville Real Estate

This Detached is located in the 1019 - WM Westmount community in Oakville. Oakville is an affluent lakefront town in Halton Region known for heritage estates in Old Oakville, a thriving downtown core along Lakeshore Road, and excellent schools. The QEW provides quick access to Toronto and Hamilton, while the Oakville GO station offers 30-minute service to Union. It consistently ranks among Canada's best places to live. Detached homes in Oakville are in high demand among families seeking space, privacy, and long-term equity growth.

Lakefront trails & Bronte HarbourTop-ranked Halton District School Board30-minute GO Train to Union StationBoutique shops along Lakeshore Road
~35 min commute to downtown TorontoWalkability: Walkable downtown — suburban outer areas
View full Oakville neighbourhood guide →