Proudly Canadian

This Property Is No Longer Available

Looking for similar properties? We can help you find your perfect home.

Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 1 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 2 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 3 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 4 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 5 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 6 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 7 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 8 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 9 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 10 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 11 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 12 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 13 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 14 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 15 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 16 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 17 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 18 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 19 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 20 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 21 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 22 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 23 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 24 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 25 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 26 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 27 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 28 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 29 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 30 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 31 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 32 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 33 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 34 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 35 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 36 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 37 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 38 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 39 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 40 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 41 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 42 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 43 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 44 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 45 of 46
Detached for sale at 296 Whitehead Crescent, Caledon - 5 bedroom, 2 bathroom - Photo 46 of 46
1 / 46• 43 locked
View on map
Inactive

$837,000

296 Whitehead Cres

Caledon, ON L7E 3Y1

296 Whitehead Cres, Caledon — Listed at $837,000. 5 bedroom, 2 bathroom Bungalow-Raised Detached. MLS® W13027408.

5Beds
2Baths
1100-1500sqft
Detached
Bungalow-Raised
6Parking
$4,677Taxes/yr · 2025
See similar homes in this price range

Description

Welcome to 296 Whitehead Crescent, nestled in Bolton's highly sought-after North Hill-one of the most desirable, family-friendly neighbourhoods in the area. This beautifully maintained raised bungalow offers exceptional versatility, making it an ideal fit for families, investors, or those seeking multi-generational living. A standout feature of this home is the fully self-contained two-bedroom lower-level apartment with its own private entrance, complete with a kitchen, ensuite laundry, and a 3-piece bath-perfect for generating rental income or providing comfortable, independent space for extended family. For those who prefer a traditional layout, the home can easily function as a spacious 3+2 bedroom residence. Part of the garage has been adapted to maximize functionality, offering a separate private space ideal for a home office, studio, or small business-creating a true work-from-home solution without compromising your living space. Outside, enjoy a massive fully fenced backyard-perfect for entertaining, kids, and pets-along with a large driveway accommodating up to six vehicles.Major updates have already been taken care of, including windows, roof, furnace, and air conditioning, providing peace of mind and true move-in readiness.All of this is ideally located within walking distance to schools, parks, trails, recreation centres, and the vibrant charm of downtown Bolton.This is more than just a home-it's an opportunity to live, invest, and grow in one of Bolton's most coveted communities.

Property Details

Property TypeDetached
StyleBungalow-Raised
CommunityBolton North
Rooms11
Kitchens2
Washrooms2
Square Feet1100-1500 sqft
Lot Dimensions37.19 × 165.67 ft
Fronting OnWest
Dir/Cross StKingsview & Bolton Heights Rd
Garage TypeNone
Parking Drive Spaces6
Total Parking Spaces6
ExteriorBrick, Aluminum Siding
RoofAsphalt Shingle
FoundationPoured Concrete
BasementSeparate Entrance, Finished
Heating TypeForced Air
Heating SourceGas
A/CCentral Air
SewersSewer
Taxes (2025)$4,677
HSTIncluded In
Listed Date4/21/2026
Days on Market205 days
PossessionFlexible

Virtual Tour

Explore from home

This Listing Is No Longer Active

Browse similar active listings or get a free home evaluation.

Listing Courtesy of: ROYAL LEPAGE RCR REALTY

MLS® #W13027408

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.

HouseIndex Take: 296 Whitehead Crescent

This detached (Bungalow-Raised) is located in the Bolton North neighbourhood of Caledon.

The home offers 5+2 bedrooms, 2 bathrooms.

Features include a separate entrance, finished basement, 6 parking spaces.

Additional details: lot dimensions of 37.19 × 165.67 feet.

About Caledon Real Estate

This Detached is located in the Bolton North community in Caledon. Caledon is a vast, scenic municipality in Peel Region spanning the Niagara Escarpment and Oak Ridges Moraine. Bolton is the primary urban centre, while Caledon East and Inglewood offer village living. Popular with buyers seeking acreage, hobby farms, and a rural-meets-suburban lifestyle within commuting distance of Toronto. Detached homes in Caledon are in high demand among families seeking space, privacy, and long-term equity growth.

Niagara Escarpment & Forks of the CreditBolton urban centreHobby farms & rural estate lotsHumber River trails
~60 min commute to downtown TorontoWalkability: Rural — car essential except Bolton core