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Detached for sale at 2049 Highpoint Side Road, Caledon - 4 bedroom, 4 bathroom - Photo 1 of 60
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$3,788,888

2049 Highpoint Side Rd

Caledon, ON L7K 0J9

2049 Highpoint Side Rd, CaledonListed at $3,788,888. 4 bedroom, 4 bathroom Bungalow. MLS® W13122204.

4Beds
4Baths
2500-3000sqft
Bungalow
23Parking
$6,804.52 (2026)

What's this home worth?

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Description

Welcome to this extraordinary custom-built bungalow nestled on 25 clear acres, offering over 5,500 sq. ft. of luxurious living space plus a remarkable 5,000 sq. ft. insulated workshop-perfect for entrepreneurs, hobbyists, or those seeking ultimate versatility. This meticulously designed home features a chef-inspired gourmet kitchen with premium Wolf and Sub-Zero appliances, custom maple cabinetry, and elegant quartz countertops. Soaring 10 ft ceilings, rich maple hardwood floors, and detailed crown molding elevate the main living areas, while the grand living room showcases a striking double-sided fireplace for added warmth and sophistication. The spacious primary bedroom offers a private retreat complete with a lavish ensuite. A fully finished walkout basement provides exceptional additional living space, including a second kitchen and direct access to a covered patio-ideal for entertaining or multi-generational living. Enjoy breathtaking views from the expansive balcony with an outdoor fireplace, overlooking the serene acreage. Additional features include geothermal heating and cooling, central vacuum, multiple propane access points, surround sound wiring, and full video surveillance and alarm systems. The standout 5,000 sq. ft. insulated workshop is built to impress, featuring 18 ft ceilings, two 14 ft drive-in doors, and robust electrical capacity with a 200 amp service plus two 200 amp subpanels. Fully equipped with motion-sensor lighting, electric heaters, and advanced security offering endless possibilities for business or personal use.

Property Details

Property TypeDetached
StyleBungalow
CommunityRural Caledon
Rooms14+4
Kitchens2
Washrooms4
Square Feet2500-3000 sqft
Lot Dimensions691 × 1564 ft
Fronting OnSouth
Dir/Cross StHWY 10/ HIGHPOINT SIDE RD
Garage TypeAttached
Garage Parking Spaces3
Parking Drive Spaces20
Total Parking Spaces23
ExteriorStone, Stucco (Plaster)
RoofAsphalt Shingle
FoundationPoured Concrete
BasementFinished with Walk-Out
Fireplace FeaturesYes
Heating TypeForced Air
Heating SourcePropane
A/CCentral Air
SewersSeptic
Taxes (2026)$6,804.52
HSTIncluded In
SecurityAlarm System, Monitored, Security System, Smoke Detector
Other StructuresGarden Shed, Workshop
Listed Date5/13/2026
Days on Market29 days
Possession30/60/90TBD

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Listing Courtesy of: RE/MAX SPECIALISTS TEAM SUKHVINDER

MLS® #W13122204

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: 2049 Highpoint Side Road

This detached (Bungalow) is located in the Rural Caledon neighbourhood of Caledon.

The home offers 4+1 bedrooms, 4 bathrooms.

Features include a finished with walk-out basement, 23 parking spaces including a 3-car garage, a fireplace.

Additional details: lot dimensions of 691 × 1564 feet.

Listed at $3,788,888 CAD with annual property taxes of $6,804.52 (2026). This listing has been on the market for 29 days.

About Caledon Real Estate

This Detached is located in the Rural Caledon 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