296 Whitehead Crescent

FOR SALE
$837,000
296 Whitehead Crescent, Caledon
296 Whitehead Crescent
296 Whitehead Crescent
296 Whitehead Crescent
296 Whitehead Crescent
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3 + 2
BEDROOMS
2
BATHROOMS
2
KITCHENS
11
ROOMS
W13027408
MLSID
Contact Us
Property 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 Features
Carpet Free, In-Law Suite
Property Details
Address
296 Whitehead Crescent
Community
Postal Code
L7E 3Y1
Property Type
Detached, Detached
Lot Size
37' x 166'
Taxes
$4,677 (2025
Basement
Separate Entrance, Finished
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Parking Spaces
6
Garage Type
None
Listing contracted with Royal Lepage Rcr Realty
320 Pearl Street, Caledon
3+1
BEDS
2
BATHS
$799,000
FOR SALE
Welcome to 320 Pearl Street, nestled in the highly desirable Bolton West community. Sitting proudly on an oversized 80-ft frontage, this property offers exceptional outdoor space, a mature private backyard, and plenty of room for family gatherings or quiet evenings at home.The curb appeal is undeniable, with a large driveway that comfortably parks three cars. Step inside to a bright, inviting main level filled with natural light. The open-concept layout flows seamlessly across hardwood floors, creating a warm and welcoming atmosphere. The spacious living room, highlighted by a large picture window, connects effortlessly to the dining area, with the kitchen conveniently set just off to the side having access to the backyard. This level also features a comfortable primary bedroom, two additional well-sized bedrooms, and an updated 4-piece bathroom, 2023. The lower level offers incredible versatility with a private nanny/in-law suite, complete with its own full kitchen, a generous living area, and a 3-piece bathroom-ideal for extended family or guests. Large windows bring in plenty of natural light, making the space feel open and inviting.Outside, the fully fenced yard is a standout feature. With mature greenery and a deck perfect for entertaining, it's a space designed for relaxation, play, and memorable summer evenings.Located on a quiet, family-friendly street that kids will love, this home is just minutes from parks, a skating rink, recreation centre, both public and separate schools, shopping, restaurants, and historic downtown Bolton. This is a rare opportunity to own a well maintainedhome with room to grow in one of Bolton's most sought-after neighbourhoods. Don't miss your chance to make it yours.
19774 Main Street, Caledon
3
BEDS
2
BATHS
$798,000
FOR SALE
Nestled in the charming and peaceful village of Alton, this beautifully renovated detached home offers the perfect blend of modern comfort and small-town charm. Featuring 3 spacious bedrooms, this move-in-ready property has undergone extensive top-to-bottom renovations in 2025, showcasing quality finishes and thoughtful updates throughout.The inviting main floor features a bright open-concept living and dining area, ideal for both everyday living and entertaining guests. The stunning modern kitchen is complete with elegant granite countertops, extended-height cabinetry offering abundant storage, stainless steel appliances, and a stylish contemporary backsplash.Upstairs, you'll find 3 generously sized bedrooms filled with natural light, providing comfortable accommodations for families or guests alike. The home also offers excellent functionality with a large private driveway providing ample parking, along with newly constructed front and rear decks perfect for outdoor enjoyment and entertaining.Recent major upgrades include new windows, a new roof, and a new gas furnace, offering added efficiency, comfort, and peace of mind for years to come. A spacious detached garage provides additional parking, workshop potential, or extra storage space. Freshly painted both inside and out, the entire property has been thoughtfully updated with a clean and modern aesthetic.Ideally located just minutes from the renowned Millcroft Spa and the prestigious Osprey Valley Golf Club, host of the Canadian Open, this exceptional property also offers convenient access to Orangeville, Mono, and Brampton, making it an ideal choice for commuters and lifestyle buyers alike. Some images have been virtually staged for illustrative purposes only.
1442 Mill Street, Caledon
3
BEDS
2
BATHS
$775,000
FOR SALE
Charming 3-Bedroom Home in the Heart of Historic Cheltenham Nestled in the picturesque village of Cheltenham, this inviting 3-bedroom, 2-bath, two-storey home blends small-town charm with the beauty of Caledon's natural surroundings. Set in an old historic mill village along the scenic Credit River, the property offers tranquil views, rolling hilly terrain, and a warm community atmosphere. Enjoy easy access to the Caledon Railway Trail and the renowned Bruce Trail-perfect for hiking ,cycling, and year-round outdoor adventures. Explore nearby landmarks like the Cheltenham Badlands and Forks of the Credit, or stroll to the Cheltenham General Store, just a short walkaway for your morning coffee or local goods .Whether you're seeking a serene retreat or a family-friendly home surrounded by nature and history, this property captures the essence of countryside living-only minutes from urban conveniences.
44 Brawton Drive, Caledon
3
BEDS
1
BATHS
$775,777
FOR SALE
RBID HOME FOR SALE. HOMEOWNER RELOCATING ($775,777) Attention Developers, Investors, and Custom Builders. Rare opportunity to secure a premier corner lot in the prestigious enclave of Palgrave. This property offers a unique canvas for a luxury rebuild or a strategic value-add investment. Top 5 Reasons you will love the property: #1. Development Potential Unlock the full utility of this sprawling lot with the ability to build an Additional Residential Unit (ARU). Under Section 6 of the local zoning by-law, this property supports forward-thinking density. Key development standards include: Accessory Building Height: Maximum height of 4.5 metres. Lot Coverage: Up to 5% of the total lot area can be dedicated to accessory building, perfect for a detached garden suite, carriage house, or high-end workshop. Zoning standards, and specific ARU policies are governed by Section 6 of the Zoning By-law, offering a roadmap for your next project. #2. Charming 3-bedroom bungalow sits on a beautiful sprawling lot. #3. A workshop with electricity offers ample storage space for vehicles, tools, or hobby gear. #4. Situated in one of Caledon's most sought-after communities, you are steps away from world-class amenities. Minutes to the Caledon Equestrian Park, Albion Hills Conversation Area, and the Bruce Trail for hiking, skiing, and cycling. Only 10 minutes to the urban comforts of Bolton, including big-box retail, professional services, and fine dining. Easy access to Highway 50 and Highway 9, providing a smooth commute to the GTA and Pearson Airport (approx. 30 mins). Walking to Palgrave Public School, local parks, and the charming Caledon Hills Brewing Company. #5 Whether you are looking to build a multi-generational family estate or a high-yield investment property, 44 Brawton Drive provides the space, zoning flexibility, and location to make it a reality. Don't miss out on one of the last great development pockets in Palgrave!
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