$3,000/mo - 18831 Winston Churchill Boulevard, Caledon
Detached for Rent in Caledon
48 days on marketNeighbourhood: Rural Caledon
- MLS Number
- W13530130
- Property Type
- Detached
- Status
- active
- Days on Site
- 48
- Bedrooms
- 2
- Bathrooms
- 1
- Square Feet
- 1,100 - 1,499 sqft
- Neighbourhood
- Caledon
- Listing Brokerage
- CENTURY 21 LEGACY LTD.
Welcome to your own private country retreat. Tucked away on a picturesque 1-acre lot, this beautifully maintained home welcomes you with a tree-lined driveway that sets the tone for the peace, privacy, and natural beauty that await. From the moment you arrive, you'll be captivated by the stunning views, charming curb appeal, and thoughtfully updated finishes throughout. Designed for both comfort and lasting value, this home features an expansive new deck, updated vinyl siding, a detached garage, and numerous quality improvements completed over the years. The extensive list of upgrades overtime. Whether you're seeking a tranquil escape or a place to call home, this exceptional property offers the perfect blend of country charm, modern updates, and move-in-ready appeal. Basement not included. No one will be in basement.
Discover Rural Caledon
Rural Caledon is a vibrant community in the Greater Toronto Area, offering excellent amenities, schools, and transportation options. This area is popular with families and professionals seeking a balanced lifestyle with access to urban conveniences and natural spaces.
Why Live in Rural Caledon
- •Convenient location in Caledon
- •Access to local shops and dining
- •Good public transit connections
- •Community parks and green spaces
- •Well-maintained neighbourhoods
Nearby Schools
Transit & Commuting
- •MiWay bus routes throughout the area
- •GO Transit stations within driving distance
- •Easy highway access to 401/403/QEW
- •Walking distance to local amenities
Parks & Amenities
- •Local parks and recreational facilities
- •Community centres
- •Shopping plazas nearby
- •Restaurants and cafes
Lifestyle & Community
Rural Caledon offers a wonderful quality of life with a mix of residential charm and urban convenience. Residents enjoy easy access to schools, parks, and shopping, making it an ideal location for families and professionals alike.
18831 Winston Churchill Boulevard, Caledon
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How this lease stacks up against the local rental market
Estimated Monthly Budget
Things to Confirm Before Signing
· Are utilities included, or separate?
· How many parking spots are included?
· Is the landlord open to a 1-year or 2-year lease?
· Are pets and small renovations (paint, hooks) allowed?
· When was the last rent increase, if there is a prior tenant?
Utility estimates are approximate and vary by season, habits, and what the landlord includes. Always confirm inclusions with the listing agent.
Joe's Thoughts
Honest perspective from 30+ years of GTA real estate experience
Fairly Priced Rental
At $3,000/mo, this is in line with typical 2-bedroom rents in Caledon (~$2,900/mo). The rent itself may be firm, but there's often room to negotiate on lease terms — move-in date, appliance inclusions, or parking.
Negotiation Opportunity
At 48 days on site, this property has exceeded the typical selling timeline for Caledon. This creates leverage for buyers. The seller may be motivated by carrying costs, life circumstances, or previous deals falling through. I'd recommend a strategic offer below asking with terms that favour you.
Detached Home Advantages
Detached homes in Caledon are increasingly scarce and valuable. You'll have no shared walls, full control over renovations, and typically stronger appreciation. Consider the lot size and potential for future additions or basement apartment income. Detached homes also offer the most flexibility for growing families.
About Rural Caledon
I know Rural Caledon well from working with many buyers and sellers here. Each pocket has its own character - let me share what I've learned about this specific street and block. During our showing, I'll point out local amenities, school catchments, and what similar homes have sold for recently.
Lease Terms to Negotiate
Don't just focus on the monthly rent — the lease terms matter just as much. I always advise my rental clients to clarify: what's included (parking, storage, utilities), the lease length options, the landlord's policy on renewals, and whether small personalizations like painting are permitted. These details can make or break your experience over 12–24 months.
Let's Walk Through It Together
Photos can't tell you about traffic noise, natural light at different times of day, or how well the landlord maintains the property. When we view it together, I'll assess the condition of appliances, HVAC, and finishes — and flag anything that might become a headache. I'll also help you understand the lease terms before you sign anything.