

















































$4,599,000 - 5258 Winston Churchill Boulevard, Erin
Detached for Sale in Erin
Neighbourhood: Rural Erin
- MLS Number
- X13648806
- Property Type
- Detached
- Status
- active
- Days on Site
- 17
- Bedrooms
- 4
- Bathrooms
- 3
- Square Feet
- 3,500 - 3,999 sqft
- Neighbourhood
- Erin
- Listing Brokerage
- ROYAL LEPAGE RCR REALTY
Imagine waking up to peaceful countryside views, spending afternoons by the pool, evenings around the fire and having the space to enjoy the country lifestyle you've worked for. Set on 25 private acres, this remarkable estate offers over 5,800 sq. ft. of living space thoughtfully designed for everyday living, entertaining and pursuing the hobbies you love. Beyond the gated entrance, the property unfolds with an impressive pond, beautifully maintained grounds, mature landscaping, multiple paddocks, a drive shed, vegetable garden, fruit trees, chicken coop with sugar shack, gazebo, cabana with sauna and shower, and a heated saltwater pool surrounded by generous patio space. For those seeking exceptional workspace and versatility, the detached 3-car garage features a finished upper-level office with a propane stove, while the nearly 4,000 sq. ft. three-level barn includes 4 horse stalls, an aviary, workshop, feed room and a self-contained living area with kitchen and 3-piece bath. Inside, warmth and character are found throughout. The cherry kitchen with a large island and wood-burning fireplace creates a natural gathering place, while the conservatory with heated slate floors and the Muskoka room invite you to slow down and enjoy every season. A separate suite with its own entrance offers added flexibility for family or guests. The spacious primary retreat includes a private hot tub walkout, custom cherry wardrobe and a beautifully appointed ensuite. The finished lower level features a temperature-controlled wine cellar, home theatre, billiards room, recreation area and additional kitchen/laundry space. This is a property where country living meets comfort, flexibility and unforgettable moments.
Estimate your monthly payments for this property
Estimated Payment
$20,342.93/mo
5-yr fixed avg.
Rates shown are estimates based on typical Ontario 5-year fixed rates. Canadian mortgages use semi-annual compounding as required by law. CMHC insurance applies to purchases under $1.5M with less than 20% down. Estimated property tax uses an approximate 0.85% rate. Contact us for current rate options and pre-approval.
Discover Rural Erin
Rural Erin 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 Erin
- •Convenient location in Erin
- •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 Erin 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.
5258 Winston Churchill Boulevard, Erin
Open in Google MapsUse the map controls to zoom, pan, and switch between map and satellite views. Drag to explore the neighbourhood.
Rental income estimator & ROI calculator
Monthly Cash Flow Breakdown
Note: These are estimates only. Actual figures may vary based on market conditions, property condition, and other factors. Consult with a financial advisor for personalized advice.

Joe's Thoughts
Honest perspective from 30+ years of GTA real estate experience
Premium Pricing
At $1314/sqft, this property is priced above the Erin average of $950/sqft. I'd want to see upgraded finishes, premium location, or recent renovations to justify this price point. During our showing, I'll point out exactly what you're paying extra for.
Market Position
At 17 days on site, this property has had reasonable exposure. It hasn't sold immediately (which often indicates overpricing), but isn't languishing either. There's likely room for a 3-5% negotiation from asking price.
Detached Home Advantages
Detached homes in Erin 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.
Larger Home Realities
At 3,500 sqft, this is a substantial home. Budget approximately $400-600/month more for utilities compared to an average-sized home. Maintenance costs scale with size too - roof, HVAC, and cleaning all cost more. That said, space is a luxury that's hard to add later, and larger homes often have better resale in family-oriented neighbourhoods.
Family-Friendly Layout
4 bedrooms hits the sweet spot for most families. You'll have room for 2-3 children plus a home office or guest room. This is the most sought-after configuration for families relocating to Erin. Good resale value as demand remains consistent.
Bathroom Count Matters
With 3 bathrooms, morning routines are much smoother. Multiple bathrooms significantly improve daily livability and are a major selling point for resale. Buyers consistently pay more for adequate bathroom counts - this is a strong feature.