5258 Winston Churchill Boulevard, Erin, ON N0B 1T0
Rural Erin, Erin · Near Winston Churchill Blvd & The Grange Sideroad · View map
About this home
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.
The home
- Type
- Backsplit
- Style
- Backsplit 5
- Square footage
- 3500-5000 sq ft
- Bedrooms
- 4
- Bathrooms
- 3
- Kitchens
- 1
- Rooms
- 14
- Basement
- Finished
- Faces
- West
- View
- Garden, Forest, Pond, Trees/Woods
- Approximate age
- 51-99 years
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Exterior
- Board & Batten, Stone
Heating & cooling
- Heating fuel
- Propane
- Heating type
- Forced Air
- Air conditioning
- Central Air
- Fireplace
- Yes
Garage & parking
- Garage
- Detached
- Garage spaces
- 3
- Driveway spaces
- 10
- Total parking
- 15
Taxes & other
- Property taxes
- $13,679/yr
- Tax year
- 2026
- Occupancy
- Owner
- Possession
- TBD
- Cross street
- Winston Churchill Blvd & The Grange Sideroad
- Neighbourhood
- Rural Erin
More
- Price per sq ft
- ~$1,082 (at 4,250 sq ft)
- Listed
- Aug 7, 2026 · 66 days ago
- MLS® number
- X13648806
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The home and its surroundings
- Auto Garage Door Remote
- Built-In Oven
- Carpet Free
- Generator - Full
- In-Law Suite
- Propane Tank
- Sauna
- Sump Pump
- Water Heater
- Water Softener
- Deck
- Lawn Sprinkler System
- Landscaped
- Porch
- Private Pond
- Security Gate
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
5258 Winston Churchill Boulevard, Erin, ON N0B 1T0
Rural Erin, Erin · Near Winston Churchill Blvd & The Grange Sideroad
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Listing history for 5258 Winston Churchill Boulevard
See what this home and others at the same address were listed for, what they sold for, and how long it took.
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Frequently asked questions about 5258 Winston Churchill Boulevard
Answers come straight from this home’s MLS® listing.
How much is 5258 Winston Churchill Boulevard listed for, and what would it cost each month?
5258 Winston Churchill Boulevard is listed for $4,599,000. With 20% down ($919,800), the mortgage payment would be roughly $18,551 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $19,691 a month, all in. That figure is an illustration, not a quote.
Is 5258 Winston Churchill Boulevard freehold or a condo, and is there a monthly fee?
5258 Winston Churchill Boulevard is a backsplit in Rural Erin, Erin. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 5258 Winston Churchill Boulevard have?
5258 Winston Churchill Boulevard has 4 bedrooms and 3 bathrooms. The listing gives the style as backsplit 5.
Does 5258 Winston Churchill Boulevard have a garage and parking?
Yes. The listing shows the garage as detached, with room for 3 cars. The driveway adds 10 spaces. In total the listing counts 15 parking spaces.
Does 5258 Winston Churchill Boulevard have a finished basement?
The listing describes the basement as finished. Finished basement space is usually not counted in the square footage shown.
What style of home is 5258 Winston Churchill Boulevard?
5258 Winston Churchill Boulevard is a backsplit. A backsplit has its levels staggered front to back: from the street it looks like a bungalow, with extra levels at the rear.
Does 5258 Winston Churchill Boulevard have a pool?
Yes. The listing shows inground for the pool. Ask about its age, liner and equipment before you offer, since those are the costly parts to replace.
How big is 5258 Winston Churchill Boulevard?
The listing puts the home between 3,500 and 5,000 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement.
How is 5258 Winston Churchill Boulevard heated and cooled?
Heating is forced air (propane). Cooling is central air.
What are the property taxes for 5258 Winston Churchill Boulevard?
Property taxes are $13,679 a year (2026), or about $1,140 a month.
Where is 5258 Winston Churchill Boulevard?
5258 Winston Churchill Boulevard is in the Rural Erin community of Erin. The nearest main intersection is Winston Churchill Blvd & The Grange Sideroad. The postal code is N0B 1T0.
How long has 5258 Winston Churchill Boulevard been on the market?
5258 Winston Churchill Boulevard was listed on August 7, 2026. It has been on the market for 66 days. It is an active listing (MLS® X13648806). Listings here update from the board through the day and come down once a home sells.
What are similar bungalows near 5258 Winston Churchill Boulevard asking?
Similar bungalow-style homes for sale nearby right now include 9727 Dundas Street E at $3,399,000 (4+2 bed), 6168 1 St Line at $4,200,000 (3+3 bed) and 101 Perryman Court at $4,999,900 (5+2 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 5258 Winston Churchill Boulevard sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 5258 Winston Churchill Boulevard?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-619-2256.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar bungalows nearby
More bungalow-style homes for sale near Rural Erin, picked by style, size and price.
Bungalow$3,399,0009727 Dundas Street E, Erin4+2 bed · 7 bath · Rural ErinCourtesy of: ROYAL LEPAGE RCR REALTYView home →
Bungalow$4,200,0006168 1 St Line, Erin3+3 bed · 5 bath · Rural ErinCourtesy of: iCloud Realty Ltd.View home →
Bungaloft$4,999,900101 Perryman Court, Erin5+2 bed · 9 bath · Rural ErinCourtesy of: ROYAL LEPAGE SIGNATURE REALTYView home →Courtesy of: ROYAL LEPAGE RCR REALTY
PropTx MLS® assumes no responsibility for the accuracy of any information shown. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale or lease of real estate and may not be used for any commercial purpose or any other purpose.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.