5258 Winston Churchill Boulevard, Erin, ON N0B 1T0
  • $4,599,000

Overview

  • Detached, Style Backsplit 5
  • Type
  • 4
  • Bedrooms
  • 3
  • Bathrooms

Description

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.

  • Address: Winston Churchill
  • City: Erin
  • State/county: Wellington
  • Zip/Postal Code: N0B 1T0
  • Area: Rural Erin

Details

Updated on October 9, 2026 at 9:51 pm
  • Price $4,599,000
  • Bedrooms 4
  • Bathrooms 3
  • Type Detached, Style Backsplit 5
  • Property Status Residential Freehold

Additional details

  • Bedrooms 4
  • Tax Year 2026
  • Square Footage 3500-5000
  • Washrooms 3
  • Kitchens 1
  • Total Kitchens 1
  • Family Room Yes
  • Basement Finished
  • Approximate Age 51-99
  • Heating Type Forced Air
  • Heating Fuel Propane
  • Air Conditioning Central Air
  • Sewers Septic
  • Front 352.51
  • Depth 0
  • Lot Size 25-49.99 acres
  • Garage Type Detached
  • Parking Spaces 10
  • Total Parking Spaces 15
  • Pool Inground
  • Exterior Finish Board & Batten, Stone
  • Property Orientation West
  • Taxes 13679
  • Occupancy Owner
  • Cross Street Winston Churchill Blvd & The Grange Sideroad
  • Courtesy of ROYAL LEPAGE RCR REALTY
  • Price per Sq Ft ~$1,082 (at 4,250 sq ft)
  • Listed Aug 7, 2026 ยท 63 days on market

Mortgage Calculator

Contact Information

View Listings

Enquire About This Property

0 Review

Sort by:
Leave a Review

Leave a Review

Compare listings

Compare
CallGet listings
Questions & answers

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?

5258 Winston Churchill Boulevard is listed for $4,599,000. With 20% down ($919,800), the mortgage payment would be roughly $18,530 a month at 4.49% over 30 years, before property tax and utilities. That figure is an illustration, not a quote.

How many bedrooms and bathrooms does 5258 Winston Churchill Boulevard have?

5258 Winston Churchill Boulevard has 4 bedrooms and 3 bathrooms.

How big is 5258 Winston Churchill Boulevard?

The listing puts the above-grade living space between 3,500 and 5,000 sq ft. The board reports a range rather than an exact figure, and it does not include the basement.

What type of home is 5258 Winston Churchill Boulevard?

5258 Winston Churchill Boulevard is a detached 5-level backsplit in Rural Erin, Erin. The exterior is board & batten, stone. The listing gives its age as 51-99 years.

Does 5258 Winston Churchill Boulevard have a finished basement?

The basement is listed as finished.

Does 5258 Winston Churchill Boulevard have a garage, and how much parking is there?

Yes. It has a 5-car detached garage. There is parking for 15 vehicles in total: 10 on the driveway and 5 in the garage.

How is 5258 Winston Churchill Boulevard heated and cooled?

Heating is forced air (propane). Cooling is central air.

Does 5258 Winston Churchill Boulevard have a pool?

Yes. The listing shows an inground pool. Ask about its age, liner and equipment before you offer, since those are the costly parts to replace.

What are the property taxes for 5258 Winston Churchill Boulevard?

Property taxes are $13,679 a year (2026), or about $1,140 a month.

What neighbourhood is 5258 Winston Churchill Boulevard in?

5258 Winston Churchill Boulevard is in the Rural Erin community of Erin, Wellington Region. The nearest main intersection is Winston Churchill Blvd & The Grange Sideroad. The postal code is N0B 1T0.

Is 5258 Winston Churchill Boulevard still for sale?

Yes. 5258 Winston Churchill Boulevard is an active listing (MLS® X13648806), on the market since August 7, 2026. Listings here update from the board through the day and come down once a home sells.

Has 5258 Winston Churchill Boulevard sold before, and for how much?

Past sales, leases and expired listings for this 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.