Welcome to 5258 Winston Churchill Blvd Stay Awhile
House, Buildings, Pond, Land.
Maintained Property Approx 25 Acres
Back Of House & Sunroom
Stone Wall Along Driveway
Composite Back deck W/O From Living Room
Saltwater inground pool
Pool House
Chicken Coop
Bunkie
Sauna
Front Of Home, Beautifully Landscaped
Living Room with Cove Lighting and Large Windows
Sliding doors lead to Composite Backyard Deck
Hand Painted Ceiling Art
Built-in Slate Planters
Dining room with Slate flooring and skylights
Dining Room Looks out to the backyard
Built in Dining Room Bookshelves
Hand Painted Walls
Seasonal Sunroom
Seasonal Sunroom
Cherry Wood Cabinets, Slate Floors
Wood Fireplace & Bay Window in Dining Room
Kitchen and Dining Room
Wine Cellar, Glass Door
Chilled, Wooden, Wine Room
6 Piece Primary Bathroom
Soaker Tub in Primary Suite
Primary Suite with high Ceilings
Primary Suite. Looks out to Saltwater Pool
Primary Suite. Walk out to Patio w Hottub
Primary Suite Closet
Primary Suite Closet
Lower Level Media Room
5258 Winston Churchill Boulevard photo 36
Basement Space- One of Four Living Rooms
Bedroom #2 with French doors & double closet
Bedroom #4 with double closet & bathroom nextdoor
Main Floor Office
Barn w Paddocks, woodshop & in law suite
Paddocks
Lower Barn
Loft Above Barn
Walk out to beautiful deck
Apartment Kitchen in Barn
3 PC Bathroom in Barn w Standup Shower
Loft Bedroom in Barn
Woodshop in Barn
Veggie Garden Beside Barn and Before The Trails!

5258 Winston Churchill Boulevard

Rural Erin / Erin, ON N0B 1T0

ActiveFor Sale
4 Beds
3 Baths
3,500 Sq Ft
Single Family Home

About This Property

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.

Property Details

StatusActive
Property TypeSingle Family Home
Listing TypeFor Sale
Interior Size3,500 sq ft
Bedrooms4
Bathrooms3
Postal CodeN0B 1T0
Last UpdatedSep 13, 2026 · 10:48 a.m.

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Features & Amenities

  • View
  • Fireplace
  • Air Conditioning
  • Basement

TRREB MLS® Attribution

MLS® X13648806

Listed by ROYAL LEPAGE RCR REALTY

The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$4,599,000

asking price

MLS®X13648806
TypeSingle Family Home
CityErin
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Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$22,458

/month · $3,679,200 mortgage

Down Payment20% — $919,800
Interest Rate5.5%

Amortization

Total Interest

$3,058,057

Total Cost

$6,737,257

Estimate only. Based on Canadian semi-annual compounding, 25-yr amortization at 5.5%.

Full Mortgage Calculator →

Listed By

ROYAL LEPAGE RCR REALTY