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Kevin Flaherty, top 1% Orangeville realtor for 10+ years, providing free no-obligation home value opinions — call 226-270-6433

5258 Winston Churchill Blvd, Erin

Stunning backyard oasis featuring a sparkling pool surrounded by lush greenery and landscaped gardens at 5258 Winston Churchill Blvd, Erin.
Grand open concept main level featuring large windows, elegant decor, and natural light, showcasing a spacious living area with plants, seating, and dining space.
Primary bedroom featuring large windows with scenic views, hardwood flooring, and cozy decor, emphasizing luxury and comfort in a real estate listing.
Upgraded 5-piece ensuite washroom featuring a luxurious bathtub, marble countertops, wooden cabinetry, and large windows with views of the surrounding landscape.

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House Interior

Floor Plans

Main level floor plan of a luxury multi-generational home, featuring an open layout with kitchen, living areas, and detailed room descriptions, emphasizing spaciousness and amenities.
Lower level floor plan of luxury home featuring spacious living areas, kitchen layout, and detailed room dimensions for real estate listing.
Main level floor plan of luxury home at 5258 Winston Churchill Blvd, featuring primary bedroom, ensuite, kitchen, dining room, and conservatory, totaling 3,935 sq. ft.
Lower level floor plan of 5258 Winston Churchill Blvd, featuring a billiards area, theatre area, sitting area, wine cellar, large recreation room, laundry room, and utilities, with a total square footage of 1,908 sq. ft.

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MLS® #: X8185966

PRICE: $4,795,000.00

STATUS: AVAILABLE

This marvellous multi-generational home spans over 5,800 square feet of living space and is brimming with exceptional amenities, set on 25 acres of lush countryside.


The 25-acre property itself is truly breathtaking with secure entry gate, winding driveway that leads passed an expansive pond to the circular drive & 3-car garage that features a 2nd floor with 2-piece bath, large closet & spacious office with propane stove. An incredible nearly 4000 sqft 3-level barn with 4 stalls with a 5th stall converted to an aviary, feed room with sink, spacious living area with kitchen and 3-piece bath, plus generous workshop with propane heater and wood stove. Around the property you will find exquisite landscaping & lush gardens, a large drive shed, multiple paddocks, vegetable garden & fruit trees, water hydrants, chicken coop with sugar shack, cabana with shower & sauna, gazebo, fire pit, ample patio space surrounding the in-ground heated saltwater pool plus deck with access to the conservatory.


An extended covered front porch welcome you into the foyer where you will find a 2-piece bath & stunning office. Extraordinary eat-in kitchen features cherry cabinetry and spacious island, plus wood fireplace & large bay window. The expansive open-concept conservatory boasts incredible ceiling mural & heated slate flooring that flows into the dining room. A remarkable Muskoka room as well as a secondary foyer with access to an in-law suite & 3-piece bath.


Up the stairs, 2 incredible bright bedrooms plus the magnificent primary bedrooms, complimented by a circular bank of windows, a sliding door walkout to the hot tub, generous closet with custom built cherry wardrobe & central island, plus stunning ensuite with soaking tub, custom dual sink vanity, walk-in shower with heat lamp & towel rack, plus water closet with bidet.


Down the steps you find the home’s temperature controlled wine cellar, an expansive home theatre & billiards room, a spacious laundry/kitchen space, a recreation space with built-in media unit & additional cabinetry, plus so much more.


If you have any questions or would like to book a showing please call Kevin Flaherty directly at 226-773-1970.

LOCATION DETAILS

Address:

5258 Winston Churchill Blvd, Erin

Legal Description:

CON 11 E PT LOT 9 RP 61R1019 PT PART 2

Fronting On:

West Side

Lot Front:

352.53 Ft.

Lot Size:

25.04 Acres

AMOUNTS/DATES

List Price:
$5,395,000.00

Taxes/Year:

$12,480.27 / 2023

Possession Date

To be arranged

EXTERIOR

Type:
Detached

Style:
5 Level Sidesplit

Exterior:

Board & Batten / Stone

Garage Type/Spaces:
Detached / 3

Drive Type/Spaces:
Private - Circular / 20 + Spaces

Pool:
Inground

Water:
Well

Sewers:
Septic

Approx. Age:
51-99 Years

Approx. Square Footage:
3935 + 1908 Sqft

Other Structures:
Barn & Drive Shed

INTERIOR

Bedrooms:
4

Bathrooms:
1 - 6 Piece Upper/1 - 3 Piece & 1 - 2 Piece Main

Kitchens:
1

Basements:
Full - Finished

Heat Source:
Propane

Heat Type:
Forced Air

Air Conditioning:
Central Air

Central Vacuum:
Yes

Laundry Level:
Main - Middle

UTILITIES

Hydro:
Yes

Sewers:
No

Gas (Natural):
No

Municipal Water:
No

Rental Items:

Propane Tank x 3

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House Exterior & Outbuilding

Photos

House Exterior & Outbuilding

Garage Floor Plans

Garage floor plan for property at 5258 Winston Churchill Blvd, featuring dimensions for a large 3-car garage, total square footage of 964, and labeled areas for access and storage.
Garage upper level floor plan for 5258 Winston Churchill Blvd, featuring a large executive office, 2-piece bath, wood stove, and closet, with dimensions and scale indicated.

Barn

Photos

Barn

Floor Plans

Floor plan of a barn at 5258 Winston Churchill Blvd, featuring multiple stalls, aviary, foyer, and milk room, with dimensions and square footage noted.
Barn loft level floor plan for property at 5258 Winston Churchill Blvd, featuring loft bedroom, workshop, and storage areas, with dimensions and scale indicated.

Area Maps

Aerial view of a 25-acre property with outlined boundaries, surrounded by colorful fall foliage, ponds, and residential homes, emphasizing real estate potential at 5258 Winston Churchill Blvd, Erin.
Map highlighting the location of 5258 Winston Churchill Blvd in Erin, showing nearby landmarks like Robert Baker Forest, Erin Heights Golf Course, and distances to Georgetown and Cheltenham.
Map highlighting the location of 5258 Winston Churchill Blvd in Erin, Ontario, with nearby cities and landmarks labeled.

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