5258 WINSTON CHURCHILL BOULEVARD
Rural Erin Erin N0B 1T0

$4,599,000
Single Family beds: 4 baths: 3.0

Welcome to 5258 Winston Churchill Blvd Stay Awhile
Photo 1: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 2: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 3: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 4: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 5: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 6: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 7: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 8: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 9: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 10: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 11: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 12: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 13: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 14: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 15: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 16: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 17: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 18: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 19: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 20: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 21: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 22: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 23: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 24: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 25: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 26: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 27: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 28: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 29: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 30: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 31: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 32: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 33: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 34: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 35: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 36: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 37: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 38: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 39: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 40: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 41: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 42: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 43: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 44: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 45: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 46: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 47: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 48: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 49: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Photo 50: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
Status:
Active
Prop. Type:
Single Family
MLS® Num:
X13648806
Bedrooms:
4
Bathrooms:
3
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. (id:2493)
Property Type:
Single Family
Common Interest:
Freehold
Property Attached:
No
Living Area (Min):
3,500 sq. ft.
Living Area (Max):
5,000 sq. ft.
Taxes:
$13,679 / -
Community:
Rural Erin
Features:
Fireplace(s)
Exterior Features:
Wood, Stone
Pool Features:
Inground pool
Structure Type:
House
Power Type:
Generator
Appliances Included:
Water softener, Oven - Built-In, Garage door opener remote(s), Water Heater
Bedrooms:
4
Bedrooms Above Grade:
4
Bathrooms:
3.0
Half Bathrooms:
1
Cooling:
Central air conditioning
Fireplace:
Yes
Fireplaces:
1
Fireplace Type:
Woodstove
Floor finish:
Hardwood, Slate, Wood
Foundation:
Block
Heating:
Forced air, Propane
Sewer:
Septic System
Basement:
Finished, N/A
Lot Frontage:
352'7¼"
Lot Details:
352.5 FT ; 25.04 acres
Lot Features:
Irregular lot size, Carpet Free, Sump Pump, In-Law Suite, Sauna
Parking:
Detached Garage, Garage
Total Parking Spaces:
15
Floor
Type
Size
Other
Lower level
Other
10'7" × 10'2"
-
Lower level
Living room
20'2" × 10'5"
-
Lower level
Laundry room
19'4½" × 11'8"
-
Ground level
Solarium
21'10" × 17'6½"
-
Ground level
Great room
31'10" × 16'3"
-
Ground level
Sunroom
18'10½" × 18'2"
-
Ground level
Bedroom 4
13'11" × 12'9"
-
Main level
Foyer
13'6" × 12'4"
-
Main level
Office
10'8" × 9'6"
-
Main level
Kitchen
24'5" × 19'10"
-
Upper Level
Primary Bedroom
33'3" × 23'4¾"
-
Upper Level
Bedroom 2
12'11½" × 11'¾"
-
Upper Level
Bedroom 3
13'6" × 9'6"
-
Basement
Media
32'9" × 19'1¾"
-
Basement
Games room
29' × 22'7"
-
Floor
Ensuite
Pieces
Other
Main level
No
-
5'7¼" x 13'1"
Main level
No
-
9'4¾" x 8'6½"
Upper Level
No
-
23'9" x 13'1"
  • Photo 1: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Welcome to 5258 Winston Churchill Blvd Stay Awhile
  • Photo 2: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    House, Buildings, Pond, Land.
  • Photo 3: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Maintained Property Approx 25 Acres
  • Photo 4: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Back Of House & Sunroom
  • Photo 5: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Stone Wall Along Driveway
  • Photo 6: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Composite Back deck W/O From Living Room
  • Photo 7: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Saltwater inground pool
  • Photo 8: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Pool House
  • Photo 9: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Chicken Coop
  • Photo 10: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Bunkie
  • Photo 11: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Sauna
  • Photo 12: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Front Of Home, Beautifully Landscaped
  • Photo 13: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Living Room with Cove Lighting and Large Windows
  • Photo 14: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Sliding doors lead to Composite Backyard Deck
  • Photo 15: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Hand Painted Ceiling Art
  • Photo 16: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Built-in Slate Planters
  • Photo 17: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Dining room with Slate flooring and skylights
  • Photo 18: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Dining Room Looks out to the backyard
  • Photo 19: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Built in Dining Room Bookshelves
  • Photo 20: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Hand Painted Walls
  • Photo 21: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Seasonal Sunroom
  • Photo 22: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Seasonal Sunroom
  • Photo 23: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Cherry Wood Cabinets, Slate Floors
  • Photo 24: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Wood Fireplace & Bay Window in Dining Room
  • Photo 25: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Kitchen and Dining Room
  • Photo 26: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Wine Cellar, Glass Door
  • Photo 27: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Chilled, Wooden, Wine Room
  • Photo 28: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    6 Piece Primary Bathroom
  • Photo 29: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Soaker Tub in Primary Suite
  • Photo 30: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Primary Suite with high Ceilings
  • Photo 31: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Primary Suite. Looks out to Saltwater Pool
  • Photo 32: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Primary Suite. Walk out to Patio w Hottub
  • Photo 33: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Primary Suite Closet
  • Photo 34: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Primary Suite Closet
  • Photo 35: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Lower Level Media Room
  • Photo 36: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Photo 36 of 50
  • Photo 37: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Basement Space- One of Four Living Rooms
  • Photo 38: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Bedroom #2 with French doors & double closet
  • Photo 39: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Bedroom #4 with double closet & bathroom nextdoor
  • Photo 40: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Main Floor Office
  • Photo 41: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Barn w Paddocks, woodshop & in law suite
  • Photo 42: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Paddocks
  • Photo 43: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Lower Barn
  • Photo 44: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Loft Above Barn
  • Photo 45: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Walk out to beautiful deck
  • Photo 46: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Apartment Kitchen in Barn
  • Photo 47: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    3 PC Bathroom in Barn w Standup Shower
  • Photo 48: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Loft Bedroom in Barn
  • Photo 49: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Woodshop in Barn
  • Photo 50: 5258 WINSTON CHURCHILL BOULEVARD in Erin: Single Family for sale : MLS®# X13648806
    Veggie Garden Beside Barn and Before The Trails!
Listed by ROYAL LEPAGE RCR REALTY
Data was last updated September 23, 2026 at 01:45 AM (UTC)
Area Statistics
Listings on market:
67
Avg list price:
$1,990,000
Min list price:
$549,999
Max list price:
$7,600,000
Avg days on market:
59
Min days on market:
1
Max days on market:
490
These statistics are generated based on the current listing's property type and located in Rural Erin. Average values are derived using median calculations. This data is not produced by the MLS® system.
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