5258 Winston Churchill Boulevard
Rural Erin Erin N0B 1T0

$4,599,000
Residential Freehold beds: 4 baths: 3.0

Welcome to 5258 Winston Churchill Blvd Stay Awhile
Photo 1: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 2: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 3: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 4: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 5: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 6: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 7: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 8: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 9: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 10: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 11: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 12: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 13: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 14: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 15: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 16: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 17: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 18: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 19: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 20: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 21: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 22: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 23: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 24: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 25: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 26: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 27: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 28: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 29: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 30: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 31: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 32: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 33: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 34: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 35: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 36: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 37: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 38: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 39: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 40: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 41: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 42: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 43: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 44: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 45: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 46: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 47: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 48: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 49: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Photo 50: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
Status:
Active
Prop. Type:
Residential Freehold
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.
Under Contract:
Propane Tank
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
Backsplit 5
Approx. Age:
51-99
Total Approx Floor Area:
3500-5000
Lot Size:
25-49.99
Lot Depth:
0'
Lot Frontage:
352'6⅛"
Lot Shape:
Irregular
Direction Faces:
West
Bedrooms:
4
Bathrooms:
3.0
Water supply:
Well
Kitchens:
1
Bedrooms Above Grade:
4
Kitchens Above Grade:
1
Rooms Above Grade:
14
Heating type:
Forced Air
Heating Fuel:
Propane
Foundation:
Concrete Block
Roof:
Shake, Cedar
Basement:
Finished
Fireplace Features:
Propane, Electric, Living Room, Family Room, Wood Stove
Fireplace/Stove:
Yes
Garage:
Detached
Garage Spaces:
3.0
Parking Spaces:
10
Total Parking Spaces:
15.0
Farm/Agriculture:
Hobby
Family Room:
Yes
Possession Details:
TBD
Lot Irregularities:
25.04 acres
Pool:
Inground
Link:
No
HST Applicable To Sale Price:
Not Subject to HST
Taxes:
$13,679 / 2026
Assessment:
$- / -
Wellington
Erin
Rural Erin
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
Propane Tanks x3 with Superior
Board & Batten, Stone
Garden, Forest, Pond, Trees/Woods
Public Road
Pond
Floor
Type
Size
Other
Upper
Primary Bedroom
33'3" × 23'4¾"
W/O To Porch, Walk-In Closet(s), Overlooks Pool
Upper
Bedroom 2
12'11½" × 11'¾"
Double Closet, French Doors, Crown Moulding
Upper
Bedroom 3
13'6" × 9'6"
Hardwood Floor, Closet
Main
Office
10'8" × 9'6"
B/I Bookcase, French Doors, Overlooks Backyard
Main
Kitchen
24'5" × 19'10"
Combined w/Dining, Slate Flooring, Fireplace
Ground
Solarium
21'10" × 17'6½"
Slate Flooring, Skylight, Fireplace
Ground
Great Room
31'10" × 16'3"
Vaulted Ceiling(s), Walk-Out, W/O To Deck
Ground
Sunroom
18'10½" × 18'2"
Stone Floor, Sliding Doors, Wood
Ground
Bedroom 4
13'11" × 12'9"
Double Closet, Overlooks Frontyard
Lower
Other
10'7" × 10'2"
Glass Doors, Wood
Lower
Living Room
20'2" × 10'5"
B/I Closet
Basement
Media Room
32'9" × 19'1¾"
B/I Bookcase, Pot Lights, Built-in Speakers
Lower
Laundry
19'4½" × 11'8"
Laundry Sink
Basement
Game Room
29' × 22'7"
Electric Fireplace, Stone Floor, B/I Bookcase
Main
Foyer
13'6" × 12'4"
Wainscoting
Floor
Ensuite
Pieces
Other
Upper
Yes
6
23'9" x 13'1" 6 Pc Ensuite, Overlooks Backyard, Double Sink
Main
No
2
5'7¼" x 13'1" 2 Pc Bath
Main
No
3
9'4¾" x 8'6½" Slate Flooring, Crown Moulding, 3 Pc Bath
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Laundry Level:
Main Level
Date Listed:
Aug 07, 2026
  • Photo 1: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Welcome to 5258 Winston Churchill Blvd Stay Awhile
  • Photo 2: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    House, Buildings, Pond, Land.
  • Photo 3: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Maintained Property Approx 25 Acres
  • Photo 4: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Back Of House & Sunroom
  • Photo 5: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Stone Wall Along Driveway
  • Photo 6: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Composite Back deck W/O From Living Room
  • Photo 7: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Saltwater inground pool
  • Photo 8: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Pool House
  • Photo 9: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Chicken Coop
  • Photo 10: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Bunkie
  • Photo 11: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Sauna
  • Photo 12: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Front Of Home, Beautifully Landscaped
  • Photo 13: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Living Room with Cove Lighting and Large Windows
  • Photo 14: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Sliding doors lead to Composite Backyard Deck
  • Photo 15: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Hand Painted Ceiling Art
  • Photo 16: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Built-in Slate Planters
  • Photo 17: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Dining room with Slate flooring and skylights
  • Photo 18: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Dining Room Looks out to the backyard
  • Photo 19: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Built in Dining Room Bookshelves
  • Photo 20: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Hand Painted Walls
  • Photo 21: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Seasonal Sunroom
  • Photo 22: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Seasonal Sunroom
  • Photo 23: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Cherry Wood Cabinets, Slate Floors
  • Photo 24: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Wood Fireplace & Bay Window in Dining Room
  • Photo 25: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Kitchen and Dining Room
  • Photo 26: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Wine Cellar, Glass Door
  • Photo 27: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Chilled, Wooden, Wine Room
  • Photo 28: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    6 Piece Primary Bathroom
  • Photo 29: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Soaker Tub in Primary Suite
  • Photo 30: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Primary Suite with high Ceilings
  • Photo 31: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Primary Suite. Looks out to Saltwater Pool
  • Photo 32: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Primary Suite. Walk out to Patio w Hottub
  • Photo 33: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Primary Suite Closet
  • Photo 34: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Primary Suite Closet
  • Photo 35: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Lower Level Media Room
  • Photo 36: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Photo 36 of 50
  • Photo 37: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Basement Space- One of Four Living Rooms
  • Photo 38: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Bedroom #2 with French doors & double closet
  • Photo 39: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Bedroom #4 with double closet & bathroom nextdoor
  • Photo 40: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Main Floor Office
  • Photo 41: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Barn w Paddocks, woodshop & in law suite
  • Photo 42: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Paddocks
  • Photo 43: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Lower Barn
  • Photo 44: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Loft Above Barn
  • Photo 45: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Walk out to beautiful deck
  • Photo 46: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Apartment Kitchen in Barn
  • Photo 47: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    3 PC Bathroom in Barn w Standup Shower
  • Photo 48: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Loft Bedroom in Barn
  • Photo 49: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Woodshop in Barn
  • Photo 50: 5258 Winston Churchill Boulevard in Erin: Rural Erin House for sale : MLS®# X13648806
    Veggie Garden Beside Barn and Before The Trails!
Listed by ROYAL LEPAGE RCR REALTY
Data was last updated August 10, 2026 at 12:15 PM (UTC)
Area Statistics
Listings on market:
82
Avg list price:
$1,799,450
Min list price:
$549,999
Max list price:
$7,250,000
Avg days on market:
51
Min days on market:
2
Max days on market:
699
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.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.