5258 Winston Churchill Blvd, Terra Cotta, ON N0B 1T0
About this home
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.
Gas, propane, and electric fireplaces in living and family rooms
Finished basement with sump pump
Kitchen
Oven
Water softener
Heating & cooling
Forced air heating
Wood stove
Propane heating
Central air conditioning
Exterior features
Deck and porch
Pond on the property
Landscaped grounds
Irregular lot
West-facing with views
Security gate
In-ground pool
Home design
Single family detached residence
Residential property
Parking
15 parking spaces total
3 covered spaces
Detached garage with garage door opener
Security
Security gate
Construction
Stone construction
Wood/shake roof
Utilities
Private well water
Septic tank
Sale and tax history for 5258 Winston Churchill Blvd
Sale History
Tax History
Date
Event
Price
TREB #X13648806
Aug 7, 2026
Listed
$4,599,000
TREB #X8185966
Oct 2, 2025
Delisted
—
Feb 13, 2025
Relisted
—
Feb 13, 2025
Price Changed
$4,795,000
Dec 7, 2024
Delisted
—
Nov 1, 2024
Listed
$5,395,000
Nov 1, 2024
Delisted
—
Sep 10, 2024
Price Changed
$5,395,000
Apr 1, 2024
Listed
$5,995,000
+34
Marvellous multi-gen home spans over 5,800 sqft of living space & is brimming with exceptional amenities, set on 25 acres of lush countryside. The 25-acre property is truly breathtaking with secure entry gate, winding driveway leads passed expansive pond to circular drive & 3-car garage that features 2nd floor with 2-piece bath, large closet & spacious office with propane stove. Incredible nearly 4000 sqft 3-level barn with 4 stalls & 5th stall converted to aviary, feed room with sink, spacious living area with kitchen, 3-piece bath, plus generous workshop with propane heater and wood stove. Around the property you find exquisite landscaping & lush gardens, 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. 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. Expansive open-concept conservatory boasts incredible ceiling mural & heated slate flooring that flows into the dining room. Remarkable Muskoka room as well as a secondary foyer with access to in-law suite & 3-piece bath. Upstairs, 2 bright bedrooms plus the magnificent primary bedroom, 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 toilet & 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. 57Cbr Visit This Home's Custom Web Page For a Video Narrated 3D Animated Online Showing, Floor Plans, Pro Photos, and More!
TREB #W1242531
Oct 15, 2007
Listed
$2,285,000
As the MLS and public records start to fill up, we'll list the details here.