17353 Winston Churchill Boulevard
Rural Caledon, Caledon, L7K 1N1
FOR SALE
$2,700,000
➧
➧


Browsing Limit Reached
Please Register for Unlimited Access
4
BEDROOMS 5
BATHROOMS 1
KITCHENS 10
ROOMS W14167074
MLSID Contact Us
Property Description
A custom country retreat in the heart of Terra Cotta. Welcome to 17353 Winston Churchik Boulevard, Caledon, where over 4,000 sq. ft. of living space sits on an approximately 2-acre lot backing onto 15 acres of Crown land. A double-door entry welcomes you to a spacious main f!oor with distinct living, dining, and family rooms, plus a dedicated office or den. The upgraded kitchen features a generous eat-in area with a walkout to a balcony overlooking the natural landscape, an inviting spot for morning coffee or dinner outdoors. Upstairs, you'll find four bedrooms and three full bathrooms, while the finished walkout basement adds a fifth bedroom and an open-concept living area ideal for guests, recreation, or extended family. A three-car garage and driveway parking for more than 10 vehicles make hosting easy. Just minutes from Erin and Belfountain, this custom home offers the space to entertain and the quiet to unwind.
Call
Sold History
| List Date | Sold Date | Days Listed | List Price | Sold Price |
|---|---|---|---|---|
| 2016-01-26 | 2016-02-19 | 24 | $898,000 | $850,000 |
| 2011-10-07 | 2011-11-04 | 28 | $645,000 | $622,000 |
| 2008-03-31 | 2008-08-26 | 148 | $615,000 | $590,000 |
Property Features
None, Private
Call
Property Details
Address
17353 Winston Churchill Boulevard
Community
City
Postal Code
L7K 1N1
Property Type
Detached, Detached
Lot Size
279' x 377'
Taxes
$9,438 (2025
Basement
Finished with Walk-Out
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Parking Spaces
10
Garage Type
Attached
Call
Listing contracted with Re/Max President Realty
Similar Listings
Experience exceptional space, privacy, and natural beauty in this impressive 2-storey residence set on approximately 1.62 acres in the sought-after Palgrave community. Offering approximately 4,758 sq. ft. of living space, this expansive home features 4 bedrooms, 5 bathrooms, a family room, and a 3-car attached garage with ample private driveway parking. Enjoy beautiful clear views surrounded by greenbelt and ravine landscapes, creating a peaceful and picturesque setting. Built to white-wall stage, the property includes the septic system, HVAC, plumbing for water, electrical, drywall, and insulation beneath the basement floor, providing an excellent opportunity to complete the interior to your own taste and specifications. A rare opportunity to create a truly customized luxury home in a serene countryside setting, while remaining conveniently connected to the amenities and communities of Caledon.
Call
Set amidst 25 acres of serene, wooded landscape backing onto conservation land, this exceptional raised bungalow offers over 5,800 sq. ft. of refined living space in an extraordinarily private setting. Surrounded by towering trees and breathtaking natural views, the home seamlessly blends elegance, comfort, and resort style living. Designed for both everyday living and grand entertaining, the main level features a spacious living room with a wood-burning marble fireplace, soaring cathedral ceilings, and an effortless flow into the formal dining room and expansive kitchen complete with centre island, granite flooring, and walkout to an oversized patio and enclosed gazebo pavilion. Thermal windows throughout the home showcase spectacular views of the surrounding property. Hardwood flooring, a grand marble foyer, and generously sized bedrooms further elevate the home's timeless appeal. The fully finished lower level is an entertainer's dream, featuring a stunning flagstone wet bar open to an expansive family room with marble fireplace, dedicated spa room with sauna, hot tub, change rooms with shower. An ideal in-law or multi-generational living setup.
Call
Stop searching for your dream home-this is the one! Situated on a premium 1+ acre lot, this stunning custom-built bungalow showcases exceptional craftsmanship and luxury upgrades throughout. A grand foyer with over 12-foot ceilings and double-door entry welcomes you into elegant living and dining spaces featuring coffered ceilings and recessed lighting. The impressive family room boasts soaring 14-foot ceilings with cove lighting, while the chef-inspired kitchen is equipped with premium appliances, a gas range, oversized panel-ready fridge and dishwasher, servery, full pantry, oversized island, and abundant cabinetry. Large windows with custom blinds flood the home with natural light. The luxurious primary suite offers a custom walk-in closet and spa-like ensuite with a designer tub, towel warmer, and glass shower, while a second primary bedroom includes its own private ensuite. The thoughtfully designed mudroom features custom cabinetry, shoe storage, and a built-in bench. The walk-out basement provides an incredible opportunity to add approximately 3000 sq. ft. of additional living space and is already partially completed with drywall, electrical, plumbing, and heated floor rough-ins. Planned for 9-foot ceilings, a full kitchen, living area, two bedrooms, theatre room, gym, sauna, and two bathrooms, this remarkable home is built far above standard code requirements and offers the perfect blend of luxury, comfort, and future potential.
Call
Welcome to this incredible meticulously kept and built residence (2005) situated on a sprawling, private 1-acre lot! Offering unmatched versatility, the main level features 3 spacious bedrooms and bright living areas, while the lower level boasts a fully self-contained 2-bedroom basement apartment with a dedicated separate entrance, private deck, and direct access from a separate attached garage-ideal for multigenerational living or rental income. A total of 4 bathrooms provides ultimate convenience throughout. Hobbyists, car enthusiasts, and trade professionals will be blown away by the detached 3-car garage/shop equipped with a vehicle hoist! This mechanically sound property offers complete peace of mind with continuous upgrades and high-end infrastructure, including an 18 kW Generac generator, brand-new owned hot water tank (2026), A/C and furnace (2017), 50-year roof shingles on the house (2017) and shop (2018), water softener, water purification system, central vacuum, irrigation system, security system, and customizable Gemstone exterior lighting. A rare package offering endless potential, privacy, and mechanical excellence!
Call
Experience the perfect balance of luxury, nature, and convenience. This property will appeal to the discerning buyer seeking something truly special. Inside 6,500 square feet of thoughtfully blends open-concept living with cozy private retreats. Nestled on a unique, secluded 1.88-acre lot, this is not just another estate - it's an exclusive haven waiting to be yours. Bask in natural light in the stunning 2-story great room flowing seamlessly into the well appointed kitchen that offers space for multiple cooks and seamless entertaining. The 2nd story primary suite is a private retreat, complete with a luxurious five-piece ensuite and a massive walk-in closet. Two additional bedrooms on this floor each feature their own ensuite baths and walk-in closets, ensuring comfort and privacy for family or guests. A fourth bedroom, conveniently located on the main floor, offers its own adjacent 3-piece bath. Need more flexibility? Two main-floor offices provide ideal work-from-home setups or creative spaces. The fully finished walk-up basement is a world of possibilities. With a second kitchen, exercise room, media room, 2-piece bath, and ample storage, it's ready to be transformed into the ultimate entertainment space or in-law suite. Outside is your private paradise, where the lush yard and pool are surrounded by mature trees, offering complete tranquility. A sweeping drive and 3-car garage in the front. An outdoor living space tailored for unforgettable gatherings, featuring an inground pool, a cabana with a 2-piece bath, expansive patios, and deck areas for dining, lounging, and family fun in the back. Beyond the property, the Caledon Trailway, Credit River and the quaint village of Cheltenham are nearby, or explore local gems like Terra Cotta and Belfountain. With Pearson Airport only 30 minutes and downtown Toronto an hour's drive, this property offers countryside living without compromise.
Call
Beautiful Bungalow with amazing views! A rare find, this custom built home in the sought-after Cheltenham community offers 3200sq ft upstairs and another 2690 sq ft downstairs, has soaring ceilings and windows in the sunken living room and master suite, hardwood floors, very large spacious rooms, a huge exercise room and tons of storage. There are 4 bedrooms upstairs with 2 full baths and 1 powder room. The custom kitchen has granite counters with tons of cabinets for storage, 2 sinks and spectacular views of both the front and back.The finished lower level offers separate access to an apartment with 2 large bedrooms, 1.5 baths, including it's own laundry and walk out to private patio, perfect for in-laws or rental income. The exercise room has separate access from the Main and Lower level. A standout feature is the expansive upper-level deck spanning nearly the entire width of the home, offering stunning views of the backyard. Accessible from the kitchen or the master suite, it's the perfect spot to enjoy your morning coffee or unwind while taking in the peaceful, natural surroundings. The property boasts 1.1 acres of lush grounds, with a 3-car garage plus an additional backyard workshop ideal for toys, landscape equipment & hobbies as well as a separate garden shed. Lush perennial flower gardens surround the house and an established vegetable garden is ready for your green thumb. A fully fenced pool completes this property on a quiet road with limited traffic. Just minutes from Brampton, the Pulpit Golf Club, Caledon Ski Club, and walking distance to the General Store, Credit River and Caledon Trail way. Surrounded by farm fields with a gorgeous view of the Escarpment, this property is perfect for those seeking tranquillity with the convenience of city life just a short drive away. Pearson Airport is a quick 30-minute drive. Some furnishings available for sale.
Call
Welcome to a one-of-a-kind longevity estate where nature, privacy & wellness-focused design converge on 2.71 picturesque acres. Ideally located near the Pulpit Club, Caledon Mountain Trout Club, Caledon Ski Club, Brampton Flying Club & Bruce Trail, this extraordinary property offers a private sanctuary just minutes from the city. Designed around health, recovery & connection, the grounds create an immersive outdoor wellness experience. Enjoy an inground saltwater pool, cold plunge, open-air shower, extensive grounding trails & curated gardens. A wood-fired pizza oven, outdoor bar, firepit, pool cabana, charming children's playhouse/bunkie & 3 decks provide multiple spaces to relax, entertain & connect. Inside, expansive windows bring abundant natural light & frame the surrounding landscape. The modern kitchen features marble countertops, stainless steel appliances & a striking backsplash, flowing into the dining area. The living room offers a stunning brick accent wall & wood-burning fireplace, while the bright home office w/ built-in desk & outdoor access provides an inspiring space for focused work. The main-floor primary suite is a tranquil retreat w/ luxurious 4-pc ensuite & walk-in shower. Upstairs, 3 spacious bedrooms & 2 well-appointed baths offer comfortable accommodations for family & guests. The 3rd-floor loft is a private wellness sanctuary featuring an infrared sauna & custom-built sauna. Additional highlights include heated marble bathroom floors, new hardwood flooring & a custom floor-to-ceiling glass wine cellar. For added comfort & peace of mind, the home features a backup generator, advanced air-quality systems, whole-home water treatment & major electrical upgrades.Elegant, modern & immersed in nature, 2814 Forks of the Credit Road is more than a home. It is a distinctive retreat designed for living, entertaining, recharging & enjoying life to its fullest.
Call
Car enthusiasts/Hobbyists take a look at this! Almost 5,000 square feet of secure and monitored garage storage spanning across 3 out buildings! Likely not be to recreated in today's world. The potential is endless; storage, workshop, yoga/art studio, gym, must be seen to be appreciated. Set minutes from Bolton on a mature 3 acre lot, this lovely bungalow offers 3 bedrooms on the main and 3 in the lower with full walk-out. Cathedral ceilings, family sized Kitchen, walk-out to amazing deck perfect for dining alfresco or enjoying a summers day. An additional attached 2 car garage enters directly into the house. Access to the best Public, Separate and Private Schools, Golf, Equestrian, Community Centres, Trails, Airport and easy commute to the city. A rare offering. Garage #1: 34'9"x23'3". Garage #2: 58'4" x 38'5" with a storage room, roughed-in bath and loft. Garage #3: 59'1" x 31'2" has accommodated up to 12 cars
Call
One Of Caledon's Most Scenic, Stunning Properties. Set Privately, Bordered By Mature Trees & Forest Yet Open To The 28 Acres Of Rolling Hills & Trails. Natural Vistas And Glorious Sunsets. The Home Features Large, Grand Principal Rooms, Walk Outs And A Beautiful Outdoor Hub With Inground Pool, Bunkhouse With 3 Pc Washroom, Fire Pit & Covered Lounge/Dining. A Heated Out Building With A Workshop & Stalls. Separate Garage Attached. Irrigation Posts Strategically Placed. Floor Plans Attached - Pls Note The Primary Bedroom & Ensuite And Bedroom & 4 Piece Not Shown On Plans.
Call
Luxury Executive Detached Estate Home In Prestigious Osprey Mills on 3/4 Acre CORNER Lot, 4331 Sq.ft. Of Above Ground Featuring 10'+ Ceilings on Main Floor,9' Basement & 2nd Floor. Engineered Hardwood Flooring and Quartz Counters Throughout. See Schedule For Standard Features & Finishes and Floorplan. Home is For Sale by Builder. Purchaser to sign Builder APS and Responsible for All Closing Costs. Taxes Not Assessed. RENT TO OWN PROGRAM AVAILABLE.
Call
Discover space, privacy, and timeless curb appeal at 79 Amos Drive, set on 2.3 acres in one of Palgrave's sought-after estate neighbourhoods. Surrounded by mature trees and expansive properties, this impressive stone-and-stucco residence offers a peaceful setting with room to breathe. A grand entrance welcomes you into a thoughtfully designed layout with inviting spaces for entertaining and everyday family living. Large windows draw in natural light and frame views of the surrounding greenery, connecting the home to its beautiful setting. From gatherings with friends to quiet evenings at home, the residence offers a comfortable balance of elegance and warmth. Outside, manicured grounds and the generous acreage create space to relax, gather, and enjoy the outdoors. Experience the privacy and sense of retreat that define estate living, with convenient access to local schools, trails, and Caledon amenities.
Call
Luxurious Caledon escape awaits in this executive home. Refined country living meets exceptional convenience. Set on2beautifully groomed acres with private pond, this expansive, lovingly maintained bungalow offers an extraordinary lifestyle so close to the city. From the moment you arrive, the setting is impressive, yet it is what's inside that truly sets this home apart. With over 7,500sf of bright, stunning space, this remarkable residence features 4 king-sized bdrms, 3.5 marble & stone baths, indoor heated pool, sun-filled gym/yoga room, &floor-to-ceiling windows showcasing sweeping views of the lush grounds & 2 stone patios.Designed for both effortless living & unforgettable entertaining.The main floor offers one-level living, private office, double-sided fireplaces,2 formal living spaces one includes an impressive20' cathedral ceiling ideal for billiards, entertaining, or enjoying the grandeur of the space.The expansive kitchen is equally impressive, with granite countertops,raised bar,48"stainless fridge/freezer,double wall ovens,&walk-in pantry,all open to a generous breakfast area&peaceful solarium overlooking the tranquil landscape. Truly fit for a King!Adding to the property's extraordinary story, the Duke of Kent, Queen Elizabeth II's cousin, once called this estate home during a stay in the 1990s,reportedly enjoying breakfast&afternoon tea daily in the home's gorgeous solariums.Approached by an oversized stone driveway with ample parking,the property offers 3-car garage&convenient mudroom separate from the main-floor laundry.Imagine the freedom of having your own private retreat to swim/exercise/entertain/unwind year-round, even skate/hockey in winter without memberships,commuting,or giving up GTA amenities. Inglewood offers the best of both worlds:Peaceful rural setting,yet connected to Orangeville, Brampton & Hwy 410. A truly remarkable property!An unforgettable setting!A home with a story to tell!Come experience it. You have to see it to believe it!
Call
An exceptional opportunity to complete and customize your dream estate in the prestigious Palgrave community of Caledon. Situated on a spectacular approx 1.495-acre lot surrounded by executive homes and natural beauty, this impressive 4,237 sq. ft. two-storey residence is currently under construction and fully framed, offering the perfect canvas to bring your vision to life.The home has already undergone significant progress, including completed framing, septic installation, and electrical rough-ins. Designed with a spacious and functional layout, the plans feature 4 bedrooms with ensuite bathrooms & W/I closets & generous principal rooms, and an unfinished basement ready for future customization.Enjoy the tranquility of country living with the convenience of municipal water and available services, all within one of Caledon's most sought-after estate neighbourhoods. Surrounded by conservation lands and scenic views, this rare offering provides the opportunity to personalize finishes and complete a custom home tailored to your lifestyle.A unique chance for builders, investors, or end-users to acquire a premium estate lot with substantial construction already in place in an exclusive Palgrave location.
Call
**Excellent opportunity** to acquire 10.45 acres in a prime location of Caledon offering endless possibilities, located close to King St and The Gore Rd. This spacious raised bungalow features 2146 sq. ft. of well-designed living space with 4 generous bedrooms and 3 bathrooms.The bright main level offers an open-concept layout with a country-style kitchen overlooking the family room, expansive living and dining areas, and spacious bedrooms. The fully finished walk-out basement includes its own kitchen, washroom, 2 additional bedrooms, and a large recreation area, making it ideal for extended family, multi-generational living, or potential income opportunities. Also, 2000 Sq Ft Barn with 2 large drive in doors. Surrounded by picturesque countryside while remaining conveniently close to major roads and everyday amenities, this exceptional property combines privacy, space, and outstanding future potential. Whether you're looking for a family estate or investment opportunity, this unique Caledon property is one you won't want to miss.
Call
Welcome to this beautiful home in Caledon, offering approximately 2,700 sqft of thoughtfullydesigned living space. Nestled on a fully fenced lot near the city, this residence features astriking blend of brick and stone construction. Inside, you'll find a spacious layout withfour bedrooms, with an additional two bedrooms in the finished basement. The basement includesa separate entrance, perfect for extended family or guests. The main floor is enhanced withnew kitchen upgrades, elegant porcelain tiles, and a vaulted ceiling in the living room, wherea cozy wood-burning fireplace awaits. The home also includes a unique loft space behind thegarage for extra storage. This stunning home also boasts an impressive 21 parking spaces!Whether you're hosting gatherings, have multiple vehicles, or need ample space for RVs andguests, this property has you covered. The expansive driveway and dedicated parking areaprovide unmatched convenience and flexibility for your lifestyle. Enjoy the peace of mind thatcomes with having plenty of room for everyone and everything. This home truly offers the bestin comfort and practicality don't miss out on this one-of-a-kind opportunity!
Call
Call