2049 Highpoint Side Road

Here is your opportunity to acquire 2 houses on 52 acres in Caledon. AAA location near Bolton and Nobleton. Long views over the majestic Caledon Hills. The main residence has 3 finished levels including a bright lower level walk-out to the pool and patio. The long extended paved driveway leads to the 2nd residence. A barn with office and loads of storage space and even a meeting room and basketball court is just past the 2nd residence. Down by the pond is a sand volleyball court and beach with tiki hut. Miles of walking, ATV trails. Spring-fed pond with dock and beach. Potential for main floor bedroom alongside existing full bathroom. Large main floor office plus a wonderful open floor plan which joins the kitchen, breakfast room, family room and large dining room. The finished lower level could be further developed into a separate suite with existing bedroom, existing bathroom and large existing finished living area and bar. New propane furnace (2026). Value priced for today's market!

Welcome to Cedar Drive one of Caledon's most sought after estate style residential developments. Frank Lloyd Wright inspired, this Executive Style Bungaloft Is Perfect For The Outdoor Enthusiast who also loves Entertaining. Newly renovated kitchen with Cambria Quartz counters, built-in Wolf & Sub Zero Appliances. Heated with Natural Gas and fully wired with Fiber Hi-Speed Internet. The east wing is perfect for the successful individual with the option to Work From Home with your own separate access Home Office. All bedrooms are ensuite. 5.47 Acres Of Excellence! Enjoy the Views of this Hardwood Forested Property With 3/4 Acre Fully Stocked Pond. Take advantage of the 1.8 acre tax incentive program. Monitored security system, 2 EV Chargers, predictive automated irrigation system, 22kw Generac generator with remote monitoring - 3 fireplaces including 1 wood-burning, 3 car garage. ****All of this and more just an easy commute to Toronto! **EXTRAS** Just a hop skip & a jump to the Caledon Trail System and Provincial Park & Conservation Park. A chip & a put to the Caledon Country Club, Devils Pulpit Association and Osprey TPC Courses, a Cast away from the Caledon Trout Club.

Exceptional Opportunity for Buyers & Investors! Set on an expansive 10-acre parcel, this unique beautiful property features a cozy 3+1 Bedroom detached home with Finished Basement** Offers tremendous potential for future growth and investment** Ideally located near Healey Road and in proximity to the proposed Highway 413 corridor, offering excellent future connectivity and long-term investment potential** Perfect for long-term investment, agricultural use, or building your custom dream estate. The land includes productive farmland with mature apple trees, adding both charm and value** A rare offering-don't miss this opportunity to secure a prime piece of land with endless possibilities.

Discover the perfect blend of luxury and convenience with this stunning property that featuresTWO separate homes within the property. This property is ideal for a family that care to havetheir immediate family nearby. This dream home is nestled in the serene surroundings of Caledon, and is located in the beautiful Terra-Cotta Caledon. This property is perfect forthose seeking tranquillity with the convenience of city life just a short drive away from the city. These picturesque views from this immaculate four-bedroom home have a peaceful and private40 acre lot, with towering and mature trees in a gorgeous wildflower Garden. Relax and unwindwhile listening to the sound of nature, whether on the main deck or the second deck that hasaccess from the kitchen with a beautiful, breathtaking view. The second floor is overlooking thestunning tall trees filled with nature and a beautiful panoramic view thatyou just won't want to leave. The living rooms of her beautiful ash masonry from all anglesof the house, not to mention the fireplace in the master room. The Eden kitchen features a skylight and floor-to-ceiling windows from both sides overlooking the backyard and wildlifeenjoying the second home that is featured on this property and is renovated from top to bottom. The second one includes a meeting with a board room a bathroom a full bathroom, and a kitchenand not to mention the beautiful surrounding nature around the second house as well. Wildlifeabounds with birds, turkeys, and deer come for a visit and you will not want to leave the home.This property is managed to conservation area skiing, luxury God, is on a spa resort 45 minutes to Pearson airport. This property comes with gated entry. Both homes have separate meters. Hur ryand make this your dream home.

Stunning Restored Victorian Farmhouse on 57 Private Acres with Barn & Trails Originally built in 1860 by the McEachern family, this Grand Victorian farmhouse has been beautifully restored, blending timeless craftsmanship with modern comfort. Privately set on 57acres, this rare country retreat features high ceilings, original stonework, hardwood and tile flooring, and countless preserved architectural details including limestone windowsills, gingerbread trim, and a dramatic spiral wood staircase. The spacious 3-bedroom home features an updated open-concept kitchen that flows seamlessly into a large dining area ideal for family gatherings and entertaining. The sun-filled living room is accented with original plaster crown molding and oversized windows that frame views of the garden. The luxurious primary suite offers a spa-like ensuite bath and a huge walk-in closet. Nearly every window offers a postcard-worthy view whether overlooking the historic stone ice house(which could serve as a studio or workshop), the Mennonite-restored bank barn, the fenced paddocks, vegetable gardens, or open meadows. Equestrian-ready, the bank barn features 5 stalls, a wash stall, tack room, and spacious hayloft. There's also a large heated workshop for hobbies or home business use. The land is enrolled in a managed forest program for significant tax savings, and private trails invite riding, hiking, mountain biking, and exploring. Located on a quiet country road just minutes from Caledon amenities, near the GO Train, and within easy commuting distance to the city. Live the country dream with all the comforts of modern living and the beauty of historic charm.

Stunning Stone Bungaloft On Over 9 Acres Of Mature Forest W/ 6 Car Garage. Cust. Crafted W/ Loads Of Character, Dramatic 20' Post & Beam Ceiling. Cust. Kit With S/S Appl, Dbl Oven & Indoor Bbq. 3 Bdrms All With Ensuite (Loft Can be 4th Bdrm). Designed With Both Style And Comfort In Mind. This Is More Than a Home It's a Lifestyle Opportunity You Won't Want To Miss.

Set on approximately 15.8 acres this exceptional opportunity to acquire a distinctive, income-producing multi-residential estate in the heart of scenic Caledon. Seamlessly combining rural charm with strong investment potential, this remarkable property features 3 self-contained residential units, a detached barn, and picturesque countryside views-all located within an hour of Toronto. Ideally suited for multi-generational living, savvy investors, or those seeking a private lifestyle retreat or hobby farm, the property offers outstanding versatility and long-term value. The 4-stall barn presents endless possibilities for equestrian use, workshop space, storage, or an agri-focused lifestyle. Each residence is thoughtfully designed with its own private entrance, generous parking, and modern updates throughout, providing both comfort and independence for occupants. Enjoy the convenience of nearby amenities including hiking trails, equestrian facilities, golf courses, and local markets, along with easy access to Highways 400, 427, and 407. The grounds showcase a gated entry, a tree-lined driveway, mature landscaping, perennial gardens, and multiple outdoor living spaces including a pergola, gazebo, and expansive decks-perfect for relaxing or entertaining. Additional features include two wells, two septic systems, a 10kW auto-start backup generator, and fiber-optic internet service via Vianet to both dwellings. Recent upgrades include new roofs and windows on both homes, updated furnace and air conditioning systems, attic insulation in the main residence, and a mini-split heat pump in the guest house. A rare offering in one of Caledon's most desirable rural enclaves-move in, invest, or create your ideal country lifestyle.

Exquisite 2-storey estate home offering approximately 4,000 sq. ft. on the main and second levels, located in the prestigious Millcreek Estates and gracefully set on a breathtaking 2.74 acre lot within a serene and private Caledon enclave. This stunning 4+1 bedroom residence showcases refined elegance and superior craftsmanship, featuring rich hardwood flooring, crown moulding, oversized baseboards, designer lighting, pot lights, and soaring 10-ft ceilings throughout. A striking grand foyer welcomes you into beautifully appointed principal rooms, including a sophisticated formal dining room perfect for entertaining. The impressive living room features floor-to-ceiling windows, a fireplace, and a walk-out to the expansive upper deck overlooking lush, picturesque greenspace-your own private retreat. The chef-inspired gourmet kitchen is both stylish and functional, offering premium built-in appliances, a gas stove, oversized centre island with breakfast bar, and a bright breakfast area with walk-out access. The adjoining family room with fireplace provides a warm, inviting space with serene backyard views. The main-level primary suite is a luxurious retreat with walk-out access, a spa-like 5-piece ensuite, and his & hers walk-in closets. Additional conveniences include a well-designed mudroom with built-in cabinetry and separate entrance, direct garage access, and a spacious laundry room. Upstairs, three generously sized bedrooms each feature private ensuites; two offer walk-in closets, while the third provides a double closet, all enhanced by large, sun-filled windows. The fully finished walkout lower level, offering 2,868.49 sq. ft. of additional living space, features a recreation room, games area, second family room with fireplace, cold room(s), ample storage, and endless potential for multi-generational living. Complete with a 4-car garage and beautifully landscaped grounds, this exceptional property offers luxury, privacy, and natural beauty.

Welcome to this one-of-a-kind raised bungalow estate, situated on a breathtaking 4.5-acre manicured lot & offering approx.7,000 sqft of luxurious living space. Designed for both grand entertaining & comfortable family living, this exceptional home showcases high-end finishes, incredible amenities, & resort-style outdoor features. MAIN LEVEL offers approx.3,480 sqft with 10 ft ceilings & hardwood floors. A grand foyer welcomes you into the spacious Great Room featuring a gas fireplace & skylight. Formal Dining Room impresses with chandelier lighting, pot lights, mood lighting, and a coffered ceiling. Separate Living Room also features elegant coffered ceilings. The gourmet chefs kitchen is truly spectacular, with ceramic flooring, granite countertops & oversized islands, Sub-Zero built-in fridge/freezer, commercial-grade double oven stove, Bosch dishwasher, 3 sinks, wet bar, & walkout to a massive maintenance-free deck installed in 2024. This level also features 4 spacious bedrooms, including a luxurious Primary Retreat with walkout to a private deck, his & her closets, crown moulding & 5-piece ensuite. FULLY FINISHED LOWER LEVEL is an entertainers paradise featuring a huge Recreation Room with fireplace, wet bar, & 2 walkouts to the patio.Games Room with pool table, foosball & air hockey. Media Room with projector, fully equipped Gym with Sauna, second Kitchen with pantry & garage access. Spacious bedroom with 2-piece ensuite, built-in shelving & W/O to patio. Cantina with B/I shelving. Geothermal heating & cooling with dual-zone controls.OUTSIDE: Enjoy your own private resort featuring a Saltwater Pool with new liner, underground plumbing & concrete surround(2023).Tennis court with artificial turf & auto ball machine. Irrigation system & beautifully landscaped grounds. 5-car garages. New epoxy floor in the attached garage. Circular driveway accommodating up to 20 vehicles. Immaculately maintained estate offers luxury, privacy & unparalleled entertainment amenities.

Welcome to 1 Edgewild Drive, an extraordinary custom residence situated on one of Caledon's most prestigious and sought-after streets, offering breathtaking views and exceptional privacy. This meticulously designed home showcases superior craftsmanship, timeless finishes, and extensive high-end upgrades throughout.The grand family room features an impressive 18-foot cathedral ceiling, creating a stunning focal point filled with natural light. Elegant waffle and coffered ceilings enhance the main living areas, including the family room, dining room, office, kitchen, and bedrooms, delivering architectural sophistication at every turn. Solid wood poplar interior doors and trim extend throughout the entire home, including the finished basement. All bathrooms are luxuriously appointed with floor-to-ceiling granite and travertine tile. The primary ensuite features Hansgrohe shower fixtures, a Brizo freestanding tub filler and faucet, and custom solid maple cabinetry. Every bedroom includes a walk-in closet with professionally designed built-in organizers. Premium jatoba hardwood flooring and porcelain tile with custom mosaic detailing flow throughout the home. Professional window treatments are installed throughout, including motorized blinds in the family room and kitchen, as well as motorized drapery in the primary bedroom. The thoughtfully designed laundry room and mudroom include extensive custom cabinetry for optimal functionality and storage. The fully finished basement offers exceptional versatility with two separate French-door style exterior entrances and dedicated spaces including a private office, gym, recreation room, craft room, and workshop. Comfort is enhanced by an in-floor radiant heating system, supported by a boiler heating system with instant hot water capability. A central manifold plumbing system provides dedicated supply lines to each fixture.