2882 Charleston Side Road

Timeless elegance meets impeccable craftsmanship in this stunning Cheltenham estate. A rare find, this beautifully built 5+1 bed, 6 bath home in the sought-after Cheltenham community offers thoughtful design & exquisite details throughout. Chefs kitchen blending beauty & practicality, featuring a 48" Wolf gas range, Sub Zero fridge/freezer, Bosch dishwasher, built-in microwave, & custom quarter-sawn oak cabinetry. 5" solid white oak floors create an inviting atmosphere. The natural beauty of tumbled limestone, natural stone & marble in the kitchens, baths, & basement enhances the spaces timeless elegance, combining sophistication w/ comfort. The primary suite is a true sanctuary w/ heated floors, a spa-like steam shower, a romantic soaker tub, a spacious walk-in closet & focal fireplace. Every detail has been thoughtfully considered, from coffered ceilings in the dining room to vaulted ceilings in the family room & sunroom, adding architectural charm & grandeur. The main floor also includes a dedicated office, perfect for WFH or quiet study. Upstairs, 3 beds each w/ walk-in closets. Two share a Jack-&-Jill bath, while the 3rd has its own private ensuite creating private retreats for family & guests. Every detail, from custom millwork & extensive closet systems to solid wood doors, reflects timeless quality. Step outside to a beautifully landscaped yard, complete w/ irrigation system & a grand outdoor stone fireplace. The property boasts nearly an acre of lush grounds, with a 3-car garage plus an additional backyard workshop garage w/ a loft ideal for toys, landscape equipment & hobbies. For added versatility, theres a bright, welcoming 1-bed, 1-bath loft apartment w/ its own entrance, walk-in closet & separate laundry perfect for in-laws or rental income. The finished basement offers even more comfort w/ guest bed & bath, media & game zones, a bar, crafts room, gym, & a ton of storage, creating a warm, inviting and functional space for gatherings & daily life.

This Custom-Built Caledon Estate Sitting On 3.74 Acres Of Manicured Grounds, Offering Unmatched Privacy, Breathtaking Presence, And A Lifestyle Reserved For The Exceptional. Completely Transformed With A Newly Redone Exterior Façade, Fresh Concrete Work, And Extensive Renovations Throughout, This Residence Delivers Modern Luxury Minutes From The City.Inside, A Grand Foyer Opens To A Soaring Family Room Open To Above, Elegant Living And Dining Rooms, A Private Main-Floor Office, And An Eat-In Kitchen Designed For Both Everyday Living And Upscale Entertaining With Outdoor Patio Access. A Spacious Mudroom And 3-Car Garage Complete The Main Level.Upstairs, The Primary Suite Is A True Retreat With A 5-Piece Spa Ensuite Featuring Double Sinks, Glass Shower, Freestanding Tub, Separate Water Closet, And Two Walk-In Closets. A Second Primary Enjoys Its Own 5-Piece Ensuite, While Bedrooms Three And Four Share A Stylish Jack And Jill Bath. A Fifth Bedroom Includes A Full Private Bath, And The Convenience Of An Upper-Level Laundry Room Elevates Daily Living. Hardwood Flooring Throughout Adds Warmth And Sophistication.The Lower Level Is An Entertainer's Dream With A Large Recreation And Bar Lounge, A Full Bedroom With Closet, A Luxurious Bath With Sauna, Ample Storage, And A Dedicated Indoor Basketball Court - A Rare And Extraordinary Feature. Step Outside To Your Personal Resort With An Inground Pool, Expansive Grounds, And Endless Space To Relax, Host, And Enjoy.A One-Of-A-Kind Offering Combining Land, Luxury, And Lifestyle. This Caledon Estate Defines Elevated Living. List Of Upgrades Attached.

Welcome to this exceptional custom-built stone and brick residence nestled on a private 2.25-acre estate lot surrounded by breath taking countryside views. This impressive 2-storey home offers 4,444 sq. ft. above grade of finished living space, featuring soaring ceilings on both the main and second floors, an unfinished walk-out basement, and a beautifully landscaped fenced property with a natural stream running through. Enjoy peaceful sunsets and panoramic views from the expansive deck overlooking the terraced backyard. The grand foyer with cathedral ceilings opens to a spacious great room featuring a fireplace, pot lighting, and oversized windows allowing an abundance of natural light. The custom-designed kitchen showcases granite countertops, a large centre island, crown moulding, and a stylish matching backsplash, creating the perfect space for entertaining. Elegant hardwood flooring extends throughout both the main and second levels, complemented by superior craftsmanship and quality finishes throughout. The luxurious primary suite offers a spa-inspired 5-piece ensuite, providing a private retreat at the end of the day. Designed with comfort and versatility in mind, this home is ideal for large or multi-generational families seeking space, privacy, and modern living surrounded by nature. A rare opportunity to enjoy country tranquility with the convenience of a beautifully appointed custom home.