An unrivalled real estate opportunity in prestigious Forest Hill South, 29 Highbourne Rd balances the British Influence Colonial Revival architectural character with extraordinary future development potential. Positioned prominently near the corner of Highbourne Rd and Oxton Ave, this elegant residence offers a rare foothold in one of Toronto's most exclusive enclaves, commanding unique street exposure that presents lucrative long-term expansion options or premium land value within a blue-chip postal code. Beyond its unique prosperity, the property provides immediate access to Canada's elite educational institutions, situated just steps from the Upper Canada College campus, minutes to BSS and high rank Brown Junior Public School district. The surroundings foster a luxurious urban lifestyle, where the natural serenity of Beltline Trail, Oriole Park, and tranquil ravine systems seamlessly pair with unmatched connectivity, placing the upscale boutiques, fine dining, both Davisville and Yonge & St. Clair subway stations just minutes away. Private driveway and detached garage for easy parking. Symmetrical facades and striking black door and window fenestrations create a balanced, graceful architectural presence. Black iron fence wraps around the front garden enhance the curb appeal. Versatile 3-bed 3-bath layout features a rare main-floor bedroom with a heated-floor ensuite, complemented by two bright upper-level retreats including a principal suite with a walk-in closet and built-in organizers. Seamlessly blending period artistry with modern comfort, the renovated interior shines with rich hardwood, classic wainscoting, crown moldings, and a stately bay window, alongside contemporary refinements featuring a gas fireplace, ambient pot lights, stone countertops, marble backsplash, and sleek basement bathroom. Flowing effortlessly to a private back deck, this home is as perfect for sophisticated family residence today as it is for visionary redevelopment tomorrow.