The "Family Cottage-in-the-City" Hilltop Retreat: a character-filled home boasting unique geography, privacy, and income potential. 1398 Davenport is a sanctuary on the escarpment with treetop views where every day feels like a getaway. This charming sunny 3-bedroom home offers a rare lifestyle of birdsong, fresh air, and tranquility, all while being part of a tight-knit, "know-your-neighbour" hilltop community. Step inside this sun-drenched, south-facing residence and feel the immediate warmth of a well-loved home. The main floor features an efficient, breezy flow with a welcoming entrance lobby, a convenient 2-piece powder room, and a living room centered around a cozy wood-burning fireplace-perfect for winter nights. Oak stairs lead you upwards, illuminated by a bright skylight that bathes the home in natural light. The 130ft deep lot garden oasis is a true "Canadian enclosure" where the Kitchen/Dining area opens to a spacious patio for hosting shaded events, or you can ascend to the upper level to discover a mature perennial garden. Backing onto multi-million dollar estates, this property offers unmatched privacy and prestige at an accessible price point. A rare and special feature of this home is the separate, renovated lower-level apartment. With high ceilings, a separate front entrance, and an abundance of light, it serves as a guest suite or a high-value income generator to offset your mortgage. This home shows Pride of Ownership, having been extensively maintained with a clear eye for detail and comes with full receipts and warranties for all recent work. It is truly move-in ready. As well, it's only a short walk to Wychwood Park, Hillcrest Park, Wychwood Barns with farmers' markets, lively St. Clair West, TTC buses on Davenport and Dufferin, Bicycle lanes on your doorstep in all directions, and great schools like Regal Rd Junior and Winona Dr Senior just a few steps away. Come experience the quiet of the hill for yourself and leave the city noise behind.