Welcome to Cypress Circle in South Redlands, a historical tree-lined street known for its collection of bungalow-style and Craftsman homes. The central promenade features towering Italian cypress trees that create a picturesque setting for leisurely neighborhood strolls. Don't miss this rare opportunity to own a charming 1932 Tudor Revival inspired home with three bedrooms and three bathrooms - the perfect blend of modern comfort and original character. Cross the classic brick patio set in a basket weave pattern to the front door, and enter into the over-sized living and dining room. This inviting space features mountain views, plaster walls, a dramatic floor-to-ceiling window, a wood-burning fireplace, a built-in bookshelf, and Art Deco details. The expansive window fills the home with natural light and overlooks the lush backyard, highlighted by a mature lemon tree. Just off the main living area, the recently updated kitchen offers newer Samsung smart appliances, quartz counter-tops, an island with seating, exposed brick, and a sunlit bay window breakfast nook. The first floor includes a guest/kid's' room with mountain views, an updated hall bath, and an over-sized primary suite with mini-split AC. The beautifully remodeled en-suite bathroom features a double shower with four shower heads (two rainfall), pebble flooring, dual sinks, and floating shelves. Behind a stylish barn door, stairs lead to the second-story third bedroom. With its own bathroom and mountain views, this versatile space works well as an office, guest suite, older kid's room, or second primary. The private backyard offers fruit trees, lawn space, and a large stone fireplace ideal for outdoor entertaining. Additional highlights include a letter box, coved ceilings, recessed lighting, central heat and AC, a laundry room, a new roof (April 2025), and storage in the attached garage. Located near Prospect Park and downtown Redlands. With its rare blend of history, upgrades, and location, this home won't stay on the market long - schedule your showing before this Cypress Circle gem is gone.