Cypress Circle in South Redlands is a historic circular residential tract developed between 1916 and 1930, renowned for it's bungalow and Craftman-style homes and a distinct, central promenade of Italian Cypress trees. Originally planned by Burton Cannon and landscaped by William Ferguson. The area features homes designed by notable architect Herbert Powell, creating a charming unique neighborhood. Charming 1932 three-bedroom, three-bath home on historical Cypress Circle, where modern comfort meets original character. Cross the classic brick patio to the front door, and enter into the over-sized living and dining room. This inviting space features coved ceilings a dramatic floor-to-ceiling original picture window which brings the outdoors in, 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, Shaker style white cabinetry with self closing hinges, under the cabinetry lighting, and a sunlit breakfast nook perfect for morning coffees. The first floor includes a spacious guest/kids’ room an updated hall bath, and an over-sized primary suite. The beautifully remodeled en-suite bathroom features a double shower with four shower heads (two rainfall), pebble flooring, dual sinks, modern and functional touch- sensor LED mirrors and floating shelves. Behind a stylish barn door, stairs lead to the second-story third bedroom. With its own bathroom. This versatile space works well as an office, guest suite, older kids’ room, or second primary.The private backyard offers a shade tree, fruit trees, a storage shed, lawn space, and a large stone fireplace ideal for outdoor entertaining under the stars. Additional highlights include recessed lighting, central heat and AC, a new roof (April 2025), partial dual pane windows and a new tank-less water heater for energy efficiency, a few original windows spread through-out the home add vintage details and charm, fresh landscaping designed for both relaxation and gathering, separate laundry room for convenience and storage in the attached garage. Located near Prospect Park, Redlands Dog Park, walk-able and vibrant Historic Downtown Redlands and walking distance to Gerrards local market for all of your local bakery goods!