Old Bend, OR homes for sale & real estate

Old Bend, OR Homes for Sale

Step into the charm of this reimagined 1920s craftsman-thoughtfully remodeled with extensive custom designer finishes while preserving its timeless character. Tucked on a bluff in the heart of downtown Bend, just blocks from river floats, farmers market, summer concerts, and the city's best dining, this one-of-a-kind home is a true gem. Inside, custom oak cabinetry, honed marble countertops, new appliances, updated windows and doors, tongue and groove wood ceilings, and solid oak hardwood floors add warmth throughout. The spa-like primary retreat offers rare comfort for a home of this era. Step outside to a whimsical, lush garden with mature landscaping and entertain around your fire pit&md

Old Bend, OR Homes for Sale

Discover timeless charm and modern versatility in Bend's Historic District just steps from the The Box Factory, the Old Mill District, and Downtown Bend. This beautifully updated 1925 Craftsman bungalow retains its historic character while offering today's comforts, including a light-filled living room and a dine-in kitchen. With 2 bedrooms, 1 bath, and a cozy loft, the main home is perfect for comfortable living. A private back patio separates it from the stunning ADU, built in 2021, featuring a spacious open floor plan, sleek kitchen with ample storage, 1 bedroom, 1 bath, a loft and its own patio and dedicated parking. Live in one and rent the other, create a guest retreat, or generate st

Old Bend, OR Homes for Sale

Incredible investment opportunity in the heart of Bend! This centrally located home features a rare, transferable short-term rental permit, offering a unique blend for personal use and income potential. Just steps to the Deschutes River, Old Mill District and Downtown Bend, this property is ideally situated for vacationers and owners alike. With a proven track record of strong rental income, this high-performing vacation rental offers excellent revenue with tremendous potential for growth thanks to Bend's year-round demand. As a bonus, the seller has plans for an Accessory Dwelling Unit (ADU) — opening the door to even more income or guest accommodations. Buyers are encouraged to perf

Old Bend, OR Homes for Sale

Step into the perfect blend of timeless charm and modern convenience with this 1918 Craftsman home, ideally located in the vibrant heart of downtown Bend. The main residence features 2 bedrooms, 1 bath and a laundry/storage room, showcasing classic architectural details. A detached studio-style ADU adds versatility, complete with its own kitchen, bathroom, and generous storage closet - ideal for guests, rental income, or a home office. Set on a 0.14-acre lot, the property also offers exciting development potential. Just blocks from the Deschutes River, Old Mill District, local parks, and downtown Bend's mix of shops and restaurants, this home places you at the center of it all. Whether you'