Vintage homes for sale & real estate in Bend, OR

Vintage Home for sale in Bend, OR:

Welcome to one of Old Bend's rare gems—a 1920 bungalow nestled in the heart of Bend's most coveted neighborhood. Originally part of the Bend Townsite Company's distinguished ''Nob Hill'' development of six fine homes and bungalows, this residence embodies the character and history of early Bend while offering the freedom of not being located within the Historic District. Enjoy morning coffee on your front porch as you admire the beauty of your tree-lined street. Walk to the Deschutes River, downtown Bend, and the Old Mill District—everything you love about Bend is right at your doorstep. With one to two bedrooms, alley access, and room to expand, the possibilities are endless. E

Vintage Home for sale in Bend, OR:

Own a slice of Bend's hippest real estate location with this historic home and ADU located in the heart of it all! 1/4 mile from Miller's Landing and the Deschutes River and a stone's throw from the vibrant Box Factory, thriving downtown, and iconic Old Mill. The renovated home lives large with a primary plus second bedroom, open living area, 2025 updated kitchen, dining, and full bath while maintaining the 1916 historic charm with its covered porch, leaded glass, classic trim work and the original 500 sf of basement storage. The renovated one-bedroom ADU has a minimalistic and contemporary vibe boasting hardwood, solid surfaces, tiled shower, open shelving and modern fixtures. Both homes h

Vintage Home for sale in Bend, OR:

Prime Midtown location! Remodeled, updated and private, this is the retreat you have been looking for. Not only is this a large ¼ acre corner lot, but there is also a 6-car garage with a driveway long enough to fit an RV. Forfeit the electric bill with the 19 owned solar panels! There is a beautiful block wall surrounding the yard with custom gates to access the spacious courtyard ready for your personal touches. Living space feels larger in this L shaped single level home featuring a huge great room with built-in bookshelves, vaulted ceilings & travertine stone gas fireplace. The kitchen is a chef's delight along with soft close drawers/cabinets, refrigerator and dishwasher

Vintage Home for sale in Bend, OR:

We bought this home to be on the river, to grow our family & to build our dream. Waking to the sound of water & walking to First Street Rapids, Pioneer Park, & downtown Bend became part of our everyday joy. We've loved the convenience—paddling from our backyard, strolling to music, grabbing coffee or dinner without ever needing a car. The home itself blends charm & comfort w/ thoughtful updates like Viking appliances & warm, inviting layout. Set on a rare . 31-acre RM-zoned riverfront lot, it also offers incredible future potential. We secured an approved plan for a major remodel so your dream riverfront expansion or investment is already in motion. Living