Vintage homes for sale & real estate in Old Bend, OR

Vintage Home for sale in Old 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 Old Bend, OR:

Charming Historic Cottage Mill House in Old Town Bend Step back in time with this rare opportunity to own a piece of Bend's history. Built in 1916, this 1,128 sq. ft. cottage mill house offers two distinct living spaces, each with its own private entrance. The lower level features the original home, complete with a cozy bedroom, full bath, laundry area, a kitchen and living space. Upstairs, a charming studio apartment offers additional living flexibility, boasting a full bath and kitchenette—perfect for guests, rental income, or multi-generational living. A private front courtyard welcomes you, while a single-car garage and two dedicated parking spaces provide convenience in this soug

Vintage Home for sale in Old Bend, OR:

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

Vintage Home for sale in Old Bend, OR:

A rare opportunity to own a piece of Bend's founding history in the heart of the Old Town Historic District, the city's first platted neighborhood and birthplace of its mill-town legacy. Situated between NW Bond and NW Staats Streets, just three blocks from the vibrant downtown core and steps from Drake Park. The original 1915 Craftsman bungalow is one of the few surviving residences from the mill boom era, built the same year as the lumber mills that would later form the Old Mill District. While currently uninhabitable, prior renovation plans were approved (an 18+ month process) by Historic Landmarks and City of Bend for three units: a restored 841-sf historic cottage and a new duplex with