Old Bend Houses for Sale

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

Deborah Martorano RE/MAX Key Properties

Historic Charm in the Heart of Bend!Welcome to the Henry Maynard House-a light, bright Historical District westside bungalow full of character and thoughtful updates. Inside, you'll find arched doorways, refinished hardwoods, and a fully updated kitchen that's perfect for cooking or entertaining. Step outside to a peaceful yard with a cherry, peach, pear, and plum tree orchard, fenced

Connor Johnson Stellar Realty Northwest

TWO transferable short term rental permits on this original 1920 bungalow. Located a few blocks away from Jackson's Corner on a quiet, dead-end residential street, each unit has been fully remodeled with extraordinary attention to detail and is a terrific example of historic regeneration. Upgraded down to the studs with new plumbing, electrical, insulation, etc. Originally a modest millhouse

Bryant Green Cascade Hasson SIR

This vintage restored and updated Craftsman bungalow with STR permit, is located in the heart of downtown Bend. Enjoy breathtaking mountain views from the charming front porch swing. Situated on a spacious lot with impressive curb appeal, the home boasts impeccable craftsmanship, showcasing exquisite tile work, custom cabinetry, fine trim, restored hardware, & beautiful lighting fixtures. The

Karen Malanga RE/MAX Key Properties

Downtown Bend is the place to be and NW Florida Avenue is a location that can't be beat. Spacious traditional craftsman home nestled between downtown Bend and the Mill Quarter. Enjoy the ease of access to Bend's finest markets, social gathering hot spots & eateries, music venues, parks and the Deschutes River. This 3 BD/ 2 BA boasts all the traditional craftsman features with modern amenities.

Christin Hunter Duke Warner Realty

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

Matthew Johnson RE/MAX Key Properties

Located in Bend's Historic District, this beautifully restored 1920s Craftsman blends timeless character with modern comfort. The single-level home offers 956 +/- sq ft of inviting living space, plus an additional 440 +/- sq ft basement with laundry and extra storage. Step inside to original Douglas Fir wood floors, high ceilings, crown molding, and vintage-inspired details throughout. The

Jordan Ries Assist 2 Sell Buyers & Seller

Charming 2-bedroom, 1-bath home in the heart of Bend's Historic Old Town District, just blocks from downtown and the Old Mill. Built in 1920 and thoughtfully renovated throughout, this home blends vintage character with modern upgrades. Enjoy a completely remodeled kitchen with new cabinets, updated PEX plumbing, all-new electrical, new insulation, and a gas tankless water heater. The tiled bath

Nancy Kramer RE/MAX Out West Realty

Investor alert ! Prime Investment Opportunity in Old Bend – Dual-Dwelling Property on NW Georgia Ave, Located in the highly desirable neighborhood between DOWNTOWN and OLD MILL in Historic Old Town Bend, 530 and 530 1/2 NW Georgia Ave. presents a rare opportunity to own a dual-dwelling in the heart of Bend. This property features 2 homes! The main house located at 530 NW Georgia Ave is a

Elizabeth Allen Duncan Real Estate Group Inc

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

Cole Billings Varsity Real Estate

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

Michelle Mills RE/MAX Key Properties

Charming Downtown Gem with Unique Character & Prime Location! Beautifully crafted to blend vintage charm with modern comfort and so close to the Box Factory, Old Mill, and Downtown. This solid built home offers extra thick walls for exceptional insulation and sound dampening, allowing you to be right in the middle of the action, while also able to enjoy peace and quiet at home. Stunning hardwood

Gregory Powell Keller Williams Realty Central Oregon

This inviting 5-bedroom, 3-bath home on a double lot in the historic district blends timeless elegance with modern convenience. It features original built-ins, spacious walk-in closets, and classic details that highlight its unique design. Located across from Drake Park, enjoy views of the lovely greens of summer, vivid colors of autumn, and snowy winter landscapes. Downtown dining, shopping and

Greg Messick Realty Net of Central Oregon

Enjoy the best of Bend in this charming cottage conveniently located on a quiet block in the heart of the Old Bend Historic District. Ideally situated between Bend's vibrant downtown and the Old Mill District with easy access to the Deschutes River. Step out your door to coffee shops, brew pubs, restaurants, groceries, retail shopping, and lively entertainment. Features an efficient layout, claw

Jake Hermeling OHT

Unleash Your Vision: An extraordinary opportunity awaits in the vibrant heart of Bend's Box Factory district. Picture this: a building with street frontage that commands attention, nestled perfectly between downtown Bend and the Old Mill District. Step inside to discover an industrial-chic interior, bathed in natural light. Zoned CG, this property invites boundless opportunity from urban

Sheila Balyeat Cascade Hasson SIR

Unleash Your Vision: An extraordinary opportunity awaits in the vibrant heart of Bend's Box Factory district. Picture this: a building with street frontage that commands attention, nestled perfectly between downtown Bend and the Old Mill District. Step inside to discover an industrial-chic interior, bathed in natural light. Zoned CG, this property invites boundless opportunity from urban live/

Sheila Balyeat Cascade Hasson SIR