Old Bend Homes for Sale

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 perennial

Connor Johnson Stellar Realty Northwest

HOME + ADU! 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

Laura Blossey Avenir Realty

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

Charming and fully remodeled home in the heart of Bend's Historic District! This 2-bedroom, 1-bath gem offers 972 square feet of modern comfort while preserving its historic character. Situated on a desirable corner lot across from Amity Creek Magnet School, it's also within walking distance to shopping, dining, and the vibrant offerings of Old Town Bend. Highlights include all-new PEX plumbing,

Nancy Kramer RE/MAX Out West Realty

This rare four bedroom mill-era home is in the Priority Enrollment Zone for Amity Creek Magnet School- the only Bend elementary school with a 10/10 GreatSchools rating. Located on an elevated lot between downtown and the Old Mill, the property boasts one of Bend's best locations, just blocks from Miller's Landing and Drake Park. Enjoy easy access to everything that makes Bend living amazing!The

Nick Berrey Nicholas Berrey

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

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

Tara Farstvedt Cascade Hasson SIR

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 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

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

Nestled on a quiet street in the historic district, this fully renovated charming home lives larger than the square footage with its open beam ceilings, natural light, and carefully crafted high-end finishes. Every detail has been thoughtfully chosen, from the handcrafted tiles and marble countertops in the kitchen to the heated tile floors and modern cabinetry, with an abundant of storage in the

Colleen Peterson Engel & Voelkers Bend

Hard to find 4 plex in Old Town between the Old Mill and Downtown with river and mountain views in Opportunity Zone. 4 units- All units 2 stories. 2 have fenced yards. All have private decks. All have stainless appliances, laminate floors and newer energy eff. windows. All units remodeled. Quiet, dead-end street with low maintenance landscape. Future development of 3 units, plans for two

Gary Clow Total Real Estate Group

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

These architectural gems showcase luxury at every turn, with expansive high ceilings, multiple outdoor terraces offering sweeping skyline views, three generously proportioned en-suite bedrooms with sizeable walk-in closets, ensuring a haven of comfort and luxury. The heart of each home is an open-plan living space, where every detail from the dream kitchen — equipped with a full-length island,

Beth Davies LivOregon Real Estate LLC

Discover modern living with these four brand-new construction townhomes located in the heart of downtown Bend. Perfectly situated across the street from Jackson's Corner - close to the Old Mill District and downtown's vibrant shops, restaurants, & entertainment, this is the ideal location for those looking to embrace urban living with the convenience of low-maintenance luxury. These homes feature

Nick Wilhite The Agency Bend