Vintage homes for sale & real estate in Sisters, OR

Vintage Home for sale in Sisters, OR:

A true Bend original that you absolutely must see in person! Built in 1946 by Olaf Skjersaa, a pioneer of Bend's ski culture, this distinctive Arts & Crafts home showcases his handcrafted front door, staircase, original woodwork and built-ins. Offering 5 beds, 3 baths, over 3,400 sq ft and two main-level primary suites, the flexible floor plan features multiple living spaces ideal for guests, work or multi-gen living. Historic charm meets modern comfort with a newer roof, replacement windows, fresh interior and exterior paint, tankless water heaters, updated HVAC and Trex deck. Hardwood floors and three fireplaces add warmth throughout. Outside, enjoy a spacious 1/3-acre lot, mature l

Vintage Home for sale in Sisters, OR:

Walkable westside income property with three remodeled units on one lot! The 2-bed, 1-bath main house features a large covered front porch, malm fireplace, finished basement and separate utilities. The ADU adds two 1-bed, 1-bath units, upstairs and downstairs, both offered fully furnished and turn-key. All units are rented monthly with low vacancy, delivering steady income from day one. Two off-street parking spots included. Location is the real draw: stroll to downtown Bend's restaurants, shops, and nightlife, and to the Deschutes River's trails and parks. Walkable westside addresses attract steady tenant demand and appeal to owner-occupants too. Live in one unit and let the others help ca

Vintage Home for sale in Sisters, OR:

OPEN HOUSE SATURDAY, OCTOBER 24 1-3pm - ADU ONLY. Main house is tenant-occupied; please do not disturb the tenant. Picture yourself on Bend's coveted westside, a short stroll to the river trail, downtown, and Newport Avenue favorites like Newport Market, Back Porch Coffee, and Spork. This rare Union Street offering pairs two charming cottages on one lot, moments from the Neighborhood Greenway for easy, car-free access by foot or bike. The 2017 back cottage is Earth Advantage Platinum and Zero Energy certified. The 1926 front bungalow keeps its original character and refinished hardwood floors, with thoughtful updates throughout: new windows and doors, a newer roof, full insulation and profe

Vintage Home for sale in Sisters, OR:

Rare opportunity in Bend's most desirable Westside neighborhoods, this . 14 acre lot sits nicely between the Galveston and Newport Corridors, close to shopping, dining, services, and downtown. The property includes a 1919-built, 3-bedroom, 2-bath home with 876 sqft - ready for a builder or developer to reimagine. The lot's size and prime location support a range of possibilities, from an extensive renovation, to a full tear-down for a custom new home. There's also potential to add an ADU, all subject to city approval, making this an especially compelling opportunity for builders looking to maximize the site. Street and alley frontage add flexibility for parking and site design, making this

Vintage Home for sale in Sisters, OR:

Rare opportunity to own a fully remodeled duplex in Bend! 100k remodel completed in 2022! This single-level property features two 869 sq. ft. units, each offering 2 bedroom, 1 bathroom, spacious living areas, full kitchens with stainless steel appliances, dedicated laundry rooms, large closets, 2 new heat pumps, private fenced backyard, and two off-street parking spaces. Situated on a 7,840 sq. ft. lot, this property is ideal for investors or owner-occupants looking to offset their mortgage with rental income. Walk to downtown restaurants, breweries, coffee shops, grocery stores, parks, and the Bend Park & Recreation athletic facility. A bus stop is located across the street, adding

Vintage Home for sale in Sisters, OR:

Coffee on the front deck, a stroll to the river to watch the surf wave, then lunch & a local pint just blocks from home. This is west side living done right in one of Bend's most vibrant neighborhoods. This historic home keeps its character & handles the big stuff: a 2023 efficient heat pump w/ A/C, a newer water heater & dishwasher w/ added cabinetry, & a new roof going on Oct 2026. Refinished & newly added wood floors warm the living room, office, & primary suite, where vaulted ceilings & skylights fill the space w/ light. The neighborhood provides 2 playgrounds, Overturf butte w/ trails & off-leash dog park, and quick access to Mt. Bachelor