Old Bend Homes

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  /24

  $1,135,000

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  156 NW Jefferson Place, Bend, OR 97701

  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 Coastal Sotheby's International Realty

  156 NW Jefferson Place, Bend, OR 97701
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• 

  

  

  /64

  $1,815,000 Sold Apr 24, 2025

  • 2,567 Sq Ft
  • $707/SF
  • 12 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1946

  414 NW State St, Bend, OR 97701

  Located on a spacious corner lot in one of Bend's most sought-after neighborhoods, this stunning Mid-Century Modern home mixes timeless appeal with contemporary upgrades. The thoughtfully designed layout offers an abundance of natural light and multiple outdoor living spaces. The kitchen was recently revamped, and boasts a sleek and practical design with gorgeous soapstone countertops. Both guest

  Jessica Fraley Stellar Realty Northwest

  414 NW State St, Bend, OR 97701
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  /32

  Est $1,096,117 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,543 Sq Ft

  256 NW Saint Helens Place, Bend, OR 97701

  256 NW Saint Helens Place, Bend, OR 97701
• 

  

  

  /45

  $1,325,000

  • 3 Beds
  • 2 Baths
  • 1,527 Sq Ft

  232 NW Congress St, Bend, OR 97701

  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

  232 NW Congress St, Bend, OR 97701
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  /9

  $570,000 Sold Apr 17, 2025

  • Land
  • 0.10 Acre
  • $5,700,000 per Acre

  • 74 Days On Market

  315 NW Riverside Blvd, Bend, OR 97703

  A True Gem in the heart of downtown Bend. A stunning flat lot located on the quiet side of Riverside Blvd. This lot is in a charming older neighborhood withOUT being in the restrictive Historic district. Experience the pinnacle of Bend living, perfectly positioned to embrace the vibrant energy of downtown Bend and The Old Mill District. This prime location offers an unparalleled blend of

  Beth Davies LivOregon Real Estate LLC

  315 NW Riverside Blvd, Bend, OR 97703
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  /42

  Est $713,782 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,060 Sq Ft

  137 NW Florida Ave, Bend, OR 97701

  137 NW Florida Ave, Bend, OR 97701
• 

  

  /34

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,131 Sq Ft

  535 NW Florida Ave, Bend, OR 97701

  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

  535 NW Florida Ave, Bend, OR 97701
• 

  

  /30

  $3,280,000 Sold Apr 01, 2025

  • 3,336 Sq Ft
  • $983/SF
  • 22 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1992

  615 NW Riverfront St, Bend, OR 97701

  Nestled in the heart of Bend, Oregon, this stunning riverside property offers not only a serene escape but also unparalleled convenience. Imagine living just moments away from downtown, the Old Mill District, Galveston Ave., Newport Ave. parks, trails and so much more. Boasting 4 generous sized bedrooms and 3 beautifully appointed bathrooms, this home provides ample space for relaxation

  Eleanor Anderson Coastal Sotheby's International Realty

  615 NW Riverfront St, Bend, OR 97701
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  /29

  Est $1,238,725 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,905 Sq Ft

  237 NW Florida Ave, Bend, OR 97701

  237 NW Florida Ave, Bend, OR 97701
• 

  

  /10

  $1,750,000 Pending

  • 5 Beds
  • 3 Baths
  • 4,058 Sq Ft

  111 NW Jefferson Place, Bend, OR 97701

  **Check out this Amazing Investment Opportunity!! These two (2) lots in the heart of Old Bend totaling .33 acres, near the Old Mill and steps away from the Bend Whitewater Park are ready for your imagination. The main house was built in 1919 and has an expansive deck with Cascade Mountain and Deschutes River views including the Bend Whitewater Park. Tranquil and peaceful in the heart of all the

  Jennifer Gregoriou eXp Realty, LLC

  111 NW Jefferson Place, Bend, OR 97701
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  /18

  $877,940 Sold Apr 01, 2025

  • 1,494 Sq Ft
  • $588/SF
  • 15 Days On Market

  • Built 1917

  32 NW Gilchrist Ave, Bend, OR 97703

  Occupied. DND Tenants. Terrific opportunity in a million dollar location in Old NW Bend! Rehab, Remodel or Rebuild. This one has every opportunity. The street level portion of the residence is quite original and has been a long term rental for decades, so very little improvements. The 2 bedroom apartment over the garage is newer as is the garage & has laundry. Miller's Landing is alongside

  Peter Jameson J Residential Properties

  

  32 NW Gilchrist Ave, Bend, OR 97703
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  /26

  Est $1,048,252 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 2,063 Sq Ft

  418 NW Florida Ave, Bend, OR 97701

  418 NW Florida Ave, Bend, OR 97701
• 

  

  /38

  $825,000

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft

  25 NW Hood Place, Bend, OR 97701

  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 Coastal Sotheby's International Realty

  25 NW Hood Place, Bend, OR 97701
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  /32

  $731,450 Sold Feb 28, 2025

  • 672 Sq Ft
  • $1088/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1920

  77 NW Mckay Ave, Bend, OR 97701

  This charming downtown cottage sits on a coveted corner lot, steps away from Drake Park, downtown Bend, the Deschutes River footbridge to Columbia Park, The Deschutes River Trail to Miller's Landing Park, Bend Whitewater Park, The Old Mill District, and Farewell Bend Park. The cozy two-bedroom, one-bathroom home boasts a fully fenced yard in a stellar location. Recent updates include new

  Greg Millikan Duke Warner Realty

  77 NW Mckay Ave, Bend, OR 97701
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  /42

  Est $1,010,523 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,019 Sq Ft

  354 NW Florida Ave, Bend, OR 97701

  354 NW Florida Ave, Bend, OR 97701
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  /33

  $770,000 Open Sat 1PM - 3PM

  • 2 Beds
  • 1 Bath
  • 957 Sq Ft

  805 NW Georgia Ave, Bend, OR 97701

  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

  805 NW Georgia Ave, Bend, OR 97701
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  /37

  $1,000,000 Sold Dec 26, 2024

  • 1,584 Sq Ft
  • $631/SF
  • 64 Days On Market

  • Built 1916

  334 NW Hill St, Bend, OR 97701

  Investment opportunity with 3 transferable Short Term Rental permits on one Tax lot. Unlimited options and opportunities with this unique duplex with separate cottage. Excellent location with walkability to Downtown Bend, Box Factory and Old Mill. Commercial General zoning allows for multitude of options. Includes all furnishings and appliances.

  Brian Intlekofer Obsidian Real Estate Group

  334 NW Hill St, Bend, OR 97701
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  /21

  Est $703,329 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft

  334 NW Chamberlain St, Bend, OR 97701

  334 NW Chamberlain St, Bend, OR 97701
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  /41

  $825,000 Open Fri 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,759 Sq Ft

  106 NW Colorado Ave, Bend, OR 97701

  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 C.O.

  106 NW Colorado Ave, Bend, OR 97701
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  /24

  $912,000 Sold Dec 20, 2024

  • 1,622 Sq Ft
  • $562/SF
  • 220 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2024

  20 NW Mccann Ave Unit 7, Bend, OR 97703

  These architectural gems showcase luxury at every turn. The heart of each home is an open-plan living space, where every detail from the dream kitchen — equipped with a full-length island, pristine quartz countertops, high-end stainless steel appliances and spacious walk in pantry— has been carefully selected to cater to the culinary enthusiast, to the beautifully engineered hardwood flooring and

  Beth Davies LivOregon Real Estate LLC

  20 NW Mccann Ave Unit 7, Bend, OR 97703
• 

  

  /74

  Est $1,133,122 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,011 Sq Ft

  304 NW Hunter Place, Bend, OR 97701

  304 NW Hunter Place, Bend, OR 97701
• 

  

  /29

  $2,725,000

  • 5 Beds
  • 3 Baths
  • 4,871 Sq Ft

  898 NW Riverside Blvd, Bend, OR 97701

  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

  898 NW Riverside Blvd, Bend, OR 97701
• 

  

  /32

  $985,000 Sold Nov 21, 2024

  • 1,312 Sq Ft
  • $751/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1920

  240 NW Georgia Ave, Bend, OR 97701

  Location, location, location! Nestled perfectly between the Box Factory and Downtown Bend, this home is ideal for the active family or a savvy rental opportunity! When you step inside this meticulously updated 3 bed/2 full bath home, you will find brand new appliances, double-pane windows, new hardwood floors, a new pellet stove, and more. From the strong natural light to the arched doorways and

  Joslyn Bryant Keller Williams Realty C.O.

  240 NW Georgia Ave, Bend, OR 97701
• 

  

  /22

  Est $686,561 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 810 Sq Ft

  137 NW Georgia Ave, Bend, OR 97701

  137 NW Georgia Ave, Bend, OR 97701
• 

  

  /15

  $300,000

  • Land
  • 0.10 Acre
  • $3,000,000 per Acre

  0 Colorado St Unit 220193272, Bend, OR 97703

  PRIME LOCATION for residential or multiunit development. Corner lot of Colorado and Lava. Alley access on rear of lot. Existing garage that will need to be removed, and historic overlay is present in the neighborhood. Buyer to complete due diligence on their specific use and project. 2 - 4 unit use or SFH. Geotechnical Survey and Land Survey also available as well as notes from PreApp meeting

  Brent Cole Triple Oaks Realty LLC

  0 Colorado St Unit 220193272, Bend, OR 97703
• 

  

  /42

  $3,075,000 Sold Nov 01, 2024

  • 4,251 Sq Ft
  • $723/SF
  • 107 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1911

  540 NW Congress St, Bend, OR 97701

  Nestled in the heart of Bend (just 3 blocks to town and 2 blocks from the river) and situated on a stunning and meticulously kept double lot (.32 acres), the Overturf House offers 4251 sf of timeless living space in the historic Drake Park District. This unique 3-level, 4-bedroom (plus bonus room) home seamlessly blends traditional Craftsman touches with modern convenience and timeless finishes.

  Eleanor Anderson Coastal Sotheby's International Realty

  540 NW Congress St, Bend, OR 97701
• 

  

  /18

  Est $719,657 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 891 Sq Ft

  501 NW Hill St, Bend, OR 97701

  501 NW Hill St, Bend, OR 97701
• 

  

  /25

  $699,999

  • 1 Bed
  • 1 Bath
  • 604 Sq Ft

  346 NW Hunter Place, Bend, OR 97701

  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

  346 NW Hunter Place, Bend, OR 97701
• 

  

  /65

  $800,000 Sold Oct 21, 2024

  • 1,889 Sq Ft
  • $424/SF

  • 3 Beds
  • 2 Baths
  • Built 1915

  505 NW Florida Ave, Bend, OR 97701

  Step into history with this charming 1915 gem. Located in a historic neighborhood, on a corner lot close to Downtown and the Old Mill District. Original front porch and mature landscaping preserve the home's authentic charm. The cozy living room, complete with a fireplace, invites warm gatherings, and the large dining room is perfect for memorable meals. The kitchen blends classic appeal with

  Lisa Lamberto Coastal Sotheby's International Realty

  505 NW Florida Ave, Bend, OR 97701
• 

  

  /22

  Est $686,866 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 698 Sq Ft

  525 NW Hill St, Bend, OR 97701

  525 NW Hill St, Bend, OR 97701
• 

  

  /44

  $2,780,000

  • 4,416 Sq Ft

  97 NW Jefferson Place, Bend, OR 97701

  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

  97 NW Jefferson Place, Bend, OR 97701
• 

  

  /39

  $1,125,000 Sold Sep 23, 2024

  • 1,604 Sq Ft
  • $701/SF
  • 5 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  20 NW Mccann Ave Unit 6, Bend, OR 97703

  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

  20 NW Mccann Ave Unit 6, Bend, OR 97703
• 

  

  /33

  Est $1,211,500 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,951 Sq Ft

  500 NW Lava Rd, Bend, OR 97701

  500 NW Lava Rd, Bend, OR 97701
• 

  

  /25

  $599,900

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  533 NW Hill St, Bend, OR 97703

  Charming historic bungalow located just a few blocks from Downtown Bend; previously used as a vacation rental and as a health practitioner's office, zoned CG (Commercial General). Recent improvements include a new 30-year roof, furnace, updated bathroom and new windows. The front and back yards have beautiful and environmentally-friendly landscaping with fruit trees, blue spruce, grasses and

  Jason Boone Duke Warner Realty

  533 NW Hill St, Bend, OR 97703
• 

  

  /22

  $975,000 Sold Aug 30, 2024

  • 1,210 Sq Ft
  • $806/SF
  • 21 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1920

  225 NW Delaware Ave, Bend, OR 97701

  Nestled in the idyllic historical district of Bend, this charming 1920s bungalow is the perfect retreat. This property is perfectly located smack dab between the old mill and downtown Bend! Meticulously maintained, this home boasts an open great room floorplan with an updated kitchen and bathroom with heated floors. Light and bright the kitchen boasts leathered quartz countertops, and custom

  Carey McQuate Coastal Sotheby's International Realty

  225 NW Delaware Ave, Bend, OR 97701
• 

  

  /55

  Est $1,359,730 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,335 Sq Ft

  121 NW Bond St, Bend, OR 97701

  121 NW Bond St, Bend, OR 97701
• 

  

  /13

  $599,900

  • 1 Bed
  • 1 Bath
  • 661 Sq Ft

  605 NW Delaware Ave, Bend, OR 97701

  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

  605 NW Delaware Ave, Bend, OR 97701
• 

  

  /17

  $555,000 Sold Aug 28, 2024

  • 720 Sq Ft
  • $771/SF
  • 11 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1930

  343 NW Georgia Ave, Bend, OR 97701

  Delightful little cottage just minutes from downtown on a quiet residential street. Efficient use of space; the vaulted ceiling adds an element of spaciousness to the living area and the low maintenance hardwood like flooring adds to the appeal. The home features a sunroom to the back that offers an opportunity for an indoor garden, craft or wax room, or a quiet spot to finish a book. The gas

  Gary Fowles LivOregon Real Estate LLC

  343 NW Georgia Ave, Bend, OR 97701
• 

  

  /37

  Est $883,755 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,615 Sq Ft

  512 NW Delaware Ave, Bend, OR 97701

  512 NW Delaware Ave, Bend, OR 97701
• 

  

  /34

  $877,000

  • 4 Beds
  • 1 Bath
  • 1,697 Sq Ft

  145 NW Jefferson Place Unit 1, Bend, OR 97701

  Turn-key mill era home on an elevated lot! Located between downtown and the Old Mill, this property boasts one of Bend's best locations, just blocks from Miller's Landing and Drake Park. This home falls outside the regulatory boundaries of the Historic District, and features ample off-street parking.The well-maintained home has an updated kitchen and bathroom and beautifully refinished original

  Nick Berrey Nicholas Berrey

  145 NW Jefferson Place Unit 1, Bend, OR 97701

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