Timeless Eastmoreland opportunity. Built in 1937 and owned by the same family since 1971, this classic home is ready for its next chapter. Only the third owner since construction, the property has incredible potential for restoration and modernization.The home offers more than 3,300 sq ft with a floor plan that checks every box: a large living room with hardwood floors, arched openings, and a wood-burning fireplace; a formal dining room; and a vintage kitchen with an adjoining breakfast nook overlooking the tree-lined street. The main level includes a bedroom and full bath for guests or flexible living. Upstairs are three generously sized bedrooms, a full bath, and an office or bonus space—an ideal layout rarely found in homes of this era. The lower level adds a finished family room, laundry area, workshop, and additional bath.This home needs extensive updating but offers a solid structure, abundant natural light, and architectural character throughout. Situated in one of Portland’s most beloved neighborhoods, close to Berkeley Park, Eastmoreland Golf Course, and the shops and restaurants of Sellwood and Woodstock. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10242432]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$545,000 (USD)
Portland Area Residential
Sold
5517 SE Boise St Portland, OR 97206
3 Bed
3 Baths
2274 sqft
This is the “House Hack” you’ve been waiting for. Yes, you really can have a home that pays you to live there.Above grade you’re getting a true 3 bedroom, 2 bath home with its own dedicated laundry, generous room sizes, great ceiling height, and the warmth of original fir floors. The main level features a fantastic primary bedroom with double closets, updated flooring throughout, and spaces that feel open, comfortable, and lived-in the right way. Off-street parking, a large deck, and a spacious yard give you room to imagine your own outdoor retreat.And then there’s the bonus. The finished basement is a fully independent lock-off unit with its own entrance, its own outdoor living nook, and a beautifully designed kitchenette. It’s ideal as an income producing rental or a private guest suite—already leased and performing.This 1911 Craftsman sits right in the heart of the Foster-Powell corridor, minutes from Woodstock and everything you love about Southeast Portland. Smart layout, character, and cashflow potential all in one. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10242630]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$550,000 (USD)
Portland Area Residential
Sold
2545 NE 37th Ave Portland, OR 97212
2 Bed
2 Baths
2094 sqft
Tucked into one of Northeast Portland’s most picturesque neighborhoods, this 1925 Bungalow captures the best of Portland charm and community. The tree-lined streets, top-rated schools, and proximity to local favorite hotspots make everyday living feel effortlessly connected.Inside, the home is warm and inviting, with sun-filled rooms, original hardwood floors, and a classic brick fireplace surrounded by built-ins. The kitchen blends modern functionality with vintage character, featuring butcher-block counters, open shelving, and a farmhouse sink that anchors the space. A cheerful dining nook opens through French doors to a private courtyard—perfect for morning coffee or intimate outdoor dinners.Each of the three bedrooms is thoughtfully placed on its own level, offering comfort and separation of space. The upper floor provides a cozy hideaway under vaulted ceilings, while the main level bedroom sits adjacent to a tastefully remodeled bath with designer tile and black-framed shower glass. The finished lower level includes a spacious bedroom, sitting area, kitchenette, and full bath—ideal for guests, multi-generational living, or creative use.A detached studio with vaulted ceilings and skylights completes the picture, offering endless flexibility for a home office, art space, or gym. Just minutes to Beaumont Village, Grant Park, and local schools, this home combines timeless design with the heart of Portland’s beloved eastside lifestyle. [Home Energy Score = 2. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10242318]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$717,500 (USD)
Woodstock Area Residential
Sold
5211 SE 49th Ave Portland, OR 97206
4 Bed
3 Baths
1741 sqft
Perfectly situated on a quiet residential street just half a block from Woodstock Park and Elementary School, this home stands out for its modern convenience and thoughtful upgrades rarely found in the neighborhood.The home was pre-inspected and found nearly flawless, a true reflection of the care and investment the sellers have made. Major improvements include a newer roof, updated mechanical systems, and elevated details throughout with upgraded doors, millwork, and hardware.Inside, the kitchen is beautifully appointed with quartz counters, a Blanco sink, premium appliances, and high-end fixtures. The open, light-filled floor plan immediately welcomes you with real oak hardwood floors and a cozy gas fireplace as the centerpiece.The main floor bedroom and full bath add flexibility for guests, multi-generational living, or home office. Upstairs, the spacious primary suite offers a large walk-in closet and custom built-ins framing a bay window retreat. With three bedrooms and two full baths on the upper level, this floor plan is among the most sought after in the area.Outside, enjoy a full-sized manicured lot, a large attached garage, and a neatly placed, secure storage unit in the backyard, perfect for outdoor gear or seasonal items.This home combines the timeless appeal of Woodstock living with the comfort, efficiency, and reliability of modern construction, making it an exceptional find in one of Portland’s most beloved neighborhoods.
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$492,500 (USD)
Portland Area Residential
Sold
8236 N Olympia St Portland, OR 97203
3 Bed
2 Baths
2012 sqft
Wouldn't it be great to own a home that pays you to live there? This one does!Unlike so many listings that boast ADU potential, this North Portland bungalow already has a fully permitted ADU complete with a long-term tenant providing steady income. The ADU is approximately 540 square feet and features one bedroom, one full bathroom, and an open kitchen and living room that feels bright and inviting.The main home includes two bedrooms, one bathroom, and an unfinished basement ready for your expansion ideas. The kitchen is fully appointed with a dishwasher and is large enough for an eating area, opening directly to the living room for a comfortable flow. At the rear of the home, a convenient mudroom connects to the carport for easy everyday access.Outside, enjoy a private, fenced yard with a mature apple tree and off street parking under the carport. Thoughtfully designed, the property lives like two separate homes, offering comfort, privacy, and flexibility in a terrific North Portland Neighborhood! [Home Energy Score = 4. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10242659]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$650,000 (USD)
Milwaukie Area Multifamily
Sold
9508 SE 43rd Ave Milwaukie, OR 97222
5 Bed
3 Baths
2009 sqft
This Milwaukie duplex truly lives like a home. The three-bedroom side features a spacious primary suite with a walk-in closet, creating a comfortable retreat for everyday living. Each residence is designed with privacy in mind, with family rooms that open onto individual patios and a two-car garage divided for secure, personal storage. The oversized lot provides a sense of space that’s rare to find in this type of property, making it ideal for those who want the benefits of home ownership while generating income from the adjoining unit.Beyond the property itself, the setting is just as compelling. Milwaukie has undergone an exciting downtown revival, now home to multiple breweries, a vibrant farmers market, and an energy that continues to grow. With excellent public transit options, quick access to Sellwood, and an easy connection to downtown Portland, this location balances neighborhood charm with urban convenience.With estimated rents grossing $4,000 a month, low Clackamas County taxes, and efficient all-electric systems with separate meters, this is more than just a place to live, t’s a chance to invest in both lifestyle and long-term opportunity. [Home Energy Score = 4. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10242316]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$455,000 (USD)
Gresham Area Residential
Sold
21339 SE Alder St Gresham, OR 97030
3 Bed
2 Baths
1692 sqft
Nicely maintained 1968 ranch-style home with a two-car attached garage, set on a large private lot. The spacious floor plan includes a formal living room anchored by a classic Roman brick fireplace and a large picture window that fills the space with natural light. The kitchen opens to a comfortable family room featuring a pellet stove, skylight and French doors that lead to a covered patio—perfect for year-round enjoyment.A formal dining room showcases original hardwood floors, while three generously sized bedrooms all include large closets. A coveted second bathroom adds convenience and value.This cleam move in ready home is a terrific opportunity in a quiet, well-kept neighborhood with quick access to both Gresham and Portland.
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$689,000 (USD)
Portland Area Residential
Sold
5536 N Delaware Ave Portland, OR 97217
3 Bed
3 Baths
2584 sqft
Step into timeless charm and sophisticated craftsmanship with this 1924 Dutch Colonial boasting 2,584 square feet of character-rich living space. Ideally situated in one of the city's most vibrant neighborhoods, Overlook! You'll be just moments away from a bustling mix of restaurants, grocers, drinkeries, coffee shops, public transit, and local bodegas.Inside, the home offers three spacious bedrooms on the upper level and a warm, inviting main floor anchored by a classic wood-burning fireplace. The home is heated with a gas furnace for year-round comfort. The flooring throughout is a rare and artistic treasure—an eclectic mix of handcrafted parquet designs. From the intricate basket weave pattern on the main floor to the herringbone and traditional inlays upstairs, each room offers a nod to timeless European craftsmanship.The walk-up attic provides an additional 200 square feet of untapped potential—perfect for a home office, creative studio, or cozy retreat. Downstairs, the basement is nicely set up and offers excellent potential for a variety of ADU (Accessory Dwelling Unit) configurations, giving you flexibility for extended living or income-generating opportunities.Out back, the sunny yard invites you to garden, relax, or entertain with its generous deck, raised planter beds, and direct access to the attached garage.This is more than a home—it’s a piece of Portland history with unmatched style, modern comfort, and exciting potential in an unbeatable location! [Home Energy Score = 2. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10238882]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$867,000 (USD)
Portland Area Residential
Sold
2322 NE Clackamas St Portland, OR 97232
5 Bed
2 Baths
4070 sqft
This 1909 Foursquare home embodies character, and quality craftsmanship. Nestled in the close-knit Sullivan's Gulch neighborhood, it offers a prime location with convenient access to nearby amenities. Thoughtfully designed with over 4,000 square feet, the generous floor plan provides a wonderful sense of space while maintaining a warm atmosphere. Large windows fill the home with natural light, highlighting beautiful details such as box beam ceilings and built-in benches that add both function and charm. The main floor features quality oak hardwoods, tall ceilings, and elegant moldings. The kitchen includes an eating area, gas cooking, and French doors leading to the backyard deck. Upstairs, the second floor offers four spacious bedrooms with hardwood floors, including a large primary that boasts a versatile sitting room opening onto a delightful sun porch (historically known as a consumption room)—the perfect spot for morning coffee or evening relaxation. The third floor offers a spacious fifth bedroom and a flexible open area, ideal for a variety of uses.Thoughtful updates, including earthquake retrofitting, a decommissioned oil tank, and modernized systems, provide peace of mind. Tons of storage in the unfinished basement and large detached garage!This home has been under careful stewardship for six decades. Now, it’s ready for its next owner to appreciate its timeless appeal and exceptional setting. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10214749]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$741,850 (USD)
Portland Area Residential
Sold
3801 NE Rosa Parks Way Portland, OR 97211
3 Bed
2 Baths
2556 sqft
Fall in love with this vintage mid-century modern home located on a quiet residential street, just blocks from Fernhill Park, the Dekum Triangle, the Kennedy School Brewpub & Theater, the Alberta Arts District, and the University of Oregon’s Portland campus. With over 2,500 square feet, this home offers spacious main-floor living with three bedrooms, large windows that flood the interior with natural light, and effortless flow to beautifully landscaped outdoor spaces.Set on an oversized lot with mature landscaping, the property offers both privacy and charm in the Concordia neighborhood’s Van Laeken Modern subdivision—a quiet enclave known for its architect-designed mid-century modern homes with Roman brick facades—this home blends timeless design with convenient access to the best of Northeast Portland. Enjoy nearby amenities like Fernhill Park’s off-leash dog area and summer concerts, New Seasons Market, and an array of local restaurants and coffee shops along NE 42nd, Fremont, Dekum, and Alberta.Inside, you’ll find hardwood floors throughout and a spacious basement featuring a second brick fireplace and a stylish 1950s cocktail lounge vibe. As a special perk, Concordia residents receive complimentary access to the soaking pool at the Kennedy School. [Home Energy Score = 4. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10199930]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$765,000 (USD)
Portland Area Residential
Sold
4734 N Williams Ave Portland, OR 97217
4 Bed
3 Baths
2403 sqft
This turn-of-the-century Victorian offers timeless charm with an income twist! Featuring a coveted floor plan! The second floor boasts three generous bedrooms and a spacious bath, while the main floor includes a den (or optional 4th bedroom), along with expansive dining and living rooms. A formal entry welcomes you into a home adorned with classic Victorian woodwork, fir floors, and recently refreshed kitchen and baths. The unfinished basement offers excellent ceiling height, a half bath, and laundry, providing potential for additional living space. Outside, a large backyard complements the standout feature—an incredible 1,400 sq. ft. garage, partitioned into four separate rental bays generating $845 per month, while still maintaining a private attached bay for the home. Which has been separately rented for $299.00 a month.Located in one of the Eastside’s hottest neighborhoods, this is a rare opportunity to enjoy vintage elegance, prime location, and built-in income potential to help offset mortgage rates and check out the super low taxes! The best opportunity and value on the Eastside! [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10236260]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$615,000 (USD)
Alberta Arts Concordia Area Residential
Sold
5805 NE 30th Ave Portland, OR 97211
3 Bed
2 Baths
3156 sqft
You will fall in love with this very "pure" 1913 Craftsman Bungalow that features all of the Arts & Crafts adornments you could dream of, with unpainted woodwork, amazing corbels, wainscoting, large scale moldings & extensive built-ins. This 3 bedroom home offers over 3100sf, an unfinished basement, 2 full baths and a original fireplace. The location is a 10/10, just steps from the Kennedy School, New Seasons & all that Alberta & Concordia has to offer! Hurry on this one! [Home Energy Score = 2. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10185265]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$599,000 (USD)
Alberta Arts Area Residential
Sold
5230 NE 28th Ave Portland, OR 97211
5 Bed
2 Baths
2964 sqft
This outstanding 1912 Craftsman offers over 2900sf in the vibrant Alberta Arts neighborhood's best location, surrounded by the legendary Shops, Coffee houses, bars, eateries & Grocers! This home has been extensively upgraded in the last 2 years with new exterior siding, seismic strapping, windows $ a full length front porch to greet your guests at the door! The home is heated with a new dual gas furnace system with AC on the 2nd floor & rare floor plan with 4 bedrooms upstairs! Great value! [Home Energy Score = 3. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10184162]
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust
$569,900 (USD)
Portland Area Multifamily
Active
6204 NE 8th Ave Portland, OR 97211
6 Bed
2 Baths
2226 sqft
MLS# 600196381
This is a single family home with a permitted ADU in the basement and it is the “house hack” you’ve been waiting for. The rental income cant help offset your mortgage! What makes this property so unique is the layout. The property lives as two separate and highly functional 3 bedroom, 1 bath spaces…a setup the market is actively looking for right now.Above grade, you’re getting a warm and character filled 3 bedroom, 1 bath home with beautiful oak and maple hardwood floors, generous room sizes, excellent natural light, and an open, functional kitchen designed for everyday living. The spaces feel comfortable, timeless, and authentic to the neighborhood, blending classic Portland charm with thoughtful updates throughout the current ownership.And then there’s the bonus.The lower level features a fully permitted 3 bedroom, 1 bath ADU with its own private entrance, impressive ceiling height, and a surprisingly bright and open floor plan. The projected market rent for the lower level unit is estimated around $1,800 per month, creating exceptional flexibility whether you’re looking for supplemental income, multigenerational living, guest quarters, or long term investment potential.Outside your door is one of Northeast Portland’s most loved locations, right near the Dekum Triangle between Ainsworth and Dekum with incredible restaurants, coffee shops, pubs, and neighborhood destinations just moments away.Smart layout, historic character, and real income potential all in one property.
Listing Courtesy of RMLS / Listed By: Joe Spanish, Windermere Realty Trust