Milwaukie, OR Real Estate Search

Milwaukie, OR 5 Bedroom Homes for Sale

Milwaukie, OR, offers a diverse selection of spacious 5-bedroom homes that cater to families and individuals seeking both comfort and style. The real estate market in this charming suburb, located just a short drive from downtown Portland, features a variety of architectural styles, from contemporary designs to classic Craftsman homes. Many of these properties boast large backyards, perfect for outdoor gatherings and recreation, while interiors often include modern amenities like open-concept layouts, gourmet kitchens, and updated bathrooms. With a vibrant community atmosphere, excellent schools, and convenient access to parks and local shopping, Milwaukie presents an attractive option for those looking to settle in a family-friendly environment with plenty of room to grow.

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Newest Milwaukie, OR 5 Bedroom Homes for Sale

$649,500
5 Beds ⋅ 3 Baths ⋅ 255107374 MLS
Stunning & spacious daylight ranch, situated on an expansive manicured lot with over 3,044 sqft. of living space, this home boasts 5 bedrooms, 3 bathrooms, living room, dining room, family room and an updated kitchen with pantry & eat area. Kitchen updates include: luxury vinyl plank flooring, stainless steel dual basin sink, white maple cabinets, quartz countertops, garbage disposal, stainless steel "Frigidaire Gallery" appliances package that includes built-in; refrigerator, range, microwave & dishwasher. Additional features include: new carpet throughout, en-suite primary bedroom, formal dining area with beautiful views of the park-like backyard, Inviting living room with a wood burning fireplace and a slider that opens to a covered deck overlooking the gorgeous backyard. Lower level family room has beautiful built-in bookcases, a woodstove, a slider to the covered backyard patio. Property grounds are magnificent & include a large outdoor patio space, a tool shed, and an area for planting/growing your own produce. Additionally the lower level has an oversized laundry/crafts or sewing space with luxury vinyl flooring & hookups for your washer & dryer. Also on the lower level is a sizable mechanical/storage room with adequate hobby/workspace including a doorway to the backyard & patio. The attached 2 car garage includes affixed storage racks for conveniently stowing all your favorite holiday decorations. This incredible home is both thoughtfully crafted and well cared for & it's certain to meet all your needs... and best of all it's MOVE-IN READY!!!

14354 SE CAROL AVE, Milwaukie
$685,000
5 Beds ⋅ 3 Baths ⋅ 216357782 MLS
OPEN HOUSE SUN 12-2PM 5 bedrooms, 3 full bathrooms, 2 kitchens, and a fully equipped ADU with its own private entrance — this Jennings Lodge/Milwaukie property offers unbeatable flexibility for multi-generational living or rental income.Beautifully updated throughout, the home features spacious, light-filled living areas with large newer windows, an open layout, and thoughtful upgrades that make it move-in ready. The ADU is wheelchair accessible with its own entrance, providing wide access points and comfortable single-level living.Enjoy the outdoors year-round on the large covered back deck, overlooking two separately fenced backyards—perfect for giving both the main home and ADU their own private outdoor spaces.Major improvements add peace of mind, including a new roof in 2020, newer HVAC, and refreshed interior updates throughout.Located in the desirable Jennings Lodge community, this home offers incredible versatility, modern comfort, and endless possibilities. Homes with this level of function and flexibility don’t come up often—don’t miss it!

5625 SE CLAYSON AVE, Milwaukie
$650,000
5 Beds ⋅ 2 Baths ⋅ 720257235 MLS
Why choose between buying a home and beginning your investment journey when you can explore the possibilities of both? This inviting duplex offers a unique opportunity to move into the vacant 1-bedroom, 1-bath unit while the 3-bedroom, 1-bath unit is currently tenant-occupied. The 1-bedroom unit comes fully furnished and features a new mini-split system, making it comfortable, convenient, and truly move-in ready. Both units offer light-filled interiors, a clean and welcoming feel, and thoughtful updates throughout. Outside, the large lot provides plenty of room to enjoy, while the two-car garage offers valuable space for parking, storage, or a workshop. Whether you're looking for a home or an investment, this versatile property offers flexibility, existing tenancy, and strong future potential.

5411 SE THIESSEN RD, Milwaukie
$1,675,000
5 Beds ⋅ 2 Baths ⋅ 460695901 MLS
Prepare to fall in LOVE! This exceptional modern riverfront home blending sophisticated design with the natural beauty of the Willamette River.Expansive windows fill the open concept main level with natural light while framing serene river views. A striking gas fireplace with custom built-ins anchors the living space, which opens to a large deck perfect for entertaining, sunset gatherings, or relaxing above the water.The designer kitchen features a dramatic granite waterfall island, high-end appliances, under-cabinet lighting, and a spacious walk-in pantry. The main level primary suite is a true retreat with sweeping river views, a private fireplace, and a spa inspired bath featuring marble floors, a freestanding soaking tub, walk-in shower, and oversized closet.Ideal for entertaining or multigenerational living, the daylight lower level offers a spacious family room with a gas fireplace and wet bar complete with a wine refrigerator and second dishwasher. Double sliders open to a covered patio and backyard. Four additional bedrooms, a laundry room, and abundant storage complete the level.Two attached garages, including an oversized lower garage, provide exceptional flexibility. Private backyard access leads directly to the river, while a nearby public boat ramp makes boating and recreation effortless.With stunning finishes, versatile living spaces, breathtaking views, and an incredible connection to the water, this is modern Willamette River living at its finest.

19697 SE COTTONWOOD ST, Milwaukie
$680,000
5 Beds ⋅ 2 Baths ⋅ 259222247 MLS
Built in 2020 this one-owner home is move-in ready, minutes from downtown Milwaukie, less than 10 minutes from Portland, and boasts space for your RV or boat when you return from the river! Just inside is a main floor 5th bedroom with glass french doors providing flexibility for guests or work-from-home setup. Modern finishes are all throughout starting with the spacious, bright, kitchen with large island, stainless steel appliances, solid-surface quartz countertops, and walk-in pantry. The kitchen opens to a spacious, connected dining area framed by large windows. Tall ceilings carry into the open living room with natural gas fireplace and convenient built-ins. New, plush carpet carries you upstairs to 4 additional bedrooms including the Primary with ensuite. Coffered ceilings, large windows, walk-in shower, soaking tub, double sinks, and large walk-in closet are a Win. Covered patio, and a flat fully-fenced backyard provide an extension to your everyday living space. This home has it all!

14535 SE GARLAND LN, Milwaukie
$615,000
5 Beds ⋅ 2 Baths ⋅ 151534536 MLS
(Seller will contribute a generous amount toward buyer closing costs, a rate buy down, or both. Call to find out more) Spacious five-bedroom home, move-in ready! Two primary suites — one on each level — plus a first-floor den offer flexible living. Open dining room, living room, and kitchen flow together, while the family room features a gas fireplace with built-ins and a display niche. Large deck overlooks the private, fenced backyard with a shed. Newer roof (2018) and brand-new AC (2025). RV parking. Don't miss this one — schedule your showing today!

5234 SE ALDERWAY AVE, Milwaukie
$684,960
5 Beds ⋅ 2 Baths ⋅ 400016119 MLS
Welcome to this stunning newer-construction home nestled in a quiet Milwaukie neighborhood! Situated on a fully fenced 7,000 sq ft lot, this property offers both privacy and space to relax or entertain. Inside, you’ll find engineered hardwood floors throughout the main level and a thoughtfully designed open layout that blends comfort and style. The kitchen features quartz countertops, professional-grade stainless steel appliances, and custom cabinetry. Upstairs, you will find the vaulted primary suite with walk-in closet, soaking tub, and walk-in tile shower. A 3-car garage provides ample storage and parking. This home is equipped with central air conditioning and gas tankless water heater!

14047 SE PIPER CUB WAY, Milwaukie
$997,000
5 Beds ⋅ 4 Baths ⋅ 270521960 MLS
Step back in time and discover the timeless beauty of this extraordinary 1928 classic, offered for the first time in over 80 years. Situated on a rare and private one-acre lot, this 4,464 square foot home is filled with original character and endless potential for the next owner to restore and reimagine.Inside you will find stunning original hardwood floors, beautiful leaded glass windows, and two charming wood-burning fireplaces that capture the craftsmanship and elegance of a bygone era. With 5 spacious bedrooms and 4 bathrooms, this home offers room for everyone while preserving the warmth and personality that make historic homes so special.From the grand living spaces to the incredible architectural details, this property is truly a once-in-a-generation opportunity. Whether you are looking to lovingly restore a historic treasure or create your dream estate, the possibilities here are endless.Homes like this rarely come available. Bring your vision and make this iconic property beautiful once again.

3921 SE LAKE RD, Milwaukie
$1,025,000
5 Beds ⋅ 3 Baths ⋅ 636541357 MLS
Rare opportunity to live and have income-producing potential in this Milwaukie Heights property in Clackamas County on a private 1.13-acre setting featuring a private attached apartment and the huge shop you have been searching for! A tree-lined, gated driveway leads to this peaceful oasis surrounded by mature trees and the cheerful sound of birds, where nearly every room enjoys views of nature. The huge garage and shop area is a dream for hobbyists, tradespeople, or entrepreneurs, offering RV and boat storage, dedicated workshop areas, and loft storage.Inside, the flexible layout includes six bedrooms, three with ensuite bathrooms, creating ideal spaces for family members or guests. The heart of the home features a chef’s kitchen with a Wolf gas range, built-in oven and microwave, large pantry, and breakfast bar. A bright solarium with skylights and an inviting living room with a gas fireplace fill the home with natural light and views of the surrounding trees and nature. The home also includes a large laundry room with built-in storage.The layout also works beautifully for multigenerational living, with one bedroom located within the private apartment suite featuring its own entry, living room, patio, full bath, and mini-split AC, ideal for extended family, guests, a home business, or potential rental income.Outdoor living shines with multiple patios, including a covered patio, raised planting beds, a predator-proof chicken coop with run, and a fully fenced yard with direct access to the greenbelt, creating a private, park-like setting. There is also plenty of space to host family reunions and gatherings, with room for tents, outdoor games, a fire pit, and abundant parking, all surrounded by the peaceful sound of birds and nature.With a roof installed in 2021, an updated electrical panel, a huge shop, flexible living spaces, income-producing potential, and a peaceful 1.13-acre setting, reach out for a showing of this Milwaukie Heights property!

16620 SE HAMPSHIRE LN, Milwaukie
$999,999
5 Beds ⋅ 4 Baths ⋅ 534238385 MLS
Stunning luxury estate. This fully updated 5,700 sq ft residence showcases extraordinary amenities and $200,000 in premium renovations. The highly functional floor plan includes 5 bedrooms and 4.5 designer-remodeled bathrooms, featuring quartz counter tops, upscale fixtures, and a spa-quality primary suite with a walk-in shower and freestanding soak tub. Rare life amenities elevate this home far above the market, including a resort-style indoor swimming pool, 30x35 sport court with NBA-grade hoop, and a complete turf yard transformation providing year-round, zero-maintenance curb appeal. Recent upgrades include all-new wood flooring, new carpet, fresh paint, shiplap ceilings, remodeled basement, and beautifully updated kitchen and bath finishes with quartz surfaces, high-end tile work, and modern lighting. A whole-home automatic generator powers HVAC, appliances, and upper level for seamless reliability---an invaluable feature during Oregon winters. Set on a flat, private .27 acre landscaped lot, this property offer exceptional spaces for entertaining, recreation, and family living. Ideally situated in a quiet, established Milwaukie neighborhood just minutes to parks, schools, shopping, dining, and quick I-205 access, this is truly a one-of-a-kind luxury estate offering unmatched amenities and value in the greater Portland area---perfect for families and entertainers alike.

6499 SE NORMA CIR, Milwaukie
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The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.