5 Homes for Sale in Milwaukie for Under $500,000

The secret seems to be out that Milwaukie is one of the coolest up-and-coming spots in the Portland area. (You’ll often hear this technically separate city described as Portland’s little sibling, or “basically part of Portland.”) And it’s true – there’s a lot to love. River access, an excellent farmer’s market, and a small but thriving downtown all add to the charm.

One of the best ways to approach your home search is to locate a handful of neighborhoods that you’re most interested in. On our site, you can search by city, zip code, school or county. And then narrow your search from there using any number of our Vestor Filters! Since new homeowners continue to be attracted to Milwaukie, today we’ll check out five of the most promising properties in Milwaukie – all with list prices under $500,000.

#1 – 3670 SE Hill Rd.


With 6 bedrooms – 4 in the main house and 2 on the upper floor, which has its own entrance – this home is an excellent opportunity for anyone looking to expand! There’s potential for multi-family or multi-generational living. Plenty of amenities are in walking distance, or take a drive out of the 2 car garage.

You won’t find a ton of luxury updates in this home (although you could certainly change that), but one of the most exciting parts of this home is the yard and view. From the huge, nearly .25 acre yard, enjoy views of the city lights in the valley from your own quiet retreat. A large deck with a pergola sweetens the deal, while still leaving plenty of space for gardening or other projects.

#2 – 12437 SE Alchar Dr.


This lovingly maintained Daylight Ranch style home sits on a 1/3 acre lot in a cul-de-sac, ensuring plenty of space and privacy. A Daylight Ranch indicates that the home is built on a slope, meaning you will typically see more than one story on one side. This increases your square footage and your sunlight – hence the name. The original 1955 hardwood floors will welcome you in to sit before a gas fireplace. Or, if you prefer spending time outside, you’ll find the yard has plenty of room for multi-level gardening. And when it’s time for lounging, grab a seat on the concrete patio or on the second floor deck.

Don’t worry that you’ll be totally secluded, though – despite the quiet street, you’ll be just steps from downtown Milwaukie’s restaurants and shops as well as the beauty of Kellogg Creek.

#3 – 4116 SE Wake Ct.


This is a truly move-in ready home, complete with updates throughout. We’re talking the necessities – siding, water heater, etc. – but also nice touches inside such as new moulding, cabinets and appliances. You’ll reap the benefits of all these new touches while still enjoying the lived-in charm of a warm fireplace. Outside, the large yard includes mature trees, providing shade and privacy. A shed on site also means there’s plenty of room for your projects.

This part of Milwaukie is quiet and full of families. But just to the south downtown Milwaukie awaits – or, cross McLoughlin Boulevard and head into Sellwood for even more urban amenities.

#4 – 5050 SE Weeks Ct.


Don’t let quaint Milwaukie fool you – you can still find homes with a little more sass and panache. This home, for example hides some secret luxury inside. The main level bathroom is glorious, with an elegant soaking tub as well as a walk-in shower. Your gourmet kitchen comes with a gas range and all the high end appliances you can expect.

Thinking of entertaining? In the living room, gather around a stately fireplace with a mantle. Or enjoy the covered outdoor dining area, from which you can hear the babbling brook sounds of the built-in water feature. A shed, deck, fire pit, and well-maintained landscaping complete the package. And a two car garage and plenty of outdoor parking space ensure you’ll have all your storage needs met.

#5 – 16699 SE Oatfield Rd.


Here we find another Daylight Ranch style home. And as you can see from the above photo, it certainly gets its share of daylight. This home is ideal for anyone looking for a lot of storage space. With several parking pads, you’ll have plenty of room for an RV, or any other favorite vehicular toys. Store your projects in the large utility room, which provides plenty of space for hobbies. Or, the aspiring gardener will find a home for tools and supplies in the separate garden shed.

This home is the furthest south on this list, moving more towards Gladstone. There’s no doubt it’s a quiet neighborhood. But one of the most delightful aspects of this home is its views of Portland. The city will still live with you, and only a short drive away. With ADU potential, the possibilities for living here are expansive.

Let’s Go Check Them Out Together

If you’re ready to find the top Portland homes for sale, you’ve come to the right place. Call us at 503-773-0000 to find out more or schedule a tour.

Meanwhile, check out our search tools to streamline the journey of finding your new home. For this article, we searched for homes in Milwaukie and sorted through the listings by choosing a price cap of $500,000. Whatever neighborhoods are calling to or specific needs you have, our filters can help you find the perfect home for you.