Hillsdale Real Estate

Welcome to Hillsdale, a charming and vibrant subdivision nestled in the heart of Portland, Oregon. Known for its picturesque tree-lined streets and a strong sense of community, Hillsdale offers a unique blend of suburban tranquility and urban convenience. This delightful neighborhood is situated in Multnomah County, just a stone's throw away from the bustling city center, making it an ideal location for those seeking the best of both worlds.

Hillsdale is characterized by its diverse architectural styles, ranging from cozy bungalows to contemporary homes, each reflecting the neighborhood's rich history and character. Residents enjoy a strong sense of belonging, with friendly neighbors and an active community association that hosts various events throughout the year. The area is also home to several parks, including the expansive Hillsdale Park, where families gather for picnics, sports, and outdoor activities.

One of Hillsdale's standout features is its thriving local business scene. The Hillsdale Farmers Market, held weekly, showcases fresh, locally-sourced produce and artisanal goods, creating a vibrant atmosphere for residents and visitors alike. Additionally, the neighborhood boasts a variety of cafes, restaurants, and shops, making it easy to support local entrepreneurs while enjoying a delightful day out.

With its excellent schools, convenient public transportation options, and proximity to major highways, Hillsdale is perfect for families, young professionals, and retirees alike. Whether you're looking to buy your first home, downsize, or invest in a rental property, Hillsdale offers a welcoming community with all the amenities you need to lead a fulfilling lifestyle. Come explore Hillsdale—where community spirit meets modern living!

Newest Listings in Hillsdale

$599,900

4 Beds ⋅ 2 Baths ⋅ 209501703 MLS

Updated Hillsdale home with a permitted separate apartment that can help offset your housing costs and/or provide additional living space. The house offers a remodeled kitchen and newly remodeled bathrooms, plus updates to plumbing, electrical, sheetrock, and insulation throughout. Exterior paint completed in August 2026 adds to the recent improvements.The basement apartment rents for approximately $2,400 per month and features its own entrance and deck, providing independent space for short-term renters or guests.Separate from the apartment, a spacious basement storage and utility area offers room for household supplies and seasonal belongings. An 8-by-12-foot shed with shelving provides versatile storage for bikes, tools, equipment, project materials, and more. A covered area enclosed on three sides adds sheltered storage space.Create the outdoor space that fits your life. Set on a 7,500-square-foot lot surrounded by trees in the heart of SW Portland’s Hillsdale neighborhood, the home offers unfinished yard space ready for your ideas, from vegetable gardens to a lawn, play area, or a place to relax outdoors. Hillsdale and Multnomah Village are very close making it easy to enjoy both neighborhoods' restaurants, cafés, breweries, groceries, and their abundant hiking trails and natural beauty. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10251428]

2226 SW IOWA ST, Portland

$699,900

4 Beds ⋅ 3 Baths ⋅ 549236115 MLS

Hillsdale mid-century modern is move-in ready! This is your opportunity to view this updated, well-taken care of home. One owner in the last 30 years, with lots of updating along the way! This home offers step-free access from the garage and across the main floor with gleaming engineered hardwood floors throughout. There is a dining room with fireplace and a sliding door to the deck, kitchen with new stainless appliances, an induction cooktop, custom built cherry wood cabinetry, and quartz countertops. The large deck off the dining room is covered. The living room faces west for views of evening sunsets. With a two-sided wood burning fireplace complete with crisp white bricks which opens to both dining and living rooms. Three bedrooms are on the main floor, all with engineered hardwood floors, the primary bedroom has its own full bath attached and there are two additional bedrooms and the main hall full bathroom with shower/tub combination. The lower level can be used in multiple ways to fit your needs; It can serve as a spacious family room, or as a separate apartment for caregiver, or an adult companion. It has its own lockable entrance and well-lit access up the stairs to the street as well as a cozy fireplace, space for table/desk, new LVT flooring, full kitchen, bedroom and even a full bath. The basement also has its own electric meter. This home has two large inside storage areas and an outside storage area as well. Sunny low maintenance backyard is perfect for your own vegetable/flower garden. Note high-quality new AC and furnace (2025/2026), new lighting fixtures throughout to include LED lights, new flooring, sinks, and countertops in the upstairs bathrooms (2024), R 59 insulation (2025) plus solar attic fan cutting energy costs considerably, updated electric panels (2), and newer water line to street too! All this and more with access to the level street, close to Hillsdale shopping, transit, schools, and minutes to downtown and Beaverton

5211 SW 19TH DR, Portland

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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.

Hillsdale Real Estate

Newest Listings in Hillsdale

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