Hillsdale Real Estate

Welcome to Hillsdale, a charming and vibrant subdivision nestled in the heart of Portland, Oregon. Known for its picturesque scenery and community spirit, Hillsdale offers a unique blend of suburban tranquility and urban convenience, making it a sought-after destination for families, young professionals, and retirees alike.

One of the highlights of Hillsdale is its lush, tree-lined streets and well-maintained parks, providing residents with ample opportunities for outdoor activities. The area is home to the beloved Hillsdale Park, where children can play, families can picnic, and neighbors can gather for community events. The nearby Gabriel Park adds to the recreational options, featuring sports fields, walking trails, and a dog park, ensuring that there’s something for everyone to enjoy.

Hillsdale boasts an eclectic mix of local shops, cafes, and restaurants, creating a vibrant community atmosphere. From artisanal bakeries to cozy coffee shops, residents can savor a taste of Portland’s renowned culinary scene right in their own neighborhood. The Hillsdale Farmers’ Market, held weekly, showcases fresh produce and handmade goods, allowing locals to connect with their neighbors while supporting local artisans.

Education is a priority in Hillsdale, with access to highly-rated schools and educational institutions, making it an ideal place for families. The community is also conveniently located near major highways and public transportation, providing easy access to downtown Portland and beyond.

Whether you’re looking to buy your first home or find a serene place to retire, Hillsdale offers a welcoming environment that feels like home. Discover the charm and community spirit of Hillsdale – where your dream lifestyle awaits!

Newest Listings in Hillsdale

$649,900

4 Beds ⋅ 2 Baths ⋅ 209501703 MLS

Bright, move-in ready home in Hillsdale on 7500 sf lot with a basement apartment for guests or extra income. This unique property features a home with three bedrooms and 1.5 baths on the main and upper floors. It also has a money-making apartment in the basement with its own deck and entrance. Lots of updates in the last few years including new exterior paint in August 2026. Conveniently located in Hillsdale, this property won't disappoint. Basement unit rents for approximately $2400/month. Come visit today! [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10251428]

2226 SW IOWA ST, Portland

$774,900

4 Beds ⋅ 3 Baths ⋅ 549236115 MLS

Terrific two level home with primary bedroom on main floor with no steps from garage to main level. This charming home has been exceedingly well taken care of and most all systems as well as the living area are recently updated. Engineered hardwood floors across the main level, with a west facing formal living room with a two sided masonry fireplace which also opens to the dining room. The dining room has a sliding door which opens to a spacious covered deck. The updated kitchen with custom cabinets, quartz counters and stainless appliances including an induction cooktop sits off the side of the dining room. The main level also has three bedrooms, including the primary suite complete with full bath, plus another full bathroom on the same floor. The lower level has a lockable sliding door access to outside, one additional bedroom and a full kitchen and even its own electric meter! Lots of storage, along with new furnace 2026, central AC 2025, kitchen updated in 2007, main floor bath 2024, empire pacific windows 2007, R59 insulation 2025, main water line 2023, two electrical panels 2007, and much much more. All this close to Hillsdale, schools, and downtown Portland. Basement apartment is NOT a legal ADU.

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.