OVERLOOK Homes for Sale

OVERLOOK Homes for Sale

Welcome to Overlook, a charming subdivision nestled in the heart of Portland, Oregon, within the vibrant Multnomah County. This delightful community is known for its unique blend of urban convenience and serene residential living, making it an ideal place for families, professionals, and anyone looking to enjoy the best of what Portland has to offer.

Overlook boasts a rich history and a diverse array of homes, showcasing architectural styles that range from classic bungalows to modern townhouses. The neighborhood is characterized by its tree-lined streets, inviting parks, and community spirit, where neighbors become friends and gatherings are a regular occurrence. With a variety of homes for sale, Overlook provides options for every lifestyle and budget.

Residents of Overlook enjoy easy access to Portland’s extensive public transportation system, making commuting a breeze. The nearby Max Light Rail offers a quick route to downtown Portland, while local shops, cafes, and restaurants are just a short stroll away. For outdoor enthusiasts, the picturesque Overlook Park provides ample green space for picnics, jogging, and enjoying the stunning views of the city skyline.

Currently, there are several homes for sale in Overlook, each offering its own unique charm and features. Whether you’re seeking a cozy starter home or a spacious residence for a growing family, you’ll find a welcoming space that feels just right. Embrace the opportunity to become part of this vibrant community and discover your dream home in Overlook today!

Newest OVERLOOK Homes for Sale

1635 N JESSUP ST, Portland
$650,000
4 Beds ⋅ 3 Baths ⋅ 482883887 MLS
This updated old Portland home in the prized Overlook neighborhood is dialed and move-in ready. The formal entry sets the tone with high ceilings and hardwood floors. The living room features crown molding and a large south facing window that brings in all the light. A classic arch separates the living room from the dining room, which flows into an updated 6+ butt kitchen- perfect for cooks and entertainers. Each floor has bedrooms and bathrooms creating an overall floor plan that is classic and flexible. The main floor large bedroom is attached to a full bathroom which can also be accessed from the mud room. A 2015 renovation updated the electrical, plumbing, windows and roof, and opened up the upstairs into a private, spacious primary suite with 4 closets, south facing windows and its own bathroom. With 4 closets, south facing windows and an attached bathroom, it's a perfect sanctuary. The finished basement has high ceilings, 2 bedrooms with large egress windows, a family room and the third full bathroom. A recent glow-up added fresh interior paint, warm LVP flooring in place of carpet and energy efficient mini splits. The oversized lot with a garage offers lots of opportunities for gardens, pets and a detached ADU. The coveted Overlook location has an 80 walk score and a 100bike score making this spot the perfect home for easy access to grocery stores, coffee shops, restaurants, MAX and I-5. [Home Energy Score = 5. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10252835]

1635 N JESSUP ST, Portland
5735 N DETROIT AVE, Portland
$659,000
3 Beds ⋅ 1 Baths ⋅ 533122507 MLS
Welcome to this charming Overlook home where original craftsmanship, timeless character, and thoughtful updates come together beautifully in this Craftsman Bungalow. With 3 bedrooms, 1.5 bathrooms, and 2,084 square feet, this home showcases extensive original woodwork, custom built-ins, wood wainscoting, hardwood floors, and detailed millwork that give it warmth and character. The updated eat-in kitchen features quartz countertops, island, gas range, pantry, and plenty of workspace for everyday living and entertaining. A gas fireplace adds a cozy touch on chilly mornings and winter evenings, while double-hung Marvin windows provide excellent comfort, quiet, and flexibility for ventilation, privacy, and airflow. The finished lower level includes a non-conforming bedroom and half bath, ideal for guests or a home office.Step outside and discover a beautifully landscaped, private backyard. Solar lighting highlights the flower beds and mature trees, creating wonderful evening ambience for entertaining or relaxing outdoors. The inviting front porch is equally special- a peaceful spot to settle in with a cup of coffee, watch the neighborhood transition into evening, and enjoy the changing seasons. A detached garage and central air conditioning add everyday conveniences. Ideally located near neighborhood restaurants, parks, transit, and the vibrant N Portland community, with easy access to Adidas and downtown. A truly special Overlook home where original craftsmanship, inviting outdoor spaces, and the comforts of modern living come together. [Home Energy Score = 3. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10204102]

5735 N DETROIT AVE, Portland
2021 N SUMNER ST, Portland
$739,900
3 Beds ⋅ 2 Baths ⋅ 128446476 MLS
Located in the fabulous OVERLOOK neighborhood within walking distance to Adidas and Kaiser Permanente .Don't forget the Porch Festival, exclusive to the Overlook neighborhood and sooo fun! Total restoration of this beautiful foursquare. Modern Sarto French doors walk out to the new decks with contemporary privacy screens. Enjoy the deck that overlooks the large yard, ideal for an ADU. (check with the city) Among the things not visible to the eye but so important - Foundation retrofit, new electrical service and plumbing. Refinished natural wood floors gleam when you walk into the stunning kitchen with new cabinets, stainless gas appliances and quartz countertops. Kitchen opens to the great room and French doors leading outside. Convenient for El Fresco dining. The added bathroom in the primary suite with double sinks and a walk-in shower is the cherry on top. All work was permitted, and final inspections have been obtained. CENTRAL AIR WITH 2 NEW HVAC UNITS, ONE FOR UPSTAIRS AND ONE FOR THE MAIN LIVING AREA. NEW ROOF 09/2026/. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10235325]

2021 N SUMNER ST, Portland
4222 N MONTANA AVE, Portland
$565,000
3 Beds ⋅ 2 Baths ⋅ 396520532 MLS
Urban Living with Room to Spread Your Wings in Overlook!People, this one has WINGS! With easy access to I-5 North and South, just a couple blocks from vibrant Mississippi District, and nestled in the heart of Portland’s Overlook neighborhood, this home puts you close to all the urban hotspots. Built in 2011, this beauty offers the bonus features that make city living even better, starting with a detached garage/off-street parking! Street parking is available, too, making room for you and your guests.Step outside and enjoy a fenced backyard with space for gardening, entertaining, and relaxing. Out front, a generous west-facing porch is the perfect spot to soak up the evening sun and enjoy the pulse of the neighborhood.Inside, you’ll love the thoughtfully designed, flexible floor plan. The living and dining areas flow around a central kitchen that opens to a versatile bonus space featuring a fireplace and a large slider leading straight to the backyard. Whether you’re hosting friends or enjoying a cozy night in, this home makes it easy to spread out and settle in.The second floor offers a spacious primary suite with room for a king-sized bed, a large closet, and a dedicated nook perfect for a home office or vanity. The ensuite bath features a convenient tub/shower combination. Two additional bedrooms, a full hall bath, and a laundry area with washer-dryer included complete the second floor.And just when you think you’ve seen it all, zip up to the third floor! This extra bonus space is ready for whatever you dream up: movie nights, a home office, yoga studio, creative retreat, or all of the above. A third-floor bonus space like this is a rare find in newer homes!Whether you’re looking for a home to call your own or thinking about teaming up with friends to make homeownership more attainable, this one deserves a closer look.Time’s a-wasting! Spread your wings, embrace the Overlook lifestyle, and make this home yours. Why rent when you can combine forces and own? [Home Energy Score = 5. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10221464]

4222 N MONTANA AVE, Portland
3915 N Montana AVE, Portland
$440,000
3 Beds ⋅ 1 Baths ⋅ 516217245 MLS
Craftsman bungalow in Overlook: A Fixer with endless potential. 3 bedrooms and 1 bath. Unfinished basement for possible additional living space. There is a detached 1 car garage with alley access!Possible ADU. Buyer to due own due diligence. Convenient to Kaiser hospital downtown Portland,Overlook Park the Maxline, I-5 freeway, lot's of shops and restaurants. Bring your builders & developers. Don't miss this incredible opportunity!

3915 N Montana AVE, 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.

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