OVERLOOK Homes with On Street Parking

OVERLOOK Homes with On Street Parking

Welcome to Overlook: A Hidden Gem in Portland, Oregon

Nestled in the vibrant city of Portland, the Overlook subdivision is a charming community that perfectly marries urban convenience with suburban tranquility. Known for its stunning views of the Willamette River and the majestic peaks of Mount Hood, Overlook offers residents a picturesque setting that’s hard to resist. This neighborhood is characterized by its tree-lined streets, friendly atmosphere, and a rich tapestry of architectural styles, from classic bungalows to modern townhomes.

One of the standout features of Overlook is its accessibility to a variety of amenities. Residents enjoy easy access to local parks, including the expansive Overlook Park, which boasts sports facilities, playgrounds, and beautiful walking trails. The area is also well-connected to public transportation, making it a breeze to explore the rest of Portland’s eclectic neighborhoods, vibrant dining scene, and cultural hotspots.

For those who appreciate the convenience of on-street parking, Overlook is an ideal choice. Many homes in this community offer ample on-street parking, making it easy for residents and their guests to come and go without the hassle of searching for a spot. This feature enhances the neighborhood’s welcoming vibe, allowing for easy gatherings and a sense of community.

Whether you're a first-time homebuyer or looking to settle down in a serene yet connected environment, Overlook in Portland, Oregon, is a neighborhood that truly feels like home. Explore the possibilities of life in Overlook and discover the charm and convenience that awaits you!

Newest OVERLOOK Homes with On Street Parking

$824,000
5 Beds ⋅ 2 Baths ⋅ 123570049 MLS
This classic Portland Foursquare pairs century-old character with seriously good updates, including: a terrifically updated kitchen, a new cedar deck and backyard retreat, a detached studio; currently the workspace of a design executive, a fully permitted lower-level ADU with its own entrance, an infrared sauna and cold plunge, all wrapped up in an incredible Overlook location near adidas and Killingsworth fun. The Wilbur House pairs period character with a thoroughly modern lifestyle. Four bedrooms sit together upstairs, while a fully permitted lower-level ADU opens the door to rental income, extended stays, independent living or a pretty excellent retreat. A wide open attic presents possibilities to expand, or utilize it as a meditation or additional work space. Out back, life gets even better: a new cedar deck, architectural hardscaping, water feature, playhouse, cold plunge and a detached, modern studio. New and beautiful hardscaping creates a welcoming statement with a newly paved driveway leading to a detached garage. Work here. Make things here. Host people here. Disappear into the sauna and ignore your email here. Whatever the case, you'll love living here. Come see.

5517 N WILBUR AVE, Portland
$595,000
3 Beds ⋅ 2 Baths ⋅ 396520532 MLS
Open Houses Friday, 7/31 from 5-7pm, Saturday 8/1 and Sunday 8/2 from 12-2pm! Outstanding newer construction in the sought-after Overlook neighborhood, just moments from food, drinks, and shopping in the vibrant Mississippi District. This 3-bedroom, 2.5-bath home with a spacious third-floor bonus room offers a fantastic floor plan designed for comfort and versatility. The exceptional primary suite with a bay window, built-in desk, and ensuite with double sinks easily accommodates a king-sized bed, while the second and third bedrooms share a well-appointed hall bath. The expansive upper-level provides endless possibilities as a media room, home office, gym, or guest retreat. Enjoy indoor-outdoor living with a welcoming front porch and a private backyard with a combination of hard scape, squares and recs stone patio and green space bordered by hand stacked river rock. The detached garage offers highly-desired off-street parking and extra storage. Notable updates include a new furnace in 2024 and an EV-charger ready garage! CM3 zoning allows for potential short-term rental opportunity. Buyer to do due diligence with city. Priced at just under $600,000, this well cared for home stands out as an exceptional value. Close to Tri-Met MAX and bus lines, easy freeway access, and countless local favorites including Prost, Fire On The Mountain, and Overlook Park. [Home Energy Score = 5. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10221464]

4222 N MONTANA AVE, Portland
$835,000
705994609 MLS
Opportunity knocks in Overlook! This triplex offers immediate income with two of the three units currently leased, plus a vacant unit ready for an owner-occupant, new tenant, or value-add improvements. Located near MAX and major bus service, with the restaurants, shops, coffee, and nightlife of Mississippi Avenue close by. CM3 zoning offers future redevelopment flexibility while the existing triplex provides income today. A rare chance to invest in a well-connected North Portland location with income today and potential for tomorrow. Buyer to complete due diligence regarding zoning and future development possibilities.

4300 N MONTANA AVE, Portland
$625,000
3 Beds ⋅ 3 Baths ⋅ 515754463 MLS
Sleek, architect-designed townhome-style condominium in Portland’s beloved Overlook neighborhood. This is 1 of only 2 units left out of a total of 8! Designed by Bill Neburka of Evident Architecture and built by award-winning Tieton Building Company featuring undeniable quality and craftsmanship and remarkable detailing. Light, bright rooms w/ walls of windows blend w/ tasteful, timeless, natural interior finishes to create peaceful, Scandinavian-inspired living spaces. An efficient, flexible floor plan makes working from home, entertaining, and hosting guests a breeze. Main floor bedroom + full bathroom! Multiple private outdoor spaces – one on each level of the home – allow for year-round enjoyment of the outdoors w/ little-to-no upkeep to bog you down. The stunning, partially covered roof-top deck, open to the sky in all directions, is unlike any other. Beautiful interior finishes include wide-plank engineered wood floors, rift sawn white oak cabinetry, white quartz countertops, and tile bathroom floors & surrounds. Smart, thoughtful touches, such as a hose spigots on the patio, deck and driveway, keyless entry, programmable sprinkler system, and elevated and engaging landscape design (including strawberry, peonies, magnolia tree, clematis vines, and more), set this home apart from the rest. Situated in an established, community-conscious neighborhood of well-kept homes w/ landscaped yards surrounded by a bevy of fun, iconic restaurants, bars and shops. This super central location minutes from Adidas headquarters offers quick, easy commutes into downtown Portland, NW/Pearl District, and Legacy Emanuel and Kaiser Medical Centers and is just a short drive away from the Portland International Airport. With sophisticated, elevated spaces, minimal landscape maintenance, and an infinitely fun and convenient location, life is just a little easier and a lot more fun here! [Home Energy Score = 8. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10246324]

4625 N CAMPBELL AVE, Portland
$310,000
2 Beds ⋅ 1 Baths ⋅ 461811322 MLS
**SELLER WILL PAY A YEARS WORTH OF HOA DUES AT CLOSING** Thoughtfully designed to maximize every square foot, this light-filled 2-bedroom, 1-bath condo lives much larger than its 915 sq ft! The open-concept layout, high ceilings, 1 bedroom can easily fit a king sized bed, the other room will fit a queen, and oversized windows create an airy, inviting feel, while quality finishes including quartz countertops and hardwood floors add modern style. Located on the top floor, enjoy a peaceful private deck with neighborhood views—the perfect spot for morning coffee or relaxing at the end of the day. There is also a private community garden space with raised beds and beautiful landscaping for those with a green thumb or those who like to relax in the garden. Situated in a quiet area in Portland's vibrant Overlook neighborhood. Easy walking distance from New Seasons, Fred Meyer, and the Peninsula Park Rose Garden. You're just minutes from North Portland's popular restaurants, parks, coffee shops, and MAX light rail stations, making commuting and exploring the city a breeze. Built in 2015 with low-maintenance living in mind, this is the ideal home for anyone looking to enjoy the best of urban living. This home lives like a small house rather than a typical condo. With only six units in the building, no shared interior hallways, a private exterior entrance, and the third-floor location, it offers a level of privacy that many condo buyers are looking for but rarely find.

5734 N MONTANA AVE Unit #5, Portland
$460,000
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
$419,000
2 Beds ⋅ 1 Baths ⋅ 741003872 MLS
Charming Overlook bungalow in one of North Portland’s most sought-after neighborhoods. This home offers timeless character with beautiful hardwood floors, a newer roof, and an energy-efficient Aquatherm heating system for year-round comfort. Enjoy a thoughtfully established garden featuring mature dogwood and lilac, creating a peaceful outdoor retreat. Ideally located near the Adidas campus, New Seasons Market, and nearby parks, with easy access to all the dining, shopping, and community charm that make Overlook so popular. Energy Score of 8, super energy efficient! MAKE SURE TO ASK ABOUT NO DOWN PYMT LOAN, LENDER CREDITS & NO FEE PROGRAMS. [Home Energy Score = 8. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10248618]

2226 N SUMNER ST, Portland
$225,000
1 Beds ⋅ 1 Baths ⋅ 461174053 MLS
Perched on the top floor of a LEED Platinum-certified building, this vibrant one-bed-room condo offers exceptional natural light, modern design, and unmatched access to Portland’s best amenities.Oversized windows, remote-controlled custom blinds, and a skylight in the bedroom fill the space with all-day sun-shine, while high ceilings and bamboo floors create a sense of openness and ease. The open-concept kitchen features soft-close cabinetry, stainless steel appliances, and generous storage. A walk-in closet and bonus in-unit storage solutions keep everything tidy and tucked away. Enjoy sweeping West Hills views and quiet privacy with no neighbors above you. Nestled in a dynamic neighborhood near bike lanes, local restaurants, food carts, and public transit, this home is ideal for anyone who wants to stay connected to the pulse of Portland living.

1455 N KILLINGSWORTH ST Unit #404, Portland
Start Your Search
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.