OVERLOOK Real Estate

Welcome to Overlook, a vibrant and charming subdivision nestled in the heart of Portland, Oregon. Known for its stunning views of the Willamette River and the iconic skyline, Overlook offers a unique blend of urban convenience and suburban tranquility that appeals to families, young professionals, and retirees alike.

One of the standout features of Overlook is its rich history and diverse community. Originally developed in the early 1900s, this neighborhood has evolved into a tapestry of architectural styles, showcasing everything from classic Craftsman homes to modern townhouses. Tree-lined streets and well-maintained parks provide an inviting atmosphere for residents, making it a perfect place for evening strolls or weekend picnics.

Overlook is not just about beautiful homes; it also boasts an array of amenities that enhance the quality of life. Residents enjoy easy access to local shops, cafes, and restaurants that reflect Portland’s renowned culinary scene. For those who love the outdoors, the nearby Overlook Park offers expansive green spaces, playgrounds, and sports facilities, while the scenic views from the bluff are perfect for unwinding after a long day.

Transportation is a breeze in Overlook, with convenient access to public transit and major highways, making commutes to downtown Portland and beyond seamless. Additionally, the neighborhood is known for its strong sense of community, with regular events and gatherings that foster connections among residents.

Whether you’re looking for a place to call home or a vibrant community to explore, Overlook in Portland, Oregon, is a hidden gem that promises a lifestyle filled with charm, convenience, and connection. Come discover all that Overlook has to offer!

Newest Listings in OVERLOOK

$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

$900,000

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 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

$199,900

295529707 MLS

Seize this rare chance to acquire two prime vacant lots with coveted CM3 zoning, situated on the corner of a dead-end street in the vibrant Overlook neighborhood. This location offers close proximity to the bustling N Mississippi Ave, the Vancouver/Williams Corridor, and the Legacy Emanuel Medical Center, all contributing to a phenomenal 91 BikeScore! Previously designed for a 14-unit apartment building, these lots are perfect for a multi-family dwelling or other lower-density residential developments. The CM3 zoning offers flexibility and high-density potential with reduced setbacks, making it ideal for maximizing your investment. Don’t miss out on this fantastic development opportunity in a sought-after area!

N Montana AVE, 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

$250,000

1 Beds ⋅ 1 Baths ⋅ 361446747 MLS

Simplicity in Overlook! This ultra modern LEED Platinum condo features 10' ceilings and a full wall of windows with a private deck to let in maximum natural light. Enjoy an open concept living space with stainless appliances, bamboo floors, in-unit laundry and tons of storage! Secure entrance, bike storage and the MAX line right outside your door. Deeded, covered parking. Electric car charging station. Easy access to PCC, New Seasons, I-5, Alberta & Mississippi districts.

1455 N KILLINGSWORTH ST Unit #417, 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

$749,900

593159608 MLS

Opportunity to acquire one side of a modern home with separate living quarters! This offering provides ~2,557 sq ft of well designed living space across three levels, delivering a functional and highly marketable layout for tenants or owner occupants seeking flexibility. Main level features a great room style design with seamless flow between kitchen, dining, and living areas, plus a convenient half bathroom for guests. Kitchen is equipped with a full size island with eat bar, stainless steel appliances, and extensive custom cabinetry, while large windows and sliding doors enhance natural light and connect to a covered deck and fully fenced yard, a key driver for livability and tenant retention. Upper level offers a 3 bedroom, 2 bathroom configuration including a primary ensuite with walk in closet and walk in shower, along with centrally located laundry for convenience. Ground level includes a highly sought after attached garage and separate living quarters with 1 bedroom, 1 full bathroom, and exterior access, currently rented and providing income from day one, creating flexibility for multigenerational use or continued supplemental rental income. Modern construction, efficient layout, and desirable features position this home for strong long term performance. Located near Arbor Lodge Park, New Seasons Market, and the dining, cafes, and retail along N Lombard St and St Johns, supporting consistent demand and long term value. [Home Energy Score = 10. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10182385]

5623 N GAY AVE, Portland

$749,900

4 Beds ⋅ 3 Baths ⋅ 797183613 MLS

Designed for modern living, I offer exceptional flexibility across three thoughtfully planned levels. Built by a multi-year Street of Dreams builder and Builder of the Year award winner by the Home Building Association, I pair elevated finishes with a layout created for connection, comfort, and versatility. My main level welcomes you with a bright, open great room where the kitchen, dining, and living spaces flow seamlessly together for everyday living and easy entertaining. A convenient half bath adds functionality for guests. My living room is anchored by a fireplace with striking floor to ceiling tilework, while expansive windows fill the space with natural light. My kitchen features a full size island with eat bar seating, stainless steel appliances, extensive custom cabinetry, and a window over the sink framing lush greenery. Stylish lighting and clean modern finishes continue throughout. From the dining area, a sliding door opens to a covered deck and fully fenced yard, extending the living space outdoors for relaxing, entertaining, or enjoying the peaceful surroundings. Upstairs, I offer three well proportioned bedrooms and two full bathrooms, including a spacious primary suite with a walk in closet and walk in shower. Laundry is conveniently located between the bedrooms. My ground level adds exceptional versatility with an attached garage and separate living quarters featuring one bedroom, one full bathroom, exterior access, and dedicated laundry. This flexible space is ideal for guests, multigenerational living, or potential rental income. Set in a well connected North Portland location near Arbor Lodge Park, New Seasons Market, the dining, cafes, and shopping along N Lombard Street, and convenient access to St. Johns, I offer modern comfort, functionality, and everyday convenience. [Home Energy Score = 10. HES Report at https://us.greenbuildingregistry.com/green-homes/OR10182385]

5623 N GAY AVE Unit #2, Portland

$209,000

1 Beds ⋅ 1 Baths ⋅ 591933738 MLS

*** NEW PRICE *** City living, dialed in. This well-maintained charmer sits in the heart of Overlook, in a secured (FHA approved) building with elevator, ramp access, gated parking and secured storage. The scores say it all: WalkScore 80 (Very Walkable), BikeScore 99 (Biker's Paradise), TransitScore 54 (Good Transit). Single-owner and lovingly kept, this 769sqft home pairs a smart, contemporary floorplan with tall ceilings and easy flow. The great room steals the show with a wall of windows pulling in natural light, set on the quiet side of the building. The bedroom keeps things roomy with a large closet, and the oversized bath includes in-unit laundry (W/D included). The kitchen is ready to cook, with newer appliances throughout (microwave 2020, fridge 2022, dishwasher 2023) and a dining area for slow mornings and good company. Add bamboo floors, fresh full interior paint, A/C, and a 2016 water heater, and the boxes keep checking themselves. The perks don't stop at the front door: a deeded, gated off-street parking space and an assigned oversized storage unit in a secured, climate-controlled room. Utilities (water, sewer, garbage) are folded into the HOA fee. The community is non-smoking and pet-friendly (cats and dogs, 2 max). The rental cap (9 units) is met, and no short-term rentals, so the building stays calm and owner-loved. And of course: location, location, location, with Overlook Park (sports fields, off-leash dog park...), the Mississippi Ave restaurants and shops, Kaiser Permanente, Legacy Emanuel, and Adidas, with the Yellow MAX line whisking you to City Center, Pioneer Square, PSU, and the Rose Quarter. Peace of mind with a 1-year Home Warranty included ($570 value!). This is where comfort meets convenience.

3970 N INTERSTATE AVE Unit #307, Portland

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