OVERLOOK Real Estate

OVERLOOK Real Estate

Welcome to Overlook, a vibrant and picturesque subdivision nestled in the heart of Portland, Oregon. Known for its stunning views and rich community spirit, Overlook offers a unique blend of urban convenience and serene residential living. This charming neighborhood is situated in Multnomah County, making it a perfect choice for those who appreciate the dynamic lifestyle of Portland while enjoying the tranquility of a close-knit community.

Overlook is characterized by its tree-lined streets, beautiful parks, and a diverse array of architectural styles, from charming bungalows to modern townhomes. Residents here take pride in their neighborhood, often gathering at local parks for community events, picnics, and outdoor activities. The Overlook Park, a local gem, features sports fields, playgrounds, and walking trails, making it an ideal spot for families and outdoor enthusiasts alike.

Convenience is key in Overlook, with easy access to public transportation and major highways, connecting you to downtown Portland and beyond. The area boasts a variety of local shops, cafes, and restaurants, allowing residents to enjoy the best of Portland’s culinary scene just minutes from home.

For nature lovers, the proximity to the Willamette River and nearby hiking trails provides endless opportunities for exploration and adventure. Whether you’re enjoying a leisurely stroll through the neighborhood or indulging in the vibrant cultural scene of Portland, Overlook is the perfect place to call home. Discover the charm and community spirit of Overlook today, and experience the ideal blend of comfort and convenience in this delightful Portland subdivision.

Newest Listings in OVERLOOK

$649,000
114449775 MLS
This 2-unit property in Overlook consists of a classic PDX Foursquare and a fully separate, mechanically permitted second living space above the XL, two-car garage. Vaulted ceilings, minisplit, its own water heater and laundry, a full bedroom with balcony, and a large living room and kitchen make this a truly independent space with a range of uses from rentals to guests to the ultimate office and beyond. You're not even sacrificing a garage or basement like many houses with in-law suites, here you still have that large 2-car garage and a long driveway so there is plenty of parking for all. Given that you're on a tucked away, dead-end street in Overlook, you don't get a lot of traffic to begin with, so wherever your day starts, it begins peacefully surrounded by trees and plantings. || Sitting up off the street, the house itself has those classic features you'd expect from a 1923 Foursquare: built-ins, central fireplace, social circle floorplan, hardwoods, and that timeless feel. At the same time, the house has been updated with a high-efficiency furnace and mini-splits for year round comfort, double paned windows, modern bathrooms and kitchen, and a trex-style deck right off the main living areas to extend gatherings to the outdoors. Beyond the deck, there's a fully fenced backyard with mature flowering plants || The Overlook neighborhood is a Portland favorite: easy access to Adidas HQ, Kaiser, and transit/commuting, while being tucked away off the beaten path so you can enjoy the unique neighborhood events like Porch Fest, sunsets on the bluffs, and Madrona park a block away at your own pace. [Home Energy Score = 5. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10251899]

2225 N HUMBOLDT ST, Portland

$649,000
4 Beds 2 Baths 374467989 MLS
This classic PDX Foursquare has a huge bonus waiting for you...step through the private, fenced backyard and you'll find a fully separate, mechanically permitted, second living space set above the XL, two-car garage. Vaulted ceilings, minisplit, its own water heater and laundry, a full bedroom with balcony, and a large living room and kitchen make this a truly independent space with a range of uses from guests to the ultimate office and beyond. You're not even sacrificing a garage or basement like many houses with in-law suites, here you still have that large 2-car garage and a long driveway so there is plenty of parking for all. Given that you're on a tucked away, dead-end street in Overlook, you don't get a lot of traffic to begin with, so wherever your day starts, it begins peacefully surrounded by trees and plantings. || Sitting up off the street, the house itself has those classic features you'd expect from a 1923 Foursquare: built-ins, central fireplace, social circle floorplan, hardwoods, and that feel of timelessness. At the same time, the house has been updated with a high-efficiency furnace and mini-splits for year round comfort, double paned windows, modern bathrooms and kitchen, and a trex-style deck right off the main living areas to extend gatherings to the outdoors. || The Overlook neighborhood is a Portland favorite: easy access to Adidas HQ, Kaiser, and transit/commuting, while being tucked away off the beaten path so you can enjoy the unique neighborhood events like Porch Fest, sunsets on the bluffs, and Madrona park a block away at your own pace. [Home Energy Score = 5. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10251899]

2225 N HUMBOLDT ST, Portland

$675,000
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

$589,900
3 Beds 2 Baths 396520532 MLS
Seller is open to supporting a Rate Buy Down program to Reduce Buyers Monthly Mortgage Payments. Built in 2011 and ideally located in Portland’s sought-after Overlook neighborhood, this well-cared-for 3-bedroom, 2.5-bath home offers 1,914 square feet of thoughtfully designed, above-grade living space at a price under $600,000. Just moments from the restaurants, shops, and nightlife of the Mississippi District, the functional multi-level floor plan makes excellent use of the home’s square footage while providing plenty of flexibility for everyday living, working from home, entertaining, and guests.The spacious primary suite easily accommodates a king-sized bed and features a bay window, built-in desk, and ensuite bath with double sinks. Two additional bedrooms share a well-appointed hall bath.An expansive third-floor bonus room adds another level of flexibility and can serve as a media room, home office, creative studio, gym, playroom, or private guest retreat.Outside, a welcoming front porch and private, low-maintenance backyard extend the living space outdoors. The backyard features a stone paver patio, green space, and hand-stacked river rock borders, with room to relax, entertain, or garden.The detached garage provides off-street parking, additional storage, and an EV-charger-ready setup. A new furnace was installed in 2024.Conveniently located near TriMet MAX and bus lines, Overlook Park, the Mississippi District, and neighborhood favorites including Prost! and Fire on the Mountain. CM3 zoning may provide additional use possibilities, including potential short-term rental opportunities; buyer to verify permitted uses with the City of Portland.With 1,914 square feet of above-grade living space, a flexible third-floor bonus room, private backyard, and detached garage parking, this 2011-built home offers an uncommon combination of space, functionality, and location in Overlook at a price under $600,000. [Home Energy Score = 5. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10221464]

4222 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

$305,000
2 Beds 1 Baths 461811322 MLS
**SELLER WILL PAY A YEARS WORTH OF HOA DUES AT CLOSING** Thoughtfully designed to maximize every square foot, and lives like a townhouse, 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

$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

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