OVERLOOK Real Estate

Welcome to Overlook, a hidden gem nestled in the vibrant heart of Portland, Oregon. This enchanting subdivision is a perfect blend of urban convenience and natural beauty, making it an ideal place for families, young professionals, and retirees alike. Overlook is known for its picturesque tree-lined streets, charming homes, and a strong sense of community that welcomes newcomers with open arms.

One of the standout features of Overlook is its proximity to the stunning Overlook Park, where residents can enjoy lush green spaces, walking trails, and breathtaking views of the Willamette River and downtown Portland. The park is a hub for local events, picnics, and outdoor activities, fostering a vibrant community spirit.

In addition to its natural beauty, Overlook boasts easy access to Portland's extensive public transportation system, making commutes a breeze. Residents can easily explore the city’s eclectic neighborhoods, renowned dining options, and cultural attractions, all while enjoying the tranquility of suburban living.

The real estate in Overlook is diverse, featuring a mix of charming bungalows, modern townhomes, and spacious family residences. This variety ensures that there’s something for everyone, whether you’re a first-time homebuyer or looking to upgrade to your dream home.

With its unique blend of community, convenience, and natural beauty, Overlook is more than just a place to live; it’s a place to thrive. Discover your new home in Overlook, where every day feels like a retreat in the heart of Portland!

Newest Listings in OVERLOOK

$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

$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

$220,000

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. *Now Offering 1 Year of HOA Dues Paid in Advance!*

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

$199,990

1 Beds ⋅ 1 Baths ⋅ 591933738 MLS

Tucked into the heart of Overlook, this 1-bedroom, 1-bath condo (769 square feet) has been loved by one owner from day one — and it shows. Freshly priced, it pairs a smart contemporary layout with tall ceilings, bamboo floors, and a wall of windows that pulls in soft, steady light from the building's quiet side. This is the kind of great room you don't want to leave. The numbers back up the lifestyle: WalkScore 80 (Very Walkable), BikeScore 99 (Biker's Paradise), TransitScore 54 (Good Transit). Wander to Overlook Park's sports fields and off-leash dog area, graze the Mississippi Ave restaurant row, or hop the Yellow MAX line straight to City Center, Pioneer Square, PSU, and the Rose Quarter. Kaiser Permanente, Legacy Emanuel, and Adidas are all close enough to walk to on a good-mood day. Inside, everything's been tended to: newer appliances (microwave 2020, fridge 2022, dishwasher 2023), in-unit W/D in an oversized bath, fresh paint, A/C, and a 2016 water heater. Kitchen and living room open onto a shared dining space in between — built for slow mornings and second cups of coffee; the bedroom's oversized closet quietly earns its keep. The building takes care of the rest: secured and FHA-approved, with elevator and ramp access, gated parking, a deeded parking space, and a climate-controlled storage unit. Water, sewer, and garbage ride along in HOA dues. Non-smoking, pet-friendly (cats/dogs, 2 max), rental cap met, no short-term rentals — a calm, owner-occupied home base. A 1-year Home Warranty ($570 value) comes along for the ride. Comfort meets convenience, and it's ready for you.

3970 N INTERSTATE AVE Unit #307, Portland

$230,000

1 Beds ⋅ 1 Baths ⋅ 135701225 MLS

Top floor, modern finishes, balcony with mountain views, deeded covered parking, and a spacious, open plan layout flooded with natural light, this one bed one bath Killingsworth Station condo is the one you’ve been waiting for. The high ceilings, sleek bamboo floors, gourmet kitchen, and in-unit laundry make living here so easy. Killingsworth Station is a LEED Platinum certified building with solar water heating and living roofs along with a secure entrance, elevator, and indoor bike parking. Ideally located near transit, shopping, and dining—this is the perfect place to put down roots in the heart of North Portland.

1455 N KILLINGSWORTH ST Unit #415, Portland

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